Story Details

Caught in my friends High Heels and Hose

Nylon Mistress on Transgender Stories

I couldnt believe the feeling as I slipped the pantyhose on over my legs. This was an absolute dream come true and I was living it right now.
My friend Julie had gone out for the night with her 15yo daughter and she'd given me the spare keys to her house. She'd had a tradesman doing some work and needed to leave before he'd finished, so she'd asked me to go around and lock up for her after he was done.

But as I went to turn the key in the lock something stopped me. Julie had always excited me and I'd lusted after her quite a bit. But even though she was 'available' since her husband was no longer around, I'd always got the feeling that sex wasn't something that she was all that interested in, with anyone. I dont think she realised just what a sexy woman she was and often I'd sit uncomfortably while talking to her as my erection grew. And she pandered to my favourite fetish without realising it too, and often wore pantyhose with her high heels. Just one glance was usually enough to keep me hard for ages and ages.

Well, I didnt turn the key, and I went inside. I crept inside feleing like a naughty boy, and trembling with anticipation I opened her bedside drawer. Inside were a number of pairs of her hose, and I couldnt resist. I had my pants off within a second and held the pantyhose up in front of me. I grabbed some black panties from the next drawer and struggled to pull them on. They were too small but they seemed to stretch a mile and  finally I had them on. My erection stuck way out of the top, there was no way the flimsy panties could contain it. Then I sat on her bed and pulled on the pantyhose. This was magic...feeling the hose slide over my leg, knowing that they'd also been on hers... Feeling the silkiness of them, and stretching them tight as I pulled them up and over my now dripping cock.

I opened the closet to search for some heels. There were a lot to choose from but I grabbed a set of shiny black patent strappy sandals that I'd always liked. I tried to put them on but they were way too small for me. Not to worry, I knew where they'd fit nicely. I picked one shoe up and then slipped my cock out of its nylon prison. The head was dripping with pre-cum and I slid the head through the straps of the shoes. It was almost a perfect fit and I felt my cock grow even harder. I slowly slid my cock back and forth inside the shoe and lie back on the bed imagining that I was jerking myself off over Julies nylon clad feet while she wearing the sexy heels. I'd intended to stop at the appropriate time but I got so carried away that I couldnt and I exploded all over the place. Huge jets of cum spurted out of my cock all over the shoe and dripped off onto the other one lying next to it. I dont think I'd ever come so much in my life and it almost soaked the shoe inner and slid slowly down the stilettos heels.

Oh it was wonderful...it wasnt so much the thought of her, but the combination of the hose and heels had really got me going. I'd always been someone that enjoyed a little dressing up, but the thrill of doing it in secret with someone elses stuff just took me over the top.
After the orgasm I couldnt resist lying back for a few minutes and enjoying the feeling. So..I got the shock of my life as I heard the key turn in the door and realised that I'd fallen asleep on the bed and was still 'dressed up' and the remnants of my pleasure were still dripping off Julie's heels.

'Oh God, what am I going to do?'

Too late, no time to do anything, and Julie turned right straight into her bedroom and stared open-mouthed at the sight that greeted her.

'My god, you're...but you're...What are you doing?'

'Oh I'm so sorry...Oh I dont know what to say....I just felt a little horny..and ..I... Oh god I'm sorry..'

To my amazement she recovered quite quickly and said 'OK, I dont understand this but just tell me what you were doing?'

I confessed my whole story, how I had a pantyhose and high heel fetish and I was just having a bif of fun and didnt mean for her to find out. It was just a bad set of circumstances and I was happy to do anything to make it up to her.

She laughed at me 'Allright, I cant say I understand that sort of fetish but it hasnt hurt anyone, just shocked me a bit. Maybe you best clean yourself up and...well I'm not sure I want those heels any more, you can take them too!' She laughed out loud this time as she lifted one of the shoes up and strings of sticky cum dripped off the heel.

'Hmm its been a long while since I've seen a sight like that...actually I'm not sure I ever have? Woah there, what's going on there?' and she pointed down at my cock which despite my embarassment was beginning to stir again and was now pointed directly at her.

'Oh no, I'm sorry..I'm so sorry, it's just that like most men I only have limited control over that part of me. I'll, I'll just cover up and get dressed and...'

Her hand went to my mouth and muffled the final words.

'Look it's ok. To be honest I've had a couple of drinks at the party and was feeling somewhat horny anyway and was about to give myself a bit of action. Maybe we can both end up happy from this?'

I couldnt believe what I was hearing and she leaned over and stroked my now rock hard cock and then pulled her dress off over her head. Now she stood there before me just in her bra and pantyhose and some cute red pumps.
'I couldnt be bothered wearing panties tonight'
She lowered her mouth over my cock and sucked it gently. The feeling was divine as she slid the entire length in and out of her soft mouth.

