Gay Sissy Breeding Stories

1,115 results
Orientation
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First Time Gay Anal and Breeding

by RoughBreedingLover on Sep 25, 2017
Gay Male

I've always wondered what it felt like to receive a creampie, at 24 years old I finally decided to post an ad on Craigslist. The ad was named "wanting first time gay anal with a deep breeding creampie." I wasn't interested in blowjobs and anything I just wanted to be topped really hard, balls deep with the absolute minimum amount of lube so I would really...

Nephew's Readjustment Pt. 13

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. * The next weekend, Cynthia called her nephew over in the afternoon. It was time to start preparing him for the next phase in her ever growing plans. She knew th...

A Very Dirty Little Sissy 'Girl'

by keptsissy on Aug 31, 2017
Gay Male

I love to please my boyfriend. I masturbate thinking about that. A lot. To hear him when he's in me, on top of me, lost to my tight little hole or my mouth, I love the sound of him, the 'man' noises he makes! But as much as I like to please him, I just like to please men. Do I ever. I've been at it since just after high school. And there is nothing hotter th...

Job Evaluation - New Attitude

by VeryCuriousIan on Mar 18, 2020
Gay Male

Ian stared at the ceiling as he lay in bed, his girlfriend Debbie asleep at his side. He could not sleep, all yesterday's images flashed through his head. No way around it, he had sucked his bosses cock in his office and been forced to swallow his cum. Even worse, his bitch of a line manager had watched him do it. The waves of shame and embarrassment washed...

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...

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...