Master Sissy Stories

61,161 results
Orientation
Length
Source
Infinite Scroll

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

The Man That Owns Me Ch. 04

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Don't be shy. Pull your panties down, baby boy. Show the man that cute little thing." He laughs, smiles at me. He's seated on the couch next to a man I've never seen before. When they entered my house I expected only him. I hurry to do as told. It's something that is part of me now. I never hesitate to do as he orders, dominant of otherwise. He owns me com...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by...

The Night He Started Showing Me

by SissyCinnamon on Sep 16, 2017
Transsexuals & Crossdressers

Mistress walked into the kitchen where I was cleaning and informed me that I was to stop and get ready. "Get your swishy ass upstairs and clean up. You have a date tonight." Mistress said. "A date, Mistress?" "Yes, you ditz. There's a man in town who very much wants to meet you. And you WILL behave for him! Understand?" Mistress was quite stern. "Yes, Mi...

March Madness Ch. 09b

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

Tales of Sub Asian Sissy Ch. 03

by subASIANsissyJADE on Apr 23, 2019
Transgender & Crossdressers

(Thanks so much for taking the time to read my story! This is just my third post and I'd love to hear any feedback, questions or comments. Also, please feel free to contact me if you just want to chat with a very submissive asian sissy. XXX, jade) *** While it's only about fifteen minutes away, the drive back to my apartment seemed to take forever. I had t...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

Randi Michelle's Sissy Subjugation

by Randi_Michelle on Sep 16, 2017
Transsexuals & Crossdressers

To me, part of the process in my case of stripping me of my masculinity involves documenting my transformation and the humiliation that it would involve. For me it started through an encounter with a dominant man who enjoys feminizing submissive males and turning them into 24/7 gurls. It just took the right dominant man to make it happen for real. I've spen...