Sissy Game Stories

87,858 results
Orientation
Length
Source
Infinite Scroll

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...

A Sissy's New Daddy Ch. 04

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

It was with great pleasure that I am finally able to upload chapter 4 of "A Sissy's New Daddy" I have spent the better part of a year working on this chapter. I was surprisingly hard to get down on paper. I want to thank all the readers that have taken a time to comment and rate the chapters of this story. It has meant a great deal to me and has at a few dar...

Sissy Awakening Ch. 03

by Torbjornson on Oct 5, 2020
Transgender & Crossdressers

Standing at the living room window with the windex and paper towels, I teetered on the ridiculously tall Mary Janes. It were as though I were standing on the balls of my feet and toes only. There was no relief. My other pumps felt like heaven compared to these! She said to wash inside and out, and not to miss a spot. That meant I'd have to go outside. It wa...

Oh, Mr King! Pt. 05

by exaucer on Mar 6, 2018
Transsexuals & Crossdressers

At some stage during the night I became aware that Mr King was trying to push his fat cock back into me again. I was too weak to resist, not that I wanted too, and too far gone to fully participate, so I merely adjusted my position to facilitate his penetration. Since my pussy was still slick and sticky from his earlier deflowering, Mr King's cock eased into...

Connie's Move Ch. 1

by privy2u on Sep 17, 2017
Loving Wives

Connie had lived in her apartment for the last three years. A friendly contest with her landlady gets serious and is taken to the limit. They may be friends, but only one can win! By LEC (a.k.a. Privy) As we pulled out of the parking lot at "Paco's Mexican Restaurant" I was listening to the new exhaust on my restored 66 Chevy pickup. My wife thought it wa...

Gothic Sissy Gets Gangbanged by BBC

by Satanicsissybitch on Apr 17, 2019
Transgender & Crossdressers

I'm really a pretty normal girl for the most part. Normal in the sense that I'm not unlike most people. I love music, albeit heavy metal, I love clothes and shopping, although most of my wardrobe is made up entirely of black dresses, band shirts, fishnets and cute thigh highs. I love to read and write, I love hanging out with friends and going out to concert...

Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

Isabella's Reversion Pt. 04

by silverbackteddy on Sep 11, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Miss Annabelle Ch. 02

by Timewarp10 on Oct 16, 2018
BDSM

As Annabelle's first term at University drew to a close, I had become her slave: cleaning floors, laundry, ironing, cleaning her shoes, making her bed, sorting her clothes and other household chores. Each day was filled nonstop with toil, from early morning to late night, stopping only when she had gone to bed to sleep, and even then I would have to be alert...

A Game within a Game Ch. 02D

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2D. Another session - or not. The next morning...