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Best Friend Problems...

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Dec 9, 2018
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About three years ago I had a roommate who I hit it off with and we became really good friends. After a year or so he started calling me his best friend and now we hangout every other week or so. I'm actually good friends with his now wife as well and most of the time I go over to their place and we all hangout, talk, and drink together. I'm single and I often feel like the third wheel (I am) when I'm around them but they do a decent job of not making me feel as such.

There's been a few occurrences were we're all hanging out having a good time and the wife subtly mentions how close we all are (insinuating sexual tension between us) but my BF has jumped in saying "No were not having a threesome!". Even though it kinda feels like something that should've happened along time ago since I know his then girlfriend at the time would've been interested but it never did and I've never brought it up. I honestly was never really interested in having sex with them since they're both into bdsm type sex and I'm not (they don't know it but I've tried it before and I didn't like it). However, he recently mentioned that they've had a foursome with another couple (girl, guy) and honestly it kinda hurt knowing that he shared that moment with another guy even though he claims he's only ever interested in threesomes with other girls. I still haven't brought it up to him and I don't know how to without making it sound like I'm a jealous loser.

I feel like he's constantly guarded around me and when we do talk it's usually about our work-life or current events but he doesn't like talking a lot about things he feels are too personal unless he's drunk. He's told me he had a troubled past and upbringing while hanging around the wrong people but he never really elaborates on it. I opened up to him about being sexually attracted to both girls and guys and the moment I told him he opened up a little bit about how he knew that was hard for me to tell him because there's things he wants to tell me about himself but he can't because he holds me in such high regard and respects my opinion of him so much that he doesn't want me to think any less of him. His wife recently told me something very personal about him that she thought I should know but she says he will never tell me because he doesn't think I would understand or accept him. Bringing the story back around the couple that they slept with was a couple they both knew before they met me though they just recently connected again and then had a foursome together.

The problem is I want to talk to him about it and ask why has he never tried to become closer with me in that way, even flat out refusing to if it's mentioned. Is it because he's not interested in a threesome with another guy much less his "best friend", or because he's afraid if I see him that way I'll think of them both differently, or is it that he's just not interested in a threesome with me period? I feel like we've never truly had a strong bond with each other since we've only known each other a short time, and now that he's married we don't get to hangout often just the two of us to actually talk and understand each other more. I get that he may want to hangout with other couples and me being the third wheel is pretty old now but I don't know how to approach him to tell him all I really want is to have a stronger connection with him and I feel like the odd man out even more now knowing what happened and that he likes keeping me in the dark to protect himself. Sorry if I'm rambling but I'm thinking about finding the right time to talk to him about everything including his past and how I feel like he keeps shutting me out of everything personal in his life. If I'm overthinking this or being irrational please let me know but I don't want this to continue on feeling like I'm only a friend of convenience for him.

Any comments would be appreciated thanks!B
 
I get what your saying, but I honestly think you should let this go. Not the friendship but the notion of making it more than what it is currently. He clearly doesn't want to go there with you or he would have already, pushing the subject may cost you his friendship. You need to accept the current terms of your relationship or let it go all together.
 
i would value the friendship . If he wanted to talk about anything else with you; he would have already done so. So just value the friendship.
 
"'Best friends'" share their thoughts.
Ask if there's any subject he'd find hard to talk to anyone about and see what he says. And make it clear that while he was concerned you'd think less of him, he's your main guy and that means you would always want to know what's important to him. So, if he ever feels like talking about something, you're there for him because he's - after all - your best friend.
Have you told him he's YOUR best friend? Reciprocity works wonders.
 
There shouldn't be secrets between best friends, at least virtually, or it's not that much of a friendship. Could be something compromising but his insecurity about telling you also shows he cares for you, otherwise he wouldn't even have brought it up. If you think you're ready to find out you could make him feel at ease by accepting or understanding what he's worrying about. I don't think the best-frienship would make sense with this dark secret - would be more of an uninvolved friendship. In the worst case you might break up. I mean relationships end after longer periods and strong connections as well.
 
I am a gay man in my 30's and have a straight best friend of 18 years since highschool. When were in school, I thought he was so irresistably adorable and would occasionally rub his cock through his pants. It didn't go further than that until we both ended up living back in our home town after college. Now in our early 20's he let me suck him off a couple of times. He wasn't really into it, and when I asked if I should stop, he just said, "Oh no. You started this, you're gonna finish it."

After those few times, we stopped being intimate like that and he has been dating women exclusively since then.

