How not to lose your virginity


Sex is a skill. For starters, you have to master the art of stimulating the clitoris while fucking – the sexual equivalent of rubbing your tummy while patting your head. Some end up being better at it than others, in the same way that some people are better at remembering names than others. But ultimately it’s a skill: it must be learnt. The first time is never the best time.

It’s through repetition, experimentation and discovery that you get the good stuff- the really sweaty, late-night, out-of-your-mind stuff. You don’t get that the first time. Everyone knows this apart from virgins. Virgins never consider the first time as a trivial first step. They consider it a seismic, lyrical moment, fat with meaning.

We should commiserate the young on their perpetual foolishness, but we should also accept their limitations. There’s no point telling teenagers that the first time is an overblown phenomenon. Instead, we must guide them as best we can. It’s with that sentiment in mind that I offer this, a handful of rules to be given to virgins as they contemplate their first experience.

Rule one: These rules are irrelevant.

The very idea of trying to master the perfect first time will be laughable to most boys, for whom the ideal moment is whenever a girl first allows you to do something. Let’s not fuck about: you probably wouldn’t mind if it was on the High Street in front of your extended family with you wearing a bridal dress.

Girls: You will lose your virginity to a twat. The nice, decent boys in your school will seem childish and desperate to you. They won’t yet have learnt how or why to act aloof and dismissive towards women. They will learn. You will teach them. You will do this by ignoring their genuine advances, going off with someone who couldn’t care less abut you and subsequently breaking their heart. Later, you will justifiably complain that all men are bastards but remain blissfully ignorant of how ironic your anguish is. There’s no point pretending that my rules will have any effect on the series of mistakes you are about to make.

Rule two: Forget about love

It’s the most common mistake in virgin land: waiting for love. This might seem cold or heartless to you, so let me explain in a personal manner which might, if not convince you of my sincerity, at least allow you to sympathise with me. I will now tell you the story of my first kiss.

I was 13 years old and I was at a party. A friend of mine had upset his girlfriend and her response – perfectly reasonable for someone her age – was to walk around the party and kiss every guy there. She emerged from the darkness at one point and asked simply: “Have I snogged you yet?”

“No,” I replied. And then she did. I remembered thinking: ‘This is wetter than I had imagined.’ I was also unsure what to do with my tongue, so I simply sat it in her mouth, like a beached baby whale. Then she stopped kissing me and walked away.

A couple of hours later she emerged from the darkness again. “Have I snogged you yet?” she asked, still evidently overcome by the passion of our first encounter. I hesitated for a moment and then insisted that she hadn’t. She started to approach but recognition came all too quickly. “Yes, I have,” she said and walked away.

The next day I was dropped back in town by a friend’s father. In my head it was the father of the guy whose girlfriend I – and everyone else – had kissed. But the adult mind has a way of tangling up the past to make it more meaningful than it really was and this may be a construction. As I walked home I saw an advert in a Swatch shop showing a pretty teenage girl pulling away from a kiss. ‘You never forget your first kiss,’ it read. ‘You never forget your first Swatch.’

I was overcome with sadness. It was the first genuine moment of regret in my entire life. I had done something which could not be undone. I had spoilt my first kiss on a traitorous girl who could barely remember my face. I had squandered a precious emotional commodity. So I resolved never to make the same mistake again. I promised myself: ‘I will make sure that when I lose my virginity it will be with a woman I love.’

That was a mistake.

The first time is a mess. It’s uncomfortable and often painful for the girl. You feel silly and suddenly weirdly childish. You’re no good at it and you will almost certainly embarrass yourself. I didn’t even know that my partner would come at a different time. I thought the orgasm would somehow transfer to her through some magical osmotic process when I was ready. Basically, the entire thing will be a shambles, so there’s no point inflicting it on someone you love.

I waited patiently for two years, spurning the (admittedly few) offers I received from teenage girls, until I met The One. She dumped me a couple of weeks later.

Young love is frankly a very overrated concept. Very few first loves stay together and those that do tend to spend the rest of their lives wondering why they didn’t play the field a little more. It’s much better to wait for someone you’re comfortable with and then go for it. We’re not talking a stranger down a dark alley or anything like that. Just wait for someone you trust and take a plunge. Making a big poetic deal out of it only increases the inevitable sense of disappointment.

Rule three: Lose it with someone who’s losing it

If there’s any romance to be garnered from your first sexual experience, it’s in the idea that two people might stumble through the darkness together. That’s why the best person to lose your virginity to is someone who is also losing theirs.

Girls are particularly bad at following this rule. Many of you want a man to guide you through it. It’s very common to go home with a man who appears confident and experienced and only mention afterwards (if at all) that it was your first time.

Waiting for love may be self-defeating nonsense, but that’s not to say that the entire event is without meaning. You will remember this for the rest of your life and it will be pleasant for you to think that it meant the same to the other person, that the moment held the same resonance for them. Furthermore, a regrettable power relation emerges from one partner being more experienced. It’s much better to have an equity of cock-up, as it were.

Rule four: Learn to ignore the condom

Much later, when they are older and wiser, men discover that it can sometimes be difficult to maintain an erection with wine in you and a condom on you. In the mean time, its first impact is merely aesthetic horror. It looks disgusting, particularly after the event, and it’s quite common to gaze at it meaningfully and come to certain conclusions about the meaninglessness of the universe.

How could these fiery passions, these scary and blissful sins be reduced to this, a squirt of spunk in a plastic wrapper? How can all those long evenings pondering the flesh end up as a milky discharge in a smelly bag?

Furthermore, it takes away sensation. You’ll be OK for the first five minutes while the lubricant lasts. But after that it will dry out and stick to the skin like an annoying shower curtain. Soon, you will feel nothing.

No-one warns you of this, of course. The entire world is so keen to secure the social and health benefits of condoms that they are promoted without any information about the downside. The downside, however, is horrific. It’s no less than a robbery of sensation at the worst possible moment.

I wish I could tell you how to avoid them, but alas I cannot. You must accept it, as Britain accepted the loss of empire: painful, but ultimately for the best. Leave it as late as possible and dwell on it as little as possible. Once you’re done do not turn its admittedly fascinating appearance into the basis for a philosophical musing. Just bin it, ideally somewhere your parents won’t find it.

And there you have it: a passable introductory guide to the most common pitfalls of cherry loss. Please feel free to now ignore it and make an entirely predictable series of mistakes. That’s how it goes. The squidgy, shameful embarrassment of first time sex will never bow to reason.

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