Get naked

Q I’m seeking help with a very important matter—the big O. I am a 26-year-old straight female who very much enjoys sex. I have experienced sex with men whom I feel deeply for, as well as a few emotionless flings along the way. Although my experiences have been varied, there is one thing they all have in common: They are completely devoid of my orgasm. During the act, I reach a plateau level of pleasure and remain on that level throughout the process, which usually ends when my partner comes. I have tried masturbation, but can barely achieve arousal through it. Can you please help? I’ve been with my boyfriend for about a year now, and I love him and am passionately attracted to him, but we’re both extremely frustrated by my seeming inability to achieve orgasm. He pleasures me with his hand and his penis, but he’s not a big fan of giving oral sex and has yet to go down on me. Please give me advice!

A Ah, the old “I can’t achieve orgasm” letter—we meet again. I thought I had finished you off for good years ago, when the last female in the world finally realized that this is a common problem for women who have cunnilingus-phobic boyfriends. But no, you’ve managed to regroup and fight your way back into the column. Okay, well, let me dispatch you forthwith: Sometimes the lady parts don’t react well to mere pleasuring with the hand or the penis. The lady parts get all sad and shut down if a tongue doesn’t pay a visit. I’d be interested to know if you’ve ever had a guy go down on you. If not, you’ve got to figure out a way to get your boyfriend to give cunnilingus another go—tell him he could be the first person to give you an orgasm, and provide him with a big stuffed panda should he achieve that goal. I know it’s frustrating not to be able to get off easily, but don’t get discouraged. Many women are in the same situation. Just keep plugging away in various modes (tongue, penis, fingers, stuffed panda—hey, it’s worth a shot) and eventually you’ll get there.

Q I’m a 28-year-old…well, guy is all I got. It’s a growing concern of mine that I’m this age and have yet to be with a woman. As a child I had many crushes on different girls, though I was the fat kid back then. Growing up that way made dating very difficult. I’ve only gone down on a girl once before, but haven’t had sex with one yet. Further complicating matters is that I am open-minded enough to know that I can get a gay guy to help me get off, with no strings attached. I’ve been blown and have fucked a guy, but never felt anything for them. I think of myself as straight, but I’m being gay. It’s a riddle I can’t figure out. Am I what I want mentally or am I what I get physically?

A It’s actually not that complicated a riddle: You’re a horny-as-fuck straight dude and you’re doing what you have to to get some. The problem is that you should be focusing your time and energy on getting past your “fat kid” emotional damage and landing yourself a woman. In fact, I suspect that you’ve created this whole false “Am I gay or am I straight?” riddle simply because it’s far more scary to face the possibility of real, meaningful rejection again. If guys are into you, there’s no reason why women wouldn’t be also. I sense a bit of self-defeatism here: The past is the past, and you’ve got to treat every new interaction with a woman as a unique opportunity filled with promise. Now stop fucking asses you’re not really into and start using your strengths—i.e., your sensitivity and emotional vulnerability—to wow the ladies.

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.