I could... but should I?

[contradict1self]

So let me start off with a couple of things.
1) I am EXTREMELY analytical.
2) I have yet to be with another man (as a long term relationship or sexually).
3) The man I am speaking about, though in all probability is bi from my observations, considers himself heterosexual? or at least when he is sober he is mostly so.

With that out of the way here it is. I have been friends with this man for about 14 years now. For the last 6 or so things have been getting a little strange when we drink together and no one else is around.

It all started after a friends wedding when we shared a room and a bed. We came in drunk from the event and drank even more (I brought a bottle of Absinthe back from Paris) when we got back to the room. So we pass out (or so I thought) at some time around 5am or so. I reawaken to find that I'm being felt up and his giant dick is rammed up between my little olive skinned butt cheeks (I still had my pyjamas on so nothing really happened). Anyway I froze like a hunted animal firmly grabbed his hand and moved it, he turned onto his back but I still felt movement. A bit goes by and I still feel him moving about, I tried so freaking hard to get to sleep and was totally unsuccessful. Curiosity got the better of me I turn over and he's jacking off, a little later he gets up and I'm guessing he finished himself off in the bathroom.

So later on, I move away and I end up coming back into the city for a music festival. I end up leaving the festival early because a friend of my friends [plural] is the most disgusting, obnoxious, pig of a spoiled little trust fund worm ever. Anyway he comes back to the apartment more than a little drunk and again we start drinking all over. This time he ends up grabbing me when we are out on the back porch and pulls me into him hugging me nuzzling his head in my neck telling me "I've missed you so much..You're really getting in shape, you look really good..." At this point I am kind of scared, kind of turned on, kind of sappy feeling. Oh by the way, this guy is huge like 6'5", I'm 5'11". So after all that was over with the usual drunk "I love you mans" we go to sleep again sharing a bed. [this is off topic but thought it was hot anyway] I wake up again and hes making these weird little noises in his sleep, so his dicks out totally leaking precum and hes rubbing it while hes asleep. It was so hard not to jack off or go inspect it a little closer.

Things like the above happen a couple more times when I come down to visit or we go camping. Fast forward to last year he bought a house. I went over to stay with him for a few days to catch up since we hadn't seen each other in about a year. Greeted with my usual bear hug we go out and get our drinking supplies go to dinner etc.[this is going to sound really awful but we've developed this strange habit of calling each other baby after watching Entourage, thus we probably look like a really weird couple in public]. After our usual binge drinking and watching Thank You for Smoking, he tells me his shoulder is acting up. He has a couple of old football injuries and I give fantastic massages. So I start working on his back and shoulders then he lays down and I start working on his legs. Before I know it my hand is up the sleeve of his boxer shorts playing with his dickhead. He was mumbling something while petting my back. About then is when I started getting really self conscious and stopped. He looked up at me and when the stroking didn't continue he gets up and walks away noticeably pissed (angry for those in the UK). We still end up hugging for some reason (we were drunk?) but go to bed in separate rooms. A couple days go by and it's time for me to go back home and when I am getting my stuff packed he keeps trying to convince me to stay for a while longer at least one more night. I left [story of my life].

It's been over a year since we've seen each other, but we remain in fairly close contact. We talk on the phone and cam etc. I get fairly bombarded with when I am going to come down again and visit. He keeps going on about how he wants to find a wife and that he's getting older.....

If any of you made it this far Thank You.
I needed to get this off my chest.
​

I really want to play around with this guy, I really love him but how? At the same time I am afraid I might get attached or that if we do anything that it will permanently screw up our friendship. Honestly I have never been with a man but have a weird want to blow him (still on the fence about whether I would do penetrative sex). I never even found him attractive until the last couple of years.

Thanks again.

Prof. Woland

 

[Seasoned]

You've had multiple opportunities to play and the next time you see him it's seems as though you'll have another chance. Your real question seems to be regarding what will happen next. That's not predictable, but it's apparent that should you have sex with him you will expect an on-going love-sex-romantic relationship whereas he may be looking to get off.

 

[Rolyo85]

Stay away from closeted people and people in denial. A golden rule to avoid drama.

 

[altlover85]

I would probably leave it alone, but if you do decide to do something, just leave it as a friends with benefits situation. From what you've told us, it doesn't seem like he's in any position to take this to a romantic relationship level.

 

[anchihiro]

Well he has pretty much given you ample opportunity to play around really. I'd say the rest is up to you.

And on behalf of people from the uk, we know what pissed means.

 

[chrisw87]

I think there was potential there to pull him out of the closet though it was a missed opportunity. With the gap in time that you've had it would be too awkward to bring that topic up straight away, you would have to re-kindle the friendship all over again.

He may be in denial, or in the closet, the latter would be easier to work with if you WANTED to, but it is all about what you want in the end, remember that.

 

[contradict1self]

Thank you everyone.

Mr. Anchichiro, I sincerely apologize, I was just playing around. Most of my cousins are over seas and we always confuse each other with the dialectal differences. Especially my cousins in Oz. It's almost as if we aren't speaking the same language sometimes not to mention they throw in their own Greeklish.

I really think that getting to know him any better would be ultimately disastrous.

Thanks again.

 

[Treborf]

You've already fooled around with him and crossed that line...might as well see it through. Once you've passed the dry humping/handjob barrier, there's no need to worry about the fallout from giving a simple blowjob. There's little substantive difference between all you guys' bouts of sexytime snuggling and actual sex.

What I'm saying is the next time you're faced with his hard dick, slip his boxers off and go to town.

 

[KaraBulut]

Sex changes friendships- even 14 year friendships. While this guy undoubtedly has feelings for you, the pattern is that the feelings are never expressed unless he's drunk and horny. Anytime they have to get drunk to express their feelings, it gives them the morning-after excuse of "Boy was a I drunk yesterday" and an excuse for resentment that a guy "took advantage of them" when they were drunk.

If you can't have a sober conversation with him about dry-humping your ass or how a shoulder massage involved putting your hand in his boxers, then chances are good that this is a bad idea.

If you want to play, pick someone who can be honest about it when they're sober.