Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

Clove and Spice

by xaitonnar22 on Sep 19, 2017
BDSM

I glanced away from my video game for a second to pick up my cellphone when it started to ring. I looked at the screen only long enough to notice that it was my best friend Lars Wilton calling. "Hey," I said simple, propping the phone up between my cheek and shoulder. I took a moment to wipe the sweat from my palms before picking the controller up and turni...

Identity Crisis 09

by BabyDreamer on Sep 15, 2017
Transsexuals & Crossdressers

Next morning, Sarah woke up earlier than I did. She put on a slip and woke me up. I was still wearing her panties. My lower body was still sore from last night's ejaculation. Although I did not have any wet dream the previous night, my pad was soaked with urine. Last night, in the middle of the night, I wanted to go to washroom, but Sarah was hugging me so...

A Lesson From His Boss

by clarf on Sep 14, 2017
Fetish

Kate and Shawn had what they considered to be a perfect relationship. He was 30 and she was 26. They were good-looking, healthy and well-educated. Shawn had travelled the world building a successful and lucrative career, while Kate's natural beauty and elegant dress sense made her the perfect executive's partner. They had already decided they would get engag...

How Nathan became Natalie Ch. 05

by saintlycd on Jan 10, 2018
Transsexuals & Crossdressers

My senior year of college was very uneventful and basically the same as my junior year minus having Kevin fucking me. My dorm mate was a nerdy, engineering major and very intelligent with a very high IQ, but no social skills what so ever. I suspected he was more of a virgin with girls than I was. I often thought it would be sexy to dress as Natalie one day a...

Ron's Journal 03A

by Hypoxia on Sep 13, 2017
Novels and Novellas

Author's note: My uncle Ron died recently. While sifting through his files, I found journal folders marked MY STORY, writings about his life. I have edited these accounts and will post them when I can. These stories include bisexuality, incest, interracial and mature and group sex, etc. All sexual activity depicted here involves persons at least 18 years old...

T-Girl Fantasy Island Pt. 05

by skywriter62 on Aug 29, 2017
Transsexuals & Crossdressers

I hope everyone had a wonderful Christmas. Mine was ok. Yasmin Lee and a sexy Jessy Dubai were not under the tree waiting for me but a guy has to dream, right? lol. Happy Holidays to you all! Steve was not so fortunate in duty assignments on the night before the hunt. This time he was required to bring out food which was much more demanding as he was re...

Trisha's Transformation

by Stormbringer on Sep 18, 2017
Interracial Love

Author's Note: This story stands alone, but contains characters from another story of mine, "The Fiance And The Fitness Instructor". Inspiration for this story came from another called "Kimmie's Conversion" by Loadjunkie. "All you have to do is wear this every night for a month," said Dr Conger. Trisha reached out and took the device. It was pretty simple,...

Long Lost Bffs

by generalrubbie on Sep 16, 2017
Transsexuals & Crossdressers

Kara moaned quietly. Finally, she was having some reaction. We had been going for nearly an hour now, and I was worried that she just wasn't feeling it. Sitting on top of me as I thrust into her, she shivered as the orgasm washed over her body. I looked over her as I watched her large breasts swing with the motion. Her D-cups were pale and now covered in goo...

Lessons Learned

by MsCM on Sep 16, 2017
BDSM

In the way of a warning: There is no category for 'bisexual' here, so I hope the tags help. Although this piece starts with a cross-dressing sissy/femdom scene, a lot of the later parts of the story is MMM, with the female character only turning up at the very end. It's not *forced* bi either. ***** The woman next to him at the bar lit a cigarette, a long,...

Black Man One Ch. 24

by Weak_White_Wimp on Sep 19, 2017
Interracial Love

The next morning would not provide any consolation to the total defeat and humiliation I experienced just the night before. It was 9:20 a.m. when I was awakened by the subtle sounds of "clattering" dishes coming from the kitchen area. I sat up from my sleeping position on the sofa and held my head, which was suddenly throbbing in pain. I looked towards the...