Sissygasm Chastity Stories

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Infinite Scroll

Cockland Island Pt. 04

by Sissyhalo1 on Dec 16, 2019
Transgender & Crossdressers

It was one of my first lessons as a sissy that I learned on my own. New girl only appealed for some men. And there were all sorts of hotter sissy girls there just working it in the food hall and other places. With real breasts or close enough, with great asses that were getting attention. And as femmed up my brain was there was still this sort of competi...

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

My Bestfriend's Girlfriend

by Shauna_Wood on Jul 9, 2019
Transgender & Crossdressers

When I was in my early 20's I used to play a lot of online video games. First person shooters, mostly. The Battlefield series, especially. I had started playing games online with a guy named Chris who had gone to high school with my ex-fiancé. He and I had met through her and had really hit it off. We had remained close even after she and I split. He lived u...

Sissy Dust Pt. 03

by Sissyhalo on Sep 11, 2018
Transsexuals & Crossdressers

*Before... I lose track of everything after he seeds my insides and kept going. No not everything. Three highs after the mixture entry affected me. Three times Steven came inside of me. I dimly remember the clock. And my body in some sort of perfect fuck shock after he was done and shaking with him vibrating too our hearts pounding after that and him s...

Awakening My Inner Trixie Ch. 02

by Sissyhalo on Jun 5, 2018
Transsexuals & Crossdressers

For everything that happened I slept really deeply. Waking was a bit of a thought storm though with me realizing that Kiki's in bed with me snuggled up and her huge tits were pressed into me. Then there was this feeling in my ass. She fucked me last night twice after fingering me and vibing me and she was good at doing that. I didn't hurt, I definitely f...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

Awakening My Inner Trixie Ch. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18+ years old. *** I was as stunned as everyone else was when Kiki came into the comic shop. Oh sure we had girls come in but we never had a girl as gorgeous as Kiki come into the shop and she was tall and had the most stylish red hair just kissed with blonde that tumbled down in these long waves and she was in this tiny little dre...

Sissy for Mommy's Nipple Cream Ch. 03

by ppeaks42 on Mar 6, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Recap ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ While raising her son Jim as a single mother, Julia developed a special bond with him by never stopping breastfeeding, which had the side effect of growing her breasts to a monstrous H-cup. Once Jim hit puberty, Julia made him start d...