Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

The Book of Dreams

by cddannie18 on Sep 15, 2017
Transsexuals & Crossdressers

So there I was, once again sitting at home on a Friday night! I was convinced I must be the only high school senior without anything to do tonight. And just to top it all off... its Halloween! The biggest party and socializing night of the year. I am such a loser. I have no girlfriend... no social life for that matter, and the one thing I really love to do I...

Two Way Display Ch. 02

by seams_straight2me on Jul 15, 2020
Transgender & Crossdressers

Tia: After Zoe had cum over my tits, we cleaned ourselves up. We had a shower, but not together, as we both wanted to just be Tia and Zoe in front of each other for now. With my stockings and lingerie a bit of a sticky mess, Zoe offered to wash those for me, and I could pick an outfit from her wardrobe. Zoe did admit she also offered to wash my stuff to h...

My Friend Ashley Ch. 06

by jealouscuck on Aug 6, 2019
Transgender & Crossdressers

The evening after Ashley and I showered together, she suggested that we start exploring herbal supplements. It came from her complimenting me on my girlish ways and didn't I wish I had breasts like hers. It progressed to the point that I admitted that I would love to have breasts. After hearing that, she told me about her limited research into the subject. I...

Michele Nylons' True Stories Ch. 05

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Mamma J Ch. 01

by Transbabe55 on May 4, 2020
Transgender & Crossdressers

"Mom, what am I going to do about Jason?" My daughter sat facing me seated at my kitchen island with a troubled yet familiar look upon her face. It was the same look I'd seen when she was doing poorly in a class or when one of her friends slighted her. The circumstances were quite different this time, however. She was thirty years old and had just found...

A Big Surprise!

by rj1774 on Jul 6, 2020
Transgender & Crossdressers

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy! **************** My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get a...

Sailing Away Ch. 23

by Jasmyn_White on Jun 1, 2020
Fetish

Lacy, done with her recollection of the trio of BBC, asks, "what do you think?" "I think it went spectacularly well, and I'm glad you enjoyed so much." "Oh, I surely did my bitchboi. And I've got just the way to reward you. In a sense." I knew you had something afoot. "Let me see your cock, sweetie, I want to unlock you so you can shower." Doing as told...

Julia, Ben and Lisa Ch. 18

by chloejacobs83 on Mar 30, 2020
Transgender & Crossdressers

Ch. 18: Friday A few quick notes: 1. this is the eighteenth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned We, Harry and I, were in the elevator but still hadn't said a sin...

The Role Players Pt. 02

by hollygurl29 on Jul 30, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

A Day with Ron as My Master

by Cynthia_D on Sep 14, 2017
Transsexuals & Crossdressers

It was a beautiful Saturday morning without a cloud in the sky and I was enjoying my second cup of coffee while reading the sports page when the phone rang. Hindsight tells me I shouldn't have answered it but hindsight doesn't do any good in the present. I picked up the phone and said hello. It was Ron. I haven't seen or talked to Ron since my birthday and...