“I Lost My Virginity To A Prostitute”

I Lost My Virginity To A Prostitute - True sex stories free online.

In Sex With Friends I talk to acquaintances old, new and virtual about the most interesting aspects of their sex lives. Here, I’m talking to… well, in a break with tradition I’m talking to myself. My younger self, actually. I’m going to call him “Me”, and he lost his virginity to a prostitute in Amsterdam.


Shadow: So… this is a little bit weird. You know I’d forgotten we used to dye our hair? Anyway. Blah. Let’s get down to it. How old were you when you lost your virginity, and what was going on in your life at the time?

Me: Okay. Context. I was an awkward teenager. I’m sure you remember. It took me a long time to figure out how to relate to girls. I was so crazily shy around them even at school, and things just got worse as I got older. I never had a girlfriend or anything like that. I just didn’t know how other people did it. I’d talk to girls, sure, but I never knew how to progress things from there, and it made me super shy and anxious.

When I was seventeen I went travelling around Europe. It was the first trip I had taken entirely on my own and I was having an amazing time – I guess I’m kind of a loner, present company excepted. I did meet people at hostels and on trains though, and in the course of talking to some guys I met in Germany I learned about the window brothels in Amsterdam.

I was amazed. I knew prostitutes existed, but I had absolutely no idea how you’d go about finding one. The fact that it was illegal back home had scared me out of ever trying. But, I was told, in Amsterdam not only was it legal, it was easy. The women hung around in windows and all you had to do was stroll up and knock. The idea that I could just go and do this and have the whole virginity situation taken care of in the space of half an hour was intoxicating.

Shadow: So you went to Amsterdam, right? What was it like?

Me: I did. I was super nervous beforehand… but it wasn’t bad nerves. I knew that if I screwed up somehow it didn’t matter – I could just do it over again. I took a shower and made sure I was clean. I got out some Euros to pay her with, and I looked up online exactly how to behave. Then I went to the Red Light District and walked around until I saw a woman who was both stunningly attractive, and looked happy to be there.

We talked a little in the door, and then she let me in. We went down a corridor to a room which was lit by a blacklight. There was a bed with a dragon on the covers. I remember it very clearly. She told me to take my clothes off and I was like “Right now?” and she said, “Well, if you want to fuck…” and we both laughed.

She had me lie down on the bed, and got a condom on me and started giving me a blowjob at the same time. She was so proficient at it, and I was kind of excited, and I probably could have finished right then and there. But after a while I told her I’d had enough and we switched places. She smeared some lube on me and guided me inside her.

I don’t know how long I lasted. Probably not long. I had never so much as touched a vagina before, and she was – in case I didn’t mention – supermodel-level attractive. She was blonde and smiley and wearing this UV bra, which she took off while she was blowing me. Even now she had probably the most perfect body out of any woman I’ve ever seen. She could read me really well, too. As I was about to come she reached down and wrapped her hand around my cock and squeezed and it was like she was squeezing an orgasm out of me.

Shadow: Do you think she could tell it was your first time?

Me: I don’t think so. I told her I was older than I was. And I tried to act like it was no big deal, the whole thing. I guess sometimes I didn’t really know what to do, so she probably thought it was my first time visiting a prostitute, but not that it was my first time ever.

Shadow: Okay. Look, I’m not really supposed to tell you stuff from the future, but… yeah… she could definitely tell that it was your first time. You’re not as suave as you think you are.

Me: Oh. Right. Um. How do you know?

Shadow: Just… trust me. And don’t ask too many questions. We don’t want to start a paradox. Was it like you expected, or different?

Me: I really didn’t know what to expect. In my head everything was a blank slate in terms of what it would feel like. When she started giving me a blowjob I remember thinking, “Ah, so this is what it’s like”. Same for sex. I was just really interested the whole time. Like, I’d spent a lot of time thinking about how it might go, but in the moment I was too excited to discover how it really was that I completely forgot all my expectations.

Shadow: Interesting. I forgot we used to say “blowjob”. God, that sounds like such a high school thing to say now.

Me: What do you say?

Shadow: I don’t know. “Going down on,” is a bit less gross, I guess. Plus it works for both genders.

Me: I guess. Hey, speaking of terminology, I was reading this article about the phrase “losing your virginity” and how it’s kind of got negative connotations. It was saying we should use “sexual debut” instead.

Shadow: Yeeeeeeeeah. Sure. Kind of sounds like it’s happening under a spotlight, but whatever. You do you. Language is a virus, etc, etc. How did you find the Red Light District when you were there?

Me: Just… exciting, I guess. Everything was so open. So unashamed of itself. Sex had always seemed like kind of an abstract thing to me before, and this was the first time I’d seen it in anything close to real life.

Shadow: You didn’t find it… kind of lurid? Money-oriented? Little bit greasy?

Me: No. Not at all – not really. I was just excited about it, I guess. Why? Have we gone back since then?

Shadow: No comment. Oh, one thing I’ve been meaning to ask – do you remember her name?

Me: I made a point of asking her name. It seemed important – you know… to know the name of the person. And so I asked, and she told me something like Crystal or Champagne or something that definitely wasn’t her real name. And as soon as I’d left and was walking along the canal out of the Red Light District I just completely forgot. It slipped out of my head.

Shadow: Not even a vague memory? You’re about seven years closer to that night than I am.

Me: Maybe it was Crystal. Hey, can I ask you something? If you’re all done with your questions?

Shadow: Sure. Not saying I’ll answer though. I don’t want to Back To The Future myself out of existence.

Me: How do people react when you tell them?

Shadow: Okay. I guess that can’t do any harm. Most people are just interested. I’ve had a few people grill me about it in a kind of hostile way – but that’s usually because they know nothing about prostitution outside of their home country. Other than that they just have a bunch of questions. More people than not have said they’re jealous that it went so well. Oh, and some people have asked if my first experience of sex being with a sex worker lead me to be into all the kinky shit I’m into. Like, did she corrupt me or something?

Me: Really? That’s hilarious. We were kinky waaaay before we ever got a chance to try any of it out.  One more thing – what happened afterwards? Did we ever sleep with a prostitute again?

Shadow: Nope. It was a one-time thing. And – don’t tell anyone I told you – but it did wonders for us. Once we were no longer a virgin we just felt so much more relaxed about the whole thing. We started being more normal around women and after a while we had a girlfriend. It was basically an entirely positive experience, but not one I’ve ever needed to repeat.

Anywho, let’s round this off. Knowing us, if we spend too long together we’ll probably start fucking. How do you feel about it? Do you ever wish it had happened differently?

Me: Not at all. I had a great time with little to no awkwardness. Maybe nine out of ten sexual debut stories I’ve heard have either sounded pretty horrendous or like the person involved got their feelings hurt… or hurt someone else’s. I’m glad to have avoided all that.

One thing that didn’t occur to me at the time though was that it could have gone quite differently. I’ve read some stories about sex workers pressuring clients to pay more and hurrying them along. Mine didn’t. She took her time with me, and she was – I realised after – really kind and considerate; especially given that she was at the start of a long night shift. I’m grateful to her for that, I guess, even if I don’t remember her name.


Isn’t young me cute? He’s never online these days, but if you feel like it you can be my friend instead .

Got something to say about this? Hit me up. But be nice if you actually want a reply.

More stuff like this? Well, only because you asked for it.

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