Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Her Male Wife Ch. 02

by Zippeduptight on Nov 19, 2018
Transgender & Crossdressers

I kissed Tina's boots as the two ladies lounged above me on the couch drinking red wine. The taste and smell of her suede boots mixed with her perfume caused me to get excited again in the chastity device. "I've been sooo horny, and there are just no good men around. I'm so glad you let me come over and play." Tina's voice stretched out. "You're welcome an...

The Roommate Pt. 08 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Lori became used to the chastity regimen, the occasional Nair, the wig (Miranda estimated only a month more with it), and continued dutifully teaching Josh/Lori's college classes on into the spring semester. She began to wish she could dress as Lori all the time, and when at college or researching in a library, sometimes ached to be feminine, and to look a...

Caught

by ImpureChastity on Sep 13, 2017
Transsexuals & Crossdressers

I had been planning my downfall for weeks. Putting together the right outfit, working out the best place to be in the house, practicing my lines to appear convincingly surprised, everything was lined up perfectly. For a few months the relationship between me and my fiancé, Janice, had been just a little kinky. She had cottoned on to my submissive tendencies...

Simply Submissive

by cdnoir02 on Dec 16, 2019
Transgender & Crossdressers

It was an ordinary night, apart from the fact that I had something extra special planned. I had been talking to a man (we'll call him 'J') online for a few days now, and after exchanging some pictures and contact information we had agreed to meet up. I had gotten home from class around 9:30pm, and immediately went into the washroom with a razor to make sure...

The Roommate Pt. 06 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Josh/Lori continued to endure a burning ass throughout most of the following day, but by the time he returned from teaching, the sting was more of a memory. He helped prepare the evening meal just as Miranda directed, reveling in his/Lori's long skirt, breasts, hairdo, earrings and bracelets, and slip-on sandals with heels. She had even applied a little li...

Sissy Life

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here.... I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, s...

Master's Femboy Maid

by KittyAshleyy on Apr 14, 2020
Transgender & Crossdressers

Ocean blue eyes looked back at me as I looked myself over in the mirror. My Master was hosting a get together of his like minded friends and had told me to dress in my best maid uniform. That was a black maid dress with a skirt that barely covered my ass, white gloves which reached past my elbows, a small white apron and fishnet stockings with a black garter...

Scene from a Bathroom

by MaidinChelsea on Sep 16, 2017
Transsexuals & Crossdressers

This story is a another snapshot of the world created in Scene from a Dinner Party. ***** Click... Click... 'and...' click! 'Perfect!' my Mistress says with wicked glee, 'now up you get.' A sharp intake of breath and my eyes widen but I place my hands flat on the cold, tiled floor and... my Mistress giggles, 'Sophia, Sophia - stay down. There's no way an...

Helen Ch. 11

by Philippasubmaid on May 14, 2018
Transsexuals & Crossdressers

This story is a graphic tale of a Dom and his very submissive transgendered males. If you are offended by tales of BDSM and sex between consenting adults then read no further ......... other wise enjoy It is best if read with previous chapters. Feel free to leave honest comments or suggestions, it really does encourage those of us who write to continue......