The Hilarious Story of How I Lost My Virginity!

I’ve told this story a few times, but as this is a new blog it warrants telling again.

I was 18 when I lost my virginity, which at the time I felt was quite late compared to the rest of Liverpool. I’d spent my teenage years laboriously learning the mechanics and the theory behind sex (which as an adult I don’t regret – neither do my partners 😉 ) and outright lying to my friends about how, like, I had totally done the sex.

We all want our first time to be special and memorable. Mine was certainly memorable, and ‘special’ in a sense that I’m willing to bet that it is a unique story.

It was Halloween (always a good start to a story), and my friends and I were heading to The Krazyhouse for their famous annual Halloween party. There was talk of going in fancy dress, but as usual I was the only one who actually followed through on it. I ended up going out dressed as Hannibal Lector – an outfit that consisted of a mask, a blue boiler suit and nothing but a g-string underneath (there is a photo somewhere, but I can’t seem to find it).

Anyway, we all ended up in The Krazyhouse and I somehow managed to lose my friends. That wasn’t a major issue – the majority of nights out I have, even today, are on my own. I’m usually a reliable date! Somehow I ended up dancing with these two girls, Chrissy and Vicky, both dressed as sexy witches. Chrissy in particular took a liking to me. There was lots of making out on the dancefloor, and then we headed upstairs to the seating area by the pool tables. She then proceeded to straddle me on top of my boiler suit, and grind against my cock through our clothing. Nothing sums up awkward teenage lust than ‘clothes-on’ grinding. It’s a matter of pride that I managed to make her orgasm just from that (that boiler suit was very thin).

Back onto the dancefloor, where she proceeded to give me a sneaky handjob right in the middle of the K1! It was, up until that point, the sexiest thing that had ever happened to me (it’s still pretty sexy to me to be honest). I started thinking to myself that maybe this would be the night where all my teenage fantasies of actually having sex with a woman would finally be fulfilled. Believe me, the film ‘American Pie’ exactly captured what it was like to be a teenage male at the turn of the century, which is why it remains the definitive teen movie of my generation.

Chrissy and her friend Vicky invited me back to their flat, but not before we randomly stopped at the flat of a local Liverpool musician (I still remember his name, but for the sake of privacy I won’t repeat it), where we all watched ‘The Ring’ on his bed and Chrissy gave me another sneaky handjob under the covers!

We eventually make it back to their flat in a taxi, and let me tell you, this flat was the most disgusting flat I’d ever seen. Remember that episode of Friends when Ross starts dating the beautiful woman played by Rebecca Romijn (“The One With The Dirty Girl”), but has to break it off because her flat was too filthy. This flat was EXACTLY like that. But as a teenager, I was willing to overlook such things due to the possibility of sex. Vicky disappears somewhere whilst Chrissy and I sat on the sofa. She put on a CD and proceeded to give me a blow-job.

Now blow-jobs are blow-jobs – I can take them or leave them and one is generally as good as another. The reason this one – and the whole evening, really – sticks in my head so clearly is not because of the act itself, but the tracks that were on this CD. There were only three, and Chrissy had set the player to repeat these three tracks over and over again. These were the first two tracks:

Let Me Entertain You by Robbie Williams – nothing particularly weird about that, although it’s not the most interesting song in the world.

Closer by Nine Inch Nails – that one’s pretty cool. For non-NIN fans, that’s the one that goes “I want to fuck you like an animal”, and is usually what I tell people I lost my virginity to.

The third track – and I swear this is true – the third track was Brodie (played by Jason Lee)’s opening monologue from the film ‘Mallrats’. For those of you who have never seen Mallrats (you’re, like, totally uncool!), someone has helpfully uploaded the monologue to Youtube here.

With the CD still playing, we went next door to the bedroom – mattress surrounded by dirty clothes – and I went down on her. This was my first time being this close to a vagina, so I wasn’t quite sure what I was doing. But what I lacked in experience I made up in enthusiasm! Pubes were still a thing back then, which made navigating the region slightly more difficult for a novice, but I like to think I did ok.

Then we had sex. It was ok. My overriding memory of the act itself was how natural it felt. It didn’t feel strange to me at all, but more like “this is what I have a penis for!” Her friend Vicky kept interrupting occasionally – had been older and smoother, I might have invited her to join us. But because I was a teenager and still self-conscious about my penis, it was a question of hiding under the covers.

I can’t remember if I came or not. I do remember leaving the flat and realising I had no clue where I was, wearing nothing but a boiler suit and a g-string (the mask got lost somewhere). I had to ring my dad from a payphone as I didn’t have a mobile phone back then, and describe where I was (somewhere in West Derby).

Looking back, it was incredibly stupid to have unprotected sex in a flat like that. Obviously I’ve been tested since and am totally clean. But I don’t regret the experience too much. How many people can say they lost their virginity to a sexy witch whilst dressed as Hannibal Lector, with a guy telling a story of how his cousin got a cat stuck up his ass once?

Someday I will get to tell Kevin Smith this story. I think he’d get a kick out of it!

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