Boundaries of Friendship?

[Jonamo]

Since I've been home from college for the summer, I've been hanging out with two of my closest friends that live in my hometown, let's call them 'Kyle' and 'Mark'. I finally had the balls to come out to them (they knew I was questioning but I never told them any more) and they both took it really, really well. I've known them both for at least 8 years and I consider them as close to me as family, but even with that I've had somewhat of a crush on 'Kyle' since high school.

Now after telling them about myself, we were hanging out enjoying some adult beverages and 'Kyle' said that if we ever did anything sexual that it wouldn't jeopardize or disrupt our friendship (the conversation came up with me saying I wouldn't want to risk a friendship over some physical actions of one night). 'Kyle' is one who I would call straight but extremely comfortable with himself. He has on numerous occasions shown us his dick just to show it off (and still will do so even knowing about me) and he is very open and comfortable talking about intimate details about my sex life. We work out together now every day and have become as close as we ever have. He complains about the lack of attention and lack of specific sexual acts from his girlfriend, and then makes obscure comments about how since he has a friend like me those things should get done.

Where I need help is whether or not to actually pursue anything here. I've thought about it for awhile but I'm just not sure it would be appropriate to do. I know if the situation comes up while we're both intoxicated then something may happen, but I'd like to at least think about a plan beforehand. One thing he told me was him and his girlfriend both have slept with other people, but are still in love with one another.

Any advice or ideas would be appreciated!

[Gravity]

Hard to say - on the one hand, he may just be really "straight but not narrow." On the other hand, this could be his way of using you to explore his own attraction to men.

First of all, if he has a girlfriend, then that needs to be cleared up before you do anything with him. Have you confirmed the situation with her? It's one thing for him to say "she won't mind," but a different one entirely for her to say "I don't mind."

Secondly, it seems if "Kyle" has been spending more time with you since you came out to him, he may be seeing a sort of "opportunity" in you. Did he actually say that "since he has a friend like" you his sexual desires should get taken care of? To me, that sounds disparaging - as if you would naturally be prepared to provide him this "service" simply because you're gay (which I'm assuming from "Kinsey 5ish"). Gay people have emotions too (gasp!), and of course they enter into our decisions in relationships and sex.

Finally, and most importantly, if you're already having thoughts that you're unsure if this is appropriate, then I say listen to your instincts. You know your friend, and you know yourself, and if you're a little less than thrilled at the idea, there's probably a reason.

[cscipio]

I agree with Gravity.

If you were a fiction novel, I'd be thinking "lucky bastard", but realistically, there's potential for quite a bit to lose.

If Kyle and his GF were swingers and she was fully ok with him seeing other people (gender shouldn't matter in infidelity) then you've removed the ethical issue and it simply comes down to "can your friendship bare it". So, ethics aside, assuming you can give him a blow job and then go fishing or out for drinks right after and feel comfortable with yourself and him, go for it. Otherwise, I'd refrain despite the temptation. I wouldn't hold it against him and if he's tempting you too much, you should just say, in a friendly way, "We shouldn't do it - even though you'd be fine with it, it makes things too muddy in my mind - I'd have a problem with it."

I had an intoxicated 'event' with a straight friend. I have a moderate foot fetish and he and I were discussing it, drunk, I came onto him pretty hard. He let me massage his feet, I kept it non-sexual but still felt very akward about it the next few days. He's perfectly fine with it, and while I'd love to do it again, I don't know if I can emotionally handle it even if he treats it as "simply a massage", I'll have a lot more going on in my head.

Hope that helps.

[Chip]

I'd go so far as to say that Kyle is probably not quite so straight as he might claim.

However, the points made by the other posters I completely agree with. Kyle is in a relationship and it would be wrong for him (and for you) for anything to happen between the two of you without her express advance knowledge and consent. Even there... it's a little iffy.

"Friends with benefits" arrangements can work, but very often, one party or the other starts to have feelings and that complicates things. So I'd suggest having a long conversation with him. If he were to own up to being, uh, other than completely straight and wanted to pursue something with you more than keeping his current relationship, that's one thing. But simply using your friendship to get himself off... and not keeping his gf in the loop... definitely not cool.

[Ianthe]

Your friend is definitely moved out of zero on the Kinsey scale by his expressed desire to have sex with you.

Regardless of anything else, I think this would be a bad idea because you would almost certainly develop stronger feelings for him.

But without the girlfriend's consent, it would definitely be wrong.

Also, if you DO end up going through with this, I think you should insist on reciprocity.

[Lewis]

I agree with the others that it's probably not the best of ideas. I only kissed (just a little peck on the lips) my best friend and it sent my emotions into overdrive, which isn't good at all. But, if you like this guy and you both want to go for it, I don't see why you maybe shouldn't. You should definitely talk about things first.

I know that if my best friend wanted to do things with me, I'd probably (naively) go for it. I've spent most of my teen life not doing what other teens my age are doing and to be honest, I need to experience! Just be safe I guess...