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I want to have a sexual relationship with my straight best friend. How do I go about this?

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Question - (24 January 2007) 3 Answers - (Newest, 24 January 2007)
A male United States age 41-50, anonymous writes:

I'm straight (slight bi tendencies but I prefer women)and I have a straight best friend named Adam who I've been having sexual fantasies about since we were in high school. Lately, I have been doing it more and more frequently. We have both been with only women but a mutual friend once told me he had a sex dream about me. I would love to turn our relationship into a sexual one. Can this be done? How would I ever approach this?

Sincerely,

confused

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A male reader, anonymous, writes (24 January 2007):

Hey confused, I have your answer, All men think they may be gay at some point. There is too much social pressure and judgement not to. having been with a guy as well, I prefer women but have been there. He and I were hanging out as we usulay did and started to talk about all maners of things. if you start talking about gay sex with a guy be non-chilant. Tell him about an instance where you saw two men holding hands, his reaction will be all you need. He will most likely say something homophobic, but that just tells you he's confused too. in time he'll come back to you as his confidant on the matter, and you can go from there with the more direct issue, but let him come to you. The problem is if he's curious and decides after not to stick it out or it isnt for him are you going to be ok with that?

oh, and it wont take more than a few days, the curiosity is murder.

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A female reader, smeedle United Kingdom +, writes (24 January 2007):

smeedle agony auntWell this is difficult as you are best friends and to all intents and purposes "straight" and I usually advise against best friends what ever sex having sex as it is a sure way to ruin a friendship.

Lots of us dream or having sex with someone we are close to and sometimes that can be the same sex as with you and maybe you are drawn to him sexually and him to you but what are the consequenses of finding out, he may not feel the same and then the frindship is over as he will be thinking you are after him etc.

If you really cannot get this out of your head then why not have a few drinks with him and ask him if he has ever had sex or wanted to have sex with a man and tell him you have thougts about it but dont tell him it is him you dream about, so dont have too much beer!!

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A female reader, Amethyst United States +, writes (24 January 2007):

Amethyst agony auntWow... you're in a sticky situation. If your friend gets freaked, that could be the end of the friendship right there. It's natural from what I know to be curious, especially with someone so close for so long.

My suggestion? Drop hints! Subtle, short, but honest hints. Say... ok, I can't think of an example, but when a moment comes where you can slip a comment, go for it! Do you two drink? If so, maybe one day drink with him, but not to the point he's vulnerable. Drinking a little seems to make the truth easier to slip out, and if he does indeed share your curiousity, it may slip! I'm really bad at this, because I really don't want to give you the wrong advice and have ruined your friendship.

Other approaches would be... asking him if he ever thought about becoming bi, or start talking about dreams, or even get that mutual friend to ask him questions. Then there's always the blunt and to the point approach, where you tell him your feelings... but that's waaaay risky. It all depends on what type of person you are. Hopefully someone can give you better advice than me... best of luck, I hope it turns out alright!

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