Crossdressing Sissy Stories

7,212 results
Orientation
Length
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Infinite Scroll

First Time Cross Dressing

by fethishboy on May 1, 2003
Fetish

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved t...

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Bullied

by Testytesterton on Sep 12, 2020
BDSM

You are an 18 year old boy surrounded by bullies everywhere you turn. Your high school has apparently elected you the mascot of the losers and wimps and selected you to receive the lion's share of attention from the bully boys while simultaneously being ignored at best by the girls you lust after. At home, your family is cruel and controlling or coddling and...

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Crossdressed by Hot Girls

by tgirlchrissy on Sep 16, 2017
Transsexuals & Crossdressers

While I was a senior in high school I had an experience I would never forget. I had a group of girls that I called my "Ladies" and I was always close with them, I even hooked up with 2 of the 6. One summer night there was going to be a party and they were all going so me and a couple of my friends were going to go too. Earlier that day I was hanging out with...

Breeding Natalia

by sweetsatine on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Nathaniel Geller had been a young, up-and-coming salesman at MedZ who'd shown great potential. In just a few years, he made his way from ambitious college graduate to savvy junior manager. Risky ventures that others were skeptical of luckily always seemed to turn out succes...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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Summer Plans

by Weebwithkinks on Feb 21, 2020
Transsexual

Finally summer is here you've been waiting for this for a long time after a gruelling 1st year of university, you can relax for the next 5 months without any deadlines or assignments. You're heading back home for the summer to spend it with your family, nothing special but a much needed change of pace. Last time you spoke to your parents they said nothing mu...

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Witches of Westfield Mall

by Vestiphile on Apr 22, 2019
Fantasy

I was in the Westfield Mall to return a couple shirts that didn't fit me. I knew I should've tried them on, but dress shirts are a massive pain in the ass when you're in a fitting room. All those pins and clips, the cardboard holding the collars and cuffs in place...way too much work. So imagine my surprise when I saw people running or briskly walking out of...

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A day in wonderland

by BadUsername1 on Jun 26, 2015
Fetish

You awaken in a strange room in a haze. Your vision is foggy and you become aware of your body, you feel it dragging as you get up to move. You rub your eyes and your vision clears up. Your first sight is the floor below, its a white and black chess floor pattern. You follow it with your eyes up to the wall, its a regal beautiful pattern, a deep red. Somethi...

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A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...