Sissy Brother Stories

49,708 results
Orientation
Length
Source
Infinite Scroll

The Farm Ch. 02

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

Trembling with fear I squat naked on the floor where the man who dragged me down the hall has dropped the lead attached to the collar about my neck. Starting with fright at his every sudden movement I watch him sort through piles of clothing sniffing back cum scented tears. Eventually he holds up a pair of girls panties that he inspects closely. With a sat...

My Girlfriend's Sissy Roommate

by SEVERUSMAX on Sep 15, 2017
Transsexuals & Crossdressers

"Look, Stan, there's ... there's something that I have to tell you and explain. It's not easy. In fact, it's very fucking weird, even to me, even while I've been letting it happen. I have to level with you, because, well, you and I have been flirting for a good while now and I'm smart enough to realize that you want me. Hell, I want you, too. This is very .....

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

Young Master Ch. 05

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was running through the mansion, being chased by something so horrifying that I didn't dare to turn around and see what it was. I tried to find my room, but the once familiar hallways were now disjointed and strange, as if the building had be rearranged and some pieces had been replaced with imitations that had a sinisterly artificial look to them. My purs...

Erika Blossoms Ch. 06

by SmoovB on Sep 13, 2017
BDSM

Note: This is chapter six of a very long story. 28 chapters so far. It is wide ranging and will eventually touch on interracial sex, dom women, lesbian sex, true love, revenge and much, much more. I hope you enjoy it. ***** CHAPTER SIX – Sunday Night I walked over to unlock the door. As soon as it unclicked, Jana was coming through. I held my finger to my...

Sarah Ch. 1

by Steve256 on Sep 16, 2017
Fetish

My sister and I had never had a calm relationship. She was my parents' favorite. Always pretty from an early age, she blossomed into a true beauty. By the time we reached high school (she's a year older than I), she was the most popular among the 'in' crowd. A champion cheerleader, with her classically beautiful face, long flowing brown hair, and perfect bod...

Demi-Monde Barber of Fleet Street

by skriblur on Sep 14, 2017
Transsexuals & Crossdressers

Episode Three: Mrs. Henderson & the Demi-Monde Barber of Fleet Street The story picks up from the end of "Mrs. Henderson Plays Matchmaker". A sissygurl and a tomboy are together on the couch, the sissygurl's face in the tomboy's lap. Or maybe it's the tomboy's face in the sissygurl's lap. It works either way. There's also a third and fourth little pretty;...

On the Beach Ch. 03

by Turbidus on Sep 25, 2017
Exhibitionist & Voyeur

The fallout from the previous night's festivities continues... Thanks to LarryInSeattle for his editing. Any errors that remain are my own. ***** I gave up on the idea of jerking off. Something was going on with Bill. I realized that this was the first time in my life I was worried about my brother. He'd never gotten in trouble. He had been about the l...

The Path to Happiness

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

Author's note, none of the characters are below the age of consent. *** Here I was staring into a full-length mirror, seeing myself glowing in my wedding dress. At 44 years old I never thought the day would come when I would be a blushing bride. As I stared my mind wonders back to my childhood. I was born a boy, Brian Cole. From an early age I knew I was d...