I have popped a cherry in my civvie life, but never as a provider.

I have been asked to several times. I have always said no.

I am not against it completely, but in those particular circumstances I felt the gents were too young and too impressionable to give up finding sex with someone outside of the hobby first. I did not want to spoil them with my menu to the point they couldn't have fun with a young civvie girl from the get go!

If someone was say late twenties, painfully shy, or suffered from other reasons that I felt their chances of engaging successfully with a civvie were not in their best interest, then I would definitely consider it.

For me, I would take the whole picture into consideration (as much as possible) before saying yes.