Let Us Sex-plain: I want to have multiple orgasms, but I’m not sure how

I get it—being single in the city can be tough, and the ways New Yorkers are having sex these days can be surprising. But whatever your dating conundrum might be, I'm here to help. Consider me (Jillian Anthony, Time Out New York's Senior Things to Do editor) your personal wingwoman, guiding you through dating and doing it in New York in our weekly "Let Us Sex-plain" column. Check out my answers to all your questions online and in the magazine every Wednesday, and submit your own coitus queries below!

Is it normal for a woman to only orgasm through oral sex?
—S, Nassau
Yes, very, and that’s because most women only come through clitoral stimulation. According to a study from the Kinsey Institute, only about a third of women orgasm regularly during penetrative sex. Another third only come during sex with a helping hand, and a final third never come during intercourse—only through manual or oral stimulation. This means that, for most women, dicks are unfortunately not magic sticks. Men and women alike should remember there is no “I” in team—or orgasm. Men should practice being giving lovers, and women should ask for what they need in bed. In my America, no orgasm gets left behind!

In the past, certain men I’ve dated have been able to make me come multiple times, but that’s a rare occurrence with my current boyfriend (though I do always have an orgasm). I’m not sure what to ask him to do that would bring about multiple ones, but I know it’s possible for me. Any advice?
—Jacklyn, Bed-Stuy
Ask and you shall receive! When you want to go for round two (or three, or six—reach for the stars!), let your boyfriend know. Maybe he’s never been with a woman who comes more than once (or voiced that she wants to). Or maybe he’s thinking, well, my job here is done. Either way, he’ll probably be turned on by the fact you’re so turned on. At that point, you just have to tell him what’s working for you and keep on workin’ it together.

A guy I’ve been casually hooking up with just lost his mother. I want to reach out or do something nice, but I wonder if that’s weird since we’ve never done much beyond late-night sex. What’s the right move?
—Eileen, Chelsea
Sex friends can be real friends, too. He’s likely dealing with intense grief right now; definitely don’t add any extra stress to his plate by making demands on his time. A simple text saying, “Hey there. I’m so sorry for your loss and I’m thinking of you and your family,” is about as much as you should offer. If he responds, great, and if he doesn’t, let it go—he’s got more important things to think about.