3 guys, 3 stories, 1 week.....Part two...

A couple of days ago, I promised to tell you a slightly longer story about a young man losing his virginity to a prostitute. If there were such a thing as a master class in how to lose your virginity to a sex worker, I have a sneaky suspicion that it might sound something like this:

Cody. Born in 1987. Lost virginity a couple of weeks ago.

‘Alright, here goes-

I'm twenty-one years old, from the USA and I recently lost my virginity to a Canadian prostitute. I'm sending you this because I hope it helps other people who were in situations like mine, and because writing it will help me collect my thoughts.

I originally got the idea from a close friend of mine. He saw my frustration as I went through all kinds of changes in life - not the least of which was choosing a different religious life than the one my family had. I grew up in 'a certain church' that is very strict and extremely sexually repressive. While it teaches some great things, sex outside of marriage is called ‘the sin next to murder’ and anything even remotely sexual is 'evil'.

I was also coming out of an 'awkward teenager' phase - I had been too religious to even swear. I was horribly overweight. My confidence was low, my social skills damaged by the religiosity, as well as by the many times my family had moved and by the isolation and 'sheltered' childhood I had had.

By the time I was a freshman in university, I was only ambivalent about having a sex life. I wasn't even sure that I wanted to lose my virginity until about the end of freshman year. Once I was sure that I wanted to lose it, it became a race against time. I was the only person in the whole world who had never had sex. I was missing out. This made me anxious, which of course made it impossible to lose it. I was trying to run before I could even walk, I was so far behind - I was worried about losing the v-card before I had ever even kissed a girl (first time: age twenty).

I tried to console myself by remembering that a lot of it wasn't 'my fault', but that didn't help much. Sometimes I was so down on myself - here were the greatest years of my life, slipping away before my eyes. I would die having wasted so much irreplaceable time. I was frantic. I sometimes even felt so frustrated and bitter that I questioned whether life was even worth continuing without something as basic as sex.

But I was also losing weight quickly, finally getting my act together socially, and making all sorts of small changes all the time. I was making progress, but it still couldn't come fast enough. I had a handful of 'close calls' but at the last minute someone would interfere and ruin it for me; also I was so afraid of screwing up such a rare opportunity that I of course screwed it up. Trying to lose my virginity was getting in the way of trying to lose my virginity.

‘Dude, just get a hooker’ a friend of mine called Tyler suggested.

‘What the hell are you talking about!? Some disease-ridden whore who I'd have to pay money for? What kind of loser do you take me for?’

Tyler was about to completely change my perception on prostitution.

‘Now hey - everyone has to pay for it. Think about it. You can spend hundreds of dollars on gifts and dinners on a girl, with no guarantee that you're gonna get laid, or you can spend a set amount of money with a guarantee. And hookers have to stay clean, otherwise they'd be out of a job.’

‘But it's... I dunno, there's no honor in that.’

‘You think it's 'honorable' to hook up with a drunk girl at a party? She's more likely to have an STD than a professional is, and if you mess up, what if she goes and tells all her friends how awkward it was? What if you knock her up? Paying for sex isn't degrading - if anything it's degrading to the person being paid. It's liberating to get rid of all the bullshit and stupid games people play and just have sex. It's just 'animal sex', not lovemaking, but at least with a hooker it's honest and straightforward unlike a lot of the 'dating' we see around here.’

The more I thought about it, the more I realized he was right. Losing it to a hooker wasn't ideal - I would have liked to have found a girlfriend - but I also realized I couldn't do it at the time. Prostitution was, when I was completely honest with myself, better than the usual drunken hookup that I observed at my university. So it was either pay for alcohol and hope to get laid, or pay a sex worker and be done with it.

I found out that some of history's greatest womanizers and powerful men - Kennedy, Gabrielle D'Annunzio, Napoleon Bonaparte (and in the original novels, even James Bond) - as well as several others had lost their virginity to prostitutes. I also found out that in some societies it has been (and in a few still is) customary for young men to lose it this way.

One thing led to another and before I knew it, I had bought a plane ticket and two nights in a nice hotel in Canada.

I had set up an appointment before leaving with an independent escort, but as I waited for her to arrive (nervously), she was late. After an hour had passed, I went and checked my email - she had had a family emergency and was unable to come that day, and wouldn't be working again until after I left. Damn.

I was nervous, terrified even. I went and took a long walk. I even thought about calling it off. But no, I would never be able to look Tyler in the face again if I backed out now. I had told my friends (the few who knew I was still a virgin) that I was going to lose it, I had told myself that it would be before the year's end (and I lost it with less than a month to go - but it's a New Year's resolution I'm glad I kept!), and I had put too much time and money into it.

I thought about what to do. After a few hours, I went to the phone book and looked up the name of an agency I had heard of before leaving. I called them up and explained my 'first-timer status' in the ambiguous terms Canadian law requires. ‘That's fine Sweety, I've got a few girls I think would be perfect’. After some discussion, a time was set and I took a shower. My virginity was about to be done away with forever. I was nervous, but the understanding tone of the woman on the phone made me feel better. ‘That's why a lot of these girls do what they do’ she said.

