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rytomassi said:
I'm a huge exhibitionist and love jerking in risky places. Done the car while driving in traffic, fitting rooms (sorry Kohls), the leg press machine at the gym. I want more ideas.

I had to go to our Kohl's a couple of months ago to buy myself some new sweat pants. Of course the first thing I did after taking off my shoes and jeans was to take off my underwear also. I pulled off my t-shirt and stood totally naked (except for my socks) in front of their mirror stroking while looking at a collection of neighborhood MILF pics (copied from Facebook) that I have tucked away in the download folder on my phone.

I exploded all over the mirror and just left it there for the next customer to find.

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Fappy_Go_Fucky Amateur Jackinchatter

486 posts since 2013-09-30
59 year old curious male from Fort Collins, Colorado
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I can narrow it down to three:

Boy Scout camp, middle of the night, flashlight tucked down deep me so it couldn't be seen, in a tent with five other guys, looking at a picture a friend had given me and which I had hidden in my sleeping bag, torn from a porno mag, of the 70s porn star, Marlene Willoughby riding a cock. No one woke up and I used my tighty whities as a cum catcher and then stuffed them down into the foot of the bag.

Driving on the interstate, cock wrapped in the panties I'd just stolen from the laundry basket of a girl I knew, that everyone wanted, and that I knew I could never have. She was my cousin's college roommate. The irony being that I did later have her. And the panties? I washed them and slipped them back into their house the next time I visited. It HAS occurred to me just now that they might have belonged to my cousin. I have no problem with that.

High school journalism class, the darkroom, developing pictures of the girl's track team. I could feel myself getting ready to cum in my pants so I stroked it quickly into the trash can, pretending to be setting the timer for the chemical bath. Looking at an enlargement of the prettiest girl on the team, legs flexed and nipples hard, it took all of maybe six strokes. I am SO glad I don't cum that quickly any more. I was NOT alone in the darkroom. There was a journalism teacher and a fellow student.
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About 7 years ago I was obsessed by a friends daughter who was just about legal. One night when I was very high, I went to the back alley to spy on her in her bedroom. I never actually saw her or any sign of her but I pulled my cock out and furiously wanked my meat until I pumped one of the heaviest loads I've ever produced all over the back fence.
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Curious1972 Amateur Jackinchatter

155 posts since 2017-05-13
62 year old bisexual male from Southern Colorado
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When the weather outside is nice, my next door neighbor (50-something MILF with lovely legs, ass and tits) often works in her yard in shorts and a tank top. I like to stand at the side window in my kitchen and jerk off while watching her. The window is a little over waist high so she can't actually see what I'm doing ... but she can see my upper body and face through the glass. I sometimes wave or lean out and speak with her while I'm stroking. It's difficult not to cum if I'm actually talking with her so mostly I just watch and stroke. Recently, she had a small party at her home to which I and most of the neighborhood were invited. I slipped away upstairs while no one was watching and spent a few blissful minutes rubbing my cock on various items of her clean lingerie ... which hopefully she later wore. Before leaving the room I went into her walk-in closet and shot my load into a pair of her sexy boots ... and saved a few dribbles for her high heels. Next time I plan to spurt my seed in her work shoes that she gardens with ... I'll then enjoy watching her from the window and jerking at the sight of her walking around in my dried cum.
It's all good!
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FrankB Skilled Jackinchatter

531 posts since 2015-11-14
35 year old heterosexual
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neilxt said:
I'm pretty good at this. My favorite place was my freshman math classroom in high school. Some of my friends dared me to do it, and were watching out for me while i did it in the back of the classroom. Maybe not the riskiest place I've done it, but definitely up there.


Mine is similar. I sat in the far back corner of computer class. Between the desks and the lights usually being off, the guy sitting next to me and I could jack off without anyone seeing what we were doing. Once we agreed which picture we were going to cum to and were both hard, I would unbutton and unzip my jeans so that the other guy had a clear view to see me gripping my cock and then shooting my load.
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CaptainKremmen Amateur Jackinchatter

248 posts since 2021-02-01
63 year old
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Curious1972 said:
When the weather outside is nice, my next door neighbor (50-something MILF with lovely legs, ass and tits) often works in her yard in shorts and a tank top. I like to stand at the side window in my kitchen and jerk off while watching her. The window is a little over waist high so she can't actually see what I'm doing ... but she can see my upper body and face through the glass. I sometimes wave or lean out and speak with her while I'm stroking. It's difficult not to cum if I'm actually talking with her so mostly I just watch and stroke. Recently, she had a small party at her home to which I and most of the neighborhood were invited. I slipped away upstairs while no one was watching and spent a few blissful minutes rubbing my cock on various items of her clean lingerie ... which hopefully she later wore. Before leaving the room I went into her walk-in closet and shot my load into a pair of her sexy boots ... and saved a few dribbles for her high heels. Next time I plan to spurt my seed in her work shoes that she gardens with ... I'll then enjoy watching her from the window and jerking at the sight of her walking around in my dried cum.


Sounds like a perfect relationship
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UlsterRob Professional Jackinchatter

1511 posts since 2021-06-03
61 year old curious male from Ulster County, NY
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Standing up on the shoreline of the Outer Banks in North Carolina facing the Atlantic ocean.

If anyone in Portugal happened to be looking west at the time, well, it could have gotten complicated.
PM me if you like messaging about masturbating!
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I tend to not want to go to jail, so not much "risky" for me
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CaptainKremmen Amateur Jackinchatter

248 posts since 2021-02-01
63 year old
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I keep going through this thread and reading
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Zeeguy Amateur Jackinchatter

118 posts since 2017-04-28
78 year old curious male from UK
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Love it, Ulster Rob!
ElderJacker
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Taboogramps Novice Jackinchatter

33 posts since 2023-07-26
73 year old curious male from East midlands
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Behind the sofa talking to my mother in law sitting in front of me
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swestxx Amateur Jackinchatter

226 posts since 2022-08-29
69 year old bisexual male from Forest Grove, Oregon
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My sleeping aunts bedside and other fam membs too.
MB for life!
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Grannylove Novice Jackinchatter

23 posts since 2023-09-13
70 year old bisexual male from Scotland
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Once whilst in the same bed as a person I used to stay with as a lad. I perfected the technique of silent wanking with minimal movement.

Another was in a church vestry whilst the warden showed me his wife's panties
Old wanker
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diddlealot Novice Jackinchatter

43 posts since 2016-02-07
56 year old curious female
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would love to watch
loves clits
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Gregm1970 Amateur Jackinchatter

452 posts since 2021-12-14
55 year old curious male from Yorkshire
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You can watch me x
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