Gay Measure Size Bet Stories

9,883 results
Orientation
Length
Source
Infinite Scroll

Silk House Pt. 02

by jaiunus on Mar 12, 2019
Gay Male

Even though Toby and I were fully confident Mr. Doherty was deviously playing matchmaker with us, it didn't stop our play from turning to actual panic when, across the house, we heard the familiar sound of keys rattling. Conveniently, after a few hours of rollicking about I was still somehow free of wearing spandex gear—Toby liked to hold it against me after...

His Sweet Boy Ch. 06

by Her11 on Sep 21, 2020
Gay Male

AU: I'm Back! I know i was a little slow to write but im working on it. P.S. to Crven_ban: do not read my mind it freaks me out. To everyone else, 40th comment on His Sweet Boy Ch.04 ********* Ben slammed the office door, then spotted the bathroom and shuffled awkwardly into it slamming that door for good measure. Fucking hell. Eric was going to be the...

Prison School

by o2byoung on Sep 14, 2017
Gay Male

This is my first submission to Literotica. The idea for this story just hit me one day and I was up writing till after 4 AM. There are really no sex scenes in this first chapter, but it lays the groundwork for the chapters to follow. If you like where this is going, please send me some feedback. Even this first chapter wasn't quite what I planned, there are...

The Tailor

by TitusMoorhead on Sep 28, 2020
Gay Male

Despite his impressive body, the fit young man still looked awkward as he stood in his boxer briefs in front of the mirrors that reflected him from all sides. Will didn't mind the view of his chiseled frame, especially the way the light grey fabric of his underwear accentuated his tight bottom and thick bulge, but he wasn't used to being prodded at while so...

Joe's Physical Exam

by mrsensual01 on Oct 5, 2020
Gay Male

The day had finally arrived. My uncle handed me the keys to his gym, kissed me on the cheek, wished me the best of luck and got into the taxi bound for the airport. While I had prepared myself for these events it still felt surreal as they all played out. My uncle, the owner of "Muscles and More", had retired and turned the business over to me. He smiled at...

Licorice-Centered Milk Chocolate

by sr71plt on Aug 18, 2017
Gay Male

Heart racing, moaning, shimmering with anticipation, as milk chocolate, beefy-fingered hands glide over creamy white skin. Trembling as they search for and explore curves and crevices, zeroing in on heaving breasts. Groaning as rough-padded fingers rub, and twitch, and pinch tender nipples. Arching chest up from bed before the hovering milk chocolate monolit...

First and Only

by sr71plt on Sep 14, 2017
Gay Male

"Yes, hold just like that, please. You pose well." "As well I should," Philip answered as he put an arm up to lean on the frame of the door out to the balcony. All he was wearing was an opaque dress shirt, unbuttoned and gaping open, which was made even more opaque—luminous even—by the backlighting of the sun beyond the balcony of the eleventh-floor, Darlin...

Liam Ch. 01

by Lucas96 on Sep 14, 2017
Gay Male

Disclaimer: this story involves cuckolding/cheating. ***** Kyle and I were dating for almost a year now. We met early in our sophomore year in college, and when we entered our junior year together, we decided to rent an apartment together and see how things went. So far, it was going great. We had a lot in common - we were the same age (21), we both liked...

Thomas

by Pissdrinker on Sep 12, 2018
Gay Male

**Another essentially true story, but please note that condoms were used for the anal sex with Thomas. Play safe.** *** Thomas was one of our 2 plumbers, we found him after the first guy who installed our bathroom couldn't be bothered to return and fix a minor leak in the shower. He worked for a company recommended by the neighbour who rents some of our la...

Dew Drop Dead

by robertreams on Aug 18, 2017
Gay Male

I was hangin' out at the Dew Drop Inn, the local waterin' hole only two blocks from my house. I hadn't expected to get a game so my cue was outside in the trunk of my 66 Camero. I always bring my car, one never knows when one might need to cruise. I was getting really pissed. I had been sittin' here for almost two hours, listening to this dickwad hillbilly...