Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

Neighbourhood Terror to Sissy Pt. 20

by Fibaro on May 11, 2020
Transgender & Crossdressers

Chapter 22 Marcy woke up with a loud groan. Sleep had not come easy last night with how horny she had been, the fact that her butt had remained filled up, her sore throat and that chastity cage that seemed to hurt a lot more than it used to. On top of the difficulties falling asleep she was now woken up way too early. She had to since she was supposed to st...

The Wonderful Adventures of Miss K Ch. 4

by BrettLynn on Sep 13, 2017
Transsexuals & Crossdressers

This is yet another installment of the pure pornography that I love to call "The Wonderful Adventures of Miss K." So far, people have been loving my over the top sex romps, and I hope you fair fans love this one too. If you are not legally permitted to read this work in your legal jurisdiction, please do not read this. Also, I retain all commercial and non-e...

County Girl Ch. 01

by LaurenWestley on Aug 31, 2017
Fetish

So, here I was, waiting in the back corner of the garage, the door to the empty bay open. The night light illuminating the front reaches of the garage. The garage lights were off. Instead, in the shadow of the corner, I waited for him to come. Nearly a year ago I had met Master Cock on-line. This was a unique chat room, one where submissive wannabe transves...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Happy Endings

by desireethtttv on Sep 14, 2017
Transsexuals & Crossdressers

As I sat in Julie's bedroom, my high school's self appointed sleazy easy slut, whom I'd so long held discreetly in my deviant mind as an idol and often dreamed of having the same reputation; she appeared dumbfounded as if her brain were stuffed with cock. Innocence was always in her mind while with me. Her thoughts of me were nothing more than a boy who like...

Little Larry Ch. 02

by pantywriter on Oct 9, 2018
Transgender & Crossdressers Stories

The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Mon...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Sicily's Lesbian Son Pt. 02

by SubtleDeviance on Jan 29, 2020
Transgender & Crossdressers

Story contains themes of crossdressing, feminization, incest, and anal play Dante awoke with a little tent in his white lace panties, excited about the day to come. He smiled to himself and stretched across the clean white sheets, wearing one of the babydolls his mother bought for him, sheer, white and sexy. His bed had been the only place he could safely...

Helping Jess Pt. 03

by mski on Sep 18, 2017
BDSM

Sometime in the morning I woke up with Jess on top of me giving me a good morning kiss. 'Wakey wakey sleepy head!' she said with a huge smile. I grinned back, it was a nice way to be woken and she looked as gorgeous as ever in her red silk chemise. I started to get aroused but my penis was always going to lose the fight against the chastity belt. I grimac...

Master's Degree in Crossdressing Ch. 01

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

This series is the follow up 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 confessions to the public for the first time, my wife has generally been aware o...