"That was some performance there Michele; for a girl who only sucked her first cock a few hours, ago you sure learn fast," he said.

Ellie took her face out of the cop’s lap and turned her head towards Michele.

"See, I told you that you would probably end up liking it didn’t I," she gloated.

The fat cop pushed her face back down on his stubby cock."

"Shut the fuck up and suck my cock bitch," he laughed, "You let those other boys worry about her; you just take care of me."

The fat cop screwed up his eyes and reached down with both hands to push Ellie’s face onto his penis. He bucked in his seat and face-fucked Ellie with short hard strokes. Ellie was working hard at sucking his member and Michele could distinctly hear the sucking and slobbering noises Ellie made as worked on the cop’s cock. Ellie was rocking on her knees, the toes of her black high-heels dug into the cheap carpet, her short black dress had ridden up at the back revealing her white satin panties and matching suspenders clipped to the gauzy taupe stockings encasing her long sleek legs. She looked very sexy. Slutty, but definitely sexy.

Michele felt her penis begin to harden in her sticky panties. She couldn’t believe she could become aroused again so soon after her last orgasm! The sight of Ellie fellating the fat cop was also having its effect on Steve, Joe and Bill; Michele noticed that they were also in various states of arousal.

Joe sauntered over to where Ellie was fellating the cop.

"Mind if I use the other end?" he sniggered at the fat cop.

"Do what you like with her Joe; just so long as she doesn’t lose her rhythm," he laughed back.

Ellie didn’t even flinch; she just carried on sucking away on the cop’s stubby cock. Joe grabbed Ellie’s high-heels and spread them apart, her stockings rasping on the cheap dirty carpet. Joe positioned himself between Ellie’s sleek nyloned legs and took hold of his cock and began to rub it in the cleavage of Ellie’s satin pantied buttocks.

Michele felt her own cock harden and then she became aware that Steve had slid his member into her loose fingers; without conscious thought she gripped the thickening member and began to stroke it. She was mesmerised by what was happening across the room. Bill shifted to the other side of Michele and put her hand on his cock. Michele lay there masturbating the two men while the three of them watched Ellie suck the fat cop while Joe rubbed his cock on her panty clad arse.

Joe reached down and slid the silken gusset of Ellie’s panties to one side and exposed her puckered sphincter. He wet his finger with his tongue and probed at the wrinkled crack. Ellie kept fellating the cop but she also pushed back with her body and Michele watched fascinated as Joe’s finger disappeared inside Ellie’s anus.

"God that looks good," Michele whispered.

Bill heard Michele and took that as his cue. He moved down the bed and slipped his hand under Michele and gently eased her over on her side. She could still see Ellie and the two men across the room and she was still wanking Steve’s hard shaft. Michele didn’t take her eyes off the trio across the room even as she felt Bill slide his hand under her nylon panties and insert a finger inside her semen lubricated passage. She gripped Steve’s cock harder and wanked away at it.

Joe removed his finger from Ellie and spat into his palm then rubbed the spit on his member. He positioned himself directly behind Ellie and nestled the glans of his penis against her sphincter. He reached down and gripped each of Ellie’s silken stockinged thighs in each hand and began to push. He groaned as Ellie pushed back against him until his belly was hard against her bottom and he was buried in her to the hilt. Ellie wriggled her skewered arse and began to suck harder at the fat cop’s stubby member.

Bill rucked Michele’s black leather mini up around her waist and moved down the bed and knelt beside Michele’ pantied rump. He pulled her panties down, the nylon material of her panties whistling on her hosed legs, and left them around one slim ankle. He pushed Michele over further and lifted her leg so that she was lying on her side with her legs scissored open. Bill lay down behind Michele and put his rock hard cock at the entrance to her back passage. He pushed and Michele groaned at the pain as Bill’s glans forced open her tight sphincter.

"Easy honey," Bill whispered into Michele’s ear and the nuzzled her neck, "just relax and it will slide right in; Steve’s already lubed you for me."

And it did! Michele relaxed and then felt Bob’s hard cock slide right up inside her. She was still fascinated by the other trio having sex across the room but she was now very aware of Bill’s body rubbing against hers and his grunts and groans as he fucked her. She loved the feeling of her anus being filled and the shivered with pleasure as Bill’s cock rubbed against her prostate.

Steve had now moved to the edge of the bed and was watching the sex going on around him as he slowly stroked his own cock.

Joe was pounding himself in and out of Ellie; he had moved his hands down to her feet where he gripped her high-heels and rode her like a sleigh. Ellie was a lovely sight to behold with her black chiffon dross rucked up around her waist, her gossamer taupe stockings clipped to her white satin suspenders and her matching satin panties, the gusset eased aside to allow Joe access to her arse. Her pretty face was buried in the fat cop’s lap, sucking his engorged manhood and she bucked back and forth on her knees keeping rhythm with Joe’s pace as he fucked her. Joe was groaning and moaning and the fat cop had his eyes screwed shut and pushed Ellie’s face down into his lap. They groaned in unison.

"I’m coming; oh god I’m coming!"

Michele felt Bob quicken his pace as he hung on to her and pounded his cock in and out of her come slicked anal passage. Michele pushed back against him and wriggled her bottom. Lying on her side like this she was unable to thrust back and forth but her wriggling and pushing caused the glans of Bob’s penis to massage her prostate gland bringing her closer to orgasm. Bob suddenly wrapped his arms around Michele and pulled her back hard against him and Michele felt his cock begin to shudder as streams of hot semen flooded her anal passage. Bob’s manhood spasming against her anal gland caused Michele to climax too and she wriggled her bottom and pushed back against Bob as she shed her spend into her already come-sodden panties.

Steve spun around on the bed and aimed his cock at Michele’s heavily made up face. He groaned and shot stream after stream of hot semen over her face, rivulets of his juice ran down over her eyes, nose and on to her lips. Michele gobbled the salty offering, slavering the fluids with her tongue and licking it into her mouth as her own orgasm shot through her anus, testes and penis. She was experiencing one of the most intense orgasms of her life.

The fat cop pushed Ellie’s head down into his crotch and held her there as he came, he bucked and squirmed in his seat as his emission erupted out of his throbbing cock and deep down Ellie’s throat. Ellie wriggled and struggled tried to pull herself free to prevent herself from drowning on the fat cop’s semen. Joe used Ellie’s struggles for his own gratification and plunged his turgid penis deep into her pulsing anal channel and expended his load, flooding her with a deluge of hot semen. Ellie was nearly asphyxiated when her own orgasm ripped through her and she flooded her panties, a wet stain spreading across the front panel of the white satin garment.

Everyone in the room had climaxed almost simultaneously and they all fell apart and gasped for breath as they came down from their respective orgasmic highs. Ellie was sprawled on the floor heaving in deep breaths. Between her gasping breaths she guzzled the remainder of the fat cop’s spunk. She pushed herself up on her knees and reached up and slapped the cop playfully across the face.

"You bastard," she wheezed, "I know we have played at erotic asphyxiation before; but not when I’ve had a big cock inside me at the same time!"

"Fuck it was incredible though," Ellie smiled and turned around and kissed Joe passionately on the lips.

She looked across at Michele,

"Well was I right or was I right?"

"I told you most of the girls eventually like what they experience here; and I just knew you would be too much of a slut not like it too."

"When our friend in blue here," Ellie nodded at the fat cop, "told us that you had continued on to the party after he made you suck his cock in that parking lot; we knew you would eventually become a willing participant in our little orgy."

Michele was still catching her breath and doing her best to wipe Steve’s coagulating semen off her face.

"Well I’ll tell you what Ellie; you’re a arsehole at work and you’re a cunt of a friend outside of work. But if you ever plan another orgy like this; you better count me in" Michele replied, a smirk breaking out on her face.

Everyone in the room burst into laughter.

As Michele drove back to her sister’s house in the early hours of the morning she pondered on the previous evening’s events. Michele’s sister Angie had revealed that she knew her brother Malcolm (Michele’s alter ego) was a closet transvestite (and seriously hinted that she herself was a lesbian!). Michele’s workmate Jill had let Malcolm make love to her whilst he was dressed as Michele; and Eddie had turned out to Ellie, the most perverted transvestite you could imagine!

Michele had fucked and sucked and been fucked and sucked and had totally fallen in love with the secret underworld of transvestite sex. Ellie had said she would arrange another transvestite and admirer party for the following weekend and Michele was already planning what to wear. What a marvellous twenty-four hours it had been!

When Michele arrived at her sister’s house it was dark and totally silent. She let herself in and staggered to the spare bedroom, shucked off her semen encrusted clothing and wig and fell into bed without even bothering to clean off her makeup. She fell asleep immediately and didn’t wake up until late Saturday afternoon.

Malcolm woke up to find Angie sitting on the end of the bed with a cup of hot steaming coffee in her hand.

"Drink this, shower, shave, brush your teeth, and then come and tell your older sister all about your evening, oh brother of mine!" Angie giggled.

"From the mess your clothing was in you certainly got up to something exciting," she went on.

Malcolm looked groggily around the room.

"Where are the clothes I wore last night," he asked inquisitively.

"Cleaned, pressed and waiting for when Michele re-appears. I even washed, blow dried and brushed your wig," Angie replied.

"In fact after you have cleaned yourself up; why don’t I help you transform yourself again. Yesterday was fun and I’m sure you learned a lot," she smiled.

"I don’t know? I feel kind of weird letting my sister dress me as woman and do my make up," Malcolm frowned.

"Oh fuck that! I know you liked it; now get up and get yourself sorted and meet me in my bedroom. Once I've transformed you into ‘Michele’ I'm sure you will feel more comfortable about telling me all about what happened last night. Let’s just call it ‘girl talk’," she winked, and then got up off the bed and left the room.

Malcolm did as his sister bid and brushed his teeth, showered and shaved. It took a while to remove the caked-on makeup that he had not removed before going to bed but liberal use of moisturiser removed most of it. He was wondering what his sister was getting up to, wanting to help him dress again. The last time she did it, now nearly two days ago, she had put her hand under his skirt and touched him through his panties. What was that about?

Malcolm had been crossdressing for so long now that his mind automatically switched from thinking of himself as Malcolm to Michele as soon as he began to transform himself.

When he came back into the bedroom wearing only a bath towel around his waist he found Angie sitting on the bed surrounded by a selection of feminine clothing, most of which Michele had worn the previous evening. It was now cleaned and pressed. A packet of Kaiser Ultra Sheer stockings replaced the laddered and come-spattered hose he had worn home. Michele’s wig and makeup were arranged on the dressing table.

Angie was wearing a pleated navy blue skirt that came to just above her knees. She wore a white satin blouse that exposed her cleavage, navy-blue high-heels and sheer tan hosiery. She was also wearing full makeup and jewellery. She looked quite hot for a woman of her age.

"Where are you going dressed like that?" Malcolm asked.

"Nowhere. I’m going to help transform you into Michele and then we are going to discuss what happened at the party," Angie answered walking over the dresser and patting the chair, indicting Malcolm should take a seat in front of the mirror.

"You do your makeup this time and I’ll only help if you need me to ok?" Angie said.

"Ok," Michele replied, taking off her towel and sitting down at the dresser completely nude.

Michele’s finger and toenails retained the two coats of glossy plumb red that she had applied on Friday afternoon so they only needed touching up where the nail polish was chipped. She applied a thick coat of foundation to her face and then set it with matching face powder. She brushed dark blue eyeshadow onto her eyelids and then applied a coat of pink out to the far corners of her eyes, lightening the makeup and blending the two shades. Next she applied jet-black eyeliner to her upper and lower eyelids, applying three coats and touching up here and there when Angie directed her.

"So far so good Michele," Angie cooed, "But of course you’ve had years of practice you naughty closet queen," she giggled.

Michele applied thick black mascara to her upper and lower eyelashes, and then blush to her cheeks, feathering it along her cheek-line and smoothing it up so that it almost merged with her eyeshadow. Then she dusted her whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.

She painted on the base coat of the two-coat plum coloured lipstick just like she had been taught by her sister, being careful not to smudge her lip-line applying the clear top coat over the base colour coat.

Michele positioned the wig on her head and adjusted and brushed it until it was sitting perfect with the fringe straight.

Michele had again made the transformation from a plain, smooth-faced man to a heavily made-up middle-aged whore with brunette hair framing dark exotic eyes, rouged cheeks and seductive red lips.

She turned towards her sister, who looked at her critically and said,

"Wonderful Malcolm; you have again transformed into Michele," Angie said and stroked Michele’s face gently with her long red fingernails

"Let’s see you get dressed then," Angie said, helping Michele to her feet and leading her over to the bed.

Angie patted Michele playfully on the buttocks.

"You look good enough to eat," she laughed.

Michele was again confused by her sister’s actions.

"Angie," she whispered, "are you some kind of a lesbian or something?"

"I’m an ‘or something ok’?" Angie answered.

"I like men; no I love men; but I like certain kinds of women too."

"I’m bisexual I guess. I’m a lipstick lesbian."

Michele looked at her sister confused. Angie went on,

"I like to have sex with feminie women; not the hairy ‘man-hater’ type of lesbians that are often the stereotype. Do you get what I mean?" she finished.

Michele nodded and sat down on the bed and started getting dressed.

She slid into the red lace suspender belt and adjusted it so that it sat around her waist and then took the stockings out of the packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her legs. She clipped the stocking-tops onto the garters hanging from her suspender belt. She carefully straightened the back-seams keeping the nylon taught; smoothing out the wrinkles as she went. Next she slid the red satin bikini panties up her nyloned legs and pulled them snug around her buttocks and crotch.

Michele hooked the red brassiere around her chest stuffed the cups with the old pairs of pantyhose that she had used to fill them with before. She stood up and stepped into her black leather mini and adjusted it at her waist ensuring the hem was nice and straight at mid thigh. Next she pulled on the leopard-skin nylon blouse, buttoning the blouse and tucking it into her skirt.

Michele walked back over to the dresser and sat down. She clipped on the silver mounted ruby drop earings clasped the matching necklace around her neck and the matching bracelets on both of her wrists. She slid the four large silver rings on her fingers, two on each hand. Michele bent down and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above her ankles. She sprayed a liberal amount of ‘Poison’ perfume all over finishing with a quick spray under her skirt.

"There; transformation complete," Michele turned her pretty face up to her sister’s.

"Not quite," Angie said and kneeled at her brother’s feet.

"You forgot this," she said fastening the silver anklet below Michele's left ankle.

Michele felt her penis stir as her looked down at her sister’s attractive face so close to her crotch and felt Angie’s slim hands slide over her stockinged ankle. She wondered what was going on here between her and her sister.

Angie slid her manicured fingers up Michele’s sleek leg and her hand disappeared under the black leather mini. Her fingers stroked the naked skin above Michele’s stocking-tops and she looked up at her brother.

"Come on Michele, sit next to me on the bed and tell your sister all about what happened to you last night," Angie said removing her hand from under Michele’s skirt.

Angie stood and helped Michele up on her high-heels and led her to the bed. They sat side by side close to each other and Michele began to tell her sister the full story of what had happened from the minute she had left her Abgie’s house for the party yesterday, until she returned in the early hours of this morning. Angie hung on every word.

"Absolutely fascinating Michele," Angie said.

"I wish I had been there! But you must have been quite scared when those guys had you tied to the bed like that. Men can be such pigs sometimes," she said, and put her arm around Michele.

Angie looked into Michele’s pretty painted eyes and Michele stared back into Angie’s heavily made up face. She hadn’t before realised how sexy Angie looked when she was dressed and made up like this. Angie moved her head forward so that their faces were only centimetres apart and parted her red lipsticked lips. Michele felt her cock harden in her panties.

"Angie; we shouldn’t. We’re brother and sister." she whispered.

"We’re Angie and Michele," Angie responded and kissed Michele deeply, their lipsticked lips mashing together and their tongues intertwining.

Michele gently pushed Angie away and stood up on her high heels, her hard cock tenting the front of her skirt.

"It’s incest Angie; it’s wrong," she whispered.

"As far as I’m concerned you are Michele, a hot fuckable woman who happens to have a real penis instead of a strap-on; not my brother Malcolm!" Angie replied.

"You’re no different to all the other women who I have fucked over the years," she went on, "and I can see you like what we are doing," she said pointing to Michele’s erection visibly tenting her leather miniskirt.

"Wouldn’t you like some this," Angie said and lifted her skirt.

"I expect you’ll be very busy indeed," Eddie’s laughter faded as he disappeared down the corridor between the cells.

I cringed at the thought of another night in this caged prison brothel, forced to service some of the roughest men I had ever met. At the same time I was feeling confused as to how quickly I had acquired female mannerisms; how I had become aroused by wearing the lingerie, makeup, wigs, and heels that Eddie forced me to wear. I was also amazed at how, after only a brief introduction, I was developing the skills of the feminine art in applying makeup.

I was more disturbed however, by how I had responded to the sexual attentions of some of the punters and the ministrations of my crossdressed sisters. I could not deny that, despite the fact that during this torrid night I had been repeatedly orally and anally raped, I had experienced two of the most intense orgasms of my life this evening. I decided that I was just too dog-tired to think about it; I needed to sleep. I was even too tired to be angry with Charlotte and Carmel, who although they had obviously enjoyed the sexual encounter we had just experienced together, had obviously been put up to it by Eddie so that he could enjoy the ‘all girl’ show.

The two vixens in question, (who had just introduced me to my first transvestite lesbian experience), slunk out of my workroom cell. They both glanced back and blew me a kiss.

"Nightie-night sweetie," they giggled in chorus, the sound of their laughter and the clattering of their high heels diminishing as they moved on down the corridor.

Mabel came in and dumped my prison fatigues on the bed and pointed to the door with the words,

"Out! Shower. Get changed!"

I got the message and slipped out of my feminine attire and deposited it in the laundry bin in the corner of the cell. My heels and breast-forms went inside the large wardrobe. I removed my wig and put it on a vacant wig-stand then took the towel Mabel proffered, cinched it around my waist, and headed once again down the passageway between the cells carrying my fatigues to the shower block.

The overhead lights suddenly clattered on revealing the workroom cells on either side of the passageway. Through the open bars I stared at the oversized double beds, rumpled satin sheets, large armoires and dressers with makeup mirrors, totally incongruous in this disused prison wing. The workroom cells were like islands of perfumed femininity amid a sea of stink created by caged men.

Mabel poked her head out of my cell and barked orders to a couple of prisoners who I recognised as weaker individuals who had ‘no muscle’ and therefore had shitty jobs working in the prison laundry. They were stripping the beds and dumping sheets and pillowcases into large wheeled washing carts. They were also emptying the laundry bins from each cell into individual oversized prison laundry bags; I noticed the laundry bags were each labelled with the cell numbers and the feminine names of the ‘working girl’ that used each cell. As I passed one of the laundry hands I saw him bring a pair of soiled panties to his face and rub the bulge in the front of his denim jeans. I scurried past disgusted.

The laundry was a big money maker for the prison. It catered for the needs of the prisoners, the guards, and also took in work from nearby hotels and a hospital. Eddie controlled the prison laundry, as he did just about everything in Chelmsford prison. Obviously also had the laundry workers working overnight to wash and dry the bedclothes and clothing that belonged to his ‘working girls’. To make his prison prostitution operation work he must also have the laundry dry cleaning service clean the ‘girls’ skirts, blouses, jackets and other items of clothing.

The cleaning of feminine clothing had to be being done overnight as I had made many trips to the prison laundry during the day whilst working as Eddies accountant and I had never seen any items of female attire in there. I knew Eddie made a considerable amount of money from the laundry; and of course, he was paying off someone high in the prison authority so that he could run the laundry business. As his accountant I knew he would also be charging the ‘girls’ for the laundry service; Eddie made money off everything, he gave nothing away.

When I got to the shower block I ran the water as hot as I could get it and soaked myself for half an hour in the shower trying to wash away the shame and humiliation of the last few hours. I scrubbed my face repeatedly to remove the caked on makeup. The blush, lipstick and eye shadow came off easily but I had to scrub at my face continually with the washcloth until it came away bearing no traces of foundation or mascara. I poured nail polish remover onto a cloth and cleaned the red nail polish from my fingernails.

I moved to the mirror and was glad to see that I looked like a man again; but then I noticed that some mascara was still clumped here and there on my eyelashes and little clots of eyeliner were smudged in the corners of my eyes. I picked up a bottle of moisturising cleanser from the shelf under the sink and removed the last traces of ‘Michele’ from my body.

I winced as I pulled on my denim prison uniform fatigues and felt the scratch of stiff cotton on my body instead of the luxurious feel of satin, silk and nylon. ‘Stop it!’ I told myself as I found myself wishing I could exchange the scratchy denim and cotton work-wear for the soft feel of feminine garments; ‘this is how you are supposed to be dressed Mike; as a man!’

I made my way back to my accommodation cellblock without further incident. I was amazed to find my cell unlocked and unguarded. Fucking Eddie ran the whole prison I was sure if it! I let myself into the relative privacy of my own cell. With only a peephole in the door for the guard to look through instead of the open bars of the workroom cells in E Block it was as private as one could get in prison. As my head hit the pillow my mind was spinning with what had happened to me, how drastically my life had changed in one day. The last thing I noticed through teary eyes before I fell into a deep sleep was the clock on the wall ticking over to 2:30am.

I awoke the next morning and looked straight at the clock; it was 9:30am. Eddie must have arranged it with the guard on my wing to let me sleep in. I was tired and sore from the events of the previous evening and the early hours of this morning, I just couldn’t believe what had happened to me. I seemed normal enough (or as normal as one could be when you are a guest in Chelmsford prison); just Mike. Mike brushing his teeth, Mike combing his hair, Mike changing into clean fatigues. Mike drinking coffee alone in the deserted cafeteria. There was no sign of Michele or her feminine ways; Christ I wished it were all just a bad dream!

I looked down at my hands holding the coffee cup and noticed that there were little crescents of red nail polish under the cuticles of some of my fingernails. "Fuck!!!" I exclaimed. Then I heard the voice I feared most; Eddie had snuck up on me and whispered in my ear,

"Come on Secretary you’ve got a lot of work to do. Just because I’ve found you some after-hours employment, doesn’t mean you can neglect your day job," he snickered.

