Gay Lost Bet Pegging Stories

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Backdoor Man Ch. 05

by SEVERUSMAX on Sep 16, 2017
Gay Male

We were startled into standing up as we heard Sherry and Sanjay re-enter the dining room/kitchen area, the somewhat dazed and enchanted delivery guy now being bent over the table, as Sherry winked at me and strapped on her dildo with her thigh harness. She lubed it up and spread Sanjay's now smooth cheeks to add some lube to his sphincter before she began wo...

Slut Used as They Desired

by Penisleeve2020 on Jul 6, 2020
Gay Male

I went to my favourite sauna and after stripping down, adjusting my very tight cocking went to the balcony and smoked some very good weed before cruising. In the maze area there were a lot of men and many were crowding around in the dark watching a couple fucking really hard and fast, I decided to kneel nearby and start fluffing the line until one man asked...

Pegging Peter Ch. 06

by KenJames on May 23, 2018
Gay Male

Peter kept thinking about his first time during the drive to Mark's apartment. He and Janna had been dating for two years, gradually progressing from tongue kissing to mutual masturbation. The last time, in the back seat of his dad's Suburban, he'd pulled her panties down, then eaten and fingered her to orgasm. She'd given him a great blow job. After he'd c...

My Time with Brian

by alexcarr on Aug 18, 2017
Gay Male

Criticism much appreciated, this is a rewrite of Brian's Fuck and have changed the title as you suggested. * I felt Brian's fuck like I knew I would. He was a big guy and I just knew when we did foreplay it would hurt first time, but the fact is I wanted it and I wanted to share the experience with Brian who I trusted implicitly. He took me nicely, gently...

Cum Delivery

by Patrick2380 on Jan 21, 2020
Gay Male

I had the house completely to myself, a rarity these days. Literally, no one would be home until the next day. Not needing to worry about any possible interruptions, I decided I was going to have an epic masturbation session. Back when I was single and lived alone, I could watch porn and jerk off for hours at a time. So after having a little breakfast and...

Erotic Massage

by HerLittlePiggy on Apr 3, 2018
Gay Male

I laid face down and naked under a towel on the sturdy but narrow massage table. My heart was racing and I had a flutter of butterflies in my stomach. I closed my eyes and breathed deep, drawing the scent of candles into my lungs as I tried to relax. Warm oil drizzled onto the exposed flesh of my back and my breath caught in my chest. I couldn't believe was...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

My Memories of David Ch. 03

by msmithyxx on Sep 14, 2017
Gay Male

Sometime after that first weekend where David and I discovered our desires for each other, things carried on getting better and better. We slept together frequently, we stopped going out on weekends looking to get laid and instead we started to enjoy each other's company more as lovers, rather than just friends. Although we kept things largely behind closed...

Pegging Peter Ch. 07

by KenJames on Jul 11, 2018
Gay Male

Peter was nervous as he and Mark walked into Smokin' Ruby's, the barbecue place on the ground floor of Mark's apartment building. Even as a horny teenager, he'd never been into casual sex. Girls had hit on him in high school and college, but he'd politely turned them down. He had to get to know her first. He and Kyra had dated for a month, seeing each other...

Are You Game? Ch. 05

by 2ndAlias on Feb 12, 2019
Gay Male

Super Bowl I headed over to Ben's place that afternoon with a rock hard boner in my pants. I was mildly disappointed to find that Joe was already there, seated in the living room checking his phone. As I closed the door behind me, Ben bounded out from the kitchen with his arms stretched wide. "Hey, buddy!" he exclaimed enthusiastically and clasped me in...