Gay Losing Stories

3,330 results
Orientation
Length
Source
Infinite Scroll

Winners and Losers Ch. 07

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous instalments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players. Previous chapters for Winners and Losers are on Literotica. * * * * * There was no denying that the last minute loss to AFC Kerlon had dented confidence in the dressing room, but when...

Defeated Jock Ch. 01

by maxpotter on Mar 12, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** "Stop it Taylor!" Pam slapped Taylor's face. Not hard enough to do anything but give him a little sting, only to register her supposed displeasure. "Stop what?" Taylor moved his hand further up her skirt. They were on the patio of a bar in their college town, but in the d...

Friends Become More Ch. 08

by Singlegayboy666 on Jun 1, 2020
Gay Male

***Alex's Point of View*** Our one year anniversary rolled around, Ben said he's planning the night. I told him not to go crazy, all I care about is being with him. I got home from work and Ben wasn't there. Weird, considering I thought he's supposed to be off tonight. "Babe?" I called out, looking around the house. "Ben?!" I searched all four floors, wei...

Erotic Mud Battle Ch. 02

by mudwrestler on Aug 28, 2017
Gay Male

Andy had beaten me fair and square. But I now faced 3 very horny clay covered guys sliding towards me as I lay in the mud totally spent. Before I could ask what was going on Andy had gripped my ankles and pulled me a short distance on my back. My legs were raised up and Andy's hard cock was thrust between my feet. The other two guys slid either side of me a...

The Beach

by bybiguy on Aug 18, 2017
Gay Male

Hobe Sound Mid-south Florida, in the fall of 1983. I was working just South of Ft. Pierce and had been told of a "nude" beach, 10 to 15 miles further south. I decided to check it out, the idea of being nude in the outdoors had always intrigued me. I had already been in Florida for a week and had the makings of a pretty decent tan, but the idea of losing th...

Hot Wet Cabin Orgy Ch. 02

by Abaddon89 on Sep 15, 2017
Gay Male

Alex had promised himself and Stacy that this time would be different. No more prank calls from the cabin, and definitely not as much drinking as last time, or whatever he had been on. He had actually believed this too, since that time had just been a one-time thing, an experimentation. He was back to fucking Stacy's cunt, and it felt good to him. He definit...

Whole

by doveglion on Aug 18, 2017
Gay Male

It didn't fall apart at first. Instead, a spidery trail shot from the wounded center just above the stem. I watched the white fractures drag across the rounded surface; I watched the wine slowly, slowly begin to seep through the fresh cracks—only just lining them with deep burgundy before beginning to slide down the smooth walls. I watched the liquid push ti...

First Time with Family Friends Pt. 02

by jtwy on Jul 6, 2020
Gay Male

James was pleasantly surprised by how normal everything was after losing his virginity to his straight family friends, Josh and Matt. After they fucked, the three of them had watched some TV and fallen fast asleep, only to be woken up bright and early the next morning by an alarm on Matt's phone. It was their first day of skiing on this tri-family Christmas...

King of the Strippers Ch. 02

by BothWorld on Aug 18, 2017
Gay Male

Chopper pointed towards the back of the club. My knees almost gave out. With his firm grip on my shoulder we started walking. My head was spinning. I had no idea what he was going to do. He opened the door to the back office and pushed me inside. The office was richly appointed. There was a desk to one side with a bar and couch on the other. He turned and...

Caught and Caught

by Geitsu on Jul 13, 2020
Gay Male

"What the hell...is this?" The moment I walked in, my best friend Jackson started staring at me dismayingly. He was pointing at the LCD TV on my living room, sitting on the couch placed direct opposite to it. "What's wr-" The scene I saw destroyed the composure I needed to complete my sentence. There was a footage playing, footage of two naked people partic...