I got a call a while later telling me to go down to the lobby. She was blonde, wearing a black dress and carrying a bag. I went down and found her. She looked like a businesswoman almost, very classy. A little older than me, as I had requested. She was not trashy or wearing too much makeup, not drawing attention to herself, just a normal, pretty girl who happened to make a living by having sex.

We went up to my room and we started by having a drink together (her suggestion). ‘You'd be surprised at some of the people I see - I view myself almost like a therapist’ she explained. She and I talked and she put me at ease; she listened to me and catered to me perfectly.

I was in just my pajama pants at this point, stomach-down on my bed, and she straddled me and got some lotion on my back. After a few minutes, she got up and stood in front of me and said ‘Every woman is a little insecure about her appearance, even me. I still feel a little weird sometimes with men watching me strip’. And so she did.

All the reader needs to know is that she managed to make it (relatively) smooth and natural. She may not even have been enjoying herself, but if not, she did a damn good job pretending. She was all about making the client happy.

I got a sampler of all kinds of different things. She told me what to do, guided the whole thing. I was able to joke around with this girl and she made it feel like the natural, enjoyable thing it should be. I went into it extremely nervous but felt much better after a few minutes with her - and by the end I felt great.

When she left I had a big smile on my face, but I was surprised by how unglamorous and non-dramatic it was. Sex became something good, but not a life-and-death issue as it had been before. It became just another part of life, thrilling but not the most thrilling thing in the world. The mystery behind it was gone - sliding my fingers into a woman, feeling her different fleshy areas, having her ride me, touching and seeing every part of her body didn't feel so strange or mysterious. Still highly enjoyable, but I noticed that it was purely physical - as it should have been and as I had expected. The feelings I had had in the past, spending time with girls I felt affection for as people or a strong desire for, had been more intense in some ways, more intoxicating.

I realized how, even though people glorify and idolize sex, it is an overrated good thing. Most good things are overrated I guess - sex is no exception. The people who brag about it or take the bragging tone when they talk about it are usually compensating for something (not that I am entirely innocent in this department; I've had my immature moments).

I actually had some bad experiences - two independent escorts that I had lined up didn't work out (the one had had a family emergency, the other just didn't pick up her phone when I called to confirm), and the second one I hired wasn't very good. She wore too much makeup, and you could tell her heart wasn't in it. She was very 'pay me, fuck me and I'm on my way' without any regard to doing it right. There is an art to sex; a girl who leaves her chewing gum in the condom wrapper on your desk is not a very good artist.

But even this taught me something - after getting over the awkwardness, I was glad I didn't have to see her ever again, I could distinguish a little better between good and bad sex, and I knew that it was okay to be a little more choosy about who I sleep with in the future. If that girl had been someone I knew personally, it would have been far worse. I was glad I had gotten my first 'bad sex' out of the way with a woman I didn't need to worry about. It's perfectly okay to turn down or pass up a hot girl who's a pain in the ass as far as personality goes - looks aren't everything. This second one had some better physical features but a horrible personality; it turned out that feeling and technique is a more important part of sex than I thought.

I still get annoyed when I see an immature and maybe slightly effeminate guy, fresh out of high school, with a stunning girl. But the bitterness is mostly gone; in the back of my mind I know she may well be no better than jacking off. She may be worse. She may be great, but who knows and who cares? Sex is not such a big deal after all - but of course you can't know that until after you've had it.

Before I did this, people told me sex wasn't a big deal. But until I experienced it for myself, it was annoying - sometimes infuriating - to have people try to preach to me.

‘Dude, sex is no big deal, just relax. It'll come one day.’ It was irritating to have people talk and not listen, to ignore my needs, to pretend to understand when they had no idea what I was going through.

They tried to persuade me with reason and arguments, but - as a few exceptional friends like Tyler knew and understood - only when I experienced it for myself could I know this.

It's important to have a couple of friends you can trust with this; it's important to honestly not feel ashamed about it; and be ready for some awkward moments - but remember, they're only really awkward if you can't laugh about them. Have a good sense of humor about it, and enjoy the feeling of having your first 'sex stories' for those times when the guys get together.

I'm glad I lost it on my own terms at a time and place of my choosing instead of leaving it to chance. No awkward conversations or 'I have to see this person every day in class', no major risk of being backstabbed, no risk of being cheated on, minimal emotional vulnerability. In retrospect, I'm confident it was the right decision.’

Comments

[AzureWolf]

Beautiful story (never thought I would say that in context with prostitution, haha). Although I disagree with his conclusions, I think it is quite a memorable and amazing "adventure." Bravo

[Kate Monro]

Wasn't it a cracker...

I do like his conclusions, paticularly the realisation that sex is so much more than a straightforward physical transaction. Of course it can just be that and be very pleasurable at the same time but the emotional side is surely the most intoxicating part of all no?

[Organs]

This is probably one of the best virginity-loss stories I've read. The author doesn't pretend that it's a magical experience, and the author understood that all the patronage and condescension from people trying to make you feel better is complete bunk. And the context and everything made it all the better. Kudos.