Just do it. When you get into it, it will all just take care of itself.
Imho, the best way to wreck a sexual experience (particularly the first time) is to overthink everything and anything about it.
Let it happen.
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Get some lube. If it’s her first time, she’ll probably need it, and if she doesn’t, well, it’s a good thing to have just in case.
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Let her control speed, etc. It’s not necessarily the breaking of the hymen that hurts, it’s the expanding of the skin and muscles in that area. (This is, again, assuming it’s her first time as well.)
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Don’t expect sex to be like it is on tv or in the movies – especially your first time! It’s not that easy, it’s somewhat messy, and your movements won’t be choreographed. I hope you’re both comfortable enough to laugh at yourselves, because it can be kind of funny. “Okay, move your leg over there. No, farther. Umm, now move your arm. No, the other arm… okay, that won’t work.” And that’s okay – it’s just as fun when you’re laughing, and often a lot more memorable.
And I agree with Giraffe – if you expect the first time to be awful, you’re unlikely to be disappointed, and you may be pleasantly surprised!
Also, disregard everything you’ve seen in porno movies. They are not reality. They are staged fantasy, period. If you consume them in that spirit, they’re fine. If you treat them as educational documentaries, you’ll have a rude awakening. Maybe not the first time, depending on how insecure and compliant your partner is, but eventually you’ll be with somebody who asks you, “Uh, what the hell do you think you’re doing?”
Definitely second the recommendations for foreplay – lots and lots of foreplay. (This, by the way, assumes you’re a heterosexual male looking for advice with females.) The hotter you make the woman, the easier things will go, so to speak, and the more she’ll enjoy it. I was a dinkus with my first sex partner, and she didn’t say anything for the first few weeks, thinking it was supposed to be dry and uncomfortable until we got rolling. I didn’t know either. Now, from my mistake, you know better.
What kind of foreplay? Let the woman tell you. Try cunnilingus, and ask her to tell you what feels good. With feedback, you’ll figure it out pretty fast – not too fast there, not too much on the clit too fast, don’t bite that, rub there, and so on. And don’t look for a guide here: Every woman is different. Some women actually don’t enjoy having cunnilingus performed on them (and those who think, ah, you just don’t know what you’re missing, I bet I can change her mind, are jerks).
You’ll note I’m not talking about what you will feel, because good sex isn’t really about that. Your body knows the motions. Once you achieve penetration, your hips will figure it out. (By the way, it’s not uncommon for inexperienced men to “poke around a bit” before slipping inside. Let the woman help.)
Oh, and another thing: Young men are notorious for physical virility, so don’t worry if you come too fast. In fact, you can turn this to your advantage. If you’ve got the time, and you’re with someone you really like and trust and with whom you can spend a lot of time, try having a masturbatory orgasm first (preferably via her hand, not yours, but whatever turns you on). Then keep fooling around, and you’ll be hard again and ready to go before you know it, and you’ll last a lot longer. I’m in my mid-30’s, and although I’m nowhere near as much of a horndog as I was when I was younger, I can still achieve a second erection and orgasm around half an hour after the first one. It’s not about the orgasm, anyway; after all these years, I sort of feel disappointed when the climax arrives, because it means an end to the preceding wonderfulness.
But I’ll say again what I said at the top: Forget the porn. It will steer you wrong if you treat it too seriously.
I second this.
Also, be prepared for blood.
And take it slow.
Gosh. When it was my first time , we had no preparation oher than the condom he kept in his wallet , should the need ever arise. I always felt that something like that should be in the moment , not studied for and worried about. Although now that I think about it, maybe we should have thought ahead, considering how uncomfortable we both were at first.
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Listen to your partner.
Listen to your partner.
Listen to your partner.
Oh, and be sure to pick a partner who is not going to turn into a manipulative psycho-beast and spend the next few weeks alternately demanding that you marry him or her and bursting into tears (yes, this did happen to me – with a guy). Somebody sane, normal, and experienced is good.
I think it might also depend on how far you’ve gone with the person before. For four months before we actually had intercourse we did everything else and really got to know each other’s bodies…it definitely relieved the stress and pressure of the first time.
my best advice? laugh.
yes, sex is romantic, but (well, unless you’re catholic, maybe) sex is also supposed to be FUN. and it’s not fun when something goes wrong, you panic, and you kill the mood. so if something weird happens, just laugh and be deliriously happy that you are sharing something very special with a very special someone.
I lost my virginity to a virgin and it was a great experience. I second the “masturbate before you go in” nominations because most guys last about two thrusts their first time. Also, make sure she orgasms! I know tons of girls who have never had an orgasm with their boyfriends or lovers because the guys were too focused on themselves.
And above all else, communicate.
Agreed! My first time was with a guy 24 years my senior, and I was shit scared that he would be distinctly unimpressed with my performance. As it is, I have hangups about my body, so I was a bag of nerves by the time we got down to it.
Got to hand it to the guy, he really put me at ease, and we just took things slowly. Naturally I felt a little clumsy, but he was very patient and gave a little guidance at just the right times. Despite the vast amount of prior experience he had, there were no expectations placed upon me, and he allowed me to learn the ropes at my own pace.
All in all, much better than I expected. Just allow yourselves plenty of time so you don’t have to rush things; we spent the whole weekend in bed, rather than trying to cram as much as possible into a hurried 2-hour session, and I look back very fondly on the whole experience.
Her vagina is paint-by-numbers?
Keep a roll of tape handy in case she gets a puncture.
You should’ve seen my mental images the split second before I figured out you meant a rubber doll.
PS – Astroglide is a pretty decent lubricant AND you can buy it in Target. KY is just… gross. Vaseline destroys condoms, I hope you know that. So does whipped cream or nearly anything made mostly of fat or oil.
“Listen to your partner.”
I have to skip that step.
I do wonder how far we can discuss this matter with someone who may/may not be an adult?
pepperlandgirl yes, truly lube is needed.
My first time, I was 26. All we had handy was shampoo.
This piece of advise can be used not in just sex, but in every day life. 
[voice over]
“Got to give a speech before two hundred CEO’s? Masturbate before you go in.”
“Going to Granny’s for *Another * Thanksgiving dinner? Masturbate before you go in!”
“Panic attack got cha before your SAT’s? Masturbate before you go in.”
(snort)
Why are you telling or reminiscing with handy of this experience?
–Surely you jest.