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

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CockMySuck said:
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.
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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......
 
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thejuneway said:
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......
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This is a great reply. Thank you!

I read through the questions and, while I might actually reply to them sometime, I figured I'd share what I'm thinking in a couple of weeks when we are in person, 1-on-1 again.

When Anderson and I are together (and probably slightly intoxicated – not uncommon for us, but also not debilitating or affecting our memory), I simply want to tell him that jerking off together has crossed my mind recently, and I'll ask him if he wants to. I don't think that's a huge leap for us (again, we've been naked together many times) and yet I know he's at least less uncomfortable with that than anything more intimate at the moment (because, again, he has done that in the distant past). If that leads to us jerking off while on the couch together, or even going as far as helping each other (maybe a stretch at this pace), that would be great. I'm going to share with him how I really feel, which is kind of similar to past conversations we've had: We are SO close and, as we've discussed, we feel comfortable sharing "anything" with each other, and now I'd love to be able to share masturbation, even if that means just being able to jerk off with each other around. I've had a lot of shame around bodies and sex that I'm still recovering from in growing up (we both do from a Catholic upbringing) and I'm tired of being ashamed, and would love to explore and see if we'd be into it.
 
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CockMySuck said:
This is a great reply. Thank you!

I read through the questions and, while I might actually reply to them sometime, I figured I'd share what I'm thinking in a couple of weeks when we are in person, 1-on-1 again.

When Anderson and I are together (and probably slightly intoxicated – not uncommon for us, but also not debilitating or affecting our memory), I simply want to tell him that jerking off together has crossed my mind recently, and I'll ask him if he wants to. I don't think that's a huge leap for us (again, we've been naked together many times) and yet I know he's at least less uncomfortable with that than anything more intimate at the moment (because, again, he has done that in the distant past). If that leads to us jerking off while on the couch together, or even going as far as helping each other (maybe a stretch at this pace), that would be great. I'm going to share with him how I really feel, which is kind of similar to past conversations we've had: We are SO close and, as we've discussed, we feel comfortable sharing "anything" with each other, and now I'd love to be able to share masturbation, even if that means just being able to jerk off with each other around. I've had a lot of shame around bodies and sex that I'm still recovering from in growing up (we both do from a Catholic upbringing) and I'm tired of being ashamed, and would love to explore and see if we'd be into it.
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I am absolutely fascinated by this chat haha
 
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johnjohnston said:
I’m starting to feel like queer males who genuinely have same-sex attractions, passions, romantic affections, emotional investment, relationship comfort, commitment ambitions should not be besties with “straight presenting” men that they find attractive or even “queer-ish” guys who make it clear that they have overall hetero leanings or just guys in general that they know they have attractions and some romantic feelings towards. Shit seems to frequently get messy, and someone ends up not getting what they genuinely want from the situation. Spending years pining after a “bestie” who doesn’t want you or who may only want you to briefly or occasionally can’t be healthy. While coming up with ways to pretty much “trap” or “entice” or “convince” him, it comes off a bit pathetic and creep-like.
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What about gay males who aren’t queer?
 
Emjaydee87 said:
What about gay males who aren’t queer?
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“Queer” for many has become a general umbrella term for “non hetero” or “non gender normal”. Sexuality and preferences and gender is so wide and individual. There are so many identities people use. And the gender, sexual, affection, romantic attachment, relationship comfort, emotional investment, commitment spectrum is so varied. It’s just an easier way to group. I know some still don’t like it (particularly older people). And I used to have issue with it as well. If you take offense that’s fine, but don’t take offense for others.

As far as the actual topic, I wasn’t trying to shame anyone. But if you’re starting threads to ask these questions and you’re indulging long ass responses then you seem to want honest, thorough answers rather than just fantasy and sentimentality. It honestly sounds like you’re in love with him, which unless he’s really into you, can get messy real quick considering he’s in a relationship and your close friendship. You may get the hook-up you want, but you may not like what comes after. And you definitely seem to be trying to come up with ways to “seduce” him. But do what you do.
 
johnjohnston said:
“Queer” for many has become a general umbrella term for “non hetero” or “non gender normal”. Sexuality and preferences and gender is so wide and individual. There are so many identities people use. And the gender, sexual, affection, romantic attachment, relationship comfort, emotional investment, commitment spectrum is so varied. It’s just an easier way to group. I know some still don’t like it (particularly older people). And I used to have issue with it as well. If you take offense that’s fine, but don’t take offense for others.

