Brother Sissy Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Blackbone Crossing

by DonSwami on Dec 4, 2020
Fantasy

AUTHORS NOTE: This story is still a work in progress, I’ve got a lot of idea’s on where I want to take it and what different chapters are going to be. I decided to publish Blackbone Crossing because I really wanted some feedback/ideas. The story is open to other writers, so feel free to submit your addition! Some chapters I’m still working on and I haven’t p...

Open in Reader

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Trouble in Paradise

by Buildaworld on Sep 12, 2017
Transsexuals & Crossdressers

Spring time in the city had gotten tough. People had to be tighter with money and as such, the café was dead that afternoon. The only customer we had was Gladys, the kind old cat lady that loves to show off pictures of her white Persian cat called Yasmin. I was minding the counter, flicking a wooden stirrer between my fingers when my world brightened with t...

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

My First Time as Sara... Pt. 04

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I love being Sara and everything it has awakened in me. In the months since I have been with Steve and becoming Sara, I have slowly shredded away my old self like a snake looses its skin. The only time I even dress up as John is when I'm at work. Even then, I have a little bit of Sara with me by either wearing panties and sometimes pantyhose under my khaki p...

The Molly Virus Ch. 05

by Sissyhalo on Mar 12, 2018
Transsexuals & Crossdressers

*Before... I kiss him leaning down and shoving his legs up with me as I fold him in half and fuck him over and over as we kiss then it happens. There's this inside resistance that stops as the brain and body reconciles getting fucked and relaxes and lets it happen. There's this sweet sigh of surrender that comes out as I bottom out inside of him and then h...

My Phantom Lover

by DianeTG on Aug 21, 2018
Transsexuals & Crossdressers

Growing up, one of the things I hated was having to share a bedroom with my brother. Sharing with any brother would have sucked, but my brother was - well, I think the polite word is - an asshole. But I will admit that he was an asshole who was good at handyman stuff. So when our dad gave him permission to fix up an old shed we had at the back of our yard as...

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...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....