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Q I was a 37-year-old anal-sex virgin up until last weekend. It happened and I totally freaked out. It hurt like hell and I jumped away and started crying. Then I demanded that my boyfriend take off the handcuffs and I ripped off my pleather bustier. I just wanted everything having to do with sex to get away from me. I have no problem not having anal sex again (gee, why?), but I want to be able to satisfy my boyfriend, who does like [giving and receiving] anal sex. We have a dildo, but I also want to be able to use my fingers in a pleasurable way. I’ve heard that if you press in the direction of the prostate it feels really good for the guy. Well, my guy has had his prostate removed. Will this still work? If so, how do you do it? Which direction do you press? And if the prostate thing is out the window, what else might be pleasurable? I know bringing up my feelings about anal sex seems arbitrary, it is just that I don’t really know what feels good—if anything—for me.
A Okay, before we head off in any other direction, I feel the need to point out that (as my idol, Dr. Jack Morin, author of Anal Pleasure & Health always says) if you’re having anal sex correctly, there should be no pain at all. Too often people rush into the penetration part of anal sex, when there needs to be a healthy amount of foreplay (stimulating and relaxing the anal muscles, making sure there’s plenty of lubrication, etc.) to prepare the receiver for its impending visitor. Even though you had a bad first experience, I don’t want you to forever forgo having anal sex just because you think it’s unavoidably painful. As far as prostate massage technique goes, one of the coolest sites I’ve found on the subject is whitelotuseast.com/sacredspotmassage.htm. That will give you all the info you need about preparation, positioning and hand maneuvering. Since your boyfriend had his prostate removed, I wouldn’t worry so much about trying to locate the exact area it once occupied. The anal canal is filled with nerve endings that can all benefit from a gentle fondling, so the prostate’s not the only game in town. I would just go slowly, and ask him a lot of questions about what he likes as you proceed. In other words, do the things that will make his anal experience far better than the slam-bam rush job he gave you.
Q I’m a 22-year-old girl dating a guy who is 24, and it’s both of our first real relationships. It’s been almost three months and we’re pretty solidly seeing each other three to four nights a week (always spending the night at my place because of his home situation), and often spending the better part of the weekend together. We’ve been exclusive pretty much from the start and sometimes I fear that it’s all happening too fast, but our philosophy is, “if it feels good, why stop?” However, I’m becoming increasingly frustrated with my roommate situation. Right before New Year’s, I moved to the UWS with my good friend and everything was going great until I started seeing this guy. Now, it’s not that I don’t respect her feelings and opinions, but she has imposed rules about how many times a week we can have people over (two nights—one weekend night and one weeknight) and this is starting to be a real problem. She refuses to budge on how many nights my guy comes over, and so I’m forced to sneak him in the extra nights we want to see each other. We had a noise problem before, but he and I now work to keep it down (which, I must say, is very boring! We both like to be loud). Part of me understands that me having someone over a lot is uncomfortable, but another part of me remembers what college was like—when I had to share a room with someone, not just an apartment—and think, We have separate bedrooms so as long as we’re not disturbing anyone, what’s the big deal if I want to have him over two nights or seven nights? But she’s threatened to move out if I have him over any more, and I can’t afford the place on my own. What do I do?
A I hate to be a buzzkill—especially since I just received a one-line e-mail from someone asking, “Why are you such a prude?”—but come on, this is not college anymore. It’s hard enough dealing with the cramped state of New York City housing as it is, without adding an extra, non–rent paying body to the equation. That being said, I feel like two nights per week may be a little on the low side. I would think two weeknights and one weekend night sounds more realistic and thoroughly manageable. The thing is, you probably screwed yourself with that little “noise problem” you referred to. Your roommate is probably pissed off about having to hear you fuck all night long, so she’s trying to punish you a little bit by imposing these draconian rules. I know you guys are in the throes of lust, but instead of getting depressed about not being able to sleep with each other every single night, look at it as an opportunity to make sure things aren’t moving too fast and causing premature burnout. Oh yeah, and make sure you make the most of the times when you’re roommate is not around, so you can bang each other’s brains out at a decibel level more to your liking.
One final word: Okay, okay, maybe I screwed up on the subject of vaginal rejuvenation. My in-box is filled with letters such as:
Gotta say, your response to the 45-year-old woman inquiring about vaginal rejuvenation was weaker than her birth canal. As the son of a gynecologist, I agree that vaginal rejuvenation should not be given as a “gift” to forlorn husbands, as your reader alludes. However, it is absolutely an option for women seeking to increase their pleasure during sex—especially after childbirth, since Kegel exercises don’t always work. Until you get a medical degree, I suggest you limit your advice regarding vaginal surgery. We know you’re no pussy, but don’t tell women how to handle theirs.
Ouch. That last part was a little harsh—especially coming from the son of a gynecologist, rather than an actual gynecologist. In any case, perhaps I was a bit too dismissive about the efficacy of vaginal rejuvenation. I just think that Americans resort to all kinds of elective surgery far too easily. But, by all means, if your vag needs freshening up, please don’t let me stand between you and a pair of plumper lips.
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.
