Published Sex Stories / transgender-stories

Mano Ka'ao

uosdwisrdewoh on Transgender Stories

The plane descended toward the islands. They looked like beautiful green jewels in the deep blue ocean. Cindy felt like bouncing up and down in her seat. She was home!

Cindy's mother was a native Hawaiian and had lived on the islands all her life but shortly after Cindy was born she took a job in Chicago and hadn't been back since. She would never say why.

Cindy just felt drawn to her native soil. She'd always been a beach bum, weather permitting, and was a star swimmer in high school. She constantly read surf magazines too and was dying to give it a try. She had been bugging her moher as long as she could remember to take a trip there. Then finally for her eighteenth birthday Cindy's mom surprised her with a ticket. She could stay with her grandmother in Hawa

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ii for the whole summer before starting college!

Cindy stepped off the plane and a beautiful Hawaiian girl in a grass skirt and flowery bikini top put a lei around her neck.

"Aloha! Welcome to Hawaii!"

She leaned in and kissed Cindy and their breasts briefly touched.

"Aloha. Thank you." Cindy said, mesmerized by the girl's large dark eyes.

She wished she could stay here and kiss this sexy wahine some more. But the line kept moving and of course she didn't know if this beauty even liked girls or not. But she knew the beaches would be covered with beautiful women and men. She was going to love Hawaii!

Across the room she saw the sweet little old lady she knew only from pictures waving at her. She ran to her.


"Cindy, Ipo! You're even prettier than your pictures! Aloha, welcome home!"

They grabbed Cindy's bags, she packed very light, little more than swimsuits, and left. But there was one thing she needed. They stopped at a surf shop before they even got to her grandmother's little house.

Cindy pretty much lived on the beach for her first two weeks. There were beautiful people all over. She made lots of friends and had lots of fun, light flirtations but mainly she was in love with the surf and the sun. She took to surfing like she'd been doing it all her life and was seriously thinking about entering some competitions. She knew this was where she belonged.

Then on the night of the full moon her grandmother asked her if she would come to a ceremony at a very ancient heiau shrine. She was interested but a little nervous. Cindy hadn't grown up with any kind of religion and was basically an agnostic. But it seemed important to her grandmother so they drove to the other side of the island and were now hiking across a long beach.

"Are you sure I'm dressed okay, Kupuna?"

She was wearing only her favorite blue bikini. Grandma had on a traditional grass skirt.

"You're fine, Ipo. Your clothes don't matter at all."

They climbed up over some lava formations and then splashed down into knee-deep water. Cindy's grandmother turned on a flashlight and led her into a cave. It was a long tunnel that stretched back farther than Cindy could see.

"This is amazing, Grandma! What is it? Some kind of lava tube?"

"Yes. It is a holy place made by the Akua."

They walked deep into the tunnel and Cindy saw light coming around a sharp turn in the tunnel. They rounded the corner and Cindy was startled to see that the tunnel widened here and was packed with people. They were all native Hawaiians. Some were her grandmother's age but many were younger. All the men and some of the women were bare chested in the flickering torchlight. She smelled some kind of incense.

A very handsome man with broad muscular shoulders held out his hand to help her out of the water.

"Aloha, Cindy."

"Aloha." How did he know her name?

All eyes were on her. She knew she was dressed wrong for this. Then an older woman stepped forward and started chanting. Everyone in the cave joined in. Cindy didn't know what to do. She only knew a few words of Hawaiian and nothing about this ceremony.

The old woman poured a dark liquid into a cup and held it out to Cindy. She took the cup timidly.

"'Awa." Her grandmother whispered in her ear. "Drink it all."

"Is it alcohol?" Cindy sniffed it experimentally. No, not alcohol. It smelled really bitter.

"No. Much better."

Cindy gulped the 'awa quickly and handed the cup back. It was terrible.

No 'awa was offered to anyone else. The cup and the bottle disappeared and the chant changed. It became louder and more intense. Cindy realized that this ceremony was all about her.

But she wasn't nervous anymore. She felt really good. They all started to dance a hula dance and Cindy danced with them. Her dancing was much more contemporary, however. She was starting to feel horny. The sweaty half-naked bodies rubbing against hers felt so good!

Hands were all over her, undressing her, and she loved it. She writhed and danced through all these people completely naked and unselfconscious. Two men stepped up to her. One was the hunk who'd greeted her. They scooped up handfuls of goop from a pot and started smearing it all over her.

The guy in front of her squeezed and carressed her greasy breasts. She jumped into his arms and rammed her tongue down his throat. She felt his hard dick against her hot swollen cunt through his thin grass skirt. She wanted to fuck him NOW!!

He gently pried her off of him and stepped away but he didn't look at all happy about it.

She was starting to feel weird. Well, weirder. Her skin was tingling all over, especially between her legs. Her head was spinning and she was hornier than she'd ever been in her life! No one seemed willing to have sex with her. She felt like she wanted to just rape somebody. But instead she put all her frustrated sexual energy into her wild, thrashing dance.

She grabbed an extremely pretty girl and kissed her while groping her luscious bare breasts just before she started to feel really dizzy. She staggered a few steps and then fell backwards into the water.

Cindy woke up on the beach near her grandmother's house. She was exhausted but felt wonderful. She was also naked and didn't see her swimsuit anywhere. It was still dark but she could tell morning was not far off. She had no idea what had happened last night. Hadn't Grandma taken her to a shrine? All she could remember was incredibly vivid dreams. Swimming and swimming and never needing to come up for air. She remembered hunger. She remembered chasing schools of little fish and catching them in her teeth, devouring them whole. This was too weird.

Well, one thing she knew. She needed to pee bad. Well the best way was simply to walk into the ocean so she stood up, reaching between her legs...and screamed. She looked down in horror, thinking she'd been mutilated somehow. She couldn't believe what she was seeing, a big beautiful dick. She pulled on it, not believing it was a part of her. But it was firmly attached. She cupped the balls underneath and probed her pussy with her fingers. She was intact. She just had something extra. Somehow.

Having to go to the bathroom bad enough can motivate you regardless of any circumstances so she just held on to the new dick and let it go. Peeing standing up(out of the water) was kind of fun.

Now she had to get home. It was twilight but not exactly dark and she was over a mile from her grandmother's house naked on a beach with nothing but a few leaves. Well, it wasn't getting any darker. She would have to find something along the way.

She started walking and found that she didn't feel embarassed at all. She was proud of her strong, sexy young body. And she wasn't even that alarmed by her new equipment any more. If someone saw her they saw her.

On the long walk she experimented with her fantastic new genitals. Stroking her dick and rubbing her balls felt so good! And she was very well endowed. When it got hard in must have been ten inches! She imagined some sexy wahine down on her knees sucking it. Or for that matter some guy.

She moaned and shot her load onto the road. God, that felt good!! She wiped the the cum off the bottom of her dick and sucked on her finger. Mmm, delicious!!

The sun was coming up when she got to her grandmother's house. She found Grandma sitting at the kitchen table.

"Good morning, Ipo." She didn't seem at all surprised to see Cindy walking in naked at sunrise.

"Kupuna, what happened last night? What's this??" She pointed to her dick.

Grandma looked down at the dick, noticing it for the first time.

"Ule. Oh yes, that happens sometimes. It's a sort of side effect. Sit down Cindy. I must tell you a story.

"You love the water don't you?"

"Of course."

"Did you ever feel like you could almost breathe under the water."

Cindy thought about it. "Sometimes. I can hold my breath for a really long time. Why?"

"Your mother told you your father died when his fishing boat sank. The truth is your father was an 'aumakua. He was a shark spirit.

When your mother became pregnant with you he told her the truth. Your mother never believed in the old spirits and she was scared. She told him she never wanted to see him again. When you were born he came to see you. He wanted to take you into the ocean. Your mother refused because she was afraid he'd take you and never bring you back. Soon after that she left the islands and never came back."

"So I'm-"

"Yes. We are all related to sharks but you are both. Just as you are now woman and man. You can change if you try."

Cindy held up her hand. She concentrated on the way she'd felt last night, wild and dangerous. Before her eyes her hand grew! Her skin turned a dull, scaly gray and webbing grew up between her fingers. Her nails became long and pointed and hard.

She got scared and the transformation immediately reversed itself.

"That was very good. You just need to relax and let it happen.

"I knew you would never really be happy away from your native waters, never knowing your true nature. That's why I convinced your mother to let you come here."

Cindy stayed in the house all day practicing her transformation. She could turn herself into a huge shark but she had to quickly change back because her gills burned for water. She could also stop the transformation at any point along the way from human to shark. This was incredible!

At dusk she jogged down to the beach,her new genitals a bouncing bulge in the front of her bikini bottom, threw off her clothes, and dove into the water.

She transformed completely into a massive twelve foot shark and shot through the water like a missile, propelled by her powerful tail. She explored the ocean in ways she had never been able to, even with scuba gear. She snapped up fish by the dozen and swallowed the chunks whole. She'd never felt so powerful or so right in her life.

She swam near a beach, hugging the shore when she heard the scream. Since the ritual transformation her senses were all extremely sensitive and she had excellent hearing even in her shark form. She slipped up onto the beach and grew legs to investigate.

She saw a white guy and girl thrashing around on the sand. Her dick(three feet long in this massive form) stood straight up at the sight. But something was definitely wrong here. She could smell fear and the girl screamed again.

"No!! Get off me!!"

Cindy roared and ran forward. Her claws sank into the guy's shoulder and he screamed as she threw him across the beach.

She looked down at the girl. Her long blond hair was in her face and her breasts were bare in the moonlight. She pushed her hair out of her face and looked up at Cindy with wide blue eyes. She screamed louder than ever. Cindy backed up a step to show that she meant the girl no harm. Her dick continued to stick straight up. Not much chance she'd get to put it in this girl though.

The girl continued to scream as she jumped up and ran down the beach as fast as she could.

Cindy was horny and needed to stick this dick in something now! She turned and saw the guy running down the beach in the opposite direction. Perfect.

She caught him easily. She grabbed hold of him and slashed his swim trunks to ribbons. He screamed like a little girl. Cindy shoved his face down in the sand with his ass sticking up in the air. She grabbed her three foot dick. No, that was a little much. She didn't want to kill him.

She shrunk her dick down to a mere foot long and slammed it into his helpless ass. He shrieked as she entered him and continued to scream as she pounded his ass mercilessly.

I'm letting you off easy, boy! I'm

She slammed her dick into him up to the balls and shot her fish seed inside him. She slowly pulled her dick out of his abused ass and looked down at him whimpering in the sand. Pitiful.

She turned and walked back to the water, eager to get back to swimming and find herself some food.

Two days later Grandma dropped a newspaper in front of her. The headlines said "MONSTER" ATTACKS COUPLE ON BEACH.

"Was this you??"

Cindy giggled. "I didn't hurt the woman. He was trying to rape her. I only gave him what he deserved."

"Well, you just be careful! Just because you're strong doesn't mean you're invincible."

"I will. I will." Cindy said, stiffling more giggles.

