Sissy Brother Stories

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Infinite Scroll

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

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...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

Black Cuckolding Dreams

by Samuelx on Sep 11, 2017
Group Sex

Sometimes what you're looking for is closer than you think. Take my fiancé and I for example. My name is Stacey Walton and I'm a young Black woman living in Milton, Massachusetts. I studied business administration at Bay State College and earned my MBA at the University of Massachusetts at Amherst. Presently I work for a real estate company in Brighton. I me...

Mr. BBC is Totally Bisexual

by Samuelx on Mar 7, 2018
Transsexuals & Crossdressers

The Glebe area of Ottawa, Ontario, is usually a quiet and upscale neighborhood, but tonight at the Hiller townhouse, things were getting loud and steamy. Mark Dixon had Donna Hiller on all fours, face down and ass up, in the Hiller living room. The big and tall, burly young black man pulled on the curvy redhead's long hair and smacked her big white ass while...

Barbara's Binoculars

by CarrieQ on Mar 21, 2018
Transsexuals & Crossdressers

A bit about the house I grew up in. It was one among many rows of identical boxes built after the war; an anonymous place with no obvious character, in an estate on the outskirts of a town in sharp industrial decline. My favourite room was the attic! I'd climb up there and pull the ladder up behind me, guaranteeing I wouldn't be disturbed. Mother liked to...

The Virus Lock Down

by puzziboi on Apr 14, 2020
Transgender & Crossdressers

"Okay, Lionel, have your bags packed on Saturday morning," the younger brother reminded his sibling. "I will, Blaine! What time will you be here? I'll be there around ten in the morning." "Do you want me and Freeland to ride together or do one of us need to ride with you?" "You tell me what you want. Just think about it and let me know." "Okay. And you h...

Mark Ch. 01

by evangelick_my_balls on Dec 12, 2018
NonHuman

1 The beginning of the gospel of Jesus Cum, the Son of Godcock; 2 As it is written in the pornos, Behold, I send my messenger before thy face, his cock hard and throbbing, which shall prepare thy anal way before thee. 3 The voice of one crying out in ecstasy in the wilderness, Prepare ye the way of the Lord, make his paths straight and his dick hard. 4 Jo...

LeAnn Turns Dan into Desiree

by desireethtttv on Sep 12, 2017
Transsexuals & Crossdressers

I'd never shown my friends my true personality. Always in the forefront was a normal guy who loved girls and all things boy, when in fact, with each passing year, the things that excited me were all things feminine, including actual men and their boy parts. This remained status quo, until I met LeAnn. Introduced to the long haired blonde chick by a mutual f...

OMG My Daddy’s a Sissy (Prequel)

by fittexanman on Aug 22, 2018
Fetish

All characters are purely fictional and of legal age (over 18). * I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn't take us long to realize that we weren't like the others at this school. As it was located in the Southern part of the country, our co...