Cuckold Slut Crossdresser Stories

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Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

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,...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Six Hours of Heaven

by diablofire on Sep 15, 2017
Transsexuals & Crossdressers

Authors Notes: This is the story of my first visit to an anything goes swingers club in Las Vegas. The night of the story I was one of the first arrive and one of the last to leave. ***** I finally sat down with my wife yesterday afternoon and had a talk with her about my desires to take my sexual desires to the next level and I was surprised what her resp...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

How It Began

by DarlenesToy on Jan 1, 2019
Loving Wives

Looking back, the seeds were planted early. In high school, I had been popular and always dated really good-looking girls. Marsha worked at a drug store in my neighborhood, she was awkward looking, but with a great personality. She was fun. The first time she asked me to take her home, I had her top off in the car and we made out, it was so hot. By the fou...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Your inner femboy

by SkirtSkirt on Feb 10, 2021
Transsexual

The first thing you have to ask yourself is, who are you Are you an ignorant boy about to be turned into a little cum slut?But then who was there to show you who you really are?Or did you do it to yourself? Or are you already a cum dumpster about to reveal themselves? Or maybe you want to be a slutty crossdresser that's secret gets exposed,one throat fuck at...

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