Sissygasm Stories

121 results
Orientation
Length
Source
Infinite Scroll

Strawberry Milk Pt. 04

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Once I figured out how I wanted to experiment with this revelation on my nanos I decided on Dr. Corey as the start and Jill my porn store sissy. Dr. Corey was fucking me everytime I seen him and I started trying to concentrate as he breastfed from my huge titties. Not out loud but like mentally to my nanos. ~Harder, a harder bigger cock...more sperm, more...

Caught in the Act

by taodie on Oct 6, 2020
Transgender & Crossdressers

As you sit watching TV while your wife gets ready for a girls night out, you are not able to pay attention as you just feel your penis strain against the chastity cage. You had been looking forward to this night all week knowing you would have it to yourself. It was during these rare moments where you could fulfill your girly desires you had never dared shar...

Waking Holly

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It's been about a month since I told Holt, Holly the truth and moved her into my house. I never expected the side effects of what I did to her to be her to be her becoming a whole other person. I know it sounded like that's the point but the point is that you changed them, bent them, broke them and made them worse. And I fucking hated Holt, I really fuckin...

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...

Not So Adverse Reaction Ch. 03

by ElliottEden on Aug 29, 2017
Fetish

Authors note. Chapter three is a continuation of the previous two chapters, just in case you have just started reading. Things are going to get progressively kinkier in Betty and Elliot's life, with that in mind please read the tags associated with this story. I hope you enjoy the ride. "...sex addiction is also progressive. It often starts with a relativel...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

The Interview; Number 01

by Louise69 on Sep 14, 2017
Transsexuals & Crossdressers

Welcome! Many thanks for reading my short story, The 1st Interview! I'm going to let you decide the outcome of this and the 2nd Interview, so please email me and let me know who you would like to work at L/J's! The winner will be revealed in "L/J's", a short story to be released later this year. If you have any other ideas you'd like me to explore, feel...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...