Haha take care of those zits. That's a lot harder than it sounds. Through highschool I spent 2 years switching between medications until I finally found one that worked (after I graduated
).
Anyways, maybe some of the smoother guys here (which are not me. I get by purely on my looks and horrible puns
) could give him some tips on "chatting up the ladies". Or improve his game if you wanna call it that.
As far as a hooker goes, just don't do it. I know a lot of people don't really put much stock in their "first time" and all that shit, but do you REALLY want it to be with someone you had to pay? If anything, I'd imagine it would be even worse for your self-esteem, and plus there's a very good chance of getting VD, even with a condom on (herpes, for one, can be transferred relatively easily even with a condom on).
The fake vagina thing is up to you. I've never tried one, and I don't know that I will because I'm a sheep and there's a social stigma around guys who use toys to masturbate. But definitely, as far as actual sex, don't go with the prostitute.