Gay Stretchy Stories

155 results
Orientation
Length
Source
Infinite Scroll

Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...

Truckstop Young Wife Neighbor

by Alluring_Crimson_Shifter on Jun 12, 2019
Gay Male

Wendy lived with her husband in a middle class neighborhood. It was a comfortable neighborhood with a convenience store within walking distance. There was a retail strip nearby with hair salon, a barber shop, parts store, and a book store with an arcade. Also there was a truck stop next to the neighborhood across a wooded area. On this sun shiny day Wendy w...

Ben Loves a Challenge Ch. 03

by PDreadful on Nov 11, 2019
Gay Male

"Didn't I tell you not to call me?" Dean asked from his rolled down window. Ben smiled, stepping up to the curb, feeling somewhat back to normal, and drunk, but not terribly drunk. "Did you?" "Oh, now you're cocky, cause you're drunk. It's too early for your dickhead friends to have left you," Dean said. He shrugged and pulled the door handle, but the doo...

Back Crack Tag Team

by buttcheeks777 on Feb 6, 2018
Gay Male

Editor's note: this story contains scenes of non-consentual or reluctant sex. This is a fantasy of a man (me) being forcefully taken by other men and contains some things that not all may want to read about, including spanking, anal sex, pissing, enemas, etc. If you're not into this type of fantasy please don't leave negative feedback. If this turns you on,...

Co-worker's Man Ch. 24

by rmdexter on Sep 14, 2017
Gay Male

As Claudia ascended the stairs and crossed a raised area that overlooked the main foyer, my eyes were glued to her long shapely legs encased in her sheer black stockings. As I mentioned after meeting her in the sex shop, she was a tall women about 5'-10". With her high-heeled sling-back shoes on, she rose to over 6' tall and towered over me. Her round perfec...

Kasper's Den Ch. 06

by tarzanacide on Sep 19, 2017
Gay Male

My 50th story on Literotica. Thanks everyone for your support! ***** "I met you in the dark, you lit me up You made me feel as though, I was enough" "And what happens when you cry in front of the Hamad family?" The psychiatrist asked me. Mr. Hamad had filled him in on the situation with my parents. He asked all about my childhood, my family, my dad. I...

Surfers Experiment in Speedos

by speedodave on Sep 14, 2017
Gay Male

I used to go to surfin' at Torquay or Jan Juc or Bell's Beach with my flatmate. To tell the truth, Gazza was more than my flatmate. I was in love with him. He wasn't in love with me though. Oh, he liked havin' me around. And when he didn't have a girlfriend over he was happy enough to fuck me. Sometimes when he did he'd even call out my name as he emptied hi...

My Little Secret

by whome712 on Aug 22, 2017
Gay Male

I don't even know where to begin. It's such a hard story to tell, and I'm afraid that it doesn't show me in the best light. I guess I should start by telling you about myself. I'm a happily married man, 47 years old, 6-2, 190 pounds. Maybe not the best looking guy, but I keep myself in shape and I work out every day. Grey hair, blue eyes, nice smile. As...

Fun and Games Ch. 06

by jm02201960 on Sep 15, 2017
Gay Male

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it an...

Val's Badminton Ch. 05

by maudecardy on Sep 17, 2017
Gay Male

"In case you hadn't guessed, Gee and I have a very open marriage, don't we love?" smiled Val, my badminton tutor, putting her hand under her husband's chin. "And my gym is where we can let off steam in a very healthy way! Now I'll just go and have a quick shower, so why don't you show Andrew all this equipment? And Gee - you've still got your gown on! Cardie...