I followed him and took up my usual post working on Eddie’s books as I had done every day for the last few months. I couldn’t bear to bring up with him the events of last night or even look him in the eye. What I did do though was to pay particular attention to those parts of Eddie’s business that had now come to directly effect me. Because Mabel ran the books relating to the prostitution ring, I had never really paid them too much attention before, except to check the bottom line for profit against loss; today I paid them special attention.

how Eddie’s prison business works and how Mike/Michele ended up becoming Eddie’s accountant and ‘secretary’.

A note for those of you who haven’t read Part I of this story; you probably need to read it now to understand

It was all there, the amount each punter paid Mabel for a ‘session’ with each ‘girl’ (there were various codes that I didn’t really understand but as some sessions cost more than others, I could only deduce those punters wanted ‘special services’ and paid accordingly). Here was listed the earnings made by each of Eddie’s transvestite hookers against the costs involved in running his secret prison brothel. Payments were listed to Mabel, the guards (although a lot of the guards seemed to take their payment in ‘trade’), and the inmate ‘minders’ Eddie employed (I shuddered as I though about how ‘Iron-bar Steve’, his most vicious minder, had used me).

The costs of female attire, lingerie, cosmetics, perfumes, wigs, shoes and other accessories were carefully recorded against each girl’s name and deducted from her earnings. It appeared that despite these costs, and even after Eddie had taken the larger part of the profit for himself, the girls still made a substantial amount of money. By prison terms they were rich; in fact they probably made more money than your average streetwalker did on the outside.

Then I looked up the ledger entries Mabel had made against me, ‘Michele’; I was astounded at how much money Eddie had made from me last night, even though only a couple of my ‘tricks’ were paying customers. Then I looked in the debit column at how much money I owed Eddie; I was flabbergasted. I owed him thousands of dollars for the clothing and accessories he had purchased for me!

"What the fuck Eddie?" I turned around and shook the ledger book at him.

"This is bullshit! I’m a rich man outside but it will cost me double the money I owe you in bribes to have that much smuggled in!"

"I suppose I have no fucking choice, It would take me weeks to pay this off earning the money you expect me to make in your filthy whorehouse!"

I couldn’t believe that in my outrage I was shouting at Eddie like this.

"Oh no Secretary bird; months at least; probably a year to clear that debt!" he laughed.

"What the fuck?" I stammered.

Eddie reached out and grabbed my slender throat,

"You can only pay for the goods and services I provide for you with the services you provide to me!"

"What the fuck does that mean?" I asked. "Why can’t I just pay you out from money I have on the outside?"

"All of your clothes, makeup, wigs, nylons and those nice frilly things I have you wear, you have to pay for out of the money you make in the workroom. That’s the deal. How do you think I keep my little harem working for me?" he responded.

"And of course you will always need more of those lovely things, because, as you can imagine, they tend to get worn out quickly and suffer more than their fair share of wear and tear during the working day; or should I say working evening," he laughed.

"And I can’t have my punters complaining that my girls dress like shit now can I?" he mocked.

"Besides; look on the bright side, you get to keep everything you pay for and I’ll let you keep any tips; pardon the pun," he laughed.

"In a few weeks, once you get to like the work, you will be asking for more and more clothing, lingerie, and girly luxuries, all my girls do," he finished.

"Girls?" I stammered.

"Girls! Girls! Fucking GIRLS!!!!!"

"They’re crossdressers you dolt! They’re men! Men! MEN!!!"

"And so the fuck am I! I’m a fucking MAN not a GIRL!!!!!"

Whack! Everything went black.

I woke up on my bunk in my cell my head throbbing.

"Christ!" I groaned.

Eddie had obviously belted me during my outburst and knocked me out. I raised myself off my bunk and looked in the mirror. No visible damage done; just a bump on the back of my head. Eddie was too smart to mark his latest money-spinner.

I noticed my cell door was closed and on further inspection locked. Then I noticed a suit-bag hanging on the end of the double-bunk. On the disused top-bunk was a pair of black high-heeled open toe sandals, a makeup case, a pair of expensive Italian pantyhose still in their wrapping and some boxes that when opened contained white satin lingerie. A wig composed of a shiny black bob, with discrete cerise highlights was perched on a wig-stand. I recognised it as one of the wigs Carmel had had me wear last night. The wig had been cleaned, combed and styled; the harsh prison light bulb picked up the highlights in the hair.

I walked over to the suit-bag and noticed a note pinned to it. It read:

‘Get dressed. Be ready by 1pm and make sure you look good for a special friend of mine. Steve will pick you up.

Or don’t get dressed, your choice!

If you’re not dressed when Steve gets there you won’t need to get dressed in anything but hospital pyjamas for at least a month!

Love Eddie

XXX’

Resignation came crashing down on me yet again; I would not be able to get out of Eddie’s clutches until I was released from Chelmsford…or… a glimmer of hope formed in my mind…transferred!!! That was it! I would get a transfer! I had plenty of money outside; sure it cost me double every time I tried to get any of my money smuggled in, but if Eddie could bribe the guards, surely I could too! All I needed to do was to find out the right person to bribe. I made a resolution right there and then. I would withstand whatever depravity I had to until I could arrange a transfer to another prison. With this resolve firmly in my mind I started to get dressed into the clothing that had been bought into my cell whilst I was unconscious (probably delivered by Mabel in her male alter ego: the washed up trustee lifer).

I shucked out of my prison fatigues and stood naked in the centre of my cell. Short, slim and well proportioned with all of my body hair removed my body did not look especially feminine; but it was more womanly compared to most of the inmates in here who were either bodybuilders or had resigned themselves to lives of flabby inactivity. Maybe I could fatten myself up so that I wouldn’t be attractive to men? Then I remembered Charlotte, the chubby whore from last night, being fat had not worked for her, it had just made her more attractive to men who liked larger women (BBW’s as they were referred to in men’s magazines).

I opened the large makeup case and investigated the contents. It contained plenty of makeup, a small bottle of perfume and some jewellery in the upper compartment tray. I removed the upper tray to discover that in the bottom compartment was a pair of breastforms. The two silicone tits looked forlornly up at me from the bottom of the case. Breastforms! This time yesterday I wouldn’t have had a clue that the fucking things even existed. I selected the ruby red nail polish out of the makeup case and sat down on my bunk and painted my toe and fingernails contemplating the future. Eddie obviously had a special trick lined up for me this afternoon; what he didn’t know was the trick I was going to play on him; if I could just find out who I needed to bribe to get out of this nightmare.

I laid out the makeup on the shelf in front of the mirror over the sink and started the transformation from Mike to Michele.

I applied a layer of heavy foundation from my hairline all the way down to the bottom of my neck. Next I applied a second layer of Revlon foundation that matched my natural skin tone and then set the foundation with a lighter shade of face powder. I rouged my cheeks to highlight my sharp cheekbones, applied another light dusting of powder, and then went to work on my eyes.

My eyebrows were thin anyway and just required a light touch of pencil to form the arches. I applied a pinkish hued eye shadow to my eyelids and then blended a light aqua from there to just under my eyebrows. With a fine brush I applied black eyeliner in a thin line on my eyelids as close to my eyelashes as possible, top and bottom. I took the line right into the corners of my eyes as I had been taught. I applied lashings of black mascara to my eyelashes, only having to clean up a few little flecks that dropped onto my face. Next, three coats of the same plum coloured lipstick that I had worn last night, carefully applied inside the matching lip-liner. I pulled the black bob onto my head and adjusted the wig so that it sat correctly. I clipped a pair of silver and diamond encrusted sapphire drops to my ears and a matching pendant around my neck to finish the effect. I looked gorgeous; Carmel would have been proud of my efforts I thought to myself.

Now, to the foundation garments! I unwrapped the expensive looking Italian pantyhose. The diaphanous sheer black nylons were fully fashioned with dark reinforced cuban heels and toes; a neat black seam ran up the back of the legs to the top of the waistband. The gusset was as sheer as the rest of the hose with no joining seams or cotton insert that is usually found in the crotch area of most pantyhose. The nylons were decorated with tiny little rhinestones just above the heels.

I sat on the edge of the bottom bunk and slipped on the sensuous hose being careful not to snag them. My legs looked stunning, the little rhinestones made the pattern on the outside of each of my calves, the cuban heels tapered into the back-seam. I adjusted the seams to run perfectly centred up the backs of my legs. As I smoothed the hose little sparks of delight flew up my legs and I felt myself begin to stiffen. Before I could become further aroused I pushed my penis between my legs and held it there with the tight nylon gusset. These hose must be really expensive I mused.

Next I slid the white satin panties up my legs sending more little darts of pleasure into my body as they rubbed on the nylons. I stood and pulled the panties into place around my bottom and crotch. They were pure white, sleek and discretely laced around the waistband and leg openings. The full cut white panties stood out dramatically against the black nylon pantyhose; the seat of the full-cut panties encased the globes of my buttocks perfectly and the front panel was tight against my crotch with just my little package spoiling the effect.

I removed the breastforms from the makeup case and stood before the mirror and put them in place. I had applied a liberal amount of artist’s gum to my chest and the back of the breastforms as directed by the label on the tube I had found in the case. The directions on the gum promised to hold them in place ‘for hours on end’; they certainly felt secure. I just hoped the fucking things weren’t glued there permanently.

I put on the white satin bra next. Still a novice, this proved to be the hardest garment to get into. In the end I clipped the catches at the back of the bra together and pulled it on like you would a T-shirt, arms in first then pulled the back strap over my head. I wrestled the garment into position and smoothed out the sleek satin cups over my false breasts and untangled the straps over my shoulders and around my back. It was a lovely fit, perfectly matching the satin panties with a lace trim along the top of the breastcups with a single pale pink satin rose nestled between them.

The last item of lingerie in the packages was a full slip of the sheerest translucent white nylon. I slipped the item over my head and pulled it down so that the bodice fit snugly against my torso; the slip flared at the waist and finished mid thigh. The hem was trimmed with lace matching my bra and panties. The gossamer thin garment felt luxurious and when the material stroked against my nyloned thighs little explosions of pleasure ran up my legs.

I stepped into the patent leather black high-heeled sandals, my painted toenails visible through the reinforced toes of my stockings, the pretty cuban heels accented by the ankle straps of the shoes. I bent down and fastened a silver anklet around my left ankle; the chain sparkling as the light reflected off it accentuating the miniature rhinestones on my sleek hosed calves.

I stood up and unzipped the suit-bag. Inside was a navy blue suit and sheer white nylon blouse. I slipped into the blouse, the cool feel of the nylon sleeves sliding up my arms, the light material whispering against the full slip as I buttoned the garment. I stepped into the skirt; it was snug at the waist and tight around my hips and bottom, the hem coming to just above my knees. I pulled on the wide lapelled jacket and my transformation was complete.

I looked in the mirror stepping back so I could see as much of my reflection as possible. I was no longer Mike, the weak willed accountant; I was Michele, a power dressed executive; a ‘fem fatale’ in a business suit. I sprayed liberal amounts of perfume on my neck, behind my ears and then as Carmel had showed me, under my skirt.

I was about to sit down when my cell door slammed open. ‘Iron Bar’ Steve stood there in the company of one of the guards.

"Oh fuck me Steve she’s fucking gorgeous; I’d love to shag her bent over the bunk dressed just like that!" the dimwitted guard exclaimed.

"Fuck off stupid, you couldn’t afford a fucking hand job off her, she’s out of your league," Steve responded.

‘How chivalrous,’ I thought to myself, ‘A brain-dead thug defending the honour of a crossdressed inmate prostitute to a corrupt prison guard!’ I couldn’t help but smile at the irony of the situation.

"Oh you won’t be smiling for long honey," laughed Steve, "Eddie’s special friend doesn’t like jokes from fag inmates one little bit."

"Who are you calling a fag Stevie? You couldn’t get enough of me last night could you?" I clipped sarcastically.

Steve raised his hand but I stood defiantly in the doorway of the cell. I knew that Steve dare not touch me at the moment as I was all prettied up for some special punter. It was good to actually feel a slight empowerment for once. I sashayed though the cell door deliberately taunting Steve but I paid the price as I passed him; he reached out and squeezed my pantied buttocks through my skirt.

"Don’t touch the merchandise Steve," I taunted again, turning my pretty face to his and pouting at him.

"Oh don’t worry Michele, I’m just here to escort you to your special date, but you will be well used merchandise when you return," he laughed.

I looked around the cellblock and noticed it was empty. All of the prisoners were at work of course, but I couldn’t see any guards either, other than the dimwit who had unlocked my cell and was now making his way back to the guard’s office at the end of the block.

"Oh don’t worry honey, you’re getting the red carpet treatment, no one is going to see where your going except for a select few in the know," Steve said, tapping the side of nose..

Steve led me through a series of doors and deserted corridors. I never saw another soul; the doors opened electronically when Steve swiped a keycard though each of the card reading devices fitted next to the door-locks. ‘Who the fuck is Eddie’s special friend?’ I thought, ‘He must have some clout to be able have a crossdressed prisoner led halfway through the jail without anyone seeing it happening.’ ‘And who the fuck gives prisoners like this maniac escorting me the keys to the jail; this was just fucking insane!’

We finally arrived at a set of fire stairs, the door to which Steve opened with a swipe of his card. He led me up three flights of stairs, me tottering on the high-heels I was still unaccustomed to wearing. He opened the door at the top of the last flight and held me back as he scanned the corridor for a few seconds.

"Ok, quickly now," he said grabbing my wrist and pulling me into the corridor behind him.

"This is his private entrance; I’ll pick you up from here in hour. Behave ok!" Steve whispered in my ear, kissed me gently on the earlobe, and pushed me through an unlocked wood paneled door and slammed it shut behind me.

I half fell through the door and as I glanced up I could just make out the name embossed on the door; in faded gold leaf lettering it said WARDEN.

Warden Stone was a large man and as I fell though the door he caught me in his strong arms.

"You must be Michele," he smiled, gazing directly into my eyes.

"Here take a seat," he insisted leading me to a large leather divan set against one wall of the large office.

I was mesmerised; I knew that things were obviously way out of the ordinary in this fucked up jail. What with Eddie running every legal and illegal activity he could, including a lucrative brothel staffed by crossdressed feminised prisoners, corrupt guards and inmates running around with the keys to the doors; it was just farcical. The lunatics were literally running the asylum. But this! The Governor admitting a crossdressed prostitute, delivered by a messenger from the hardest criminal in the jail, into his private office; this was beyond comprehension!

But then again; in some fucked up way it made sense. How could Eddie possibly get away with what he did in here without the blessing of the Governor. In fact it made even more sense as I quickly caught on to the enormity of the situation; this was where Eddie’s largest payments went to; the Warden, they were obviously partners. The Warden ran the jail but Eddie ran everything inside the jail and the Governor got his cut; including the fringe benefit of access to Eddie’s working girls whenever he wanted. How else could all this be explained?

At the same instant another lightning bolt struck me; I was now with most powerful man in Chelmsford prison, if anyone could get me a transfer out of here it was him! I decided right then and there that I was going to be very nice to the Governor; no matter how disgusting his needs were, I was going to tend to every one of them willingly. After all, this could be my only shot at getting out of this nightmare. ‘So Mr Stone,’ I thought to myself ‘You’re about to have the wickedest hour you ever spent with one of Eddie’s whores!’ I mustered my resolve and made my move.

"Why thank you Warden Stone," I offered him by biggest smile and sat down, crossing my legs in a ladylike fashion so that the hem of my skirt rode up to mid thigh.

I noticed his eyes open wide and heard a sharp intake of breath as he heard the soft rasp of my nylons rubbing together and stared at my thighs encased in their gauzy nylon sheaths.

"Stanley please," he smiled back.

"And you are Michele I’m told," he went on.

"Well Michele let me paint a picture for you; I’m sure you are not naïve and understand why you are here. But there is no need for this to be unpleasant for you; I assure you that I can behave like a gentleman, and this scant hour we have together can be a welcome break for you from the filth and depravity you experience very day in my prison."

"So Michele, shall we spend a nice relaxing hour together?" he asked expectantly.

"Why Warden, I mean Stanley; if you are the gentlemen you already appear to be I’m sure I can behave like the lady you want me to be. Perhaps we can even accommodate each other in other ways if you would like to discuss a proposal I have for you?" I responded maintaining my painted smile.

Warden Stone’s face clouded over at my proposal; I had gone too far too early; I went into damage control.

"But of course that’s for later, please sit with me," I patted the leather couch next to me and batted my lashes like a good little coquette.

Stanley smiled again and managed to drag his gaze away from my legs to my eyes.

"Lovely, but please, allow me to get you a drink; scotch?"

"Please," I smiled back and he turned to an expensive looking oak cabinet to pour the drinks.

‘I might as well make the most of this,’ I though to myself as I glanced around the Warden’s impressive office. As one would expect it held all the trappings of power; a large desk, chunky furniture, the wall adorned with certificates, trophies and pictures of the Warden with other powerful men. On his desk I noticed a picture of the Warden and his family. His wife appeared mousy and his daughter was a skinny teenager with dank hair; they were smiling painfully for a picture obviously posed to project family harmony. I wondered what his mousy wife would think if she knew that Stanley’s peccadilloes ran to intimate encounters with crossdressed prison inmates?

Stanley returned to the large sofa, stopping off to turn out the overhead lights and check that the door to his outer office was locked and the shades lowered. He set the drinks down on side table and adjusted the one remaining lamp to a diffused glow. ‘Very cosy,’ I thought to myself; ‘I bet his receptionist is on an errand for an hour or so.’ I wondered how often he did this?

The Warden handed me my drink and indicated the vacant place beside me on the sofa,

"May I Michele?" he asked smiling.

"Of course Stanley," I smiled, again patting the seat beside me.

Stanley sat down heavily beside me and the cushion gave way under his weight so that I leant in towards him slightly, the golden liquid and my red fingernails glimmered in the diffused lamplight as I raised my glass to him.

"Cheers," I whispered and drank heavily from my glass.

"Cheers," he responded, downing the spirit in one huge gulp.

Stanley had to be over a hundred and thirty kilos and close to two meters tall; well proportioned but large; I noticed the beginnings of a paunch hanging over his belt as his suit jacket opened. ‘Ok this is it,’ I decided; ‘lets get this façade over with!’

I reached out and took his empty glass from him and placed it on the side table beside mine, a crescent of lipstick decorated the rim of my glass.

I turned to face the Warden and reached out to him, gently taking his head in my hands, I pulled his face towards mine seductively opening my lips slightly. Stanley groaned and pressed his lips lightly against mine. He kissed me softly, with his mouth closed; then he reached out and put his strong arms around me and eased me against him as he smothered my face with feather soft kisses. He kissed me all over my face; my lips, my cheeks, my forehead, and placed little butterfly kisses on my lightly closed eyelids.

"You are so beautiful," he whispered in my ear, gently nuzzling my earlobe.

My hands were now on his powerful shoulders and we embraced each other for a few minutes; softly kissing each other, I felt the heat slowly growing in him as he became aroused.

I felt his hand slide down my body and come to rest on my knee; he softly massaged my leg, slowly working his hand higher, lightly stroking the inside of my stockinged thigh. His breath was becoming heavy now but he made no attempt to force himself on me; his mouth remained closed as he tenderly rained down soft kisses on my mouth and face.

I reached out with one hand and placed it on his thigh feeling the hard muscle through the material of his trousers; the back of my hand brushed briefly against his tumescent member; he gasped.

"Oh Michele; you naughty girl!" he whispered, his hand sliding under my skirt came into contact with my slip.

The Warden wrapped his hand in the silken material and began to slowly glide the slip up and down my thigh. The feeling of the delicate fabric rubbing on my pantyhose was exquisite; my member began to awaken in the silken gusset of my hose; my tight white panties holding it in place as it slowly thickened and elongated.

I moved my hand across the bulge growing in the Warden’s trousers and found the zipper on his fly. He removed his hand from under my skirt and gently moved my hand away.

"No Michele, I want to taste all of your sweet treasures before we consummate our little interlude," he said and took hold of my upper arms in a tight grip.

‘Quite the wordsmith,’ I though to myself; ‘I wonder what sweet treasures he intends to enjoy?’

Stanley kissed me fully on the lips, pressing his torso hard against me, slowly sliding his tongue into my mouth; I tasted my own lipstick on his tongue as he gently explored my mouth. Then he pulled his face away from mine and eased me back against the padded armrest of the divan. I guessed that now he would want more than just kisses and caresses and as he adjusted his position on the sofa I made to remove my suit jacket.

"Oh please no Michele; I want you dressed just as you are. I love a woman who can pull off the whole power-dress performance thing and still look feminine and sexy."

"Do you like the lingerie? I had Eddie acquire it for you just for this occasion; and those nylons, God, I could eat you up in those. In fact I think I just might," he chuckled.

I relaxed back against the padded armrest and Stanley bent down and lifted my legs so that I was lying lengthways on the divan. I was lying with my back supported by the padded armrest and my legs across Stanley’s lap.

"That’s better," he smiled and began to stroke my legs with his hands.

"Oh that feels so sensuous, and I just love those little rhinestones sprinkled on your stockings," he said.

He bent his head and raised one of my legs to his mouth and commenced planting sweet little kisses all up and down my calf. He moved his lips slowly up and down my lower limb and then licked the back seam of my stocking all the way down to my high-heeled sandal. He kissed my feet, and pushed his tongue into the darker reinforced extremity of my hose and sucked on my painted toes through my open toe sandals. I must say it felt quite erotic.

Stanley used his free hand to stroke my other leg sliding his fingers far up under my skirt, stroking up and down my leg slowly and sensuously.

"Mmmmm let me see," he groaned and lifted his face from my feet.

He opened my legs slightly and raised my skirt up around my waist. He gazed upon me lying there with my stockinged legs in his lap with the hem of my slip coming halfway down my thighs, the pure white nylon slip in contrast with the dark hosiery.

