Gay Shemale Surprise Stories

7,774 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

First Cock Came From Old Friend

by Trinni69 on Aug 31, 2017
Gay Male

It was Saturday and I had nothing to do so I decided to go for a drive. I got into my car and headed out of the city in no particular direction. After driving for a while I realized I was close to Jim's house. We have been great friends for years but have not seen each other for a long time. I decided to surprise him by dropping by unannounced and see if he...

Third Trip to the Dream Boutique

by toddmac781 on Apr 17, 2019
Gay Male

I happened to have a rare afternoon free in the middle of the week. With no one to bother me, I could enjoy some fun for myself. So, naturally, I decided to go to the local theater and enjoy the day there. I've described the theater's layout in my previous stories, so I won't use as much detail as usual describing them. I had already scoped out the booth...

A great night

by softcell on Sep 7, 2006
Gay

This bar was quickly becoming my favorite hangout. The booze was cheap, the atmosphere was lively, and the restrooms where clearly marked. Even though this was my first time here, I knew I'd made the right choice to come and check it out. There were lots of people in the bar and while I was checking out everyone while sipping on my vodka on the rocks, two fe...

Open in Reader

Teenage life

by JONASger on Jan 1, 2018
Gay

I am an eighteen years old, young man. I am 6.1" tall and a bit muscular, with a nice, big ass. I go to a school in L.A, where I live since 7 years. I really like all of the teachers, even tho I like the male ones a bit more. My math teacher, the teacher I like the most is a bit smaller than me but looks very, very fit and his bulge in his pants look re...

Open in Reader

Truth or Dare with the Guys

by BartyTrinky on Sep 29, 2016
Gay

Your name is Matt, and you just hit the lottery! Today, you just cashed the check - 450 MILLION dollars You immediately think of one guy to celebrate with - your friend, Brian. You have been friends with Brian ever since you moved to Las Vegas. You're both 21, and he's been Your best friend here. You've also known since you've met Brian that he's gay. At 6'1...

Open in Reader

Hot Ch. 02

by FantasyWorld2010 on Aug 31, 2017
Gay Male

********** It's hard to explain, but sucking his dick that night ignited something within me. There was clearly a sense of control over him, but the feel of his warm meaty flesh sliding across my lips and filling my mouth was intoxicating. It's as if I'm addicted to it now. The truth is that I have never wanted to try it, was repulsed by the thought of it,...

Big Bot, Sex Hot, Breeder Gets Laid

by danielblue on Aug 18, 2017
Gay Male

Tyler was really glad to find a new job, after being unemployed for a couple of months, but disappointed that he had to work with two macho, homophobic guys. Trouble was, the only work he could get was in a factory and the office he shared with the two guys was way out in the sheds, away from the main buildings so the badass breeders were the only people he...

Cat 02

by MeritCoba on Aug 30, 2017
Gay Male

I had not expected to see Cat again so soon. In fact I had fully expected to never see him again because I always felt extremely embarrassed after having had sex, especially when it was just sex driven by lust. The day I met him I had sex with no less than three other men besides him and thinking back about it, it made me feel uncomfortable, because I had fe...

Surprise at the Door

by Luckystiff2112 on Aug 18, 2017
Gay Male

This just happened to me today! But it all started last night. My buddy came over and we sat around shooting the breeze; took a ride in his hotrod- a '69 RoadRunner! Way cool! We came back and proceeded to get pretty drunk. So I fed him, gave him some water to sober him up some, and then he left. I was home alone now. My wife is away for the weekend, and wh...

Wanting a change

by ShaPop on Dec 1, 2016
Gay

John was a good looking guy, but always felt rather generic and lost in the crowd in his home town. He was of average height at 5'10, and at 25 had a trim hairy body with sandy brown hair and blue eyes, he was very much an all american guy. The one place he wasn't average was his cock, which was about 7.5 inches long, quite thick and circumcised. When it cam...

Open in Reader