Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Twice as Nice

by puzziboi on Mar 17, 2020
Transgender & Crossdressers

About ten Christmases ago, Lemar McCants had been shopping for gifts with his early tween daughter. On the list was his wife, his parents, and one of the middle school aged girl's classmates. He remembered the conversation. "Dad," Maryam beamed as she selected what appeared to be a tiny white rag doll with pink hair and a pink cat in the same box. "This is...

The Path to Happiness Pt. 04

by brendachaplin2000 on Oct 8, 2019
Transgender & Crossdressers

After couple of days I had settled in to Roger's spare room. I cleaned and cooked for my room and board, not that I was a great cook, but I could warm up food without burning it. I was living full time as Brenda now. My last outing as Brian came when I went to my Store job and quit. I had only worked there a few weeks but the manager wished me well when I t...

The Collaring of Chloe Ch. 21

by MemoryofSnow on Feb 10, 2020
Novels and Novellas

The Collaring of Chloe Chapter 21 - Wise Sissies and Quilt Burritos **Characters and text are protected under copyright law "Oh fuck, oh fuck, oh fuck!" Mittens wailed, her voice pitching higher with each repeat, approaching the point of a shrill shriek. Her back was arched so heavily that her torso had lifted up from the sofa, pawed hands clutching the s...

Finding Claire

by Sissyhalo on Nov 26, 2017
Transsexuals & Crossdressers

*Before... I get cleaned up and instead a drink I have a big mug of coffee and a long, long shower. Thinking on all of it a lot. Then I check my bank accounts twice online. I go outside after slipping into sweats and walk around my house and the yard and the garage, the big barn one out back. It's my second house here actually with Roxanne getting the f...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Sissy's sister

by acepmn on Nov 21, 2015
Bisexual

Anna had always seemed like a good girl. Our parents weren't suspecting anything bad about her, just like they didn't suspect I was spending a lot of nights dressed as a girl in my room. I had skirts, cute tops, slutty dresses, panties and sexy thongs, butt plugs, dildos, cockrings, vibrators... A whole panel of varied toys to play with while dressing up. I...

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Subliminal Obsessions

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Finding a place in the city is rough sometimes for a good place honestly and I spent two years in a real shitty studio apartment with not even a laundry room in the building and just no room or increasingly no room. And my luck turned around after I won money. Seriously there's a 50-50 draw at work and just sort of on a whim I put my name in and I won. Not...

High School Dilemma Ch. 01

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

I should have known better. It was such a stupid thing and it didn't even work out. Here I was graduating from High School. I had just turned eighteen and it was the last week of school. How could I have done it? Why did I take the chance? Kelly was probably the prettiest girl in school. Her hair was long and blond. Not much different then mine. Actually we...

Backdoor Man - The Missing Chapter

by SevMax2 on Jul 14, 2020
Group Sex

Having settled the matter of who owns whom by everyone agreeing that I owned them all, I was very much engaged in what turned into the Orgy To End All Orgies, or so it seemed that evening, as we fucked our way far enough into the evening that by the time that we were all hungry, we didn't have time to cook. It was partly the fault of those blue pills, which...

Siss the Bride

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

I was nervous. I mean, of course I was, how could I not be? Everyone is nervous on their wedding day, it's a big day, a commitment, especially when you're 26. I mean, it's not like I'm afraid of commitment, many of my boyfriends in the past would be able to tell you that; I wasn't exactly the type of person who would be reserved when it came to going all out...