Sissy Pills Stories

15,811 results
Orientation
Length
Source
Infinite Scroll

The School Slut Ch. 02

by cherrybubblebutt on Sep 12, 2017
Transsexuals & Crossdressers

Me and George continued to meet up, as well as Tristen but he started to stop texting me or calling me. When I asked George he would just say, "Oh don't worry your pretty little head..." Eventually he told me, we meet down this small alleyway in his car, Tristen took a one time payment for me, to George... George had BOUGHT me from Tristen! That dick! Geo...

He Looks Like His Father

by RainStevens on Sep 13, 2017
Interracial Love

WARNING! This fictional story isn't for everyone. It involves cuckolds, male feminization, submission, interracial sex and breeding. If you're not interested, go find another story. * I am a white fifty something year old married cuckold and a proud member of the W.B.A. My wife is twenty years younger than I and we have four children (with one on the way),...

The Road Trip

by JamesMiehoff on Sep 12, 2018
Erotic Couplings

Copyright (c) 2017 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 This work may not be published whether for fee or free without this copyright.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...

Sister Mistress Ch. 15

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Pulling back Kathy patted Jenny's still sore cheeks. "Catch ya later girlfriend." "MMMMM bye, you know I'm going to dream about you Mistress Katherine." "I hope so Baby." After watching Jenny disappear through the garage Kathy walked up the service steps and into her bedroom. She was eager to checkout the surveillance of her mothers' bedroom. Deborah ha...

Two Men in a Boat

by CarrieQ on Feb 7, 2018
Transsexuals & Crossdressers

After work, I liked to walk home along the riverbank. Working in a club, it was always dark when I finished, even in high summer. And because very few people used the towpath at night, I felt safe walking home in my waitressing outfit. It was a skimpy outfit. The club was a gay bar on the outskirts of town, and I lived on a small estate nearby. I liked livi...

Abducted and Turned Out Ch. 05

by dawnib66 on Sep 19, 2017
Transsexuals & Crossdressers

.... I lapped at her pussy as she intermittently moaned and derided me. "Eat that cunt, you sissy whore. I know you prefer cock, don't you? Answer me slut!" she said as she forced my face deeper into her pussy. "Yes, mistress," I said into her cunt. As I did, she moaned loudly and her pussy spasmed as she gushed into my face. "You are a good little bitch,...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

Sissy's Revenge

by Not_John on Sep 12, 2017
Transsexuals & Crossdressers

Ok, My last post received quite a bit of negative responses because my protagonist was a total wimp and let his wife walk all over him. Well in this one, in the end, stands up for himself. Warning: this story contains all the elements of cuckolding save one and feminization of males. If you have a problem with either of those, then quit reading here. Skip...

Unexpected Mistress Ch. 03

by Scottt on Nov 16, 2020
Fetish

Paul is pushed to his limits in this installment. Deborah accepts her role as Mistress, and is empowered by it. I hope you all enjoy chapter three...I had a lot of fun writing it. I awoke early, and showered and shaved. Debs white bikini was scattered about in our bedroom, and I put it on. I fixed her breakfast, and at seven o'clock started her massage. Deb...