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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
31 year old curious male from USA
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A lot of us here have a close male friend who we are able to hang out with and talk sports or life over a beer or plan a secluded fishing trip together. Society doesn't think much of those types of close male friendships. I wish it were more common and acceptable for men to have those types of close friendships but with the focus being masturbating together.

We pretty much all grew up with this intense taboo surrounding masturbating: you never discuss it. You do it alone and in private. There's a culture of shame around the idea of it. Yet you know that you do it, your best friend does it, your coworker does it; if anything it is the one thing all men have in common, yet none of us are open about it. I wish something like "I love to masturbate! Oh, you do too? Nice! We should hang out sometime. What do you enjoy jerking to?" Was a more common conversation between close male friends. We talk about how men struggle with emotional expression and intimacy, but having those kinds of friends would allow many of us to fill an intimate void we all lack.

I would love make an online friend who understands where I'm coming from.

I also love the dynamic of masturbating with an older man. I am 28, and the dynamic is very erotic. I am not sure if its the idea of having a mentor, or the concept of him being a kind of father figure, but its very sexy to bond with older men over our love of masturbation.

Feel free to message me on my Skype at syntheticdreams2077 Messaging me there referencing the title of this post so I know where you added me from.
Skype: syntheticdreams2077
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blackjackx89 Skilled Jackinchatter

651 posts since 2013-03-24
34 year old heterosexual male from Texas
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I get where you're coming from (heh). I think a lot of us on here do. One of my oldest regular online jerk off buddies is an older guy (about 30 year gap between us). We talk about stuff between trading pics or he'll hear me out when I need to vent about stupid stuff that day.

Our conversations about models and porn stars are pretty casual and can even go on for a while. Sometimes I get a notification and he's sent a pic or two like a little "thought of you/thought you might like this" thing.

He might not know it, but I appreciate being able to chat with him, lust over babes and jerk off together online. In the years I've spent doing this, I've found that there's not many people who are sociable -just cum and go- and I only have a few in my social circle who I click with.
DM for Discord & Skype contact info
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Very thoughtful and thought provoking. I wonder if society has ever allowed men to be open about masterbation
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joet Amateur Jackinchatter

248 posts since 2013-02-05
59 year old curious from US-New Hampshire
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back in High school, my best friend and I always jerked off together. I think if we didn't live on each side of the country, we would still get together once on a while and do it. Would love to find a buddy to do it with once in awhile now. Don't have a friend, that I would like to do it with now, but alwas looking
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SyntheticDreams said:
I also love the dynamic of masturbating with an older man. I am 28, and the dynamic is very erotic. I am not sure if its the idea of having a mentor, or the concept of him being a kind of father figure, but its very sexy to bond with older men over our love of masturbation.

I agree completely. I feel the same way but I'm coming from the other side being nearly 50. I enjoy stroking online with younger guys who are surprised at how open I am about what gets me off and I encourage them to do the same. I wish I had someone like me 25 years ago! wink
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LuvShavedCuntUK22 Novice Jackinchatter

30 posts since 2019-07-15
27 year old bisexual male from Cardiff UK
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I love having a long wank session with an older man. Love the age gap.
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hotbellend Novice Jackinchatter

5 posts since 2019-07-28

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Totally agree! I had a fairly longterm online wank mate who was quite a lot older than me. We could chat really openly about anything and he taught me lots of stuff like edging. Basically ended up being a kind of naughty mentor for me.
I definitely had some of my horniest ever wanks with him and would love to have some more chat like that!
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I used to have a 65 year old fuck buddy,we've had great sex,mainly in the woods,he would finger my ass,whilst wanking me off oh blimey the fun we had,aw I loved it,older is so sexy it gets my blood racing I find it a turn on knowing an older man wants to please me.
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hotbellend Novice Jackinchatter

5 posts since 2019-07-28

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Shak1999 said:
I used to have a 65 year old fuck buddy,we've had great sex,mainly in the woods,he would finger my ass,whilst wanking me off oh blimey the fun we had,aw I loved it,older is so sexy it gets my blood racing I find it a turn on knowing an older man wants to please me.

Wow, I'm going to have to hang out in the woods some more!
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hotbellend said:
Wow, I'm going to have to hang out in the woods some more!


Oh you should,The chap who used finger and fuck me me,used to get quite nervous,but I'd get my kit off and stand naked in front of him touching myself whilst I'd rub his cock through his Jean's,I dont care who saw me.Oh the sun and breeze on my naked body it felt wonderful.Cant wait for the summer
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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
31 year old curious male from USA
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Thank you for all the well thought out responses. I love masturbating with others. It really is a bond like no other. We all do it but are never able to discuss it in real life with our actual friends. I feel that there are two types of men in life for those of us here: actual friends, and jerk buddies. I really long for someone who bridges the gap between the two. Someone I can masturbate with but also talk with, confide in, and really share that special connection with rather than a quick run and cum. Not that those aren't fun, but they are often short lived and leave you feeling empty longing for more.
Skype: syntheticdreams2077
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contourpouch Amateur Jackinchatter

255 posts since 2014-12-30

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Agreed. In my teens I had a close friend that I felt a natural urge to masturbate with, but as a straight guy felt guilty at the thought. That is probably what stopped both of us masturbating together as chatting about it was hot - but embarrassing - when the subject came up.

Over the years I tried to come to terms with it, especially as the need returns with age. I now know that ancient Greeks seemed to understand that this kind of male-bonding relationship was natural (besides functioning as a sexual outlet when wives/gfs aren't in the mood).

The older/younger dynamic has occurred to me when at the gym when getting involuntary erections around younger 20+ studs.
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When I was younger I had a special much older friend that taught me how to enjoy my favorite toy. It was a great experience and it went on for quite a while. Now that I am older I would encourage younger guys to go for it! If you get the opportunity go for it. If you don't see any opportunity at this time, do what you can to seek out a more mature jerk buddy and enjoy life while you can. Mutual masturbation can be a great experience, enjoy it.
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SyntheticDreams Amateur Jackinchatter

279 posts since 2019-07-28
31 year old curious male from USA
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I am really happy to see others understanding what I mean. the age difference is hot but more importantly is the bond, the ability to feel comfortable naturally opening up, sharing, being intimate and vulnerable. Especially when society encourages men to be super masculine and stoic.
Skype: syntheticdreams2077
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JObud4U2 said:
When I was younger I had a special much older friend that taught me how to enjoy my favorite toy. It was a great experience and it went on for quite a while. Now that I am older I would encourage younger guys to go for it! If you get the opportunity go for it. If you don't see any opportunity at this time, do what you can to seek out a more mature jerk buddy and enjoy life while you can. Mutual masturbation can be a great experience, enjoy it.


Oh yeah, forgot to mention that I would be available to help anyone that is a bit timid........ strokestrokestroke
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