Crossdresser Sex Stories

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From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

From a Husband to a Dutiful Sissy Ch. 08

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Readers, I so hope you are enjoying my story here. It sort of allows me to live vicariously through my words as Chantel. This story has been outlined to allow me to write it in an encompassing and linear way. I try not to wing it but to paint a story that is life-like without being boring, well at least I hope it's not. I hope my characters are believable an...

Sissy in The Hart of the Valley

by EvelynT on Sep 16, 2017
Transsexuals & Crossdressers

The story so far; having completed the first date with Harold Plumrose and with over a month until the scheduled second date Sissy Betty Blane spends time at a t-girl club with Cindy. ***** When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persever...

Online to Real Time

by sandraCD on Aug 30, 2017
Fetish

We first met on line in a chat room called crossdressers for males. I first met and was chatting with Bob, one half of Bob and Ann. We chatted about anything and everything under the sun. We talked about everything from life’s experiences to politics. That first day we chatted for at least five hours. But what we were really getting at the whole time was, wh...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

From Dom To Sub

by ScarlettCD on Sep 14, 2017
Transsexuals & Crossdressers

Twenty minutes to go. A few days ago I had posted an ad online looking for someone to come to my place so that I could, to quote my ad, "get treated like a tranny slut by a true Dom of a man." I kept the ad low-key and photo-less to ensure none of my colleagues from work saw it of course, but more importantly, I was a Domme in my own spare time and did not w...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

My Name is Raquel Ch. 02

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. Well, at this point, I didn't know I was Raquel, just yet. I was just a thirty-something guy with a serious secret addiction to wearing and masturbating in panties. Secret that is, until my 19-year old stepdaughter caught me in the act. Now we share a panty drawer in her bedroom. We also have lots of masturbation par...