I really want to (finally) hookup with my closest friend

[RyanMars]

Ultimately, you can’t control how people feel. While there are many queers who get off on someone being a “challenge” or a situation not being “basic” and having more complications. However, developing feelings for a friend is borderline normal stuff. While we’ve all been there as far as falling for a “straight”/straight-presenting/semi-queer-ish/seems kinda, sorta into you dude.

As I already said, a lot of guys are well aware that their queer male friends have crushes on them. And they egg at that for the ego boost or for some free therapy or sometimes for money and opportunities. It’s not about the dimensions of his friend’s sexuality, whether not he’s closeted, or where he is in the gender, sexual, affection, affirmation, romantic attachment, emotional investment, relationship comfort, commitment spectrum. Pining over a friend for years who is not unabashedly into you (even if they hook up with you sometimes) is often stunting and toxic and frequently leads to messiness and heartbreak. It’s not cute, especially after you hit a certain age. You do have to start thinking more practically instead of being stuck in fantasy or trying to “save” someone.

You are right it is stunting. I hate to say this, but it shouldn’t be this hard to find a man to hookup with you. If it’s not about hooking up then it’s the chase and wanting men you can’t have which is destructive.

 

[AllDixNeedLuv69]

If he says he may be bisexual or even gay.. he is already confused about his sexuality ..so only thing can happen is if you try to do anything and he says no or even yes.. is this something you want so bad that can ruin your friendship .

I’ve had couple friends same way has a girlfriend now probably because it’s what family and society expects out of him ..

if he thinks he may be gay he needs to figure it out before he gets with her marries her and has kids ..then he will be like a lot of guys out there getting divorced deciding to no longer lie to themselves about their feelings

ask him what gay things he is curious about and go from there …


but remember if friendship is worth it first

 

[deleted492746]

To be clear, this guy is bisexual... He came out to me, as I mentioned in the post and he acknowledges being bisexual now.

 

[Willo]

Damn this thread became so depressing...

We really only know a glimpse of their relationship through the eyes of one of the parts who feels like they could hook up. Everyone here is getting into much deeper feelings than the ones OP presented which was that of a friendship that could have some sexual action. Like I said in my first post, from the way he worded it I feel like he could make a move and if it's not reciprocated then yeah maybe let it go or see what he has to say, like maybe he just wouldn't do something since he is in a relationship atm, but always wanted to and was waiting for OP to make a move (just an example of a scenario). Sexuality isn't a black and white thing as everyone here is painting it out to be and if this was a clear straight guy who has shown no interest I would agree with the latest replies but he has literally came out as bi and showed a lot of openness to OP. Some of the replies here have been almost insensitive even by nearly telling him that he should just stop being friends with the guy or to just snap his fingers and stop feeling attracted like its that easy.

 

[deleted492746]

Damn this thread became so depressing...

We really only know a glimpse of their relationship through the eyes of one of the parts who feels like they could hook up. Everyone here is getting into much deeper feelings than the ones OP presented which was that of a friendship that could have some sexual action. Like I said in my first post, from the way he worded it I feel like he could make a move and if it's not reciprocated then yeah maybe let it go or see what he has to say, like maybe he just wouldn't do something since he is in a relationship atm, but always wanted to and was waiting for OP to make a move (just an example of a scenario). Sexuality isn't a black and white thing as everyone here is painting it out to be and if this was a clear straight guy who has shown no interest I would agree with the latest replies but he has literally came out as bi and showed a lot of openness to OP. Some of the replies here have been almost insensitive even by nearly telling him that he should just stop being friends with the guy or to just snap his fingers and stop feeling attracted like its that easy.

Thanks for your reply and putting this into words. To me, those replies only suck because I thought I laid out our relationship very clearly. A lot of people project their assumptions and experiences onto other people and, also, don't read closely. You "get" the situation and I appreciate that.

 

[deleted492746]

Damn this thread became so depressing...

