Bad Boy was my first real boyfriend. We met in September of grade 9, I was 14 and he was a year older. He was also loads of fun, tall, and, from my 14 year old perspective, super hot. Because we attended different high schools most of our relationship was based on 2-3 hour phone calls every night. Regardless, I was smitten. He was also my first real kiss and it absolutely blew me away. Definitely a boy who knew what he was doing.
We crossed paths again when I was 16 and again at 18 where each time we had a bit of a fling (PG13 fling I must add). There were two incidences when I was 18. The first incident was just after my 18th birthday, we basically started talking again after many months of no communication. Somewhat randomly he asked me about my virginity. Now to give context to this, for years I had been telling him that I was waiting until I was at least 18 before having sex. I didn't know until after the fact, but he had made a mental note and it was his goal to be my first. After he asked the question, there was a bit of an awkward pause and I let him know that I'd given it up to my boyfriend. I was absolutely floored at his reaction! He was so angry and he basically told me off for not "waiting" for him! Somehow I managed to calm him down, but it was definitely a conversation that stands out in my memory.
The second incident was several months after this conversation and he and I had been hanging again. One night we were sitting talking in my car and one thing led to another and we both ended up naked in my car. It was a very hot make-out session but I had a moment of panic and stopped things. Once we were both properly clothed again I drove him home.We didn't cross paths again until I was 25 and he was dating my sister. That is a story for another day.
It's important to know a bit of the back story and to know that although I was not ready at 18 I had always wondered "what if?"...
Several weeks after The Ex and I broke up, I was alone at home over a long weekend. It was the Sunday night and I was sitting at home on my lap top with MSN running, which is unsual for me. Out of nowhere Bad Boy messaged me. We chatted for a bit and he kept whining that he wanted to see me. I live in Toronto and he lives in my hometown. Finally, I just wrote to him "Fine, I'll come home. Meet me at the bus station."
I knew exactly what was going to happen. I still wanted Bad Boy and this was my chance to check him off the list. Not only was I excited, but I was feeling a bit vengeful as well. He had dated my sister after all and there was most definitely some unfinished business between us. I slipped into some sexy red lingerie, packed an overnight bag and walked out the door, I had an old friend to meet.