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legasslover Professional Jackinchatter

2350 posts since 2018-06-28
male
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Myself, a school friend and a Kylie Minogue poster. We both fucking exploded.
Feel free to PM me for a chat or my Skype/Wickr details.
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JObuddyIA Skilled Jackinchatter

846 posts since 2008-05-23
73 year old homosexual from Keokuk Iowa, USA
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As I read these, I'm getting the picture that about everybody around me, was doing it. Why the heck didn't you or somebody invite me in on the explorations?
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Jay Amateur Jackinchatter

106 posts since 2005-09-11
heterosexual from Toronto
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I was around 13 years old. It was with a friend, I went over to his house his parents went out. We talking about sex and asked me if I had masturbated. He asked me if he could masturbate and I could join in. I watched him for a bit i started to get hard and horny so I joined in. We both got naked and rubbing against the bed, watching him masturbate made me cum hard after.
Masturbation is hot!
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Mine was with a much older guy. My parents never really understood why I started enjoying my piano lessons more all of a sudden!
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Harrycarrot Novice Jackinchatter

53 posts since 2019-11-25
70 year old bisexual male from Leeds Yorkshire England UK
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My best mate when we were camping. Both 13 and during the night dared each other to show our cocks. Then dared each other to touch cocks together and ended up wanking each other off.
Harry Leeds England
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idaway01 Novice Jackinchatter

58 posts since 2019-04-15
45 year old curious male from EU
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I was 13 and it was not too long after I began jerking at all. Me and my best mate from school (he was very close to my age) started out just doing it while together in his bedroom on sleepovers. At first it was even under the covers. But we soon got curious and started touching, watching, jerking and sucking each other. Never went beyond that btw. We had so many good times in that period. A mutual friend soon joined us often. He was our age but more developed than us. He started my fascination with cum I think. He shot huge loads over long distances. His spurts often plastered even the ceiling. I havent had a JB as an adult but I still dream of reliving some of those memories.
Open-minded, curious, always chatty. Love to listen and have lots to tell.
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jockstrapluver Novice Jackinchatter

9 posts since 2016-01-25
58 year old bisexual
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First time with someone elsefor me was a sleep over in 4th grade. He was more developed than me and when changed into our pj's I noticed his dick was much bigger than mine. I remember saying your pecker is bigger than mine. He said I can make it bigger and started rubbing himself. I had rubbed my pens against my bed and came dry before but watching his cock grow while he was touching it was amazing. I grabbed mine and started beating off too. I came dry but he squirted a little cum. Let's just say I always asked to have a sleep over with him. We played with each other until we went to different middle schools. Married and 25 years later, I still beat off thinking about my buddy.
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jockstrapluver Novice Jackinchatter

9 posts since 2016-01-25
58 year old bisexual
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jockstrapluver said:
First time with someone elsefor me was a sleep over in 4th grade. He was more developed than me and when changed into our pj's I noticed his dick was much bigger than mine. I remember saying your pecker is bigger than mine. He said I can make it bigger and started rubbing himself. I had rubbed my pens against my bed and came dry before but watching his cock grow while he was touching it was amazing. I grabbed mine and started beating off too. I came dry but he squirted a little cum. Let's just say I always asked to have a sleep over with him. We played with each other until we went to different middle schools. Married and 25 years later, I still beat off thinking about my buddy.
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Rod Enlightened Jackinchatter

3032 posts since 2005-08-13
53 year old bisexual from Dallas, TX
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Overdue with this reminder:

This is the kind of thread that walks a fine line between the Terms of Service and the spirit of the site. Tread carefully...yes, most of you are discussing your personal experiences, but since most of those experiences were when you were underage, the thread may be closed at any time.
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MaxG said:
Further to this we met today and shared some beers in a neutral place (my works office which is unmanned this weekend). He looked older than I remember and has some health problems and smokes like a chimney, which I have given up. We spent two beers talking about work and friends then during the third I mentioned our porn-sharing past. Had a fairly relaxed conversation but didn't push the situation. I'm not sure he is as open-minded as me but could be wrong. Why didn't I ask him? Good question. Seemed wrong straight off the bat but foundations are laid for more probing and another meet up. And as we did talk about jerking I think it was a small success. Just this openness pleases me no end as I am loosening age-old shackles I feel. Thanks for reading so far!


Update: I am hopeful of a meetup tomorrow night in the quiet site office I am looking after, for more beers and chat. My old collection of (nearly vintage) Mayfair and Men Only mags will be in a drawer a few inches from us as we chat. And the ancient PC will be whirring away, one click away from a large collection of softcore girlie Jpegs. If all things are cool I may open said drawer and see if my buddy remembers any of the mags. Things may progress from there; who knows!

