Sissygasm Chastity Stories

6,936 results
Orientation
Length
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Infinite Scroll

Jessica Ch. 02 - Vanessa

by Floydman1 on Dec 16, 2019
Transgender & Crossdressers

Her name was Vanessa. She was very cute, about 5'4", slim, with big brown eyes and skin that was very clear and smooth. We had met online, of course. She had reached out to me for advice and friendship, as I was an experienced transwoman. After talking online first and then over the phone, we met in person. It was at her place, since she wasn't all the way...

A special Christmas

by Chuveiro on Dec 17, 2018
Fetish

It was already December and I was home alone. Mommy had gone shopping all things she would use on Chiristmas dinner, which would be at our house. I went to my room and got my clothes and toys. I was a sissy, but nobody in my family knew that. The only person who lived with me was mom but she was so old she couldn't notice anything. I dressed up and started t...

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A good fuck

by sissygasm on Feb 10, 2016
BDSM

This story will contain : bdsm, fantasy and sifi elements, gay sex, sissifacation, transformations and various other kinky things. You have been warned. First a description of the world this story will take place in: In this world things are simple, there was a natural order to the way the world worked: real, strong, masculine men were at the top and then as...

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Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

White Boi Learns his Place Ch. 05

by sissyashley4bbc on Aug 28, 2018
Transsexuals & Crossdressers

After the night at the club, I was completely and utterly Daddy's black cock loving sissy, Ashley. I had a deep crave for his big black cock that was unlike anything I had ever experienced, and after my full public display at the club, there was no hiding it. Not only was there no point in hiding it, I didn't care anymore. Something changed in my mentality...

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...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

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...