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It was 4 of my neighborhood friends when I was 11.
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my aunt when i was 9
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hotdoggin Amateur Jackinchatter

119 posts since 2013-01-25
48 year old heterosexual from colorado springs
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i was 13 and and the girl in the downstairs apartment was 12, she wanted to see my dick so i let her see it, then i asked if i could see her pussy, so she pulled her panties aside and flashed it at me (i was hard as a rock at that moment! the next day she and i flashed again, so i asked her if she wanted to see how it worked, so i tugged and shot a wad for her and let her touch the tip while the cum hung from the tip. since then for about 4 months, she would let me fuck her ass cheeks (assjob) and cum on her butt while she played with herself. we never did actually have sex. i miss those perverted days. shes what got me interested in asses and cum on ass vids! she moved away that summer
its all good till she gets it in the eye!
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stickywicket Novice Jackinchatter

76 posts since 2015-03-30
53 year old
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A guy when i was a lad
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biker061 Amateur Jackinchatter

301 posts since 2016-01-06
69 year old heterosexual male from Oklahoma
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when i was 10 my family shared a large house with my aunt/uncle & family. three cousins, 2 male (15 & 12) one female (13). we used to play all sorts of fantasy/rescue game. many, nearly all of which involved being nude and masturbating together. lasted about a year or so.
"...occupational hazard is, occupation's just not around..."
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boot911 Novice Jackinchatter

13 posts since 2016-06-21
39 year old bisexual from UK
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It was quite some time in to my sexual life when somebody first saw me masturbate (at least, for real). It was a hot night with a sexy TS, obviously there were other things that happened but we jacked off and came over each other many times. It was hot.
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N/A
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Comus Amateur Jackinchatter

173 posts since 2010-12-10
55 year old
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The first person to walk into the room and work out what I was doing, even though he could not see anything, was my dad. That was really early on, possibly while I was still gettting dry orgasms.

The first person to see my actually stroking my cock and watch me cum was, I think, a younger scout at a scout "patrol camp". The others were alseep and he asked me when I had last cum. I said "last night" and then he wanted to know when I next expected to cum so I said "whenever I feel like it". He seemed really surprised at that. It seems he knew about wet dreams, and knew you didn't choose when to have them, but didn't know about masturbating. I explained how it worked and he wanted a demo so I gave him one.
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My mom walked in on me when I was 12.
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Middle-aged neighbour caught my on my parents patio. She didn't seem to mind.
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backdoor_man034 Skilled Jackinchatter

751 posts since 2013-11-23
55 year old heterosexual from Kentucky
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My buddy in high school. We used to jack off together a lot.
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No-one has ever seen me masturbating for real.

But otherwise I like to have people watch me on cam. Really enjoyed that but haven't done it for a while. Would be good to find some new contacts. I tend to orgasm quite quickly and I am very small.
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Young20 Professional Jackinchatter

1328 posts since 2015-06-23
28 year old bisexual male
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My tent-mate, Bill at scout camp. I was sitting on the cot working one out when he walked in on me. HE said, "Oh, you do that too?" and left me to cum. THat night we talked about it and JO'd together.
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lovetostrokemycock Novice Jackinchatter

42 posts since 2013-10-14
48 year old
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My buddy and I would jerk together before we could shoot. His little sister came in one day and caught us. She laughed and said put those things away will ya..
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captjack Novice Jackinchatter

32 posts since 2016-06-28
bisexual male from Texas
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My best friend Richard M...he lived in the country and I spent week-ends with him...we played with out cocks..old enough to get a hard on yet too young to cum..at that time...it went on until I left home for the life of a sailor...good times for sure...captjack
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