"Lovely," he said, and began to kiss me up and down my legs again.

This time he buried his head under my slip and continued up my legs right to the top of my thighs. He kissed the front panel of my satin panties whilst stroking my legs. After a minute or so of placing soft kisses on my panties and thighs he made his way back down my legs and began to suck on my nylon sheathed toes again. His hands were now sliding the soft material of my slip up and down my thighs creating wonderful sensations through my body. My member was stiffening further and was becoming uncomfortable being held in place under my crotch by my pantyhose and tight panties.

Stanley was now licking my shiny black patent leather sandals, holding both my feet in place by the spikes of my heels. As he worshipped my feet and gazed up my legs, his eyes glazed over with lust; then he started sucking on the spiky high-heels, taking them into his mouth and lovingly caressing them with his tongue; first one then the other; as if fellating my heels.

He was panting and groaning as he worshipped my legs and feet. Then he moved one hand down to his fly and pulled on the zipper. His hand disappeared inside and rummaged around eventually freeing his erection; it protruded stiffly from his trousers, red, angry and engorged.

Stanley lifted my feet and re-positioned them one on either side of his hard cock and slowly started to fuck my feet. I realised what he was doing and assisted him. I slowly started to masturbate him with my feet, slowly lifting them up and down, letting my soft stocking foot caress the head of his penis and then the patent leather of my shoes.

Stanley threw his head back against the cushioned divan and let me foot fuck him. He renewed his carnal attack on my legs as I wanked him with my feet. I trapped his member my feet and stroked hard. He moaned and writhed in ecstasy.

Then he looked at me again and gently moved my feet out of his crotch. He stood up and re-positioned himself on the divan so that he was kneeling between my spread legs. With trepidation I thought, ‘Here he goes; he’s going to fuck me.’ But he didn’t. Stanley closed my legs and lifted my feet up to his mouth and began to worship them with his lips and tongue again. I was lying down full length on the divan now with just my head pillowed on the armrest, my skirt and slip rucked up around my waist with my legs lifted up whilst Stanley took oral pleasure on my feet and calves. Now I knew what ‘sweet treasures’ the Warden wanted to taste; he was a foot fetish. ‘Well at least I might leave here without having to gratify him in some other disgusting way,’ I thought to myself.

Stanley was now in a frenzy, lapping and sucking at my shoes, toes, and feet; he was panting, his face red and sweating. Stanley actually looked quite pathetic dressed in his full suit with just his stiff penis poking out his trousers as he paid homage to my peds. He stopped briefly and quickly fumbled at his waist, undoing his belt and pushing his pants down around his thighs. Then he gripped my ankles, lowered my legs and pushed my feet together. He pulled my feet between his legs so that his cock lay in the silken valley created by my calves. Then he started to fuck my legs.

He rubbed against me faster and faster and I could feel the friction of his hard cock against my nylons. Stanley groaned and whimpered. His gaze alternated between my face and my pantied crotch as he pushed his cock against me harder and faster.

I decided that I would assist him with his fantasy and placed two slender, red-nailed fingers on the gusset of my pure white satin panties and began to stroke. Stanley reacted immediately.

"Oh yes Michele! You naughty, naughty girl!"

"You are such a pretty girl, but such a naughty girl," he chanted.

"Oh Michele, you naughty nyloned princess I’m going to come; I’m going to come all over your pretty toes and feet; would you like that?" he begged.

"Yes Stanley please; please come all over me!" I role-played for him as he approached his climax.

He shifted his grip to my ankles again and pulled my feet up to his quivering member. I knew exactly what he wanted and began to masturbate him hard and fast between my feet; pushing back and forth with my legs so that my high-heels and stockinged feet ran up and down the length of his shaft. At the same time I furiously rubbed the front of my panties; a parody of a woman pleasuring herself.

"Come for me Stanley; come on honey, come for Michele baby," I cooed.

Stanley’s face screwed up and went bright red as a shattering orgasm washed over him. Ropes of creamy semen jetted from his penis splashing up my legs. Spatters of his spend formed sticky white pools on my calves and feet; they glistened in stark contrast on my black stockings. My diaphanous black hose became darker still in the places where Stanley’s semen soaked into the nylon.

A silvery thread of Stanley’s ejaculate hung down from the heel of one my shoes forming a sticky necklace between my foot and his deflating penis.

"Oh Michele, that was wonderful," Stanley gasped and collapsed on top of me.

His weight nearly knocked the breath out of me as he started to cover me my face with soft kisses again. I pushed lightly against him until he took the hint and rolled off me so we were lying side by side. Stanley pulled me close against him, one arm over my body caressing my buttocks, slowly stroking the sheer nylon slip against my panties. His kisses grew harder and his tongue now invaded my mouth; I could hardly breath. I managed to pull my face away from his.

"I’m glad you liked that Stanley; was that how you wanted to take me?" I whispered in his ear.

"Oh yes Michele, but that was just an entrée sweetheart; I recover very quickly," he whispered back.

"Perhaps a drink Stanley, before we play some more?" I asked.

I was getting confident now; the Warden was obviously a submissive, I had read that powerful men often liked to take on a submissive role during sex play. I decided to test my theory.

"Come on Stanley, pour me another scotch and we can discuss a proposal I have for you. If you are a good boy and treat me nice I might let you have some more," I teased.

I was not prepared for what happened next; I had hopelessly misjudged the situation.

The Warden used his powerful build to roll me onto my back and pull himself up so he straddled my waist. One huge hand came across and swiped me on the side of my face, stinging and numbing me.

"Oh I don’t think you realise the situation here bitch! I’m the fucking Warden of this jail and you’re just another slag who Eddie provided for me to use as I see fit."

"Don’t try and offer me proposals! I make the fucking proposals here!" he screamed at me.

"Now here’s a fucking proposal; lift your fucking trollop arse up off my lounge," he yelled.

Warden Stone stood up and dragged me off the divan and shook me like a rag doll. I was terrified; the man had turned from being a gentleman to a demon in the space of seconds.

"Here’s another fucking proposal," he barked and shoved me hard towards his desk.

I tottered on my heels and reeled over towards the desk; one of my shoes flew off and my stockinged foot slid on the polished floor. I reached out trying to grab the desk for support but I collapsed on the floor beside the desk, legs akimbo.

"And here’s my final proposal," the Warden bellowed and moved in, pulling me up off the floor and bending me over the huge oak desk.

One bear-like hand grabbed my skirt and tore it from my body; the side seam splitting with a loud rip. The Warden pushed me down harder on the desk, he put one hand on the back of my neck and mashed my painted face onto the hard surface of the desk. With his free hand he pulled my slip up and over my back and I realised how exposed I was in this position. I was bent over the desk with my skirt ripped off, my slip hiked up, tottering on one heel, my satin pantied buttocks raised and exposed.

Warden Stone let go of my neck briefly but it was no relief; I was horrified by what he did next. He put both hands on my hips and yanked my panties and pantyhose down in one swift movement. They tangled in a bunch at the top of my thighs.

"No! Please, Stanley don’t do this," I whimpered.

"What you mean this, you cocksucking whore," he taunted and I felt him position himself behind me, his swollen penis probing at my buttocks.

"No! No! Please!" I begged.

"Well what do you think of my proposal Michele?" he grunted and pushed forward with all his weight.

"Ohhhhhhh god no!" I moaned as his member slid all the way up inside me.

I felt as though I had been split open. It was so tight and he was in me so deep that I could feel his groin hard against my bottom. Then he raped me. He just fucked me like a whore. Bent over the desk I could offer no resistance as Warden Stone commenced thrusting in and out of me. I don’t know how long he ploughed himself into me; at least ten minutes; he obviously had plenty of staying power having just recovered from an orgasm only minutes ago.

He grunted and groaned, calling me filthy names and slapping my buttocks as he fucked me hard and fast. His cock pistoned in and out of me and his groin slammed against my buttocks. I forced myself to relax my sphincter but the pain was still excruciating. Eventually the lubrication from his pre-seminal fluid eased some of the pain as his invading member continued to rape me.

Eventually he bellowed, grunted and puffed and suddenly I felt the hot ooze of semen inside me. The Warden wasted no time and pulled himself out of me immediately. He yanked my panties and pantyhose up over my buttocks and I felt him wipe his penis clean on my buttock; his warm spend left a wet patch on the cheek of my bottom. I remained bent over the desk, silent and humiliated, feeling vile and debased as the Warden pulled up his pants and shoved the tails of his shirt into the waistband of his trousers.

There was a gentle rapping at the wood paneled door through which I had entered the office only an hour ago. The Warden grabbed my arm in a vice-like grip and dragged me across the office. He opened the door and threw me outside like a piece of garbage; I tripped and fell to my knees on the hard polished floor tearing my beautiful pantyhose. I looked up to see ‘Iron-bar’ Steve smirking down at me. The Warden briefly disappeared back inside his office, then returned to the doorway and threw my shoe and my ripped skirt at me.

"Tell Eddie I’ve finished with this for now. She’s one of his better whores, but she has too much of a mouth on her," Warden Stone barked at Steve and slammed the door shut.

 

 

 

 

 

Malcolm was a middle manager in a small business in a large city.  Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life.  Malcolm had a few girlfriends over the years but never anything serious; he kept himself to himself and rarely socialised outside of a small circle of colleagues and close friends he had cultivated over the years.  Malcolm was boring really; but he one closely guarded secret.  Malcolm was a crossdresser.

 

Once or twice a week Malcolm liked to lock all the doors of his modest two-bedroom suburban home, close all of the blinds, take the phone off the hook, and dress like a woman.  It had started as nothing really serious; as a child he had liked to play with his older sister’s panties and nylons; he loved the feel of the garments against his skin and occasionally he would wear his sister’s underwear for an hour or two and then carefully place it back in the laundry basket.  His fetish continued into his teens and when he finally left home and got a place of his own be bought his own panties, stockings and pantyhose and would spend the odd evening dressed in the silky articles.

 

Malcolm enjoyed his fetish alone and never talked about it to anyone, not even to whoever his current girlfriend might be at the time.  Every now and again he was successful in talking a girlfriend into wearing stockings or pantyhose during sex and he loved the sensation of fucking her as she wrapped her nylon encased legs around his body; but it was not the same as wearing them himself.  After a few years he also added petticoats, slips, suspender belts and other lingerie to his collection.  Then the internet explosion happened.

 

Like most men Malcolm went searching for pornography on the net and concentrated on searching for sites which contained lingerie and hosiery fetish.  Then one day he typed “men in pantyhose” into his web-browser and as he explored the matches to his search he came across a few sites dedicated to crossdressing.  He followed the links further and further into the cyber-world of crossdressing and he was fascinated by it.  He saw so many pictures of guys dressed not only in lingerie but fully dressed as women; wearing women’s clothes, shoes, wigs and makeup.  He became hooked.

 

Eventually he summoned up enough courage to acquire some clothes, makeup, shoes and a couple of wigs.  He would buy the items whilst he was away on business; never in his home town; he was terrified of being caught.  And so Malcolm went on year after year, dressing up once or twice a week, home alone and surfing the net where he entered chatrooms to chat on line with other closet crossdressers about all sorts of TG issues.  He soon discovered that the world of the Transgendered was often confusing and mostly secretive.  A few of the girls he chatted with on line were Transsexuals and wanted to live their lives as women.  Some Crossdressers dressed so well that they could pass as women but were not at all interested in becoming women; they just loved to dress as women and sometimes they got together.  They called themselves Transvestites and some of them met up to share their experiences or just to be in each other’s company; some of them belonged to an organisation called the Seahorse Club.  Other Transvestites met up to have sex with each other or with men. He discovered that the men who liked to have sex with Transvestites were called Admirers and they trolled the chatrooms and websites looking to arrange meetings.  But most of his online friends were like him; for reasons many and varied, all they wanted to do, or most often all they could do, was to dress up at home and enjoy what they could of their fetish, alone or in the cold world of cyberspace.  A lot of them were married men who kept their crossdressing activities secret or ‘in the closet’ as the colloquial term was known. 

 

Yes it was a very exciting but confusing world out there in TG land and up until now Malcolm was content with his lot; he never dreamed of going out dressed as a woman and even though he sometimes fantasised about meeting other Crossdressers or Admirers he was too scared to do so.  Malcolm was just too terrified of being caught; he was horrified of what the consequences might be if his colleagues and friends; or even worse his if his family found out about his secret.  A couple of times he had summoned up the courage to wear pantyhose and panties to work under his male attire and even though it had thrilled him he had one bad incident which had scared him from ever doing that ever again.

 

Malcolm got on with everybody, especially everyone at work; he was friendly, cheerful, a good listener and worked hard.  But there was one person there who just didn’t like him.  The guy’s name was Eddie and he was the office jerk.  If there was an office prank or someone was the butt of a practical joke, then you could pretty much guarantee that Eddie was behind it.  He was annoying, but harmless enough and very productive; the bosses liked Eddie and turned a blind eye to his misgivings because he earned well for the company.  In fact the only other manager whose department earned more than Eddie’s was Malcolm’s; maybe that’s why Eddie was particularly vindictive to Malcolm with his petty practical jokes.  Malcolm mostly ignored Eddie’s jokes and snide comments but one day he let his guard down and paid a hefty price.

One day Malcolm had gone to work one day wearing black sheer to the waist pantyhose and pink nylon panties under his business suit and was enjoying the thrill of being dressed that way secretly in public.  On the rare occasions he went to work wearing pantyhose and panties he was very careful to make sure that his secret was safe; if he had to go to the toilet he would use the cubicles that had full length doors and when seated at his desk he checked every few minutes to ensure that his shirt remained tucked in, in the unlikely event that the waistband of his pantyhose or panties might show.  This day he had to go pee and went to the men’s room and locked himself in the end stall, contented that he could lower his trousers and do his business without being caught dressed in panties and hose.  He hung his suit coat on the hook on the back of the cubicle door, lowered his pants and sat on the toilet seat with his panties and pantyhose bunched around his ankles.  What he didn’t know was that Eddie had followed Malcolm into the toilet to play a prank on him.  Malcolm never found out what the prank was; all he ever knew was that it somehow involved Eddie standing on the toilet in the stall next to his and looking over into Malcolm’s stall; maybe Eddie was going to throw a glass of water over  him or something equally inane. 

 

What did happen was that Malcolm heard snickering and looked up to see Eddies grinning face peering over the adjacent stall. Malcolm was horrified and just looked up slack jawed. Eddie just said,

 

 “Nice underwear sweet-cheeks,” and his face disappeared from view.

 

Malcolm spent the rest of the day, then the week, and then month in agony waiting for Eddie to torment him and ridicule him in front of his colleagues; he thought up ridiculous excuses as to why he might be dressed that way but the best he could come up with was that it was a bet; but with who?  As it turned out Eddie never said anything to anyone else; he just occasionally sidled up to Malcolm and whispered,

 

“Are you wearing them today?” winked and walked away.

 

Eventually Malcolm decided that Eddie was too scared to bring up what had happened because he would have to explain his own actions; spying on a man doing his business in a toilet stall.  Malcolm figured Eddie was content to just torment him occasionally with the question as to wether he was wearing female underwear to work.  Malcolm never wore female underwear to work after that; he remained content to just play dress-up at home.  Until one day………………

 

Every year on the anniversary of firm’s founding, the bosses paid out for a big party; it had become a tradition.  The party was fancy dress and it was held on the evening of the last working day before the Christmas break.  Over the years it had become customary for the party to have a theme; and the theme had a twist. The twist was that whatever the theme was, the women dressed in the male or dominant role and the men dressed in the feminine or submissive role.  One year it was ‘cops and robbers’; where the women came along dressed as policemen or prison warders and the men arrived dressed as criminals or prisoners (lots of horizontal striped shirts and black masks that year; like the Beagle Boys in the Scrooge McDuck comics).

 

One year had been ‘toffs and paupers’; lots of the women dressed in top hats and tails and the men dressed in the rags similar to the scallywags in Oliver Twist.  There had been ‘cowboys and Indians’ (girl cowboys, boy Indians); ‘heroes and villains’ (girl heroes, boy villains); and last year, the best yet, had been ‘knights and damsels’ with the girls dressed as knights, valets and lords of the realm, and the men dressed as medieval princesses and ladies of the court.  Everyone had a big laugh at that one, especially the men who had really got into the spirit of the thing with lots of them dressed up in drag in crinolines and ball gowns.  It was a big laugh for everyone.  Malcolm was tempted to dress up in his favourite lingerie, a ball gown, wig and makeup; but in the end had chickened out and came dressed as a court jester.

 

This year it was Malcolm’s turn to choose the theme because he had been voted the worst dressed at last year’s party.  The judging panel had decided that his court jester’s outfit was a copout on the theme and, as per tradition, the person voted worst dressed had to choose the theme for the following year.  It was considered a task not to be taken lightly; the more outrageous the theme the more acclaim it received; and the person who chose an interesting and outrageous theme became the most popular man in the company; for at least a few months anyway.  Malcolm had wrestled with the decision as to what the theme for this year’s party should be.  Malcolm being Malcolm, everyone expected something boring like ‘spacemen and aliens’ or some other safe subject matter, but they were all surprised and delighted when in late November Malcolm posted the theme for this year’s party on noticeboard. It was ‘Whores and Pimps’.

 

Of course Malcolm had his own secret agenda; for years now he had wanted to go out in public dressed as a woman.  Not like last year, dressed in a costume, but dressed in real women’s clothing, fully made up and feminised.  This was his big chance, and of course the more effort he made to be feminine the more he could justify it; after all, as the party’s organiser it was expected that he would endeavour to dress up as realistic as possible in keeping with the spirit of the theme.  The only concern he had was when he received an email from an anonymous address that simply said; ‘I might have guessed’, Malcolm was sure that Eddie had sent him the email but after a few days he pretty much forgotten about it.

 

Malcolm agonised for weeks as to how he could get away with dressing up as realistically as possible and to have a valid excuse as to why he looked so good dressed as a woman.  Last year the men who had dressed as ‘damsels’ had looked pretty ordinary; sure they had hired great costumes, crinoline ball gowns, tiaras, ladies slippers and so forth; but most of them had five o’clock shadow and their makeup was garish and clown-like, their wigs cheap and knotted poor facsimiles.   Then he had a brainwave; he would get his sister to dress him and make him up!  He could answer any questions as to why he looked so good dressed as a woman truthfully; “My sister dressed me and made me up,” and if anyone asked her, she would verify his claim.  She would be his unwilling alibi.

 

Malcolm hit the chat rooms in the days leading up to the big party and all his online friends encouraged him and offered advice; everything from “Don’t do it!” to “Go for it honey; stay out all night and pick up a nice man!”  Malcolm was a little perturbed about that last remark because sometimes, when he home alone dressed as a woman, he fantasised about what it would be like to be with a man whilst he was feminised.  He also hit lots of Transvestite web sites like TVChix, KTM, Crossdress World and so forth looking at pictures of Transvestites he admired to find the right ‘look’ for the party.  He wanted to look slutty but not trashy; sort of up market streetwalker.  He found a lot of girls in the UK and Europe had mastered the look he wanted capture; that dark haired beauty Lyn in the UK had the look; so did Janet Petteflet in Holland, Wendy Stockings in Scotland, and Cherry in Melbourne Australia.

 

Malcolm finally made up his mind as to how he wanted to look for the party; and then he had a dilemma that he hadn’t thought of before; one of his online girlfriends had asked him what fem name he was going to use.  When he was online he just used the handle ‘loves-to-dress’ and because he had only ever dressed alone he and had never talked to anyone in the real world about his transvestism, there had  never been a reason to have a fem name.  It would be easy to think up some trashy name to use at the party; everyone wore nametags at the party and they were usually the same absurd double entendres you heard on bad British comedies.  Names such as: ‘Sir Shagsalot,’ ‘Baron Ivor Bigun’ and ‘Princess Swallows’ had been some of the more ridiculous names used by partygoers last year.  He wanted a name that he could use at the party and that he could keep forever as his own secret name for when he crossdressed.  He thought about it for a few days and finally decided on a name.

 

He wanted a first name close to his male first name, but not so close that it was obvious; and his crossdressing had originally started out as a fetish for panties and hosiery; so the name came to him in an inspiration.  He played with the name Melanie for a while but decided that it was too close to his real male name.  He settled on Michele; Michele with one L, because it was a little bit different.  Malcolm decided his fem name would be Michele Nylons.

 

By the time the day of the party arrived Malcolm had made all of the many arrangements required of him as the organiser. The venue was the small function room of one of the cheaper city hotels, the catering, drinks and entertainment were part of the venue’s package; the firm paid for the party but they didn’t lend themselves to extravagance; after all the party was just really an excuse to dress up stupidly, get drunk and let off steam.  Also the firm’s thirty or so employees preferred the venue to be at one of the cheaper hotels because, as most of them and their partners got drunk at the party, they usually rented hotel rooms at the venue.

 

The previous weekend Malcolm had called his sister on Friday evening and explained to her about the party and his need to dress up as a whore for the theme; he then went on to clarify why he needed to look as realistic as possible because he was the host and organiser it was expected oh him, and begged her for her help.  He went on to say that he had some ideas as to how he wanted to look and that he had even got hold of some pictures off the internet to help him decide how he should look.  As he had no idea how to dress like a woman she would have to help him.  She eagerly agreed and was pleased that the normally quiet, reserved Malcolm was coming out of his shell for this event.  She told him to bring along the pictures on Saturday morning and they would go shopping for everything they needed so that Malcolm would look as whore-like as possible; it would be fun!

 

When Saturday arrived Malcolm met his sister Angie in the city outside of a large department store.  He had already figured out that he needed to behave naive when it came to world of women’s clothing and makeup; but he was determined to ensure he got exactly the look he wanted; he would have to be cunning that’s all.

 

“Hi Angie,” he said, and kissed her cheek when she arrived outside of Myer; one of the better stores in town.

“Hi Malcolm,” she responded.

“Let’s get you feminised then, you hussy,” she laughed, and Malcolm blushed; ‘If only she knew the truth,’ he thought.

“Come on; lingerie first,” she said enthusiastically and took his hand and led him into the store.

