I lost my virginity to a hooker

Name is pending
8 min readFeb 24, 2022

and I was 14 years old. Two decades later I’m confronted with the memory again and decided to talk about it.

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Well, the title gave it away, didn’t it? Although I always considered that story more funny than serious (it kinda made me unique, didn’t it) after such a long time it seems like I just realised something.

Not that I didn’t know that it sucked. It really did. To this day I couldn’t figure out how someone as bad at their profession as she was could charge 250 bucks an hour.

But let’s go back a little. I was 14 years old. I was on a business trip with my dad. The first time really that me and my dad were alone on the road as I remember just now. At least the first time for a long time.
We didn’t have the best of relationships, we really didn’t. But on that trip we had fun together, quite a lot actually. It seemed like as we were alone a lot of things were different. It seemed like nothing that happened that had made our relationship that miserable seemed to matter for that short period of time. It was one of those rare occasion where we would see eye to eye!

I helped him out with his work and in the evening he would kinda introduce me to some nightlife. On one evening after we ate at a restaurant we were at a party, we stood around at one of those roundly built bars, where the bartenders stood inside, surrounded by an encircling, light coloured wooden plate. That’s where my dad paid for the first drink we’ve had together. I think it was beer, not just one but a few — but not too many. And even though he didn’t want me to drink a full Jim Beam Cola he at least let me nip once or twice.

On the next evening things went differently. My dad’s best friend joined us (and with him a few guys as well, but I don’t remember them at all or how many they were, maybe it was one or two? But they don’t matter anyway). After going around for awhile we ended up in a place that would soon turn out to be a brothel. And soon enough we stood in front of a row of woman where I was faced with having to make a decision
“Which one do you want to have accompanying you, son?” There wasn’t any chance of sex on the table at that point. Even if I’m in a brothel right now, right? This was just “company”. But I couldn’t decide. I was 14, not really fat but not really slim as well. And I was shy as fuck around girls, not to mention woman… not to mention women that were barely dressed at all with nothing more than what could go as a medium sized bikini. I’m talking about coverage here.

There was a woman that immediately got my eye, but I also didn’t want to offend the others. And as I mentioned before that I was really shy so I couldn’t bring myself even to make up my mind. So I went for the toilet instead because I really had to pee.

When I came back my choice was made for me. My dad, his best friend and these other guys made their choices and I got who was left. She was pretty, not so much my type as the other one but she really was pretty as well.

First we sat all together, her flirting and touchiness where like something out of a dream. Literally. Imagine being 14 years old sitting in a brothel, drinking a bit (as age appropriately as it would be to drink at that age with my dad I didn’t get shitfaced. I didn’t really need him for that anyway. Yeah my childhood was rough), a pretty woman’s hands encroaching you, seemingly getting very familiar with you in a very short amount of time.
We switched places and went to a different table a little more private where we could talk a little more open. When she asked me about my age I said I was 17, almost 18 years old. A lie that was the most easy thing for me this evening, because people usually assumed as much. She turned out to be 28. It was actually quite shocking to me that it was so easy for me to lie in this situation, even though I opened up quite a bit and got more comfortable in my skin.

Let me state here for a second that I did enjoy this night out. One might righteously question my dad’s decision to bring me along into such an environment but let me make one thing clear: as awkward as I was, to get that kind of attention from a woman is basically the dream of everyone that age.

Well it’s clear what happened next. After I got presented that my dad and his best friend would gift me my first time we made it up to her room. Yes, they both chipped in together and paid for it. But don’t worry, I won’t go much into detail but let me tell you this: It. Wasn’t. Good!

There was no kissing involved, which I think was the worst thing. Kissing was the only palette of experience I’ve had so far on the road towards sexual activity. And without it, honestly, it made that act almost feel sterile, clinical. There was a little foreplay but damn was it absolutely different than what my puberal, 14 year old mind had ever imagined.
To share at least little detail I remember clearly that for days after she took my virginity my stomach would hurt because instead of riding me she literally just jumped up and down. And instead of like every “normal” 14 year old quick-shooter I didn’t finish.
And there was the time-pressure as well. We were on a clock. 30 minutes was granted, that was the time-limit. A time-limit like that? When you are supposed to have the most beautiful, memorable moment in your life?

All of those factors in chronological order by impact summarised into the experience of emotional insignificance of this experience. Even worse, the amounting of this became a negative experience.

Well, I write that story now because I just recently somehow stumbled over the description of what that experience is supposed to be. The almost utopian fantasy that everyone has about it. And I realised that I don’t share any of those. It was special, yeah it was. But it kinda just happened, there was no working up towards it. No preparation went into it, the person was no one special to me. There’s no song that I remember even surrounding that moment before it became because there was no music in that room. It was what it was: a blank canvas which should have been full with colour!

It was a service in exchange for money. At one point I realised, even though I might have been a cute boy that at least wasn’t ugly as hell, so I could have gotten there by myself somehow… but I realised my first time was a business transaction that happened because of money, not because of me. And weirdly enough I must say that even 14 year old me was to some degree aware of it.

Well. Years later I spent another road trip with my father, a very cathartic one. He did tell me sometime before, reminiscing about that first trip of ours, that he always dreamt of his father paying for his first time and that this was his basis for doing it. He literally just wanted me to have what he didn’t had in his childhood and at least on that weekend besides how the experience was for me we had a relationship that he never had with his father and a relationship that we surely didn’t had as often as we should have had.
It took me over ten years to finally confess to him how it was for me, because I couldn’t get myself to do what seemed to me would break his heart. It was one of the rare moments he had some life in his eyes, thinking and talking about me, about us, about that weekend, talking about the fun we had and remembering that he could provide me with something that he never had. It were those rare moments were all of our troubles were forgotten, were we just were father and son and I couldn’t take that away from him.

During that last real trip we’ve had I finally told him, not in a confronting manner, I just told him how I didn’t finish and that I didn’t really enjoy that experience in that room. And we talked about it. It was the nature of that trip that made me being honest with him about this even possible because we talked about all the shit that went wrong in my childhood between us. We talked about his failures as a father, my failures as a son (and yeah, I did fail as well) and that provided the grounds for me to come clean about this to him.

Why am I writing this? I think in one way its more therapeutic for me than anything else. It’s honest. I kinda fell back into the memory of that moment with a clarity that it stirred something up again, made me realise some aspects about it that weren’t obvious to me so far. And I sometimes do still think of the rare, good moments that my dad and me shared, that were just us. In his own way he was still a child, always, as far as I remember back until the last time we met. I can’t help it, and even though many people would disagree, his intentions were pure and innocently naive, but in some bizarre way I’m almost proud that I was worth so much to him that he would gift me with something like that, something that would have meant so much to him as twisted as it might seem.

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Anyways, thanks for making it this far, have a beautiful day, where ever you are.

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Name is pending

Away from politics more into stuff I feel like writing about with the hope to find myself in some topics. Join me on my travel to writers glory 😅