We were both 17 and virgins. She was my first kiss but I don't believe I was hers. We'd been dating for a bit (a couple months?) and the makeout sessions had gotten hot and heavy. We were both very responsible and so when the time came we decided to be very diligent about birth control. We agreed that we weren't comfortable with just condoms so we needed to get hormonal birth control (ie. the pill). So she goes to Planned Parenthood and gets a pack and that's when we learn: you have to be taking them for a full cycle before they 'kick in'. This is not news that two very horny and ready teens wanted to hear. But we were responsible so we decided to wait the month...

Can't remember if it was in that conversation or very shortly thereafter we decided that oral was nice but we still wanted to take it further. Some conversation later and we decided to lose our virginity together... anally. I never really stopped to think this was weird at the time, but in retrospect she was really good, giving and game, even as a virgin.

Not knowing better (and this being pre-Internet days we couldn't just Google up a set of best recommendations), we settled on hand lotion for lube, which didn't go nearly as bad as you might think (I applied and reapplied it generously. We came to the mutual conclusion that it (and the month of anal following that) was a nice experience but that vaginal was even better.

Bonus followup story (for added naivety): Sometime during this month of anal, my girlfriend called me to tell me that it was urgent we talk, but that she didn't want to tell me on the phone. We lived a distance apart and went to different high schools, so that was going to be days at least. I was able to sit on that for about an hour before I conjured up the most ludicrous notions in my head, including the idea that I didn't understand female anatomy well enough and that I'd somehow managed to get her pregnant.

Fearful of this magical butt baby, I called her desperate to know what was so urgent that she just had to tell me but not on the phone, she admitted she had kissed her sister's boyfriend. Expecting a jealous wrath she seemed a bit surprised at my extremely relieved "Is that all?" response. I got her to assure me that she had no intentions of ending our relationship and I assured her that as long as we were good, I didn't really care.