They made their way to the lingerie section of the store and started looking around.

“When you say you have to look as realistic as possible does that mean underwear too?” she asked.

“We can get away with some cheap foundation garments if you like; we can squeeze you into a cheap bra and you can just wear your own underwear under women’s clothing if you like?” she added.

Malcolm was horrified at the prospect.

“No; definitely not!” he enthused, “If we are going to make me look like a hooker, then lets go all the way; I want to win best dressed and who knows how good some of the other guys will look; it can be quite competitive you know and it might come down to who is wearing the best knickers!” he laughed, hoping he hadn’t gone to far and given his real motive away.

“Alright then; lets turn you into a complete slut,” Angie giggled, “This is going to be fun!”

“My boring, unadventurous, brother is really getting into the swing of things.  It’s about time!” she added.

Angie led Malcolm to the brassiere section of the lingerie department and he pleaded ignorance as she expounded the various virtues of the different types of brassieres.  They eventually settled on red satin full cup, size 14C.

“Red is definitely a whore’s colour,” she chuckled “and your panties should match; they usually have a matching panty for the better quality brassiere you know?”

“Do they really?” Malcolm responded feigning ignorance of such things.

“Here they are!” she quipped, delighted at having found the matching item on the rack of panties below the bras.

“Now I reckon any whore would love these,” she laughed, “here; what do you think?” she asked holding a pair of red satin bikini panties up for him to see.

“How the fuck would I know Angie? And do you have to hold the fucking things up for everyone to see they’re for me?” he pretended to be angry.

“Oh don’t be silly Malcolm; if anyone asks we just tell them the truth.  Besides you will have to try on some of the clothes anyway, at the moment I’m just guessing your sizes,” she responded.

“You mean women have different sizes to men?” he quizzed.  Malcolm knew exactly what size he was in women’s clothes and shoes but he couldn’t let on.

“Of course; at the moment I’m guessing your about a 14; a larger size for a woman even though you take a medium size in men’s clothing.”

“Ok,” Malcolm tried to sound befuddled but she had nailed his size in one guess.

“Now if you want to look like a real whore then we had better get you some stockings; we can get stay-ups or we can get the type that require garters or a suspender belt; what do you think?”

“Definitely suspender belt!”  Malcolm responded a little to eagerly.

Angie looked quizzically at her brother and he reddened.

“Angie; I’m a man so I have seen plenty of pictures of scantily clad women in my time and the sexy ones always wear suspenders and stockings,” he responded.

“Suspenders and stockings it is then,” she laughed.

“Oh I just love this one; and it matches the panties and bra,” she said, reaching for, and then holding up a red lace garter belt with six long red suspender straps hanging from it.

They wondered over to the hosiery section and began to browse.  Angie rummaged around and eventually held out a package to Malcolm.  ‘Sheer Fully-Fashioned Seamed Stockings by Kaiser” the label said.  A little clear window in the package displayed that the stocking were black.

“Perfect,” Angie said. “Whores always wear black stockings.”

“Mmmm,” she mused, “Show me your legs.”

“What?” Malcolm responded caught unaware by the request.

“Show me your legs stupid,” she repeated and reached down and pulled up one leg of Malcolm’s pants up to his knee.

“Just as I thought; hairy! That will never do!  Even though these stockings are black your hairy legs will show through; we’ll have to get you some pantyhose to wear under them,” she went on; dismissing Malcolm and rummaging again amongst the many packages of hosiery on the shelves.

“Just the thing!” She sounded delighted and flung another package at Malcolm.

This time the label said ‘Kolotex Sheer To The Waist High Sheen Pantyhose.’ ‘Colour – Taupe’.

“Jeeze, I didn’t realise it was so hard being a woman?” Malcolm laughed; again pretending ignorance but secretly pleased at all of the selections Angie had made so far.

“Ok buster; now comes the hard part; skirt and blouse.” Angie went on and led Malcolm further into the store.

“Didn’t you say you had some pictures?” Angie asked.

“Well I got these off the net,” Malcolm said. “Apparently the women in the photos are really men; Transvestites I think they are called.  They look realistic to me though.”

“Malcolm; you are the dark horse; I never dreamed you would know about such things!” Angie looked shocked as Malcolm handed her the pictures.

“Well I never did know anything about this until I had to organise this fucking theme party!” Malcolm pretended to be angry again.

“I just entered a few keywords into my browser and these are some of the pictures that it came up with.  And I’ll tell you what; some of the other pictures were actually pornographic.  Do you know there are some sickos out there that actually LIKE dressing as women?” he went on.

“Malcolm you have led a sheltered life haven’t you,” Angie answered but she was now too busy looking at skirts to carry the conversation on any further.

Angie looked at the pictures and looked at some skirts on a rack.  She poked around for a while selecting items and then putting them back. Finally,

“Yes; this is it!” she squealed.

Angie held out a black leather miniskirt looking extremely pleased with herself.

“It’s just like this one the girl; well man; well whatever; is wearing in this picture,” she said; pointing to a picture of Janet Petteflet which Malcolm had downloaded from KTMGirls. 

“Now for the awkward bit; you will have to try it on.”

Malcolm paled; he hadn’t though of that.  He knew that he was usually a size 14 in a skirt but also knew that sizes varied; he had a couple of 12s and even a 16 at home.

“It’s no good frowning and looking sorry for yourself.  If you are going to spend all this money to dress up for one stupid party we at least better make sure the clothes are going to fit you.” Angie scolded.

As it turned out it wasn’t that difficult.  Angie being Angie just went up to the floor supervisor and told her the truth; that Malcolm had to dress up in drag for a party.  The supervisor, an attractive woman in her fifties, was only too delighted to help.  She led them to a single fitting room that had a full length door that was separate to the rest of the female fitting rooms.

“We keep this room for special clients and the handicapped; It’s separate to the rest of the fitting rooms and very discreet.  Just find me when you have made your selections and I’ll see to you personally,” the floor supervisor smiled.

“Right; now a blouse!” Angie went on and charged on through the women’s clothing department to where there were what looked like thousands of blouses.

Malcolm was so glad that he had though of using his sister as a ruse; she seemed so enthusiastic and was actually having fun selecting clothes for him.  This was going a lot easier than he thought it would; he didn’t have to explain what he wanted at all; Angie was taking the lead and selecting just what he would have chosen to wear himself.

“Finally!” Angie exclaimed holding up her prize after what seemed like eternity as she waded through a sea of blouses and tops.

It was a sheer nylon leopard-skin patterned, longsleeved blouse and it was perfect to go with the black leather miniskirt.

“Right lets get you sorted brother of mine; go and wait by the fitting room.” Angie dictated and stormed off back towards the skirts.

A few minutes later Angie returned with the floor supervisor; her arms loaded with clothing.

“I’ve got the skirt and blouse in size fourteen and sixteen,” she said “Try them on in there and make sure they fit properly; can you do that?”

“I know,” she went on, “take this in with you and try to make sure you look as good as the girl in the photo,” she said, handing him the picture of Janet Petteflet.

Malcolm went into the booth knowing that the size 14 skirt would be perfect; and it was.  The size 14 blouse was too short in the sleeves and tight in the shoulders; the size 16 would have to do even though he would have preferred it to be tighter around the waist.  Malcolm came out of the fitting room and handed his selections to Angie and the others to the floor supervisor.  Angie wasted no time and dragged him over towards the footwear department.

“The fucking blouses button up the wrong way,” Malcolm whined; again pretending ignorance in the matter of female attire.

“No they don’t; men’s shirts button up the wrong fucking way, you lummox,” she quipped, and continued to drag him along by his sleeve.

When they got to the ladies footwear section it was blessedly easy.  Angie went straight to a pair of black, patent leather, high heeled sandals. Malcolm made a stupid gaffe as Angie looked at a size chart,

“Size ten,” Malcolm said, not thinking of the consequences.

Angie spun around and looked him quizzically.  Malcolm blushed a deep red and stammered,

“I read somewhere that women’s sizes are two sizes smaller than men’s.  You know it’s one of those bits of useless information you pick up,” he offered as an explanation.

Angie continued to stare at him questioningly for a minute and then turned back to the rack of shoes and selected a pair of size tens.

“Here; try these,” she said handing him the high heels.

“There’s no one around, just try them on ok,” she warned before Malcolm could offer a protest.

Malcolm sat on a stool and removed his loafers and socks and tried them on; a perfect fit.

“Lovely! I’ll show you how to walk in them tomorrow Malcolm; you will find it difficult but no self respecting whore would wear anything except high heels,” she laughed, regaining her previous joviality.

“Accessories and makeup next!” Angie charged ahead again.

“Accessories? Makeup?” Malcolm quizzed.

“Oh just go to the in store coffee shop Malcolm and I’ll meet you there later,” she tried to feign anger but laughed.

Malcolm did as he was told and Angie joined him about twenty minutes later.  Sipping on a latte she showed him what she had acquired in his absence.  There was a slim gold belt with a silver buckle, a gold clutch purse, a selection of makeup (to which he showed absolute ignorance for sake of appearances), and what seemed to be far too much jewellery for one night’s dress-up.  They finished their coffee and took their selections to the checkout where thankfully Angie presented the purchases to the cashier and all Malcolm had to do was hand over the cash.

Angie again led the way and this time they stopped in hairdressing salon.  Angie explained that it was her favourite salon. And the best hairdresser in town worked there.

“I could take you to a fancy-dress store and rent something tacky or we could go to a novelty shop and get one of those awful novelty wigs but you did say you wanted to look as feminine as possible so I’m afraid you will have to fork out for something good.  On the bright side; if the wig looks good on me too I might buy it off you after the party,” she said.

Angie took charge of the situation and entered into a deep discussion with one of the hairdressers whilst Malcolm stood there with his hands full of shopping bags trying not to look embarrassed.  Eventually he was led into a small room at the back of the hairdressers where he was seated and introduced to Stephan, Angie’s hairdresser.  Angie and Stephen then seemed to have the time of their lives trying different wigs on Malcolm.  They finally both agreed on one, and Stephan held up a mirror so that Malcolm could see.  It was brunette with some lighter highlights; the hair was straight but curved slightly at the neck and fell to just on his shoulders; the fringe just covered his eyebrows.  It was lovely but of course Malcolm just said,

“Well if you think its ok we’ll take it” and paid up.  He made a fuss about the price, secretly pleased that the wig was perfect for the shape of his face.

Outside the hairdressers they parted ways; Malcolm was disappointed when Angie took all the purchases from him,

“It’s not as if you need them until next Friday is it? And as you are coming around my place to for me to dress you properly and make you up I might as well take them home,” she said cheerfully, kissing him on the cheek and walking off towards where her car was parked.

“Thanks for all the help,” Malcolm responded and walked away excited. He could hardly wait for next Friday.

All week the office was abuzz with talk of the party; many of the staff discussed how they were going to dress.  Some were just going to squeeze into their wives clothes; some had gone to costume-hire specialists.  The girls were having a great time rummaging out old flared purple pants, platform shoes and other outrageous seventies pimp apparel. Malcolm kept quiet despite the friendly ribbing that he copped from some of the staff; they joked that boring old Malcolm wouldn’t know a whore from a boar or that he would probably come looking more like a washer woman than a prostitute after last year’s feeble effort.  The only quip that disturbed him was an aside from Eddie,

“She’ll look gorgeous I’ll bet.”

Malcolm didn’t know if Eddie was joking or being sarcastic but he didn’t care; he was too excited and looking forward to the party for reasons that none of his colleagues could imagine; Michele was making her debut!

Friday afternoon finally came and Malcolm drove around to his sister’s place in eager anticipation.  The firm had finished work early and he had a few drinks after work with some of the staff and they had said cheery farewells until later that evening.  He arrived at Angie’s place as instructed at five o’clock having showered and shaved as close as possible ensuring his face was smooth and without a trace of stubble. He had a gin and tonic to steady his nerves before leaving home and Angie greeted him at the door with another.

“To help you relax dear brother,” she laughed and led him through the house into her bedroom.

Angie had unwrapped all of last week’s purchases and they were laid out on her bed; Malcolm get excited just looking at them and gulped down his drink. Angie went to fix him another.

“I’ve been thinking Malcolm; how serious are you about looking as feminine as possible?” she called from the lounge.

“I really want to win the prize Angie; I want to really make up for last year,” he shouted back.

Angie returned with a drink for both of them.

“Well there is only one thing for it then,” she said and reached into a draw in her dresser and held out a pink plastic object that looked like some sort of alien ray gun.

“It’s my Lady Shaver,” she responded to his quizzical look, “were shaving your legs ok?”

Malcolm was now a little drunk and laughed out loud,

“Well if that’s what it takes Angie; let’s do it!”

After a brief argument in which Angie explained that she had seen her younger brother naked when she bathed him as a child.  She also went on to explain that in her eyes seeing a man in his briefs was no different to seeing a man in his swimming costume so Malcolm stripped down to his briefs and sat on the chair in front of the dressing table.  Angie ran the shaver up and down his legs until they were hairless; this was achieved with much howling and complaining from Malcolm who was reminded by Angie that women had to suffer far worse to look good for men; as he was about to find out.  She shaved the hair off his feet and toes and examined her handy work.

“You’ll still have to wear the pantyhose I’m afraid; your legs are lily white and some of those varicose veins look like roadmaps. It’s a trick I used when I was younger when I couldn’t be bothered shaving my legs before a date; just wear two pairs of nylons,” Angie explained.

“You’re the boss,” Malcolm chuckled and took another sip of his drink.

“Ok; sit still, keep quiet and just do as I say and we’ll have you looking like a girl in no time,” Angie laughed and moved in front of him and went to work.

She had quite an assortment of cosmetics laid out on the dressing table along with various sized brushes, sponges and applicators.  Malcolm forced himself to relax and let Angie go to work.  He had made himself up hundreds of times before but now he was going to be made up by an expert so he payed attention to every detail so that he could pick up any pointers.

First Angie patiently painted his finger and toenails; two coats of glossy plumb red.  She told him not to smudge the nail polish before it hardened and went on to explain how women often tried to match their nail polish with their lipstick.

Angie applied a thick coat of foundation to his face and neck and then set it with a liberal dusting of matching face powder.  She then went to work on his eyes.  Next she brushed dark blue eyeshadow onto Malcolm’s eyelids working from the inner corner of each eye to the centre above her pupils. She worked the powder upwards right up to his eyebrows and then she applied a coat of lighter blue out to the far corners of his eyes, lightening the makeup as she worked it up to his brows and blending the two shades where they merged.

“I’m no expert at hooker makeup,” she said, “but I’ve seen enough movies to know that usually go for these garish colours.

“Whatever,” Malcolm said pretending to feign interest whilst paying close attention.

Angie tut-tutted a little and reached for some pink eyeshadow and applied it liberally around the edges of the two coats of blue that she had already applied; blending the eyeshadow with a small brush and making final adjustments with her fingertip.  Malcolm loved the effect and filed the snippet away for future use.

“Ok brother; keep very still now and just close your eyes half-closed for me; here comes the hard bit; the eyeliner.” She said, concentrating on her task.

Angie applied jet black eyeliner to his upper and lower eyelids as close to his lash-line as possible. She started in the very corner of her each eye and worked outwards applying three coats and touching up where necessary so that his eyes were framed by the black makeup.

“Open your eyes; lift your head up but look down at my tummy and keep still for me sweets ok; I’m going to do your mascara next.  I hope you are taking mental notes so that you can touch up your makeup during the evening.” Angie said.

“What do you mean; touch up my makeup?” he asked; knowing full well what she meant.

“We girls don’t stay looking good all night without touching up our war-paint you know” she giggled, “that’s why we spend so much time in the john; why do you think we call it the powder room!  I bought you some makeup yesterday that you can take with you tonight; you can give it to me later as you won’t be needing it,” she explained.

She applied plenty of thick black mascara to his upper and lower eyelashes; fiddling a little as she worked.  She explained that as his eyelashes were very fine she had to apply lots of the product to get a good effect,

“I wish we had bought falsies,” she muttered.

Malcolm laughed inside because he had three sets of false eyelashes at home.

“Ok nearly there,” she sighed and took a sip of her drink.

Angie applied blusher to his cheeks, feathering it along his cheek-line and smoothing it up so that it almost merged with his eyeshadow.  Then she dusted his whole face and neck with a coating of sheer-glow finishing powder, being careful not to smudge her mascara and eyeliner.

“Ok Malcolm I want you to play particular attention to how I do your lipstick; you will definitely have to touch up your lippy tonight,” she lectured.

She opened a long slim box that contained two slim tubes and unscrewed the first tube to reveal a slim applicator coated with plum coloured liquid lipstick.

“This is the first coat and it is long lasting colour; be careful how you use it honey because it is really hard to get it off if you fuck up ok?” she instructed, “so pay complete attention and when you touch it up tonight make sure you don’t go outside of the lip-line that I put on you.”

Malcolm had never used a two-coat lipstick before; he just used ordinary cheap lipstick at home and he paid very close attention as Angie coloured his lips with the first coat of colour and then took the other tube which she screwed at the bottom to reveal what looked more like the lippy he was used to, but slimmer and it was clear not coloured.  She waited a minute and then applied the clear top coat over the base colour coat.

“Perfect,” she whispered more to herself than him, “now leave your lips parted for a second until its dry ok?”

Angie took the brunette wig off the wig stand and brushed it out while Malcolm sat still and let his makeup set and lipstick dry.  After a minute or two Angie put the wig on his head and fiddled with it until it was sitting perfect with the fringe straight.  She brushed it here and there and then stood back to admire her work.

“You look stunning; take a look,” she said, pointing to the mirror.

 The transformation was astounding; from a plain, smooth-faced man he had become a heavily made-up middle-aged whore.  Her brunette fringe framed her dark exotic eyes and her bangs caressed her rouged cheeks and highlighted her luscious red mouth.  Malcolm now started to think of himself as Michele the whore; not as Malcolm, the boring manager of a small department in a small business.  ‘From now on, for the rest of tonight, I AM Michele!’ she convinced herself.

 

“Ok let’s get you dressed then,” Angie said.

 

“You can have a quick drink and get into your pantyhose and knickers you hussy,” she laughed, playfully kissing his cheek.

 

“I’ll step out and freshen our drinks while you do that I think; I don’t want to see your wiggly bits,” she laughed, “put the pantyhose on first then the panties over them ok?  You’ve seen one of your girlfriends put on pantyhose I take it? You don’t need my advice,” she joked; then added as she walked out the door, “don’t ladder the fucking things!”

Michele sat on the edge of Angie’s queen size bed and kicked off her men’s briefs; they now seemed ugly and inappropriate for a lovely whore like her. She eased the pantyhose from the slim packet and slipped the hosiery over her pretty painted toes and slid the sheer nylon up her feet one foot at a time.  She carefully eased the pantyhose up her legs keeping the nylon taught; smoothing out the wrinkles as she went.  She stood up and pulled the waistband of the pantyhose up over her crotch and smoothed the nylon gusset around her midriff to just below her bellybutton.  She slid the red satin bikini panties up her nyloned legs and pulled them snug around her arse and crotch. Michele felt the beginnings of an erection and nearly panicked; but then the though of her sister finding her aroused soon made it go away.

“Ready sis;” Michele called through the door.

“Oh lovely,” Angie joked as she came back into the bedroom with two more gin and tonics.

“Ok let’s get a move on, I don’t want you to be late for your own party,” she said in determined tone.

“Stand up and just do as I say buster,” she joked; but in a tone that bore no argument.

Angie took the red lace suspender belt and adjusted it so that it sat tightly around Michele’s waist and so that the top of garment covered the waistband of the pantyhose.  Next she knelt down and drew the diaphanous black nylon stockings up Michele’s legs one at a time; the stockings sighed their nylon on nylon whisper as they glided over her pantyhosed legs.  Angie carefully adjusted the back-seams so they lay straight and centred along the back of Michele’s legs and then clipped the garters hanging from the suspender-belt to the reinforced stocking tops.  As Angie smoothed the nylons along her legs Michele suppressed the shiver of excitement and felt a little uneasy about experiencing such emotions; especially with her sister’s face so close to her sex organs.  Michele swallowed and tried not to think too much into it. 

Next Angie hooked the brassiere around Michele’s chest and settled the cups into the right position; she walked over to a drawer and took out several pairs of old pantyhose which she stuffed into the cups of the bra to fill them.  Then she had Michele step into the black leather mini which she pulled at and played with until it was adjusted nicely at the waist and the hem was nice and straight at mid thigh; she left it unzipped for now.  Angie handed Michele the leopard-skin nylon blouse to put on while she went to the dresser and took a drink.  She gave Michele a sip of her own drink and put the glass down on the table.  Michele noticed that she had not left any lipstick on the rim of the glass as she often did when she was dressed at home. ‘That two-coat lipstick really works,’ she thought pretending to struggle with the buttons because they were on the opposite side to men’s shirts.  Angie came over and finished buttoning the blouse and tucked it into Michele’s skirt and zipped it up. She buckled the slim gold belt around Michele’s waist and adjusted it so that it sat nicely.

“Nearly there; just jewellery and shoes to go” she sighed.

Angie opened the packet which contained the cheap costume jewellery that she had bought for her brother last week. She clipped silver mounted ruby drops to Michele’s ears and hung a matching silver and ruby necklace around her neck and matching bracelets on both of her wrists.  She put on four large silver rings, two on the fingers of each hand; the rings were set with emeralds and rubies. 

Angie sat Michele back on the bed and slid her feet into the black leather high-heeled sandals; buckling the thin straps which came to just above Michele’s ankles. 

“Now for fuck sake be careful when you walk in these Malcolm,” Angie said; “ lean a little forward and make sure you come down on the balls of your feet first, not the heels, when you walk.  It will take some practice but it’s only for one night.  You should know what we girls have to put with when we wear those fucking death traps anyway,” she chided playfully.

Finally Angie fastened a silver anklet below Michele’s left ankle; another fake ruby glittered as it hung from the thin silver chain fastened to the anklet.

