Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Barrack Room Betty Ch. 09

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Nine - Pink Pussycats All good things come to an end and the six-week Reduced Operations Period at HMS Chelmsford ended on 15th January 1974. The Wrens and Leading Recruits were very busy as that day approached. The Depot needed to be de-winterised and preparations made for the return of the Ship's Company, the recruits, and the Wrens from their l...

Caramel and Devin

by CaramelBlack on Jan 31, 2018
Transsexuals & Crossdressers

*** All characters are 18 years of age or older*** ***** One good thing about my having been a teenager before the Internet age began booming was that I had no knowledge about society's labels. I didn't understand the difference between crossdressing from transvestism or a transgender person from a transsexual. There was no pressure to try and figure out...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Crossdresser Husbands Left Alone

by ColorfulFantasies on Sep 12, 2017
Transsexuals & Crossdressers

Once my wife, Jessica told me she wanted to see this new opera play. I told her I didn't want to, but she wanted it so badly, that I told her to watch it with one of her art-loving girlfriends. She said: -I will ask Amy, then. -When do you want to go? - I asked. -Tomorrow night. -There will be match tomorrow night. I think it will be a very good match....

The Public Adventures of Mark Ch. 03

by rik581 on Sep 15, 2017
Transsexuals & Crossdressers

"Come on Mark," Cindy said as they pulled up in front of the nail salon in the shopping center. "Time to get your nails done," she laughed and patted him on the shoulder. Cindy was so good at this public humiliation game that she played for Mark. It was because she cared so much about him and knew it was such a deep passion and turn on for him once she got h...

Laundry Date

by Rallynoangels on Nov 27, 2017
Fetish

This story contains light femdom, humiliation, and crossdressing themes. All characters are 18 or older. ***** She did enough housekeeping at work, and now her Friday was taken away from her because of even more cleaning. Four year degree and what did she get out of it? A stereotypical maid's salary at a hotel that paid just enough for her to live in a ru...

The Guy in My Wife's Panties

by Candyboi on May 1, 2018
Transsexuals & Crossdressers

The catalyst for the paradigm shift in the relationship with my wife of twenty years was something that happened at the beginning of December - though, truth be told (as you'll see), there were several other naughty escapades throughout the autumn that really should have awoken me to the realisation that Carla was becoming the dominant one in our relationshi...

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

Dawn's Diary Ch. 03

by dawn43 on Sep 15, 2017
Transsexuals & Crossdressers

Back at home it took nearly a week before I was able to sit comfortably after my encounter with Sam and her huge dildo. My thoughts constantly drifted back to her. I continued to keep my body cleanly shaven and regularly wore the outfit that I had worn that evening with Sam around the house. I bought a butt plug and inserted it on arriving home most evenings...

Lessons with Kelli Ch. 02

by Lifeatlarge on Sep 12, 2017
Transsexuals & Crossdressers

Writers Note: This is the second chapter in the story of how I met and came to love a very special lady. There is one more installment after this one. * I usually shower at night and before I got in on Monday, I decided to shave off my body hair. I had never done this when I had been crossdressing before, but I figured why not give it a try. The hair on m...