My best friend has me so confused

[A_michael90]

This is 100% a true story.. But to give a bit of background, him and I have been friends now for over 20 years. We grew up together and for as long as I can remember, I've always had the biggest crush on him.

We all know the stories. Gay boy in love with his straight best friend. But nothing usually comes of it.

I was very open, so he knew I was gay and never gave me an issue. We've remained best friends for years and l've been there through is many (straight relationships). He use to live with me and would bring girls home to bang one room over and I use to jerk off to them getting it on. Always had the biggest crush on him and a few years ago after a day out of drinking, we were texting and I jokingly said something about a nude pic and next thing I know, he sends one through and oMG was it BIG. Never have I been more turned on until that moment, just finally seeing what I have always wanted.

Over the years, he would slowly send me more pictures if l'd ask. I'd usually wait until he'd snap me, id see he's out drinking so I would know he was a bit loosened up and now l've gotten about 10 pictures and videos of him and they're getting hotter each time. More frequently too.

I finally got the courage the other day to ask when I can see it in person and he responded "whenever". I told him l'd love to get my hands on it and he said any time. He said he assumes guys can give better head, so he'd be down. Idk if he's just teasing me or what but now idk what to do. We live about an hour apart so I don't see him often. Oh, that and he has a gf. So yeah... it's been an interesting few weeks as it's built up more

Anyways. Thoughts on if I should pursue?

 

[i-feel-fantastic]

If he’s up for it, then go for it. But wait until he’s single.

 

[s0undbw0y]

you're not confused, and neither is he. he explicitly told you that he's curious and gave you an open invitation to suck his big hard dick.
you sound nervous, anxious, and a little scared. all good signs that will make it 1000% hotter when the moment finally ...comes.
just find out what specifically he would be ok with happening, if he is open to reciprocating or eventually exploring further, and if he has any hard boundaries.
then keep yourself busy for a bit while his fantasy marinates, then after 2-3 days casually hit him up (without hinting at anything) and let him know you actually have to be in his town in a couple days for a "work thing" so he should come pick you up (at the cheap hotel that they're obliged to cover) to go grab lunch together. he shows up, you're just done showering, then strike a match on the fantasy that is boiling over by now and see what happens. right before you chug his cock you can say something chill like "fuck this is definitely worth the ## years i've been wanting it" but don't gush about what this means now and feelings and shit.
you both knew it was always going to end up here eventually, so keep it chill, have fun, and figure out a plan for next time.

 

[bigmanmikey444]

invite him over and have a glory hole set up lol

 

[Brodie888]

Invite him on a "boys trip" that his gf wouldn't be interested in going to. Or maybe a concert where you are that he can come stay at your place.

Share a twin share room and see where it goes. Or if at your place, even easier.

Most "straight" guys are fine as long as you reassure them that you know that they are straight and nothing more will come of it.

 

[colegialsafadinhah]

He has a girlfriend. Momentary happiness can make him unhappy for the rest of his life.

 

[CreamEggOmlette]

As much as I would love to say do it and have fun (because I was the guy in college who blew all my str8 guy friends), be prepared to lose him as a friend. I know this sounds apocalyptic, but a lot of straight guys crawl right back into the closet the moment they nut. They can't handle knowing the fact that they let another guy suck and swallow their load.

 

[Moaningmike]

Because you two have been best friends for so long, and he made it clear he’d let you suck it, the best thing to do is talk everything out before you two do anything. Him having a girlfriend (especially if you know and like her) is a BIG issue, because no matter how you look at it, he would be cheating on her. If he feels guilty and tells her afterwards, you can just imagine the outcome. Some women are fine with their guy fooling around with a guy, usually as long as they don’t have to witness it. Then there are some women who like to watch two guys together. How serious is this girlfriend? You need to talk with him about what will happen after you blow him. Ask him if he can handle still being friends, will he find it too weird and awkward? Will he be able to still be your best friend when that line gets crossed? Tell him you want to do have his dick more than one time, that you’ll want it often, and can he be cool with that. Let him know that acting like it never happened is not a good idea. I haven’t been with straight guys since college because I need more than a guy giving me 30% when I’m giving him 100%. Ideally, I’d tell you to just forget doing anything with a straight guy and find a guy who REALLY wants you. Being best friends for over 20 years means he must have a lot of (platonic) love for you. There might be a chance that he has always been attracted to you but wanted to suppress that part of himself. He could be bisexual. The best thing to do is talk it out.

 

[Bwallz86]

Don’t do it. Fastest way to ruin a friendship, especially if he isn’t 100% sure of himself. You need to let him work out his feelings for himself. It isn’t worth potentially destroying a 20 year friendship.

 

[chrisrobin]

Theres only one way to find out and that's call his bluff. After all you have the evidence on the size of his dick you should just say you're willing for a hands feel and blow job any time he's ready.
He'll react one way or the other and the air will be clear.

 

[mitchellk]

you're not confused, and neither is he. he explicitly told you that he's curious and gave you an open invitation to suck his big hard dick.
you sound nervous, anxious, and a little scared. all good signs that will make it 1000% hotter when the moment finally ...comes.
just find out what specifically he would be ok with happening, if he is open to reciprocating or eventually exploring further, and if he has any hard boundaries.
then keep yourself busy for a bit while his fantasy marinates, then after 2-3 days casually hit him up (without hinting at anything) and let him know you actually have to be in his town in a couple days for a "work thing" so he should come pick you up (at the cheap hotel that they're obliged to cover) to go grab lunch together. he shows up, you're just done showering, then strike a match on the fantasy that is boiling over by now and see what happens. right before you chug his cock you can say something chill like "fuck this is definitely worth the ## years i've been wanting it" but don't gush about what this means now and feelings and shit.
you both knew it was always going to end up here eventually, so keep it chill, have fun, and figure out a plan for next time.

What a slut. This is a great plan.

 

[Olivander - make the wand Great again]

Sry for mistakes - english not my mother tongue, and i try to learn without translater.

Hm u need to understand what u want man from him and from yourself, and then u need take a one right for u way of 2 ways.

1) U save friendship, and ignore his request;
2) u going to get his hard cock but u fight of any methods with this gf for cock and friendship (glory) XD, it is not too hard if she in couple with him not long time and if she not a queen of cocksucking industry.

 

[678wsb]

Any updates?

 

[playklax01]

Some guys talk the talk, but can't walk the walk. They're all for it until after the event, then they turn all weird and avoid you. It's possible that could happen. It's happened to me before. It could jeopardize what you have now.

But based on what you presented, it sounds like he is more than ready to fool around. Between sending pics/vids and telling you 'anytime', he's likely been thinking about this more than you probably think.

Everyone's morals and ethics are different, so the whole thing with the girlfriend is something you'll need to consider. Are you ok being the potential side piece? Do you feel bad going behind her back? Is it his business to deal with, not yours? Things to think about and decide where you stand on the matter.