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Fun With Personal For J/O Buddy

Posted by: Age: 40's and beyond Posted on: 6 comments
11 likes 156 views Category: Masturbation Male-Female Tags: Masturbation Male-Female, male-female, male-male, bi-curious, mutal masturbation, jacking off, jackoff club, sharing fantasies

My female friend encouraged me to explore my male-male fantasies and have an encounter with other men to jack off and more.


I have a close female friend and sexual confidante.  She is non-judgmental, sexually adventurous, and open to talking about anything.  These factors, combined with a smoking hot body, makes her sexy as hell.  Over time we have shared many of our deepest fantasies and both get turned on and masturbate hearing and responding to each other's fantasies.  Because of our circumstances (both married) many of our exchanges have been via email (with photos) or hot chat sessions, with infrequent time together.  We both love to masturbate and, although we have shared a lot about it in writing, we have only been able to do it a few times together (or via phone sex), along with other things I won't mention here.  When I am alone, she is one of the women I fantasize about the most, and I always cum when stroking my cock looking at some of the sexy photos I have of her (but I digress …) Among the fantasies I shared with her were those that included doing things with men, which I found to be very liberating since I had never shared these bi-curious fantasies with anyone.  Through discussions and encouragement from her, I began to want to explore some of them for real.  I had already discovered the sleazy, kinky pleasure of privately jacking off in adult book stores/video arcades in the midst of anonymous men, but had not progressed to interacting with any of these men for mutual cock play (which I would do later in adult book stores and a porn theater). One of my fantasies I shared with her was about going to a jackoff club.  This appealed to me because it would be such a rush and turn-on to jerk off in public while watching, and being watched by, other men doing the same thing.  This jackoff club fantasy evolved to include engaging in mutual cock play/handjobs with other men watching (so hot!)  As I began to entertain the idea of actually going to a jackoff club, I thought if I liked the experience, maybe I would try finding a buddy for more personal J/O sessions, eliminating some of the hesitation that goes along with unknown men in public places.  I told her I thought It would be fun to have a married buddy who I could get together with when we both wanted some cock play, even more fun if his wife knew about it and wanted to watch (or if my friend was there to watch me jack off/interact with another man.) After I told her about these jackoff clubs, she liked to browse through the message board of the local club to see the kinds of hot things guys said to each other.  She told me while reading the boards that she got the idea that I should post a personal message in the "men-seeking-men" section and see what kind of response I get.  She said that she noticed that personals from married men or guys with girlfriends got good responses, and that when she thought of my encounter with other guys, it was with married men who were content with their spouses and just looking to satisfy a curiosity; they would not be gay men, or men who had numerous same sex encounters.  She thought that if I did connect with other men, ideally the conversation need not be anything forced, just a few relaxed guys sharing a few drinks and laughs that eventually ends up with us showing off our cocks and then some. She encouraged me to try to find such a man (or men) by posting a personal ("an enticing one", as she put it) on the jackoff club message board.  She said to let her know if I wanted to have some fun with this and that she was very interested in reading the responses and might post some hot responses of her own! So with her encouragement, I drafted the following to be posted, which I shared with her: "Looking for a male friend interested in watching porn, jerking off, and more.  I like straight porn, but my special interest is same sex couples.  I also enjoy watching videos of guys jacking off, giving hand jobs, and sucking cock.  I love women but am curious and looking to experience the pleasure of male company.  I would like to hook up with other straight guys for jackoff sessions, mutual stroking, and sucking.  A big dick is not a requirement, but is strongly desired.  Age is not important, but I would prefer men who are mature and comfortable with their sexuality, but not aggressive.  On the other hand, if you are 18-25, have a nice athletic body with a big dick, and can reward me with multiple loads of hot cum, please step to the front of the line.  Other curious first timers would be welcome.  A hot young couple willing to explore and try all combinations imaginable, with me and him or me and her, while the other watches or joins in would be great.  My deepest desire is to engage in the above pleasures while others watch.  