Now Cindy patrolled the waters around her island every night. She felt like a superhero.Though a constantly hungry and horny superhero.

She was swimming down deep, admiring the beautiful coral when something made her glance up.


No, wait. That was a surfer.

Suddenly another huge shark, even bigger than her, shot past her and rammed the board from underneath. A woman screamed. Another damsel in distress.

Cindy raced after the other shark. She caught up to it and took a huge chunk out of it's tail. The shark turned and slashed at her with it's teeth. They sliced deep into her pectoral fin.

Cindy retreated and the shark tried to follow, limping along on it's mangled tail. She literally swam circles around it. The blood filled water was driving her crazy! She charged the other shark from above, ripping it's gill. It tried to turn and snap at her but she was much too fast.

Now she moved in for the kill from underneath. She disembowled the shark with one long slashing bite and went into a complete feeding frenzy.

Then through the haze of blood she saw the surfer. She was floating facedown with her long black hair floating in a halo around her head. Cindy made herself stop feeding and swam to the girl. She quickly grew arms to hold the girl and carry her back to shore.

She laid the girl gently on the beach. She was a beautiful Hawaiian girl and she was completely naked. Cindy pushed her hair out of her face. She wasn't breathing.

Cindy reverted to her completely human form and pressed her mouth to the girl's soft lips. She squeezed her nose shut and breathed into her.

Her shoulder ached but she saw that the wound was only a deep scratch now and that it had already stopped bleeding. She worked to revive the girl for more than five minutes. But it was no use. Her battle with the other shark must have gone on much longer than she thought and the girl swallowed too much water.

"Damn it!" She yelled with tears in her eyes.

She leaned down and pressed her lips to the girl's one last time. This time to kiss her. "I'm sorry. I tried."

The girl coughed salt water into her mouth.

"You're alive!!"

Cindy sat her up to cough up all the water in her lungs then cradled her head against her breasts, stroking her pretty hair.

"It's okay. I've got you. It's okay." She whispered soothingly in the girl's ear.

Finally the girl said "Thank you. I think I fell off my board and hit my head. At first I thought there was a shark but if there was I'd be dead right now.

"I know it's stupid to surf by myself at night but I just feel like I need to get in the water sometimes you know?"

"I understand." Cindy said.

The girl reached up and touched her bare breasts. "Where's my suit?"

"You weren't wearing it when I pulled you out."

"It must have come off in the water. That one fits terrible." She sat up and looked at Cindy. "So...where's your suit?"

Cindy giggled. "That'll take some explaining. I'm Cindy."

"I'm Aliikia. You can call me Ali."
"That's such a pretty name. Sometimes I wish I had an authentic Hawaiian name like that."

"Cindy's a pretty name too." She threw her arms around Cindy's neck. "Thanks again for saving me."

Cindy hugged her back, feeling their bare breasts pressed against each other. Her dick was getting hard again.

Ali moved back a little with her arms still around Cindy's neck. She looked deep into Cindy's eyes. Cindy felt like she was falling into those dark, beautiful eyes. Then they were kissing and groping each other passionately.

Ali's hand found Cindy's dick and she looked down in surprise.

"You're...not wahine, Cindy?"

"Sure I am, baby." Cindy guided her hand between her legs and gasped as Ali fingered her clit. "I just have something extra. I hope that's okay."

"Okay? It's amazing!" Ali grabbed her dick and started stroking it.

Cindy moaned as Ali leaned down to lick her breasts. Then she dropped to her knees and started kissing and licking her dick.

"Mmm, it's so big!"

Her head started bobbing up and down as she swallowed as much of Cindy's dick as she could. It felt so fucking good!! Cindy couldn't take it anymore! She grabbed Ali's head and jammed her dick down her throat. Ali gagged and struggled but Cindy held her tight as she shot her cum down her throat.

Cindy came to her senses and pulled her dick out.

The poor girl just almost drowned and now I'm choking her with my cock!!

"Ali, I'm sorry!"

Ali coughed and looked up at her with those beautiful eyes and with cum dripping down her chin. "Sorry?? That was incredible!!"

Cindy grinned. "Oh, then you'll love this!"

She got down on her knees and pushed Ali onto her back. She leaned down and kissed her, loving the taste of her cum on her lover's lips. She moved down to her large, upthrust breasts and sucked her dark nipples. Then she was between Ali's legs with her face buried in her cunt. She tasted so good Cindy could do this all night.

"Oh! Fuck me, Cindy! Stick that big beautiful cock inside me!!"

Cindy was happy to oblige. She thrust her enormous hard cock into Ali, making her scream half in pleasure, half in pain, and started pumping it in and out of her. Ali's long, beautiful legs wrapped tightly around her. She understood now why guys like that so much.

She was so tight! Ali was breathing hard and her nails raked Cindy's back and breasts as Cindy fucked her.

"Oh yes! Yes! God you're big!" (This was partly because Cindy's dick actually grew a bit as her passion increased.) Ali screamed and arched her back as Cindy came inside her.

Cindy pumped all her cum into lovely Ali then laid down in the sand next to her. They fell asleep holding each other, lulled by the sound of the waves.

They woke up a couple of hours later and snuck to Cindy's house under cover of darkness. Ali giggled and felt wonderfuly naughty walking down the road naked. They spent the rest of the night and most of the morning in Cindy's small bed.

"Where are we going, Cindy??"

Cindy turned and smiled at her beautiful girlfriend. She looked angelic in the light of the full moon. They were dressed similary in small bikinis. She pulled Ali close and kissed her.

She'd spent every moment with Ali since they met and was completely in love with her. She'd learned that Ali was an orphan. Her mother had died in childbirth and she'd never known her father. She'd lived on the islands all her life and was attending the University of Hawaii in the fall. Cindy, of course, had promptly applied at U of H.

"Don't be mad at me, Huapala, but I think we had the same father."

"The same father? What?"

"Don't worry. It's not on our birth certificates. We can still get married." She took Ali's hand and led her into the cave. "This is an ancient heiau. I just had to show it to you!"

Her sharkness told her.
hungry too! She thought. Too bad she couldn't tell him that through this huge mouth full of razor-sharp teeth.

Shemale Slut Part 2

katsings on Transgender Stories

Since our first encounter Leslie (that is her name) and I have spent a lot of time together.  Mostly in the Boutique before opening and after closing.  I can't seem to get enough of that beautiful cock and she knows it.  She has even come to the Boutique on her off days and called me into the dressing room to get a taste.

One of our most recent encounters happened before the store opened.  I was asked to come in early to take inventory and Leslie came in to meet with the owner.  I arrived before she did and when she walked in the door I immediatley got turned on, as I usually do, whenever she is around.  She has a way of looking at me that just makes me melt.  Literally, my pussy gets soaking wet.  She asked me wh

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ere was the boss.  I told her, she was in the office waiting on her.  She said, "I bet."  Before going in, she asked me if I had on any panties.  I told her I was wearing one of the thongs that she purchased for me.  She said, "good girl",  kissed me on the lips and headed into the office.  Still in a trance, I came to when I heard voices coming from the intercom system on the counter.  What I was hearing was blowing my mind and turning me on. 

The owner was definitely waiting on her, because they wasted no time getting it on.  Someone mistakenly (yeah right)touched the intercom button giving me full verbal access to what was going on.  I heard what sounded like kissing at first.  I heard the owner say that she missed her kisses but most of all missed "this."  I knew right away what she was talking about.  That cock had a mesmerizing effect.  The owner must have went right to work on that rock hard cock, because I heard Leslie telling her how good her mouth felt.  After a little more sucking, Leslie told her that she was ready to ram deep into her pussy.  The next thing I heard was Leslie asking her if it felt good and the owner screaming out "yes, yes".  By that time I had taken hopped up on the counter and was using two fingers in my pussy imagining that cock was going inside of me.  Oh how I wanted it inside of me.  After a few more minutes I heard Leslie tell her that she was "coming."  I heard moaning and grunting and the owner telling her to "give it to me."  After Leslie had finished coming and had plopped our of the owner's pussy I heard Leslie tell her that she wanted their "cum" to dry on her cock.  The owner obviously was about to  assume the position between the those beautiful legs.  The owner told her "okay" with a confused tone.  I heard the owner say she was going in her bathroom to take and shower.  Leslie kissed her goodbye and said she was headed back home and would shower then.  As I was hopping down off of the counter, I heard the intercome cut off and a few seconds later Leslie walked out of the office with a wicked smile on her face.  She walked straight to the dressing rooms and becked for me to follow her.

By the time I arrived in the dressing room, she was already sitting on the bench with her skirt (after our first encounter, she told me that we would always skirts to work for easy access) raised and her legs spread wide with that COCK hanging and begging for me to suck.  She stopped me as I was walking towards her and asked me "how bad do you want it."  I told her "I want it "bad".  She told me to get on my knees and crawl to her.  I was happy to oblige.  I got down on my knees and crawled to that COCK that I knew was covered with a mixture of her cum and our owner's cum.  When I arrived between her legs I grabbed and gobbled her cock so fast she laughed and told me to slow down.  I couldn't because it tasted so good.  The mixture was intoxicating and I was loving it.  As I was sucking she was talking dirty to me and asking me if I enjoyed listening to their sex adventure.  I nodded "yes" not wanting to take her cock out of my mouth.  After a few minutes of sucking, she stopped talking and gradded my head.  As she was fucking my mouth, I gagged a few times, but I didn't stop.  When she told me she was coming, I locked my jaws around that COCK because I wanted every drop of cum.  She came so hard I couldn't contain her in my mouth and it slipped out and spewed all over my face.  When she finished, she quickly leaned down and started kissing me with a passion that I have only felt with her.  Leslie licked up every drop of her cum that was on my face as I lifted up on the bench next to her.  When she finished licking, she looked me in the eyes and told me that she had to leave but wanted to satisfy my wet pussy.  With that she put her hand under my skirt and dipped her finger in my wet pussy, then took her finger and put it in her mouth.  She kissed me agian, told me to come to her house when I got off and with that she left.  As I straightened myself up and was headed out of the dressing room, I ran into the owner.  She had a very satisfied look on her face.  I had the same look on my face.  Just sucking Leslie's cock satisfies me.  I went to the bathroom, got myself off and washed up before the store opened. 

Later in the day while I was waiting on a customer, the phone rang.  It was Leslie and her voice made my pussy twitch.  She asked me if my pussy was still wet.  I told her "yes".  She told me that her cock was rock hard and waiting for me.  When she said that it felt like I was about to have an orgasm, but I had to keep myself composed in front of the customer.  She told me that she was also going to see about us having a threesome with the owner.  With that she hung up.  I was weak at the knees.  I was grateful that the customer was engrossed in a conversation on her cell phone, so she didn't notice me.  I couldn't wait for my shif to be over.

Stay tuned for more...

