Have an orgasm. Yes, before you start having sex, you should give yourself an orgasm. It’s important to know what feels good to you before you can show another person what feels good to you.
Know the other person’s sexual history. And I don’t mean just vaginal intercourse for this one!
Know the other person’s STD status, as well as your own. The only way to know this for sure is to be tested! And if you’re both virgins, well, you’re not going to be for long. You might as well get that scary first STD testing out of the way so you’ll know what to expect next time around.
Talk about exactly what STD protection and birth control you will be using. These two issues go hand-in-hand (for heterosexual couples), and it is the domain of both parties to be intimately involved.
If you are part of a heterosexual couple, talk about what happens if the woman gets pregnant. Here are a few options to talk about, in alphabetical order: abortion, adoption, raising the kid alone, raising the kid together. With the understanding that reality is different than the theoretical, make sure you’re both on the same theoretical page.
Have your best friend’s blessing. We can rarely see someone we’re in love with clearly. It is often our best friends who can see our lovers and our potential lovers for who they really are. Listen to what your best friend has to say, and take it to heart. If it’s not what you wanted to hear, give it some time. Wait a month. A good relationship will be able to withstand another month before having sex. Then ask a different friend, and see what they have to say.
Meet your partner’s parents. At the very least, make sure you know why you haven’t met your them. The best sex comes out of knowing someone well, and knowing someone’s family is an important part of knowing them. (Even if they’re really, really different from their family.)
Be comfortable being naked in front of each other. You don’t actually have to strip down in broad daylight to make sure you’ve reached this milestone, but it sure helps!
Have condoms on hand. Make sure they fit right, that they’re within the expiration date, and that they haven’t been exposed to extreme conditions (like the inside of a really hot car). Condoms should be part of any respectful sexual relationship. There need be no assumption of hook ups outside of the relationship, just an assumption of good sexual habits being made and kept.
Make sure that your partner has done all of these things too. Part of a happy, healthy sexual encounter is taking care of everyone’s emotional needs and physical health. Both people need to pay attention to themselves and to their partner. That way each person has two people looking out for them. It’s just the best way to do things.