Me (20f) with my boyfriend (21m): How are you 'supposed' to lose your virginity?

A few pieces of advice -

Have him practice with the condoms when he's masturbating. Just so he knows how to put them on and off comfortably.

If you have trouble with tampons, GET THE LUBE. You may have no problem with vaginal wetness, but you're going to be glad you have a little extra lube, especially since nervousness over the first time/being caught is likely to actually dry you up a bit. Get the lube.

Hotels are expensive. "No tell motels" are not. Find a motel that does "4 hour naps". You're near a Christian university? I guarantee, there's a motel of this kind within a couple of miles. They make their bank on students from your school, guaranteed. Just bring your own sheet and lay it on the bed. Remove the fear of getting caught, it'll make things go so much more smoothly and allow you two to take your time.

You told him you want some foreplay. That's not enough. Make sure you both understand what you MEAN by foreplay. Don't assume he knows. SHOW HIM if you have to. And have a good idea of what you like. That's what masturbation is for - learning what feels good to you. Then show him how to do those things.

Don't expect to orgasm. You might, and it'll be a nice surprise. Truth is, you probably won't though. Women are notoriously hard to bring to orgasm, especially without (skilled) clitoral stimulation. Talk about this beforehand with your boyfriend so HE isn't feeling disappointed if you don't orgasm. And for fuck's sake, DON'T FAKE IT. Not now, not ever.

Faking it is a huge disservice too many of us do, to ourselves AND to men. How can we expect them to BE good lovers if we're not willing to be honest about what pleases us? If his ego is so poor that he can't handle not being able to get you off, he's not worth dating - let alone having sex with - to begin with. Work TOGETHER to find out how to get you off.

Oh, and don't get drunk beforehand. Seriously. Nothing taints a memory so crappily as the smell of sour booze on your partner's breath when you're trying to be intimate.

/r/relationships Thread