“You’re done honey; take a look in the mirror,” Angie said and helped Michele to her feet. Michele stood up and walked over to the mirror and looked at herself.

She looked stunning; the best she had ever looked dressed as a woman.  She had just the look she wanted; in her mind she decided the look was to be called ‘London streetwalker’ because she looked just like the English prostitutes she saw in the TV shows.  Michele walked over to her sister and kissed her on the cheek and said,

“Thanks Angie; you are a doll.  Oh! One more thing; pin this on for me will you?”

She handed Angie a large white name bar embossed with the firm’s logo in one corner and a Christmas tree in the other; in gold pen script in the centre of the name bar was written: MICHELE NYLONS.  Angie pinned the badge to Michele’s left breast.

“Michele Nylons; cute name,” Angie said.

“Ok Malcolm; err I mean Michele; lets do the last finishing touch.”

Angie went to her dresser and took a small green bottle of the cologne ‘Poison’ and sprayed a liberal amount of the perfume on Michele’s neck and décolletage; then she reached down and playfully sprayed under Michele’s skirt and on her thighs.

“Just in case you get lucky honey,” Angie teased.

Michele blushed a deep red,

“Fuck off Angie!” Michele responded a little hurt.

“Don’t be such a girl Malcolm; here take this,” she said dropping the small bottle of ‘Poison’ into the small gold clutch purse that they had purchased last Friday and holding it out.

“The purse has got powder, eyeshadow, mascara, eyeliner, blush, and lippy in there sweety; so you can touch up your makeup as you need to.  There’s also a hairbrush; everything an old whore needs to ply her trade,” she laughed.

Michele stepped forward and took the purse from her sister and bent to kiss her chastely on the lips to bid farewell.  Angie shocked Michele by pulling her into a tight embrace and kissing her, closed mouth but forcefully, on the lips; then Angie astonished Michele completely by sliding her hand under Michele’s skirt and gently stroking her manhood through her panties.  Angie whispered into Michele’s ear,

“I know about you, you know!”

Michele pushed her sister away and looking absolutely stunned; she gasped,

 

“What do you mean; you know!”

 

“Oh Malcolm; I mean Michele.  I’ve suspected since we were kids.  All the times I found my nylons and panties dishevelled and stained; who else could it have been?  One day I even saw you putting a pair of my pantyhose in your pocket as you left the bathroom.” Angie explained in a soothing voice.

 

“And last week you knew your ladies shoe size; you insisting on wearing a suspender belt; you had those pictures of Transvestites; and you pretended not know that blouses button on the opposite side to shirt.  You sat uncomplaining while I put on your makeup; but the real give away was the way you walk in those high heels honey.  It took me fucking months to master high heels when I was a teenager; and you glide around my bedroom like you were born wearing the fucking things!” Angie finished.

 

“It’s nothing to be ashamed of; your secret is safe with me.  And you look positively gorgeous; if you weren’t my brother I’d fuck your brains out; now get the fuck out here and go and enjoy yourself before I throw you on my bed and ravage you.” Angie pushed Michele towards the bedroom door.

 

Michele was stunned but accepted what she had just heard and realised that she had been stupid to think that she could get away with using her sister to help her crossdress and still keep her secret.  In hindsight Michele knew that she would slip up some how.  Then a question lanced into her head; ‘What did Angie mean about ravaging her? And what the fuck was that passionate kiss and quick fondle all about?’

 

“Angie; are you a lesbian or something?” Michele asked her sister as they walked to the front door.

 

“I’m an ‘or something’ ok; but that’s a conversation for another day; now get the fuck out of my house and party til you drop bitch! Oh; and come around for coffee tomorrow afternoon and tell me all about it!” she laughed and pushed Michele out of the door and into the night air.

 

Michele walked over to her car, stunned at what had just happened; even though she had lost count of the number of gin and tonics she had drunk over the last few hours she now felt completely sober.  She dropped in behind the wheel and her skirt rode up revealing her stocking tops; she smoothed down her skirt and slid her hands along her stockinged thighs and sighed with desire at the feel of her feminine attire.

 

Michele smiled to herself and drove off into the night trying to get her head around the last few minutes.  Eventually she settled down enough to realise that she had been particularly stupid drinking so much alcohol with a three quarter of an hour drive ahead of her from the suburbs to the city; the police were ruthless when it came to alcohol breath testing during the festive season.  She decided to use a little used back road that bypassed most of highway into town; it would put an extra twenty minutes or so onto her journey but she was better safe than sorry.

After she had driven a few kilometres down the dark road she realised that the effects of the drinks she had imbibed earlier had far from worn off; she had to really concentrate and to make matters worse she had never considered the difficulties of driving a car whilst wearing high heels.   Michele checked her mirrors and then reached down and attempted to unbuckle her right shoe so that she could better control the brake and accelerator.  It was a huge mistake; as she struggled with the buckle on her high heel her car swerved violently to the right and she had to correct the vehicle quite quickly on the dark narrow road.  As she gained control of the car and was congratulating herself for avoiding disaster she saw blue and red flashing lights in her rear vision mirror.

“Fuck!” she exclaimed, and pulled her car over into a darkened rest area at the side of the road. 

She followed the small dirt track to series of marked parking bays behind a darkened toilet block and pulled into one of the spaces; she looked around and saw that the rest area was deserted except for her own car and the police cruiser that had now pulled up beside her.  A fat policeman squeezed from behind the wheel of the police car, turned on a large black torch and sauntered over to her driver’s side window; Michele wound down the window terrified.  She didn’t know wether to be more worried about being out dressed up in drag or being over the prescribed alcohol limit.  The fat policeman shined his torch on her face, smiled and said,

“You were all over the road back there miss; have you been drinking?”

Michele summoned up all of her courage and answered,

“I had a couple of drinks an hour ago officer but I’m sure I’m under the limit; I swerved to avoid a small animal on the road,” she lied.

The policeman looked at her for a nearly a full minute shining his torch inside the car and up and down her body and back to her face.

“Jesus Christ you’re a fucking guy aren’t you?” he asked incredulously.

“Yes officer; let me explain…….” and Michele went on to explain that she was dressed in drag to attend a theme party at work.

After listening to her story for a few minute the officer cut her short.

“Well that may be sir, ma’am; whatever.  But I still think that you are under the influence of alcohol and I intend to issue you with a roadside breath test.” He said and waddled back to the cruiser and returned with an alcometer.

He pushed it through the window in front of Michele’s face and said,

“Put your lips on the tube and blow; words I’m sure you quite used to;” he added cruelly.

Michele did as she was told and heard the machine beep rapidly after a few seconds.  She hung her head and contemplated what would happen next.  She would be taken to the police station and have to suffer the indignity of waiting around for bail dressed up in drag.  Undoubtedly the policemen at the station would ridicule and taunt her.  Even worse; what if they put her in a holding cell?  She had read about what happened to some young men in prison at the hands of jailhouse thugs; what chance would she have dressed as she was?  Could she ask for protective custody?  Her head was spinning.

The Policeman took the machine away from Michele’s lips and looked at the reading and smirked.

“You’re shit out of luck tonight sweety,” the cop smiled evilly at Michele through the window.

He turned on his heels and wobbled back to his cruiser; ‘He’s calling it in or whatever they do!’ Michele thought to herself.  She was on the verge of sobbing.  She looked across at the police cruiser and by the light of the dome light she saw the fat cop leaning inside talking on the radio.  Then the flashing lights on the top of the police car went out, closely followed by the head and tail lights.  The cop slammed the door and the rest area became hauntingly dark and deathly silent.  Michele could just make out the dimmed glow of the policeman’s torch as he returned to her car; as he approached she saw he was shading the light with his other hand.  He leaned on the roof of her car and it lurched under his added weight.

“Look honey, I’ve dealt with your type before ok; you don’t do thirty years on the force without dealing with the occasional trannie now and then.  You are in all sorts of problems here; the reading on my little machine there says you’re at least twice the legal limit to be driving.”

“Now, we can sort this out one of two ways; you can accompany me to the police station, and I’m sure the ramifications of that option have crossed your pretty little mind; and also you will lose your license and cop a hefty fine.  Plus I’m betting someone who drives a car like this has a job where a DUI will not be particularly welcomed,” the fat cop droned on.

“Or I can get in the passenger seat there and we can settle this quickly, painlessly; and to both our advantages if you know what I mean?” he finished.

Michele was now totally confused; was there a way out of this?  Was he asking her for a bribe?  Thank god! There was a way out of this! All she had to do was let the cop get in passenger seat and she would hand him some cash and he would be gone.  Yes; it made sense!  He wanted to sit in the car so no one passing by could see her handing him the money; that’s why he turned off his flashers and headlights.

“Well sure officer; get in and let’s settle,” Michele sighed, relieved.

The fat cop had trouble squeezing into Michele’s small BMW but he finally got settled and closed the door.  The dome light went out and Michele heard a rasping sound that she couldn’t quite figure out.  ‘Of course he’s opening the zipper of his wallet to hide the money,’ she concluded.

“Turn on the dome light honey; I want to see you do it,” the cop said.

That made sense to Michele; he wanted to make sure he was giving her the right money; when you take bribes you have make sure the person paying the bribe isn’t ripping you off.  Michele turned the dome light on and turned her head towards the cop and started to say,

“How much?” when she glanced down and saw the policeman’s stubby fat penis sticking out the front of his uniform trousers.

“Well I won’t be long honey; I haven’t had any for ages,” the cop chuckled and reached out and pulled her head into his lap.

Michele was horrified; it finally dawned on her what he had been talking about all this time; she had completely misunderstood his intentions.  These thoughts sped through her mind just as her lips came into contact with the man’s fat smelly cock.  Michele sputtered and tried to move her head but the heavy cop held her down.

“Suck it good babe; come on,” he moaned; and he pushed down harder and Michele had no choice but to take the appendage into her mouth.

Michele sputtered and blubbered trying to spit the fetid member out of her mouth.  Her efforts to get away from the cop’s penis in fact stimulated the glans of his organ as Michele’s lips and tongue lashed at the stubby little cock trying to spit it out.  The cop pushed down so hard on her head that it hurt, and at the same time he pushed upwards, lifting his fat arse out of the seat; Michele had to open her mouth or choke and as she did the whole of the diminutive fat member slid inside her mouth and started to convulse and throb.

Michele gasped as a torrent of semen filled her mouth and then she started to gag.

“Don’t you spit it out bitch!” the cop warned, holding her head down in his lap.

“Yeah baby that’s it; swallow it; oh fuck you’re good! Suck it baby; suck it! I’m coming; oh yeah,” another stream of obscenities issued forth from the policeman as he ejaculated into Michele’s mouth.

Michele was helpless; held over the cop’s small throbbing cock as it continued to flood her mouth with sperm.  She had no choice; Michele swallowed.  The policeman’s secretions were not actually that foul; they tasted musty and creamy.  She sucked and swallowed knowing she had no choice.

“Ok baby; daddy’s finished now; just lick it clean and I’ll be on my way,” the cop chuckled.

Michele realised the worst was over; she licked the fetid member clean and swallowed the last of the cop’s secretions.  The cop lifted Michele’s head out of his lap and leaned over and kissed her full on the mouth before she had time to react.

“Thanks hun,” he whispered in Michele’s ear; then zipped his fly and struggled out of the passenger door.  He walked away towards his police car and waved over his shoulder without glancing back,

“Drive careful now sweetheart,” he shouted and climbed into the police car and drove away.

Michele sat there stunned; she couldn’t believe what had just happened; not only had that fat smelly, little dick cop raped her mouth; she was rock hard in her panties.  What the fuck was going on?

To be continued………………………………………

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

The predator had defiled five women so far, all sophisticated, attractive and well dressed ladies in their forties or early fifties. He made a point of that; that they be dressed attractively. He had been known to make his victims get out of bed and apply makeup and dress in their finest lingerie and eveningwear before he spent his time playing his sordid games with them. Some victims reported that he made them parade before him wearing differing ensembles until he was satisfied with how they looked before he ravished them.

The predator had arrived at his current destination by sheer luck. He usually followed his intended victim for a few days, and then planned his attack when he was sure that the victim was alone in her home. Tonight he was returning from a bar and decided to cruise a well-to-do neighbourhood just to see if there was anything special that might be worth following up. He was slightly drunk and stopped his car next to an alleyway separating two townhouses so that he could relieve himself. He ducked into the darkened alley to urinate when he noticed the shadow on blind. The silhouette on the blind was unmistakeable to a predator of his kind; a woman either dressing or undressing; her movements and mannerisms playing out like a shadow-puppet on a movie screen. He couldn’t help himself; he had to see what might be on offer here. When he had splashed the last of the hot stream of his urine against the wall he climbed up onto a garbage bin hoping he would be able to see more through the window.

The predator was in luck and managed to secure a position where he could see through a chink in the blind where it had not been fully extended. The view provided by the chink took in half of a woman’s bedroom. He could see most of the bed, scattered with lingerie and women’s clothing lying in a heap, the coat-hangers still attached to the skirts, blouses and jackets. There had to be at least six outfits lying on the bed surrounded by the small piles of assorted lingerie. He could see a dressing table littered with makeup, perfume bottles, jewellery boxes and the sundry items that women seemed to be unable to do without in their endeavours to look attractive. A wine glass, half full of red wine was set to one side. A small shelf above the dressing table held three wig stands. A blonde bob sat on one wig stand and a black long haired wig sat on the second; the third wig stand was bare.

The predator was pleased to see that this woman had such good taste in clothing and obviously looked after herself. The mountains of lingerie, makeup, jewellery and the wigs bespoke of a woman who was most attentive to her appearance – the sort of woman he fantasised about.

The predator allowed his eyes to consume the sight before him. The woman presented herself sideways to him, sitting in front of the mirror at the dressing table making final adjustments to her appearance. She looked to be in her early forties, solid but not fat, and dressed just to his taste. His eyes started with her face and worked their way down her body. Straight brunette hair hung just to her shoulders, the fringe framing her heavily made-up eyes; her cheeks were rouged, her lips full and painted plum red. A glint of light betrayed the simple sparkling earrings that undoubtedly matched the diamante necklace around her neck. She was wearing a black nylon full-slip, the rise of her small breasts emphasised by the tight bodice, the laced hem of the slip resting on her sleek nyloned thighs just above her knees.

The predator liked the way her taupe stockings glistened in the lights from the makeup mirror. Her hands slid down one leg, her fingernails painted a matching plum red to her lipstick, and adjusted her stocking; pulling the sleek nylon taught on her shapely leg and momentarily disappearing under the hem of her slip as she adjusted the clip on a garter strap. The predator shuddered. His eyes continued down her leg and lingered on the black, patent leather, open toe high-heels and he caught a glimpse of her painted toenails on display, encased in the gossamer of her sheer stocking, as she waggled her foot back and forth back as the admiring her own pretty foot. She stood, and then advanced towards the bed presenting herself front-on to the predator.

The predator took in the whole visage of the woman that he had now determined was to be his next victim. Mature, attractive, heavily made-up, tall and well built; she was just to his taste. If he had not spent the evening in the bar and was in a sober frame of mind he might have been more cautious, but the sight she unknowingly presented to the predator sealed the woman’s fate. The predator slid silently off the garbage bin on which he had been standing and made his way back to his car. He scanned the street and saw no one. Most of the lights in the adjoining townhouses were out and the street was quiet. He checked his watch: 11:30pm, perfect he thought, and reached into the back seat and took out his burglary tools. Fuck the risk! He had to have her. Now!

Michele sat before the makeup mirror twirling the wine glass in her fingers watching the light sparkle in the red Shiraz. The dark red wine matched the colour of her fingernails and she briefly giggled to herself at the complement. She was slightly drunk from the half-bottle of wine she had already consumed and she set the wine glass down carefully and began to add the final touches to her makeup.

Michele was actually Michael, a divorcee in his mid forties who lived alone and had come to transvestism late in life after suppressing an urge to crossdress for most of his adult years. Like most crossdressers he had urges to dress-up and become a woman for short periods of time and often dressed in his wife’s underwear when she was away. After an amicable divorce some five years earlier, Michael now transformed into Michele whenever it pleased him to do so. Living alone and having the privacy to dress when it suited him, he had developed the persona of Michele over a period of years.

Michele’s male alter ego had fought a battle with his weight for most of his life and he had allowed himself to balloon out during the later part of his marriage. When the opportunity to fully crossdress whenever he felt like it presented itself, Michael decided he didn’t want to look like a middle-aged frump. He dieted and exercised until he could eventually fit into a size 16 and some times even a 14; a great effort given his large frame, and he now carried very little fat.

Michele had acquired an extensive wardrobe, first at opportunity shops and later at larger specialty shops; insisting to the shopkeepers that he was buying the clothes as presents for his wife. Lingerie was easy to buy as it is never considered unusual for men to buy nice underwear for their wives or lovers.

Michele bought his first pair of women’s shoes from an opportunity shop and once he knew his woman’s shoe size he purchased many styles of high-heeled pumps and sandals; again insisting to inquisitive shop assistants that they were presents for his wife. He sometimes had the boxes gift-wrapped to maintain the façade.

Michele had dabbled with his wife’s makeup with various degrees of success and failure during the years of his marriage and easily obtained all the makeup he needed by purchasing a couple of complete makeup kits ("its for my niece’s birthday; she’s just turned thirteen") and then simply added to his makeup collection by throwing any item he desired in with the week’s groceries; no one ever questioned him at the checkout; husbands just picked up whatever their wives had written on the shopping list after all.

Michele could purchase women’s jewellery easily of course, but his biggest problem was how to get his hands on some nice wigs. The problem was solved when he was sent to a large city interstate on a business trip where he visited the part of town frequented by the gay community. Here a sympathetic old lady in a wig shop who was used to dealing with ‘his kind’ helped him pick out and try on three different styles and hair colourings. He purchased the wigs and then went into another ‘specialty shop’ where he bought breastforms in two sizes.

Michele loved being Michele; Michael transformed into her at every opportunity and spent most evenings and weekends dressed and fully made-up. More and more often though he had been fantasising about taking his transvestism a step further; whenever he was dressed as Michele he became aroused, he always had, but for the last year or so he had fantasised about being with a man. He did not consider himself gay; in fact when he wasn’t Michele his sexual fantasies revolved around women; but when he was Michele he wanted to be with a man or to have a ‘lesbian’ encounter with another transvestite.

Michele was terrified that her secret life would be exposed. When dressed she kept the doors locked, the shades closed and never answered the door. Although she had become adept at applying makeup and dressing en-femme, and she believed that she made quite an attractive mature woman, she would never dream of going out dressed as Michele. She contented himself with reading books and looking at magazines and movies where transvestites had hot sexual encounters with each other and with male admirers. Although masturbation bought relief, Michele longed for ‘the real thing.’ She was thinking a lot lately of either placing a discreet ad in some of the sex shops she visited or advertising her availability in a contact magazine or in some of the internet chat rooms she frequented.

Michele was not aware that she was about to have her first encounter tonight, nor that the Predator would be her first man. The Predator was not aware that the woman he lusted after, as he spied on her through her bedroom window, was in fact Michele; a transvestite.

Michele had opened a nice half-bottle of Shiraz earlier in the evening and then poured herself a warm bath. She painted her toe and fingernails and allowed them to dry and then poured herself a glass of wine and stepped into the steaming, scented water. She spent a luxurious hour soaking, during which she had shaven her legs and chest and closely shaven her face. She had also drunk three glasses of wine.

Michele towelled herself off and carried a full glass of wine from the ensuite bathroom into her bedroom where she sat at her dressing table and looked at herself critically in the mirror. She was showing her age but was still respectable and with the magic of makeup would soon be transformed into a presentable, if slightly sluttish, middle-aged woman. She giggled to herself and realised she was slightly drunk.

Michele went through the labour of applying her foundation; she had a product from Max Factor which closely matched her skin colour but covered up the few scars and blemishes that she had acquired during in her life. Next she liberally coated her face and neck with face powder one shade darker than her foundation; she now had the blank canvass she liked to achieve prior to applying the rest of her makeup. She loved this next part; the application of colours and shading which changed the whole look of her face from bland maleness to feminine fox. She giggled again and took a gulp of wine before continuing.

Michele applied her eyeliner next. All the books and magazines in which she had read makeup tips said you should do this later but Michele had learned that this was the hardest part of applying makeup and if she screwed it up (which she often did, especially after drinking), she could wipe the eyeliner away, apply more foundation and start again without ruining her eye-shadow and mascara. The eyeliner was applied liberally to her upper and lower eyelids, from the inner corner of her eyes to the outer corners, gradually thickening the line as she went. Having achieved the desired result she looked for a suitable palette of colours for her eye-shadow.

Michele selected a pale blue which she applied to her eyelids and then blended it into a shade of dark pink which she brushed onto the upper part of her eye sockets and right up to her eyebrows. She wished she could shape her brows but that would be too noticeable to her workmates, family and friends so she just kept her brows neatly plucked. Next she rouged her cheeks to define the lines of her cheekbones. She used more rouge and eye-shadow than is the fashion nowadays but she preferred the more colourful makeup styles of the eighties over the current subdued ‘less is more’ look.

Michele next applied a light coating of ‘skin-glow’ face powder all over her face and neck to set the makeup she had already applied and to give her face a subtle radiance. She carefully brushed lashings of mascara onto her lower and upper eyelashes. She knew from painful experience that if she put too much mascara on her lashes that it would congeal and look unsightly; even worse it could end up ruining her eye-shadow or face makeup if globs of the mascara came loose from her lashes. She did like to wear lots of mascara though and found a Maybelline product that did not clot and was easy to apply.

Michele took her time putting on her lipstick. Having completed the rest of her face she didn’t want to ruin the effect with a sloppy job. She took time to line her thin lips just outside her lip-line so that her lips would seem fuller; she also knew that the wine she had drunk was having its effect and realised that caution here would save her tears of frustration if she slipped and made a mess of her lipstick. The colour was a deep plum red and matched the nail polish that she had painstakingly painted on her toe and fingernails prior to her bath.

