Gay First Time Bottom Stories

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Infinite Scroll

Imprisonment Ch. 03

by AgentK on Nov 8, 2017
Gay Male

Justin looked up with a sigh as the warden opened his door at the end of the workday Friday. He'd been dreading this day all week, and he was just now starting to be able to sit down comfortably after the abuse his backside had taken the previous Friday. He'd considered perhaps trying to stretch and loosen his opening so the next round of penetrations wouldn...

After Work Beer

by standingstones on Sep 14, 2017
Gay Male

This past week at work had been a rough one. I was stressed out by the time Friday rolled around. I don't usually do this, but I headed to a nearby tavern to get a beer before I went home. I had just gotten a draft and sat down at a table when some guy walked over to me. He was a tall blonde in his mid-twenties. I have to admit he was handsome as well. My lo...

My Love Doll and My Friend

by standingstones on Aug 7, 2019
Gay Male

I recently bought a love doll. Unfortunately, my friend Matt found out. We ended up sharing my doll Jessica together. After we both fucked her Matt told me he was a bisexual. Even more than that, he said he would like having man sex with me. I didn't reply to him but after all this happened, I started thinking about my friend. A few days had passed and Matt...

Never Say "Never" Ch. 04

by walterio on Mar 16, 2020
Gay Male

Ted was on the Monday morning conference call when Erin finally woke up and slipped his lovely trim body out of bed. He took a shower, douched his ass and put on a pair of knit underwear. He knew that the tight fit showed of his scrumptious ass and always got Ted's attention. It was almost 8:00 AM and Ted would be wrapping up his call soon. Erin poured himse...

I Popped a Cherry This Morning

by funandbold on Apr 17, 2018
Gay Male

I wrote this story a couple of years ago and posted it on another site. This is a true story...and everything after this was written about 2 yrs ago. Hope you enjoy it! ***** I posted a pic of my cock with this story so you guys will know what this 38 yr old virgin took and enjoyed! If you are still waiting for your first time don't worry about the size of...

Learning to Surrender Pt. 08

by miked1983 on May 29, 2018
Gay Male

Rick thought about the amazing sex that had been filmed for days. He wondered what he looked like and what Jack would do with the film while he was out of town. What was clear was that Jack was editing the video and would every day send a screen cap or two of the footage being edited with very lewd comments of how much he enjoyed that particular shot or mome...

Never Say "Never" Ch. 03

by walterio on Mar 16, 2020
Gay Male

THE WORK WEEK BEGINS Ted was up at 5:30 to make coffee and get ready for the 6:00 AM conference call. He peeked at Erin lying naked in bed on his belly. His gorgeous ass was poised for the taking but Ted maintained his discipline. It was going to be a long day with calls and scheduling appointments. Erin was no bother and never interrupted Ted except to r...

A Special Bisexual Bond

by walterio on Nov 18, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** BRENDA'S DISCOVERY Brenda came home early from golf that day opting not to have lunch with the ladies. Her new husband Chet was home with her only son and they were in the kitchen. For 50 years of age Brenda was the picture of fitness. She had a slender well-toned figure with har...

Correction by Mr. Kayne

by goodtimes21 on Aug 18, 2017
Gay Male

Some of this is true and it then develops into fantasy. The reader can decide at which point the true departs. * I was in my very last year of school, 18 years old, excited and frustrated about sex of all kinds. Horny. Very. Girls, men, anything. My friend Max and I headed off into the school woods. We used to play a bit together sometimes, we were horny...

Phone Call by the Pool

by fidofashion on Sep 17, 2017
Gay Male

I was lying in the sun by my condos community pool working on my midseason tan. . Instead of an actual swimsuit, I was wearing black bikini underpants. I had purposely worn them because they were light, I wasn't intending to get in the pool, and they had the bikini cut I wanted for my tan. My cell phone rang but I ignored it, and let the answering machine...