so I really have no idea when my first time was.

I'm gonna choose to remember she looked something like this:

Best friend's fiance

So-called best friend's fiance!  It probably makes me sound pretty heartless but it was really just a bit of well deserved karma.  My friend's girlfriend found out that he was sneaking around with the girl I was dating at the time.  Needless to say, she made sure that any pain I was experiencing went away.  A true "Dear Forum" kind of night!  So much for their engagement.... (LOL!)

I remember my first time . . .

... I felt so alone.

(An old Rodney Dangerfield line.)

I have fond memories of my first time...

...it was with my crush from ages ago!

We actually lost our virginities to each other. During summer break, we spent the entire time biking, holding hands and experimenting a ton behind closed doors. Good memories.

Wow, a long time ago

I was 16 and sexual awkward, she was a 17 year old good Catholic girl (true story) with a lot of experiences that she didn't get in the church.  She went to Mass on Saturday after which I gave her a lot of new material to confess Saturday night.  We "went out" for about a year trying about everything we could think of, what a way to get broken in.

...we had just left summer band sectionals practice and were walking home and stopped in a little thicket of trees on the hill behind our Junior High School. We had preplanned this. We had the belief that a girl couldn't get pregnant if you had sex during her period so we had unprotected sex. We were both virgins and the sex was nothing earth shaking but remarkable because one's first time is unforgettable. Fortunately, she didn't get pregnant or we would have been parents at age 13.