Sissy Game Stories

87,858 results
Orientation
Length
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Infinite Scroll

The Whore Wife, Sissy CD Husband

by MILF4black on Jul 27, 2020
Transgender & Crossdressers

This story is completely fictional. All characters in the story are over eighteen. Prologue: The Whore wife, Sissy CD Husband "That's it, you little sissy whore, suck that cock." Jennifer told her husband as his head bobbed up and down on the strap on dildo Jennifer was wearing. Her husband, Patrick, lifted his head and the seven inch fake penis slid out...

Sara Shows Her New Man Self Love

by Sexy_SaraCD on Sep 13, 2017
Transsexuals & Crossdressers

I felt vulnerable for the first time as Sara and while part of me was nervous, almost hesitant, the other part of me was exhilarated. I felt nothing more than curiosity as I faced an unknown scenario and what it would lead to. I met Daniel much like I've met most of the men I did as Sara. Except this wasn't a post of mine on Craigslist. This was his post a...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Caught by the Past Ch. 03

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 3 - Friends United Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your...

Superbowl Bet and Payoff

by will4play2 on Apr 22, 2020
BDSM

Randy and I had been playing a lot online but wanted to realize our relationship in real-time. And so it was we agreed to meet face-to-face. Yet every time we would set up an appointment, Randy would cancel last minute. Randy finally admitted, I'm apologizing to you a lot these days. Though we are both switches, I have always considered myself slightly mor...

A Game within a Game Ch. 02C

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 2C. Dr. Catherine. The next morning when Rob wake-...

Legally Binding

by MistressMtoyou on Aug 31, 2017
Fetish

As I explained in my first story (My first submissive), I'm fortunate to have a high paying job at a large well known firm. While my employer is equal opportunity and all of that, even the most open minded employer wouldn't react well if they learned they had an amateur dominatrix on their senior staff. Accordingly, before going much farther with my little h...

Neighbourhood Terror to Sissy Pt. 18

by Fibaro on Mar 10, 2020
Transgender & Crossdressers

Chapter 20 Marcy had a wonderful night's sleep while she didn't realise it, the only reason she had a quiet night was because Lisa had demanded it. What he also didn't realise was that while he was sleeping peacefully John was setting up a website, turning him into a real pornstar. Once it was online John hoped he would make a good amount of money off his s...

You're Like a Little Boy at Times Ch. 03

by Myneed on Aug 30, 2017
Fetish

This is a slight twisted femdom love story that will make most sense if the chapters are read in order. The characters don't seem to want to engage in safe sex, but in the real world we should. Enjoy. All characters are over 18. ***** My heart ached for Mel. It had been another long week another long week of edging and chastity at Mel's instruction. Th...

My New Digs Ch. 02

by cuckytoher on Aug 21, 2018
Fetish

The ice cold water hit my tired body like a thousand stinging needles as the lights went on at 6 a.m. I jumped up from the floor to finish my shower in the two minutes allotted to me by Andrea and Marko. I quickly soaped myself up and rinsed myself down knowing the clock was ticking. If I lingered more than two minutes, the door would automatically lock and...