He won't necessarily regret it, GayUSAsian, but it might not be the romantic experience that he is hoping for... If he's only wanting to get sex, then maybe it'll be good sex. Who's to say?
1) It depends what he's looking for.
2) It depends how far he's ready to go.
3) It also greatly depends on how good the stranger is with breaking people in, or with dealing with their new partner's needs.
I thoroughly second TLC's advice to make it a safe experience, so who says ''safe'', is actually saying ''come prepared''. Take the condoms, bring the lube, champagne, candlelight, chains & cufflinks (er...?? maybe not those! :tongue
whatever... and make it a safe experience for you both, come what may. It's not as if you'll become pregnant, but some other things are out there that are a bit nastier.