So I have a straight friend that I’ve been buddies with for 4 years, we also roomed together at college for all 4 of them. He would always walk around in front of me in just his boxers and I realized he was super attractive. I eventually started fantasizing about hooking up with him and even had dreams about it.

He was always super nice to me and he knew I was gay, and we’d talk about it a lot. One time in a group of friends, he even mentioned that he believes sexuality is very fluid and that you shouldn’t “knock it til you try it”.

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I really would love the chance to do something with him. I could so see him being into it. Any tips or tricks on getting there, or topics I could discuss with him to pick his brain a little more about the topic!?

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3 COMMENTS

  1. just be prepared for what might happen if things go south.

    many a good friends have been lost over this exact scenario.

    might be worth it to just keep a good friend.

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  2. It’s tremendously risky but here’s a thing that happened with me:

    https://www.reddit.com/r/askgaybros/comments/azazan/my_straight_massage_therapist_became_my_friend/

    My advice: find a way to let him know that you are game if he ever wants to try anything out, and then forget about it.

    Let him be in control of if/when anything happens. It might be right away, it might take a few months, and it might be never.

    Then enjoy the friendship you have right now and realize that what you have is already a good thing.

  3. I’d suggest staying within your own league. There are enough cute gay guys out there, no need to branch out. But do what makes you happy, just be prepared that you are potentially risking a 4 year relationship

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