i was like 21 i think. i know i had a couple of drinks first but i drank before i was of legal age so i cant use that as a guage.
she was about the same age as me.
although i never did it before, i didnt care. it was fun to experiment and i think we both learned a lot from that. ultimately she left me for a guy.
as for being with someone much older, no, i dont think thats necessary or better. just be with whom you are comfortable being with. if you are comfortable with them then you will enjoy it. if not, then you wont. to me thats a whole lot more important than fancy positions, moves or multiple orgasms or what not.
with my current girlfriend we dont even have sex at all. we've been together as friends for 3 years and now as a couple for a few months. we've kissed, cuddled, ive sucked on her fingers and toes, shes massaged my feet. shes a bit messed up about sex from some past experiences that were really bad. but you can be very intimate and sexy with someone without sex.
i have come to the conclusion after a number of sexual encounters that would rather hold hands with someone that i love and cherish than to have crazy wild sex. and believe me, its not that i dont love sex.
no, i dont know anyone whos been to a hooker for their first time. i mean, i guess i might. its not something that would occur to me to ever ask someone.