Sissygasm Chastity Stories

6,936 results
Orientation
Length
Source
Infinite Scroll

Passion to Paradise

by giandomenico on Dec 24, 2019
Transgender & Crossdressers

(This story contains much sibling and father-son incest) *** I met Victor Belsay on a building site near the small market town of Castleborough. He was renovating a cottage and I was feeling disenchanted with city life and looking for somewhere to live, where I could get my head together whilst recovering from a badly bruised ego, the result of my lover ha...

Sissy Dust Pt. 01

by Sissyhalo on May 29, 2018
Transsexuals & Crossdressers

All characters are over 18 years of age. ***** I'm not a genius or anything but I did get a decent job out of university with my bachelors of chem and started working in a cosmetics company. No not the testing division but in formulations. And it's a boring job really past the actual chem coolness of seeing reactions happen in new things and the way thin...

Making a Sissy Jock Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I stared at Robin's card for an hour sitting in my truck completely freaked out and every time I touched my lips I felt that friction of Robin's cock. I tasted him. I got slammed with the realization I drank his cum and it was inside of me. I sucked cock and drank cum and just like the sissy porn stuff said I liked it. I was beyond freaked in going to th...

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

Jock Princess Ch. 01

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

I'm Alex. And I got to admit that life's been kinda good. Cake actually. I'm a jock, left winger hockey player and all through high school it's done me pretty well. My family owns a good business in town actually a few of them. Grand dad on mom's side had a dairy farm and actually did okay, Mom's a registered nurse, my dad owns a big hardware store and ad...

Chinese Turn-out Pt. 03

by Sissyhalo on Jan 1, 2019
Transgender & Crossdressers

I crashed harder than anytime ever in my life and my dreams were fucking vivid. I dreamt of being fucked. And of sucking huge cock and getting face fucked so hard that I was cock drunk and high from holding my breath so much. But so really horny from him doing that, so into that cock. Of Jax fucking me so hard that it is still in my head. In me. I hurt....

Romancing the Raptor

by Cashmere_Snow on Sep 15, 2017
NonHuman

Tiffany. Maria. Sandy. Destiny. Chastity repeated the names to herself as she directed a coy smile at the man she had brought back to her apartment. Tiffany. Maria. Sandy. Destiny. They were the names of the women he had raped and then sent to the grave in one case and into the ICU with the others. They were women like her—women who shared an... affliction...

Chastity Debauched: Penitent

by MorganHawke on Sep 15, 2017
BDSM

In Which Chastity has an appointment with the Unholy Father... For Bear Part One: The Club “I can’t believe my Dad had me to come to his company pool party at the Club.” Chastity grumbled to herself while standing before the tall mirror completely nude. She stared into the mirror’s reflection of her deep violet eyes as she tied her waist-length, strawberr...

Secrets of the Deep Ch. 01

by Lady Malachite on Sep 14, 2017
Sci-Fi & Fantasy

Once upon a time, when magic was everywhere and wishes still came true, there was a tribe of women of such distinguished beauty and insatiable lust, that the sun itself stared open-mouthed at them, and the corals turned their heads to listen to their sinful moaning. And because they seldom were seen in anything resembling clothing, they were known in the hea...

Carl & Chastity: 1st Date

by Ninjafish on Sep 14, 2017
Erotic Couplings

Carl got to the wine bar about ten minutes late, fortunately he arrived just before Chastity. One thing that he felt never looked good was making a lady wait especially on a first date. The date started a little awkwardly, as most dates do but this one was because Chastity couldn't remember what Carl looked like at all. Luckily for her, Carl more than made u...