Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

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...

My Father, The Maid Ch. 02

by SissyOona on Oct 30, 2018
Transgender & Crossdressers

I awoke the next morning fairly early. My sleep had not been as restful as I would have hoped due to the revelations of the previous day. Eventually I pulled myself away from the supreme comfort of the bed and stumbled to the bathroom to take care of my morning business. As I exited the bathroom I could hear the sounds of breakfast being made from the kitche...

Merry ChristmASS, Bitch Boy!

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

The holidays were upon us. I had spent the last three months of my life as the personal sex slave of Brittany Andrews and Chantz Fortune. By now I was used to the chores, and the beatings, and constantly servicing and being fucked by their various strapon dildos. However, I never got used to the humiliating situations that they placed me in on a daily basis....

An Uneven Christmas

by libertinaXx on Sep 13, 2017
Transsexuals & Crossdressers

By Christmas, Sarah and I had been 'dating' for a few weeks. If you could call it that. I had been spending a lot of my time with her but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. M...

Just Like My Friend

by purekink on Sep 12, 2017
Transsexuals & Crossdressers

I suppose it all started after my friend told me his girlfriend liked to dress him in her clothes before sex. I couldn't quite believe it - he was masculine and muscular, a real man's man. He'd confided in me and I teased him about it unmercifully. I mean, really? Being dressed in women's clothes? That was supposed to be a turn-on? He seemed to think so, bu...

Mr. Asshole, My Submissive Super

by Goddess_Meanie on Mar 7, 2018
BDSM

Let Me tell you about me. I mean, what I want you to know. I really do enjoy the life I live, I wouldn't trade it for the world. It wasn't always good though. All my experiences have brought me to where I am today. I like to think I'm a great judge when it comes to people. I can spot a weak man a mile away and once i have them in my grasp I do what I want wi...

Neighbourhood Terror to Sissy Pt. 22

by Fibaro on Jul 6, 2020
Transgender & Crossdressers

Chapter 24 "Okay Marcy, now get back up and Minthe back to the vanity table. Jutht like it'th important to know how to apply makeup, it'th important to know how to remove it ath well. After all we don't want you developing a bad thkin cauthe of all the makeup you're uthing." Stephanie ordered not even giving Marcy a few minutes to deal with what had just ha...

The Seven Dressing Sins: Vanity

by purekink on Jul 15, 2020
Transgender & Crossdressers

"To recreate this scene, you will need..." John tightened his calf muscles as he watched the young woman on the TV present an untidy scrap of cloth. "One white fishnet dress." He thought he knew her, somehow - something in her voice perhaps. He didn't know anybody with a crimson streak through her long blonde hair. And he certainly didn't know anybody who...

Becky's Video

by purekink on Sep 13, 2017
Transsexuals & Crossdressers

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later -- all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine...

Joel Gets Caught by His Wife Ch. 02

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is the second fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * The next few days went by without much happening. Joel was a bit ill at ea...