Thigh High Boots Stories

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Orientation
Length
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Infinite Scroll

From Stephen to Stephanie Pt. 04

by nikkiwest101 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter one The morning after the party I answered the phone, it was Emma who had tormented me so much the previous day, she asked to speak to Karen who then told me that Emma wanted her scarf back and wanted me to deliver it to her. Karen insisted that I go and change into my maids outfit, she surely didn't intend for me to walk to Emma's house dressed li...

Teaching My Boss a Lesson Ch. 02

by sexymistress6969 on Sep 16, 2017
Transsexuals & Crossdressers

(note this is the second chapter to a previous story) * Jess pulled the car into the parking lot of her apartment building, flipped it into park and turned the car off. She turned to look at the slut sitting next to her. "Alright slut, time to face the music. We are going upstairs but Mistress needs to make sure everything is in place for her slut." Jes...

The Transformation of Ms. K

by parkerkwon on Feb 25, 2019
Transgender & Crossdressers

By day I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish, as I became older I began buying some pieces of lat...

Mistress Natasha

by maidevie on Sep 26, 2017
BDSM

The soft black and chrome leather bustier pushed Natasha's breasts upward to astonishing heights; the mounds of soft flesh trembled with every step that she took. John sucked in a deep breath as she walked towards him. She was truly a Goddess. Her legs were on display in black thigh high vinyl boots, the heels of which had to be at least 6 inches high and de...

From Roommates to Lovers

by boca196461 on Sep 13, 2017
Transsexuals & Crossdressers

It was another quiet Friday night in our dormitory. The other two students who live in our student apartment had gone home for the weekend. It was just me and Brian...and I was never very close to Brian. He was quiet and tended to spend a lot of time alone in his room. I had gone out for a pizza and got as far as the elevator when I realized I had forgotten...

Tables Turned Ch. 05

by mw0212 on Aug 31, 2017
Fetish

Chapter 5 -- The Discovery Jack had spent the last few weeks busily organising a schedule & completing requisition forms in preparation for the installation of the new system. He had made the final presentation to Miss Sharp, who in turn had made her recommendations to the board & had been given the go ahead for the project. It was now up to Jack to make it...

DIY Was Never Like This!

by LucyCanyon on Sep 16, 2017
Transsexuals & Crossdressers

Two weeks ago, I helped out a friend of a friend one Saturday morning. I was amazed to find myself involved in some fantastic and mind-blowing sexual activities that rather got in the way of completing the work I was expected to do. At the end of the day Fen, the lady of the house, had found herself in submission to her stepdaughter, which was a complete rol...

Torturous Boots

by Fetish114 on Sep 17, 2017
Fetish

A story about perverted revenge Pete wasn't your average 19 year old boy. Unlike hanging out with guys and chasing girls Pete enjoyed dressing up in women's high heel boots and wearing sexy feminine leather. He was very much into the whole fetish S&M scene and enjoyed purvey nights at domination clubs and fetish balls. Pete lived with an old lady called S...

Breaks the Day Up Nicely

by NeilMc123 on Nov 4, 2019
Exhibitionist & Voyeur

I'd been out most of the morning, getting my pampering completed, Nails, Hair, Bikini and Body Waxing, and spent an outrageous amount of Jeff's money on some very salacious sexy underwear. Jeff does like the soft latex and faux leather look and he'll be pleased to know my latest purchases will not disappoint him. In my shopping bags were a very provocative q...

A Shemale Vacation Ch. 02

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we...