Once in a while, when I'm under extreme stress, some of my old feelings for him will bubble up. One time recently when I was in such a state, I asked him why he and I never went further than what we did. He said it's because I wouldn't be able to do it without forming an emotional attachment to the action. And as my best friend of nearly 20 years, he knows me as well as I know myself, if not more sometimes. I ask him if he ever regrets anything we've done or if he feels I ever pressured or forced him to do anything he didn't want to do. He assures me that everything that happened did so because we both wanted it to. Or at least both wanted to try it out.

It's been over 10 years since he and I were physically intimate at all, and I'm okay with that. In losing a potential hook-up, I've gained someone who has become the older brother I never had. We consider each other family. If I had to forego physical intimacy with him to gain one of the few people in my life who sincerely cares about me and trusts me above almost everyone else, I am glad that we put an end to the casual blow-and-gos.

That being said, I realize now that I took a huge risk entering into sexual situations with someone who meant so much to me. If he felt weird about it or started to resent me in some way, our friendship would have ended. I think you should be careful how you approach this subject if your friend means as much to you as my brother means to me. I understand how unanswered questions about what could be or what could have been can haunt you incessantly to the point where you will risk everything to get your answers. You just have to weigh whether or not keeping your friendship the way it is is more important. I can't say for sure, but it is even possible that the experiences he and I shared contributed to our friendship being as amazing as it is now.

If he is truly your best friend, you will be able to at least talk about your attraction to him and ask him why he hasn't considered being intimate with you. Even if he has been in sexual situations with another couple, it could be that sexual experimentation with strangers is preferable to jeopardizing the relationship with people you know and care about. Talk to him about your feelings and concerns. I can only hope that he is the friend to you that mine has been to me: open, honest, patient, and understanding. I know finding such a person is rare in this world, but I wouldn't call anyone my best friend who would judge me and not be able to accept me for all my good as well as bad.

Good luck.
 
I am a gay man in my 30's and have a straight best friend of 18 years since highschool. When were in school, I thought he was so irresistably adorable and would occasionally rub his cock through his pants. It didn't go further than that until we both ended up living back in our home town after college. Now in our early 20's he let me suck him off a couple of times. He wasn't really into it, and when I asked if I should stop, he just said, "Oh no. You started this, you're gonna finish it."

After those few times, we stopped being intimate like that and he has been dating women exclusively since then.

Once in a while, when I'm under extreme stress, some of my old feelings for him will bubble up. One time recently when I was in such a state, I asked him why he and I never went further than what we did. He said it's because I wouldn't be able to do it without forming an emotional attachment to the action. And as my best friend of nearly 20 years, he knows me as well as I know myself, if not more sometimes. I ask him if he ever regrets anything we've done or if he feels I ever pressured or forced him to do anything he didn't want to do. He assures me that everything that happened did so because we both wanted it to. Or at least both wanted to try it out.

It's been over 10 years since he and I were physically intimate at all, and I'm okay with that. In losing a potential hook-up, I've gained someone who has become the older brother I never had. We consider each other family. If I had to forego physical intimacy with him to gain one of the few people in my life who sincerely cares about me and trusts me above almost everyone else, I am glad that we put an end to the casual blow-and-gos.

That being said, I realize now that I took a huge risk entering into sexual situations with someone who meant so much to me. If he felt weird about it or started to resent me in some way, our friendship would have ended. I think you should be careful how you approach this subject if your friend means as much to you as my brother means to me. I understand how unanswered questions about what could be or what could have been can haunt you incessantly to the point where you will risk everything to get your answers. You just have to weigh whether or not keeping your friendship the way it is is more important. I can't say for sure, but it is even possible that the experiences he and I shared contributed to our friendship being as amazing as it is now.

If he is truly your best friend, you will be able to at least talk about your attraction to him and ask him why he hasn't considered being intimate with you. Even if he has been in sexual situations with another couple, it could be that sexual experimentation with strangers is preferable to jeopardizing the relationship with people you know and care about. Talk to him about your feelings and concerns. I can only hope that he is the friend to you that mine has been to me: open, honest, patient, and understanding. I know finding such a person is rare in this world, but I wouldn't call anyone my best friend who would judge me and not be able to accept me for all my good as well as bad.

Good luck.

Absolutely Spot on. Take it from me, and I've been there and we (note I said we) went too far and I lost that "best friend", Manticore is right. I would give anything to have my buddy back but alas that will never ever happen. Those relationships are once in a lifetime occurrences and rarely repeat themselves. If you want to hear the story I'll tell it again but only if you guys ask.
 
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