Sissy Pee Stories

29,966 results
Orientation
Length
Source
Infinite Scroll

Janie Helps a Little Old Man

by sywwu on Sep 14, 2017
Mature

It had been years since he had been intimate with a woman and now, this woman, practically a complete stranger, was leading him out to her car in the bookstore parking lot. They had been chatting for nearly three hours over coffee and discussed a broad range of subjects. Eventually the subject of sex surfaced. That started them on this wild afternoon ride....

Hyperactive Testes Disorder Pt. 08

by sthsth on May 21, 2019
Exhibitionist & Voyeur

This is a continuation of this series, if you don't read at least part 1, you probably won't understand the setting very well. When Mike awoke a second time, Fifi was gone and Stephanie was still mostly covered in cum sleeping on the floor beside him. He felt a little from napping on the floor, and when he reached up to rub his neck, he realized that he had...

Twink Gets First Time Taste of Cum

by Alluring_Crimson_Shifter on May 22, 2019
Anal

John came to visit Alicia to ask for a date. He was wearing a nice shirt and tight pants. The conversation however seemed to avoid the topic of dating. She seemed busy and distracted from him. This late in the evening he began to change his plans to get a six pack of beer and maybe try again another time. He noticed her brother Victor, a blond long haired te...

My Devious Plan

by flashgordon562006 on Jun 3, 2019
Erotic Couplings

This story is the finality of a plan that was put in motion two years ago. The results couldn't be more perfect. Let me explain before I begin the story. Background My wife decided to stop having sex a few years ago for whatever reason. Her decision led me to find it someplace else. My name is John and I was 50 at the time. My wife was 49 and her name i...

Dan The New Girl Ch. 02

by janetjoneslovesyou on Feb 7, 2018
Transsexuals & Crossdressers

"OK, Dani, take off my knickers, choose a fresh pair from the drawer, and let's get you dressed," said Lucy. Dan sat up in bed. He was wearing a tight fitting white bra and Lucy's knickers - the ones he had pulled down Lucy's legs before he had plunged his throbbing cock into her wet and inviting cunt. The night before. When he had been a boy. Now everythi...

Sexy Mandy Busts a Young Black Nut

by BAD BOY BILL on Dec 31, 2017
Fetish

"Nigga check that fucken ride that just pulled in." the black teenager laughed elbowing his friend, his shorts damn near around his knees. "Be a sweet set of wheels to jack." agreed his equally youthful teenage friend checking out the ruby red Mercedes AMG GT Coupe. "That nigga gotta be 200 grand easy." "Fuck the car, check out the bitch driving it!" the f...

Roweena's Super Poop!

by Bizarre_Consent on Jan 6, 2018
Fetish

I'm not sure why Emily asked me to write this story down. It's just a funny, gross thing that happened to us a couple weeks back. My name's Roweena. I'm a college student in my mid-20s, a little older than most of my classmates. I can't afford the student housing, so I live at home and commute to campus every day. My best friend Emily lives at home, too. S...

The Diaper Spa Pt. 04

by clazzjoud on Feb 13, 2018
Fetish

Angela Rivers has worked her first full day at Padded Bliss and just heard someone call her name Angela turned around and saw her friend Catherine, carrying two unopened packs of Bambino Bellissimos. She had been trying to get in touch with her for the past couple weeks, but with no luck. She wanted to tell Catherine about her new job in person, but every t...

When His Sister Cums Ch. 01

by bnaylor987 on Mar 25, 2019
Romance

"Hey, Shannon and her roommate are coming down this weekend, and I need a wingman. I want to fuck Amber, and I can't do that with my sister around. You need to keep her busy," Scott told his roommate Jason. The last weekend in April on campus was epic, known across the country for its party weekend. "Maybe I want Amber, and you can have Shannon. You guys a...

Magic Dress - Yvette Pt. 09

by SlightlyRude on Mar 26, 2019
Transgender & Crossdressers

THE WISH I got my wish, but not how I expected it. It had been my dearest wish that Kathy could find a new man to love, so that I could become Yvette all the time. It happened but in a totally unexpected way. It was about a year after our arrangement where I slept with Cedric on Friday nights and Cora stayed over at our place with Kathy. Naturally they be...