Gay Crossdressing Stories

23,246 results
Orientation
Length
Source
Infinite Scroll

Cocksucker: Crossdressing

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Straight man is forced to cross dress and suck cock. You do not need to read the first parts to enjoy this story about a straight man crossdressing in San Francisco. In case you are curious about how he ended up in this situation here is a brief summary of the first two parts of the "Cocksucker" series: Chris, a married straight man, is stuck at t...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

Your Waitresses

by weluvhose on Sep 15, 2017
Transsexuals & Crossdressers

We have not submitted anything for almost a year as daily life as certainly been in the way for ALL of us. My wife and I decided this one would be a slight change to the previous submissions. It is all fantasy but we both would enjoy bringing this one to "true" life if ever possible. Enjoy and we always welcome any comments!...

Lucy's Revenge

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

First of all, you need to understand I'm not gay. I've never had a gay experience in my life but have had a few fantasies over the last few years. I'm guessing that's because my sex life with my wife has faded over the years and I'm looking for alternative stimulation. Just a little background. When I was about 10 years old my older sister forced me into h...

Found Out Pt. 01

by Theta_Welt on Sep 16, 2017
Transsexuals & Crossdressers

My wife looked at me, stricken. "It's yours?" she asked. I could only nod my head in shame. How had I brought us to this? She was holding up, of course, a lilac silk camisole. There was nothing like it in her wardrobe, and like any women finding another woman's clothes in her bedroom she had assumed the worst. Or maybe the truth was the worst, and her assump...

Ragdoll

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'd always assumed I was 100%, no exceptions, one-track-minded Gay; as gay as the day is long. Pretty damn gay. Really, nothing's happened that should technically directly challenge that, there was still plenty of cock involved... but I can't deny the fact I was attracted to some very feminine features. It's not even like he (or rather she) was crossdressing...

You Got the Part!

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

Coming up with the rent every month was becoming more of a challenge. I was a on again off again actor/waiter. My tips were good but I had to supplement them with acting gigs and odd jobs. This was the price to pay for freedom. I had a one bedroom apartment that ran me 1500 a month. I was avoiding taking on a roommate at all cost. I loved my privacy. A frie...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

Hostess with the Mostest Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Author's note: This ten-part story stands on its own but introduces characters from my previous story 'Transvixen'. It is not imperative to read Transvixen first but it will provide better context for those who like continuity. There is plenty of sex for those who like sticky fingers but also a decent plot and character development in my humble opinion. I wi...

Under the Gaze of the Sirens 02: Unknown Desires

by jakladd on Dec 2, 2019
Transgender & Crossdressers

We were in Minneapolis for a conference, 3 nights Tuesday through Thursday, leaving Friday morning. Our firm was a top producer of components for fiber optic technologies. Flew in from Orlando, got settled in the hotel, then on to registration and a meeting in the afternoon, dinner with a few co-workers from around the country. Ran into Warren from the main...