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Barefoot Amateur Jackinchatter

152 posts since 2005-08-27
41 year old curious from Wales, UK
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To this day I still think my very first orgasm was the best. I was 13, lying on my bed after a shower and just enjoying the sensation of playing with my cock. I wasn't trying to achieve anything, but it just kept feeling better and better. Suddenly I tipped myself over the edge into orgasm (although I didn't cum) and it truly blew my mind.

Coming in a close second was the first time I came without touching my dick; just lying in bed fantasising about sex. That was pretty awesome as well! grin
"Going barefoot feels like secretly going naked in public."
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ineedabeer Novice Jackinchatter

38 posts since 2008-08-16
56 year old curious from Australia
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I masturbated the other day in a department store change room,i had not done that for years.I came so good with heaps of cum.i came on the pants i was trying on so i had to put them back on the rack and get a new pair.
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ja_ja Novice Jackinchatter

25 posts since 2008-10-28
47 year old from chennai, India
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My best orgasm was when I masturbated peeking into women nude bath in the beech .. the effect of masturbating watching live flesh was too much!
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I was having personal problems this summer and for a few months (as incredible as this is to believe), masturbation wasn't on my mind.
After sorting things out, I was in the shower one day and suddenly had the urge to jack off. I became hard as fuck and began pumping furiously. Eventually it became clear I was finally going to have an orgasm and it literally dropped me like a rock. Blood rushed through my body and I shot many giant loads of cum all over the drain while lying on my knees. I normally don't make sounds while cumming but this time I nearly screamed.
I knelt there for a few minutes afterward, still shaking.
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Had some uniquely powerful orgasms and I like it when I can resume stroking shortly after my first - and then have a second orgasm. But my most memorable were the first time I had an orgasm and ejaculated and my first intercourse orgasm. I still remember both very well. Seeing cum shoot out of my cock that first time was pretty amazing and a very memorable experience.
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winger89 Amateur Jackinchatter

327 posts since 2010-02-19
54 year old bisexual from Sacramento, CA
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ineedabeer said:
I masturbated the other day in a department store change room,i had not done that for years.I came so good with heaps of cum.i came on the pants i was trying on so i had to put them back on the rack and get a new pair.


That must have been interesting when found....
Jerkin daily since 19......
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pantystroker Novice Jackinchatter

69 posts since 2010-03-09
60 year old bisexual from Wisconsin, USA
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I would have to say probably back when I was in high school. Probably 15 or 16. There was a girl in my class that I was really hot for, but didn't have the courage to ask out. She had the cutest ass and it was the subject of many of my orgasms including the best one I've ever had.

To comment on current day, I have to agree with Dimpled about rubbing your cock in a woman's ass crack. As you can probably tell, I'm a butt man and my GF will indulge me every now and then by letting me do this. She doesn't seem to get much out of it, but she knows its one of my favorite bedroom activities.
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Earlybird Amateur Jackinchatter

347 posts since 2011-07-10
heterosexual male
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My most intense & longest-lasting orgasm was most definitely my first dry orgasm when I was a kid. The feelings were so intense, I almost passed out!

I discovered masturbation & dry orgasms by accident just after my 5th birthday. I had been getting erections for about a year, but didn't know what they were or why I got them. I was in my bedroom after a bath, and noticed that it was really hard, and felt sort of tingly. I decided to touch it. That felt really good, so I touched it some more. That felt really, really good. I instinctively started rubbing lightly on the sweet spot below the head. Within seconds, the good feelings built to such an intensity that I couldn't handle it. So I stopped rubbing. But the feelings kept getting stronger & stronger. My penis started bobbing up and down in time with these strange and extremely intense new feelings. My body started to shake uncontrollably. I had no idea what was happening. All of a sudden, the feelings exploded with such intensity that I screamed and nearly fell off the bed. The feelings were so intense that I nearly passed out. I had no idea what had just happened to me, but I knew that I wanted to feel this new, unbelievably intense and wonderful feeling again right away! I was worried that it might be a one-time thing, so I started rubbing again. Within seconds, I felt the strange feelings building up. Again, they got so intense that I could hardly stand it. But this time I kept rubbing. A few seconds later, the feelings exploded through my body. I kept on rubbing, and the feelings peaked over & over again for what seemed like a couple of minutes. The feelings were so unbelievably intense, yet so unbelievably wonderful. I was very happy to learn that it wasn't a one-time thing, and was amazed that I could make myself feel such wonderful feelings. And I did so at every opportunity! razz
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denali7155 Skilled Jackinchatter

798 posts since 2011-09-13
61 year old heterosexual from USA
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Swimming pool jets hitting the under side of my cock as I look at babes in bikinis. This started in my very early teens and continues to this day. I love having orgasms in public from these pool jets and no one knows. Very intense orgasms.[img]null[/img]
I like to share my jo materials.
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Shvdmale Skilled Jackinchatter

689 posts since 2015-12-15
72 year old bisexual male from Texas
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My best was when I was hands free fucking my Fleshlight with my aneros up my ass hitting the right spot! I came so hard I nearly passed out!
Always naked and horny...STILL looking for JO bud.
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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My wife, who was my girlfriend at the time, tapped into my foot fetish almost immediately. She slipped into a pair of red suede heels, white thigh high stockings and a string of pearls -- nothing else -- and joined me in bed.