Michele reached up and studied the three wigs sitting on their stands. ‘The brunette,’ she thought to herself and lifted the wig from its stand. She brushed the wig with the special brush that she been advised to purchase by the nice old lady who had sold her her wigs. She started her brush-stokes at the extremities of the hair and worked her way up to the crown, admiring the sheen of the artificial hair. She positioned the wig on her head and adjusted it so that her fringe was straight and hung level with her eyebrows.

Michele looked in the mirror and admired her transformation. ‘I look quite attractive’ she thought; ‘I bet Michael would like to fuck me’ (she giggled to herself at the absurdity) and reached for her wine glass.

Michele went to the closet located on the right-hand side of the bedroom; Michele’s closet. The closet on the left was Michael’s closet and contained his suits, shirts, ties and boring male underwear, socks and shoes. Michele’s closet contained the soft, luxurious, feminine attire that so excited her. She rummaged through the lingerie draws and threw a pile on the bed; next she took down half a dozen ensembles and threw them in the centre of the bed amid the strewn underwear. It looked like a messy, awkward way to select an outfit but it worked for her. She would often get nearly fully dressed and then change her mind and she had found over the years the best method for her was to take a selection of clothing and throw it on the bed and then once she had finished dressing, put away whatever clothing she had decided not to wear.

The predator at this time was just leaving the bar having been unsuccessful in locating a suitable woman as his prospective next victim. He had drunk more than usual, and frustrated at not finding his next target, stumbled to his car and took off towards the better part of town to prowl for a fitting quarry to stalk.

Michele tore open a packet of cheap flesh-toned sheer to the waist pantyhose. She wore pantyhose as a foundation garment to help flatten her tummy, hold her male genitalia out of the way between her legs, and to help cover the small nicks and varicose veins on her forty-year-old thighs and ankles. She felt a small tingle of excitement as she smoothed the pantyhose up her legs and over her tummy and buttocks. She carefully manipulated the sheer toes around her painted nails ensuring she didn’t ladder the cheap hose.

Michele selected a pair of red nylon full-cut panties from the midden of lingerie on her bed. She stepped into them and slid them up her nyloned thighs, savouring the rustling sound of nylon on nylon. She adjusted the waistband on her hips so that the cute little lace bow was centrally located below her belly button. Michele could not understand the modern woman’s obsession with thong panties; they were uncomfortable and unflattering on women of her solid build. Besides she liked the way the tight nylon panties caressed her buttocks.

Michele next chose a black satin garter belt; her mother had called them ‘suspenders’ she remembered. She clipped the garment together and stepped into it carefully pulling it up her hosed legs and over her panties so that it sat snugly around the bottom of her waist. She carefully adjusted the garter straps ensuring they did not snag her pantyhose.

Michele decided on a matching black satin bra, again clipping the fastenings at the back of the bra together before donning the garment. She giggled yet again when she thought about all the troubles she had had as a young adolescent Michael attempting to undo his girlfriend’s bra so that he could caress her budding teenage breasts. She took another sip of wine and pulled the garment over her head, adjusting it on her chest in the mirror and straightening the straps on her shoulders. She had breastforms if she wanted to use them but this bra was slightly padded and with her ‘man boobs’ gave her a pleasing if subtle cleavage without being overly busty (although sometimes, when she was in the mood, she liked to stuff her bra with the largest set of breastforms she had and parade around like Mae West).

Michele dithered over which stockings to wear; it would depend greatly on which ensemble she finally decided upon. Should she wear black, grey, taupe, flesh-toned; fully fashioned, Cuban heeled or sheer toe? She had so many pairs! She settled on a pair of high sheen taupe lace tops. She loved the way they emphasised her shapely legs, and with the flesh toned pantyhose underneath the stockings, her legs would look magnificent. Michele thought her legs were the best part of her body. She slid the stockings on and connected the clips on the garter straps to the lacy stocking tops. She reached for her jewellery box and selected faux diamond earrings and a matching pendant necklace. As she clipped the earrings to her ears she lamented the dearth of good quality clip-on earrings. She dare not pierce both her earlobes as it would be too noticeable to others.

Michele went back to her closet and selected a pair of black, patent leather, open toe high-heels and placed them beside the chair next to her dresser. She chose a black nylon full-slip from the mess of lingerie on the bed and pulled it over her head being careful not to ruin her makeup or hair. She smoothed the garment to her body, the tight bodice clinging to her breasts and hips and the skirt flaring around her thighs, occasionally sticking to her stockinged legs because of the static electricity. She loved the feel of the lacy hem; like butterfly wings brushing on her thighs.

Michele sat down in front of the dressing table and slipped her feet into her high-heels; although a size eleven her feet were not grotesque because they matched the proportions of her body. After all she was a small size eight in men’s shoes and her feet were considered quite small for a man. She turned her chair sideways to the dresser so that she could adjust her stockings; she pulled the sleek nylon taught on her shapely leg and her hand disappeared under the hem of her slip as she adjusted the clip on a garter strap. She waggled her right foot from side to side, admiring her own pretty feet in the high-heels and appreciating the gleam of the lights on her high sheen stockings. Little did she know that she was not the only one admiring her legs and feet!

Michele stood and advanced towards the bed to select an ensemble for the evening. She finally decided on a white ‘Carla Zampatti’ A-line skirt and a mauve satin long-sleeved blouse she had purchased from Supré. She always wore long sleeved blouses or jackets because although she kept her fingers and the backs of her hands free of hair, she could only lightly shave her arms with a beard trimmer. Her tanned arms had only a light sprinkling of fair hair but she felt that fully shaving them would be too noticeable when she wore T-shirts and Polo’s when she was Michael.

Michele donned the blouse, fumbling with the buttons; she was still not used to them being on the opposite side to men’s shirts. Then she stepped into the skirt and pulled it up around her waist, tucking the blouse into the skirt and closing the zipper at her waist. She went back to her dresser and mooched through the jewellery box and decided upon two matching silver bracelets for her left wrist and a silver amulet set with a large black opal for the right. She slipped a matching opal ring set in silver on the ring finger of her right hand and a diamante ring set in white gold on her left ring finger.

Michele pushed her hands out before her and admired the effect of the jewellery against her slim wrists and her plum-red painted fingernails; she had taste she thought, but she still projected that slightly sluttish style she favoured. She looked at herself in the mirror and was pleased with the result. She twirled around and admired her ample but well-proportioned bottom; the A-line skirt was a snug fit. She drained her wine glass and tottered on her high-heels as she started from the bedroom to the kitchen to open another bottle of wine. She was drinking a lot lately; but what did she care? As long as she kept her weight in check; it’s not as if she had a boyfriend to keep sober for. She sauntered down the hallway towards the kitchen, her heels clicking on the slate tiles as she did her best vamp imitation, swinging her buxom sexy bottom from side to side and giggled to herself again.

The predator had let himself in easily through the kitchen window whilst Michele was making the final adjustments to her clothing in the bedroom. The kitchen window looked out over a small garden, dark at night, and well hidden from the main road; the lock was cheap and easily defeated. The predator was silent as he climbed through the window and dropped soundlessly to the tiled floor; he’d had plenty of practice after all. He heard the clatter of high heels on the tiles and a little giggle from the hallway. ‘Oh this bitch would not be giggling for long!’ he thought, as he hid behind the opened door that led into the kitchen from the hallway.

The predator quietly lowered the bag containing his burglary kit to the floor and reached inside it to take out a gag and a pair of handcuffs. He didn’t like using the gag on his victims because it ruined their lipstick and distended their faces. He liked to look into their pretty faces while he did things to them, and once they learned resistance was futile (and they all learned that lesson pretty quickly) he liked to kiss them. The woman who had excited him enough to risk what he was about to do had affected him strongly; he wanted to take her as soon as possible, his member was so hard that it was uncomfortable in his pants. He would take her quickly in the kitchen and then they could retire to her bedroom for the rest of the evening’s entertainment. he thought to himself.

The predator heard her high-heels getting louder now as she approached the kitchen door and his drunken mind reflected on his last glimpse of her before he had jumped down off the perch outside her bedroom window. Her heavy makeup, the black nylon slip in contrast to her sheer taupe stockings (he preferred women who wore stockings instead of pantyhose), and those shiny black open-toe high heels. He would take her fully clothed, right here in the kitchen; he would take her in such a way that she would know he was in charge and that resistance was futile. He would take her in a way that a woman of her breeding had probably never experienced before.

Michele walked into the darkened kitchen and headed straight for the wine rack above the breakfast bar. She didn’t bother turning on the light as the light spilling in from the hallway was ample for the task; besides she hadn’t closed the curtains in here and even though her kitchen window was not in open sight of the road she was still paranoid about anyone seeing her dressed en-femme. She was thinking of whether to open a bottle of Shiraz or merlot when she felt herself being pushed heavily from behind and she collided heavily with the kitchen table.

The predator pounced on her when she was halfway across the room. He used his weight and strength to propel her towards the kitchen table. She was a big woman and he was taking no chances; as she crashed into the table he pushed her shoulders down and pulled her hands up behind her back and clamped the handcuffs on her wrists. He lifted his knee and slammed it into her well proportioned behind to hold her against the table and pulled up on her cuffed wrists. As expected, she pushed her upper body upwards and back in an effort to escape, but this only assisted him. As she rose up and gasped, a prelude to either to a scream or cry for help, he pulled the ball bag over head and into her mouth, securing the straps tightly around her neck. He now had her where he wanted her.

The predator pushed down on her shoulders so that she was bent over the kitchen table. In the dim light he could now see her mauve satin blouse and the white A-line skirt; subconsciously he approved of her style, he loved it when they dressed nicely for him. He wasted no time. The predator kicked her heels apart so that her legs were spread as far as the tight skirt would allow and released one of his hands from her cuffed wrists and undid his flies and released his erect organ.

The predator was extremely aroused and he could smell the stale alcohol on his own breath as he panted in excitement. He reached under the woman’s skirt with his free hand and grasped the waistband of her panties and yanked them down. He was puzzled when her panties came to an abrupt halt at the top of her thighs and then he realised that she was wearing her garter belt over her panties and because of this her panties could be lowered no further without releasing the clips on the garter straps attached to her stocking tops. It didn’t matter, her panties were down far enough for him to carry out his intentions.

The predator stepped in close between her splayed high-heeled feet; his crotch close to her buttocks, one hand gripping her handcuffed wrists and pushing her body down hard on the kitchen table, the other hand under her skirt pulling her panties down so that they bunched around her thighs. He bought his free hand out from under her skirt and spat in the palm of it; then he spread the glistening spit over his tumescent penis, ensuring his glans was completely lubricated.

The predator lifted the woman’s skirt up and thrust forward. His cock came up against a membrane of sheer nylon, and for a moment he couldn’t figure out what had happened. Was the silly bitch wearing two pairs of panties? Then he figured out what was preventing him from reaching the object of his desire; it was the gusset of the woman’s pantyhose. The dumb cunt was wearing pantyhose under her stockings! Why the fuck would she do that?

The predator took no time to try to answer these questions, he was now so stimulated that he was close to climax. He pushed forward with his hips and felt his member force the nylon membrane of the pantyhose into the crease between the woman’s buttocks. He pushed harder still and felt his glans nestle into the woman’s anal bud, her silken hose wrapped around the sensitive head of his penis stimulating it into bringing forth a trickle of pre-seminal fluid; the clear liquid combining with his spittle to further lubricate his member. He grunted and pushed forward with all his bodyweight and actually felt the heavy table move an inch or two as he thrusted.

The predator felt his iron hard cock tear through the gossamer thin pantyhose gusset and then slam against the woman’s tight sphincter. His cock paused briefly at her resisting puckered entrance, then his weight and the lubricant did their job and his shaft slid slowly and steadily inside the woman’s tight back passage. The Predator’s crotch slammed hard against the woman’s soft round buttocks and his scrotum rested in the silken purse of her bunched panties stimulating him to extremis. He ground his crotch in a circular motion against the woman’s lovely soft arse and pulled her back hard against him and unloaded stream after stream of hot semen into her tight channel.

The predator howled and shuddered as his orgasm shook through his body; he ground his hips harder against her and stimulated his scrotal sac by rubbing it against the silken gusset of her pantyhose. His climax over, he pushed the woman forward and pulled back from her. He watched in awe as a trickle of semen seeped out of her and ran down her thighs, staining her stocking tops and pooling in the crotch of her panties. He had only just started with this bitch; he was going to have some fun tonight!

Michele lost all thoughts of red wine as she was propelled forward and slammed hard against the heavy wooden kitchen table. She was confused as to what was happening; her thought processes slow and fuzzy because of the wine she had drunk. She realised a stranger was in her house and that she was being pushed down across her own kitchen table but couldn’t figure out why. For one second she stupidly panicked at the thought that someone had found her dressed as a woman; and then a split second later she realised that she had a lot more to worry about than the exposure of her transvestism. She realised she was in serious trouble when she felt the handcuffs clamp on her wrists.

Michele’s fighting instinct took over and she used all her strength to lift her body up off the table so that she could yell a protest to the man who was assaulting her. She understood now that the perpetrator believed he was dealing with a woman; if she could just let him know that he had handcuffed a man, not a woman, maybe the intruder would let her go, or at least think twice about what he was about to do. Maybe she could negotiate with the trespasser; offer him money, her car, anything to get him out of her house without any further indignity.

Michele never got a chance to say a word; as soon as she opened her mouth the rubber ball gag was pushed into it. She started to hyperventilate, being forced to breathe in and out through her nose; then her chest was slammed downwards on top of the kitchen table and she couldn’t move. She stumbled as her heels were kicked apart and her legs spread to the full extremity allowed by her tight skirt. The home invader held her tightly against the table so that she wouldn’t fall, and then terror struck her she felt his hand reach under her skirt.

Michele was horrified at the prospect of what was about to happen to her. A glimmer of hope surfaced; he would realise she was not a woman and let her go, surely! Then she felt him yank her panties down and was actually relieved when her panties entangled in her garter straps and would go no further. As soon as the pervert reached under her to touch what he thought would be female genitalia he would be in for a terrible shock. He would be shocked by what he found there and would stop what he was doing. He would be disgusted to find out that she was a transvestite and may even beat her, but at least he would stop this perverted attack.

Michele’s glimmer of hope faded when she heard his flies unzip and the sound of him spitting into his hand. She was about to attempt one last struggle when her attacker’s full weight pressed against her backside pinning her to the table. She screamed to herself in her head as she felt her skirt being raised and the gusset of her pantyhose stretch as her attacker’s penis nestled in the bud of the entrance to her back passage. The fool didn’t realise she wasn’t a woman! He thought she was the lady of the house and he intended to defile her in this despicable manner to gratify his primal urges! Then she felt her attacker’s hard hot member tear through her pantyhose and begin to invade her.

Michele screamed into the gag at the intense pain as the hot cock forced its way inside her. No sound would issue forth around the gag but that silent scream would live in her memory for a long time. The man’s member slid slowly but inevitably deeper and deeper inside her; surprisingly after the initial shock and intense pain she felt as he had entered her, the feel of the invader’s lubricated penis became less painful; it just felt uncomfortable and filling.

Michele felt the intruder’s crotch press hard against her soft buttocks and realised with some relief that he was now fully inside her. She felt him pull her soft bum back hard against him and the gyrations of his hips as he worked his turgid member around inside her tight passage. Then she felt the hot gush of his semen as he spent himself deep inside her; she heard his groan and could smell the stale alcohol on his breath as he bayed and howled with his climax.

Michele was absolutely astonished at what happened next. As her defiler’s glans pulsated and throbbed against her sensitive prostrate, washing it with his hot seed, she felt a stab of exquisite sexual pleasure pulse through her lower regions and she simultaneously stiffened and ejaculated into the crotch of her pantyhose. She couldn’t suppress the pleasure she felt even though she felt utterly debased. She collapsed against the kitchen table as her orgasm subsided and she felt her attacker pull himself slowly out of her and was surprised that it did not hurt but in fact was mildly pleasurable.

Michele could feel that the tight bud of her back passage was left slightly open after the ravaging it had taken and she felt her attacker’s warm sperm run out of her and down her thighs where it pooled in her panties and stained her stocking tops. The front gusset of her pantyhose was soaked with her own spend whilst her attacker’s semen ran down her thighs into her bunched up panties. Her head was spinning with the realisation of what had just happened to her; then she began to wonder what would happen next.

To be continued…………………………………

 

Michele pulled at her bonds, struggling and wriggling on the bed trying to break free for a few minutes until she realised that she was securely tied and had no way of escaping.  Ellie sauntered over to the bed and looked down at Michele,

 

“Well honey, looks like we have you just where we want you; I think we are going to start to really have some fun now,” she sneered.

 

Michele opened her mouth to scream and Ellie slapped her face hard.  Michele’s face was jerked to one side with the force of the blow and her eyes watered with the pain.

 

“Look bitch, you can try to scream all you like, but if you do I’m going to invite my friends here to smack you around a bit as a prelude to whatever else they’re going to do to you.  And once they’ve done that we can gag you if you still insist on making a fracas, although I’m sure they have better ways of stuffing your mouth, so shut the fuck up or wear the consequences,” Ellie threatened.

 

Realising that resistance was useless, Michele lay still and contemplated the circumstances in which she now found herself.  She had already seen Ellie and the fat cop who she had encountered earlier in the evening; she wondered who else comprised “we” Ellie had spoken of; she looked around to see who else was in the room.  There were three other men sitting at a table drinking.  Their chairs were turned towards the bed and they had obviously been entertained by the performance provided by Ellie fellating the cop while they waited for Michele to come around.

 

They were rough looking types, dressed in jeans and T-shirts; solidly built and appeared to be in their middle forties.  The men were talking amongst themselves in gruff voices; their language vile and littered with swearwords.  Their eyes glistened as they looked hungrily at Michele tied to the bed.

 

“I won’t worry too much about formal introductions Michele if you don’t mind.  You met my friend here from the local constabulary on your way to the party earlier in the evening, and I suppose it’s fair to say you’ve known him only briefly but certainly intimately,” Ellie smiled cruelly.

 

“These other three gentlemen are also aficionados of special ladies like ourselves; that is to say they have a penchant for attractive transvestites; and they particularly like a little bit of, shall we say, extremism when it comes to sexual encounters.”

 

“They are very close friends of mine, and over the years I’ve been able to sacrifice quiet a few ‘virgins’ to the altar of their desires; if I might wax poetic,” Ellie went on.

 

“Most of the girls I have lured into their clutches have left having eventually enjoyed the encounters; a few have not; but none have ever been a position to complain.  So I suggest you just relax and enjoy what I am about to allow you to experience; if nothing else you will at least leave this room enlightened as to what two transvestites and four hungry mature men can accomplish in the way of sating their appetites.” Ellie finished.

 

Ellie turned to the three men who had been eagerly watching and listening to her explain the situation to Michele, like a pride of lions watching their wounded prey.  Their eyes glittered in the darkened room as they feasted with wanton lust on the bound transvestite.  Michele’s miniskirt had ridden up when she had struggled at her bonds and her luscious nylon sheathed legs were exposed right up to the tops of her thighs and her red satin panties peeked from under the hem of her skirt.

 

“Gentlemen, meet Michele.  Michele, meet the gentlemen,” Ellie introduced them sarcastically.

 

“As for you, my law enforcing accomplice; you can sit over there on the lounge and I will keep you suitably amused whilst Michele and our three comrades entertain us.”  Ellie sauntered over to an overstuffed lounge which had been positioned beside the bed.

 

The three men rose as one and sauntered over to the bed and they looked down and surveyed Michele tied to the bed.  They stared at the middle aged whore; her black leather miniskirt rucked up around her waist from her struggles, her red lace garters clipped to her black stocking tops; legs spread wide and her ankles tied to the bed just above her black high-heeled sandals; her red painted toenails visible through the diaphanous nylon.  Michele’s leopard-skin print nylon blouse was opened at the top displaying her red satin brassiere.

 

Michele’s face was framed by her brunette wig the lighter tints highlighted in the lamplight, her heavily mascared eyes peeked from under her fringe, emphasised by her blue and pink eyeshadow. Her rouged cheeks and ruby red lipsticked lips were accentuated by her pale foundation and face powder.  Michele’s earrings and necklace glittered in the dim light.

 

One of the men noticed her anklet glittering and reached out and caressed her ankle and then slowly ran his hand up her leg to her stocking top, stopping briefly to play with her garter strap and then continued up her thigh until his hand rested on the front of her panties.

 

“She’s wearing pantyhose under her panties and stockings guys; looks like this whore will need to buy a new pair tomorrow,” he chuckled to the others.

 

Michele wriggled as she felt the man’s hands on her leg and panties.

 

“Hold still now honey; Michele is it?  My friend is going to untie your legs and if you give us any trouble; well Ellie has already explained what we will do,” he threatened.

 

Michele felt the bonds on her ankles loosen and then her ankles were free; she tried to close her legs but the man who had untied her legs now held them wide apart and pushed her ankles down on the bed. 

 

“Keep her like that Joe; if she moves or makes a sound belt her one,” said the man who had his hand on her thigh to the man holding her legs down.

 

Then he and the other man started to undress; they dropped their clothes where they stood and kicked them away into the centre of the room.  One of the naked men then relieved Joe of his task and Joe shucked out of his clothes so that all three of them were now naked.  Michele strained her neck up off the bed and saw the three men standing around the bed with their erections standing proud under their round bellies.  She started to cry and the man named Joe slapped her once across the face.

 

“Keep quiet bitch; last warning!  Next time you will get a proper belting,” he growled.

 

“Fuck she looks good,” said the man who had stroked her legs, “can I fuck her first?”

 

“I think that’s only fair Steve,” Joe replied, “I fucked the last trannie that Ellie got for us first.  You ok with that Bill?”

 

“Sure,” Bill answered, “I’d prefer a blow job before I fuck her anyway.”

 

Michele’s head was spinning; she knew that resistance was futile, maybe she could reason with them?

 

“Look, Bill, Joe, Steve; what about if you untie my wrists and just let me go?  I won’t tell anyone about this honest.  You’ve had your fun now so the joke’s over; come on guys let me go,” Michele Begged.