Cheering up (part 1)

sprky77 on Transgender Stories

I was sitting by myself at the bar starring at my drink when a very beautiful redhead sat next to me.  I didn’t notice her until she asked, “Why are you looking so down tonight?”  I really didn’t know what to say.  Most of the time I just sit there and no one even talks to me.  I am usually a shy and quiet person and that night was no exception.  So, needless to say I was quite surprised when a woman this beautiful initiated a conversation with me.  At first I stuttered and stammered a lot and basically said nothing intelligible.  She said, “My name is Ginger, why don’t you buy me a drink and we can talk about what is bothering you.”  Well I didn’t know what to s

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ay so; I ordered us each a drink.  She was very nice and had a very caring demeanor about her.  We started drinking and talking and as the night went on I began to loosen up.


            The more we drank the faster time went by and next thing I knew the bar was closing.  Ginger said, “Why don’t you come over to my place and we can continue this conversation?”  This usually doesn’t happen to me and I really didn’t know how to respond.  I said, “Sure, why not?”  So, we got up from the bar and went out to our cars and I followed her to her place.  When we got to her place she invited me in and told me to have a seat and relax while she fixed me a drink.  So, I went over to the sofa and sat down.  Her living room was very unique in how it was set up.  There was a metal pole behind the couch that was bolted to the ceiling and the floor.  The couch was firm but comfortable and the ambiance was very comforting.  Ginger brought me my drink and sat down beside me.  She was very soft spoken and when she talked she had a special way of making me feel good.  I was really starting to loosen up now as Ginger leaned in to kiss me.  Wow!  It was so soft and passionate.  I had never been kissed like that before.  She slowly slid up on my lap as she kissed me and wrapped her arms around my head kissing me more and more vigorously and passionately.  Things were really starting to heat up when the doorbell rang.  She said, “excuse me” and jumped up to answer the door.  Talk about depressing, things like this don’t happen to a guy like me everyday.


            She went over to the door and opened it far enough to see who was there.  I could hear a couple of ladies outside and she let them in.  They were both very beautiful also.  She invited them in and they came over and sat on the sofa next to me.  She introduced the blonde as Jessica and the Asian as Mia.  Stupid me said, “hi, I am really excited to meet you.”  They giggled and said, “We can tell” as they were starring at my pants.  I definitely was starting to get really excited.  Ginger said, “You seem really depressed tonight so I thought I would invite a couple of friends over and see if we could cheer you up.  Grinning from ear to ear I said, “It is working, you are definitely starting to cheer me up.”  Ginger went and got some more drinks while I got to know Jessica and Mia.  When Ginger returned Jessica and Mia were sitting on each side of me rubbing my shoulders.  I was in heaven.  We drank a few more drinks and I was feeling really good when Ginger said, “we want to entertain you and make you feel good.”  I said, “I am game, how are you going to entertain me?”  They told me to sit back and relax while they went into the bedroom to change. 


            A few minutes later the stereo kicked on and the girls came dancing out of the bedroom in some really sexy lingerie.  They were hot as they danced there way over to me.  Ginger came over in front of me and started doing a strip tease while Jessica and Mia dirty dancing with each other.  I was really excited now and couldn’t wait to see what else was in store for this night.  Ginger slowly grinded her ass up against my crotch making my cock rock hard.  When I put my hands on her back she turned around, took my shirt off, and put my hands behind head and hand cuffed me to the pole behind the sofa.  This was very odd, kind of scary, yet interestingly exciting.  She went back to her strip tease striping down to her panties.  She had the most firm and perfect tits I had ever seen.  She danced her way on to my lap grinding her ass on my crotch the whole time and then she smothered me with her tits before allowing me to gently suck on each perfect nipple. 


            Meanwhile Jessica and Mia were undressing each other.  Kissing and seductively caressing each other as they went.  This was the most exciting moment of my life.  Three hot women dancing and taking their clothes off for me, what more could a man ask for?  Wow, life just couldn’t get any better than this.  All three of them were stripped down to their panties and they were starting to take my pants off.  First one leg and then the other. Then they took off my socks and my boxers.  I was rock hard and ready to explode.  This really turned them on and they told me that seeing me like this really made them wet.  Then Ginger says, “I want you to wear this blind fold while we prepare to rock your world.”  I agreed and she put it on.  Now I can’t see and I can’t move my hands.  For some odd reason this excited me even more.  Next I felt one of the girls slowly start caressing my cock and playing with my balls.  Mia straddled my chest and put her tits in my face and allowed me to suck on her nipples while she whispered in and nibbled on my ears.  Then I felt Ginger join Jessica.  Kneeling between my legs she spread them wide open and started to lick my cock.  It was perfect, two beautiful women licking and playing with my cock while a third was smothering me with her tits and nibbling on my ears.


            Gingers voice was so sexy and soothing when she talked and she constantly talked to me letting me know what was going on as she was doing things.  I felt so relaxed with her and she knew it.  She started to lick my ass while Jessica sucked on my cock.  At first it felt kind of strange and then she put some lubricant on her finger and slowly started putting it in my ass.  She told me to let her know if she hurt me.  I had never had anyone play with my ass before so I wasn’t used to it.  She was very gentle as she slid it in very slowly.  She kept working on my ass slowly getting up to three fingers sliding in and out of my ass.  After the pain of the initial stretching it started to feel real good and got me even more excited.  Next, I heard a vibrating noise and Ginger said, “This will help relax your asshole.”  I didn’t really pay attention because I was deeply into Mia now as we were making out passionately.  Ginger kept working my ass with the vibrator, while Jessica was giving me the greatest blow job of my life stopping periodically to keep me from cumming, and Mia had her tongue deep down my throat playing tonsil hockey.  I wished my hands were free so that I could get more physically involved, touching and caressing them. 


            With that said, Mia stops kissing me and I feel her turn and look at Ginger and Jessica.  They all three giggle and Mia asks, “how would you like to lick my wet juicy pussy?”  I say, “I have been looking forward to that ever since you walked through the door.”  Ginger asks, “Has anyone ever fucked you in the ass with a strap-on before?”  I say, “no, but right now I am willing to give it a try.”  They all giggle again.  Ginger tells Jessica to go down on my cock while she slowly slides the strap-on in my ass.  She says it will make me forget about any pain I might feel.  She was right to; I didn’t feel a thing as she slid it in.  Meanwhile, Mia says, “open your mouth wide and stick your tongue out so I can stick my wet juicy pussy on it.”  As she grabs the back of my head, I start to notice that the strap-on feels kind of like a real cock and all of a sudden I feel a giant cock go in my mouth and touch the back of my throat.  Mia holds my head while I gag on it for a second.  Then she starts moving my head up and down on it while she fucks my face. 


            I tried to grab her with my hands and pull her cock out of my mouth but my hands were cuffed and I couldn’t get free.  I felt violated but, at the same time it excited me even more.  Every time Ginger would ram her cock in my ass, my cock would go deeper in Jessica’s mouth.  Pretty soon they all had a really good rhythm going.  Everyone was fucking or sucking something and I was fucking, sucking and being fucked.  The passion and moaning got very intense and lasted for quite a while.  Ginger and Mia started fucking me faster and harder and Jessica started massaging my balls as she sucked harder on my cock.  All of a sudden Ginger rammed her cock as deep in my ass as she could and held it there as I felt her hot cum ooze from my ass around her cock.  Mia grabs the back of my head and shoves her cock down my throat and I feel her hot cum coat the back of my throat causing me to fire mine down Jessica’s throat.  I had never felt anything so intense before in my life.  As everyone relaxed from the intense moment, Jessica says, “open your mouth, it is my turn to surprise you.” 


On that note Mia took off the blind fold and got out of the way.  Jessica climbed up on the sofa and straddled my chest.  Now, I could see what was coming.  She had one of the biggest cocks I had ever seen.  As she went to put it in my mouth I closed it and shook my head saying there is no way you are going to put that massive thing in my mouth.  Jessica said, “Shut up bitch and open up.  You are going to suck my cock. You owe me after the blow job I gave you.”  Then she grabbed the back of my head with one hand and forced my jaw open with the other shoving her cock in as far as she could.  She violently fucked my face until she shot her massive load of hot sticky cum down my throat.


            All three of them sat on the sofa looking at me trying to see if I enjoyed it or not.  Ginger asked, “Well, did we rock your world or what?”  I was still in ecstasy and didn’t know what to say.  I just got a big shit eating grin on my face and said, “Now unlock these hand cuffs and let’s try that again with my hands free.”  They looked at each other smiled and unlocked the hand cuffs.  (To be continued)

Lady In The House - Part III

PantyhosePrincess on Transgender Stories

Lady in the House Part III


Michele Nylons


From Part II


Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crotch was soaked with hot sticky liquid and as I struggled to breathe I could smell the salty, slightly swampy smell that is associated with fresh semen.

Eddie had ejaculated against me. He slowed down his thrusts and slightly eased his grip on me. His spend had now invaded the layers of my panty and pantyhose and I could feel it wa

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rm and milky against my penis.

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."


Part III


Carmel appeared as if from nowhere and took me by the hand. I was so shocked at what had happened that I just followed her instinctively, as I passed Eddie, clattering on my high heels, he reached out and spanked my arse.

"Have her ready in half an hour Carmel, I haven't finished with her tonight; not by a long shot."

"Oh, and tell Steve he can use for ten but he's not to fuck her, ok." Eddie bellowed down the corridor.

"Of course Eddie, you want the secretary thing again or you want her ready for bed?" Carmel asked.

"I think I'll have her fully dressed again; stockings this time though, I don't want to have to rip any more pantyhose to get what I want ok!" Eddie answered.

"Sure honey, I know what you like, she'll be ready for you in half an hour."

"And don't forget to tell Steve he can't fuck her, I don’t want slops."

"Of course Eddie," Carmel smiled sweetly at Eddie, "Now come along Michele lets get you cleaned up honey," Carmel whispered dragging me down the corridor towards the bathroom on E Block.

"What's he on about?" I asked Carmel as we went into the bathroom and she led me to the sinks.

"Eddie is going to use you until you bore him, then you are going to be just one of us girls; a common prostitute hawking your pretty arse for Eddie; making him money and occasionally making him come." She sneered at me.

"Just get used to it; learn to like it!"

"Learn to like it!" I scoffed.

"Learn to like being dressed as woman and used by these poofters in this jail; you're fucking joking! I hurled at her.

Then I felt an enormous slap across my backside; the pain was excruciating.

"Oh god!" I moaned.

"No not god, just little old iron-bar Steve. Fucking hurts don't it; my steel bar crashing against your arse like that?"

"So you think I'm a 'poofter'; well I've got a another steel bar right here in my jeans honey and you've got about ten minutes to take care of it!"

It was Eddie's enforcer Steve, undoubtably he had heard Eddie say he could use me briefly and was wasting no time coming to claim his prize. I realised at once that fighting him would be futile and decided to let him take what he wanted. I had heard Eddie say he couldn't fuck me so I figured the best defence was attack. If I excited him enough maybe I could get him to orgasm against me just like Eddie had done. That was humiliating enough but I didn't want to consider any alternative.

I turned around and forced myself to move towards Steve and embrace him. I rubbed one nyloned thigh against his leg and reached up and kissed him. His breath was atrocious, I forced myself not to gag and pushed my tongue into his mouth and gave him a long kiss.

