1. The Hymen - What kind of hymen do you have? That will determine how much - if any - bleeding you will have. If you take sex slow and use enough lube, you should not bleed and it should not hurt. Pain during sex means something is being done wrong!! I believe there is a sticky on this forum about the hymen; you should go check it out! If it's not on here then it's on Women's Conditions.

Lube is your best friend; when you two are ready, go buy some from either a sex-toy store or somewhere like Spencer's in the mall.

2. You two could practice other non-vaginal (or anal) forms of sex and mutual-masturbation to get him used to ejaculating when he wants to in your company. The sensation of a vagina may still overwhelm him and that's okay! It happens to a lot of guys. If it happens anyway, just kiss him, let his body relax for a few minutes and ask if he'd like to give it another try

3. Because you're both virgins, you're both likely to have a fairly clumsy first time. He'll slip out; you'll be too dry due to nervousness etc. Just take it slow and relax. I don't care what anyone else says; sex came naturally for me! My body did know what to do once he was inside of me. If you are in love then relax; everything will be fine as long as you go slow and pay attention.

4. My best tip is to try sex in the missionary position first. This position allows you to watch him; it allows him to look at your vulva and find your vaginal entrance by sight and by feel; it lets you help to guide him in with your own hands, etc. And remember the lube!

Oh, as an added note: Orgasm. I know orgasm is probably the last thing on your mind, but do consider this: Most women cannot vaginally orgasm. They can only orgasm from the clitoris. I don't know if you masturbate regularly, but stimulation of the clitoris during sex is most likely the way you will orgasm, so don't be shy about touching it or having him do it!

I wouldn't bother thinking about orgasm the first time lol (because it probably wont happen), just focus on learning what feels good. Eiri's tips are great.

I personally would go for girl on top first because then you have control, or if not first, second. Make it a regular part of sex.

I didn't bleed one bit. You really shouldn't unless you have a hymen, and most women don't. But some do, so if you do bleed don't freak out.

And it shouldn't hurt, it didn't hurt me. If it hurts, make him stop, use some lube, try some more foreplay, and then try again. Don't ever just let him keep going, pain is a sign that something is wrong!

There is no way you can't predict if it's going to bleed or not, if it's going to be pain or not' if you gonna orgasm or not, if your man is going to ejaculate right away or not. Have some lube in hand if you want thought I don't think you will even need it. You will naturally figure it out what the best position is going to be and what to do. I didn't had no lubes when I lost my virginity, neither I put any towels, neither I tried any particular position recommended by anyone. I figured it all on my own. It comes naturally. And it's fun to discover on your own. The experience will be unique. So my advice don't worry about this and just focus in that you will marry this wonderful man.. and if he ejaculates right away so what?? Then he will learn with time. All this things you worry about are superficial when it comes to sex. What will make the first time of sex (and always) a success is the communication, comprehension and love. Never forget this.

I think that everyone is giving good advice. I would say, just be prepared for everything, just in case it happens. I would still use a towel not only in case there's blood, but so that you won't stain the sheets with any other types of fluid.

And even tho u'll be so nervous, just don't think too hard, and really let yourselves get in the mood. Basically, makeout hard core turn each other on, and let the hormones get flowing. It'll make the awkwardness less present.

I used to think waaay too much. You need to just let yourself get horny Also, I am a small girl, so I did bleed a lot initially, but only spotting the days thereafter.

And yes, lube is a good idea.

I'm a small girl and I didn't bleed at all. Size does not determine if you will bleed; it is completely dependent on three things:

1. Your hymen
2. Your comfort level (nerves can clamp up the vagina so tight spaghetti couldn't get it! Secondly, if you're nervous, you won't have any natural lubrication.)
3. Speed (Go SLOW and use lube. If he just jams it in there dry of course it'll bleed!)