Gay Tights Crossdress Stories

168 results
Orientation
Length
Source
Infinite Scroll

Spiking the Eggnog

by ladynina23 on Apr 1, 2020
Gay Male

*All characters are above the age of 18 "Shhhh! You're family is going to hear us!" I shushed my boyfriend before going back down to swallow his cock to the root again. We were at his Mom's house for her yearly Christmas Dinner. About two hours had gone by when Ryan snuck up behind me. After five cups of eggnog, Ryan cornered me under the mistletoe and sai...

Ballet School Ch. 05

by BigWig69 on Jan 23, 2019
Gay Male

Chapter Five-Beck and Call Jim stopped by at his usual time and told me to follow him. I got to his room and went inside and on the bed were a series of butt plugs, small to really big. Here's what we're going to do Chris. Because I know you are horny for cock in your ass all day long, we're going to keep that beautiful ass filled up and pulsating with pl...

Kenith's Spanking Mode

by alexcarr on Aug 18, 2017
Gay Male

Visiting Lord Kenith had become a different kettle of fish from experiencing the needs of my other three clients. As a rent boy I had become accustomed to the various types of sexual encounters wanted of me. Most I could go along with but there were a few I declined. That way I could pick my cliental and give my best service to them via what I had to offer....

Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

I'll Use You Later

by stevedore on Aug 31, 2017
Gay Male

1. I'll admit I always had an interest in muscularity in men. A friend of mine -- he's a psychologist -- told me that it was natural. He said everyone, whether male or female, straight or gay, is attracted to rounded parts of the body: the breasts, buttocks, and the rounded limbs of the bodybuilder. But none of this explains my interest in penises. And, al...

His Sweet Boy Ch. 06

by Her11 on Sep 21, 2020
Gay Male

AU: I'm Back! I know i was a little slow to write but im working on it. P.S. to Crven_ban: do not read my mind it freaks me out. To everyone else, 40th comment on His Sweet Boy Ch.04 ********* Ben slammed the office door, then spotted the bathroom and shuffled awkwardly into it slamming that door for good measure. Fucking hell. Eric was going to be the...

Noah's Starship Ch. 15

by tarzanacide on Sep 19, 2017
Gay Male

Sorry for the silence... life got crazy. ***** +++ Noah +++ "You can't go home tomorrow. The news says Iran is dangerous," I urged Mr. Naseri. There had been an article about some nuclear deal going on and some people saying it was going to get us killed. "Noah! My home is not dangerous. It will be just fine," Mr. Naseri laughed. "I'm serious... it...

Workout Partner with Benefits

by dre_jones on Sep 19, 2017
Gay Male

This story is a work of fiction. All characters are fictional. This story is for adults and not to be read by minors, all characters depicted are over 21 years of age. If you like this story please vote, leave a comment or drop me an email! XXOO - Dre * 4 Days a week, every week, that's the schedule. I started with the usual warm up on that torture device...

Tales of Jason Ch. 03

by Bjsroxxs on Apr 21, 2020
Gay Male

Chapter 3: Patrick & Conrad When I left the bathroom the first person I saw was Patrick standing right outside the door. He looked me up and down as if he were checking me out. He smiled and said, "Those sweatpants look really good on you." "Yeah, thanks. They are a bit snug but comfy for now until my clothes dry." "Until then, Alkibiades would like to ta...

Ballet School Ch. 04

by BigWig69 on Jan 21, 2019
Gay Male

Chapter Four-Penance We both woke up at almost exactly the same time. He smiled at me and then laughed. "I'm so glad you're a morning man Jay." "Me too Chris, I love getting up early and training actually. Are you?" "Hell yeah, except for one thing might make me want to stay in bed today." "What's that," he said smiling. "This," and he put his hand on...