Gay Lost Bet Stories

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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...

Lost Bet

by hard169 on Aug 18, 2017
Gay Male

This is my first story. The story is factious. The names have been changed to protect anyone that might think I am talking about them. * It all happens by mistake.... I was driving home and notice the U-Haul truck at the neighbors unloading there worldly goods. It was a typical family, a couple of kids a dog and boat. They were trying to unload a sofa s...

Lost Bet 06: Didn't See That Coming

by dmoney4114 on Aug 18, 2017
Gay Male

After five minutes of arguing with Leo we had gotten nowhere, we were yelling in circles about trivial blights that we had done to each other over the years like the time he pushed me off a high diving board and almost drowned or the time I told on him for bringing our water gun fight indoors when it was really my fault, but other than minor offences we were...

Lost Bet 05: Angel's Den

by dmoney4114 on Aug 18, 2017
Gay Male

Lost Bet part 5: Angel's Den Am I cursed? I thought to myself as I escaped the game room I just had sex in. It had dawned on me that this was the second time in about as many months that my sexual exploits were intruded upon...and by the same person, my boyfriend's father. Given all of this evidence it is the obvious notion that I was cursed at some point i...

Lost Bet 04: Not Again!

by dmoney4114 on Aug 18, 2017
Gay Male

About two days after the ordeal with Greg when I came out to my parents, they claimed already knew. Leo came out to his mom but he couldn't get the timing right to tell his dad, or so he explained to me when we went on our first official date the following week. "Chicken!" I yelled when I heard this news. "No." Leo rebutted, "I just really haven't had the...

Lost Bet 03: Everything Will Be

by dmoney4114 on Aug 18, 2017
Gay Male

I went to the sun room of my house and let Greg in the back door. He couldn't meet my eyes, but I didn't put any clothes on so when he looked down all he could see was my naked body and Leo's cum dribbling down my thigh. So he looked straight over my head he wasn't that much taller than me but it was still effective. "What are you doing here?" I asked becau...

Lost Bet 02: So That Happened

by dmoney4114 on Aug 18, 2017
Gay Male

Lost Bet 2: So That Happened. "Shit!" Leo grunted multiple times as he wormed his way through the string web to get back to the other side of his room and throw on his clothes. I cleaned my chin and clothes with a towel I found on the floor. "Who do you think it is?" Leo asked me. "How should I know, it's your house" I replied. "You don't have to be ru...

Lost Bet 07: Next Year

by dmoney4114 on Nov 8, 2017
Gay Male

Lost Bet Part 7: Next Year I was walking on a treadmill as a jiggly ass cycled in front of me. I had a perfect view of every movement and ripple which allowed my thoughts to wander to last year. My string of sexual experiences starting with a bet on a childhood game that I had made up, and culminating in, a bill for a destroyed dressing room, and the strang...

Our Bet Ch. 01

by Elected on Apr 24, 2019
Gay Male

Lee grinned. "Won again." I grit my teeth in anger. What the fuck? This was my game. I'd barely even shown him how to play but somehow he'd gotten the hang of it in a few hours—and now he was beating me? This was such bullshit. Lee flipped my controller away carelessly and climbed to his feet, stretching with a groan of satisfaction. "I guess all that talk...

Straight to the Bottom Pt. 02

by Megahomingberry on Jan 28, 2020
Gay Male

Part 2 : Winter is Cumming On a cold winter day...about four days after my humiliating (and very gay) 'lose' to Brian...I was in the shower thinking about our bet and what happened between us. I still haven't cum to terms with the fact that I swallowed Brian's...I can't even say. Shame poured onto me like the water of the boiling hot shower. I can't believ...