Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Such a Deal Ch. 05

by Angelscuck on Aug 31, 2017
Fetish

Once again I tried to take this monster cock in my mouth with no luck. "Well," Mark stated, "If she can't suck it, then she can fuck it!" He effortlessly spun me around and placed his glistening cock at the entrance to my anus, and said, "Ok sissy, ask Angel's permission and beg me to fuck you and it better sound sincere or you can count on getting those t...

From Her Ex-Boss to her Bitch Pt. 07

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. It had all st...

The Cage Pt. 04

by FiveDots on Sep 15, 2017
Transsexuals & Crossdressers

Thank you for reading this far. I tried to incorporate feedback I received into this chapter. Please enjoy, and don't forget to comment! ***** Masochism brings pleasure from where you may least expect it. Pain, humiliation, lack of power. A giantess takes that power away with her size. She may inflict pain and humiliate you. What could be more humiliating...

The Feminisation Initiative Ch. 02

by Slipperylock on Oct 30, 2018
Transgender & Crossdressers

The room was quiet and dark - the only illumination spilled from the Observation Room window over the eight beds and their occupants. The only sound in the room was the whirring of the machines, and the occasional muffled moan. In the Observation Room booth, the Director of the F-center fiddled with the control panel nervously and jogged her leg. The Presid...

The Wedding Ch. 01

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

(Intro) This is the continuation in the life of Dale Horn and the never ending saga of both his pleasure-- and his plight while living in this new world of sexuality and discovery brought about through the hands of his caring, supportive Mother and as well, his long lost love Patti... Where we left off -and with every ones encouragement our Dale saw himself...

Mistress Kate Pt. 02

by corduroysissy on Mar 7, 2018
Transsexuals & Crossdressers

When he arrived home from Regan O'Reilly's office Jordan was still in a daze. He needed a drink, no scratch that, he needed a bottle. In a matter of a couple hours he'd gone from having his life threatened, to getting a blowjob from the Leprechaun, to being ordered into sissy sexual servitude by Mistress Kate. She was actually expecting him to be her fucking...

Oh, Mr King! Pt. 05

by exaucer on Mar 6, 2018
Transsexuals & Crossdressers

At some stage during the night I became aware that Mr King was trying to push his fat cock back into me again. I was too weak to resist, not that I wanted too, and too far gone to fully participate, so I merely adjusted my position to facilitate his penetration. Since my pussy was still slick and sticky from his earlier deflowering, Mr King's cock eased into...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Cuckold CEO Ch. 09

by drdick69 on Oct 15, 2018
Fetish

Monday morning came as a blessing. The weekend turned out to be a sex charged fuck-fest that culminated with me eating James' cum from my wife's ass. All day at work, my mind returned to the events of the weekend. The domination, power and shear supremacy of James was astounding. He had total and absolute control of not only my wife, but of me also. I could...

Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...