If there’s any topic that a young nerd-boy obsesses about, it’s losing his virginity. No matter how long he has been waiting for it, it’s automatically too long. Every single one of his friends who crosses that magical finish line before him – and they always seem to come in waves, don’t they? – is just further reinforcing the idea that there’s something wrong. The magical day that he makes the transition from boy to man – complete with George Thorogood background music and XP bonus notifications – is the culmination of years of pent up angst, anxiety and frustration.
But for all of the mental energy that young men and women are spending imagining losing it, they are often unprepared for the realities of losing their virginity. Just because you’ve pictured all of the fun sweaty moments doesn’t mean you know what to expect. It’s more than gasping noises and swelling John Williams themes in the background, and knowing what to expect can mean the difference between awkward, uncomfortable moments that will kill the mood and a first time you’ll be bragging about for years to come.
It’s a staple in any coming-of-age comedy: every time the guy’s about to (finally!) lose his virginity, something goes wrong. His “lucky” condom – the one that he’s been carrying in his wallet for the last five years – disintegrates. The phone rings and he’s trying to continue making out with his girlfriend while his mother rambles on the answering machine. Well-meaning roommates come home at the exact wrong moment. The make-out mix on his computer suddenly starts playing the Power Rangers theme. He needs to run out of the hotel room for one quick errand and not only does he get locked out, he can’t find it. Hilarity ensues.
Of course, it’s not so funny when you’re the poor son-of-a-bitch that this is happening to.
You need to understand this as soon as possible: the Universe is powered by cruel irony and Murphy’s Law. Anything that can go wrong to disrupt your first time will. Nobody appreciates the stories of how they almost lost their virginity (at least, until years later) so you need to embrace your inner Batman and be crazy prepared.
At a bare minimum you will want towels, water, mouthwash and condoms. Yes, condoms, plural. You’ll need them. In the moment when you need them, you will quite likely be at a state where your hand-eye coordination goes out the goddamned window. The last thing you need is to have the big night called on account of fumbling your only condom as you’re trying to put it on. And don’t think you’re going to slip by with the ones you stashed years ago; condoms expire and the closer they are to the expiration date, the more likely they are to break on you – literally.
If you feel like going the extra mile, get some form of water-based lubricant. Besides helping with any issues of penetration, a couple of drops into the tip of the condom can help mitigate any loss-of-sensitivity issues you may have.
Also, take steps to minimize any possible interruptions. This means that all cellphones are set to silent, land lines are off the hook, the answering machine is turned off, roommates are waved off and – critically – the door is locked. There’s no better mood-killer than someone stumbling in at an inopportune moment.
It’s impossible to plan for every eventuality, but you can keep the boner-destroyer moments to a minimum with some advance work.
Manage Your Expectations Accordingly
You may have been waiting for this all of your life, but you’re about to find out the differences between fantasy and reality and the collision of the two can be a shock to people who aren’t expecting it.
To start with: you’re not going to last very long. At all. Actual sex will last minutes if you’re lucky… and to be perfectly honest, she’s not going to cum at all. This isn’t anything to be ashamed of; you literally have never done this before. Nobody is an expert right off the bat – like everything else in life, sex takes practice and repetition in order to improve. Malcom Gladwell famously postulated that it takes 10,000 hours of practice to master a skill and you’ve only just started.
The next thing to keep in mind is that you’re dealing with human bodies and everything that this entails. That means there are going to be smells that you’re not used to, sensations that you didn’t expect, physical reactions that you had no idea could happen. It’s only natural that you might be put off at first – it’s all going to be strange to you at first and that can be uncomfortable. Don’t let it stress you out and don’t complain about them. Nobody wants to hear someone make a comment about smell or taste at a moment like that. The best thing you can do with any of it is to be relaxed and take things as they comes; you may be surprised, but the better you are at just rolling with the moment and not letting the newness distract you or put you off, the better off you will be.
Having “everything but” experience – that is, everything but sex – will help you get used to this in advance. Actual sex won’t be as intimidating when you’ve had some practical experience with heavy duty make-out sessions and oral sex, and you’ll be far more comfortable not just with her body and it’s attendent experiences but your own.
A girl’s first time can be uncomfortable, and a lot of virgin guys worry about causing her pain. Don’t let it stress you out; it can be painful, but it’s quick and manageable, and it’s easy for guys to help make it as painless as possible. The key is to be gentle and to go slow. Check in with her about how she feels and what you can do differently if need be.