Should I hook up with my "straight" best friend?

[Jarren.Anthony]

Okay so here's the sitch guys...

My best friend (let's call him Adam) has always been giving me confusing signals. We've known each other for 2 years so far and we get along great. Like, really great. Our personalities are completely the same. He's one of the best looking guys I've ever met, but he's straight. There's never been an issue or embarrassment for him that his best friends gay, and I've always loved that about him and his confidence. A jock and a gay guy being best friends can obviously be considered "incompatible" in societies perspective. The thing though is that starting 3 months ago, when we would hang out at his place or mine, and we would start drinking together, his personality almost does a 180. He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally good to bed, he loves to cuddle with me. (Like, he pulls me in hard) When we lay together though he never gets hard at all or even a chub, so it kind of seems to me he really just likes the comfort of it and connection.

I've never initiated anything myself though and have always just gone along for the ride because I never want him to feel uncomfortable since he identifies as straight. He also says when we're drunk that he'd never do anything like this with anyone else except me because he feels so comfortable around me. When we're sober though, we never talk a peep about it. Like, not one word. Kind of like it never happened in the first place, but then when we drink again together, it's back on.

I'm moving back to LA next month because my lease is up and I'm bored with Palm Springs, so that means I'm not going to be hanging out with him all the time anymore and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.

My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here? I'm scared as hell to do so and have it go south, but then again I wont be hanging out with him anymore so I wouldn't have to worry about it being awkward afterwards if it does goes bad. But what if it goes good? I've always wanted to hook up with him, like...bad, but I didn't want to lose my best friend here if it didn't go well. I keep going back and forth and I don't have anyone to run it by except the people in our friend group, which I'd never do. But since I know you guys might be able to relate or have some good input to add, I figured I'd try and ask for help here

Thanks guys!
(Please be kind in the comments)

 

[varina1]

When he's whipped it out have you ever complimented him on ?

 

[Jarren.Anthony]

When he's whipped it out have you ever complimented him on ?

Yes! When he whips it out I kind of feel pressured to say something about it so I just say "damn dude, you have a nice dick" or comments like that. He's also seen my dick multiple times too because we've pissed together and also whipped them out to comment on our manscaping jobs when it comes to our pubes. Just super random stuff, but I try to keep PG in a way because he's like a "bro" if that makes sense, lol.

 

[dreamer20]

My best friend (call him Adam) ... We've known each other 2 years and we get along great...there's never been an issue or embarrassment for him that <I'm> gay ... starting 3 months ago, when we would hang out, and start drinking together... He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally <got> to bed, he loves to cuddle with me...he really just likes the comfort of it and connection.
I'm moving back to LA next month because my lease is up ... and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.
My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here?

This is a very straightforward situation DaddysBoyy. I would simply tell Adam I'm glad that I had him as a friend and sorry we won't be seeing each other as much. And I would make sure that I held him and kissed him before we parted. He has shown you what he is comfortable doing. Be just as affectionate as he is, but do not stray beyond that comfort zone is my advice.

 

[OptimusJet]

Perhaps over drinks just talk to him about all the previous experiences and ask him if it was just because he was looking for comfort or if there is something else going on there. Make it so it's not so blunt and in ya face and immediate if you know what I mean. Just cascually talk about it.

To me, It's a hard one because I know of alot of straight guys that once you mention you're Gay or Bi they immediatley start looking for attention in ways you start questioning their sexuality but in reality they are just looking for confidence in themselves but also just being good friends and accepting you and being comfortable around you. Little do they know it can be really hard and you can get mixed signals especially when you "Like" one of them

Since coming out as bi with my friends I have seen all their dicks as they are comfortable with just showing it now but I think they are just looking for that opinion from a "Gay". They are looking for the confidence boost. They really want that "Oh wow your dick is amazing" comment.

But non have kissed me and cuddled up to me though so there might be something there, I couldn't really tell you but all I can say is my friends wouldn't do that to me. And if they did that would tell me they actually want it and I would act on it immediatley. They can't get mad when they are the ones making the moves. Just set yourself boundaries and say "hey if you're gonna start kissing and cuddling me it's game on.. we are gonna start moving some furntiture around" lol.

Best of luck anyway and goodluck with your future endeavours in LA

 

[Jarren.Anthony]

Perhaps over drinks just talk to him about all the previous experiences and ask him if it was just because he was looking for comfort or if there is something else going on there. Make it so it's not so blunt and in ya face and immediate if you know what I mean. Just cascually talk about it.

