I'm on hiatus while working on a manuscript for a new book. In the meantime, please enjoy these classic Savage Love letters pulled from previous columns. I will be back October 1st, when the book is finished. —Dan

Originally published March 12, 2009:

I'm 21, female, and pretty experienced. The guy I'm dating now is 23 and a virgin. I'd really like to avoid some of the awkwardness that I'm sure is going to arise, seeing as I'm his first. (And has arisen—the first time we attempted to do the deed, he was so nervous he couldn't stay hard; he also thought he was "in" when, in reality, he was humping my leg.) I'm at a loss. Obviously this is going to take a lot of communication in the moment; aside from that, do you have any advice for how to make this less awkward for both of us?

First Isn't Really Sexy Time

My response after the jump...

Mess around a few times—at least a half a dozen times—with vaginal penetration off the menu, ratcheting down the performance anxiety for your boy. Once he's seen that, yes, his dick does work—yes we can get hard, yes we can stay hard, yes we can blow a load with a woman in the room—then you can move on to vaginal intercourse. And take control, FIRST: Tell him—as sexily as possible—what you're going to do before you get started, tell him what you're doing while you're doing it, and then you can tell him when he's "in" instead of letting him guess.

And, finally, a little required reading for the virgins out there and the people who are about to fuck some sense into them: The Virgin Project. Illustrators K. D. Boze and Stasia Kato interviewed all sorts of people—gay, straight, bi; young, old, ancient—about their loss-of-virginity experiences. The illustrated stories in The Virgin Project are moving, hilarious, and heartbreaking in turn—sometimes all three at once—and knowing that everyone's first time is awkward, and that some folks' first times are unpleasant, and that most of us survive them, might be good for your virgin, FIRST. It couldn't hurt you to be reminded of those things, either.