Gay Sissy Crossdresser Stories

774 results
Orientation
Length
Source
Infinite Scroll

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...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

Bathhouse Roles

by glory_first on Sep 14, 2017
Gay Male

Arriving right at the bathhouse's opening time on Tuesday, the sky dark enough to think that rain would be arriving soon, the entrance was busy. 5 stacked bundles of the latest edition of a free local gay magazine were outside the door. Going in, before I could mention the delivery, a man with a blue t-shirt that read "I like face fucking - ask me" brushed b...

It Could Be Worse Ch. 05

by eviltwin52 on Sep 14, 2017
Gay Male

Note to readers: If you don't like IR, gay male, and cuckold stories please move on. You can jack off to some one else's imagination. My stories aren't required reading. And yes, I know. I'm a twisted fuck. Lastly, I never sucked a cock. I was merely posing for dirty pictures. ***** Two years after I sucked my first load of cum from Jim's cock and then w...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

Beauty and the Beast Pt. 03

by Suzzique on Jun 3, 2019
Gay Male

"Well, well!" said Daddy in a tone of mock surprise, "Your Uncle Ted has made it here after all. And for once he's timed it just right." "You promised," I cried out, on the edge of tears again. "I lied, you dumb sissy. I lied." He laughed. "Cut the jokes, Jack. Give me the bitch. I've come a long way to get my cock up the little slut. I want her now." "...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

Hallowiener Pt. 03

by forummj on Jun 18, 2018
Gay Male

I yanked my cap down tightly and bowed my head. Hunching my shoulders forward I pulled my rucksack tight to my back and made a dart for the front doors. All my fellow students made their lazy way to class as the bell rang. I felt like they all knew what had happened last night, and I didn't just mean the party. I was nervous, almost scared that they knew. "I...

Uncle Marty Pt. 02

by Marty Fisher on Dec 23, 2019
Gay Male

This is a spinoff of my Brotherly Love series where my brother's son discovers his uncle's special talents...Part 2 *** I never thought "tomorrow" would arrive, but it did, and I woke up with my small penis tenting my panties thinking about what I was going to do today. Rose was sound asleep next to me as I thought about what had transpired between my brot...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...