There's hardly a moment filled with more expectation than your first sexual encounter - it's rife with anxiety, excitement, euphoria, concern, pride… the list goes on and on. There are some basic things that are universal, and some that are a bit less likely to happen, and knowing what's in store for you can really make the whole experience much better.

Your first time. Her first time?

The first thing to know about your first time, is that it's not going to be great - it never is, period. The best thing you can do to improve the experience, is to accept that you're in for something new, not something blissful. Sex is about knowing the other person, knowing what to do, but mostly knowing yourself, and until you've gone through it, you can't know yourself too well. The more sex you have, the better you'll know your own sexual persona, and the better the whole thing will be for you, if you're willing to grow.

The other significant factor, aside from yourself, is your partner. There are two possibilities here (I'm assuming you're having a heterosexual encounter): first, you'll be with a woman who is also uninitiated in the world of sex, and second, she knows more than you.

If your woman is also a virgin, then chances are, it's going to be very awkward. Sex is many times better if at least one person knows what they're doing… if both of you are virgins, then there's one big advantage: she won't know how inept both of you are, any more than you will. If you both know that it's the first time for both of you, then try and reach some kind of understanding that you're just going to do the best you can - if that's too embarrassing to talk about, then don't worry about it.

There are big pros and cons to having a partner who is or is not experienced. If she's relatively new, then she'll be able to lead you a bit, but will still be very much experimenting around with her own body. If she's a real pro, then she'll be the teacher for sure - the downside to this is that women tend to prefer to be with a man who knows what he's doing, so you'd better a) be a quick learner, and b) let her know that it's your first time. The big drawback to both of these scenarios is that she's going to know that it's your first time. Trust me on this, she's going to know - and that means that you'd better tell her about it. If you don't, she'll find out about a minute in, and will likely be very disappointed with the whole thing.

The only possible reason not to tell her - and I don't advocate it, but I'll concede that some men may feel forced to do it - is that you just want to gain experience from it, and don't care what she thinks… and probably won't ever talk to her again, anyway. While this is quite possible, let me stress that sex is much, much better with someone whom you care about, and if you're both open to working at it, it will only get better and better. So don't be in a rush to go out there and break the seal with a hooker.

Always be prepared

Think boy scouts: be prepared. Unless you're having sex for the first time on your honeymoon, you've been going steady for a year, or something similar, then the exact moment that it happens is going to be a little impromptu.

In practical terms, this means assume that it's going to happen any second, and to have the right tools handy at all times. This may sound silly, but there are some basics to cover once you enter the sexual world. I'm going to say this clearly, because almost any woman you're with is going to care about this a lot more than you will. Heed these words: don't stink. I'm not talking metaphors, I'm talking about your smell.

First of all, always have clean underwear on. This isn't mommy talk, this is big. Women will be judging you on this silly, insignificant item. If you can, also have nice undies on, something other than the cheapest starched boxers, or tighty whiteys, or anything with holes in it. For the one woman out there that doesn't think that Calvins are sexy, she will at least admire that you've got some style. When she challenges why a man is wearing designer undies, you shoot right back with "that's right, only the best." This works on her. I know, because I slept with her.

Second order of business is your skin. Let's start with washing: I shouldn't have to tell you to keep your body clean, but I will emphasize that you need to keep your midsection spic and freakin' span. We may make fun of women smelling like fish - and sometimes some of them certainly do - but men can get just as bad. Maybe worse. This is the time to get to know your stench, mister. Figure out how long it takes to get smelly down there, and then make sure that you're washing before that happens. If all it takes is one game of soccer or jogging for an hour, don't worry about that - you're going to be showering after that anyway… but in your casual life, you shouldn't ever get to the point where you reek, or the second you take those boxer-briefs off, she's going to be as repelled as you would be, if she was harboring a cod cannery in her loins.

The remedy is simple, take a shower. If you don't have time, no problem. Just find a bathroom, and rinse yourself out. This is your emergency measure: you're at her place, and you're making out… excuse yourself to the bathroom, rinse off your crotch and butthole with warm water, and uh, try not to dry off with a towel that anyone cares about.

Alright, enough about that. Finally in the stink category, there is cologne. It's a good idea to find out what she thinks about it, but in general know that women like cologne and after-shave, but they hate lots of it. There are exceptions, but most women in the world like a man who smells good, just not from 100 yards out. If you bathe in cologne, she won't come near you. Just keep in mind that women have a more keen sense of smell than we do.

