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Sex with friends

BearMagus

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You could try popping in a skin flick on your vhs or dvd....a good bi flick would best. Then take it from there. You can ask leading questions or start picking his brain over his thoughts. You know your friend best. If he has ever expressed any homophobic attitudes, I would stay clear.
 
I'd say it depends on how much you value the friendship. Even if he says yes, chances are good that the relationship may alter quite a bit afterwards unless you two are both utterly cool and secure with yourselves. Judging by your post, you're not. Personally, I'd skip it.

Lex
 
but your username says penislover?? are you sure your not sure
 
Think this one over.

He is one of your best friends.

You must know him well, rite?

The chances are that you also ought to know the best way to approach him on that, ehm, 'sensitive' matter.

All a bunch of other, unrelated guys here can do for you is:

1) Tell you to be careful and not ruin your friendship.

2) Use alcohol with a sense of moderation??? (What's moderation here?)

3) Talk sex and watch some sort of a porn dvd?

...

So, you are getting a picture?

Come up with something a bit better, coz u know the dude. So, you also should know how to put your moves on him.

SC
 
Just my opinion but I would pass on it. I have an unwritten rule that I don't have sex with my friends. In the past, I did a couple times and it DOES change the friendship in ways that were not good. If you are seeing someone, dating, having occassional sex and become friends, that's different. That's usually the path to a relationship. But just to have sex with existing friends, as an "experiment", never worked for me. My real friends are more important to me than sex. They are like "family". We don't see each other sexually.
 
To ask someone something 'in a way that he will say yes' is not friendship - it's manipulation. He's a best friend, not a sexual object or jerk-off fantasy.

The way to approach it is to say what you want without putting any pressure or obligation on him. For example: 'I keep wondering what it would be like to give a guy a blowjob and I'm thinking of experimenting.'

I think it's probably true to say that most gay men are pretty clued up on their own orientation without having to do any experimentation. Erotic fantasy during solo-masturbation is a pretty good indicator.

By-and-large straight men don't have sex with other men; that's what defines them as 'straight'. Until you're completely comfortable with your own sexual orientation - and the fact that you can't talk about it to your best friend suggests you're not - it's probably best to let sleeping dogs lie.
 
Well, a lot of this sort of thing is also determined by age. If you are under 18 [and breaking the law by being on here mind you...] then this could be something that he might be interested in.

Best chance for this kind of thing is while you are still in your teens, and maybe early EARLY twenties.... but who knows. Anything can happen. Just dont try to manipulate him. Just try to set up the situation where it is possible to happen, and let the chips fall where they may.

As for not being completely sure of one's interests.... I myself am still figuring that out [I'm only 19 afterall]. So, assuming that you are younger like I am, we both have time to figure that out. I think I am about figured out [mostly straight, but a decent helping of curiosity.... I am very happy with my girlfriend at the moment, and I just dont "connect" with guys the way I do with girls.... but penises are very nice all the same. ]

But this isnt about me, this is about you. Just dont fret about it. If you really want to have a shot at this, then put in a skin flick, read his body language, then go from there. Trust your instincts, and try not to ruin the friendship by trying to push him into this.
 
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