To me, It's a hard one because I know of alot of straight guys that once you mention you're Gay or Bi they immediatley start looking for attention in ways you start questioning their sexuality but in reality they are just looking for confidence in themselves but also just being good friends and accepting you and being comfortable around you. Little do they know it can be really hard and you can get mixed signals especially when you "Like" one of them

Since coming out as bi with my friends I have seen all their dicks as they are comfortable with just showing it now but I think they are just looking for that opinion from a "Gay". They are looking for the confidence boost. They really want that "Oh wow your dick is amazing" comment.

But non have kissed me and cuddled up to me though so there might be something there, I couldn't really tell you but all I can say is my friends wouldn't do that to me. And if they did that would tell me they actually want it and I would act on it immediatley. They can't get mad when they are the ones making the moves. Just set yourself boundaries and say "hey if you're gonna start kissing and cuddling me it's game on.. we are gonna start moving some furntiture around" lol.

Best of luck anyway and goodluck with your future endeavours in LA

That explanation was amazing! Thank you so much for that input. The way you stated it and perceived it from a different view angle really opened my mind. I can definitely tell when he's drunk that he likes that validation if I give him any. He's also a Leo if that says anything at all, lol. I don't really go far into astrology or anything, but I've just heard that Leo's tend to have that sort of quality when it comes to boosting their ego.

The way you stated everything though actually makes a lot of sense. It's just going to be a little tricky now to differentiate the ego vs the "signals". I've never put much thought into seeing his dick or vice-vera just because it's always just been a "bro" thing without any thought much behind it, but since I'm gay I'm pretty sure he knows it triggers something in my brain knowing that I have a certain lust for it.
When he kisses me it always just seems like a joke to him, but the cuddling in our underwear is where it gets me. Every time he grabs me close to him in bed and holds me tight, my arm's always on his chest and there's nothing more I want than to travel my hands down and slip them into his underwear, but because he's soft I even up coping out every time. If he was ever chubbed or hard at all then it'd definitely be game on immediately, but because he's soft I back off. I always have to do everything in my power too to not pop a boner when my legs are around him. It ended up happening once and we didn't say a word about it, we just laid there and fell asleep.

Now next time I'm with him I'm really going to pay attention to him soaking up my validation and when he seeks it. I kind of wonder what would happen now if I didn't validate him. I'm curious if he would try harder or not, lol. I think you're absolutely right though about "how can he be upset with me when he's the one giving me these signal?" That made so much sense.

I think I'm just going to go for it now. If the same thing goes down on my last night there, I'm going to have to make a move. If I don't, I also know I'll be curious for the rest of my life of what would've ever happened if I went for it. I'd beat myself up about it forever if I chickened out. I guess in the end I'd rather try and even get rejected, than live the rest of my life wondering.

Thank you so much dude for your input! I really appreciate it.
And thank you for your best wishes.

 

[deleted18388141]

No
don t think of him
don t think of it
it s a friend! It must stay like that
find someone who is available!

 

[siranwrap1330]

Dude, totally go for it. If he's kissed you (even if he plays it off as he just joking around) and snuggles with you in bed and holds you and you're both in your underwear...he wants something to happen with you. He is probably curious and wants to do things with you, but bc he's straight, he needs you to make the next move. So just do it,

I have many straight buddies and they'll whip out dicks when we are drunk, but that's all that happens. and then i've had a few straight guy friends who whip it out and then wanna see mine too bc they are curious and with those type of straight guy friends, they wanna try dick but needed me to make the first move.

 

[Soulsurvivor25]

Okay so here's the sitch guys...

My best friend (let's call him Adam) has always been giving me confusing signals. We've known each other for 2 years so far and we get along great. Like, really great. Our personalities are completely the same. He's one of the best looking guys I've ever met, but he's straight. There's never been an issue or embarrassment for him that his best friends gay, and I've always loved that about him and his confidence. A jock and a gay guy being best friends can obviously be considered "incompatible" in societies perspective. The thing though is that starting 3 months ago, when we would hang out at his place or mine, and we would start drinking together, his personality almost does a 180. He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally good to bed, he loves to cuddle with me. (Like, he pulls me in hard) When we lay together though he never gets hard at all or even a chub, so it kind of seems to me he really just likes the comfort of it and connection.

I've never initiated anything myself though and have always just gone along for the ride because I never want him to feel uncomfortable since he identifies as straight. He also says when we're drunk that he'd never do anything like this with anyone else except me because he feels so comfortable around me. When we're sober though, we never talk a peep about it. Like, not one word. Kind of like it never happened in the first place, but then when we drink again together, it's back on.

I'm moving back to LA next month because my lease is up and I'm bored with Palm Springs, so that means I'm not going to be hanging out with him all the time anymore and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.

