Assuming the lad is old enough that it is not statutory rape (17 in Texas) would you or have you been the first for a young man? Is the answer any different if he (or she) is making the arrangements versus his/her dad/mom (perhaps someone you already know) making the arrangements?
Just curious. I don't know about others, but I definitely had the fantasy of being initiated into sex by a kind and knowledgeable and beautiful older woman (which I probably thought was 30 then LOL) when I was in college (did't actually have my first time until 21).