With an appreciative audience of men or women, I would like to suck off a guy or guys, and then stroke off for the crowd." I really had fun putting that post together, and of course I had to jack off while writing it and a few times later just reading it because it was so hot seeing my fantasy in words and thinking about other people reading and responding to it.  However, before I posted I decided to reel it in a little, so this is what I actually posted: "Straight married guy interested in stroking a dick for the first time. I fantasize about other straight married guys, preferably first timers to share porn and slowly satisfy our curiosity.  I would like to try mutual stroking and jacking until we shoot our loads.  If I feel comfortable and really get into it, I would like to try sucking cock also.  I would really get off sucking cock while being watched by an uninvolved female or male friend (as they get themselves off.)  Once going this far, my fantasy is to suck off the male friend until he cums, or at least let him jack off on me if he doesn't want involvement.  I have a female friend who would like to watch me have an encounter with a guy, which would be a turn-on for both of us." After I posted, there were many responses from a wide variety of men, sharing the sizes of their cocks, a similar desire to play with another married man, and/or the desire to interact while my friend watched. She liked to read the responses that I received from time to time, and told me there were some rather interesting and inviting responses to my posting but that I should be selective with who to get together with.  She then shared the ones that sparked her interest (basically married men who said they had no/limited male-male experience, but who were curious) and suggested that it would be good to exchange pics and have a private email exchange to get a little more info on them to help decide with whom (and if) I wanted to have this encounter.  She also surprised me by suggesting that I should I have this encounter with two other men. In the meantime, I had my first experience jacking off for another man and engaging in mutual cock play in an adult video store booth (see my story Video Booth Jerkoff Fun).  I had an intense orgasm and couldn't wait to tell her about my experience including how I played with a guy's cock the first time (and how I found I wanted him to cum on me).  Once alone in the booth with this man, I was surprised that I wasn't nervous and couldn't wait for him to pull out his cock so I could touch/stroke it.  This proved to me that I could interact with another man (and enjoy it!) and it let her know that I could take it beyond the fantasy world.  (At first I was really turned-on just by sharing my same-sex fantasies with her, and telling her about jacking off or anything that I did with another man.  Now, even though I would not hesitate to tell her anything, I find that I can enjoy these same-sex encounters (the few that I have) just for the kinky, taboo, pleasurable feelings I get from mutual cock play and/or jacking off with or around another man, or men.)  She wanted to know all the details of my experience, particularly what was going through my mind and how it felt.  She told me that hearing about it and reading the details (over and over) caused her to get wet leading to multiple pussy rubbing sessions and orgasms. She shared with me via an email exchange her vision of the whole scenario if I decided to go through with the more personal encounter.  She envisioned this taking place somewhere semi-private.  A place where I (we) were not totally alone with these guys and could pick up and leave at any point.  Some place dimly light, with comfortable couches, and a few drinks.  We (the guys) would be seated in somewhat of a circle facing each other.  She would like to be seated on a bar stool sort of looking on and enjoying a drink of her own.  We would talk about what turns us on or even about what we were about to do then eventually pull out our cocks, which would be soft at first.  She would like to see us begin by stroking our own cocks and some kissing (she said she gets wet just thinking about guys kissing). Then her vision of the encounter went beyond what would be possible at the jackoff club.  She wanted to see a guy first stroke my dick then suck it, taking all of it in his mouth, seeing me enjoy having my dick sucked by a man to the point that I was moaning with ecstasy.  Finally, she said she wanted to see me suck cock and then fuck the guy in the ass until I cum.  At that point, she would love to share a deep kiss with me.  (She later shared other versions of how she would like to see me get fucked, and also that if I let the guy fuck me in the ass, she would bend over in front of me and let me do the same to her.)  Basically the biggest turn-on for her would be to see me let myself completely go and enjoy the pleasures of full sex with a man, while she watched. We both have masturbated to the above fantasy and while reading the responses to my personal posting, and the whole anticipation of what might happen. As far as the more personal encounters that came as a result of this, I will share these in future stories …

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