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red99 Amateur Jackinchatter

434 posts since 2010-01-01
male from UK
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Scottydapimp187 said:
I had seen and compared penises with friends but discovered masturbating alone.
One day my best friend asked me if I jacked off. I wasn't sure what he meant at first. So he asked to do it, that was the first time I saw another guy stroke off and ejaculate, and me being uncircumcised and his was we had interesting different methods.


I had a friend a year older who started discussing and then decided to demonstrate one summers day. At that point I no idea what masturbating was and I don't think i'd ever seen someone else erect before either, so rather an abrupt introduction.
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joe1972 Novice Jackinchatter

5 posts since 2017-06-20
51 year old male from Northern Ireland
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I was in my late teens when i last jerked off with friends, but its still a turn on remembering those sessions
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Frotbuddy said:
My bud used to make jokes about circle jerking with me. I finally told him I'm ready whenever you are. We were watching porn so i said, let's quit talking about it and do this. I whipped out my dick and stroked. He watched and said he wasn't hard yet. Needless to say, he backed down and i came alone. Disappointing.


I'm ready when you are, wink
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Billyboxlad Amateur Jackinchatter

440 posts since 2020-01-16
curious male
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Had 3 mates at school and we all wanked together.
Helped too.
First mutual wank was with a cousin in a bath and a soapy wank.
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luvheels Skilled Jackinchatter

611 posts since 2007-03-16
59 year old heterosexual transgender female from Canada
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When i was a teenager my sister's friend's younger brother brought out a stash of Penthouse magazines and we looked at them together. I was too naive then to realize that he probably wanted to masturbate together to them but he was too scared to initiate it. At the time I was too hung up to join in even if he had taken his cock out and started stroking it but if I could go back in time, I'd be the one whipping my cock out and jerking it first.
No heel is too high
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ScottishWanka1990 Amateur Jackinchatter

269 posts since 2016-04-06
33 year old male
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I've been lucky enough to have stroked with a few mates over the years n its great if you both into same/ similar stuff! I'd recommend it for any guy to try it, nothing other than just stroking yourself needs to happen tho, just relax and enjoy the experience.
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Doug55 Skilled Jackinchatter

647 posts since 2017-05-22
59 year old homosexual male
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When you were a kid didn't you have
clubhouses with your friends that's
how you learnstroke
I am your bottom
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strokeme957 Novice Jackinchatter

24 posts since 2022-12-12
55 year old male
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Never have been yet. Still waiting...............
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ukwanker48 Amateur Jackinchatter

312 posts since 2007-04-26
65 year old curious male from UK
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Any sex, any age, if asked I will do it
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ukwankinglad Novice Jackinchatter

81 posts since 2022-06-05

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when I was uni my housemate and I used to wank off to a busty hottie on his course still wank over her pics now pm for chat cock
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ukwankinglad Novice Jackinchatter

81 posts since 2022-06-05

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.
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Vyvyan Novice Jackinchatter

57 posts since 2019-05-28
34 year old
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I met a girl at a party once, and as the drink flowed, the talk turned to our sexual experiences, and it turned out she'd never seen a guy jerk off before. So, I told her I'd show her, and we arranged to meet the following weekend. I didn't masturbate all week and was horny as hell when the day arrived. When she arrived, she had on a short dress, and her tits were busting out the top. I just had on shorts and a shirt, and started to gei hard while we talked. She could see my growing boner and smiled at me as the tip started to stick out my shorts. I got up to get our drinks and figured since I'd soon be masturbating why not get naked, so I did. When I returned, my penis was sticking out and she reached out, cupped my balls, squeezed them and said they felt heavy and full. I said not for long. I stepped back and started stroking my cock. She was staring at it, and I could tell she liked it. I stroked slowly, stopping to let her watch my penis throb. It wasn't long before the precum started to flow and I used that as I lube as I stroked. I stroked it, then held my hand still and thrust my cock in and out, fucking it. The masturbation was so hot and I was so turned on, and I knew I had to cum, so I let it fly. I'd never cum so hard in my life, and the first spurt hit her, so I stepped back and shot loads of cum. It felt like it wouldn't ever stop, but it did.

I went to get a towel to clean up, and when I got back she was naked, since she got cum on her dress and wanted to clean it off. After cleaning up, we sat on the sofa and talked. I started to get hard again, and started jerking off. She let me play with her tits while I masturbated, and it wasn't long before I shot another load.

We had another drink and I decided to show her around. We walked around naked and my dick was semi hard. When we got to the bedroom, she stopped in the door way and my dick rubbed up against her. She started to rub her ass up and down against it, and I soon had a throbbing boner. I wanted to fuck her, but she tonight was my night of masturbation, so we'd do that another night. But, she would lay on the bed and let me rub my penis between her ass cheeks and I could rub it between her breasts too. So I did that. My penis was really getting hard as I rubbed it on her ass. Then she turned over and grabbed my penis and put it between her big breasts, squeezed them around it and I fucked them. I then pulled it out and started masturbating my throbbing cock. I did that as long as I could and my cock was so hard and throbbing so much and my balls were so tight against me, that I decided to show her a hands free cum. So I squeezed my penis as hard as I could and soon the cum was shooting out and I ejaculated another big load all over her.

That was one great night of masturbation, and I think I came 4 or 5 times. That wasn't the last time I masturbated for her either.
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pietsmith Amateur Jackinchatter

256 posts since 2020-06-15
55 year old curious male from Germany
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Wow. Very hot story. cock

Vyvyan said:
I met a girl at a party once, and as the drink
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My friend at school had an older sister who's boyfriend invited me to such things.
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jobuddy10 Skilled Jackinchatter

575 posts since 2012-01-26
52 year old curious male from SW Ohio
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haven't been asked since HS...
Luv all shapes and sizes
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