Crossdressing Bet Stories

66,523 results
Orientation
Length
Source
Infinite Scroll

Smoking With Friends Ch. 01

by jjww100 on Sep 16, 2017
Transsexuals & Crossdressers

The phone on my nightstand rang and I groaned as I grabbed it and looked at who was calling. It was Benny and I answered it. "Hello". "Yo Justin, I got $250 worth a weed! You need to come pick us up so we can smoke it!" "Just Wait. Who are you with?" "I'm chilling at McDonald's with Matt and Vic." "Okay, I'll be there in twenty minutes." I hung up, qui...

Sarah Was Caught Masturbating

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

After collage, my girlfriend's best friend and I found ourselves working in the same town and so we decided to share an apartment. Her boyfriend had another year to go in college and my girlfriend worked in a different city. I loved living with her; we became the best of friends; just friends but very close. We cooked together every evening and watched TV....

Staying Together

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"I'm not sure further sessions will be of much use to either of you. After seeing both of you twice of week for two months, neither of you is any closer to resolving your concerns than we were when you first came to me." Dr. Nelson was good. She had the ability to examine a problem, bound it, and then dissect it into smaller pieces. She'd done that with bot...

Taken Too Far Pt. 01

by SwitchSissy on Jul 2, 2018
Transsexuals & Crossdressers

I had maybe taken it a little too far. It had started as it always does, a little light crossdressing at home. Then toys as well. Then wearing something a little extra under my boy clothes when I was grocery shopping. Then when I was at work. And that leads me to my current situation. On the outside, jeans, t-shirt – normal enough. Underneath though... It w...

Sarah's First Time Out Dressed as a Girl

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

During my collage days, my girlfriend and I were at different universities but they were only an hour apart by direct train. Normally I went to visit her for weekends. I loved her place, Oxford. They did great lunches on Sunday's. Full roast dinner with wonderful roast potatoes and all you can eat. For a broke, starving student this was a wonderful treat....

Brat Boys Punished

by humiliationstation on Feb 29, 2020
Miscellaneous

In this story you play as a series of boys.What's next? Martin, a 22 year old goth Albert, a 19 year old library assistant What's next? Martin, a 22 year old goth Albert, a 19 year old library assistant...

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Futa,furry and fetishes

by itthatlurks on Nov 18, 2018
Fetish

Welcome to the story, please choose a character. The world building will soon comence tomorrow as I am more interested in where the story goes first. So please be patient with me as this is my first story. For now if you want some of the concept then look to the synopsis. I have returned to the story after several months break and shall be, hopefully, postin...

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A Humiliated Tomboy

by humiliationstation on Feb 19, 2020
Exhibitionist & Voyeur

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.What's next? Claire, her bully Her best friends Nate and Jane What's next? Claire, her bully H...

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This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

Obey Thy Neighbor Ch. 05

by jealouscuck on Oct 29, 2018
Transgender & Crossdressers

I had gotten better results from my task than I expected. Li had instructed me to somehow include my wife in my panty fetish. By this time, fetish seemed a pretty tame word. My fetish had progressed to dressing totally as a woman and attending Li's fuck sessions. The last one she had me clean up her lover's cum from her pussy. The next step was to call me ov...