"Steve honey, you don't have to use that bar on me; lets just take care of the bar I can feel throbbing in the front of your jeans," I whimpered in what I hoped was a sexy parody of a seductive female.

"Oh but you don't understand Michele," he sneered, "its more fun to take what I want!"

Steve pulled me roughly to him and locked his lips on mine. At the same time his hand went to my skirt and yanked it up around my waist. He twisted his hands in the nylon of my slip and yanked it down around my knees and ground his body against mine. I felt his hard member pushing against me though the rough denim of his jeans.

Then Steve pushed me away to arm's length.

"Drop the skirt bitch'" he hissed.

"What?" I answered not understanding quite what was going on.


My head exploded with the force of the slap to my face; I thought my head had been knocked off.

"Don't you fucking mark her!" Carmel warned Steve.

"Well you tell that bitch, I ain't half as nice as Eddie so she better just take what's coming ok," Steve hissed at Carmel.

"Ok Steve, I think she gets it!" Carmel retorted.

"Well let's just make sure," Steve answered and then punched me in the stomach. I doubled over in pain completely winded.

"Right I'm wasting time, no more talk; just action. I tell you what to do and you do it bitch ok?"

I nodded as best I could, my face was on fire from the slap and I still couldn't breath.

"Skirt!" Steve demanded.

I put my hands to the waistband of my skirt and tugged it down around my ankles then stepped out of it along with my slip.

"Now my jeans!"

I stepped forward and tugged at Steve's belt.

"On you your fucking knees you stupid cunt!" Steve bellowed and brutally pushed me down.

Now my face was level with Steve's crotch and I reached out and undid his belt. I noticed again my manicured painted nails as I eased the zip of his fly down and snapped the button at the top of his jeans. As I eased the jeans down his legs a fetid aroma assaulted my nose and I noticed his putrid underwear.

"Stand!" Steve ordered.

I stood, tottering on my heels trying to recover my breath. Steve grabbed me and forced himself against me pushing his tongue deep into my mouth and pushing his hips against me. Carmel looked on at Michele; this attractive petite woman in heavy ruined makeup, dressed in her blouse and jacket but without her skirt, wearing torn and laddered hose and panties was teetering on her stylish black pumps as this jailhouse hooligan with fetid breath and stained boxers ravaged her.

I felt Steve reach between up and knew what he was up to. He was freeing his penis from his underwear as Eddie had done. I was still determined to get this over with as soon as possible and seized the initiative. As soon as I felt Steve's erect member against me I reached down and gently held it. I had never held another man's penis before and it felt tactile and spongy, I could feel the thick veins running along it. It also felt slick and warm. I commenced a slow stroking motion, easing my hand along the shaft and circling the enormous head. The cock was so thick that I couldn't grip its full girth in my hand.

Steve groaned, "Oh yeah bitch, you know what daddy likes."

He pushed me back slightly so he could see my painted nails trailing along his shaft as I wanked him. A thin thread of shimmering clear pre-come ran from the purple head of his penis across to my gauzy nyloned thigh. Steve reached out and rubbed my pantyhose thighs and then worked his way up to my panties. I stiffened as I felt his hand go inside my panties and begin to fumble about. I forced myself to relax otherwise I knew Steve would belt me again. Steve eventually found my thin soft cock nestled in the crotch of the sheer nylon panties and he began to free it from its little nylon prison.

I concentrated on slowly masturbating him to the best of my first-time ability. I gripped his member tightly and slowly squeezing and stroking as I worked my hand up and down his penis. He must be enjoying it I though, because he was just staring at my hand wanking him while one of his hands stroked my nyloned thighs and pantied crotch. As his other hand had finally freed my member, he began to squeeze it harder and harder. I just concentrated on getting this over with as soon as possible, the feel of his hand on my penis was vile.

I decided to move things along and pushed myself against him stroking his cock with firmer faster strokes. I lifted my head and kissed him, gently sliding my tongue along his gums and exploring his mouth, blocking out the awful taste of his breath. I guided his member against my pantyhosed thigh and rubbed it there, the underside of his cock with all those nerve endings rasping against the diaphanous nylon as my painted fingernails gently raked the top of his turgid cock.

I began to pump my leg up and down so that he was dry fucking me, similar to what Eddie had done. With my fingers stroking and squeezing in time with my humping leg I was hoping he would soon climax. He was groaning now and breathing heavy; his fetid breath puffing in my mouth. Combined with the meaty stench coming from his crotch I was ready to gag but kept control and tried harder to please him, kissing him deeper and stroking him harder.

Then he suddenly grabbed me by the shoulders and threw me back away from him. I stumbled back on my heels and my back crashed into one of the sinks, winding me again.

"Oh no you fucking bitch! You fucking cunt! I know what you're up to!" Steve roared.

"You're trying to get to come like this ain't you?"

"Well I ain't going to come in Eddie's leftovers. Get back here!"

I moved forward towards Steve warily. This parody of a secretary in a blonde wig, come-soaked and torn hose and panties, tottering on shiny black heels, dressed from the waist up in blouse and business jacket. What a sight!

Steve reached out and put his hands on my shoulders and pulled me to him. He kissed me deeply, forcing his tongue deep in my mouth. Then he eased his hands up to my shoulders and commenced to push me down.

'Oh God! I know what he wants,' I thought.

I dropped to my knees on the cold tiled bathroom floor and stared eye level at Steve's disgusting throbbing penis. He grabbed my head in both hands and pushed it forward so that the head of his cock was between my lipstick lips. He kept pushing but I couldn't open my mouth. The smell coming from his loins was fetid and I was sure that monstrous member would make me gag and vomit..

SLAP! I saw stars and the ringing in my ears blocked all other sounds. I started to cry and as I did Steve grabbed my head in both his hands and pushed his hard, throbbing cock into my mouth.

"You take this bitch, and don't bite or you're fucking dead!" Steve fumed.

He pushed the filthy thing into my mouth until he felt me start to gag and then commenced raping my face. That's the only way I can describe what he was doing to me. He held my head and raped it! He thrust his filthy, foul tasting, pulsing, penis in and out of my mouth. Besides the cheesy rancid taste there was also a sweet salty taste that I knew to be pre-come. My gag reflex was suppressed as long as he didn't drive his cock too deep into my throat, but it was so huge I couldn't breath.

Then I sensed Carmen beside me.

"Breath through you nose hun, breath your nose. He won't be long, I can tell he's nearly there."

Steve tightened his grip on my head and slammed me back and forth against his cock. He pulled me back until just my lips circled his plum coloured knob; then drove me against him as he thrust forward, forcing his turgid meat into my mouth. As a reflex I moved my tongue around the shaft and sensed his enjoyment. I was hoping he would come soon as every time his cockhead hit the back of my throat I had to gag. Then I realised the sick bastard was getting pleasure out of my gagging. Now he increased his attack on my virgin mouth and I tasted more and more of his pre-seminal fluid. He was groaning and panting.

"Yeah bitch, I'm coming whore, take this!"

He slammed forward hard and pushed my face into his groin and held it with two hands at the back of my head. His penis throbbed and erupted in my mouth and I felt the hot salty taste of his seed as it exploded from his glans. I started to gag and tried to force myself free as his semen flooded my mouth and slid down my throat.

"Take it bitch, take it!" Steve howled in his orgasm.

"OH Yeah baby, on your face yes! On your face!"

Steve pulled my face out his groin and held it close to his crotch with one hand; with the other he rubbed his still ejaculating penis all over my face. His ejaculate shot across my cheeks and landed on my eyelashes, a string of hot semen running across my face. Another spurt shot against my lips and up my nose. I felt stream after stream of semen scald my face and start to run down my neck. The thick gobbets of milky come smeared my cheeks, nose and lips. Looking out my eyes I could hardly see because of the ropes of hot come across my eyelids and lashes.

Steve's orgasm started to subside and he continued to rub his cock all over my face. He smeared his spend all over me, it combined with my lipstick and makeup to make a hot sticky film that covered my face. Steve stepped back and looked down at me, on my knees, may face covered in come, my clothes a mess and makeup mixed with semen, caking my face.

He reached out and grabbed a hand-full of my blonde hair and wiped his cock clean in it.

"Get this useless bitch cleaned up and dressed for Eddie; her night's only just started!" Steve sneered at Carmen as he turned his back and walked away zipping up his fly.


To be continued……………………………………………………………………………..

Amy's Surprise

showstoppa_4114 on Transgender Stories

“Amy’s Surprise”


by Matthew Ford


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an style="font-family: verdana">Amy Carlson was a beautiful girl who lived about 3 blocks from my house in a town with less than 2,000 people. She was home schooled until she was 19, when she transferred to the high school for her senior year.


Amy had brown, shoulder-length hair and beautiful green eyes. Her dad was a dentist so her teeth were blindingly white. She had evenly tanned skin, was about 5’6” and probably weighed around 120 lbs. She had a nice pair of boobs. They weren’t huge, only 36B, but they were round, firm, and perfect. Her legs were long and muscular, her stomach was firm, and her ass was amazing. It was round and well sized. Somehow, it was firm and soft at the same time. The year Amy went to the high school I was a junior. I had a few classes with her, but not as many as I would have liked. She only attended classes to get the credits she required to get into the private college she wanted to attend. I was the starting tight end and line backer on the varsity football team that year. Amy wanted to be a cheerleader, but she said she was just too busy. I could understand that, she went to school in the morning and worked as a waitress in the afternoon.


After the start of the 2nd quarter of school Amy’s sister, Karissa, got into a car accident with Amy’s car. Since she only had liability insurance, and was saving all her money for college tuition she couldn’t get a new car. Her parents had two other children to put through college after her so she didn’t ask them. Since her house was on the way to school I started giving her rides everyday. I would stop outside, honk, and she would be ready to go. One morning on the way to school, I asked her to go to homecoming with me. She said that she would love to, but she couldn’t. No matter how much I asked she wouldn’t tell me why. I just assumed it was because she wasn’t over her ex-boyfriend, who had gone on to college that year.


The year went on until football and basketball were over. It seemed like the year had gone by really fast. Amy and I spent virtually all of our free time together. At the beginning of April I asked Amy if she would go to Prom with me. She said no, again refusing to give me a reason. Two weeks later after school Amy came over to my house since she had the afternoon off and I didn’t have tennis practice on Fridays. We were watching “Zoolander” in my room when the doorbell rang. I went to go answer it. It was the FedEx guy. My dad had gotten a package. I left it on the counter for him and went back to my room. When I walked in Amy was on my computer checking her MySpace account. Amy looked at me, smiled, and said, “Matt, you wanna hang out next Saturday? I can get the day off.”


“Next Saturday is Prom ‘Ames’. I guess we could hang though, I don’t have a date for it anyway,” I answered.


Amy said, “Well, if we’re gonna be hanging out anyway, and Prom is going on, why don’t we just drop in and check it out?”


I was stunned. “You mean…wait, do you mean you wanna go to Prom with me? Or do you just wanna check it out?”


