Sex For Beginners

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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.

You don't want to know what my original joke was.

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.

Be Prepared

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.

"It was all fine until you started making Star Wars jokes, Brad."

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.


  1. and bodily fluids []

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  • Maciek of Poland

    Where do you keep getting those pictures? They are great!


    Any tips for a fellow who has to confess strong fillings (love) to his love intrest very soon?

  • ohsnap

    Also, I like to keep a bottle of water in my bedroom. It's thirsty work, no joke!

    • Struck

      My boyfriend does too…it's adorable. 🙂 First thing he grabs after finishing, haha.

  • SabsDkPrncs

    I know this post is over a month old, but there's something that's very important to me, as a female: Don't lie about being a virgin. If you lie about being a virgin to me, either by saying you've had lots of girls or just implying you're experienced, then tell me after you lasted 10 seconds that I was your first, it's not a relationship I want to be in. Not because you aren't experienced, because it shows a lack of confidence, in yourself and in me. Plus, your first time will be A LOT better if you're up front about it.

    Yeah, this has happened to me more than once.

    • absolutely like your view about sex ……………….

    • RobinJ

      I absolutely agree with @SabsSKPrncs,
      as I girl I would rather have a guy being honest to me.
      Being honest shows that you trust and respect the other.
      And… woman love man who are confident in being themselves : ).

      When a girl wants to have sex with you, it usually means that she really likes you.
      If a woman rejects you just because you’re a virgin, there really is something wrong with the woman, not you.

  • Schim

    Some less sexy, but very practical advice – both of you need to go pee and wipe afterwards. It will greatly reduce your chances of getting a Urinary Tract Infection (UTI) if you flush out the urethra. I know that my school's sex ed class did not educate us about sex, so yours probably didn't either, and I hope this helps prevent that nasty-burning-pain-while-peeing sensation.

  • Sarah

    Ah, first time sex. My first time was great, but the gf who shared hers with me… wasn't so lucky.

    We were on holiday with her sister and sister's boyfriend, staying in separate rooms, and had swapped room keys since we had each others' stuff in our suitcases. We happened to be in sis's room when things got excited, and figured that was fine – sis and her boyfriend were out, and weren't going to be back for hours (can you tell where this is going yet?). Midway through things, gf got a text, I told her to ignore it. Yes, this means it was my fault. Once we're done, she decides to read the text, which is now five or ten minutes old. Sis must have eaten something dodgy and has the shits. Is on the way back to the hotel now. We didn't *quite* manage to get all our clothes back on before sis burst through the door and hurtled straight into the bathroom, while boyfriend stood in the open doorway to the public hall trying to decide where to put his eyes.

    And the relevance of the story? Well, it's funny. And allows me to point out that even if your first time DOES go horribly wrong, there are many, many, many more times to come, and they will get progressively better over time. If I were that kind of girl, I'd have married this chick just for all the amazing sex we had WITHOUT any hapless observers.

    Oh, and also, don't be That Guy whose first thought following sex is "food!", no matter how many calories you've burned.

    • Dr. NerdLove

      Oh, and also, don't be That Guy whose first thought following sex is "food!", no matter how many calories you've burned.

      Wait, is that actually a thing now?

  • jessica

    Ohh, yes the going for food thig does happen.. biggest possible moment ruiner & kills majority of the day/night after!! my bf has done it & goddamn was i pissed.. lmao. just never, ever do it. cuddle time is necessary after sex, especially the first time. down just down play it bc it adds to the intimacy & makes it a hell of alot more fullfilling. never forget it!!

  • Emily

    our first time was hard and i was not wet enough



  • Van1

    ( I am a straight male) i have never had sex so far, but I am going to do it soon with a girl I am seeing. I have some questions: 1) I know I am not going to last long, but to make that up, should I do long foreplay ? Also, during my first time sex with my gf, is it okay to lick her vagina? Or will it seem very bad in her eyes? 2) If I practice holding my pee while peeing, do you think it is going help me holding my cum, during the penetration?

    • Dr_NerdLove

      1) The length of time people last for the first time is variable. Some people will cum quickly, some will take far longer than they expect. Don't try to marathon it -go with the experience. And as a rule of thumb, more foreplay is always a good idea.2) The best thing you can offer during sex, regardless of whether it's your first or 500th time is an open mind, a willingness to take instruction without letting your ego get in the way and a can-do attitude.3) Yes. Strengthening the PC muscle – the muscle that cuts off urination when you flex it – can help you sexually. It will strengthen your erection and is a effective way of controlling your orgasm.

    • letho

      Protip: wank at the morning, might help last longer.
      A lot of guys which i fucked went flabby for a short time. Might be that they were nervous, i dont know (most of themm werent virgins as far as i know.) If that happens -shit happens, dont panic. Will get better (as far as my experience goes) one never got 100% hard-second time went definately better.
      So you might just remember that it can happen-and that this isnt a problem-unless your partner is an asshole(and not the right one to fuck thrn, imho)
      Also- please dont lie about virginity-there are actually women like myself who like “deflowering(the reaction is often a sense of wonder and awe which feels very true)

  • Glides

    Despite being the infamous "v-word" (which has scared off every cute girl at my college, yay), I was happy to know that I already knew most of the stuff you talked about.
    I'll have to admit that I began laughing like a hyena when I saw the "willing female friend" one. There's no such thing as a "willing female friend."
    Either way, the moral of this article: no matter what, my first time is going to suck immensely, especially for the girl.
    Besides, if she's not getting anything out of this, why the hell would she even bother? That's why you can only lose your virginity with another virgin, because at least she won't know how terrible you will likely be in bed.

    • eselle28

      That's really defeatist thinking, and it's also not true. I've had sex with several virgins. I wasn't a virgin myself. While none of the experiences were the best sex of my life, they ranged from "fine" to "pretty enjoyable." It is possible for a virgin to not be absolutely terrible at sex, especially if he's willing to listen and doesn't freak out at any mishaps. Bodies sometimes do strange things, even if you're not a virgin. It doesn't have to ruin things if you don't let it.

      As for what she's getting out of it, she's getting the same things that you are: she gets to have sex with someone she likes and is attracted to and perhaps is also taking a step toward building a romantic relationship. If neither of those is your main goal, then yeah, the sex probably will suck.

  • a female friend

    you dont have to lose your virginity to another virgin! that's ridiculous I know I did not, and there are people out there who would not be put off by it either. For one thing, experience does not tell you whether or not someone will be any good in bed! It's about being considerate and communicative, and knowledgeable is good too – you don't necessarily gain knowledge through experience, seriously, people who have ample "experience" can be selfish and poor lovers!
    Why would you assume it would suck immensely for the girl? If you are willing to put time and effort into her pleasure and also happily take instruction and perhaps ask for it I don't think it would suck!
    Women usually can't get off on penetration…so if you know this and are prepared to spend more time on other activites first most women (well I can only really speak for myself but still..) would be satisfied before any actual intercourse has begun. You can find out about anatomy and the theory of giving pleasure to another without actually having had sex.
    In a nutshell if you understand that the majority of women require direct cliteral contact to orgasm and are prepared to put effort into making it a good experience for your partner how wrong can you go?

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