Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

A Very Hard Working Girl

by keptsissy on Sep 12, 2017
Transsexuals & Crossdressers

I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things I've done and continue to do. And I love to think back and r...

Fine Tuning

by cathynylons on Jun 19, 2018
Transsexuals & Crossdressers

As I served my wife Dominique a brandy in the living room, I noticed that she was looking me up and down with her famous wicked smile. After finishing washing the dinner dishes I returned to the living room to see if she desired another glass of brandy. Again, I noticed her looking me over. I worried that perhaps there was a run in my nylons or that my masca...

My Stud's Special Secret

by MidnightWriter on Sep 19, 2017
Loving Wives

My name is Nikki and I think I've got a different take on this cuckold thing so many of you guys seem so nuts about these days. I'm 28, a former stripper who found the hung stud she'd always dreamed of about a year ago in the form of my boyfriend Drake. He was older than me, though I honestly didn't know how much at first, just that he was in his late 30s o...

A Sissy Surprise

by nancyallen on Sep 16, 2017
Transsexuals & Crossdressers

I got home early from my night out with the girls. Jeff wasn't in the living room watching tv so I figured he was in the bedroom jerking off so he wouldn't have to bother me with a request for sex when I was toasted. I decided to surprise him and slowly made my way up the stairs. I walked into the bedroom and stopped dead in my tracks. My boyfriend was on...

Did that Really Just Happen?

by AnnaV on Dec 2, 2019
Transgender & Crossdressers

I'd been out with one of my best friends. We'd had a few drinks and ended up in this little bar with some cracking looking women. There was one woman in particular who we both fancied. She was very pretty, but not especially my type as she barely had any tits. Nice enough and eventually she went off with my mate, leaving me alone in the bar. It was too earl...

Jezebel's Magic: Becoming Josephina

by twiddershins on Aug 31, 2017
Fetish

Jeff was just a regular dude when he met Jezebel. They had lived together for a few months and at first they seemed satisfied with each other. They got along fine and would have appeared like any normal couple in public, but that was now long ago. Even then, Jeff had felt lucky to have her because of his tiny penis! One Saturday night, Jezebel came home lat...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Sissified by My Sister Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Well about a week past, and my sister continued to come into my room to bury that hard strap-on into my ass. It started to become routine. Actually I was just thinking it was starting to hurt less when Olivia came up to me in private, and said "Ohh, my pretty little Dee-bear, my boyfriend is coming up for the end of winter break, just letting you know~" And...

The Man That Owns Me Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

Unlike many of the other men I saw, let visit me and have their way with me, he was not to the cum-and-run type. Most men are. He was different than all the rest. Most of the men I met online and allowed to visit me at my house were all hot and bothered in the chat rooms, hot to be with a sissy boy that was all femmed up and girly girl. But as soon as they w...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...