I'm currently sitting here getting hard in my pants thinking about it. Would be so nice if he had the same idea and we both jerked off a load whilst talking about women. That's all I'm after for now, a respectful distance but keeping an eye on the others hard meat as it swells and throbs...
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brisjkr Amateur Jackinchatter

297 posts since 2006-04-29
66 year old male from Brisbane, Australia
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Billy22UK said:
Mine was with a much older guy. My parents never really understood why I started enjoying my piano lessons more all of a sudden!


You had a far better piano teacher than me.
I met my much older wank buddy while practicing my tennis skills
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SlaveofV Novice Jackinchatter

7 posts since 2020-12-27
47 year old
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with a friend I grew up with when I was in 6th or 7th grade. He would spend the night and we'd watch "skinemax" after midnight. The first time was after watching Emmanuelle IV.
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I had a couple of occasions with a buddy back in 7th grade where we would watch some good old dial up porn and jack ourselves very discreetly in our gym shorts, but we never touched or saw one another.

My first REAL mutual jacking was with a guy from CL-I was out of town for a wedding and his wife was out of town. I went over to his place and we got nude, watched each other stroke and then began jacking each other. I was 24 and he was 52. It was very hot and I loved every second of it. I was to nervous to suck him, but I wish that I had, knowing how much fun that is now.
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NeedJObud Novice Jackinchatter

3 posts since 2013-12-04
64 year old homosexual male from Sacramento, California
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There were some occasions where I nervously and awkwardly got someone to jack with me (not always all the way), but the first time it was totally premeditated was with a slightly older friend. I can't remember how we'd gotten onto the subject, but somehow or other we started talking about jacking off and how we both enjoyed doing it. We didn't immediately jump into it at that point, though. Somehow or other we decided that we'd go to his house one day and do it together. Unfortunately, not long after we started his sister came home and we had to stop. I wanted to find some secluded place outside to finish up, but he wasn't comfortable, so there were no cumshots together that day.

But shortly after we decided to try again, this time at my house. We went out into the garage but before we got started he had to pee (I learned later that he usually liked to go right before). We were already out there and didn't want to arouse suspicion by going back into the house and then right back into the garage again, so I picked up some empty container that was out there and held it for him. (It wasn't and isn't really my kink, but I'm mentioning it here because it really did happen and I know some will enjoy it.)

Anyway, after that we wound up kneeling on the cold cement garage floor, pulled our dicks out and just started stroking them at the same time. I don't know if he was watching me, but I was definitely watching him! I was a bit nervous about the whole thing, but after a few minutes I knew it was definitely going to be possible for me to cum. But I really wanted him to do it first, probably because for some reason I was afraid that I'd shoot, then he'd just stop and I'd feel weird being the only one.

So we kept at it and suddenly out of nowhere he quietly began to cum on the floor. Not a huge load, but definitely hot to watch. I'd been holding back for a while, so once I saw that I just let mine go as well. We kinda smeared our loads together onto the floor with our shoes and figured they'd dry out soon enough.

Later he asked if I'd cum! I guess he wasn't paying attention.

We did it together several times after that, though I think it was always in a situation where we couldn't see each other shoot. I remember one time outside at night (I could hear his stroking slow down and asked if he was cumming...he said he was, so again I took that as my cue to shoot my own load), another time where he was in the bathroom and I was on my bed and yet another time where we were both in my room but the light was off. I don't know why I was so shy that time--he actually wanted the light on, but for some reason I felt weird about it. That was also the only time we used any kind of lube in front of each other, specifically hand lotion. Again, I knew he was spurting when I heard him slow down, but again I asked just to be sure before letting my own shoot out. He came on my bed! Oh well.
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Getting closer and closer to a jerk session with a bud. Met three times now to chat, drink beer, talk shit and look at naked women. First two times I hinted that I was going to have to bash one out after our meeting, hinting all the while that I'm pretty horny and giving room for it to be a bit jokey to set the mood.
This evening we met for the third time and halfway in, the conversations actually turned (his choice) to previous or teen masturbation encounters. He had done stuff, I actually haven't.

I was actually taken aback at this point, thinking that I have been too delicate the last two meetings, even though we meet up to look at porn and talk sex, lol!

I took the opportunity to ask if he would feel awkward if I 'had a little stroke' in his presence. He was cool about it but said he was okay for now in not joining in. So I got almost all the way there and I've got to say it felt fucking awesome, totally relaxed and cool. The room was fairly dimly lit and I was in an arm chair so he could view as little or as much as he wanted.
Like I said we seem to be ratcheting it up in stages so he left as usual but not before I think he glimpsed my erect penis as we said goodnight. This time I beat it out leisurely to a lovely sticky climax and messaged him afterwords, showing him the picture I came over. This has me convinced we will jerk together soon...
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