My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here? I'm scared as hell to do so and have it go south, but then again I wont be hanging out with him anymore so I wouldn't have to worry about it being awkward afterwards if it does goes bad. But what if it goes good? I've always wanted to hook up with him, like...bad, but I didn't want to lose my best friend here if it didn't go well. I keep going back and forth and I don't have anyone to run it by except the people in our friend group, which I'd never do. But since I know you guys might be able to relate or have some good input to add, I figured I'd try and ask for help here

Thanks guys!
(Please be kind in the comments)

Im in the same situation with my best friend. But I’ve known him for over 10 years now. And when he was living alone he would got drunk one night and asked me to give him head. I passed cause I didn’t feel it would be right. If i wasn't in the same level as him. And we’ve gone away on trips alone and he had offer me again to go down in him. And when i would try to tell him about it. He would act like nothing happened.
so if you feel like it would jeopardize your friendship maybe dont do it. But if it’s something you feel like you both want then go for it.
my friend is also straight and knows I messed with guys. He just gets this way when he drinks or if we smoke weed. But we both have mutual love for each other. And I’ve even thought about going all the way with him. And would let myself if the opportunity came

 

[Sunman_Universe]

Personally, I'd continue on with the antics and I'd let him know if he'd ever like to try something sexual (Deep kissing, BJ) that I'm up for it.
See how he reacts or comments. If he ignores you you have your answer.
If he tells you to get on your knees then do it!

 

[Dennissinned]

Gosh I'm jealous, I'd love to have a friendship like that. I became best friends with a guy I met on my very first day at university.
He was straight and knew I was gay. He was so gorgeous and funny, I fancied him so much that first year, when I was over it I told him and he was totally cool with it. Skip forward to the end of uni after 3 years of good friendship we was both moving home and we're weren't likely to see each other much after. Two weeks before I left I told him how truly gorgeous I found him and asked if he would fuck me. I knew he'd say no but I had to try. He let out a surprised laugh and had a huge grin on his face, he was impressed at my boldness and told me as much. It was a no though, I then asked him if I could give him a blowie and this very much tempted him. He took a week to think about it but still came back with a no but it didn't affect our friendship, we still talk over the phone and texts. Your guy sounds much more likely to say yes given the kissing and hugging.

 

[mattlovescock]

Okay so here's the sitch guys...

My best friend (let's call him Adam) has always been giving me confusing signals. We've known each other for 2 years so far and we get along great. Like, really great. Our personalities are completely the same. He's one of the best looking guys I've ever met, but he's straight. There's never been an issue or embarrassment for him that his best friends gay, and I've always loved that about him and his confidence. A jock and a gay guy being best friends can obviously be considered "incompatible" in societies perspective. The thing though is that starting 3 months ago, when we would hang out at his place or mine, and we would start drinking together, his personality almost does a 180. He always get very touchy, he's pulled my face in and kissed me a bunch of times randomly (because he thinks it's funny), he's wiped out his dick a couple times out of now where (soft), he always starts complimenting me on how good looking I am, and then when we finally good to bed, he loves to cuddle with me. (Like, he pulls me in hard) When we lay together though he never gets hard at all or even a chub, so it kind of seems to me he really just likes the comfort of it and connection.

I've never initiated anything myself though and have always just gone along for the ride because I never want him to feel uncomfortable since he identifies as straight. He also says when we're drunk that he'd never do anything like this with anyone else except me because he feels so comfortable around me. When we're sober though, we never talk a peep about it. Like, not one word. Kind of like it never happened in the first place, but then when we drink again together, it's back on.

I'm moving back to LA next month because my lease is up and I'm bored with Palm Springs, so that means I'm not going to be hanging out with him all the time anymore and probably wont be seeing him for a good while unless he comes to LA to hang out. I'm staying with him for my last two nights here in Palm Springs, and then I'm gone.

My main question or thought that I need input on, is if we start drinking, should I go for it and initiate something my last night here? I'm scared as hell to do so and have it go south, but then again I wont be hanging out with him anymore so I wouldn't have to worry about it being awkward afterwards if it does goes bad. But what if it goes good? I've always wanted to hook up with him, like...bad, but I didn't want to lose my best friend here if it didn't go well. I keep going back and forth and I don't have anyone to run it by except the people in our friend group, which I'd never do. But since I know you guys might be able to relate or have some good input to add, I figured I'd try and ask for help here

Thanks guys!
(Please be kind in the comments)

Please keep us updated!

 

[Jarren.Anthony]

Please keep us updated!

I definitely will! It's not going to be until New Years Eve, but it's been on my mind recently ever since I decided I wanted to move back to LA so I'm prepping a head I should've mentioned it'll be New Year's Eve too. I dont know if that means anything extra but I feel like people end up getting wild on that night, lol.

