Sissy Pills Stories

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Orientation
Length
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Infinite Scroll

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

A Mistress to Obey Ch. 04

by gbr2004 on Sep 12, 2017
BDSM

This story includes female domination, forced fem, forced bi and discipline. Not your thing, please find a different story. I follow Mistress into the playroom wearing just the thigh high nylons and heels. I'm so hoping she is in a good mood after watching her have several orgasms with Terrell. Maybe she will be in a more playful mood, hopefully, thinki...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

First Time Cross Dressing

by fethishboy on May 1, 2003
Fetish

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved t...

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The Pool Party

by JamesMiehoff on Nov 19, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Unleashed

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Ray stood up from the chair in the New Millennium African Braiding salon and checked his fresh cornrows in the lengthy wall mirror. He folded off three twenty dollar bills and told the attractive dark-skinned stylist from Ghana to keep the change. She had attempted on occasion to get the six-foot-four-inch, two hundred forty pound brother to get inside her p...

Briefs No. 03: My Wife's Friends

by PatriciaFCartier on Jul 15, 2019
Transgender & Crossdressers

While sliding my silk stockings up my newly shaved legs, I thought about what got me here. My wife, Madison, told me after I'd been transformed that she'd planned this since before we married. She said she'd dated a boi in college for a while until the boi had been stolen from her by one of their professors. Said she'd liked the concept, if not the result. S...

Revenge?

by magmaman on Sep 15, 2017
Loving Wives

When a young man is barely 19 years old, hormones rage. It's just the way of life. Ricky was that way, having discovered the joys of sex just a few days earlier. He decided he really did like that. That one time had been in his old Chevy Camaro and it was not all that easy to do. The beach party earlier had been a kick, Ricky spent most of the evening dan...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

Sissy Wants Her Wife's Boyfriend Ch. 03

by SissyArlene on Oct 31, 2018
Transgender & Crossdressers

I was elated as I entered the hall bathroom to freshen up. Cindy, my wife, had just invited me to sleep in the master bedroom. It would be the first time since Ty, her boyfriend, took my place in our marital bed. I didn't know what was about to happen, but I knew that I intended to take advantage of the situation. I figured I was either going to have "lesb...