We really only know a glimpse of their relationship through the eyes of one of the parts who feels like they could hook up. Everyone here is getting into much deeper feelings than the ones OP presented which was that of a friendship that could have some sexual action. Like I said in my first post, from the way he worded it I feel like he could make a move and if it's not reciprocated then yeah maybe let it go or see what he has to say, like maybe he just wouldn't do something since he is in a relationship atm, but always wanted to and was waiting for OP to make a move (just an example of a scenario). Sexuality isn't a black and white thing as everyone here is painting it out to be and if this was a clear straight guy who has shown no interest I would agree with the latest replies but he has literally came out as bi and showed a lot of openness to OP. Some of the replies here have been almost insensitive even by nearly telling him that he should just stop being friends with the guy or to just snap his fingers and stop feeling attracted like its that easy.

Thanks for your reply and putting this into words. To me, those replies only suck because I thought I laid out our relationship very clearly. A lot of people project their assumptions and experiences onto other people and, also, don't read closely. You "get" the situation and I appreciate that.

As a mini-update, we're going on a 1-on-1 trip together in late March.

I don't want a relationship with him in a romantic sense, but I would love to jerk off together. I'm not sure how much further I'd want to take it – it depends on how comfortable he is, which has always been the case. Either way, I'm super thankful for the close friendship I have with him, and that we can open up to each other. It's not everyday that you form a friendship like this one and, while I've had a number of close friends and a few best friends over time, our friendship is one of a kind. We will continue to be friends and I'm happy that we're so close that I can legitimately consider actually hooking up with him. Believe me, I've been attracted to a number of guys I'm friends with but this is different, in that I've gotten the sense (strongly) that he may be interested and, again, we're so close that it kind of makes sense. There aren't many ways we can get closer...

I have some thoughts on how I want to approach the situation... No, I'm not going to have him walk in on me jerking off.

I'll let you know how it actually goes after our trip. Interested in seeing other comments come through and hopefully they're not cringe.

 

[AussieGrayson]

He has a partner have some respect

 

[AllDixNeedLuv69]

i forgot to mention that over the years i kept very few friends and the rest of the guys as opportunites to get laid-- some i was with we had fun and we all knew it wasnt anything serious but just sex--i did meet few guys that called me names and disappeared for good---and some punched and kicked my ass for making a pass at them--but i still looked for the next cock i was going to taste---i lived this way until about 30 maybe 32 years old and mellowed out with this lifestyle--now i got couple so called friends and thats ok--i lived without them for this long i can live longer without them--so now i still just go out for sex--

 

[JX711]

As much as we would like for everyone to be bisexual so increase our chances in getting to know someone we have a crush on .. but that isn’t the case

straight men and women need to be around to create more straight men and women as well as gay ones..

I had a friend he is straight but he was the biggest tease since knowing I was gay .. he’d show his bare ass. Spread his cheeks show me his asshole a done within inches and flash his hard cock at me telling me to enjoy it because that was as close as I was goi going

So after few times he did that I just ignored him .. and I think it upset him more that I quit acting interested in him ..z.. so after that he quit doing it


So as much as we like seeing sexy how straight men we need to move along and find gay men or bisexual o es

Where is this guy now? Married?

 

[JX711]

If you apologize to a straight friend who knows you're gay for getting "too attached & don't want to mess anything up" and he says "nah, you're good". You've flirted a bit & joked twice about giving him blowjobs and he hasn't turned you down. He says you never have to be afraid to ask him anything...what does any of this mean?

 

[Hua Cheng]

Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.

***

For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.

Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.

We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.

I settled into being (just) best friends and not hooking up... Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.

This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us even closer together, but we were thousands of miles apart and each quarantined.

Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:

• Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
• We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
• When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
• We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.

As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.

I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.

I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.