'Oh god I havent done this for about 6 years, I'd forgotten how good it was' she said as her tongue flicked away at the drips on the head of my cock.
'Listen, get out of that stuff, if you're going to dress up I want you to look like a bit more of a slut'

'Umm, ok...' although I wasnt sure what she meant.

She grabbed some black fishnets and a pair of red lace panties out of another drawer and asked me to put them on. The fishnets were crotchless so my cock and ass were bare to the world.

'Umm exactly what do you mean by slut?'

'Look if you like to wear girly stuff, I think I'd like to treat you like one' and she pulled a big vibrator out of the bottom drawer and dripped some lube onto it
'Get on all fours on the bed. Tonight you get to fuck me, but I get to fuck you too...'

I did as she asked and assumed the position. I felt her tongue slipping into my ass crack and was amazed at how good it felt. She ran her tongue up and down and every now and then slid it into my ass. It was a feeling like I had never had before and I was loving it.
'This should be fun' she said. And I felt the tip of the vibrator in my entrance. Then a slow steady pressure as she gradually slid it into my hole. I thought it would hurt but the feeling was great as she worked it in and out. I couldnt resist and kep pushing back toward her in time with her strokes. I was being ass-fucked and loving it.

'Ha ha..I didnt think you'd be into it so much my dear. Seems you're more of a sissy than you thought' and plunged the full length deep inside me. I shuddered as all 7 inches slipped in and shouted out

'Oh god fuck me, fuck me Julie' I yelled as she plunged it in and out of my asshole. Yes I was a sissy slut and enjoying it. She kept it up until I yelled that I was coming and then with a final plunge thrust it in a far as it could go, every inch of it straining my previously virgin hole.
As it bottomed out I screamed and jerked and my cock spasmed wave after wave of cum. I looked down between my legs and saw her lying there underneath me, her face directly underneath my twitching cock and my cum splashing off her cheeks and dripping down all over her. Her arm was twisted around still holding the vibrator inside my ass.
She smiled as she saw me looking at her, and licked some of the cum off her ace with her own tongue.

'Mmm that's the first load I've had in I dont know how long and I dont think I can ever get enough again'

'Now its my turn' she said. I need a bit of fun! And she lay on her back and pulled my face into her crotch. Even through the pantyhose the smell was overwhelming, she was really, really ready to go. I licked her all up and down and she squirmed and screamed in delight and pushed my face harder and harder into her, almost crushing me against her pubic bone.

'Oh god baby, that's it, keep going, eat me, eat me good'

I didnt need any encouragement and I was enjoying it as much as she was and I was happy to lick every ince of that wet pussy all night. I bit away at the pantyhose and finally created a hole and plunged my tongue deep inside of her. She arched her back and let out a little whimper of delight.

'Oh yes..thats it...more..more'

By now my dick had gotten hard again so I thought I'd give her what she really wanted. I turned her over and lifted her ass in the air. I slipped in between her legs and positioned my cock at her pussy entrance. I could hear her hold her breath as she waited for me to enter her. I looked down and I could feel her pantyhose rubbing against my own fishnets, it was an ultimate fantasy for me, fucking in hose and heels.

With a single thrust I was inside her and she let out a muffled cry of pleasure. I began to fuck her with long slow strokes. Using the entire length of my cock each time as I pleasured her. She cried with delight and pushed back against me with each thrust

'Yes, yes, fuck my cunt, fuck me, fuck me...Oh god I want it'

Hearing her talk like that made me even hornier and I upped my pace even more, banging my balls against her ass with each stroke as I entered her.

'Ohh I'm commminng......' and she made a final rearward thrust onto my cock and then collpased forward onto the bed.

I was close again too and pulled my cock out and stood at the foot of the bed. I gave my cock a final few strokes and then watched yet another stream of cum spurt forth all over Julies shoes and legs. Long streams of the sticky white goo ran up and down all over and dripped onto the carpet. She must have know what I was doing and flipped over onto her back, slid off her cum-soaked heels,  and took my cock between her feet to milk the last few drops of cum out. I almost buckled at the knees as I watched it drip out all over her toes. I just loved it.... And when there was none left she surprised me by lifting her feet to her mouth and licking the stickiness off them.

'Told you I hadnt had enough didnt I?' and smiled at me..

'Maybe we best keep this little effort our secret?'

I smiled in agreement and lie down beside her on the bed. I was about to drift off to sleep again when the key turned in the door again

'Oh my god, my daughters home, I forgot.....'

to be continued.....

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