Crossdressers Stories

12,121 results
Orientation
Length
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Infinite Scroll

The Shoe Store Slave

by YoungSub13 on Nov 18, 2019
Fetish

I am such a pervert. I've been a dirty boy since junior high when I was obsessed with porn. High school wasn't any better, in fact it just got worse. So now here I am attending college in Boston the ultimate college town. It was the beginning of my senior year and I figured that since I had a somewhat easy schedule that I would get a part time job. At first...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Michael Begins His Exploration

by cuckietex on Sep 15, 2017
Transsexuals & Crossdressers

The last year had been tough for Michael. His porn collection had not only been found on his computer by his wife of ten years, but she had no idea of his fetish having taken on a life of its own, and she divorced him for it. Looking back, he could not really blame her. She had indulged his passion for stockings by wearing them almost whenever they had sex,...

Allen

by IRivera719 on Dec 25, 2019
Transgender & Crossdressers

Allen shaves, his eyes focused, the lights of the bathroom vanity dancing as he does the practiced moves for the umpteen-millionth time. He still enjoyed it and he enjoyed the fact that each morning presented him with a very male challenge. Last few touches and he rinsed the razor, rinsed his face, looked at himself in the mirror and smiled. He was nude, his...

Tranny Chasers: Bernie and Ron

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Bernie looked around as he entered the Cavalier d'Eon, checking out the patrons. Spying his friend Ron, he worked his way over to him. Ron was sitting at the bar, back to it, also checking out the patrons. "How's it hanging, Ron boy," Bernie asked, easing between Ron and the guy sitting next to him. "Low as usual, Bern," Ron replied, turning to his beer on...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

The Bargain Dress

by HeatherMaureen on Sep 25, 2017
Transsexuals & Crossdressers

I was in my late teens before I found out how submissive my dressed self was. I'd never really considered myself to be a submissive sissy crossdresser but was about to discover that I was one. I called an ad about women's dresses, heels and other things in the local bargain finder from a payphone. An older woman answered. She wasn't taken aback by my tellin...

We Dot Our I's With Hearts Pt. 01

by VSsissy92 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: This story contains transgender and crossdressing themes. If you are not comfortable with these, please go to another story. All names and places are fictional and not intended to represent any real place. All characters in the story are over the ages of 18. ***** Belleville is a semi-suburban town in southern California. Belleville does not bo...

College Life 101 Ch. 2

by AJ on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 2: The Bar After my experiences with my sister Kayla, my sex life changed dramatically. I went from a mild mannered horny guy to this sex hungry creature. The whole first week of college I spent thinking of my younger sister's hot little pussy and how I loved having her muscular legs wrapped around my head. I also couldn't shake that feeling that I...

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...