 

All three of the men standing over Michele, the fat cop, and Ellie laughed in unison.

 

“You silly cunt; we ain’t joking; and we ain’t letting you go; and I’ll let you into a little secret Michele; you won’t be telling anyone about what happens here tonight.”

 

“Are you really going to admit to being a transvestite?  And anyway who you going to tell; the police?  Our friend Bob over there is the police you dumb cunt!”

 

“And I gotta let you into a little secret; our real names aren’t Bill, Joe, Steve and Bob.  Sure you know Ellie is Eddie but Ellie saved you when you got drunk and passed out at the party.  She was your saviour and friend tonight in front of all those witnesses; do you really think anyone is going to believe that she took you up to her hotel room and gave you to four men to have their way with?  It’s just ludicrous!” Joe lectured Michele.

 

“Now shut the fuck up and you take what we give you and you won’t get hurt; like Ellie said you might even enjoy it,” he finished.

 

“I know how to shut her up,” Bill said and bent down and began to kiss Michele on her painted red lips.

 

Michele felt Bill’s tongue invade her mouth and attempted to move her head out of the way but it was useless, he continued to kiss her, the taste of whisky and cigarettes on his breath.  She felt one of the men; Joe she figured as Steve had hold of her legs, untie her wrist and grip it firmly.  He moved her hand down and then she felt her hand come into contact with his erect member and she tried to flinch it away.

 

“Don’t you fucking well make me hurt you bitch; you take what I give you and don’t even think of hurting me down there,” Joe growled.

 

Michele wrapped her fingers lightly around the rubbery fat cock and placidly held it there.  Joe held her wrist and began to slide his cock in and out of her loosely clenched fingers.  He looked down at his thickening member wrapped in Michele’s hand, her red painted fingernails accentuating her delicate fingers, and groaned. He swayed back and forth on his heels and fucked her hand.

 

“Oh yeah; wank that cock baby! Wank that cock!” he moaned.

 

Michele felt her other wrist being untied and when her right arm was freed it was placed over Bill’s shoulder and she left it there, limp, so that she held him in a faux embrace.  Bill sat on the bed as he continued to kiss Michele and he felt her start to respond.  Gently at first, she tentatively slipped her tongue into his mouth and then when he pressed his lips harder against her lipstick painted mouth, she kissed him back passionately.

 

Michele was becoming aroused despite the fact that she was being forced to participate in their debased game.  Bill’s kisses were deep and exciting; she responded despite her feeling of abhorrence and used her free arm to embrace him.  Instinctively her right hand clasped onto Joe’s cock and started to slowly masturbate him.  She felt her fingers slide along the sleek hard shaft and then over the spongy bulbous head; she manipulated the sensitive area at the bottom of glans and heard him sigh.

 

Bill lifted his face from hers and Michele reluctantly allowed him to escape her embrace.  He bent down and kissed her lightly on her lips and then both eyelids.

 

“God you are one pretty whore,” he whispered into her ear.

 

Michele became more excited and felt her own cock hardening inside her satin panties.  Bill shifted position so that he was kneeling on the bed, his groin next to Michele’s head.  She offered scant resistance when he turned her head towards his erect member and rubbed it on her lips.  Michele opened her lips and skimmed her tongue across the head of Bill’s penis.  Bill pushed forward and his glans slid over her lips and into her warm wet mouth; he rocked back and forward and pushed his cock in and out of her mouth; fucking Michele’s oral cavity as her lipsticked lips clamped on his shaft and her tongue lashed at his cock-head.

 

Michele couldn’t help herself; she was enjoying playing the role of a whore; sucking Bill’s cock whilst she stroked Joe’s cock with long slow strokes.  She enjoyed the feeling and taste of the hard member in her mouth, unlike the fat stubby cock of the cop, this cock was long, sleek and the secretions that leaked from the eye of the penis were sweet.  The cock in her hand was also long, but thick and veiny; she loved the silky feel of the skin of the shaft contrasting with the spongy feel of the head.

 

Then she felt Steve’s hand under her skirt start to stroke her own cock through the layers of her satin panties and pantyhose.  As the satin of her panties rubbed against her nylon encased cock it sent small shocks of pleasure shooting through her.  Then she felt Steve move onto the bed between her legs as he continued to stimulate her through her underwear.  She was startled when she felt Steve’s other hand push aside the crotch of her panties and a finger probe at her anus through the nylon gusset of her pantyhose.  She wriggled a little but she found the finger stimulating.

 

Michele could not believe that she was becoming an active participant in her own rape; she was enjoying it, she couldn’t stop the raging desire that coursed through her.  She sucked on Bill’s cock and used her free hand to stroke the shaft as she slobbered over the head of his cock, alternately kissing, licking and sucking at the fat cock-head.  Her other hand slid up and down Joe’s member, varying between squeezing it and then running her red painted fingernails gently up and down the shaft and under his balls.

 

Steve was mesmerised by Michele’s nylon sheathed legs; he manipulated and caressed Michele’s hardening cock through her knickers and with his other hand he stroked her stockinged calves and thighs. Steve straddled Michele’s right leg and began to hump her thigh.  Then he lifted her leg and worked his cock into the silky furrow behind her knee; he groaned revelling in the soft sensations in his cock as he slowly worked his penis in the gossamer nyloned crevasse behind her knee and thigh.

 

Steve slid his cock further up Michele’s thigh until he could force it under her stocking top so that it was trapped in the silken diaphanous tunnel between her stocking and her pantyhose encased thigh.  He fucked the gauzy chasm leaving a silver trail of pre-seminal fluid soaking into her nylons as his cock throbbed and released sticky beads of pre-come.

Michele could feel Steve’s hard penis sliding up and down her leg and was surprised to find that the sensation was highly arousing.  When he slid his cock into the silken trap behind her bent knee she clenched her knee so that his penis was clamped between the sensitive nylon sheathed skin of her calf and thigh; she moved her leg from side to side and felt Steve’s hot cock secrete warm moist droplets of sticky pre-come which was absorbed into her stockings and pantyhose.

 

When Steve moved his cock up her leg and started to fuck her thigh with his cock between her stocking and pantyhose she pushed her leg up into his groin so that her pantyhosed thigh rubbed against his scrotum, sending delightful stabs of pleasure through his balls.

 

Michele wanked at Joe’s cock; squeezing the shaft as she worked her fingers up and down his manhood; when she came to the end of his shaft she worked her fingers in circular motion around the glans and then grasped at the shaft and slid her hand back down the length of the engorged member.  She sucked and slavered at Bill’s cock, occasionally allowing his member to come right out of her mouth and then she licked the entire length of his phallus and gently nibbled at the head whilst flicking her tongue under the sensitive skin where the glans joined the shaft.

 

Joe was rocking back and forth on his heels, fucking Michele’s hand as she wanked him.  He looked into her pretty made up face and her rouged cheeks and mascared eyes, fringed by her silky hair aroused him; but what stimulated him the most was the way she worked her ruby red lipsticked lips up, down and over Bill’s cock.  For a girl who was terrified of what was about to happen to her twenty minutes ago, she had certainly changed her tune; she really was a whore.

 

Joe cast his eyes down Michele’s body, he reached out and caressed her belly through her nylon blouse and scanned down to her groin where her miniskirt had been pulled up and was rucked up around her waist exposing her garter belt and red satin panties.  Steve was slowly massaging Michele’s cock through her panties and his other hand was pressing down on her magnificent black stocked leg; his cock jammed between her stocking top and her pantyhosed thigh as he rocked back and forth and fucked the gossamer tunnel.

 

Steve was in ecstasy, but he forced himself to remove his cock from the silken trap of Michele’s thigh and moved back down the bed so that he was between her spread legs.  He moved up between them and pushed his cock down onto her panties to replace his hand which had been stroking Michele’s cock through her satin knickers.  He pressed down and began to slide back and forth, fucking Michele’s silken encased cock with his own.  The feeling was electrifying as his shaft felt hers start to throb through her tight pantyhose gusset and the satin panel in front of her panties.

 

Michele felt Steve’s manhood rub against her own as he dry fucked her through her knickers and hose; the taut nylon on her cock sending sensations all through her member.  She bucked and lifted her crotch to meet Steve’s thrusts and gyrated her hips to enhance the sensations shooting through her groin.  Then she was a little disappointed when she felt Steve move on top of her and his cock slid down her shiny satin panties and eased under the gusset; she felt the head of his cock nestle in the crack of her arse and begin to push against her arse bud, forcing the nylon of her pantyhose into the puckered hole.

 

Steve was gasping with pleasure as his cock rubbed against Michele’s nylon sheathed, engorged member.  He could easily come this way and enjoy every second; but he wanted to fuck the lovely transvestite who lay beneath him sucking the cock of his friend and masturbating the other.  He pulled back and shuddered as the glans of his penis rubbed feather lightly along Michele’s panties; he pushed forward as the knob of his cock nestled against the elasticised crotch of her panties and then forced his hard cock under her panty crotch and against her pantyhosed arse. He manipulated his crotch and wriggled his cock in the silken pantyhosed valley of Michele’s arse crack until he felt the head of his penis nestle in the bud of her back passage.

 

Steve pushed forward and felt the nylon pantyhose gusset begin to give; he pushed harder and his cock broke through the gossamer prison and wedged into Michele’s anal bud.  His cock was wet and lubricated from his pre-seminal secretions and he continued to push forward and felt his cock stretch Michele’s sphincter and finally the head of his penis penetrated Michele’s virgin passage.

 

Michele felt Steve’s cock begin to slide inside her; at first it was uncomfortable but she forced herself to relax and then the sensation of being slowly filled with hard cock began to excite her.  To Michele’s own amazement she actually started to push her groin against Steve to force his cock further and deeper inside her.  She felt her passage open as his manhood filled her and then she felt Steve’s groin hard against hers; he was all the way in.  Michele heard Steve groan and she lifted her stockinged legs up and wrapped her high heels around his waist and began to buck underneath him.  Steve held on and Michele began to fuck him, raising her buttocks off the bed in time with his thrusts in a slow steady rhythm.

 

Michele had now actually become the whore that she had only pretended to be at the start of the evening.  She was not only dressed as a whore; she was behaving like a whore.  She had already sucked her first cock before she got to the party, she had had lesbian sex with Jill on the balcony; now she was having forced sex with three middle aged men; and she was loving it!  ‘Yes’, Michele thought to herself, ‘I am a whore and I adore being a whore; what have I missed out on all these years?’

 

The three men and Michele began to concentrate on inducing their orgasms.  Steve was now slamming his cock in and out of Michele’s back passage and she was bucking under him; raising her buttocks off the bed to meet his thrusts.  She could feel his pulsating cock stretching her back passage and pushing against her prostate, sending waves of sexual sensations through her body; she wiggled her arse and clenched and unclenched her sphincter to increase Steve’s pleasure and enhance her own gratification.

 

Bill’s cock was pulsing in her mouth and she felt his orgasm approach as he pushed his cock in and out of her lipsticked mouth, holding her head as he fucked her face.  He groaned as Michele slavered at his erect manhood, running her tongue over the head and shaft as she felt the vibrating piece of flesh begin to convulse.

 

Joe was rocking on his heels fucking her hand in time to Michele’s hard strokes as she masturbated him.  He looked at her ruby red fingernails and the glittering jewellery on her fingers and wrists and felt his own climax build.  Michele could feel Joe’s cock start to shudder in her fingers and she gripped it hard and wanked at the erect piece of manhood; increasing the pace as she felt the cock quiver and shake in her hand.

 

Steve’s cock erupted deep inside her and Michele felt the splash of his seed flood  her passage; Steve’s cock was buried deep inside her, in her right up to the hilt, and she pushed up to meet Steve’s groin and felt his erection quiver against her prostate gland as she filled her panties with her own hot wet emission.

 

Bob’s cock exploded in her mouth at the same time and her mouth was inundated with salty hot come; she gulped it down as fast as she could but still some of the viscous white fluid escaped her mouth and ran down her chin.  Joe saw this and groaned as own penis spewed forth jet after jet of hot semen all over Michele’s hand, and arm.  Jets of his spend shot through the air and splashed on her blouse; the gobs of white ejaculate contrasting against the leopard-skin nylon.

 

Michele was writhing in ecstasy as the three cocks filled her and covered her with hot come.  Her arse was convulsing as Steve plunged his last few thrusts deep inside her, draining the last of his issue.  Her mouth was filled with Bob’s semen and he pulled his cock out of her mouth and let the last few jets of his release splash over her pretty, heavily made up face; a string of semen flew out of his cock and glistened in her hair.

 

Joe’s penis had shot stream after stream of semen over Michele and the globs of glistening semen on her blouse was joined by a thick viscous stream of come which had splashed over her rucked up skirt.

 

Michele lay there quivering in orgasmic bliss as her own climax subsided; her hot fluid filled her panties as she tasted Bob’s come in her mouth and felt his hot seed on her face.  She was covered in semen inside and out; she felt sated; satisfied like she had never been before.  Michele had become a Transvestite whore and she loved it!

 

……………………………………..To be continued.

 

I went to bed that night and relived the events of the evening over and over in my head.  It was like a dream.  I had actually passed myself off for Julie!  Every thing inside me told me I could but there is a lot of difference between thinking and doing and I had done it. The only one that knew was my sister. Everyone else, Mom, Dad, my little sisters, Karen and Holly and even Brian thought I was Julie!

 

The next morning it was hectic in the house. I put on latex gloves to hide the fingernail polish. Dad and Mom left early for work. My attention was consumed in getting Karen and Holly dressed and off to school. Julie came in the kitchen and hugged me telling me again how much she enjoyed last night. She then left for school.

 

When everyone had left the house I went upstairs and stripped off my clothes and showered, washing Brian’s dried cum out of my hair and off my body. After drying off I picked up the clothes Julie had left laid out on my bed. I laughed to myself at the thought that she laid out what clothes she wanted me to wear. I dressed and went into Julie’s room and sat down and blow-dried and styled my hair and began to put on my makeup. My conversation with Julie was running through my mind as I slowly and meticulously applied it.

 

 

 

I was angry with her. “ Why the hell did you call Brian? And why did you tell him you wanted to suck his cock really intending for me to give him the blowjob?” I demanded after the door to her room was closed.

 

“ Because it was going so well with Dad and Mom. You had them fooled and I began to see how you could help me out of another situation.” Julie said looking me straight in the eyes, “ Tomorrow Brian will have told everyone at school that I sucked his cock!”

 

“ Why the hell would you want him to tell everyone?” I blurted out.

 

“ Because I really didn’t want to do it! I think its sick and degrading to let a guy dominate me that way, on my knees before him. Besides I am more attracted to girls and now they will think I am straight because you gave Brian a blowjob. The guys were already starting to tease me about being a lesbian. Even the girls were starting to act funny around me even though I haven’t acted on my feelings, besides you should know what the girls go through, especially if you are going to take my place at school.”

 

I was probably as shocked at her confession as she probably was when she saw me dressed like her. I was speechless. Julie had told me that some were teasing her but I had no idea!

 

We both had secrets that we had kept from each other. My anger had faded.

 

“ Besides it looked like to me that you were enjoying him sucking on your nipples and it was so sexy watching you suck his cock.” Julie added.

 

“ What? How did you see what went on?”

 

“ Well when you left the house, I followed and stood behind a tree not ten feet from where you were in the park and with the full moon out, it was as if it was broad daylight. The moonlight lit your bodies up. Anyone who would have even driven down the street would have seen you two. It was so public, so hot!”

 

I didn’t know what to say so I turned and opened the door and went to my room, stripped off her clothes and climbed into bed not even caring about Brian’s cum all over me.

 

 

 

I completed my makeup, stood up and walked to the full-length mirror in the corner of the room, examining every angle making sure everything was in order. I had plans for the day and needed to put things in place.

 

I went about my daily chores, making all the beds, picking up Karen and Holly’s room, putting their dirty clothes in the hamper, vacuuming the carpet both upstairs and down. I scrubbed the bathrooms and mopped the floors in each. Then mopped the kitchen floor. Dad still hadn’t fixed the lawnmower yet so the lawn would have to wait till the Saturday.

 

By 11 o’clock I was done. Now I had the rest of the day to do whatever I wanted. Mom and Dad wouldn’t be home till after midnight tonight. They were going to attend a company dinner. Julie was going to be out late because of the football game and dance afterwards. My little sisters were going to Grandpa and Grandma’s after school and Mom and Dad would be picking them up on their way home tonight. So I had at least 12 to 13 hours to do whatever I wanted!

 

I picked up my purse and locked the door and headed for the mall walking past the park on the way. I stopped for a moment to watch some moms with their children playing in the spot where hours ago I was on my knees sucking Brian’s cock. I couldn’t help but smile as the scene flashed through my mind and thinking of Julie standing by the tree nearby.

 

He called me his bitch and last night I was just that. His bitch sucking his big cock. I wondered how things went for Julie at school and how her date with Brian would go tonight. I decided to go and sit and watch the kids play and so went to the very bench we were at and sat down. One of the moms came up and introduced herself to me.

 

“Hi I’m Samantha but my friends call me Sam.” She said as she sat down next to me.

 

“Hi I’m Julie.” I said back.

 

“If you don’t mind me asking how come you’re not in school?” she asked.

 

“I’m doing home schooling. I am just running some errands for my parents” I said casually.

 

“Oh ok. I didn’t mean to be nosy but it’s just unusual for a young girl to be here during the day. Although I have seen you walk by before.” She paused and looked over at her child playing on the swing. “You must live close by, I live right over in the blue house over there. Do you have brothers and sisters dear?”

 

“Yes.” I said, adding, “ Two younger sisters and a twin brother.”

 

“Are they home schooled as well?” She asked.

 

“No, just me.” I said.

 

“Hey could you baby-sit during the day sometime? Sometimes I am looking for someone to watch Michael while I run errands and if you think you would be interested can I call you? I’ll pay you good.”

 

“Let me think about it and talk it over with my parents. I know where you live and will let you know. Ok?”

 

“That would be great, thanks.”

 

“Well I have to go, it was nice meeting you Sam.” I said and getting up I walked down the street and turned heading for the mall.

 

When I reached the mall, I purchased my own makeup and fingernail polishes so that I wouldn’t have to use my sisters. Afterwards I went into one of the restraunts and sat down and ordered a salad.

 

When I finished it I then walked slowly home enjoying the warm sunny day with the breeze blowing my skirt. The air felt good on my bare legs. I stopped to rent a video from the adult section in the back room of the store. The guy at the video store reminded me that I needed to be 18 to rent the movies from the back but after giving him a flirtasous smile and leaning over the counter to show some cleavage smiled back at me said,

 

“ Its on the house. Just bring it back and let me know what you scenes you enjoyed.” He said smiling back at me.

 

“Ok.” I said blushing.

 

By the time I reached home it was about three o’clock and in a couple hours my friends would be out of school and would be stopping by to hang out. It was our regular ritual. Wayne, Bill and Mike and myself would usually smoke a few joints and sometimes Wayne would have a bottle of alcohol that he took from his dad’s bar in his den. We would put some music on in the garage and get really buzzed and doing tricks on our skateboards in the driveway or down the street.

 

I couldn’t count the number of times they talked about Julie and how she was really hot! When they would talk about her I could see the bulges in their pants grow. At times they even joked about getting hard thinking about her and then rub their cocks through their jeans to show their manhood and we would all laugh.

 

They were the geek type with their glasses and not so handsome looks and bad hairstyles. They hung out with the other geeks at school and I knew they weren’t very good with the girls but liked to talk big like most of us.

 

I had fantasized about seeing their cocks but being a guy I would never dare let it be known for fear of loosing my only friends besides I was struggling to understand my feelings.

 

After sucking Brian’s cock last night and everyone thinking I was Julie. I couldn’t stop thinking about their cocks and how it would be suck theirs.

 

Tonight it would be Julie entertaining Wayne and giving him a present he would never forget! I picked up the phone and called Bills cell phone and left a message for him not to come over tonight. That I was doing something with Wayne for his birthday and although I wish I could include them it wasn’t possible.

 

I then called Mikes cell phone and left the same message.

 

Tonight both our fantasies were going to come true.

 

I went to the kitchen and took out the refrigerator a large smoked sausage. Time to do some research. I went into the family room and put the video in and turned it on. It was all about different girls sucking cock and the guys eating their pussy’s.

 

I watched intently trying to learn the different techniques the girls used. I realized last night that I need to know more about how to suck a cock.

To give them the most pleasure I possible could.

 

I continued watching the movie over and over imagining myself sucking the cocks, imitating what they did while sucking on the sausage. With each scene I was beginning to get more excited about this evening.

 

I removed the videotape, put the sausage back in the fridge and went upstairs and hid it in my closet behind some clothes. Wayne would be over soon and I certainly didn’t want to forget the tape in the VCR. The last thing I needed was to have Mom or Dad or anyone for that matter turn on that movie.

 

I looked myself over in the mirror checking my makeup and outfit and reapplied my lipstick.

 

“Humm, perfect.” I thought out loud.

 

I heard the garage door open up and looked out the window. It was Wayne. He went in and then I heard the music coming out. I stood in the window watching for several minutes. I couldn’t believe how nervous I was. I was shaking.

 

I kept thinking about last night and how even Mom and Dad couldn’t tell Julie and I apart.

 

I went down stairs and went out the back door, down the sidewalk to the garage and looked in. Wayne was at the counter with his back to me mixing some drinks. Next to the bottle of vodka there were several joints.

 

Oh-Yeah this was going to be a good night. Everything I need was there to sooth my nerves.

 

Suddenly his cell phone rang.

 

“What’s up Bill?” I heard him say. “Yeah, I’m here now.”

Then there was silence as he listened. I sat down on the bench that was at the side of the driveway. I had a perfect view of Wayne.

 

“No way man!” Then silence on Wayne’s part again.

 

“Ok. Well be cool.”

 

“Yeah Kacy and I will just have to party without you.”                

 

“Yeah its cool. You guys are coming over to my house Sunday right? Remember it’s my birthday and I my folks said I could have some friends over for dinner and I thought we could all just hang out afterwards. I got a new video game, its really cool!”

