My Dating Life The Fireman The Tie-Me-Up Guy 

When Was Your First Time … ? (Part Four: Heartbreak)

Yep, still carrying on with those firsts again. Carrying on from the kissing and sex stuff in Part One, and the first loves in Part Two, and my first great love in Part Three, I’m now moving on to heartbreak.

Oh, the heartbreak!



I’ll never forget the first my heart broke over a boy, but it wasn’t actually a boy’s actions that caused the heartbreak … it was my own. It was nothing particularly big or spectacular, but I remember it plain as day, as though it were yesterday, and I don’t think I’m ever going to forget it.

I was dating Number 5 – The Fireman. We dated for about two years in the end, but it was a rocky road, and I almost royally fucked it up on more than one occasion. I was a young’un at the time, only about 16 or 17, and this guy was besotted with me. I was dating Number 2 before him [The Tie-Me-Up Guy], and Number 5 had told me on many occasions that I was the woman of his dreams. When my relationship with Number 2 was well and truly over, it just made sense for me to fall into the arms of Number 5.

We’d been together a while when I made a whopper of a mistake. Enough time for us to have fallen head-over-heels in love with each other, anyway. We were inseparable. If I wasn’t at his place, he was at mine. We spent every spare moment we had together, and we even lost jobs because we spent entire days in bed together. Sometimes, we’d call in sick. At other times, we wouldn’t bother, carried away by whatever new and exciting sexual act we’d discovered.

But then one night, Number 2 called me up out of the blue. He wanted to go for a drink and have a chat with me. To talk about the disaster that was the ending of our relationship and maybe come out of it as friends on the other side. Looking back now, I can see that it was a plain ol’ ex-gf booty call. At the time, though, this beautiful ex-boyfriend that had once spectacularly broken my heart wanted to spend some time with me. Being young and dumb, I fell for it.

I went for the drink. Many drinks. We ended up having to sleep in his car in the parking lot because he was too drunk to drive home. And we did the inevitable before we passed out: we fucked. I’d probably have managed to keep it all a secret had I not written down what happened in my journal. But I did write it down. And, just as predicted, my actual boyfriend – Number 5 – found it and read it.

We broke up in spectacular fashion, with him literally throwing my belongings out of his house and onto the street. And I’ll never forget the look on his face. Blind rage. Anger. Total betrayal. There wasn’t hurt in his eyes yet, but that would come later on. First, he had to let his rage out.

A few weeks after that, we had a little incident involving him turning up at my house in the middle of the night, blind drunk, wanted to talk, fight, and fuck … and not in that order. I saw anger and betrayal in his drunken, blood-shot eyes that night, but I also saw sadness. Great sadness. In turn, I felt sadness. I couldn’t get those sad eyes out of my mind for weeks and weeks and weeks. I’d have done virtually anything he asked to undo my actions. And to this day, I’ve never forgotten that sad, betrayed look on his face. The way his eyes looked so forlorn and miserable … I still feel so awful for doing that to him.

And that was the first time I felt true heartbreak. It wasn’t even my own.

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