 

[Im23XXzz]

Straight bros can be very affectionate with each other. Hugging and being playful, even naked or in a homoerotic way are pretty common among jock types. That doesn't mean he's gay or bi at all. It just means he sees you as as his bro, as one of the guys. Personally I wouldn't recommend trying to initiate anything more unless you're willing to possibly ruin your friendship. (I doubt he'd drop you altogether, but if you make him feel uncomfortable you might just grow apart)

Just think of it this way: if he is bi or interested in experimenting, and he's interested in doing that with you, he will try to initiate. If that happens you can just be completely receptive to it and see where it goes. The upside of this approach is that you'll feel great if it actually does happen - you won't have to worry about feeling you 'tricked' him or if you did something bad that damaged the relationship.

 

[Kanashi]

Straight bros can be very affectionate with each other. Hugging and being playful, even naked or in a homoerotic way are pretty common among jock types. That doesn't mean he's gay or bi at all. It just means he sees you as as his bro, as one of the guys. Personally I wouldn't recommend trying to initiate anything more unless you're willing to possibly ruin your friendship. (I doubt he'd drop you altogether, but if you make him feel uncomfortable you might just grow apart)

Just think of it this way: if he is bi or interested in experimenting, and he's interested in doing that with you, he will try to initiate. If that happens you can just be completely receptive to it and see where it goes. The upside of this approach is that you'll feel great if it actually does happen - you won't have to worry about feeling you 'tricked' him or if you did something bad that damaged the relationship.

wow, that is amazing advice!

 

[deleted18388141]

Straight bros can be very affectionate with each other. Hugging and being playful, even naked or in a homoerotic way are pretty common among jock types. That doesn't mean he's gay or bi at all. It just means he sees you as as his bro, as one of the guys. Personally I wouldn't recommend trying to initiate anything more unless you're willing to possibly ruin your friendship. (I doubt he'd drop you altogether, but if you make him feel uncomfortable you might just grow apart)

Just think of it this way: if he is bi or interested in experimenting, and he's interested in doing that with you, he will try to initiate. If that happens you can just be completely receptive to it and see where it goes. The upside of this approach is that you'll feel great if it actually does happen - you won't have to worry about feeling you 'tricked' him or if you did something bad that damaged the relationship.

Listen to this guy!
good advice here

 

[deleted12954231]

Not to get all self-help with it…but you sound like a great guy and you deserve someone who is comfortable enough with their sexuality to make it 100% clear that they want you, all of you, with no mixed signals.

 

[halcyondays]

Amazing how alcohol lowers inhibitions isn't it?

This is way past your two day deadline but here goes.

When you cuddle he doesn't get hard. Meanwhile you're doing everything you can to avoid getting hard.

To me it seems unfair to you that he behaves the way he does knowing you're gay. It's not something I have ever done or would do to a gay friend.

He needs to know. Tell him. Set boundaries. An alternative is let yourself get hard with him. He's doing what he naturally likes. So should you. He ignored it once. See if he responds differently if you get hard every time you're pressed together.

For myself I keep close friends platonic.

 

[nhguy78]

Remember that alcohol, if intoxicated enough, removes ability to consent. Be sober so you both know what's going on. For me, snuggling and affection isn't ever sexual. I love body contact. Then again, I'm asexual but I'm also in a homoromantic marriage.

 

[C4junG0n3_BAD]

I'm an old guy. I've been around the block more times than I care to reveal. Ask yourself this...How much does his friendship mean to you? The reason I say this is, once you introduce sex, it will change. I cannot predict how. Neither can you. Sex invariably changes everything in a relationship.

The other thing is straight guys aren't thinking the same thing you are thinking when they do this kind of crap. I've had this happen a few times. It is really better to ignore it. Either that or laugh it off in a way.

I had a frat buddy do pretty much the same thing. He was a touchy feely guy. I'm not...period. I'm like a cat. I don't like to be touched except when I want to be touched and I'll let you know when that is. He was a handsy, slap ass dick grabbing jock. His thing was to get some guy in a headlock and lick his face...YUCK! This behavior was definitely more on display went inebriated.

He was the guy on spring break that would teabag guys or sit his naked ass on your face while you were sleeping on the couch or something like that...a real piece of work. Physically he was not a bad looking guy. He had a slammin' body and had really really nice boys. Everyone saw them ALL THE TIME!

I'd had enough at some point one night. He was doing this rubbing his crotch all over by butt. He did this frequently as well. I just turned around abruptly looked him right in the eye and said if you do that one more time, I'm going to suck you off and eat your cum and call your dad and tell him about it. I was very serious looking while saying this. His face froze. Then he laughed and I laughed and the other guys in the room laughed. So did it stop him from doing it? No. Did it stop him from doing it around me? Yes.