Hello baby, I'm drunk right now and I came across your thread.
So, this opinion of mine is totally based on a drinking delusion and a horrible google translator translation because I'm not in a position to translate this into Portuguese at the moment. That said, I think you have a very solid relationship with this friend, and apparently he's comfortable with you too. The part of you being comfortable naked next to each other and the massage part says a lot about that intimacy. And I know you're feeling something coming from him too. It can't just be in your head. What I'm going to say here you'll probably understand since he's in a non-monogamous relationship, which he doesn't, apparently. This can be a little tricky as he is attached to a relationship bond with one person and has all the cheating issues and the like.
So, I think it's fair that you ask and communicate your will to him, because you have a strong relationship for that, but consider if he would accept because of his monogamous relationship. This week I went to smoke weed at a friend's house and there I realized how propitious the situation was to the point where I could imagine having sex with him. I never had that instinct with him because we're almost brothers, but I don't know. I could sit on that eight-inch dick at that moment with no regrets. Which leads me to realize that maybe we separate and define many of our relationships in friendship and love relationships. But no, these things can be together in a single relationship, like yours and your friend's.
I'm looking forward and rooting for you and forgive me if this text gets weird, it's google translator baby. Hope you can beat him one and that you guys can have a good time. Kisses from your friend from Brazil.

 

[john412]

Just have a few drinks together, get in the hot tub and go for the kiss. You got this brother. You guys seem like great friends so I don't see that it'll damage your relationship if he says no or pushes back. Just blame it on the alcohol!

 

[joshua388]

Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.

***

For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.

Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.

We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.

I settled into being (just) best friends and not hooking up... Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.

This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us even closer together, but we were thousands of miles apart and each quarantined.

Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:

• Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
• We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
• When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
• We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.

As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.

I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.

I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.

Do you watch Euphoria? the first 15min of Season 2 Episode 3 is a great example of this, beautifully shot and great ST too.

 

[deleted492746]

Do you watch Euphoria? the first 15min of Season 2 Episode 3 is a great example of this, beautifully shot and great ST too.

I don't, but I'll have to watch, or at least try to find that scene! I don't have HBO, so let me know if you have the clip or episode.

 

[deleted645178]

Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.

***

For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.

Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.

We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.

I settled into being (just) best friends and not hooking up... Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.

This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us even closer together, but we were thousands of miles apart and each quarantined.

Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:

• Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
• We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
• When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
• We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.

As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.

I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.

I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.

My best friend is my neighbour from 2 doors down, were openly gay, both partnered,but our friendship crossed over the line to sex buddies last year, I just told him how I felt after three long years, it led to tears,hugs and eventually some amazing sex,we don't love each other, we just love being together having sex ,our partners do not know.we keep it to ourselves.i think u need to tell him how u are feeling..get it in the open.it will probably do ur relationship good...Good luck.

 

[deleted492746]

Do you watch Euphoria? the first 15min of Season 2 Episode 3 is a great example of this, beautifully shot and great ST too.

@joshua388 I still haven't watched the episode but I found this sweet (sad toward the end) video of the storyline. It definitely hits close to home.

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[bidad4son]

Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.

***

For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.

Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.

We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.

I settled into being (just) best friends and not hooking up... Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.

This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us even closer together, but we were thousands of miles apart and each quarantined.

Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:

• Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
• We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
• When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
• We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.

As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.

I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.

I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.

I can say as a biwmmm,
you would be surprised how few 100% kind of people there are. In the Navy a few drinks often led to fun of which there was no memory the next day.

 

[JX711]

I can say as a biwmmm,
you would be surprised how few 100% kind of people there are. In the Navy a few drinks often led to fun of which there was no memory the next day.

Unrelated, but what do you think it means when a Conservative guy is going on & on attacking gays and saying it's wrong, disgusting etc. ?

 

[edgewater57]

This thread really captured my attention. What a great gift that you have this friendship, and you clearly treasure it. Along with you, I felt sad to read some of the responses, which didn't seem to really get where you are at. No, you're not pining after him or something! I'm sure whatever actions you decide to take will be congruent with the way your relationship already works. Since you are the only one that knows your history, I guess it's not surprising that the tactics about what to do next that come to other guys' minds would seem crazy to you. You put so much thought and careful writing into the post, it seems you're looking for some insight about your situation that would make it more clear to you how to shape a conversation that seems appropriate for who you two are. May you get that insight and have wonderful continued growth in your friendship!

