Chastity Cross Dressing Stories

77,281 results
Orientation
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Infinite Scroll

Sex Talk with Kathie Lee and Hoda Ch. 01

by DickThePimp on Aug 20, 2018
Celebrities & Fan Fiction

This is a parody... It is not real This is a new series starring Kathie Lee Gifford and Hoda Kotb... It's about them spicing up their show with a new segment, Sex Talk... This segment's guest is Nina Hartley... Enjoy *** I was sitting in my girlfriend, Kathie Lee Gifford's dressing room, watching her show, rubbing my cock. She and her co host, Hoda Kotb,...

BluBalls for Kitty's BootBoy Ch. 02

by KittyZateez on Mar 21, 2018
Fetish

We now continue with the story of how I seduced and enslaved a nice gentleman with a weakness for women's sexy thigh-high spike-heeled boots...after the initial encounter I described, meeting him at the nightclub and beginning his seduction, over time he and I came to have a very close friendship, and we enjoyed many kinky, erotic encounters involving his fe...

Adding Risk to Swimming

by LstDghter1 on Sep 14, 2017
Exhibitionist & Voyeur

I have recently taken up swimming again, I used to swim for my County when I was younger and gave it up due to Uni and work using up too much time. Now that I have finished Uni I have started to go back again. I am 21 years old, very petite build, weighing around 50kg and barely 5 foot tall. I have shoulder blade length, brunette hair and blue eyes. I wear...

The Shopping Trip

by zbrewster on Sep 15, 2017
BDSM

The Idea Janette had been a little worried lately. Alan had been busy at work for the past few months and had not been paying her as much attention as she would have liked. She was beginning to feel a little insecure of her own femininity and was wondering if Alan might have a little something on the side. She herself had been busy at the lab recently and d...

Strip Tease Ch. 01

by ladyellen on Sep 12, 2017
Exhibitionist & Voyeur

I looked up surprised as Tom, my husband, swore and brushed the papers he was working on onto the floor. "There's no way I can work this out." He sat back in his chair holding his head in his hands. I went over and put my arms around his shoulders. "Surely it's not as bad as all that." He shook his head. "I'm afraid it's very bad and it's going to get wors...

Rachael

by Scotsman69 on Aug 23, 2017
BDSM

Author's note: This is a fantasy. Well, so far... My thanks to the young woman who inspired it. ***** The train was late. Sandy fidgeted nervously before the announcement board, impatient in his lust. He reached Platform 15 as the train sighed to a halt, searching faces. Then she was before him, breathless and trepidatious. Maybe scared. But that was as i...

The Path to Happiness Pt. 07

by brendachaplin2000 on Nov 18, 2019
Transgender & Crossdressers

Several days had passed since my encounter with David, I have since meet him for coffee as Brenda, and I can see us becoming good platonic friends. We are both clearly bottoms, and we made a date to check out a few of the gay clubs in London. I also had my second appointment at the gender clinic, the hormones had already taken some minor effect and my bust...

Magic Dress - Veronica

by SlightlyRude on Jun 8, 2020
Transgender & Crossdressers

CHAPTER 1 My name is Vernon. I was 27 years old and I didn't know what to do. It was six o'clock and there was no dinner. Auntie Monica had not come home from work. I can get a drink myself so I had some cola. It got dark and no-one closed the curtains. After not having dinner I went and played on the games console as usual. I wasn't sure if it was allowed,...

To Smell a Rose for the First Time

by eatu55 on Mar 27, 2018
BDSM

Recollections of an encounter- "What kind of wine would you like me to bring?" I emailed her. The message came back, "Malbec." Good choice. I really like the dark berries and spiciness that Malbecs possess. They sip well all by themselves, though I was hoping the pairing for this one, tonight, would be more than just a nice wine tasting. She had a light...

A Cuckold's Diary Pt. 04

by Robsound on Nov 6, 2017
Loving Wives

I gave the girls half an hour head start then got changed and headed towards the bar where I knew they were going to start their evening. I got to the pub about forty minutes later and slipped in through a side door and looked around for my wife and her sister, and spotted them chatting to two guys. I decided to try to get closer for a better view. I sen...