Gay Overweight Stories

367 results
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Infinite Scroll

Sucking Cock in the Woods

by Closetfaggotnyc on Aug 31, 2017
Gay Male

I heard about the spot in the park from a guy I met online. He was an older white man. Not particularly good looking. Didn't have a great body. Didn't have a great cock, but I needed cock and he was the only one who responded to my craigslist ad that day and I went with it. We met at a nearby seven eleven so I could check him out before inviting him back t...

First Time at the Sauna

by nathanstales on Sep 25, 2017
Gay Male

I turned into the narrow entry and followed a solitary, small sign pointing towards a black door. I was nervous, but as I stood outside searching for the courage to push the buzzer, I knew there was no turning back. I had come this far. Searching for saunas in my area on the Internet, I found the phone number of one and called to check opening times. I knew...

Drunken Follies Ch. 01

by overzealous20 on Aug 18, 2017
Gay Male

First story! would really appreciate votes so I'll know what to do next! Innocently I sat on the train, afraid that any movement on my part would cause me to tip over. I couldn't help but laugh at myself from time to time, wondering how I always got into these situations. I would go out with a group of friends, telling myself I'll only have a couple of shot...

Doctor Patient Privilege

by chubbymindiana on Aug 18, 2017
Gay Male

"Kyle?" The sweet voice of a young Hispanic nurse broke Kyle Harris out of his waiting room stupor. He looked around and saw that the nurse was standing at the door to the examining rooms. He stood up and set down the Highlights for Children, only magazine he could find in the whole waiting room, and walked back to the door rather stiffly. "So, Kyle, you're...

One for the Road

by newpaulman on Sep 14, 2017
Gay Male

When Neal invited me to have Sunday lunch with him in a pub I wasn't entirely sure I should go. I was new in town and had just met him in his capacity as bank employee when I went to open a new account. He was medium height and very overweight, with white hair and a friendly beard. I can't say I was immediately attracted to him, because I'm basically straigh...

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...

My First Ever Gay Date...

by Thenaughtypen on Jul 27, 2020
Gay Male

Here is the deal. Last week I went on my first ever date with another man and since that night I have just been bursting to tell someone, anyone about it. So, first about me. I am 48 and divorced. I was married for 15 years and although most of it was good (well, until she started sleeping with her boss) I always fantasised about being with a man. When I j...

Boy Story

by azburglar on Aug 18, 2017
Gay Male

I was going through some hard times recently. My job was cut during the recession and I was trying to get by on the meager unemployment check I received. It didn't help that I had a bit of a gambling problem. I was badly in debt but pretty much judgment proof so I didn't worry too much about it. Sometimes I would take my weekly check to the casino on the edg...

Alan's Beach Party

by newpaulman on Aug 20, 2018
Gay Male

I lay on my back, naked as the day I was born and feeling like a teenager in the presence of the man who knelt above me. We were sweating profusely in spite of the air conditioner's efforts. It was midday on a Tuesday in August and I was on Alan's bed in the timeshare he owned on the Caribbean island called Saint Maarten. Alan was the most experienced guy I...

Losing My Gay Virginity

by Lostboy11 on Jul 2, 2018
Gay Male

***This is a real true story of my first gay sex about 10 years ago, I did not use a condom because I was young and stupid, please always practice safe sex**** ***** I was in my 3rd year of college and home for the summer. I went to school out of state and thus could not out with new friends, and I hadn't bothered to keep in touch with people from High sch...