Pegging Crossdressing Stories

2,183 results
Orientation
Length
Source
Infinite Scroll

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Bed and Breakfast Hotwife

by donaldelliott11 on Mar 9, 2020
Loving Wives

[Note: The hotwife in this story is, well, a wife, right? That means she has a husband. When she gets hot, he becomes a cuckold. You following this, Annony? Get over it, or read a different story. Oh, yeah, one more thing -- BTB is a fetish and has no place in Loving Wives.] *** Tracy and Don Elliott, empty-nesters in their late 40s, supplement their incom...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Mistaken Identity

by kcwilder69 on Mar 25, 2019
Erotic Couplings

It was my first week at the new job, and I was drained from learning new protocols and procedures. And how would I remember the names of all the people I'd met? I parked the SUV in the driveway, looking forward to a warm dinner and a quiet evening. Approaching the house, I see it's dark. Why isn't Laurie home? She's always home by this time. I open the door...

Grace Under Fire Star Does Blacks

by Samuelx on Sep 17, 2017
Celebrities & Fan Fiction

Brett Butler looked at herself in the mirror. At the age of fifty three, she still looked good. Blonde-haired, blue-eyed and curvy. Blessed with Irish good looks that simply refused to fade. Unlike her star in the upside down world of Hollywood. That one faded so damn fast she went from being a household name to a nobody in no time. It had been so long since...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

Black On Black Pegging: True Love

by Samuelx on Sep 11, 2017
Fetish

I don't know why he thought I wouldn't be able to handle it. I really hope he'll stop hiding stuff from me after this experience. Female on male strap-on domination, Afro-Caribbean style. Seriously. I honestly wish he told me about this really hot fetish of his sooner. My name is Malinda Lexington and I'm a short-haired, green-eyed and kind of chubby young B...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

Taming the Dom

by Ben Rosewood on May 31, 2019
BDSM

This story has been created with Game Mode in mind. For the best experience, please turn Game Mode on. Your best friend Eddie had said it was urgent. Upon receiving his text, you head to your normal meeting place, Godzilla's Pizza Dojo. The place is covered in framed monster-movie posters and arcade machines that Eddie has topped the high scoreboards on. You...

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An Anal Beginning Ch. 01

by caffinated on Sep 16, 2017
Anal

This is the beginning of a longer story. It is the first piece I am publishing in this format. Your feedback is welcome. John's deepest desires left him lost. He longed for something that went against every fiber of his being. John's girlfriend Heather had opened a door to his sexual exploration, and now John longed for more. His deepest desire was hard en...