I've been reading your column for about three years now and I'm excited to finally be able to send in a question. I'm a twenty-five-year-old virgin and this coming Saturday I plan on having sex for the first time. My virginity isn't wrapped up in religion or tradition of any sort. I'm a well adjusted liberal atheist living in one of the reddest states in the union. I've had opportunities to have sex in the past, but I just wasn't attracted enough to the men I was dating to let them get that far. I've finally found a guy who's great all around. Funny, sweet, gentle, and an amazing kisser. We spent last night together and did a little heavy petting. It was very enjoyable and he took things nice and slow.

I know I've got the right guy for the job, now all I need are a few tips from the expert! What items should I have on hand to make the experience as safe and painless as possible? I've got lube and condoms covered but I have the nagging feeling I'm forgetting something. I also want to make sure I don't stain his sheets by bleeding on them, but showing up with a rubber mattress cover might be a bit of a mood killer. Oh, and how long should I wait before I let my kink come out to play? Should my first time be vanilla, or do I have other options? What do you say Dan, can you help a girl out?

Giggity Giggity Girl

P.S. I tend to pepper my speech with some of your acronyms such as GGG and DTMFA. Living in Idaho, I'm mostly met with blank stares. One night while having a conversation, my boyfriend began to talk about pegging, santorum, and saddle-backing. I had managed to find a kindred spirit!

My response after the jump...


I'm thinking your first time should be relatively vanilla.

If you have a few simple kinks that help get you aroused and off, GGG, perhaps you can subtly work them in around the edges. But the more complicated the kink, the more skill a person needs to incorporate it into sex. (Kink + Sex = Doing Two Things At Once) And seeing as you can't be all that skilled at the moment—being a virgin and all—and seeing as your boyfriend is probably intimidated enough by the whole OMG-I'm-her-first thing, I would advise you to save your kinks for your second or third time.

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And he does know this is your first time, right? You did tell him about the job he'll be doing for you, right?

As for bleeding, well, that's a possibility. You could bring along a rubber sheet for his bed, I suppose, or attempt to place a towel and then check to make sure it stays put. But here's better idea: fuck like you don't give a shit about his sheets. Because in the grand scheme of things, GGG, the damage he's going to do to your hymen is much more significant than any damage you might do to his lousy old sheets. If he's concerned about his sheets—and I can't imagine that a straight man in his position would be—then go out and buy some new ones just for the occasion.

And lay in a nice bottle of champagne too, GGG, for after, not before, the sex. Good luck! Have fun! God bless!