“Matt, will you go to Prom with me?” she asked smiling.


And just like that, I had finally succeeded in getting a date with Amy, or she had succeeded with me, either way I was happy. I had to line up a tux fast. I called my friend Brandon and he hooked me up. I was excited the whole next week. Everyday I saw Amy, and everyday she seemed to flirt a little more. Then, finally, Saturday came. I spent almost the whole day getting ready. I went to town to get a corsage and I stopped by the jeweler’s. At 7:30 that night, I grabbed the corsage, jewelry box, (and stuck a condom in my wallet, just in case) then got in my car and drove to Amy’s house. I went to knock on the door but Amy opened it before I could. She was standing there in a strapless dark purple dress that went to mid-thigh and pushed up her breasts, revealing a lot of cleavage. “Let’s get out of here before my parents know you’re here. They must’ve taken a million pictures of Karissa and Brian.”


We went to a nice restaurant for dinner. We talked and ate in our corner booth for almost an hour before I got the bill. Amy had been touching my leg all evening, but after the waiter went to get my change she laid her hand directly over my dick. She started rubbing and I knew it wouldn’t be long before it was hard. We adjusted our seating so we were even closer. Amy rubbed my crotch until I knew I was about to cum. I started to groan, and then she stopped, saying, “Not yet. Not here.” Then she got up as the waiter brought the change back. And said she had to go to the restroom but she would meet me in the car.


It was a little after 9:00 when we got to the school. We presented our tickets and went inside. Every time we danced Amy would rub up against me. My dick was throbbing by the time we went to take pictures. I let her choose the pose we would use. She decided we would do the dance pose. She laid back into my arms like I was dipping her. My dick pushing and rubbing against her ass. I knew she could feel it, and I also knew she loved torturing me like that.


When the last dance started playing at 11:55, the Prom King and Queen took their spots in the middle of the dance floor. It was my friend Brandon and his date Stephanie. We had already congratulated them and we decided to duck out then. There were several parties we could have went to, but we decided to go back to her house. Her parents had decided to get an early start on their anniversary vacation by getting a hotel room for the night before heading to the airport the next morning, so we would have the house to ourselves until Karissa got home. We both knew that Brian would not miss a party, so we had a while.


As we sat on her couch making out, I broke the kiss to give her the necklace I had bought her. She said she loved it, and that she had a surprise for me as well. She stood up and unzipped her dress, lowering it enough to reveal that she had a strapless purple bra on. She smiled at me as she unsnapped it and showed me her amazing boobs. The dress was still around her waist as she came back to the couch and sat on my lap. Amy looked me right in the eye and said, “Remember the day I asked you to Prom?” I nodded “And Remember how I wouldn’t go out with you or tell you why before that?” I nodded again. “Well, I’m going to show you why I wouldn’t go out with you until tonight. Last week, when you went to answer the doorbell, I got on your computer to check my MySpace, but before I did that, I wanted to see how far you’d gotten on your Economics report. I was going to check the report I swear, but I saw a folder that I had never opened before. I was curious, so I opened it. There was another folder inside, so I went into it. Then, I saw something that shocked me. I had found your porn. I figured you had some, most guys do, but I was surprised at the kind. Now, before we go any farther, I have to ask…do you like that shemale porn?”


I was mortified. I didn’t know what to say. I thought she was going to freak if I said yes. But then again, if that’s what had gotten her to go out with me, maybe I should tell her the truth. “um, well, I’m gonna be honest with you Amy. The idea of a hot girl, who also has…uh, a dick, does turn me on…so, yeah, I uh, I like shemale porn.” I was really embarrassed, I was waiting for her to get up and ask me to leave.


Just as I expected, Amy stood up…but instead of asking me to leave, she smiled at me. I looked back at her, confused. “Matt, I love the necklace…it was a great surprise.” As she pulled down her dress she went on, “and I told you that I have a surprise for you. And I think you’re gonna like it.” With this, her dress dropped to her ankles and she stepped out of it. She was wearing a purple thong, but what intrigued me most, was the bulge in it. “I have your surprise right here. But before you open it, I need to know that you want it. And you have to promise me that this surprise will be our secret. And you have to agree to always take good care of the surprise. Now, will this be a secret?” I nodded. “Will you take care of the surprise?” I nodded again. “And finally, do you want it?”


“Amy,” I replied, “I want your surprise more than anything.”


She stepped forward and said, “Then open it up.” With that, I slowly reached my hands out, and pulled down the purple thong until an 8 inch cock sprang at me. “Suck it, suck my cock,” Amy said softly, yet sternly. I needed no more coaxing. I opened my mouth and wrapped my lips around Amy’s cock head. I popped it from my mouth, then stuck it back in. I sucked on the head for a few seconds, then I stuck my tongue out and licked the bottom of her cock. I took it out of my mouth and licked the length of Amy’s surprise several times before taking it back into my mouth. This time I went deeper, sucking about 4 inches into my mouth and bobbing my head on that for a while. Amy looked into my eyes the whole time. “Deeper,” she whispered. So I began taking another couple inches of her cock. it was pushing into my throat now, my body wanted to gag, but I wouldn’t let it, I was loving sucking Amy’s cock too much to stop. She threw her head back and exhaled loudly. I began massaging her balls. They were shaven clean, just like the rest of her body. I squeezed them softly, and she moaned quietly. “Lick my balls,” she commanded. I didn’t want to stop sucking her cock, but I did as she said. I slowly jacked her cock while I licked her balls. My face was buried in her crotch. “Suck them,” she whispered. I took one into my mouth and sucked on it, then pulled my mouth away and it popped out, then I wrapped my lips around the other, repeating this several times. I was jacking her cock with one hand, fingering her ass with the other, and sucking her balls one at a time…I was really into it. Girls had done this to me before, and I had always wondered what it would be like to be on the other end. Now I knew, and I liked it. Amy grabbed my hair and pulled so that I knew to stand up. I didn’t really want to quit, but my mouth was pretty tired. She stood in front of me, looking into my eyes. She pushed me back onto the couch and dropped to her knees.


Amy undid my pants and pulled my 7 inch dick out. She immediately stuck it in her mouth. As she went up and down on my cock her left hand squeezed my balls. I was so hot, I knew I wouldn’t last much longer. She stopped her expert blowjob long enough to say, “Lemme know when you’re gonna cum.” Then she lunged her head forward, forcing my cock down her throat. She was taking it all, I couldn’t believe it. Amy went all the way down and all the way back up so quickly I knew she had done it many times before. Every time she would pull her head back far enough my dick would make a ‘pop’ as it was released by her lips.


“Ames, I’m, I’m gonna cum…” I struggled to speak because of the amazing feeling. When I said this Amy’s mouth went into double time. She sucked harder, bobbed faster, and her tongue seemed to be everywhere on my dick at once. I moaned as I came. Shooting a good 9 shots into her mouth, surprisingly she never stopped to swallow, it just all collected in her mouth as she continued to suck. She kept working on my dick until the pleasure was too much for me to take and I grabbed her head and pushed it away. All of my cum was still in her mouth. She opened wide to show me, then closed her mouth and swallowed it in a series of 3 gulps. She smiled at me with her snow white teeth.


Amy stood up and said, “I love cum. That’s one benefit of having a dick, I can have nice warm cum whenever I want. I want you to finish me now, but don’t swallow. Just keep it in your mouth and we can share it.”


I dropped to my knees and took her cock in my mouth as quickly as I could. I wanted to take all of it like she did to me, but her cock was about an inch longer than mine, plus I had never given head before. I was able to get almost 7 inches of it. I tried to duplicate the things that she had done to my cock on hers, I could make it ‘pop’ out of my mouth, but I couldn’t suck as fast or as hard as she could. As I worked on her cock, I started squeezing her ass. I began thrusting her cock down my throat by pulling her closer to me with my hands on her ass, basically forcing her to face fuck me. After a few minutes I was able to take almost all of her sweet cock down my throat. She warned my that she was going to cum, so I started massaging her balls. I moved my mouth out so that I only had the cock head in my mouth, then I took my left hand and started pumping her shaft while playing with her balls with my right. She threw back her head and groaned as cum started spraying into my mouth. Shot after shot of Amy's jizz filled my mouth. I swallowed some of it, I remembered what she told me, and I really wanted to share it with her, but there was so much of it I had to. I swallowed 2 gulps of it and my mouth was still full to capacity. I didn’t know cumming that much was possible. When Amy finally pulled her dick out of my mouth cum was running down my chin because I couldn’t keep it all in. it didn’t taste particularly good, but it wasn’t bad either. The feeling of having Amy’s hot jizz filling my mouth was incredible. She dropped to her knees and tipped my head forward and started kissing me, her tongue stealing her cum from my mouth. Her cum dripped out of our mouths and got all over her chest.


After kissing and swapping the cum back and fourth for about a minute, Amy started swallowing whatever went into her mouth. I started to swallow as well, trying to get as much from her as I could. We both drank it greedily until it was all gone. Then I pushed her back, licked up what was on her breasts, and swallowed desperately.


We made out for another 20 minutes until Amy got up and went to get something to drink. When she came back to the living room she had 2 bottles of Gatorade and a paper bag. She threw me the bag and a bottle. I took a drink, and peeked in the bag. I saw condoms, dildos, lubricant, and a couple CD’s.


Amy took a drink of her Gatorade and smiled brightly, “I hope you’re not too tired, it’s only 2:15. I’m not done yet, are you?”


I thought for a second, and replied, “Ames, I could go all night.”


Just then a car pulled into the driveway. It was Brian’s car. Karissa got out of the driver’s side and walked up to the door with Brian following closely behind. They came inside together and walked right by us and upstairs without a second glance. I looked to Amy after they were upstairs and she said, “Don’t worry, we’ll see them again before we go to sleep,” then she took another drink of her Gatorade and flashes me a beautiful smile. As I looked at her I thought to myself, "My girl has a bigger cock than I do. How many guys can say that?"

Lady In The House - Part II

PantyhosePrincess on Transgender Stories

Lady in the House – Part II


Michele Nylons

From Part I


Then the full light of the situation dawned on me. As I looked at the reflection of the trampy woman in the business suit I realised she looked just like a caricature of the ‘sexy secretaries’ I had seen posing in porn magazines just before they stripped off their clothes, page by page.

Now I knew why Eddie had called me his secretary! Oh my god! He had been planning this for weeks, having me help him pick out clothes, obviously getting his ‘girls’ to find out my size

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s for clothes and shoes. And now I had no choice but to be Eddie’s ‘sexy secretary’ or suffer an agonising beating and the loss of my limbs!

"Mike, now you are Michele, you look beautiful! I hope you enjoy your first time as much as I did," said Carmel as she slid past me and out the door.

And that is how I became to be dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail.


Part II


"She's all yours Eddie. She looks beautiful." I heard Carmel say as 'she' disappeared down the corridor, her high heels clicking on the tiled floor.

Eddie appeared at the door to the cell, he stepped inside and closed the door behind him.

"So what do you think of the little nest I have here for you 'secretary bird'," he asked sarcastically.

