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.
Insert Tab A Into Lot B. Repeat As Needed.
Once again: slow your roll, son. Just because the moment’s upon you doesn’t mean that you should rush straight for penetration. You’re only getting this moment once, so you should take your time and enjoy it. That means foreplay, foreplay, foreplay. Make out, let hands and mouths roam over everything not just a bee-line to the nipples or to oral. Savor every inch and sensation and just let the moment build. Check your ego at the door; the sooner you learn to ask what she likes and how she likes it, the better you will do now and in the future. A willingness to take direction cheerfully and a can-do attitude will not only make up for inexperience but help ensure a repeat performance… and possibly even a recommendation to others.
Actual penetration isn’t going to be as easy as movies would convince you it would be; without a guiding hand or two, you can expect a few false starts as you’re trying to fit everything together. Don’t be afraid to ask for a little help; her help will make everything go smoother than just stabbing randomly and hoping to hit the bullseye.
Don’t stress the act itself. You’re a novice at this – nobody is going to be expecting a John Holmes-esque performance of multiple positions and a string of screaming orgasms prior to you finishing. Don’t stress about trying multiple positions or finding the perfect rhythm; slow and steady will serve you perfectly well until you have a little more experience under your belt… as it were. If she’s more experienced than you, then she may have some suggestions for you. Try them, you may find that you like the results and you’ll have some ideas for next time.
And remember: as long as you’re both laughing and having fun, you can’t do anything wrong. Any awkwardness or fumbling is going to pass and you’ll laugh about them afterwards.
Handle The Aftermath Before The Afterglow
Congratulations! You’ve done the deed! You’ve popped your cherry! You’ve traded in your v-card, you’ve become a man, etc. etc. But just because you blew your load doesn’t mean that you’re done.
First things first: you need to withdraw, carefully. You don’t need to pull out as soon as you get off, but you don’t want to linger; you’re going to deflate, which increases the odds of both slippage and spillage. Grab the base of the condom and hold on as you pull out. The last thing you want now is for the condom to slip off. Dispose of it properly; this means it goes in the trash, not flushed down the toilet. A clogged john isn’t anyone’s idea of the capper to a perfect evening.
You’re also going to want to manage the clean-up… so hopefully you have those towels close at hand. A warm wash-cloth probably wouldn’t be unwelcome either, if you have easy access to them.
Now that the deed is done, it’s time to take a few minutes and just let it sink in; it may not have been exactly as you always thought it would have gone, but it was pretty damned amazing, wasn’t it?
Post-Sex Etiquette OR How To Make Sure Your First Time Means There Will Be A Second Time.
A general rule of thumb is to stay the night afterwards. Obviously, this is going to depend on your circumstances; spending the night together isn’t an option if you’ve got 30 minutes before your folks come home or you’ve snuck off during a party. But if you have the option, you should take it; after all, it means there’s more sex in store in the morning, and who doesn’t want that?
Regardless of whether you spend the entire night together or if you have to sneak back home, you owe – at the bare minimum – an extremely grateful phone call the next day before you run out and collect high-fives from all of your buddies… and that’s if you can’t manage to get together in person. Whether your first time was with your girlfriend, a willing female friend or a last-minute hook-up, you’ve shared an amazing experience1 and you should acknowledge this. Don’t fear any post-sexual weirdness or awkwardness; how “weird” it will be afterwards is entirely up to the two of you and how you handle it. If you act like you’ve done something shameful, then of course there will be weirdness. The deed was done and it was awesome and if you act normal, it will be normal.
Remember: don’t be an asshole afterwards; you may be wanting to run out and brag to your friends, but she was involved just as much as you were. Be a gentleman. After all, how you handle things afterwards will determine whether there will be a second time… or even a third.
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