Sissy Game Stories

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Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

First time Sissy

by PR Sissy on Sep 29, 2019
Transsexual

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any s...

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Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

Linda

by ofloveandlust on Sep 16, 2017
Erotic Couplings

"How old were you at your first?" "Oh my god, you don't ask a woman something like that!" Linda elbowed him in the gut. It was flat and hard as a rock and she was probably more turned on by it than he was injured. "Vut? I can always Google it." His accent wasn't all that thick but from time to time it would be noticeable. That turned her on too. If they ha...

Discovered at the Bar

by CrossdresserCaitlyn on Mar 25, 2019
Transgender & Crossdressers

It was 9 pm on a Friday night and I was just getting off work. It was a long day of running meetings and I really needed a drink. I was out of town and didn't know anyone so I decided to go to the bar by myself. As I sit down at the bar I take off my suit coat, untuck my shirt and loosen my tie and ask the bartender for a Jack and Coke. The first drink did...

Proud To Be A Sissy Ch. 09

by Kary_M on Sep 26, 2017
Transsexuals & Crossdressers

"I hope you like them," daddy stated cheerfully as he lifted the towel from my face while handing me a bra that was laced with trim, matching my panties, "they look great on you sissy." Looking down I saw two flesh toned swells that weren't there before and sitting up I could feel a slight weight pulling down. I jumped off of my bed and stood in front of th...

Card Shark

by Turned on Sep 14, 2017
Loving Wives

I returned to my hotel room from a poker tournament and realized I'd forgotten my key, so I knocked. After a few moments the door swung open and my pretty, young asian wife was waiting for me behind it. "Hi honey," she said, giving me a very strange look, "How did you do in your poker tournament?" "I did ok. Third place. I made a little money," I said, s...

The 19th Hole

by skywayscribe on Sep 12, 2017
Group Sex

Sissy and Michelle were having lunch downtown Minneapolis when Michelle starting asking Sissy how Chuck was at fucking .... Sissy got wet then and there and told Michelle, "If you only knew...." Who knew that would be the beginning of a fabulous experience for Chuck ... and Michelle ... and Sissy. Michelle and Sissy continued their afternoon downtown girls...