Transsexuals+&ampamp;+crossdressers Stories

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Do You Know A Cross-dresser?

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Trans-genderism: Cross-dressing I never considered writing a story about cross-dressing until I was confronted with it. I just recently found out that a friend of mine who I have known for several years is a cross-dresser. He's a good guy, a family man, is married with kids, and, by all accounts, appears normal. Whatever that means? Yet, what is normal? Am...

Just Curious

by Bakeboss on Sep 16, 2017
Transsexuals & Crossdressers

I know all these stories start out this way but I am not gay. I'm married, I have kids, and I've never had a gay relationship. Still with all that said, lately I've had a burning desire to meet a live transsexual. No that's not the truth I want more than just to meet her I want to explore her body. I'm not talking about a boy in a dress but a female with a p...

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...

New Horizons

by Moonm8 on Sep 16, 2017
Transsexuals & Crossdressers

Pete always was very open sexually speaking. "Don't knock it if you haven't tried it" was his watch-phrase when it came to sex. Being alone in a faraway land had just emboldened him a little more. Lately Pete had found himself fascinated by transsexuals whose pictures he'd seen on the Internet. It was beyond his reasoning how a beautiful woman with a pair o...

From Tomboy To Boy

by PredatorSmile on Sep 16, 2017
Transsexuals & Crossdressers

Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class couple, a policeman and a teacher. Mike Flannigan went to colle...

Shemale Thressome

by trentdolby on Sep 12, 2017
Transsexuals & Crossdressers

I met Chrissy about a year ago at a bar. We really hit it off. She was about 5'5" 120 with a nice, athletic body. She was Filipino. Her face, well, unless you knew, you would never know. She was different than the rest of the girls at the bar. While she was there to make a living, she was also there to have fun, with the right guy. Fortunately for me, I was...

June Meets Dale

by june613 on Sep 14, 2017
Transsexuals & Crossdressers

I've been wearing Pantyhose for almost 30 years now, and I still have as strong a Fetish for them now, as I did back then. About 17 years ago I started meeting other Pantyhose Crossdressers or Pantyhose Lovers for Kinky sex. About 4 years ago I replied to a posting on Craig's List from someone looking for a Pantyhose Crossdressing partner. We met in stree...

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...

Sawsan, Liban and Joanna

by Samuelx on May 14, 2018
Transsexuals & Crossdressers

Meet Liban Sheikh and his wife Sawsan Aoun-Sheikh, they're a lovely couple living in the City of Toronto, Ontario. Liban is six feet tall, slender, with dark brown skin and curly dark hair. A fine exemplar of Somali-Canadian Muslim masculinity. Sawsan is five-foot-ten, curvy and sexy, with long blonde hair and lime-green eyes. By all regards, they appear to...