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Illustration: Alex Citrin

Let Us Sex-plain: I fantasize about my girlfriend’s sister

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York

Written by
Jillian Anthony

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 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!

I’ve made it very clear to my boyfriend from the start that I don’t want children, but I’ve seen him post on social media implying that he does want children. We haven’t been dating for a full year yet, so it feels way too soon to ask outright, but I’m worried that we’re wasting each other’s time if we ultimately want different things. What should I do?

—Becky, Bensonhurst, Brooklyn

First, you need to know that something like 98.4 percent of the things people post on social media mean nothing; for example, definitely don’t use your boyfriend’s post of a video of a parent-kid team doing a silly choreographed dance along with the caption “Me as a parent” inform your assumption of his stance on children. You say you’ve been open about not wanting kids, but you don’t mention your boyfriend’s reaction or opinion. So far he’s heard your views and chosen to continue your relationship. This could mean not having kids isn’t a deal breaker for him, or he’s still figuring that part out, or he just hasn’t seriously thought about it yet. But you are thinking about it, and you’re considering building a future with this person, so it’s time to talk about the subject, even if you haven’t been dating so long. Open the discussion now and see if you’re on different pages rather than figure it out another year later. Start slow—“I’ve told you before that I’m not interested in having kids. I’m wondering, do you see yourself with children someday?”—and have an honest conversation from there.

Is it okay to fantasize about your girlfriend’s sister?

—Tonya, Ridgewood, Queens

A fantasy is just that. It exists within your own mind and for your own pleasure, and it affects no one outside your noggin. So, fantasize away! Give yourself permission to enjoy your own sexy thoughts, whatever they may be, without self-judgment. Just make sure they don’t cross over into a real-world desire.

I lost my virginity to a guy I really like, but I don’t want to tell him he’s my first. I’m also scared that he’ll notice that I’m inexperienced. We’re not yet dating, but we have a solid connection, and I don’t want sex to ruin things. How should I approach this relationship?

—Sara, Astoria

If you don’t want him to know your first time was with him, don’t tell him! You don’t owe him or anyone that knowledge. He may notice you’re inexperienced, but hey, we’ve all been there! Practice makes perfect, so if you like him and feel comfortable, just let him take the lead for now, and have more sex! As far as ruining things, you say you really like this guy, and you’re now sleeping with him, so you two aren’t simply pals. Keep getting to know him, and gain a sense of whether this will develop into something more (or not). But for now, relax and have fun!

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