We fooled around for a while, then she spun around as if she wanted to 69 with her on top. But she moved down further. She slipped off one of her heels and slid it onto my hard cock, where I could feel how warm and humid it was. She kicked off her other shoe, so it would be near my face. I picked it up and inhaled her femininity.

She placed one of her feet at face level, where I could see the red nail polish through the white nylon, and told me to suck her toes. That was something I had done before, but up to that point it was something I initiated. It was the first time she wanted it done. (It wasn't the last time, either.) As I slipped her pretty toes into my mouth, she started jerking me off into her shoe.

I blew a huge load almost immediately. She simply took the shoe and put her foot back inside it, cum and all, and masturbating with the string of pearls wrapped around her fingers.

My second orgasm coincided with hers. It wasn't as good as the first one, but still pretty impressive, considering I had just shot a load five minutes earlier. Ah, to be 23 again.

That first one ... my best ever. I'll never forget it.
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I was about 17 and spent about 8 days at an event at a college. We were shacked up 3 to a dorm room with zero privacy the whole time. I got home at about midnight and luckily there was one of those softcore porn movies on HBO. I came and came and came. I am willing to bet 10 ropes. The t shirt i used to clean up was soaked.

Second, i would say was the morning after my wedding. I partied pretty hard the night before and am ridiculously horny when hung over. I pumped rope after rope into my wifes beautifully smooth pussy. We were both shaking from the intensity.

Third, I had a girlfriend in college that would literally do anything and came at the drop of a hat. I fingered her, she came hard. I ate her out, came hard again. Went balls deep in her pussy and grinded for a minute, came like a mad woman. Finally, i grabbed some lube and went directly for her ass. Unloaded inside her while she's shaking from another orgasm. Too bad she was so annnoying and needy that I broke up with her shortly after. Haven't had anal since.....sigh.

Fourth, curiosity got the best of me and I fired up my shop vac and stuck my rager in the hose. Holy shit, the rapid fluttering had me cumming in seconds. My knees gave out.

Fifth, i had seen some e-stim vids and have a TENS unit. I strapped on two probes, one on my taint and the other on my shaft. Played with the settings and found what felt best. I shot a crazy hands free load.
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donhagen Amateur Jackinchatter

229 posts since 2012-07-04
46 year old curious male
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best orgasms from masturbation involve people i know. first was a friend in the late 90's who emailed me her nudes unprompted just because she wanted to cheer me up. nothing compared to it. got so hard and beat off all day to it. this was before digital cameras were common. so they were scans of pics she had taken and had developed. a friend at the local photo place would develop them for her, as nudes were against the rules. a year or so later she showed me in person her entire photo album of nudes. and i couldn't wait to leave and go jack off.

the second time was a woman i had been chatting with over yahoo around 2000-2001. we were planning to meet and hang out but sex never came up. then one night she flat out asked if we could trade nudes. i was cautious at first but then i was like, i get to see her naked, so what the hell. we traded a couple more times and masturbated together over chat and phone but never got to fuck in real life. i still have the nudes saved. when she's looking sexy in a facebook post sometimes i will pull up her old nudes and jack off to her.

the third is the magical finding random nudes of someone you know. a high school classmate cheated on her husband, and he leaked her nudes (around 2005 i think) which made their way to more than one of the sites i used to frequent for porn. i'm not normally really into that, stolen pics, revenge porn, and the like. but when i saw who it was, my heart raced, and when i beat off i came so fast.

i've had bigger, better orgasms from sex, but as far as beating off, nothing tops those moments for me.
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FLscribe Professional Jackinchatter

1988 posts since 2014-06-09
55 year old bisexual male from tampa
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donhagen said:
the third is the magical finding random nudes of someone you know.


No doubt about that. I stumbled across a photo of a coworker once, someone I had been quietly lusting after. Classic MILF, about eight years older than me. If it wasn't her, it was her exact clone -- down to the birthmark on her shoulder. Needless to say, I jerked a big load that night.
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donhagen Amateur Jackinchatter

229 posts since 2012-07-04
46 year old curious male
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FLscribe said:
No doubt about that. I stumbled across a photo of a coworker once, someone I had been quietly lusting after. Classic MILF, about eight years older than me. If it wasn't her, it was her exact clone -- down to the birthmark on her shoulder. Needless to say, I jerked a big load that night.


and what's cool about it is if someone else saw random nudes of any of these people it wouldn't mean as much. i hope to see some more someday, though at this age it gets more unlikely.
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