Gay Crossdressing Stories

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Infinite Scroll

Michael's Destiny Ch. 01

by CrossdressingDestiny on Sep 16, 2017
Transsexuals & Crossdressers

I peeked out at the blinds of my bedroom as my parent's car sped off into the morning light. Supposedly, they were going to some kind of camp for married couples looking to fix broken bonds out in the middle of Wyoming. Fucking Wyoming? I can't say I've really thought much about it until now... it is the least populous state. But soon my thoughts turned to w...

Set Up Ch. 01

by Sissy_Ashlee on Sep 15, 2017
Transsexuals & Crossdressers

This is my first attempt into writing an erotica story. This tale will contain themes of female domination, crossdressing, and eventually MM sex. If any of this is not you thing, please scroll on. Otherwise, please let me know how I did. ***** Since I was a teenager, I had been bicurious. Not really interested in men, but what is between their legs. My obs...

Webmeets Diary Ch. 04

by starbelliedboy on Sep 14, 2017
Transsexuals & Crossdressers

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. As I neared the en...

Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

Crossdresser's Private Gloryhole

by kccrossdresserleslie on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story, I am a crossdresser and this is the story of a wild wild night! HI. My name is Leslie, I am a very dedicated crossdresser. I have to live as a male by day because of work. At night I usually get home pop open a beer and pop a buttplug in my juicy hole, get on the computer and watching some dirty naughty things until I just have to dres...

Planet of Men Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

At 1600 Eastern Standard Time (EST) on September 27 in the year 2020 AD the UN announced that General Atomics Corporation (GAC) had saved the world. After years of panic in every country that the world was doomed due to the effects of global warming, GAC announced that, with funding provided by the UN, they had developed self-sustaining micro atomic reactor...

Best Camping Trip Ever Ch. 01

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a fictional work based on a fantasy of mine. Hope it comes true, and hope you enjoy.* ***** I love camping! I mean I really love camping. I also love crossdressing. And sex. With men. Yeah. I live for all the above. I have also begun to get a little more bold as the years go by. I wear tights or pantyhose under my jeans everyday, even during the s...

Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

Open in Reader

A Lot of First for Me

by amygurl on Sep 14, 2017
Transsexuals & Crossdressers

It all started about 2 months ago when a new neighbor moved into the apartment next door to me. His name is Jason, he is very personable and just an all around amazing guy. He is 34, about 6'3" with black hair and blue eyes and we hit it off pretty much as soon as we met. We are both veterans and newly single and we both liked to watch sports on TV, but we d...

Sarah Visits Chicago And Gets Lucky

by SarahCD on Jun 25, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...