Sissy Brother Stories

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A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Kyle, The Party Dog

by Mixedwritings1993 on Sep 17, 2017
BDSM

After calling his little brother by his name, Brandon got a little pissed off when no one responded, "Damn, that boy is sleeping once again, man, can't he even stay awake for few hours at a stress?" He stomped on the floor hard on entering his little brother's room and was amazed to see even the loud stomping noise didn't wake up his brother, Kyle. Brandon...

Alex to Alexis Ch. 01

by TransPrincessMorgan on Sep 25, 2017
Transsexuals & Crossdressers

Thanks to Jack Murphy for being our volunteer editor! Enjoy! ***** Chapter 1: Feminization Alex was late home again. Once, maybe twice would have been acceptable, but this was the third time this month. His mother, Daniella didn't know what to do with him, especially considering her other children, the eldest, Hannah, who was 25, and the youngest, Amelia,...

Jenny Plays with the Big Girls Ch. 05

by Johnboy9 on Sep 12, 2017
Transsexuals & Crossdressers

Well, that was one fine mess we got our Jenny out of that last story, wasn't it? Whew! This story is a lot calmer and yet a promise of more to come. I again want to thank all supporters and interested ones who have urged me to continue this tale of our Jenny to see what will happen to her in the end of her journey through this unfortunate (?) web in which sh...

A Handy Surprise Ch. 03

by SissyTrixy on Apr 4, 2018
Transsexuals & Crossdressers

There's a kind of surprise when you're completely frozen, like a deer in headlights. There stood my sister wearing a pair of jeans with a white t-shirt and a black hoodie. She had luggage beside her and looked utterly shocked with hot white anger flooding her face. There I was bent over on the couch, wearing nothing but a white laced bra, a pearl necklace a...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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Ash's New Career Pt. 02

by Fibaro on Sep 28, 2020
Transgender & Crossdressers

Standing back in the doorway of her own room Keira was surprised to see the wonderful job Ash had done with his makeup. It looked nearly as good as her own best effort despite the colours she had given him. She smiled watching how Ash applied the last touches to his makeup look before coughing loudly just when he was putting the brush down. Ash who had bee...

Ladybug corruption

by fnuriia90 on Apr 22, 2025

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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Merry ChristmASS, Bitch Boy!

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

The holidays were upon us. I had spent the last three months of my life as the personal sex slave of Brittany Andrews and Chantz Fortune. By now I was used to the chores, and the beatings, and constantly servicing and being fucked by their various strapon dildos. However, I never got used to the humiliating situations that they placed me in on a daily basis....

Sister Mistress Ch. 15

by LilLindaMelons on Sep 19, 2017
Transsexuals & Crossdressers

Pulling back Kathy patted Jenny's still sore cheeks. "Catch ya later girlfriend." "MMMMM bye, you know I'm going to dream about you Mistress Katherine." "I hope so Baby." After watching Jenny disappear through the garage Kathy walked up the service steps and into her bedroom. She was eager to checkout the surveillance of her mothers' bedroom. Deborah ha...