Gay Speedo Chastity Stories

791 results
Orientation
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Infinite Scroll

My Speedo Gang Bang Fantasy

by speedodave on Jan 23, 2019
Gay Male

I had my first orgy last May, there was six of us and I was the only bottom/vers guy there. My arse took a pounding to say the least. I wrote about it in depth on my blog. Today I was working on my stories archive and I found something I had written two years (to the week) before my first orgy. It was is a work of fantasy and involves twelve guys. My first...

Beefcake is My Bitch

by speedodave on Jul 31, 2018
Gay Male

I mentioned it briefly the other day that a friend of mine got in a bit of trouble with the law. It isn't too bad, he just drank a little too much and made some bad choices. Nobody got hurt and I don't think it is a 'habit' of his. I'm not going to defend his actions or decisions, he fucked up and he is more than paying for it. Perhaps because I am so disc...

Best Friends Finally Fuck

by speedodave on Aug 30, 2017
Gay Male

My friend Stephan came and picked me up on a cool Friday night. We had planned on camping out at the beach that weekend. So I packed my Speedo, some towels and a change of clothes. I stand at 6'3", normally dark brown almost black hair but I colored it green, down to my shoulders. I have hazel eyes, a trimmed beard and gauged ears. I'm pretty average in body...

Poolside Speedo Fun

by joeybarnum on Aug 18, 2017
Gay Male

I watched him from across the pool. I thought it was pretty brave of a man his age to be wearing a shiny red speedo like that, and of course it caught my eye. Speedos do that to me. It doesn't matter who's wearing them, how sexy they look in them, or how old they are. When I see a Speedo, I do a double take every time. I can't wear Speedos. I'd be a walking...

Speedo Erection at the Pool

by speedodave on Jun 1, 2020
Gay Male

While I have never had a spontaneous ejaculation, I do get uncontrolled/unintended erections when wearing speedos. Last week I went to the pool and had arranged with the Married Guy to maybe hook up afterward in the change rooms. Usually I just wear jeans over my speedos and leave them near the edge of the pool but it was kind of drizzling rain so I went in...

Naples

by undergear37 on Aug 18, 2017
Gay Male

This story is intended for a mature audience who can legally view this material. It is not intended to be viewed by minors or anyone else prohibited by law to view such material. No part of the story may be reprinted or reproduced electronically without the express written permission of its author. I always enjoy the feedback. * I dreaded the news that I...

Shattered Boundaries Ch. 02

by Humilifuck on Sep 14, 2017
Gay Male

At the end of a long night of fucking, after Jim had finished thrashing out his repressed frustrations on my ass and his orgasm had drained away his wrath; along with a flood of his semen into my exhausted hole. He would look into my eyes and smile a wicked little smile. I would move the world to see that wicked little smile again today. I first met Jim at...

Speedo summer

by tomch5090 on Jul 31, 2019
Gay Male

It was my last summer holiday until starting university, and I had nothing planned for weeks apart from relaxing and sunbathing at our summer home. A bit about me: My name's Tom, I've been with my girlfriend for 4 months now, but I'm getting more and more interested in guys Being an only child, I had more time to myself and having just turned 18, I was allo...

18yo Aussie Tom's First Time

by speedodave on Aug 18, 2017
Gay Male

As you guys may expect, I get a lot of emails from random people. Most of them are fantastic, like one I got last week from a Surf Life Saver who loves speedos (he sent a photo, I'll see if he will let me post it). Some emails I receive are weird, some are vague and I still get some hate mail mostly from religious nut jobs. I am propositioned for sex nearly...

Job as a Speedo Waiter

by speedodave on Dec 11, 2018
Gay Male

I saw an ad online looking for "Exhibitionist Waiter for Private Party". It was coming up to Xmas and I really needed the money. I was feeling pretty happy about my twenty year old body these days, I was training for some long distance swimming events which involved spending a lot of time in the pool. With all that training I was starting to tan up nicely an...