Crossdressers Chastity Stories

18,166 results
Orientation
Length
Source
Infinite Scroll

A Slut's Triangle Pt. 13

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

It's 7:19am. Surprising, I'm still awake. The storm clouds have cleared over Atlanta's twilight skies as daylight begins to seep through the cracks in my bedroom blinds. The sun will be up shortly to dry up the puddles of rainwater. Both Kimberly and I should be passed out and asleep by now, but our conversation has kept us awake talking about this, that, an...

Three Nights in London - Night 01

by Nymanirene on Sep 19, 2017
Transsexuals & Crossdressers

I met Gabrielle on a music festival where I played with my band. After our gig she complimented me on our show and we started to chat. She was over from the UK and stayed with friends in Amsterdam. I was impressed by this pretty redhead, dressed in a bit of a Lolita style with ultra black make up, a cute red tartan skirt and huge boots over fishnet boots. We...

A Not-So-Small Piece of Heaven Ch. 02

by xTrailx on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning and groggily rubbed my eyes. I tried to remember everything that had happened the night before. It all came flooding back to me. I remembered going to dinner with Vicky, her spraining her ankle, us coming back to her apartment, the initial kiss, the trip to the bedroom, and finally her big surprise. And it was a big surprise. I glanc...

Inaugural Crossdress Sexfight Ch. 03

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The third match of the season matched me up against another rookie that shared the same name as me. Dani had read my stories on the internet and enjoyed some of my photos on Flickr and wanted a match with me. I guess it would seem pretty enticing as I'm sure he was noticing that I was seemingly now a jobber. I had seen Dani's photos on Flickr as well and we...

Hi, My Name Is Hollie! Ch. 02

by JohnB73 on Sep 12, 2017
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction. Complete and utter fantasy, based on an old RP character of mine. I reserve all rights, etc. Also, the way things work in this story may not be an accurate account of any real scientific facts regarding the intersexed. It's meant as erotica, not a medical treatise. Try to relax and enjoy the ride. Anyone interested in u...

The Transformation Device Ch. 02

by Miles63 on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: Apologies for the major Delay in the second chapter, your messages of support and love of the story have been overwhelming so thank you so much for that. Unfortunately I work in retail and I have just finished working the busiest period of the year so when you're tired after work your imagination switch's off so I have been unable to write. Now...

Lady In The House Ch. 16

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 16 -- The Conclusion After putting this story to bed in July 2005 and then reviving it again in March 2007, I have finally run out of ideas for our intrepid transvestite prison prostitute. That said, after you read on and see how I have ended the series, you could argue that there is plenty more to explore in this story; especially the development o...

Teresa's Change

by Mr James on Sep 16, 2017
Transsexuals & Crossdressers

I stood in the shower, letting the hot water beat against my face and skin. My long hair clung damply to my neck and I carefully played the jets of water over my chest. Mom had taken me to see a doctor, just after my twentieth birthday and he had given me tablets to take every day. Mom had told him that I wanted to grow a nice firm pair of breasts and, for a...

A Damsel in Distress Ch. 04

by TheSissySir on Aug 30, 2017
Transsexuals & Crossdressers

Disclaimer!! All parties involved are over the age of 18. This is a story more focused on the characters and plot so there may be little to no sex scenes in a few chapters as I want to develop the characters themselves. This story also contains some incest so if that's not your thing, then I suggest you leave now. ***** Cedric woke up wrapped in his sti...

The Care Girls Ch. 06

by Tomsparty on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 6 - Alone in the house. Later that day you pop round to Becky's. It felt great telling your mother that you where going to see the best looking girl at school. She was so proud of you - little did she know. Becky was not along in her house but her parents don't mind as she leads you upstairs to her bedroom. You're amazed at all her beautiful clothe...