Setting the scene

I'd love to tell you to light candles and put on romantic music, but who knows where this is going to take place. If possible, there are a couple of things you can do to improve the setting - and it's worth it to go out of your way to be in a place where you have control over them. Music is important, and again, smell is too, so having soothing music and incense or candles or something along those lines will help.

So will the ability to lock the doors on the rest of the world. Nothing dampens the mood like being intruded upon (unless they're going to join in on the fun, but until you know what you're doing with one woman, please refrain from any fantasies about more than that). If you can get yourself to someplace like an apartment, a dorm room with a locked door, or your parents' house while they're out of town, then you're talking ideal. And let's make sure they're really out of town, eh?

The rest of the physical setting includes fairly clean sheets, no pictures of naked women around, and an unplugged phone (this means turning off the cell, too). Whatever happens, don't answer the phone. Especially don't answer the phone and say "Oh hey beautiful, I was just thinking about you."

The right time to get it on

What's the right time to do it? Who knows… one second is perfect, the next is a disaster. Just use your intuition to feel out when it's a good time to either boldly go for it, or talk about it. If it's her first time, too, then you should really, really talk about it before you just bust a move on her poor, unsuspecting ass. You're scared about it, but she's petrified.

The most important thing to know about initiating sex, is that it's never just pulling your pants down and hammering away. Women need to get in the mood, in more ways than one. More on this later.

When you've got as much atmosphere prepared as you can, and you're both in the mood, then it's time to be brave, and go for it!

The right tool for the job

Before you actually get to this magical night, there's one big thing you need to take care of, your johnson. Getting the right wrapper is damn important. It's so important, that you want to make sure that you have the situation, erm, in hand, before she gets near it.

This means field testing condoms. See if you can get some free samples - www.trojan.com tends to send out a freebie; you can also get a nice sampling from a Family Planning Clinic. Sometimes pharmacies have one-offs. The point is that you should try a few of them for a couple of reasons, first of all, to figure out how to get them on, and second of all, to find out which ones fit the best. Don't get all fancy with ribbed or anything, just get a basic doodad that's going to stay on, not kill off all sensitivity, and not break. Trust me, you don't want that thing to break.

Once you've got the right condom, practice putting on a couple of them. If you have to use a whole carton in order to get it right, so be it. Just follow the instructions on the box.

Let's get naked

When the time is right, bust that move - and when you do, make sure you're doing two things: 1) be confident. It's critical to the morale of both of you, that you're holding your head high and at least acting like you're in control of yourself. 2) have a sense of humor. When something goes wrong (and it always does), laugh about it, don't freak out. If you're kissing, and you bump teeth, or you drop the condom, hey, that's funny! Laughing about things like this lightens the tension in a big, big way.

Next, keep something in mind: there are two of you, and she's going through a lot of the same things that you are, so always pay attention to her. Always. Sex is about pleasing two people (well, unless you're in an orgy), not just one. The better it is for your partner, the better she'll make it for you.

Here's where I promised to talk more about getting a woman in the mood for sex. For men, sometimes, all it takes to get in the mood, is an incidental hard-on, and if you're in your late teens, that can happen with a stiff breeze, or a tight Hello Kitty! shirt. Women need a lot more warm-up. Being affectionate throughout the day is a good start, but if you're not together that much, then just start out with some touching - anywhere is fine, really. Touching is the first physical connection, so it can come through holding hands, rubbing her back or hair, or just sitting against each other.

Once you're into the romance, AKA kissing, you'll need to really warm her up before intercourse. It might go in this order: casual touching, then kissing and rubbing her body, then kissing her body, then caressing her breasts, then perhaps oral sex on her. You probably don't need to go through all that, but if you do, she will certainly be in the mood.

What do I mean by in the mood? Well, men get aroused and then erect as a result, and women, when they're aroused, they get moist. If a woman isn't wet, then you're not going to be able to get inside without lube, and there isn't much use trying to force your way in, because that's going to be painful for both of you, and it will probably kill your erection in the process. Kissing her all over and telling her how great she is will probably get her excited enough to allow you to enter her, but if she's fairly new to sex, then it might not happen at all. There are also women who just have a hard time getting wet, so be prepared for that, and don't balk at it if it happens, or blame yourself… and especially her. It might be a medical thing, and it might be that she's just not comfortable in the situation.

If you need lube, then don't be embarrassed about it, and make sure that she isn't as well. I've had to use it on occasion, and it doesn't bother me at all - in fact, it can be fun, if you get ones that smell or taste interesting. To start off with, however, you might want to have some basic stuff around, like Astroglide (http://astroglide.com/about/index.html). Another possibility is using saliva, although that doesn't always work. Don't try other stuff (as in common household liquids), it can lead to infections for you or her.