Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

Panty Fantasy-Hurricane Kate Ch. 01

by eliasrotica3 on Sep 14, 2017
Fetish

'A day like any other,' thought Kyle to himself. The view outside his Research Triangle Park office was a little boring with the leaves all fallen and the snow not yet come. It felt good anyway to see the world and the weather. Kept him from getting office fatigue. He liked his job as a senior accountant but he did get a little bored by the routine at times...

The Millers Ch. 04

by CiaraSwallows on Sep 15, 2017
BDSM

It's been forever since I had a weekend off from the restaurant but I was happy to have it so I was really looking forward to my free time. Unfortunately, when you are in a contract which you have signed your freedom away for six months you don't really have free time. I was reminded of this when I walked in the door Thursday night and saw my bag packed wait...

Mama Mia Pt. 01

by grizzley123 on Jul 13, 2020
Fetish

This story is a fetish fantasy where many themes get woven together. There are cuckold, incest, bi-sexual, BDSM, and a few other themes all combined. If these themes are not your thing, please just move on. If they are, enjoy! Like most of my stories it arose from a single incident. In this case it was watching a very hot mom and her even hotter daughter mo...

My Cuckold Wedding

by CuckinChastity on Sep 16, 2017
Fetish

Note - this is a piece of fiction. The characters are not real. The scenario is purely a fantasy and does not describe any actual relationship. Laurel is not my actual wife. Enjoy! ***** I stood at the altar alone with Rev. Carl, the minister, looking out at the wedding guests. It wasn't a large wedding, still to me it seemed there were a lot of people l...

Cable Guy

by Girochen on Dec 10, 2017
Erotic Couplings

Sometimes I write little snippets, sometimes they are longer. Like snapshots of life, they occur to me and I must capture them. This is one that I wanted to share because I like it. It has some weird in it, man on trans man-girl, and some regular sex. But the real story is in between like a waffle holds the butter and syrup but isn't anything without the act...

The Descending of Jessica Ch. 15

by Jessie92 on Sep 19, 2017
Novels and Novellas

This was supposed to be a three or four chapter story, but I suck at estimating how long a story is going to be. It was supposed to be a one part epilogue as well, but again, I suck. Finally, I promised we would be up to Valentines Day a couple epilogues back, but I am only up to Wednesday of the same week. Again, I suck. I don't know how long its going to b...

Snowbunnies

by tori_tgirl on Oct 12, 2017
Transsexuals & Crossdressers

I was finding it hard to concentrate on my picture... the creaking sounds from the box spring grew louder with each passing moment, making it harder and harder to keep my crayons inside the lines. I didn't have long to finish my coloring, maybe another minute or two but it was already the prettiest unicorn I'd colored yet, and surely they'd be happy. I strug...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

Open in Reader

They're My Sister's Wicked Ways!

by grgy56 on Sep 18, 2017
Transsexuals & Crossdressers

Thanks for all the great comments. I know this third chapter has been a really long time in cumming but I hope you enjoy this one as much as the others. ***** So the first time I was caught by my sister, I was dressed in some of her sexy lingerie. That was bad enough but she also caught my best, bum buddy (literally) Chris fucking me and cumming in my ass...

A Somali Dominatrix In Canada

by Samuelx on Sep 16, 2017
Group Sex

The things that turn me on are simply that, the things that turn me on. My name is Farah Suleiman, and I'm a Somali woman living in the City of Ottawa, province of Ontario. I was born in the town of Mogadishu, Capital of Somalia, and moved to the Confederation of Canada fifteen years ago with my parents, Mohammed and Amina Suleiman. I am twenty two years old...