Sissy Prince Stories

14,095 results
Orientation
Length
Source
Infinite Scroll

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

Holly's New Start

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

I love Jamie so much it hurts. I mean there's a lot of things that would have people freaking out over this relationship of ours especially how I am and how we started. Jamie loves me despite my past. And like he really, really only has a sort of little picture of just how bad I was as Holt. Only he found reasons why Holt ended up so broken. No, no excu...

Uurf Ch. 05A

by Beatnic_jazzman on Sep 16, 2017
Sci-Fi & Fantasy

We had breakfast with them, an assortment of dried fruit and honeyed seeds, compacted into a bar. And more of the cookies from the barrel, one for now and one for later. We said goodbye to the girls, and Davina, she gave Martin a long lingering kiss as they parted Alice turned and beamed at me as we left, a radiant toothy smile. Like the duchess's cat, on...

AliExpress and Sissy Downfall Pt. 03

by His_fag_wife on Nov 2, 2017
Transsexuals & Crossdressers

Tim cupped Emma's arse cheek as they went into the hotel room, stroking her, sliding into the cleft of her cheeks, warming her up a little more, not that she needed it. Charlie didn't notice them come in at all. Not that she could really turn her head with the thick COCKWHORE collar padlocked tightly around her neck. The cords attached to the dildo were als...

Cinderella - a BDSM Retelling

by MistressMoira on Sep 25, 2017
BDSM

Once upon a time there lived a kinky girl, a very kinky girl indeed, named, well never mind her real name, her chosen nick for play was "Cinderella", for reasons which will become apparent later. Cinderella lived in a polyamorous family with an assortment of bdsm proclivities with her "Daddy" (a switch - top to Cinderella and bottom to his Domme to whom he...

Letter From Montgomery County

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom, Loving your "Taped Confessions" series. I am known as the Bitch of Bethesda, for I've really trained a lot of hopeful couples in the femdom life, all over Maryland, D.C. and Northern Virginia. Enjoy! Rhyce, torturer of Chevy Chase Crybabies... "So how goes it with Milton? Did you up the ante like you said you would?" "Jesus, Vermillion,...

Husband, Drop to Thy Knees! Immediately! Ch. 01

by Ashesh9 on Mar 7, 2018
BDSM

"Husband drop to thy knees!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!! The vast assemblage watched the spectacle appreciatively: male phalli th...

Jock Princess Ch. 02

by Sissyhalo on Sep 15, 2017
Transsexuals & Crossdressers

My brain trembled with my body. I could feel it, my insides all those nooks, crannies, all those muscles inside me trembling inside from being fucked so hard and so deep. All mirroring my brain and the shock of getting fucked too and how much I loved it. And I did love it, more than I should, more than any jock guy ever should. If there was a part of me t...

Knight's Conquest Ch. 2

by evilernie on Sep 18, 2017
Sci-Fi & Fantasy

[Note: First, give me the chance to thank you for reading the first Chapter. I specially appreciated the nice feedback I got. This chapter is not a continuation of the first. I know people are aching to know what will happen to our hero. Well, I am afraid to that you probably have to wait months before we get to that. I am planning to narrate the events le...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...