My Dating Life Number 1: My First Boyf The Boy On Pills The Tie-Me-Up Guy 

When Was Your First Time…? (Part One)

There’s nothing like a good bit of reminiscing about past lovers when you’re experiencing a dry spell in the sex/love department. That’s what I did today, at work, talking about firsts. Those moments in life that change it forever. You know the ones I mean: the first kiss, first fuck, first sexually awakening moment, first heartbreak, yadda, yadda.

I thought it might make for a good blog post. Plus, I’m in the mood to talk about it and reminisce some more, so I apologise in advance if this gets a little boring.



Unless you’re counting Tom Cruise, who I had a major crush on when I was high school, my first crush was a guy I later managed to fuck when school was over and out. He was Number 16, also known as The Boy on Pills. He got the name for obvious reasons: the night we finally slept together, he was off his face on pills. He was out of my league when we were at school, him with his dashing smile and charismatic ways. He was a bit of a jerk to me, to be honest, and the super hot guy that I had a burning crush on wasn’t even that great in bed. I learned that lesson years later. Our one-night-stand was soon forgotten about afterwards. I had no intentions of ever repeating it.

Still, I wanted him, I got him.



My first kiss was every bit as awkward as first kisses are meant to be, and I gave mine away to a kid that I couldn’t actually stand. He bullied me all the way through high school, to the point where he actually made my life hell. We had a weird flirtation that I certainly didn’t understand. Like, we hated each other, but there was also something else going on. At that age, neither of us understood what it was. These days, it would be the kind of sexual tension you have with a work colleague that you don’t like that much, but you end up fucking regardless.

The kiss was all slobber and tongue because neither of us knew what we were doing. Even more embarrassingly, we were in the middle of a circle of people who were egging us on, in the locker room of the Design & Technology block.

“Kiss him, kiss him, tongues, tongues, tongues,” was the chant of the twenty-or-so kids that were all around us. What else was I supposed to do but kiss him?

And that’s the sorry tale of my first proper kiss.




I remember having a party at my house during the day (?), at half term and when my parents were at work, begging my younger sister not to say anything as four boys and one other girl ran rampant around the house. There was a boy that I’d been kinda seeing for a while. We’d made out a few times and hands had gone in my bra, but that was it, nothing more than that. No actual sexual touching … until that day-party.

There wasn’t alcohol or drugs; we were too young for that. Instead, we got high on copious amounts of sugar and turned the music up loud. My ‘date’ and I went up to my room to make out on the bed, and it wasn’t long before he slipped his hands under the waistband of my jeans and right down inside me. It was the first time I’d been penetrated by something other than a small tampon, and the activity made me bleed all over his fingers. The way he reacted absolutely MORTIFIED me.

He told everyone. Everyone. Literally everyone he could tell. He told people that it was evident I was a VIRGIN as he’d just broken my hymen and made me bleed. He told people in a way that both mocked me and boasted about me, making me feel disgusting, gross, like a monster. He told the boys that went to his school, and the boys and girls that went to mine. It seemed to me like EVERYONE knew … and they were all mocking me.

My parents didn’t find out about it, thankfully, but they did find out about the party. Someone had spat in our fish pond and the offensive lump was still floating in the water when my dad went out to enjoy his coffee in the back garden that night. My sister and I were promptly questioned, and of course she bloody cracked and told them the truth.

What a fucking prick that guy was, though. I always thought his best mate was fitter.



My first fuck was a complete disaster. It was with Number 1 – My First Boyf, and it was an actual disaster of disastrous proportions. Once again there was blood, but this time it wasn’t mine.

You can read all about that monstrosity of a tale here: BLAST FROM THE PAST: MEET NUMBER 1. MY FIRST TIME.

I can tell you this much: it wasn’t quite the ground-breaking experience that I thought it was going to be. It was disappointing. There were no fireworks, no real spark, and although we might have been like it like rabbits during our year-long relationship, it wasn’t that good. He briefly ruined blowjobs for me, but thankfully, I got over that.

[You can read this if you don’t believe me: I MISS MY TWENTIES]



Yeah, this sorry tale deserved a blog post all of its own too. My first anal experience was horrendous. Awful. Painful. Dry. It ruined anal for me. Anal is still not something I’m completely comfortable with. I don’t just blame this experience; I blame a few of my shitty anal experiences. This one definitely didn’t get things off to a good start, though …

You can read all about that (it’s a PAINFUL tale) right here: #METOO



I class my first sexual awakening as the first moment I realised that I wasn’t into entirely vanilla sex. I enjoyed sex with Number 1. But when Number 2 came along, I really got to play. It was with him and his playfulness that I figured out that I liked a little bit of pain along with my pleasure. He would bite and scratch and tug at me in ways that would make me wince with pain but writhe with pleasure at the same time. I didn’t understand it back then. Whenever I talked about my sex life with my friends, I always played it down a bit, worried that they’d see me as a freak. It would take a little while before I learned how to be comfortable with my own sexuality, but Number 2 definitely helped to open those doors for me.

There is one particular occasion that sticks out to me, to this day, and we’re talking almost 15 years later. It was early evening, middle of summer, still daylight outside. Number 1 would never take my underwear off when we fucked, instead just shoving them to one side as he slid into me alongside them, so I was super nervous about taking my pants off in front of Number 2. He did everything to put my mind at ease and make me feel more comfortable, but I was still squirming at the thought of being completely naked in front of him, in broad daylight. He see *everything*. It would be the first time that anyone would see me completely naked, in broad daylight, which is quite weird when you consider I’d been sexually active for a year at that point.

He suggested one final thing to help with the nerves:

“Why don’t you put a blindfold on. Just lay back, think of how good it feels, and pretend it’s not daylight outside.”

That’s just what I did, and he tied my wrists to the bed above my head so that I couldn’t push his head away as he tried to move down between my legs. It was that moment – that EXACT moment – that bondage became a real thing on my sexual radar. To this day, being blindfolded and tied up as someone goes down on me is still one of my favourite things to do.

… to be continued.

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