Scared of scaring someone away

So, to keep the backstory as short as possible, I’m a gay guy who fell in love with one of his best friends, in a twist of fate, he’s actually bi-curious and would like to try to have sex with me. However, there is one thing that I’m scared might turn him away, I’m fairly hung and he is a virgin (at least in the gay department) and neither of us are that experienced, so I’m terrified of the possibility I might end up hurting him and drive him, what should I try and do?

Tl;dr: I want to have sex with a virgin and I’m scared I might hurt him.


  1. First piece of advice is not to use porn as a guide.

    With that out of the way, the most important thing you can do is to communicate well. Make sure you are both comfortable at all times and do not push further until you’re sure you are both ready.

    Use plenty of lube and I mean PLENTY. Encourage him to have an enema beforehand ( so he’s relaxed and not worried about making a mess. Take your time getting into it. Eat his ass, loosen him up with fingers slowly (make sure you trim and file your nails!), massage his butt and the surrounding muscles with your hands. Not sure if you mean hung thickly, or lengthy, or both. If you’re thick definitely make sure to go slowly as possible, if you’re long don’t push in too far, just a little bit at a time.

    And if either of you feels uncomfortable or something hurts, then stop and try again another time. Listen to your body and listen to his. Watch his face. Learn to recognize when something is uncomfortable for him because he may feel uncomfortable saying anything. Check in frequently.

    And of course most importantly: have fun.

  2. I second everything the other guy said. Being a well-endowed guy sometimes we have to take things slow. Or better yet, if your verse offer to flip with him. The best tops, that I have experienced, have at least tried bottoming so they are in tune to what the bottom is feeling. Different positions work well too. For me, my pleasure comes from watching a bottom get off while I’m inside of him.

  3. Also remember there’s plenty else to do other than penetration, for pleasure & getting off; especially if it’s his first time & you both have little experience.

    Talk to him. Ask what he’s curious about. What it is he’s fantasizing about with any guy & or you specifically. Share what attracts you to him too, if you feel comfortable. That’s always a good starting place. Let it unfold & heat up naturally.

    If you are that “big” and he wants to feel you inside him, you can let him start on top. This way HE controls penetration rate and his pain/pleasure level. And it shows him you’re considerate of his feelings & anxiety too. Once he’s comfortable and opened up, then try other positions.

    Most of all … talk, breath & just have fun!

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