Sissy Shemale Stories

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Why I’ll Never Go Sharking Again Ch. 02

by tsfan84 on Sep 13, 2017
Transsexuals & Crossdressers

Earlier today, I was raped by a shemale. It was my first sexual experience with anyone not carrying two X chromosomes. It hurt like hell, at first and to be totally honest, I'm still sore. But it also felt really good after a while. The sensation of being.....what's the word I'm looking for here..."filled," while cumming is the best. Having your ass clench d...

A Biker Became My Daddy

by SissyKyliegirl on Mar 16, 2020
Transgender & Crossdressers

I live in a small suburb town outside a bigger city, where I work as a barista at a coffee shop. I'm 5' 4" about 145 lbs. with shoulder length brunette hair. Always getting mistaken for a girl, having a cute round ass and widened hips didn't help, I had that girlish figure that women would die for. I had been crossdressing for years since I moved out on my o...

One of the Girls Pt. 02

by Erotictales4u on Sep 26, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom, maledom and transsexual/cross-dressers niche, it is focused on humiliation. This is the second chapter of One of the Girls. Sorry for the long delay. ***** The studio lights blinded and disorientated me for a few minutes as Lana led me by...

A New Slave Ch. 04

by jdk0210 on Sep 14, 2017
Transsexuals & Crossdressers

Early the next morning I awoke, rubbing the sleep out of my eyes, trying to look around the room. As I looked down, I saw my now cum-stained panties tented by my morning wood. A shift in my weight to get up off the bed reminded me of the plug still lodged in my ass. A familiar taste on my lips brought the event from the night before back into my minds eye ve...

Megan's Bitch

by magicrub on Sep 14, 2017
Fetish

"Why are your clothes still on?" demanded Megan as she smacked her bitch across the face. "I'm sorry Mistress..." bitch replied before being sharply smacked again. "I did not give you permission to speak bitch!" replied Megan. "Besides, a Mistress does not have a cock like this one! Does she slut?" "No Mistr..err Master?" replied the bitch, starring at t...

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...

The Backpack

by ~Etoile~ on Jul 31, 2011
Fetish

Moving to a new place is always rough, but it can be rewarding as well. The Nuwisha Design College in Seaside City is a smallish school, but is known for its art and design classes. A lot of literature and word-of-mouth shows that graduates from this school often get very lucrative and popular jobs. Lucky for you, you were able to get in with some of your gr...

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Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

The Wish of a Submissive Older Brother

by SubmissiveJosh on Dec 20, 2018
Fetish

Hello people, this is my first story, I am not a native English speaker, so the first chapters might have some mistakes. This was already posted up to chapter 14 in other sites so I am just porting the story over to the Chyoa format. I would like as much feedback as possible. Don't be afraid to lay hard on me what you think and how bad my writing is! I would...

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Kitty Ch. 01

by ts_candi on Sep 15, 2017
Transsexuals & Crossdressers

Hi, my name is Kitty. I live in a small town in China, which is more like a large village, with my mistress - Madam Kia. I used to be a man, but I changed. The story of my change is complicated, but I will try to tell it as clearly as I can. I never lived in china, to start with. I was a happy man, all of 24 years old. I loved my women, and I had a fair sha...