This is not my proudest moment. But part of me thinks, "so what? I've got money; he's got time, let's do this." I've never been with another guy before (I'm 26 and was a closet-case until just this past year). I think it would be helpful to be with a guy for the first time where there was nothing at stake--no feelings, no possible relationship, no pressure, etc. It could be...educational?
Hell, I'm not even sure I'd have sex with him. Part of me just wants to sit across a restaurant table from a hot guy for a few hours. Has anyone here hired an escort before? (There have been old posts on this but I wanted to get current feedback.) I know the legality is tricky in most states/countries (which is why I'd probably just opt for a massage).