 

[thejuneway]

Hi everyone! It's crossed my mind to start a thread for the longest while... Yes, this is a 100% real story, and someone I'm currently navigating, which is why I finally decided to make a thread and ask for input, helpful advice, or other similar stories.

***

For the last 5 years, I've been best friends with someone I'll call Anderson – mostly because he reminds me of a young Anderson Cooper: handsome, well-spoken but funny, stoic at times, looks amazing without a shirt, an explorer type. We're both young millennials, and have known each other since our teen years but grew closer 5 years ago.

Up until the start of the pandemic, I figured that Anderson was straight. As with most of my "straight" friends, I entertain the possibility that they might not be straight. But, a few years ago, I remember being stoned on his couch with him; I shared my experience being bi and I remember talking vaguely about what it's like, but I never got the impression that he was bi. That was one of a few times where I opened the door wide for him to share his sexuality or curiosity, though I never explicitly put him on the spot and asked.

We had a lot of these conversation while at his family's big house, alone for the weekend. Honestly, I remember being really horny at this time and hoping any mention of sex or sexuality or horniness would escalate into us hooking up. He's a really touchy feely guy and, the way he looks at me (especially when we know we won't see each other for a while) is filled with sexual tension, when we hug (which we do a lot) and look into each other's eyes. The sexual tension has been there but, again, I assumed he was straight.

I settled into being (just) best friends and not hooking up... Then the pandemic happened (while he was thousands of miles away from me) and he told me he might be bi or even gay.

This set off a string of calls with him where we talked at length about sexuality and where he opened up. Anderson not only shared how he was feeling with his sexuality with me (which he's still not "out" about) but also his horniness... at length. It makes me hard to think about it – his stories about hooking up with certain women, his jerk off habits in quarantine, how he just wanted to fuck, what we wanted to do or wanted done to us by other people, open relationships, threesomes, etc. A few times, I got so hard during the conversation that I'd start playing with my dick, and I think he would too – the moments it might get a little quiet on the line while we were talking about these horny topics and laying around. At one point, every time we'd talk, it was about how much he wanted to cum (or, by that point, "explode"), not fucking in quarantine or for a while before. All of these conversations, of which there were hours and hours, brought us even closer together, but we were thousands of miles apart and each quarantined.

Well, when we were finally able to be in person again, we were indeed closer. This is the part I'm going to sum up because there's a lot that has happened over the last year and a half after those calls:

• Anderson started dating someone (a woman) he used to date, and they're still dating now with their own bumps in the road and struggles finding a good flow sexually. Everything below has happened since they started dating.
• We've gone on at least a dozen trips together, mostly to houses or cabins with hot tubs. While he already had the habit of walking around, at times, without a ton of clothes (which we'd talked about before) he actually started our habit of skinning dipping in the hot tub. He's always been pretty comfortable with nudity, so it's not a huge surprise and I've read this as an overtly sexual thing. Don't get me wrong: I've been hard many times seeing him naked, including in hot tubs, but he doesn't seem horny.
• When we started talking those trips, we also started giving each other massages. This was something I offered at first and did with Anderson clothed at first (and he returned the favor). That same trip, we eventually did it again while he was in his boxers. After that first trip, we've actually done these full body massages (which happen at least once every trip) completely naked. So we're comfortable being naked in front of each other (to the extent that I don't have a boner) and rubbing each other down from head to toe. But again, neither of us has crossed a line into anything blatantly sexual. We also cuddle and nap together from time to time.
• We still have these deep conversations about sex, sexuality, horniness, how close we are, etc. One of the recent trips we had, we were casually talking about how I love sucking dick and Anderson was talking about how he likes to be jerked off more than he likes being blown. I thought that was notable – I've probably never heard that before. Shortly after, he revealed that he used to have a friend growing up who he used to jerk off with, stroking each other's dicks; he shared this as he opened up more about his sexuality and emotions he was/is dealing with. In retrospect, I wonder if this was his was of saying that he'd be open to me jerking him off, or us jerking off together.

