Sissy Blacked Stories

11,287 results
Orientation
Length
Source
Infinite Scroll

My Therapist's Chinese Doll

by naoko17 on Dec 18, 2018
Transgender & Crossdressers

Disclaimer: The content below has many degrading comments on certain race and sexual orientation, so please don't read it if you are looking for "political correctness". ***** I still re-lived the night Eunsun left me. I remember her blank stare, followed by a cold grin. She wasn't the lovely woman I once loved. She said she didn't love me anymore, and wa...

Life according to Lizzie

by Lizziewannabe43 on Sep 16, 2017
Transsexuals & Crossdressers

As a word of warning this is more of like a pilot to see how this story goes if it is liked and good feedback is given then I will right more. Everyone mention in this story is above 18 years old and are not based upon real life characters. Please any criticism is accepted and highly encouraged thank you for reading my little tale...enjoy. ***** Luke began...

Adult Trip Pt. 04

by cuckcpl4play on Jul 18, 2018
Interracial Love

Master released me from the tree and quickly positioned both hubby and me on our knees next to one another. He handed me a brief and simple contract and ordered me to read it aloud. Obediently I read the contract as demanded. "You have agreed to be Master's dirty married white whore for the remainder of Master's trip, subsequent trips to this hotel where...

Jane's Play Thing Pt. 02

by Stillherer on Sep 13, 2017
BDSM

"More dessert," she whispered seductively in my ear. I whimpered as her hand began to squeeze and pump my sex sensitive cock but didn't even think to stop her. After all that sex around and under the dining room table my poor cock felt like it was raw. Jane didn't appear overly concerned with my discomfort as she dragged me off the floor by my erection and...

Cassie Needs the Money Ch. 06

by interqueen on Sep 14, 2017
Interracial Love

"Oh thank you, thank you, thank you," Jane said, kneeling on Cassie's bed. In front of her stood four naked men, their cocks sprouting like tree trunks, hard as rock and just begging to be drained by the woman gleefully eyeing them. Cassie and Tom were off to the side of the room, the former with her hand in her underwear, touching herself. The latter had hi...

Becoming Mindy

by mindyrose on Sep 18, 2017
Transsexuals & Crossdressers

Hi. This is my story from an unsure, shy, awkward boy that was pretty feminine to a proud, confident and comfortable transgendered girl. If you're not into reading about transgendered people and their stories, as well as their sex lives, then please move on. I know I made some foolish decisions, but I am a completely healthy person today and those decisions,...

A Jamaican Vacation Ch. 02

by sissyashley4bbc on Nov 25, 2019
Transgender & Crossdressers

After the events of yesterday, I slept hard. I'm not exactly sure what time we fell asleep, but I woke up from a combination of the sun hitting our room and a hardening big black cock in my mouth. I can't believe I slept the whole night in lingerie with Big Daddy's cock resting in my mouth and my right hand clutched onto it like a stuffed animal. Instinc...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

Kitty Ch. 01

by ts_candi on Sep 15, 2017
Transsexuals & Crossdressers

Hi, my name is Kitty. I live in a small town in China, which is more like a large village, with my mistress - Madam Kia. I used to be a man, but I changed. The story of my change is complicated, but I will try to tell it as clearly as I can. I never lived in china, to start with. I was a happy man, all of 24 years old. I loved my women, and I had a fair sha...