Hi Doc.

lol I remember you posting the original topic...close to a year ago now, I think? lol I could've sworn this was the same topic at a glance.
Anyway, being physically ready is good, of course, but I would think the majority of it is mental, which to me sounds like you have some reservations on. I don't think you have anything to fear as far as the pessimistic outlook goes...I don't think you'd end up crying unless he was hurtful or inconsiderate of you. I don't know him well enough to call on that, but knowing you, if you're with him, I'm going to assume he's a decent enough guy.

Ending badly is...subjective. Usually, one's first time, as I'm told, isn't usually a stellar, mind blowing event in the practical sense. It is, done "right" (which knowing you, you hold the prospect of your first time in the same light I hold my own, so "right" being subjective), a special occasion, and a treasured memory. It is, after all, a pretty major life milestone. But it's not as "good" in the physical sense as, say, your 15th time, simply because you don't know each other and what the other (or yourself, in some ways) desires.
But emotionally and mentally speaking, which is what you're inquiring about, you'll know when you're ready...I'd tell you that in a way (and not at all to be harsh) if you're asking us, that's a sort of indication in the negative, in its own light way.

You mention that a potential detractor is you feel you don't know him well enough...why not wait, and fix that problem? Give yourself enough time to get to know him, and be sure that this is the guy you want to share this with. If he really feels for you, he'll understand, and respect your decision. If he doesn't, and it's a "problem," then I'd respectfully advise you dump his (your word here).

Either way, if you have reservations, any, I advice waiting. I know an hour's distance sucks, believe me, but I don't think this is your only shot by any means.
That all being said, on the other hand, don't try to let it upset you so.

Granted, that's a textbook case of the pot calling out the kettle, but while being nervous is totally normal, but try not to let it weigh so heavily on your mind.

Don't plague yourself with all the negative possibilities of it. Some skepticism is great, sure, but you sound like you're worrying yourself to the point that if anything
did happen when you go to see him, you'd be too upset to enjoy anything, you know? I'd tell you that once you've addressed the issue of feeling like you need to know him better, and once you can really look in the mirror and say "Hey Doc, I'm ready!", just be safe and be happy.
That's my advice, anyway...that, and of course to bring protection, be prepared just in case, etc etc. All that.
And ouch...sorry about the Brazilian.

Gonna have to admit I'm not overly upset that I'll never know what those feel like. I imagine that has to suck though.
Anyway, keep us posted, and I hope things go well, however they may go.
Hugs,
Harley