Gay Cross Dressing Stories

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Orientation
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Infinite Scroll

Five in One Night

by jordan80 on Aug 18, 2017
Gay Male

When I walk into the bar there are only a handful of people inside. The bartender gives me a grin and a nod; guess that happens when you're a regular. The waitress comes over to take my order and I admire her uniform. This place is attached to a very nice hotel, so the waitress's uniform is a cross between professional and slutty. For some reason, that turns...

I Thought I Wanted It Rough... Ch. 03

by LonelyVirgin on Sep 14, 2017
Gay Male

How could I have let this happen? Every bit of it was my fault. I was responsible for the gag in my mouth and the handcuffs on my wrists. No doubt it was my fault that I was bent over the corner of a hotel room bed, with my legs bound tightly in opposite directions...spreading them wide. I was responsible for the school girl outfit I was currently sporting,...

My First Faggotry

by anna_subCD on Aug 18, 2017
Gay Male

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

Pull Toy Ch. 01

by thick_eight on Aug 18, 2017
Gay Male

pt.1 Seduction The beginning of the summer in 1962, I was 18, living in a small town between Ft. Lauderdale and Miami. As usual I was by myself, which was nothing new, considering I had been raised in the military, and was used to not having many friends, being the "new guy" all the time. I had decided that I wanted to get on the swim team, and I had the w...

Slut Scout

by Michele G on Sep 14, 2017
Gay Male

Our neighbors have a really good-looking son," Chad. His room is up in the attic of their house like mine is. Every now and then I see him in his window and he's seen me from his. He knows all about me and is cool about my cross-dressing. I see him with a lot of pretty girls. Sometimes I catch him sneaking them up to his room. The girls can get pretty loud a...

Knock on the Door

by alexcarr on Aug 18, 2017
Gay Male

"So it's you again, wanting your fix again I 'spose, Jerry?" "How did you guess," I asked like I was trying to be cool, all the while thinking no way will he let me into his life again. Thing is, - well okay I did dump Danny a year ago, it happens, - sometimes a guy needs to move on, search fields anew, thing is the field I searched did not bear oats - it w...

Rye's Encounters Pt. 01

by sissyrye on Dec 23, 2019
Gay Male

Note to reader: The following series of encounters are 100% non-fiction, best of my ability accounts of my real life encounters with horny men. Names, locations, and revealing details were altered to protect identities of course. PREFACE: Hi. My name is Rye. I am a cute, 5'9", blonde, big booty, white boy...with a hunger. I have a fairly symmetrical face...

Taking the Neighbor Ch. 09

by jjdtx on Apr 30, 2018
Gay Male

Allen came downstairs from taking his shower, he was naked and reached for his shorts. "Wait," I said, "You won't be wearing those." I beckoned him over to me, I placed a cock ring around his cock and balls, snapped it into place. "I love these!" He said, as I stroked his hard cock. I then handed him a t-shirt, plain, black, with no logos or emblems. He...

SynerGism

by assxible on Aug 18, 2017
Gay Male

I've been on the business end of several cocks, from short skinny little rascals that barely tickled, through the average sized that served quite adequately, to a few beefy rams that were painful and threatened to split me in half. Truly, size does matter. But several factors other than cock size matter just as much for sex to be considered phenomenal. Once...

Halloween Rabbit Holes

by hornyyoungboylovesolder on Jan 15, 2019
Gay Male

I had seen some men, one man many times, and was having a lot of fun. The one guy I was seeing constantly was 58 a bit of a belly, but an amazing cock. After a bit he had gotten me into cross dressing. It started with panties. Then stockings and heels. Leading to bras, skirts, and wigs. Eventually I was putting on make up, eye lashes, lipstick, the whole nin...