Sissygasm Chastity Stories

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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...

Daddy's Little Sissy Diaper Slut

by Satanicsissybitch on Jul 14, 2020
Transgender & Crossdressers

I absolutely love wearing my adorable pink pull-ups for Daddy and I really love being his cute little sissy diaper slut! Daddy had always loved playing the dominant role with women but it was me who has him addicted to sissies and I've always been a little diaper slut. Well, a pull-up slut anyway. I always felt the adult diapers were not only boring and blan...

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...

Sindys Undoing

by SindySuxALot on Sep 26, 2017
Transsexuals & Crossdressers

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Corn...

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...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

Sissy Fluffs an Orgy

by yvetteinpanties on Sep 25, 2018
Transsexuals & Crossdressers

For years, I would seek out a new sex partner every six months or so. However, over the last year, I have become insatiable for cock. My male sex drive leaves me wanting it all the time, and, as a sissy, I don't need an erection to have a good time anymore. I can be a sissy slut whenever the opportunity arrives. Last night I found a new group on a social n...