"Eddie, what's going on, what's all this about," I implored.

"Well if you haven't figured it out by now hun, you are a lot dumber than I thought. I needed a secretary, but not just to be my accountant, I need a 'Girl Friday' who can help run my business and take dictation; emphasis on the DICK," he smirked.

"I recognised your potential early, so now I have made you into Michele, my secretary, confidant, and soon to be my personal assistant. Very fucking personal if you know what I mean!"

Eddie stepped towards me. He was dressed in a pair of light tan linen pants, a smoking jacket, and expensive looking moccasin slippers adorned his feet.

"You look beautiful hun, just what I was hoping for; come here," he whispered hoarsely and reached out to pull me to him.

I immediately tried to step back out of his reach but he gripped my forearm and pulled me forward. As he did his other hand came up and slapped me soundly across the face. It was what the inmates referred to as a 'bitch slap', and it really stung. My eyes started to water.

Eddie took a handkerchief out of his pocket and put it to my teary eyes.

"Now Michele, don't cry; I would hate to ruin all the hard work that Carmel did with your makeup," he said.

"Just behave yourself and there will be no more pain."

He lifted my chin and looked deeply into my eyes.

"God your just fucking beautiful," he whispered and put his arms around me.

Eddie embraced me, locking his strong arms around me. His faced moved forward and I sensed he was about to kiss me. My involuntary action was to move back. His right hand came up again and was held out flat near my face, ready to slap me again. I forced myself to stay still.

He enclosed me in his arms again and this time his lips came down on mine. It was the strangest feeling, I could feel the slight rasp of afternoon shadow on his face, smell the faint scent of his aftershave and the press of his thick lips against mine. He pushed his tongue into my mouth and I could taste my lipstick mingled with his mouthwash. His tongue started to explore my mouth and he pulled me even closer.

I forced myself not to back away, rather I became limp. I knew there was no way out of my current predicament without extreme pain and punishment. Even then Eddie would take what he wanted from me. I tried to clear my head and just endure what was happening to me without further antagonising him.

Eddie was now kissing me passionately, his lips pressed hard against mine, his tongue exploring under mine then slowly working its way around my mouth, flicking and probing. His body was hard against me and I felt a hand slide down my back and come to rest on my buttock. He rubbed his hand there, the material of my dress and half-slip whispered against the smooth nylon of my panties and hose.

"Mmmm," Eddie whimpered, his lips still against mine.

He lifted his face and looked at me again. I realised he was not looking at another man, but a gorgeous woman in her mid thirties, her hair styled in a bottle – blonde bob and wearing thick makeup, rouged cheeks and plum red pouting lips.

"God I just have to have you hun, my lovely little secretary bird; this is just how I imagined it would be!"

Eddie started kissing me again and I felt his other hand slide down so that he had both of my buttocks in his grip. I felt him lift up the hem of my business suit skirt and caress the material of my half-slip. His hands worked in a circular motion in time with his tongue, rubbing the silky slip against my tight pantied buttocks. I was so shocked that it took me a while to realise that he was also gyrating his hips against mine; pulling my lower half against his as his passion intensified.

I commanded myself not to move, to just take what was coming; it couldn't be worse than a beating or broken legs!

Then I felt it, I went from being a limp rag doll and tensed up, almost pulling myself away. Using the utmost self-control I forced myself to go limp again in his arms and allow him to ply my body against his. What I felt was a long iron bar that could only be an erection pushing against my stomach. I could feel it though the material of his slacks and my skirt.

Eddie was gyrating against me now, his tongue working feverishly in my mouth, his lips crushing mine. The hands on my ass gripped my buttocks and pushed my lower body harder against him. He was 'dry humping' me I realised; pushing his erect member against me through our clothes. I heard and felt a deep humming from his throat and he was breathing heavily in and out of his nose as he continued to kiss me deeply.

Eddie suddenly stopped pushing on my buttocks and I felt a hand leave my ass, glide across my hip then move between us. He fumbled there, his hand between my navy blue skirt and his loose tan linen pants. My god I knew what he was doing! And then I felt the fruits of his efforts down there.

Eddie had freed his erect penis from the confines of his pants and it was now like a hard iron bar between us. His hand flew back to my ass and he again rucked up my skirt and used both hands to caress my buttocks through the slip as he pulled me back against him.

He ground himself against me, his cock hard against my lower abdomen. I could feel the girth of it though the layers of skirt, slip, panties and pantyhose. I concentrated harder on not panicking and just allowing Eddie to do as he wanted; surely this would be over soon.

Eddies kisses had now become a hard insistent invasion of my mouth; every few seconds he had to break to take a breath; I could feel my lipstick smeared over my lips and over my teeth. During these little gasps for breath he would pant,

"Yes! oh yes baby! so good! so good!!!"

"Gotta do it soon! gotta do it soon!!!"

Eddie again removed a hand and fumbled around down there between us. This time I felt him lift my skirt up completely so it was rucked up around my waist. He lifted me up and forced me to my toes, my heels left the ground and I fell further against him, my face now level with his as I balanced in the awkward high heels that I had never worn before. Eddie struggled with his erection and I felt him push it down then release it so it sprag forward whilst at the same time he pushed our lower extremities together.

His cock was now wedged between my legs, hard against my crotch and encased in the silky sheer material of my half-slip.

"Oh my god!" Eddie groaned and began his hard circular humping against me yet again.

He got into rhythm, dry fucking me in time to his feverish kisses; slowly circling his manhood he had trapped between us. Eddie tugged hard on my slip and I felt it start to drag down my thighs until it was around the tops of my knees. Now I could feel his turgid penis trapped between my pantied crotch and gossamer hosed thighs. Eddie was pushing up now as he thrusted, fucking the silken trap made by my pantyhosed thighs and nylon pantied crotch. I could feel the head of his penis rubbing itself along mine through my panties. My penis was still held in place tight between my legs by the gusset of my pantyhose.

Eddie had just what he wished for I guess. His slutty secretary forced to stand tiptoe in shiny black heels, her silken pantyhosed legs circled by her pretty peach half-slip just above her knees. Her dress rucked around her waist, her blonde bobbed hair framing a heavily made-up face that was locked to his in a powerful stream of kisses.

The big strong man held his sweet secretary in his tight embrace, sliding his tumescent member between her thighs, the gossamer of her hose and silken sheen of her panties serving to provide little electric shocks of pleasure through his body.

I felt Eddie quicken his pace and his cock begin to throb. He pushed against me harder and he held me so tight I though he would squeeze the breath out of me. His tongue was now a wild wet animal, thrashing in my mouth, fluttering and exploring every crevice.

Both his hands gripped my buttocks squeezing them roughly through the gauzy nylon panties and pushing me forward and back to the rhythm of his thrusts. Then he groaned and gripped my ass so tight that I felt the nylon panties tear and his fingers burst through and bury themselves into the gusset of my pantyhose. He forced me against him as hard as could and I felt his penis begin to pulse and throb.

Hot wet fluid suddenly soaked the tops of my thighs and the crotch of my panties. I felt stream after stream of his creamy seed shoot against my silken hosed thighs and being to slowly run down my legs. My crotch was soaked with hot sticky liquid and as I struggled to breathe I could smell the salty, slightly swampy smell that is associated with fresh semen.

Eddie had ejaculated against me. He slowed down his thrusts and slightly eased his grip on me. His spend had now invaded the layers of panty and hose and I could feel it warm and milky against my penis.

Eddie's hands slid up my body to my shoulders and he gently eased me back and lowered me to my feet. He looked down, pulled up my half-slip and smoothed down my dark blue skirt, the hem coming to rest against my sticky thighs. Then he did something that summarised in my mind how used I felt; he took a handful of my skirt and wiped his slowly deflating penis on it; the globs of semen and silvery seminal fluid staining the dark material as he cleaned himself on me.

"Not bad Michele," he chuckled, "Now clean yourself up sweetheart, you look a complete fucking Mess."



To be continued………………………………..



The Boy is A Girl Now

lmsyd4u on Transgender Stories

When I turned 16, I decided to go to a gay bar to see what the deal was.  I had not been with anyone ever but I was curious and very much feminine.  I stole my older brothers ID and caught the Bus to go to the Ballgame, so I told my mom.  Then I wound up at the gay bar just as they opened that night at 6:00 pm.  Todd and I look alike except that he is 18.  We both have long curly blonde hair, blue eyes and are almost 5’7” we weigh the same 155 pounds. 

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The only differences are that he has a six inch cock and mine is half that, and he has a girlfriend and I have always wanted to be one, a girl that is.

Well the bouncer at the door searched my ID for flaws then allowed me to pass.  As I walked by he whistled at me and I blushed and turned and said, “Thank you.”

He chimed back with, “No thank you for the view of your butt.”

I had on a silk shirt buttoned half way up; it was hot pink and with white slacks and shoes made me look good.  I had my nails filed and on the way there I coated them with clear polish. 

As I walked in several others followed behind me, there were a few guys already mingling so I strolled up the bar and ordered a margarita.  I had drunk one a couple of times when my mom would make them and leave the rest in the blender.  I was sipping on it when I noticed two hunks that were coming near me.  I acted coy and shy and it paid off big time.  The two of them were interested and as my cock showed, so was I, though I acted different.  They seduced me into the back booth for another round of drinks and we talked about things in general while I gulped the second one down.

Ivan was 6’2” light sand for hair that was tailored and short.  His blue eyes look like the sky and his dark tan was hot.  Hugh the guy by him was equally as attractive and they were almost the same except for his dark curly black hair.  They asked me how old and I lied, and said 19.  Then as we talked I found out that Hugh was 29 and Ivan was 25.  They were funny and sort of witty with me through the third round of drinks, but when the fourth round came they had the bartender use Vodka and I started to feel the effects right away.  Suddenly I started telling them, “I came here tonight to get myself screwed and to see if I can suck a cock like I have dreamed about for years.”

“What does it take to get your horny Billy?” Ivan asked as he petted my hand and slowly rubbed up my right arm.

“Oh that’s easy to do, but if you caress my nipples and suck them you can get into my pants and anything else as well,” I honestly replied wishing I hadn’t later.

“Sounds like you wish you were a girl then Billy.  Maybe we should rape you like a girl?  Come on what do you say to letting us take you right here and now?”  Hugh said as he slid his finger to my lower buttons and undone them.

As Ivan helped soon my shirt was opened and each man had a finger inside it caressing my nipples, and between the coos and ayahs, I replied, “Oh hell why not.”

Just about that time a couple of other men came over that were friends with them.  They were hard to make out as the drinks made my vision fuzzy, but one was big black and handsome and the other was a smaller red headed man.  Hugh had my shirt in the booth as Ivan began to undo and remove my pant sand sexy little silky white thong briefs.  I felt my cock exposed to the cool air and warm hands of Ivan just as Hugh leaned over and kissed me on the mouth.  I turned towards him a bit and off went my pants underwear and shoes.  His hands were playing with nipples as I felt my body float up and onto the table.  These men had done this before and in the bar, even though it was against the law.  The owner seemed to know that if he stopped them it would only make things worse so he let us go.

