When I read your original post, I thought you two were like early twenties or something,
More on that later….
I like a lot of the practical advice
@Brodie888 gave you in his perspective too. But I’m getting a little bit of a different read and just thinking there may be some other angles to consider….
For starters, I’m not getting homophobia at all. To have such a tight friendship with you for so long and being so supportive as to help you come out to your parents sort of shuts that down.
But this is the part that is most puzzling for me: He’s talking about girls he’s been with and porn -with you.
A lot to unpack there.
Let me share a bit about my experiences with my long-term buds. I promise to bring it back to you and why I think(hope) it’s of relevance to your situation.
While every friendship is different there are some commonalities. Since we are naturally sexual beings, anyone who is a good friend is likely one that we have talked or joked about sex with if that is indeed a thing we do. I have a number of buddies that send me nsfw texts religiously, and I salivate, comment and return the favor of course.
Now, I am married as are most of my buddies so we mostly talk about how much we AREN’T getting any/enough from the wives, lol. But I can remember being about your age and having conversations like these about the kind of sex I was having in with more random women. And as I think about that time period, I can’t recall ever having sexual conversations like that with my gay friends. Admittedly, I have never had a gay friend so close as to be ‘best’ friends with.
He’s(your friend) also doing such intimate things with you i.e. the movies, going out for beers… Don’t get me wrong, I’m not saying intimate in any romantic sense, I’m saying those are not activities you do with someone you aren’t very comfortable with being around.
Finally, and most paradoxically, is his talking about his sex life and porn with you. For him to open this door and let you in it tells me he is more comfortable with your sexuality than you realize and likely he wants to admit.
Because every time he opens his mouth to talk about his sex life or porn, there is a part of his brain that reminds him that you are his gay best friend. And yet he proceeds to open up that sexual conversation anyway.
If you ask me there’s a part of him that gets off on telling you these things. And I’m not saying he’s attracted to you or anything like that. But look around these pages..Many men just love to be revered for their sexual prowess and some don’t mind where the admiration comes from.
You guys are embarking upon an age where most people have either gotten or are very close to getting married and have or are having kids. And even if not doing those things, for most people during this period childhood friendships begin to fade out and those that remain have the potential to be lifelong bonds.
As I said, I like the guidance you’ve been given above. A less formal approach might be to have your bud over for one of those beer drinking sessions you’ve alluded to. I’d caution not to go out necessarily and don’t get too drunk. Just a regular night hanging out doing whatever you guys normally do.
But at some point if he starts talking about his sex life then just kinda be natural and casually add some nuggets of your sexual experiences. If he starts to seem uncomfortable, bring that up too. Don’t make it accusatory though, just ask why can’t he talk about your sex life if he’s so open about talking about his. Tell him how it made you feel in THAT particular moment using just a few simple sentences and see what happens.
And what you do from there would be up to you. But I say just talk about it. Casually and if you can throw some jokes according to the usual cadence of yours and his conversation, do that.
Again, if you and he have the type of friendship you believe you do, this may make it awkward for just a bit, but ultimately stronger and likely even closer as buds.