Gay Straight To Sissy Stories

22,823 results
Orientation
Length
Source
Infinite Scroll

It must've Been the Alcohol Pt. 02

by ggca11 on May 20, 2019
Gay Male

I appreciate all the feedback and comments on part 1 and hopefully you all like part 2 just as much (or more!) *** I must've passed out shortly after our shared orgasm. I woke up several hours later still naked and covered in (now dry) cum, and I could also feel some still lingering in my ass. Tim was sleeping naked beside me, his arm over my chest. I de...

Coming to Terms Ch. 02

by gaywheels23 on Sep 14, 2017
Gay Male

The following story is about a man coming to terms with his sexual orientation, as well as his feelings for his best friend. Characters are 18+, and any similarity to other characters or people is purely coincidental and not intended. Please feel free to leave any questions, comments, or concerns, as they will be greatly appreciated. ***** "Alright class,...

Long Time, No Suck Ch. 04

by Stontstr on Sep 1, 2017
Gay Male

That weekend was amazing. I felt really great about my relationship with Marc. Cloe, Stephanie's girlfriend, turned out to also have a surprise. See, she turned out to have a rather nice penis, a nice extremely large, uncut penis. Cloe had even named it, Clarence. Marc had to go back to town on business for several days, but Stephanie said he knew all about...

Sean and Jason

by mstrhole on Sep 1, 2017
Gay Male

When I first saw him, he was sitting on a park bench (and, no, he was not eyeing little girls with bad intent). He was reading a book. Later, I would come to understand that this was his default state. In this instance, the book was William Gibson's Neuromancer. I was pleased. Literate and sexy; the intellect and the libido are inseparable after all, or sho...

Just for Fun Ch. 01

by masked_machine on Aug 18, 2017
Gay Male

Jeff was the class clown, never ashamed to disrupt order, never afraid to blurt his thoughts louder and more clearly than the "authority" figures dared. His bravado annoyed me only slightly less than his drive to make sure that all of the other students could hear his daily assaults on the broke and broken public education system masquerading as "Authority....

College Jocks Ch. 01

by busty_mclusty on Aug 18, 2017
Gay Male

I walked into the locker room, feeling good about my performance on the court that day. I was a college sophomore on the basketball team, and life really couldn't have been better. I was on top of my game, had lots of friends and girls were throwing themselves at me all the time. I hadn't joined a fraternity (I still got into all their parties, though), as I...

Brotherly Affair

by penguin_ on Aug 18, 2017
Gay Male

a/n: In my opinion, if you're looking for something quickly jerk off to, then [like I said, IN MY OPINION] this story may not be for you. Some parts have a lot of talking, and some don't. Also, the story and characters are 18 and above, and bear no resemblance to any real life people and if any, is just pure coincidence. So ya, enjoy. # Hi. The name's...

Peter, My Neighbourly Hunk

by Mr Story Teller on Aug 18, 2017
Gay Male

Pete is a neighbour from a few doors away; he has always seemed a quiet sort of bloke who I'd spend the odd moment having idle chit chat with when our paths crossed in the street. I didn't know anything about him other than he lived on his own and enjoyed cycling, he could often be seen cycling off on his racing bike with his tight lycra shorts on and bare l...

Born to Suck Ch. 08

by rmdexter on Sep 19, 2017
Gay Male

We both finished rinsing off and I shut my own shower off once Sven had turned his off. I reached for one of the towels he'd brought in and looked at Sven as I started drying myself. He had a scornful look on his face and stood there with his hands on his hips shaking his head in disapproval. "Wh....what?" I asked, totally confused. "You've still got a lo...

Opening Z Ch. 12

by polaris_flight on Sep 14, 2017
Gay Male

My alarm woke me. My hand was holding my balls supporting a raging boner. I slid outta bed and did some warm ups; I needed to run. I stuck my head out, looked out the hallway window at the flat grey skies, no rain. My boner hadn't eased. As I pulled on running shorts and socks my head was foggy; I felt a rejection of the fears of last nights. I remembered ho...