First time with a girl was in high school. I think it was my junior year of high school. Still friends. It was actually alright, you know I'm a gay guy. I don't know how she enjoyed it or if she enjoyed it as much as me... First time with a guy was actually not until I was 25, after I came out. Super awkward. I mean, can you imagine dating and hooking up with a guy after your coming out, after 25 years? I'm sure he was like, 'What is going on?' I think I've gotten a little better at doing all that stuff so hopefully those embarassing moments are over.