Q My wife and I have been married for ten years. A while back we each made one of those lists, specifying the people we were allowed to have sex with outside of the marriage if the occasion ever arose. We were only allowed five people each, including a couple of celebrities, and the rest were just regular folks from our everyday lives. The other day I hit the jackpot: One of the women on my list—not a celebrity, but that’s all I’m going to divulge—practically threw herself at me. I haven’t done anything about it yet, but my brain has been working overtime thinking about the possibility. Before you accuse me of bullshitting you just to have an affair, I can assure you that these lists were written in good faith and with every intention that we both could abide by them. I haven’t told my wife about this yet, because I’m still trying to think about the best way to go about it. Since she already gave me the go-ahead years ago, maybe it would be better if she didn’t know about it at all. That way she wouldn’t get her feelings hurt, even though she really has no reason to. On the other hand, I don’t want to lie to her, but I really do want to have sex with this list woman. I’ve been 100 percent monogamous in this marriage, and the idea of getting some guilt-free sex from someone else is just too irresistible to pass up. Can you help me sort this out?

A First of all, I think your wife was foolish to allow you to put someone from your everyday life on that list. Those lists are supposed to be mere fantasy material, and filled with people—like Angelina Jolie, Halle Berry and Charlize Theron—who are so unattainable that, if by some ridiculous stroke of luck you were in a position to have sex with them, you’d have to do it because…well, a person just does not pass up Angelina pussy. Allowing the list to include people like your neighborhood Starbucks barista makes a mockery of Angelina’s pussy, and I simply cannot allow that to happen (don’t get me wrong, I love me my Starbucks baristas, but people with nose rings just shouldn’t be on a list like this). Second, if you’re so sure that these lists were made with the full intention that both of you could blithely act on them, then you really shouldn’t have any qualms about telling your wife that your lucky number has come up. I mean, if she was so clear on the explicit meaning behind the creation of these lists, then she’ll know that she can’t and shouldn’t want to stop you. The problem—and the reason you’re writing to me—is that we both know that list was a joke. No matter how earnestly you discussed the lists and signed off on them, neither of you expected anything to come of it. So no, I do not give you license to have guilt-free sex with this list woman based solely on your wife’s “permission” from years ago. Fill her in on the latest wrinkle in your list situation, and if she gives you the green light, so be it. Otherwise, you’ll have to come up with some other dubious mind game in order to give yourself an adulterous night out.

Q I’m a 21-year-old female virgin who’s about to have sex for the first time. The guy I’m seeing knows I’m a virgin, and he’s a little freaked out by the whole thing. He’d rather me be more experienced, because he doesn’t have that much experience either. My concern is that the night is going to turn into a disaster. Do you have any tips for either of us?

A My first tip would be to go into the evening just expecting to have fun. Not expecting to have intercourse, or God forbid, orgasmically satisfying intercourse—just fun. That means the only way you guys could screw things up is if you took it all too seriously. Tip No. 2: Dedicate a whole lot of time to doing the stuff you’ve done before—or if you’re extremely virginal and need things spelled out: the rubby, sucky stuff that anyone with a hand and mouth can do easily. The rubby, sucky stuff will get you both so riled up that you’re probably going to want to take things all the way. That’s cool, but again, don’t let a little fumbling around kill the mood. If he can’t get it in right away, or if you’re not quite wet enough, don’t force things. Just head back to the rubby, sucky stuff and either try again later on, or wait for another day. The biggest mistake people make is that they overthink the whole thing and psych themselves out from just having it happen naturally—you know, the way baboons figure out how to do it. So let’s recap: Just have fun, rub and suck, and lead with your bodies more than your brains.

Don’t ask me how I stumbled across this, but I found the coolest website ever. It’s called Sex in Christ, and its whole purpose is to give God-fearing individuals biblical authorization to do things like have anal sex. I recently spent a whole weekend day going back and forth between reading these great tips and watching the toddler who says “buhlud” on YouTube. That’s my idea of living. Here, check out a sample:

Anal Sex in Accordance with God’s Will

Are you saving yourself for your wedding night? The Devil wants you to fail, that’s why he puts stumbling blocks in your way. But God wants you to succeed, and that’s why he has given us an alternative to intercourse before marriage: anal sex. …You may be shocked at first by this idea. Isn’t anal sex (sodomy) forbidden by the Bible? Isn’t anal sex dirty? What’s the difference between having anal sex before marriage and having regular intercourse? Let’s address these issues by debunking some myths about anal sex and God’s will.

“I thought the Bible said anal sex was a sin.”

This is a common misconception. Anal sex is confusing to many Christians because of the attention paid to the Bible’s condemnation of homosexual acts. However, it’s important to realize that these often quoted scriptures refer only to sexual acts between two men. …Lamentations 2:10 describes how “The virgins of Jerusalem have bowed their heads to the ground,” indicating how virginal maidens should position themselves to receive anal sex. Another suggestive scripture tells of a woman’s pride in her “valley” (referring to her buttocks and the cleft between them) and entices her lover to ejaculate against her backside: “How boastful you are about the valleys! O backsliding daughter who trusts in her treasures, [saying,] ‘ Who will come against me?’ (Jeremiah 49:4) And in the Song of Songs, the lover urges his mate to allow him to enter her from behind: “Draw me after you, let us make haste.” (Song of Solomon 1:4)

I’ll show you, devil! I don’t care how sore my ass gets, I’m going to save myself for marriage. Wow, had I known the Bible was that hot, I wouldn’t have avoided reading it all these years.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com. Check out “Sex on the Street” with Jamie Bufalino at timeoutnewyork.tv.

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