When to tell someone . . .

[Stratos]

       I've met this really nice guy online, and we've gotten along marvelously there and on the phone so far. I've given him some pictures of me clothed. We are planning to see each other this summer. Yes, I'm gay.

       There are issues with my body, and I've told him this, but I've not singled out gynecomastia. When should I do this? I'm worried he will  be disappointed with it. If he is, is there anything I can do? Thanks.

[WishmasterK]

Well that depends on alot of things. Definitely before any intimacy. I would sway the conversation towards it when you are having some meaningful conversation. And just come out with it. I think it's important to show how much of a "big deal" it ISNT. Usually the more importance you put on it, the more the other person will. If he has questions answer them to your best ability. And if in the end he cant deal with it, move on.

[Stratos]

       I'm concerned about him not being able to deal with it. He's by no means shallow, and because he's still willing to see me after the pictures I sent, he must have some tolerance for looks. The question is how much. Everyone has their own line of what is and is not acceptable. I just feel I am so far along, he may not be able to tolerate my chest. This I understand - he wants someone to actually think of as attractive. What does one do with someone who finds such a large portion of you unattractive? I would be devastated for not being able to make him happy.

[Teflon]

seems there are three possible scenarios
either he will find them unattractive and a deal-breaker, or
he will declare them molehills that you have made mountains of, or
he will realize he LIKES them (and that he likes you with boobs)