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I want this guy...

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Well to me it seems pretty obvious that he isn't totally straight and that he somewhat knew he could get you to do things. I think you should see what he thinks about homosexuality. you can either one come flat out and tell him that you like him or 2 beat around the bush keeps messing around with each other as "Straight" friends until one of you admits there something there. Good luck cause like you I fell head over heels for my best friend and all he has done is play with my heart saying he loves me and what not and throwing girl friends in my face. Lame... If he starts playing with your heart and emotions don't hesitate to shank a bitch!!
 
Oh but yes i agree slow down with the sucking his dick and what not. Well i think you shouldnt rush this situation take it one day at a time you know flirt a little here and there. I hope for the best.
 
my advice is don't push him...don't tell him you're gay and just let things happen...if you want something specific to happen just throw hints in that direction...u re his best fiend so you know pretty well how to steer him in a certain direction.....as long as he keeps thinking he's the one that's coming up with these ideas he won't get scared
 
you'd really want to think this through. Find out first what he thinks of homosexuality. This would be your starting point. Then ask yourself if you're ready if the probability of awkwardness and the rift in friendship comes after the sex.
On the other hand, build it slowly and let him know with hints that you are ok with everything related to messing around. it'll be his choice then. Keep him horny and you'll get it somehow. Goodluck!
 
[FONT='Verdana','sans-serif']Well if you want his penis than you gotta work your ass in front of him show him what you got but not in the whole slutty way. Blah I feel ya my best friend was on our high school football team and was the big macho straight guy. Psh lets call him Alan well let’s just say when me and Alan wrestle it never ceases to turn him on . So my suggestion is try to wrestle him and when you wear his ass out pin him and take it from there. If you feel something poking you than take it from there and be like I wonder why gay guys like it up the butt. Make up some shit up and go with the flow. Like the others said just let it happen cause nine times out of ten when you try to plan something it doesn’t always go the best. So let love happen..|[/FONT]
 
The two of you are young, curious and horny. If you want to play around and explore, then enjoy it.

Just make sure he is as interested in getting you off as you are interested in getting him off.

The only caution is that if the two of you don't know whether you are gay or straight. Keep in the back of your mind the possibility that someday he may outgrow your boy-boy playing around when he gets himself a girlfriend. Then you'll be left with no one to dry-hump, suck off or play xbox with.
 
>>>I don't want to actually tell him I'm gay. I just want to approach slowly and then I'll tell him.

Dude, he knows. Straight guys don't offer to give blowjobs to their friends for five bucks. But he seems agreeable to it all. Enough that he's reciprocrating on the hand jobs, anyway.

Just keep enjoying the play, and nudging him forward.

"I really liked messing around with you last week. Any chance we can do that again?"
"Could I suck you off again? That was kinda fun."
"Any chance you'd return the favor? If not, another handjob would kick ass."

If you encounter any resistance from him, back off, say "that's cool", and stay in that spot for awhile.

Lex
 
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