Hugh helped himself to my ass and began to lick and rim my asshole out, Ivan moved to drop his pants then kiss me before he offered his cock to my wanting mouth.  I looked at it for a few seconds before Hugh plunged inside me.  Then as I got use to the cock in my ass I licked Ivan and started to suck him slowly.  A few other people in the bar began to gather around and watch us as the bouncer stopped letting anyone else inside and told them the bar was full.  I was on my side naked as these two experts took full advantage of my horny virgin body.  When I felt Hugh pulsing to his orgasmic climax, I got so hot that I sucked Ivan like a vacuum and boy did he explode.

My night was far from over as the two of them relaxed the other two men took over and soon I had a new cock to suck and bigger dick in me.  The sounds that we were making were animalistic and raw and the feeling of his cock in my mouth aroused me to suck him off and swallow as much as I could.  The black man drove in my ass and made squirm from it a few times until he launched his load in me.

Suddenly I realized that I was being a slut and I looked up to see more blurry images of people and hear another set ask to take me as Ivan began to caress my nipples.  Men fucked my mouth and ass and as the night grew on I was fast becoming a male whore, and loving it.

One cock came to my lips it was bent rough and huge and as I took it in my mouth I was sucking the cum in from my lips of another one and there in the midst of this were my very well hung next door neighbor and his lesbian wife.  They slid up to me and started to enjoy me as well and before I knew it the man had me suck his cock off and then fucked me before the night ended.  At just after three in the morning they closed the bar and tossed me out the back door naked into the alley and no clothes.  I was so drunk that I couldn’t care and after passing out I have no really ideal of what happened to me the rest of the night.  Sometime early the next morning I awoke to find myself in a bed.  The room was dark and cold and the only light came from a screen at the base of the door.  I stumbled from the bed to find the floor bare cold concrete and then I saw a small handle on the door and turned the knob but it was locked.  I fumbled around until passing out again.  The next time I awoke the room was much plainer and I could see it was a cell.  I had been arrested by the police for public drunkenness and taken to the intake center.  They had kept me several hours before I realized what had happened to me and when they released me to my angry and upset mom, I wished they just had kept me in jail.  They had me in the adult prison and were just as mad at mom when they found out I was a minor.  She took me home and kept me inside until I was clearly berated beyond all words. 

I was grounded and told to stay home for eight weeks.  Then came my appearance and parole and was made to be home bound for another six months.  Since I refused to admit being in the bar they couldn’t fine them or anything for what happened to me and they couldn’t get anyone who said they had seen me there either.

Then after a few weeks more, my mom finally allowed me some freedom, two weeks before I turned 17.  I got me a part time job and saved all the money I could because while all this happened to me, all I really wanted was for it to happen every night.  I knew my mom understood I was gay, but she didn’t realize I wanted to become a woman.  My brother who began to understand me and accept me also used me during my home bound time.  I let him fuck me every night.  Pretty soon he like my ass better than his girlfriends and started finding ways to take advantage of me being home.  Including having me naked and tied over the exercise machine while he fucked me.  I made him shave my legs and arms and cock bald and then he started getting me the pills I needed to transform.  That’s why I got the job to save money to pay for it.

When my brother found out that I was going to do it, he helped me pay for it.  Then finally I found out how much I needed it one night when he was gone on a date with a girl.  I was just out of my bondage and the neighbor saw me and invited me over.  His wife was there with a camera and showed me some images she had saved on it.  It was me being fucked like a dog by her husband and some other men.  It made me so horny that I stripped naked and begged for him to fuck me and her to shoot it.  They made a copy of the pictures and put it on a disc and I used them to get dates on the net with.  Pretty soon I came to realize I could get money from men for sex, so I sold my body for $25 a fuck or $50 for a gang bang.  I made enough money by my 18th birthday to pay the whole thing and make enough contacts to enjoy it afterwards.

Today I am know as Sylvia Dee, I am the same height but I now have a set of 36D boobs and a soft little slit where a cock use to be.  I have been fucking men so long now I don’t miss my dick.  But if I go without sex for more than a day I miss getting dicks.

Michele And The Predator - Part V

PantyhosePrincess on Transgender Stories



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n">Michele Nylons

The Predator walked over to one of the stalls and grabbed a handful of toilet paper from the dispenser and then strolled over to the ottoman.  He looked at the transvestite whore lying there, her lovely blonde bob and white nylon blouse were covered in the biker’s semen, her stockinged thighs spread wide crudely displaying her red nylon panties soaked in her own emission and that of the biker who had fucked her. With her leather mini bunched around her waist and her red high heels wide apart resting on the ottoman, she looked fucked and contented.  He handed her the bunched up toilet paper, “Clean yourself up,” he growled.

The Predator watched the transvestite as she sat up and adjusted her underwear; she stood up and moved over to the mirror and used the paper and some tap water to clean most of the semen off her hair and clothing; she went into one of stalls for a few minutes and then he heard a flush.  He was thinking to himself that he had very much underestimated this transvestite bitch; she had handled all of the circumstances that he had put her in to and was gaining the upper hand with each situation. A plan formulated in the back of his mind.  Would she go for it?  There was only one way to find out.

The Predator held his hand out to the dishevelled woman and when she took it he led her back to the ottoman and indicated for her to sit.  She sat down and he sat beside her and looked at her face; still pretty despite the messy makeup and unkempt hair.  He slid a hand over her stockinged thigh and looked her in the eyes, “Michele is it?  Well Michele, we are leaving here now and I’m taking you home. On the way we are going to have a chat and I’m going to make you an offer that I want you to consider; either way, given what has happened tonight I don’t think you want to go the authorities and tell them what happened; otherwise your friends and family would have to know about your double life.  Just think my proposition over let me know one way or the other.” 

The Predator kissed her gently on the lips and helped her to her feet; he handed her her purse and took her by the arm and escorted her out of the ladies room into the dark bar.  He walked Michele past the booth where Red still sat nursing a drink, “Bye Red,” he muttered as they walked past.  As they made their way to the door of the bar the bikers standing around the pool table all applauded and yelled out cat calls.  The Predator led her out into the cool night air and over to his car; he opened the door for her and as she went to get in the car he pulled her to him and kissed her.  She responded and wrapped her arms around him holding him tight.  He gently disengaged himself and helped her into the car and they drove away into the night.

Three weeks later……………………………..

The Predator looked at the middle aged woman spread eagled on the huge four poster bed.  She was tied hand and foot to the bed by the stockings he had taken from her dresser.  She was just to his taste; her heavily made up face was framed by her permed red hair.  He studied her for a minute.  Her pale skin was sprinkled with freckles just visible under the layers of foundation, face powder and rouge.  Her eyes were pale blue framed by her dark mascara and eyeliner and her bright red lipsticked lips quivered in fear.

The Predator cast his eyes along her body.  She wore a red satin evening gown; now slit open from her breasts to the hem at the bottom of the dress.  The gown had been pulled open exposing the black nylon full slip that she wore underneath; this garment too had been slit from top to hem exposing her red satin half-cup brassiere and matching directoire knickers.  Just above the waistband of her knickers the lace top of a black suspender belt was visible; the garter straps peeking out from the legs of her knickers were attached to high sheen taupe stockings; the stocking tops were dark brown and pulled taught where the suspenders were attached by their glistening silver clips.  Her shoes were red suede high heeled pumps.

The Predator thought she looked like a sacrifice on an alter; the bizarre image was like some gothic tale; with her red satin gown and black full slip spread open beside her; he imagined she looked like a vampire queen, spread eagled and awaiting the stake.

The Predator moved over to the side of the bed and gently, light as a feather, ran the point of the silver steel blade of his knife along her body; starting from between her breasts, along the curve of her belly and down to her sex.  As she moaned he savoured her fear.  The Predator placed his other hand over the crotch of her satin directoire knickers and pushed the silky material into her cleft, “Like I said, honey; don’t cry out and no one gets hurt,” he whispered.

Michele was dressed in a full-body black leather corset; her new breastforms filled the cups so that the leather pulled taught across her breasts.  She wore black satin full cut panties, the crotch just visible below the bottom of the corset.  Suspender straps ran from the corset underneath her panties and were attached to diaphanous black nylons with dark reinforced cuban heels and stocking-tops; tiny diamantes decorated the satiny stocking-tops and the cuban heels; a black seam ran up the back of the stockings.   These were the same stockings the Predator had made her wear to the biker bar three weeks ago; she knew he loved them.  Her feet were shod in black patent leather high heeled sandals; her painted red toenails just visible through the reinforced toes of her nylons.

Michele had carefully matched her makeup to her attire; which reflected her mood this evening.  Earlier in the evening she had sat in front of her makeup mirror and contemplated how she wanted to look.    The theme was dark; black actually, and she was so excited that she had to be extra careful when applying her makeup.  She applied two thick but even coats of pale foundation to her face and neck.  Then she painted jet black kohl to her upper and lower eyelids, starting in the very corner of her each eye, working outwards applying three thick coats so that her eyes looked like an Egyptian goddess.  She carefully brushed dark purple eyeshadow onto her eyelids applying several coats to get the desired effect; she smudged the dark makeup with a finger feathering it out and up so that it faded just below her eyebrows and extended right to the outer edges of her eyes.

Michele next applied a dusting of red rouge to her cheeks; running it diagonally across her cheek-line and feathering it up to almost meet with her eyeshadow.  She applied a coat of pale face powder next, setting the foundation and rouge.  Then she carefully removed the plump black false eyelashes from their little plastic container. She fiddled around until they were set perfectly and indistinguishable from her own upper eyelashes.  Her lashes were now long, plump and dark.  She heavily mascared her lower eyelashes and then reached for her lipstick.  She applied blood red lipstick to her lips using the base coat applicator and then set her lipstick with the clear top coat.  As she did this she was pleased to see her bright red nail polish matched the lipstick perfectly.

Michele applied another coat of pale face powder and reached for the wig she had selected earlier.  The wig was a jet-black short bob; she adjusted it in place and fiddled with the fringe so that it was in a perfectly straight line across her forehead coming down to just over her eyebrows.  She gave it a final combing; the sides of her hair extended along her cheeks and angled up; the hair at the back of the wig ran high across the back of her neck displaying her delicate white skin.  To emphasise her neck she clipped on a diamante set silver necklace which had three strings of diamantes drops connected to the main necklace hanging down to the top of her breasts.  She clipped on matching earrings which dropped almost to her shoulders.

Michele wore a huge red ruby ring set in silver on the ring finger of her right hand and a huge yellow diamond with matching setting on her left.  On all of her other fingers she wore silver rings of various designs.  Around her slim, black-nylon clad ankles she wore silver anklets.  She stood up and slinked over to her full-length mirror and looked at herself, her eyes wondering up and down, adjusting little things here and there. She uttered one word; “Perfect.”  Then she sprayed herself liberally with her favourite perfume, ‘Poison’, pulled on a trench coat and went down stairs to wait for the Predator who would soon be here to take her out on her first adventure with him.

