Chastity Cross Dressing Stories

77,281 results
Orientation
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Infinite Scroll

A Fantasy with Lisa

by chastityfan on Sep 13, 2017
Fetish

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each oth...

Life and Time of Lady Vargos Ch. 06

by rik581 on Mar 27, 2019
Transgender & Crossdressers

Chapter 6 "Lady of the House" Martin had been home three days from his visit to the spa, and things were now becoming a bit more of daily routine for him as mistress of the household. As usual he had been awakened early by his husband with a long passionate kiss on the lips. Martin grabbed the sheets with both hands and groaned as he awoke in the affectio...

Stocking Sperm Challenge

by wordyone on Jan 1, 2019
Fetish

My sister Dorene was on the phone asking me if I could accommodate her friend Ruby during the Summer holidays. "She's a really delightful woman, generous and easy going, I wouldn't ask you otherwise," said Dorene. Ruby was studying theatre and dance and had to attend a six-week contemporary dance course at the local university. I was certain that my girlf...

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

The Chef Becomes a Domme

by sexynursechef on Sep 15, 2017
BDSM

The Chef becomes a Domme (The Dominatrix Series) I had been taking Dominatrix lessons from Mistress Katrina for months. Being an Alpha Female Russian woman, control came easily to me. I am, and have always been a healer, though. My intention is "Do no Harm", it is part of the Wiccan Crede. So my training had emphasis on getting the client to explore their...

CMDCTRL Ch. 01

by AimeeDaze on Feb 6, 2018
Transsexuals & Crossdressers

CMDCTRL Good evening, Sophia. Did you receive your gift? SOPHIACD18 Good evening Sir. I did, thank you very much. CMDCTRL You have the place to yourself? And you have followed my instructions? SOPHIACD18 Yes, Sir. I have the house to myself all weekend until Monday night and I have dressed as you asked. CMDCTRL Good girl. You may turn your...

Carl & Chastity: 1st Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Carl got to the wine bar about ten minutes late, fortunately he arrived just before Chastity. One thing that he felt never looked good was making a lady wait especially on a first date. The date started a little awkwardly, as most dates do but this one was because Chastity couldn't remember what Carl looked like at all. Luckily for her, Carl more than made u...

For Veronica's Sake Ch. 09

by betamale08 on Oct 5, 2020
Fetish

Chapter 9 Who I am Cry myself to sleep... Yes... That is what I ended up doing after I'd left Veronica naked and in the arms of my friend Reg Morgan... Left her there in his house no less than 800ft away, there left for him to fuck and play with as we'd arranged in this new direction we had taken in our relationship, adding some 'spice' and trying somethin...

B'n'B with Laundry Thrown In

by wordyone on Nov 20, 2018
Fetish

My name is Fam and having spent a couple of years as an online camgirl I had enjoyed so much fun answering the demands of visitors to my private room. It really turned me on playing with the minds of submissive puppies who were seduced by my feet and legs dressed in stockings, pantyhose and sexy little ankle socks. Many guys longed to grovel at my nylon enca...

Shopping and Sucking

by Subkoksukr4u on Mar 2, 2020
Fetish

Matt was in the kitchen as usual preparing breakfast. He'd been instructed to prepare all the meals according to a specific menu plan each day. He finished the sauce for the eggs Benedict got on his knees and waited. He was wearing frilly pink crotchless panties and a matching bra, his bright pink CB 6000xs chastity device was barely peeking out between...