Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

A Night For Romance

by maggie2002 on Sep 14, 2017
Romance

The night was beautiful as only spring nights can be when winter loosens its harsh hold and the soft winds blown and flowers grow. "Damn, I'm a poet and I didn't know it," laughed Sissy Littleton the Editor of the Littlestown News, as she sat at her computer trying to come up with a short story as filler for the Sunday Magazine. She had to be done by tomor...

Cuckold Story

by Grey Eagle 286 on Sep 19, 2017
Loving Wives

I watched my wife of ten years as she entered the den where I was working on a report for work. She was looking very good. Grace wore a light brown leather skirt with a pale yellow shell and Cardigan sweater set over brown boots with high stiletto heels. Her body is amazing, and is centerfold quality for playboy. I am very proud of her. I smiled at her, "Yo...

What Just Happened? Ch. 04

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 04 -- I am no longer in control I looked at Beth and so did the pizza guy. The delivery guy started a discussion by saying, I do not want to offend you girls, but you are both very attractive and I see one of you has panties on because I can see them. So the other panties on the floor must be yours he said as he looked at me. What is Beth doing st...

Black Sissy For White Mistress

by Samuelx on Sep 16, 2017
Interracial Love

Right now, I'm lying in my king-sized bed. And I'm getting fucked in the ass. Picture this, if you will. A big and tall young Black man of Haitian descent getting fucked by a tiny, blonde-haired white chick wearing a strap-on dildo. My name is Stephen and this is actually my idea of heaven. I live in the Vanier sector of the City of Ottawa, Province of Ontar...

Black Cop's Stress Relief

by puzziboi on Jan 20, 2020
Transgender & Crossdressers

"We think you're doing a hell of a job, Corporal," the bronze-skinned police lieutenant explained. "But at this time we're going in a different direction." "Alright. Thanks for letting me know, Lew," replied Christopher Patterson with a fake smile. "Is the candidate internal or external?" "External," the supervisor revealed. "Alright. I'm kinda tired," Cp...

Sissy Sidney and Sister

by FemFreak on Apr 17, 2019
Transgender & Crossdressers

Summary: Sidney is reluctantly persuaded into submitting to Ellen's humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity. All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest. ~~~~~ Angie loved to bully her little brother Si...

Dry Valley Ch. 11

by jushorny on Sep 12, 2017
Chain Stories

Mitch kissed his mom goodbye and drove off to his place to clean up, the oil change and fence repairs having covered his body dirt and sweat. On the way home he schemed ways to best to convince Jess to stay in Dry Valley. He knew it wouldn't be an easy, most likely taking the entire six day limit imposed on by Jess or possibly longer. Once home, he headed...

Jasmin wears the pants Ch. 02

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

In Part 1 of "Jasmin wears the pants" our hero is fascinated by a woman and in the end of the chapter he is waiting in front of her door just wearing his briefs. Thank you very much for all the positive feedback. I really appreciate the praise. Once again people who don't like TG stories and or are under aged shouldn't read on. All rights are reserved. If so...

Fukee Sukee Beach

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...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...