As far as the actual topic, I wasn’t trying to shame anyone. But if you’re starting threads to ask these questions and you’re indulging long ass responses then you seem to want honest, thorough answers rather than just fantasy and sentimentality. It honestly sounds like you’re in love with him, which unless he’s really into you, can get messy real quick considering he’s in a relationship and your close friendship. You may get the hook-up you want, but you may not like what comes after. And you definitely seem to be trying to come up with ways to “seduce” him. But do what you do.
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I'm definitely not in love with or interested in Anderson in a romantic or relationship way, but I do love him as a friend like I've loved most of my friends. Maybe that wasn't clear in the post but just clarifying that now. We're best friends and I am not interested in anything other than that. But I also don't think friends can't be sexual or get off together.

No, I'm not trying to "seduce" him or entice him or trap him. Some of the responses sort of lean to that. I just want to tell him how I'd love to be able to get off with him, and then go from there. Like I said a few posts ago, I'm going to have that honest, open, clear conversation with him when we're together in a few weeks. I'm opening the door to something I'm open to with him, and he knows me well enough to know I'd never cross a line or do anything he's not okay with. Again, we're that close – especially for a male friendship.

In terms of "not liking what comes after", here's how I feel: if me being myself and letting him know what I want or how I feel is enough to ruin our friendship, it's clearly not as close as it seemed. I'd rather be open, honest and my full self than repress that desire.

To that point, I have another close friend who, after years of friendship, we actually opened up to each other about wanting to hook up and explore together about a year ago. We're still only friends and it will stay that way, but I love that we can also be sexual and not repress that aspect of ourselves.

All to say, many of these situations work out, especially when you have the self-awareness, strong bonds and mutual respect needed to maintain these situations. At this point, I'm pretty confident Anderson and I do.
 
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CockMySuck said:
I'm definitely not in love with or interested in Anderson in a romantic or relationship way, but I do love him as a friend like I've loved most of my friends. Maybe that wasn't clear in the post but just clarifying that now. We're best friends and I am not interested in anything other than that. But I also don't think friends can't be sexual or get off together.

No, I'm not trying to "seduce" him or entice him or trap him. Some of the responses sort of lean to that. I just want to tell him how I'd love to be able to get off with him, and then go from there. Like I said a few posts ago, I'm going to have that honest, open, clear conversation with him when we're together in a few weeks. I'm opening the door to something I'm open to with him, and he knows me well enough to know I'd never cross a line or do anything he's not okay with. Again, we're that close – especially for a male friendship.

In terms of "not liking what comes after", here's how I feel: if me being myself and letting him know what I want or how I feel is enough to ruin our friendship, it's clearly not as close as it seemed. I'd rather be open, honest and my full self than repress that desire.

To that point, I have another close friend who, after years of friendship, we actually opened up to each other about wanting to hook up and explore together about a year ago. We're still only friends and it will stay that way, but I love that we can also be sexual and not repress that aspect of ourselves.

All to say, many of these situations work out, especially when you have the self-awareness, strong bonds and mutual respect needed to maintain these situations. At this point, I'm pretty confident Anderson and I do.
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Best of luck with it man :)
 
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CockMySuck said:
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.
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Seems like a lot of people are responding generally and not to this specific situation presented, using the post as an opportunity to give life lessons/advice instead of advice for this individual and unique relationship (by which I don’t mean “relationship”).
 
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It doesn’t seem like there is a lot of risk here, based on your responses, so it seems like you are mostly looking for ideas. That being said, seems like there is some fear in it (because you said you get too nervous). So, what do you think you might be afraid of?

The concern for me is his girlfriend. I mean, it’s his relationship, he can make his own choices and they reflect on him, not you, but that can be a can of worms. It might affect your relationship if he has guilt from cheating, if she finds out and is unhappy, she might not want him to spend time with you again, or a whole lot of other outcomes. If they are open too, like your relationship, then I wouldn’t worry about it.
 
CockMySuck said:
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.
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Well, i guess based on your very detailed accounts, he’s into you. You just need to make the first move! Go for it. Set the mood, whisper something dirty in his ear then stroke his dick and the rest will follow. I don’t understand what else you’re waiting for. There were already hundreds of signals from him. Get over the thrill and the drama. Fuck him already. Full stop.
 
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