Gay Crossdressing Stories

23,246 results
Orientation
Length
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Infinite Scroll

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

Transvixen Tranny Rock Band Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One: Panti and Cherri Pops Panti's red nailpolished finger lazily circled the glans of Cherri's erect penis through Cherri's gauzy nylon pantyhose gusset. Preseminal fluid seeped from Cherri's palpitating member and darkened the sheer nylon. Cherri's white satin panties were bunched around her thighs and she bucked and heaved as Panti gripped Cherri...

Loving Wives

by NemosFolly on Sep 14, 2017
Reviews & Essays

First of all, it must be noted that I am not a writer of erotica. I find it much more fun, and erotic, reading stories where I'm not sure exactly what's going to happen (even if it's pretty clear from the direction of the story so far) than writing ones where I have such absolute control. But I am an avid reader, and I have read many stories in each of the c...

Hotel Encounter Pt. 01

by Jay876 on Aug 20, 2019
Transgender & Crossdressers

Jay was a 5 foot 10 Indian boy, he has longish hair and he is a little chubby. And this is the story about how he lost his virginity. He was sitting at home browsing through the gay apps. His hand slowly rubbing his dick. Just enjoying the erection. When suddenly he received a message from an older white man. Jay had always fantasied about being with an old...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

The Doctor's Appointment

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

My wife Jo had been suffering with a bad back for weeks. She works as a doctor and many of the procedures she has to carry out on patients require her to stand up for hours at a time. A couple of moths ago she fell off a horse on an activity holiday we were on. And she's never fully recovered. Urged on by my insistence to get her back checked out properly...

Sarah Visits Chicago

by SarahCD on Sep 19, 2017
Transsexuals & Crossdressers

I was on a business trip to Chicago and I was staying at a nice downtown hotel. I decided to go out for the evening dressed as Sarah. Well, what did I have to lose? No one knew me there and I would never see anyone that I met again. I put on blue lace panties and a matching bra. It was a warm summer evening and so just I wore an ankle length blue strappy su...

June Meets Dale

by june613 on Sep 14, 2017
Transsexuals & Crossdressers

I've been wearing Pantyhose for almost 30 years now, and I still have as strong a Fetish for them now, as I did back then. About 17 years ago I started meeting other Pantyhose Crossdressers or Pantyhose Lovers for Kinky sex. About 4 years ago I replied to a posting on Craig's List from someone looking for a Pantyhose Crossdressing partner. We met in stree...

The Basement Ch. 02

by FiveDots on Dec 24, 2019
Transgender & Crossdressers

I received a text the next evening. 'Hey dude, come down here and check this out.' Not yet ready to confront him with a revenge plan but not willing to ignore him either, I traveled down the stairs to the basement. My roommate had used the threat of exposing my questionable internet history to coerce me into letting him shrink me temporarily to pleasure him...

Selective Fetishism

by Magnolia13 on Sep 16, 2017
Reviews & Essays

Is it possible to have “selective fetishism”? What I mean is that sometimes in some circumstances I find myself irresistibly drawn to one thing or another that could become a fetish if I were to find it appealing all the time. The word ‘fetish’ doesn’t really fit as it implies a desire that is permanent and always necessary for arousal. I find some things...