Get Naked

Q I’m a 19-year-old college student and, up until a few days ago, I had the biggest fetish for much older men. I went on a dating site and found a man in his mid to late forties whom I e-mailed with for over two months. Thing is, he saw this as a sugar-baby/sugar-daddy arrangement, but all I wanted was a normal relationship. We finally met each other and it went downhill from there. The moment I met him, a feeling of dread washed over me. He showered me with presents (mostly books, gift cards to my favorite stores) and kept insisting that he had “no expectations.” I held my ground and told him that I was not interested in engaging in any sexual activity that night. I felt vulnerable the entire time and was insanely paranoid that he might try to rape me. When he left the hotel I took the liberty of walking around the penthouse suite he reserved for me, and found lube, condoms and small towels in the bedside drawer. I shouldn’t have been so surprised, but that discovery made me feel dirtier than I already felt. I now spend a majority of my time thinking about how disgusted I am with myself (even if nothing physical happened). At my worst, I cry about it. I’m worried that I might need some serious therapy to actually get over this. Furthermore, I don’t know what the proper etiquette is for ending this short-lived affair. Do I give back all the gifts he gave me? (I can’t bear to even look at them.) What should I do?

A First of all, you should stop being so hard on yourself and just be thankful that you escaped unscathed and having learned a valuable lesson. Meeting up with strangers is a dangerous business. And although your intentions may have been to simply meet a nice guy to date, you made some really bad decisions along the way. Meeting at a hotel penthouse suite? Um, that’s what governors do when they want to get their prostitute sex on. Bad decision. Not having a game plan for getting out? Bad decision. Not being clear about the fact that you weren’t in this for a sugar daddy? Really bad decision. You felt dirtier than ever because that dude was trying to turn you into a prostitute for a couple of books and some gift cards. I think you should definitely send all the stuff back and sign up for a few sessions of therapy to figure out how you managed to get yourself into such a bad situation.

Q I’m a straight guy that has had sex with different girls. I’m a senior at NYU. Recently, I met this beautiful, gorgeous girl that has a great body. We had sex three times at her house and honestly, I’ve never had sex like I did with her. I now can say that I have had real sex. She’s very open-minded and extremely wild in bed. But the last time while she was giving me a blow job, she tried to lick my ass, too. No one had ever even touched my asshole before, let alone lick it. It was a weird and awkward situation. I lost my erection instantly. I told her to stop it because I didn’t feel comfortable. She said that I should be more open-minded about it. After we had sex, we started drinking wine, so we ended up on the bed again and this time I allowed her to lick my ass. To be honest with you I kinda like it. Now I regret that decision; what can I do?

A Personally, I think regret should be reserved for things like authorizing an unnecessary war, failing to invest in a new company called Microsoft and choosing not to wear underwear on the day your pant seam rips while picking a pen up off the ground in your boss’s office—not for something as inconsequential as an ass-licking. I think you just need to loosen up a little. Yes, the asshole is often at the center of some nasty biological situations, but it also happens to possess a whole bunch of nerve endings that, when tended to properly, can induce a lot of pleasure. Of course, it’s extremely important to make sure that area is scrubbed clean of all its little E. coli visitors, but once that’s done, there’s really no reason to think of it as anything other than just another part of the body that reacts extremely well to sexing up. Besides, you liked it, you really liked it! So don’t get caught up in those thoughts about what people might think if they knew you let a woman do something like that to you. Just scrub up, spread ’em and enjoy.

Q I am 20 years old, attractive and accomplished, and I recently split from my boyfriend of two years for absolutely no reason other than that he is afraid of getting too tied down so early in his life (we had a flawless relationship otherwise). So like a rational girl, I’ve reentered the dating world, but found all of the guys falling woefully short of my ex. Also, I’ve been spoiled with great sex on a regular basis for the past two years, and being single is an unpleasant shock. My feelings (not to mention my body) are all telling me that I’m meant to be with my ex, perhaps forever. But how exactly do you get a 22-year-old man in the most adventurous and flighty stage of his life to realize this?

A This advice is going to be a bit unconventional. What if, instead of completely breaking things off, you and the ex opened up the relationship a little? You guys would have to come up with the precise terms of this arrangement (when you can sleep with other people, how often to get STD checks to make sure everyone’s having safe sex, what the level of disclosure would be), but if it’s the concept of being completely tied down that’s freaking him out, why not give the guy a little slack? Since you can’t fight his biological urge to have sex with as many women as possible, just roll with it while providing him with something the other girls can’t: a nurturing relationship that seeks to accommodate the needs of both people involved (I can already hear the feminists screaming at me for letting the guy get the better end of this deal). Obviously, this arrangement would not be for everyone, and perhaps he was just using the “I don’t want to settle down so fast” excuse, when in fact there were other reasons he no longer wanted to be in a relationship with you. Still, if you’re happier having him in your life than out of it, there are ways to make that happen so that everyone gets what they want.

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 .