Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Recruiting of a Sissy Maid Ch. 15

by Sissy_Chantel on Dec 22, 2017
Transsexuals & Crossdressers

Chapter Fifteen: Life Changes but Normalizes Monday morning, Carl and Chantel are up and at it, breakfast in the hotel restaurant and then a shopping excursion to an are Jewelry store for Carl to buy Chantel her engagement ring. Dressed sharply but casually Carl in a white button down shirt, Khakis and black walking shoes. Chantel a white turtle neck, black...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

The Adventures of Sissy Madison Ch. 01

by sissymadison on Mar 6, 2018
Transsexuals & Crossdressers

Kent slowly opened his eyes to let his eyes adjust to the bright light from the lamp. He slowly rolled over and stretched as he saw Kim sitting up thumbing through something on her phone in a white tank top and boyshorts. She looked at him and said "Good morning!" as her eyes shifted down to his chest. She stared at a lilac purple lace babydoll that had jus...

Danny's Education

by Greymead on Sep 19, 2017
Transsexuals & Crossdressers

"Damn it, Jem! I'm a doctor, not a sissy!" Jemima chuckled, recognizing my weak attempt at humor as I tried to avoid the question. She was still holding the brief, lavender panties out to me. "C'mon, honey. Just do it this once for me, please?" Her big eyes begged more eloquently than her voice, and, though I didn't care to let her know in case it made me...

Crystal: A Sissy Set Free Pt. 03

by InSpectrum on Sep 16, 2017
Transsexuals & Crossdressers

This is a direct continuation from Parts 1 and 2. You should probably read those first, if you haven't already. ***** Before he could think Ryan was gone, Crystal shut the toilet seat re-locked the door and sat down feeling a jolt from his plug, He suddenly felt very uncomfortable, his feet ached from dancing in ridiculous heels, his corset was way too ti...

Sissy Stretching for Princess T Pt. 02

by Subboi23 on May 12, 2020
Fetish

Once I get home, I practically run to my room. Sitting in the car has pressed my plug deep into my ass and now my running causes it to wiggle around while still deep inside me. "Home Princess," I text as soon as I close and lock the door to my room. I quickly peel all my clothes off except for my panties and get on my knees. My toy is retrieved from a draw...

Robin and Jimmy Olsen - Sissies Ch. 04

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

The Date Continues (finally) ***** Just as Ollie and John began to wonder what was keeping their dates, they spotted the delectable pair of sissies returning from the rest room. When they reached the table, both men stood. Their politeness was rewarded by a brief kisses from the pretty lads. Each girlyboy also managed to run her hands across the crotch of...

Pantsed

by grgy56 on Sep 14, 2017
Transsexuals & Crossdressers

"Hmmm! Not here." I was naked and looking for my sweats to wear around the house but obviously I forgotten where they were. They weren't in the wash basket or anywhere else I would have expected then to be. "What about the unexpected places?" I asked myself. "Lori is always taking my stuff." I started rifling through her dresser and came across a pair of d...

Paradiso Ch. 10

by SlyKink on Sep 19, 2017
Fetish

Day 3 Continued Sara and I arrived at the spa a half an hour after leaving our room. It was still early and there weren't many people out in public fucking just yet, even though it was shaping up to be a beautiful day. We stopped only once to watch a foursome consisting of two men and two women, none of whom wore anklets. One pair was going at it missionary...

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...