Gay Lost Bet Stories

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Orientation
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Infinite Scroll

Jared Ch. 02

by andrew1990 on Sep 1, 2017
Gay Male

Jared woke with a start. Had it all been dream? He moved. His fears were confirmed. He hurt in places he shouldn't hurt in. He ran to the toilet and nearly screamed during his routine emptying of his bowels. Why me? He thought. His hole ached and blood appeared in the toilet. He had been violated and worst of all he couldn't tell a sole. When he cleaned up...

Unexpected Layover Pt. 01

by Hot4TS2003 on Dec 30, 2017
Gay Male

Peter Stephens had anticipated the hotel lobby would be crazy, but not this crazy. What the airline had described as a "scheduling software glitch" escalated into dozens of grounded flights, with hundreds of stranded passengers. There were probably 50 or 60 people trying to push their way to the desk clerk, hoping to get one of the few rooms left. His own...

College Cock Sucking Slave

by fulhammock on Aug 29, 2017
Gay Male

Edited by: Mistress_Paz (Thank you Mistress!) In high school I used to fantasize about juicy fat cocks all the time. I would imagine sucking a nice fat one as I jerked off but never thought I'd actually go through with it. Man, was I wrong. I had four years of cock sucking fun all through college. During freshman orientation I was introduced to all the guy...

Lost Bet

by dmoney4114 on Aug 18, 2017
Gay Male

"I can't believe you're leaving man" I said to Leo as we walked to his house "if you leave I'm going to be left here with Jordan!" "Jo is your best friend, your better friends with him than you are with me." Leo replied. "Well yeah" I admitted "but he doesn't cook, and I've had more free meals at your house than a homeless shelter, and I know I work at a h...

Naked Earnings Ch. 03

by tzael2003 on Sep 1, 2017
Gay Male

I'm Dan, a 45 year old white guy, after the passing of my wife I returned to my old home and my son Tim. For an old guy I'm in good shape, 5' 6" around 140 pounds. I'm a pretty solid body, firm muscular legs and firm strong arms. My son is taller than me and in better shape. He is like some Greek god, with sculptured chest and abs, muscular legs and a well f...

Chat Line Leads to More

by nowiamhere on Aug 18, 2017
Gay Male

I am your typical straight guy in terms of looks. Generally most people consider me fairly conservative. I was in-between girlfriends and starting to get quite horny. It was late on a Friday night and I saw an ad come on the TV for one of those meet other singles phone lines. What the hell I thought, and I dialed in. The girls mostly sounded a bit rough for...

Are You Game? Ch. 02

by 2ndAlias on Sep 14, 2017
Gay Male

Divisional Playoffs ---Saturday On the way to Ben's place that afternoon, I ran into Erik in the hallway and we took a few minutes to catch up before going inside. Erik's cousin is married to a friend of Joe's and the two of them struck up a friendship through that connection. I had first met Erik, along with his wife, Janelle, at the same holiday party...

Letting Him Down Easy Pt. 03

by vikkihawe000 on Dec 2, 2019
Gay Male

"Checking in," Jessy said to the hotel clerk. "Reservation under the name 'Jessy Smith.'" The woman with the frizzled hair looked concerned for a moment, but shook her head. "Here you are, first to arrive in room 3320. How many keys would you like? 2?" She said glancing up at Eli standing next to her. "Five," Eli corrected her. "We're having a few friend...

The Day I Sucked Three Black Cocks

by reddevil58 on Sep 14, 2017
Gay Male

I sat down when I arrived at home feeling exhilarated, and shocked at what had just happened. Only this morning I was a regular married heterosexual guy with kids. I had never had sex with a man although I had fantasised about it many times. I often asked myself why I had never done anything about it. And the answer I always gave was that it just never happ...

Breaking Lance Ch. 10

by martin_x59 on Sep 14, 2017
Gay Male

The mood is mute, six men sit in Vince's lounge, all wearing dark suites. "I felt the funeral was very touching, especially your eulogy Lance," Don says breaking the silence. Lance stands up from the dining chair he was sitting on. Lance is wearing a suit Jacket that is five times too big for him, it was the only way of getting the sleeves over the plaster...