Gay Craigslist Stories

396 results
Orientation
Length
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Infinite Scroll

Straight Boy to Bi Bottom Ch. 01

by young7inchfun on Sep 14, 2017
Gay Male

This is my first story. Please feel free to leave constructive feedback and let me know if I should continue. The following is a true story, with minor embellishments, of my first gay experience. Everyone in the story is an 18+ consenting adult. NOTE: if this story encourages you to use Craigslist or another online site, please be safe. My biggest tip is i...

Craigslist Success!

by chub2fxck on Aug 18, 2017
Gay Male

For weeks before it had finally happened I had spent time in the shower secretly rubbing my chub titties and fantasizing about being molested by another man. I had never touched another cock other than my own and the idea of being treated like a girl had always made me so aroused. When masturbating I had never experienced harder orgasms than while I had my f...

Craigslist Encounter

by james_ga_us on Aug 18, 2017
Gay Male

I live near Birmingham Alabama now and started looking at the ads on the Craigslist site for a chance to hookup with someone in person and not just through a glory hole like all of my other experiences. As I looked through the ads one in particular caught my eye. It said "MWM looking to top another MWM". The ad indicated that he wanted someone to come to his...

Yes I love being a bottom

by Jamie9919 on Nov 7, 2020
Gay

You just turned 18 and you now had the house to yourself for the night considering your mom had left to go be with her new boyfriend for the night. So you decided you wanted to try cock for the first time and decided to hop onto Craigslist personals and post an ad. After about 10 minutes you receive multiple emails but one catches your eye “Hi I’m 38 years o...

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Turning Into a Cocksucker Ch. 01

by Bolder22 on Sep 19, 2017
Gay Male

I always dreaded my office's annual work trip. A whole ten days dedicated to trainings and lectures with the other members of management. A small upside was that it meant a week away from the hassles of my kids and wife. My wife and I got married right out of college and had kids immediately. Now we were in our mid-thirties and it was nice to get away every...

Craigslist Chronicles Ch. 07: Steven

by Profanity89 on Apr 24, 2018
Gay Male

Hey All, continuing my series based around my early 20's... Thought I'd get it all written out before I hit my 30's. ;) Most of the chronicles I'll be releasing are based on real-life experience as I explored my sexual urges with other men. Again, feedback on writing is enjoyed! I love some constructive criticism. If your interested in editing some of my p...

Lonely Cock Sucker

by silkstockingslover on Dec 9, 2019
Gay Male

Summary: Lonely married cock sucker discovers young cock close to home. Note: Thanks to Tex Beethoven for editing this story. Note 2: This is a holiday 2019 Contest Story. Lonely Cock Sucker I love cock. I love everything about it. The variety of shapes. The upward curve that often makes me gag even on a smaller cock. The downward curve that slides int...

Please Fuck My Ass

by atitagain991 on Sep 15, 2017
Gay Male

Once I hit my late teens I knew I had to try cock at some point. When I was drunk I craved it, especially hung over. I wanted to be dominated and didn't put it together that I was a bottom. There were a few instances where I would watch gay porn and masturbate. This caused some intense cumshot orgasms. My first attempt to play with another guy was organise...

Blow and Go

by Jay142 on Feb 6, 2018
Gay Male

My job requires me to travel on a regular basis and I get bored at times when out of town by myself. Once again, I found myself in a hotel room after a day of meetings not knowing what to do for the evening. Dinner and a couple of beers would kill a couple hours but the routine was getting to me, kind of like the rest of my routine life. After more than 20 y...

Another Craigslist Adventure

by hornyyoungguy69 on Aug 18, 2017
Gay Male

This story takes place over a span of about a year. It covers three specific meetings. I can't remember the main guy's name, but I think it was Mike, so we'll just go with that! As usual, I was horny as hell. I hadn't yet found someone who I could play with regularly so I was just looking for a discreet quick hookup to get off. I posted an ad for my area, s...