Sissygasm Stories

121 results
Orientation
Length
Source
Infinite Scroll

Bambi Takes Over

by bambidoll1 on Jul 17, 2019
Transgender & Crossdressers

The morning sun crept around Darren's dark blue curtain, barely illuminating his apartment. On his bed lay a simpering little black sissy slut, covered in her own cum. Her eyes were closed but she was stirring—Bambi's sleep would be over soon. Her platinum blonde hair was a mess. Her bright pink lipstick was smeared. Her plump lips were heavy and her holes w...

Sucking Her Bull

by pinksissyfairy on Dec 2, 2019
Fetish

"Open wide little bitch", Jason said as he positioned his cunt juice covered cock in front of my face. I was in my usual position, kneeling by the side of our bed naked save for the locked cage denying all hope that I could satisfy myself let alone my wife. Jason then proceeded to slap his 11 inch black beast on my lips, glazing them with moisture straight f...

Subliminal Obsessions Ch. 07

by Sissyhalo on May 28, 2018
Transsexuals & Crossdressers

*Before... But this, this is the big turning point because this, this as hot and as intense as it because it settled into lovemaking and being made love to by this amazing guy that honestly could have all the pussy he ever wants and he's with me. With me making love to me and it's so much more than sex to me right now. And honestly. Really fucking honest...

Sissy Wants Her Wife's Boyfriend Ch. 01

by SissyArlene on Aug 21, 2018
Transsexuals & Crossdressers

I knew that my secret sissy life was about to be exposed. Cindy, my wife, had been dating real men since my hormone therapy had rendered my sissy clit useless to her, but she was still trying to keep our "unique" marriage hidden from friends and family. Two months ago, Cindy said, "I'm tired of trying to keep your transition a secret Arlene. I'm not going...

White Boi Learns his Place Ch. 04

by sissyashley4bbc on Aug 7, 2018
Transsexuals & Crossdressers

It took me a few minutes to recover from the fucking Daddy just gave me at the mercy of his big black cock. I was definitely handling his size better than when this whole ordeal started, but he still stretched me to my limits. As I laid on his chest, his big black cock softening in my boi pussy, I couldn't help but think about how I have been missing out o...

Autumn by Marina Ch. 03

by ashleyw_xoxo on Sep 14, 2020
Transgender & Crossdressers

3. Marina was set to travel for the next 4 weeks on business, so this was our last evening together. We were back at her place, getting dressed to go out to dinner and dancing. I was having second thoughts about going out in public. "Are you sure this is a good idea?" "Autumn, don't worry about it. You're going to look great and who cares? Anyone who does...

Amazon Sissy Jock

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

All parties involved are over 18 years of age. *** It started me going to a party. Now that's not unusual because I'm popular, I've always been popular like ever since junior high. I shot up like a weed getting tall and my dad worked me out while I was going through my growth spurts and had me in lots of stuff like to round me out before I got into footba...

Sissy Pills Pt. 01

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

Some say it was some sort of experiment gone wrong. But it hit the streets and it changed everything. A pill a drug that you took that made you sexually submissive and made you especially sexually submissive to men. Semen made it worse apparently. And there were addicts that ended up not just being gay or fags but entirely sissies and that was fastly bec...

An Unexpected Twist

by Buildaworld on Sep 16, 2017
Transsexuals & Crossdressers

A week has passed since that event and things seem to have become steady again. Gabrielle and myself are in contact every day, Melanie has backed off and everything feels perfect. We even met yesterday for a quiet little meal, but after a meal and a few drinks, I was stretching Gabrielle's tight little pussy and she wasn't being quiet about her pleasure. B...

He Changed Me

by Sissyhalo1 on Dec 23, 2019
Transgender & Crossdressers

I know a lot of these stories are about some guy that watched porn or read it and got hooked or were some short femmy guy that got tricked into getting boned but that's not me. I'm Sam and yeah it's Samantha most of the time now. But before that it was just Sam and I was in my last year in college and to save money to fix my car I moved into a rental house...