 

“Great! Yeah man, it will be the four of us. Well hope it all works out. Talk to you later.” Concluding his conversation putting the phone down.

 

Everything was going according to plan.

 

I got up and walked into the garage “Hi Wayne. How’s things going?”

 

Wayne wheeled around as if to try to hide the stuff on the bench. “ Hi Julie!” he blurted out, his voice highlighting his nervousness.

 

“Hey, eh, Kacy isn’t going to be home tonight. He wanted me to tell you.” I said.

 

“Oh ok. I guess I’ll just head home then after I close up. Thanks Julie.”

 

I walked over to him and looked behind him at the drinks and pot, “What this? Do you mind if I hang out with you a bit? Maybe we could smoke one of these together. If you don’t mind that is?” I said reaching around and picking up a joint and putting it to my lips.

 

“Ah, well, Ah yeah, sure, that would be cool.” He said with a puzzled look on his face.

 

“Kacy told the other guys not to come over.” I said. The puzzled look remaining on his face.

 

I reached over and stuck my hand in his front pants pocket to get the lighter. I wrapped my fingers around it and felt movement in his crotch. I moved my fingers around more and looked him in the eyes as I felt his cock through the material.

 

“ Mind if I use your lighter?” I said slowly almost in a whisper.

 

Wayne was frozen stiff! Not sure what to do or say.

 

I pulled the lighter slowly out of his pocket rubbing my fingers along his cock and putting it in his hand.

 

“Will you light if for me?” I said not breaking eye contact with him.

 

“Oh, sure. I’m sorry!”  He said and raised the lighter and flicked it to life. I broke eye contact and put the tip of the joint in the flame and took a long drag on it and holding it in then handed it to him.

 

I then picked up one of the drinks on the counter and walked slowly and seductively outside to the bench where I was sitting before. I could feel Wayne’s eyes watching my every move. He followed carrying his drink and the joint. I sat down and crossed my legs. My short skirt riding high up my thigh revealing practically all of my legs.

 

Patting the space next to me I said, “Come on sit down, I won’t bite. It’s a really nice afternoon and I love sitting in the Sun.” Then putting the drink to my lips, took a deliberately long slow drink of the liquid in the glass. Wow it was mixed strong, practically all vodka with just enough orange juice to add color to it.

 

Wayne sat down and I could tell he was really nervous about being so close to me. It was kinda funny and that I had to laugh, He had no idea why I was laughed. Wayne and I had sat on this bench many times getting stoned and he was never nervous when I was his friend Kacy, just one of the guys!

 

He took another hit off the joint and reached out to hand it to me, his hands visibly shaking. I touched his hand pausing for a moment before taking the joint, licking my lips slowly, then I put it to my lips and took a deep drag and held my breath holding the smoke in my lungs.

 

I put my head back against the chimney behind the bench and looked up at the clouds floating bye in the late afternoon sky knowing that as I did, my breasts would be straining against my low cut blouse. I intentionally didn’t wear a bra today and even though I was looking up I could feel my nipples pushing on the fabric.

 

“Ummm” I said releasing the smoke slowly, “ Wow that’s some good pot. Is it laced with something?” Then rolling my head over towards Wayne catching him staring at my chest and legs.

 

He suddenly realized that I was looking at him and he jerked his gaze away, grabbed my glass and stood up not answering my question.

 

“Let me refill your drink.” He announced and scurried off to the garage. I watched him as he went to the counter and poured the liquid from the bottle into my glass. Funny he didn’t put anything else in it, just vodka. I took another drag on the joint and leaned my head back and waited for him to return.

 

“Here you go,” he said sitting down again. I leaned forward and released the smoke from my lungs and took the drink and put it down on the patio stone next to the bench.

 

I was really starting to catch a buzz between the strong drink and the weed. I took another deep hit and decided to get things moving. It was obvious he wasn’t going to make a move.

 

I leaned over and grabbed his head and pulled it down to me and planted my lips on his kissing him softly. When he started kissing me back I began to blow the smoke into his lungs. I let go of his head breaking off the kiss leaning back on the bench.

 

He then blew the smoke out and looked at me with a real puzzled look on his face.

 

“What?” I asked.

 

“I just don’t get it. You’re the most beautiful girl in school, a cheerleader on top of it and you have never, ever, come down to hang out with us before. In fact at school you don’t even know I exist. And now here you are getting stoned and you just kissed me? What’s the deal here? Are you setting me up for some kind of joke or something? And why did Kacy tell the others not to come over?” Wayne stammered out with his voice breaking.

 

“Look, Kacy told me its your birthday Sunday and he wanted me to give you a his present but not with everyone around.” I said staring him in the eyes.

 

“W h a t ‘s the present?” he asked looking away.

 

“Well, Kacy wants me to suck your cock” I said as I put my hand on his upper thigh. His cock was definitely growing.

 

“What?” he managed to get out not believing what he had just heard.

 

I got up and dropped the cushion I had been sitting on down on the patio stones in front of him and kneeled down. “Well he told me how you guys talk about me and this is his gift to you so just enjoy it. Eh, the thing is, you can’t tell anyone. Do you understand that?”

 

I took another drag on the joint and handed it to him. I then reached up and unbuckled his belt. Unbuttoning his pants and slowly unzipping his pants as I blew out the smoke from my lungs letting my fingers trace his cock.

 

I grabbed his pants at the waist and looked up into his eyes and said, “ I need a little help here!”

 

With out a word he raised his body off the seat and allowed me to pull his pants down. His cock springing straight up. It was larger than I had imagined. Then bent untying his shoes pulling each one off, then the socks followed by his pants all the while I didn’t take my eyes off his seven or eight inch cock.

 

When he was naked from the waist down I stood up and unbuttoned my blouse swaying to the music and dropped it on top of his pants. “Do you mind if I get comfortable?”

 

My breasts being exposed to the late afternoon air and his eyes, made my nipples stick straight out from the mounds of my breasts. I knelt down between his legs and picked up my drink, standing up slowly allowing my chest to brush against his cock and balls and inner thighs. Picking up his hand I placed them on my breast. He squeezed it really hard just as I took a drink from my glass. I swallowed hard.

 

“ Ouch! Hey easy there big boy. Gentle is better!”  And then took another drink of the really strong drink. This time he gently squeezed my breasts and I leaned forward and put one of my nipples to his lips. I could feel his cock and balls up against my legs so I moved them back and forth.

 

“Ummm , Yes that’s the way, you big stud. Ummmm that feel so good.” I said as he sucked gently on my nipple. This is the second time a guy had sucked on my nipples and I was still amazed at how sensitive they were.

 

“Umm now lightly use your teeth to nibble on it, oh yeah that’s the way!” I moaned as he lightly took it between his teeth.

 

After about five wonderful minutes I backed away from him pulling my nipple out missing his mouth on them instantly.

 

“Awwwwwwe.” I said pouting, the disappointment being obvious in my voice.

 

I handed him my empty glass and then reached up and cupped each of my own breasts and pinching my own nipples played with them rubbing his saliva around in front of him. His eyes taking in every move I made. I moved seductively to the music that drifted out of the garage and then leaned forward kissing him.

 

Kneeling down before him, I placed his manhood against my naked chest reached up and unbuttoned his shirt allowing my hands to fondle his chest. I bent down and nibbled on his nipples and then pinching them, rolling them between my thumbs and finger making then hard.

 

“UMMMM,” Wayne sighed.

 

Turning my focus to his cock I lightly dragged my red painted fingernails down his chest and stomach to his cock grabbing his hard cock rubbing it over the soft flesh of my breasts and hard nipples.

 

“Oh god Julie, that feels sooooo good!”

 

I moaned with pleasure feeling his soft, hard  flesh as I played with my nipples. “Ohhhhh yeah.” I whipped my head back throwing my hair behind me and licking my lips slowly, “Ohhhhhhh.” I whispered softly leaning my head back.

 

Setting back on my heals, I used my fingernails to lightly trace the line on the underside of his cock until they reached the sack holding his swollen balls.

 

“Awe Yeah. God I can’t believe this is happening.” The words escaping from his lips.

 

I leaned forward and put my bright red lips on the tip of his manhood planting a soft kiss then opening my mouth slightly I stuck my tongue out and licked the hole at the end.

 

“Goddd Yesssss.” His word trailed off to a soft hiss.

 

His cock leaped I could taste the flavor of his sweet pre-cum leak out. Grasping the base of his cock with one hand I pulled down on it stretching the skintighter making the head swell more. With my tongue I licked all around the ridge at the base of the head. With the other hand I cupped his balls gently massaging them.

 

“OHHHH that feels so good!” he moaned almost in a whisper.

 

I looked up at his face. His head was back and eyes were closed. Wayne’s hands were gripping the bench to steady himself.

 

I licked down the same path my fingernails had traveled only a moment ago and holding his balls up to my mouth licking each one, then sucking them one at a time into my mouth using my tongue moving them around in my mouth then pulling them out while still sucking until they reached their limit and plopped down. I then traveled back up to the tip licking as if licking an ice cream cone.

 

“Ummmm, Oh God Julie your red lips are sooooo hot on my cock.”

 

I looked up into his eyes as he stared back down at me. His eyes were glassed over from the pot, booze and pleasure. I let saliva drip from my mouth onto his cock and rubbing it in pumping up and down slowly on the shaft.

 

I brought my mouth back to the head and this time I took it into my mouth until my teeth were just over the ridge and lightly bit down, sucking deeply on it while I moved my tongue back and forth on the underneath side.

 

His breathing was getting heavy as he tried to speak. “Yeah that’s it, please suck on it.”

 

I released my teeth and pulled it back out of my mouth and then sucked it deeper. I repeated the motion fucking his hard pole with my mouth each time moving my lips farther down until his cock hit the back of my mouth.

 

“UMMM, UMMMM” I moaned through my nose as I worked his pole with my tongue and mouth.

 

“Oh god, don’t stop!  Please.” He pleaded.

 

Wayne stretched his legs out straight and tensed up from the sensations my mouth was giving him. I lowered my head farther allowing his cock to push into my throat. I continued to fuck my mouth and throat.

 

“Holy Shit that feels sooooo good.” He moaned.

 

At last my nose was pressed into his pubic hair giving me a whiff of his sweaty body odor and my chin against his balls.  I held him deep in my throat for a moment enjoying his masculine smell and then as I pulled my mouth back up sucking until he came all the way out of my mouth making a slurping sound.  

 

“Ummm stud, you have a fucking huge cock. I just want to eat it up.” I whispered talking dirty in a seductive voice as I moved my fingernails down his inner thighs and legs.

 

“Oh god do!” he responded.

 

I grabbed it again and felt his butt cheeks tighten his cock swelling up even more as I licked around the crown of the head. I knew he was going to cum soon. I pumped up and down on his dick.

 

“OH GOD I AM GOING TO CUM! OH SHIT I DON’T WANT IT TO END!” Wayne moaned.

 

I sucked the head back in my mouth and continued to jack him off. I released his cock out of my hand and reached up to his bare chest with both hands bracing myself, digging my fingernails in. I could feel the flesh give way under my nails.

 

“ OUCH! OH SHIT I AM GOING TO SHOOT MY LOAD!” he practically shouted.

 

I kept my nails dug in his chest. I had him on the edge and now I was going to take him over the top.

 

I sucked more moving my head in circular motions around his cock.

 

“HOLY SHIT HERE IT COMES! OHHHHHHHH GOD! YESSSSSS! GOD YESSSS! YOUR MOUTH IS SO FUCKING HOT” Wayne shouted in deep heavy breaths.

 

 I dragged my nails down his chest making him erupt sending his hot musky juices into my mouth.

 

Screaming out “OWWWWWWWWW, OHHHHHHHHHHHHHH SHIIIIIIIIIT!

 

I swallowed, and then I released his cock from my mouth only to grab it with my hand. I pumped his shaft up and down until it stopped. His cum dripping down my face, nose and chin I swallowed the cum in my mouth then began licking the tip of his cock enjoying my friends man juice.

 

I looked up into his sweat-drenched face. His eyes were closed as if he had passed out. His chest was heaving up and down as he tried to catch his breath. Ten red scratches ran down his chest to his stomach from my fingernails.

 

I sucked his cock in one more time sucking off any cum that remained. Then pulling my mouth off his cock as it began to shrink. Standing up wiping the cum off my face with my fingers watching his face. He opened his eyes and I began rubbing his cum all over my breasts, playing with my nipples. Pinching my nipples one last time. I bent down and picked up my blouse.

 

“Kacy says Happy birthday!” I said in a soft voice as he sat there naked from the waist down and bare chest exposed.

 

“Julie, that was the most incredible present anyone could have ever given me. Thank you!”

 

“Don’t thank me. I did it for my brother. Goodnight.” I said then staggered topless to the house leaving him to get dressed and pick things up.

 

Once in the house I went to my room and gazed in the mirror. I had cum smeared all over my face and chest. I could feel it pulling on my skin as it was drying up. I laid back on my back on my bed and closed my eyes. The room was spinning and so was my feelings. Tears flowed out of my eyes out of happiness. 

 

After a few minutes I opened my eyes and dried my tears with the back of my hands and looked at the clock. Nine o’clock it read, so I finished undressing and put my robe on and stumbled downstairs to get something to eat. I was so hungry. I heated up some left overs from the night before and sat down and ate.

 

Grabbing a bag of chips I went back upstairs and laid back on my bed. The whole room was spinning out of control. All I could think about was how I pleased my best friend Wayne.

Removing my robe I crawled under the covers, closed my eyes and soon faded away.

I had gotten through the first three hours with no problem, but when I got to my fourth hour my heart started to race. See my fourth hour teacher Ms. Winters was one of the hottest girls I had seen on the planet, she had a nice rack and a nice ass. I usually had to hold myself back otherwise my secret would be out and everyone would know. I sat down in my desk which was right next to Kenzie's and prepared for the class to start. Right on the dot Ms. Winters walked in but today she was wearing a low-cut shirt and a rather tiny skirt. I could feel my dick slowly start to grow in my thong and jeans. Kenzi looked over to see what was wrong because I had a worried look on my face. She looked down and saw something she didn't expect "Ermmm Sarah.. what's that?" she asked pointing to the bulge in my pants. "Nothing!" I said loudly and got up and walked quickly out of the class. Luckily no one saw me but Kenzi and the teacher. I headed to the bathroom and headed into a stall to wait out my boner. They didn't last that long usually. "Sarah..?" I heard a voice call outside of my stall. "We need to talk" I said quietly. I headed out of the stall to find a curious Kenzie. "What did you see..?" I asked frightened. "Well.. I saw something in your pants... what are you? I mean are you a boy or a girl?" "A girl!" I answered immidetly. "Then why do you have a penis?" she asked hessitantly. "I was born with it, want to see? I can prove I was" she nodded and I grabbed her hand and lead her into the handicapped stall (that could fit seven people in it). I slowly undid my pants, and pulled down my thong revealing my dick. Relaxed it was a good six inches and erected it was around 9. "Oh my god!" she said stunned. "Can I touch it?" she asked with a grin on her face. That got me really excited and I nodded quickly. She approached me slowly and reached her hand down towards my dick which was starting to grow.

"You like me touching it?" she asked seductivly. "Yes.. yes I do!" I replied. "feel free to do more" I said in hopes of her doing so. Which of course she did. She kneeled down and wrapped both of her hands around it. "Mmm" I moaned softly. "Suck that dick" I said with a grin. She wrapped her warm mouth around my fully erected dick and slowly she started to take it all in her mouth. "Oh god!" I moaned loudly. "Suck it.. harder suck it you dirty hoe!" she countinued to suck it quicker and harder. It being my first time I was extremely horny and very excited so I reached the point of no return quicker then when I masturbated. "Oh shittt! I'm gonna come!!" I shot my load into her mouth and suprisingly she took it all in and swallowed it.

Thankfully no one heard us. Now our friendship is very different.. and we've done it many other times.

;]

 

            A woman came into the store a little after lunch time. She was wearing a halter top with a short skirt, stockings and heels.  Adam went over to her and asked if he could show her anything. She said she needed a new pair of shoes for a party she was going to attend this coming Saturday. She wanted to see shoes with a four inch heel in Silver size 11M. Adam went to the back and came back with four pairs of shoes. He decided to take a peek up the woman’s skirt while he was fitting her with the fourth pair of shoes. He noticed that she was wearing thigh high stockings, but she wasn’t wearing any panties. She caught him looking up her skirt. She just lightly tapped him on his head and asked him if he liked what he saw. Adam just simply nodded in the affirmative with a sly grin on his face. She said, “I’m Nyssa and I’ll come back at closing to give you a full view.” She left after purchasing one pair of shoes. Adam returned the other pairs to the back wondering if Nyssa would indeed come back.

 

            The rest of the day was like the beginning. All the women came in dressed in slacks. Adam kept wondering if Nyssa would come back.

 

            It was closing time. Adam had closed out the register and put the money in the safe. He then let his night clerk out the door. He locked the door and then did is final check. He heard a slight tap at the door. It was Nyssa with a small tote bag. She came back as promised. He let her inside. She asked if there was somewhere in the store that would be private. He nodded in the affirmative, and led her to the office in the back after relocking the door.

 

            As soon as they entered the office, Nyssa spun Adam around and gave him a passionate kiss, and then whispered in his ear, “We are going to have some fun.” Nyssa leaned against the desk and removed her halter top exposing her medium sized breasts while Adam was getting over the initial shock. She said, “Suck my nipples.” Adam attacked her nipples like a hungry infant. She said, “Gently baby gently.” He slowed down. He then started swirling his tongue around her nipples. “Oh baby that’s good, “she moaned. She then reached under her skirt and started playing with herself.

 

            “Ok baby stop sucking my nipples. I want you to get undressed for me, “she said after she stopped playing with her self. Adam did as he was told. Nyssa noticed that Adam’s cock was a little hard. She grabbed it and started gently stroking it. Adam started to moan with pleasure. She kept up the gentle motion until she felt a little leakage. She stopped and said, “I don’t want you to cum just yet. Sit on the desk while I put on a little show for you.” She started to dance and started to strip out of her skirt.

 

            Nyssa slowly inched her skirt downward. Adam’s eyes followed her every movement. Eventually, her skirt was low enough to reveal a slightly erect cock. “I told you that I was going to give you a full view,” she said in a low sexy voice. Nyssa continued dancing until she was completely out of her skirt. She then stroked her cock until it became half erect. Adam’s eyes were fixed on her cock. She guided his head to look into his eyes and said, “now the real fun is about to begin.”

 

            Nyssa reached into her tote back and brought out a rubber glove and a container of lube. “I need your asshole well lubed for what have I mind. Be a good boy and turn around and lean on the desk for me,” she told Adam. She put on the glove while he was turning around. She lubed up the middle finger of the glove. She slowly penetrated his asshole with her finger. He moaned while her finger went deeper inside. Nyssa started moving her finger back and forth once it was in all the way. She even twirled it around a few times. She kept this up for a few minutes. Both of their cocks grew harder.

 

            Nyssa said, “I think you are ready for the next stage” as she removed her finger, and then the glove. She reached into her bag and removed a seven inch dildo. She lubed up the dildo and she stroked it to get it coated with the lube. She inserted it into Adam’s asshole and he moaned again in pleasure. Nyssa pushed the dildo in as far as Adam could take it. She used the same technique as she did with her finger. She started slowly and gradually went to a faster pace. Adam continued to moan in pleasure as the dildo kept going in and out of his ass. Nyssa kept shoving the dildo in and out of his ass until she had a complete hard on.

 

Nyssa said, “I think you are ready for the final stage” as she removed the dildo. She reached into her bag for a condom. “I like to be safe,” she said while putting on the condom. She inserted her dick into Adam’s asshole. He let out his loudest moan. She pushed it in as far as Adam could take it. He continued to moan. Nyssa started thrusting her cock slowly at first. Adam started moaning louder still when Nyssa quickened her thrust. Nyssa continued her thrust at a faster pace and then Adam cried out, “My cock feels like its going to explode. I need to cum.” Nyssa replied, “I’ll take care of it as soon as I finish.” Nyssa continued to pound Adam’s ass until she shot a forceful load.

 

“I do enjoy fucking a young man’s ass, “she said as she slowly removed her cock. She peeled of the condom and tossed it into a nearby wastebasket, and then said, “Now let me think. What am I going to do with that hard on of yours? I know what I could do if we were at my place. I’m not going to let you suffer until I get you there. Turn around.” Adam did as he was told and she grabbed his cock. “My you do have a hard one”, she said. Nyssa always liked seeing a hard cock on a man after she fucked him. She started stroking his cock. “Please make me cum,” he begged. She replied, “Since you asked nicely and have been a good boy, I am going to jerk you off. Sit on the edge of the desk.” Adam complied. Nyssa reached into her bag for another condom. She said, “This is so that we won’t have any mess to clean up” as she was putting the condom on Adams hard dick. She started with slow strokes. Adam began to moan again. She stroked faster and Adam’s moans once again became loud. All of a sudden Adam yelled,”I’m Cumming!” Nyssa could see the condom filling up with his hot juice. She gave Adam a few hard strokes to squeeze out the remaining cum. She peeled off the condom once Adam’s cock started going limp. The condom joined the other one in the wastebasket.

 

They both got redressed after they rested for a few minutes. Adam led her out of the office and then let her out of the store. Nyssa gave him a quick peck on his cheek and a slight grab on his ass. She whispered in his ear, “Maybe I’ll come by again and take you to my place.” She left and proceeded to her car. Adam waved goodbye as she drove away, and she blew him a kiss. Adam relocked the door. This was one night he will not forget.

 

Adam finally lived out a fantasy of his. He always wanted to have sex with a she male every since he bought a she male video. Adam bought a video once based on the title. He did not know what the movie was about. The movie had scenes of she males fucking men, and she males fucking women. Adam became turned on while watching this video. This was his favorite movie to jerk off with.

 

Adam left the store after he gathered his belongings. He wondered if Nyssa will ever come back once he got in his car. Adam was happy. He lived out a fantasy or is it possible that his life has changed?