Sissy Shemale Stories

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Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Bitch Maker Ch. 04

by YANKEE DAN on Sep 12, 2017
Transsexuals & Crossdressers

"Fuck you Excel." I muttered. It was Monday morning and I was at work, but I hadn't managed to do much. I had to get cell G14 to show the total of B2 through B10 divided by B12 plus the total of C2 through C10 divided by C12 but every time the box just displayed a bunch of Xs. I had done this kind of thing before but something was off. I should probably...

The Making of an Angel Pt. 04

by AngelLawrence on Aug 6, 2019
Transgender & Crossdressers

The story continues with the explanation of how I become a shemale slut. In the last episode I related how I lost my anal virginity to a stranger. All persons are over the age of 18. *** I got home to find thankfully my wife was still out. I stripped off my lingerie before jumping in the shower. My boi pussy was very tender and I gently slipped a fing...

Snapped: Shemale

by Templar_Writer on Oct 13, 2017
Transsexuals & Crossdressers

This is the latest entry to my Snapped series in which a woman has been pushed to the limits and finally snaps to end the torment. I'm glad to be back to writing as I haven't been able to get much done in the past few months. A reminder to anyone who has an idea that would like me to turn into a story, I am enthusiastic about ideas. However if the subject is...

Happy Endings Ch. 02

by desireethtttv on Sep 13, 2017
Transsexuals & Crossdressers

"So Desiree how did you like your first night at Happy Endings Massage Parlor?" queried Judy as daybreak shown through the open doors she was now bolting shut. Speaking with slight hesitation, I told her that I think I could become accustomed to the lifestyle quite easily. "You liked being in control of the men I had you pleasure tonight, didn't you Desir...

TS Princess Ch. 01: Fucked by My Warden

by TSPRINCESS on Sep 16, 2017
Transsexuals & Crossdressers

It had been several weeks since I left home with my cousin brother for my breast-enhancement surgery. All our family knew was that I was going to some cram-school to get coaching for Pre-Medical Exam (AIPMT). My cousin brother had been supportive of me not only since he cared for me; it was due to his own advantage of having a full-formed girl at his disposa...

Peggy the Pegger Pt. 04

by FreakyBiFantasyGuy on Sep 19, 2017
Fetish

All characters are 18 years old or older. This is a work of fiction. ***** Peggy the Pegger Part 4: Pee Party We all have our kinks. Be they anal, domination, BDSM, humiliation, feet, pee, toys or anything else, they need satisfying. And that's why, one day, Peggy and I set about finding all our kinks; and what better way to find them than by trying eac...

Bethany's Secret Ch. 2

by Wannabe Chick on Sep 18, 2017
Transsexuals & Crossdressers

-3- Before beginning my story about what happened to me the week before Christmas, I should explain what had happened during the past few months. Early in my senior year of high school, I had met a gorgeous girl named Bethany who became my girlfriend. On the day of our four month anniversary, we had sex for the first time. What I didn’t expect, however, wa...

Neighbors Sissy Son Ch. 05

by newfield1981 on Apr 18, 2018
Transsexuals & Crossdressers

For as long as Tiffany could remember she always envied real girls sexy curves. Clothing looks so much better on a girl with a nice set of tits and ass. Tiffany spent the night thinking about all the options Dr. Landry offered her. The most compelling option was that he could increase her bust size or ass size, without surgery and that counted for a lot. B...