Michele now stood on the other side of the huge four poster bed and looked down at her captive.  He was tied to the bed in the same fashion as his wife; lashed to the frame of the bed by nylon stockings.  He was wearing a black dinner suit but the jacket had been discarded before the man was restrained on the bed.  His crisp white formal shirt was unbuttoned; the tails untucked from his trousers and the shirt wide open displaying his dark hairy chest.  His black dress trousers had been pulled down to his ankles so that only his white satin boxer shorts covered his manhood.  He was about fifty but still trim and handsome; his deep blue eyes were set off by his black curly hair.  His face was chiselled and his cheeks well defined.

Michele ran a sharp red fingernail down his body, starting at his throat and ending just below his belly button where the waistband of his boxer shorts lay tight across his abdomen.  The man groaned; “You won’t get away with this you bitch!” Michele responded by gently fondling his package through the satin shorts and whispering, “Shush honey; you heard what my partner said; don’t cry out and no one gets hurt!”  She was pleased to feel the man was adequately endowed and could hardly wait for the fun to begin.  Her own genitals ware restrained by a gaff and as her excitement mounted it was becoming decidedly uncomfortable.

The Predator was naked; his rampant penis stuck out in front of him, tumescent, pink and swollen, a long rope of clear pre-seminal fluid hung from the eye of his glans.  He climbed onto the bed and straddled the woman who was lashed there spread eagled.  He rubbed his cock over her satin encased tits and groaned as the silky material stimulated the nerves in his hard member.  The woman squirmed beneath him but all her movements did was to excite him further.  He grasped the bed head and lifted himself up and forward until his cock was over the woman’s face and then lowered his crotch until his erect penis rested on her cheek.  He rubbed his cock all over her face and was delighted when a single tear escaped her eye and ran down her cheek.

Michele watched the Predator climb on the bed and knew that the fun was about to start.  She saw the look of anger in the eyes of the woman’s husband.  She sat on the bed beside the man and lowered her face to his and pressed her mouth down on his thick sensuous lips.  He tried to move his head away and she gripped his testicles through his shorts and squeezed.  He got the message and lay still; he knew there was nothing he could do.  The Predator had done all the talking when they had overpowered the couple as they had just finished dressing to go out for the evening.  The threats the Predator had made, particularly against the woman, had forced the couple to capitulate.  They knew their best option was to be compliant and then hope that the man and woman who had broken into their house would leave them unharmed once they had had their way with them.

Michele probed her tongue inside the man’s lips and forced it into his mouth; she swirled it around and savoured his sweet fresh breath.  She eased her grip on his testes and snaked her hand inside his shorts and took his thick flaccid member in her hand.  She kissed him harder and slowly started to stroke his penis.  She heard him gasp and then she felt his cock begin to harden in her fingers.  Michele smiled even as she continued to kiss him; she thought to herself that men were just so easy to control.

The Predator looked across at Michele kissing the helpless man on the bed and smiled when he saw her hand disappear inside his shorts.  He sniggered when he saw that she was goading an erection out of the man.  He moved his body down onto the woman so that he was lying on top of her, his face hovering over hers, “Look,” he said, “your husband can’t help himself; he’s enjoying it!”  The woman strained and turned her head and saw the attractive black clad woman kissing her husband; she looked down and was horrified to see the bitch had her hand inside her husband’s shorts and was stroking him.  She was more horrified when she saw the woman ease her husband’s erect member out of the fly of his shorts and stroke his hard cock, her bright red fingernails snaking up and down his tumescent member.

Michele was now stroking the hard cock in her left hand; she slid her fingers up and down the spongy mass of sinew and veins and felt it thicken and engorge.  She kissed the man passionately and he groaned and started to respond to her kisses, the tip of his tongue exploring hers.  Michele pressed her body against his and slid one sleek nyloned leg over his and began to rub her black nyloned leg up and down; he writhed and began to push up with his abdomen so that his cock was actually fucking her hands.  She loosened her fingers so that his cock was held in a feather like grasp; barely touching the skin of his penis.  She felt him buck and bounce as he tried to get more friction on his manhood.  Michele’s smile widened.

The Predator watched as the woman looked on horrified at the reaction of her husband to the ministrations of the whore who was rubbing her stockinged thigh along her husband’s leg.  She saw him attempting to fuck the trollop’s hand and heard his heavy breathing in between the long wet kisses.  More tears escaped her.  The Predator lowered his face to the woman and began to spray soft kisses on her pale skin; he gently lapped up her tears with his lips.  He ran his hand down her belly and tenderly cupped her sex through her directoire knickers and began to work the soft gossamer material of the knickers into her cleft.  The woman stiffened beneath him and then began to struggle. He forced his lips down on hers and pushed a finger into the folds of her labia and began to softly stroke her clitoris.

Michele looked across at the Predator as he began to stimulate the woman’s sex and force his mouth over hers.  She lifted her face away from the woman’s husband and whispered in his ear, “Look.”  The man turned his head to the side and was greeted by the sight of his wife struggling under the monster who had invaded their house.  To his disgust he saw his wife stop struggling and begin to move her hips in a circular motion in time with the man’s hand which was buried in his wife’s knickers.  While his attention was elsewhere Michele turned around on the bed and lowered her face the husband’s erect shaft and slurped the stiff member into her mouth, smoothing her lips all the way along the shaft until her lips were at the base of his cock; she lashed her tongue around the bulbous glans.  The man moaned and pushed his hips up off the bed and began to fuck her mouth as she moved up and down on his rampant cock.

The Predator looked across at Michele and saw her fellating the woman’s husband.  The man was face fucking Michele and he had look of extreme pleasure on his face.  The woman beneath him was now squirming and bucking as he manipulated her clitty through her knickers; he took his hand away and heard her mumble her disappointment into his mouth as he kissed her.  He didn’t disappoint her for long; he adjusted his position on top of her so that his hard cock was buried in the fissure of her open labia and began to dry fuck her through her satin knickers.  She bucked up against him and he moaned at the intense sensations shooting through his cock caused by the sleek material of her knickers rubbing against his erection.

Michele was sucking the husband’s cock in a steady rhythm, grasping the sinewy cock between her lips and whisking her tongue along and over his glans.  She could taste his secretions and his humping motion lifted his arse clear of the bed as he bucked under her.  She glanced across to see the Predator slide his cock between the wife’s legs and knew that soon this little drama would come to its climax.  Michele eased her face away for the man and this time she actually heard him grumble in disapproval.  She eased a hand inside her panties and untied the gaff so that her aching member could be free and then she lifted herself up over the man so that her stockinged thighs straddled his.  Michele raised her arse up and eased the gusset of her black nylon panties to one side and lowered herself slowly so that the tip of the man’s cock nestled up against her sphincter.  Michele lowered herself and gasped at exactly the same time as the man when his thick bulbous glans slid inside her.

The Predator saw Michele mount the husband and position his cock underneath her; he pushed the woman’s face to the right so she could see what her husband was doing.  The woman gasped, and as she did the Predator quickly repositioned his cock under leg of the woman’s directoire knickers and pushed his hard cock into her tight slick cunt.  The woman bucked and rolled beneath him and he hung on to her and enjoyed the ride.  He didn’t know if she was trying to buck him off or was trying to fuck him and he didn’t care; her firm vaginal walls were stretched around his rampant penis and all he could feel was the intense pleasure shooting out from his groin.  The woman beneath him began to set a measured tempo with her thrusts and it was obvious now that she was enjoying what she was getting; forced or not.  The Predator adjusted his position so that the base of his cock pushed against the woman’s clitoris and his balls rubbed against her gossamer smooth directoire knickers.  He started to fuck her hard and fast feeling his orgasm building.

Michele eased herself down further so that the man’s cock slid slowly further inside her.  She had lubricated her back passage in the bathroom before she had joined the Predator at the bedside and now she was glad she had.  The cock filled her anus and she had to take it easy and ride with the man beneath her to stop him lunging up and stabbing her arse with his cock.  She took control and eventually she was filled up with hot throbbing cock.  She sat down hard on the man to stop him from fucking her; she just sat there and enjoyed the feel of hot cock filling her arse.  Michele stated to gyrate as she clenched and unclenched her internal muscles to stimulate the cock buried inside her.  Then she started to slowly ease herself up and down on the rampant member, eventually loosening up enough so that she could increase the tempo.  The man beneath her sensed this and matched her with his thrusts; as she lowered herself down, he thrust up; the head of his cock pressed against her postrate and she felt her own orgasm build.  Michele bucked faster up and down on the cock and felt it slide in and out of her and stimulate the hundreds of nerves along the walls of her arse.  She was close to coming.

The Predator fucked the housewife with long hard strokes and lowered his face to hers and was greeted by sloppy wet kisses as the woman bucked beneath him.  Her cunt was spasming around his cock and he sensed she was about to come; he thrust faster and harder and was rewarded with her hot juices flowing around his hard cock.  He crushed his lips against hers and plunged his tongue into her mouth; he ground his groin against hers and she pushed back hard against him and her cunt convulsed as she orgasmed.  The Predator’s cock spasmed and twitched as it shot load after load of hot semen deep into the woman.  The housewife pushed back against him and shuddered as her orgasm racked her; she gasped around his tongue but continued to mash her lips against his, there tongues intertwined and teeth crashing together so intense was their climax.

Michele pushed down hard on the cock buried deep in her arse and felt it convulse.  The man’s member shuddered deep inside her and as it spasmed she felt jets of hot fluid fill her back passage.  His knob was pushed hard against her postrate and she felt her release.  Her issue shot from her semi-hard cock and filled the front of her panties.  Michele slammed her arse up and down on the rock hard cock that was spewing semen deep inside her.  She screamed and moaned and shook her head; the sensation was so exquisite.  Eventually her climax subsided and she came to rest straddling the man who lay there moaning beneath her, his cock pulsing in the last throes of his orgasm.  Michele lowered her head and gave the man a sloppy wet kiss and then leaned back and looked across at the Predator.

The Predator looked across at Michele as she raised herself from the hot wet kiss that she was giving the husband.  He saw her straighten up, the man’s cock still buried in her arse as she straddled him.  She smiled at him and leaned across; the Predator lifted himself from the housewife and Michele and the Predator kissed each other passionately across the bodies of their victims who lay lashed to their marital bed; the Predators cock was becoming flaccid inside the woman, and Michele’s back passage was contracting around the wilting cock buried inside her.  The wife looked across at her husband and whispered, “We can never tell anyone about this,” Her husband responded, “Never.”

Michele and the Predator smiled at each other.

The End






































Lady In The House - Part VIII

PantyhosePrincess on Transgender Stories

Lady In The House – Part VIII


 Michele Nylons


"You!!!" Eddie screamed through the bars, then laughed.

 "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by the bulge of my slowly diminishing erection.

"Ok fun’s over; now get the fuck out of here while Mabel cleans the joint up for tomorrow night, I expect you will be a lot busier tomorrow Michele, once t

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he word gets around that my newest girl is available to all customers."

"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


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.