Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Goddess Monica's Beta Bitches h. 01

by DonGarciaWallaceIII on Sep 12, 2017
BDSM

Meeting Gustavo Monica Garza's austere, coprolite-like walls, covered with aquarelles of men in tutus and women's swimwear, are sound-proof, and Gustavo must intuit or presume this since, once inside, his voice climbs in pitch in a way it wouldn't in any other of her condo's rooms. In the little kitchen, for instance, he nearly whispered. The tutu- and wome...

Nikki Goes to College

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

When I was younger I used to be a complete bully. I used to make fun of the poor people that couldn't afford to buy new clothes every school year. There were also times that I would make fun of girls that didn't want to participate in gym class because they were wearing a dress. I used to agitate so many people that I would get into fights almost daily. One...

A Conversation with a Lady

by OpenMouth on Oct 15, 2017
Transsexuals & Crossdressers

This story was inspired by Gemsissy and her wonderful shopping trips... ***** A select lingerie shop in a small northern English market town. The shop front reads 'Cherie.' I walk in and I'm surrounded by wonderful things by Lejaby, Aubade, Lise Charmel. A stylish woman is behind the counter; she's mid-40s, slim, blonde, tall. She has tanned skin, expe...

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...

Country Girl: The Beginning

by LaurenWestley on Sep 16, 2017
Transsexuals & Crossdressers

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...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Wife in Control Ch. 05

by wifetoy on Sep 25, 2017
Fetish

Or maybe a dance fully dressed and made up for ballet. Stretched and rehearsed to dance any male pride away. This is the fifth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full poem and the humiliations I have been forced to e...

Neighbourhood Terror to Sissy Pt. 15

by Fibaro on Dec 23, 2019
Transgender & Crossdressers

Chapter 17 "If you don't mind watching over the sissies for a bit, I will go look around for the exact outfit I have in mind. I don't trust Stephanie to get it just right. You will be fine watching over the sissies, right? If not, you can always call out for me, but I am sure you are going to do great." Linda said to Lisa who was still getting her feet wors...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...