As the title suggests, I want to finally hookup with Anderson and I'm taking another trip with him in the next couple of months. It'll be just the two of us and, hopefully, there will be a hot tub.

I'm not afraid it will end our friendship if I ask or I try; I'm just not sure how to ask or try, because I get so nervous but also haven't been in these situations, so I'm not sure what I should say or do. I know we're close enough to where having a conversation about fucking with each other, while new ground, wouldn't hurt our friendship; maybe it could bring us closer together. Again, I'm not sure how to have that conversation, how to build up to it, or when. I mentioned that he is dating someone and I wonder if that's part of his hesitation in addition to his sexuality; conversely, I'm dating someone (a man) and in an open relationship where I explicitly have permission to hook up with Anderson and others, if it goes there.

I'd love to hear from others here with any 1) good advice or reactions you have and 2) any similar stories you have about wanting to hook up with or actually hooking up with your best friend.

So.... I'm like an entire month late with this reply but as I reading your post I can't help but have a few questions pop up in my head so here goes:

1) So during your hot pandemic phone conversations, you mentioned that you'd both share about how you both wanna have sex and what you'd both like to do and be done. I was wondering if he referenced women or men in his fantasies?

2) When did he start dating his ex again? Was it right before the home quarantine period was about to end and you'd meet each other again? If not, when did you start dating and did he start dating around the same time then?

3) You mentioned being hard when you first started seeing him naked and mentioned he didn't seem horny? Why did you think that was? I'm guessing these hot tub and massage moments was just the both of you and no one else and if you're hard, it would mean that it's in response to him. Or is he just used to other men getting hard from being naked like the showers in the gym and stuff?

4) Has he ever done anything more with a guy other than jerk off together? Cause I think his mention of preferring being jerked off to getting head might not have been an invitation but a stop to getting head. Basically I think that if he hasn't had much experience with guys and he's still exploring, he might not be the type to dive right into it. But he's the type to take it slow at first. And knowing which type he is would be how you would approach the situation. Some people just weirdly shut down when things become too much for them to digest and comprehend. I definitely agree with one of the replies about being sober. But not so much because of the guilt but rather that being his excuse for not remembering anything and not wanting more, worse, said you took advantage of him when he suddenly decided that's not what he wants anymore.

5) In the beginning you mentioned him being an explorer type. Do you think he's basically just exploring with you? This is about knowing just how much exploration he's open to and also if he's just exploring you'll know how much and what to "invest" in this relationship. I feel like with how things are, I would catch feelings if I were you. But of course, that's me and not you. Sorry for the projection.

6) Ok this one might sound a bit harsh but I don't mean it that way at all. While you might not think or care how your invitations/suggestions will affect the friendship, he might? Since he's not out, I don't imagine him sharing his homosexual side and his experiences with a lot of people, not to mention his "dirtier", hot and sexual aspects of that so that's why he feels so close to you. He's sharing something he tells no one else. And talking about fucking and actually fucking are pretty different. So if he's not had experience, it might actually be pretty unnerving for him. Actually, I'm wondering if that's why he hasn't done anything or made a move. It's because he's nervous as fuck, doesn't what to do and how to do so he was hoping you'd hopefully lead the way and apart from him being in a relationship being a possible reason as well, I was wondering if you being in one was part of it too? Does he know you're in an open relationship?

What I would do, if it were me, I think when the topic of sex is brought up, I'd slip in the question "So I gotta ask cause I'm curious and have been curious for a while now, have you ever thought about the both of us having sex? And trust me, no judgement whatsoever from me whatever your answer is". Kind of a direct but also kinda indirect question? LOL

End of March is just a few weeks away. Can't wait to hear what happens......