Q:
I’m a virgin. I’ve been dating the same guy for seven months and he is a virgin too. My mom always told me having sex before marriage was okay as long as I love the person. We say I love you but I don’t really know if I truly love him. I plan on going across country for college next year. He plans on staying here to work at his family’s business. I’ve decided I don’t want to go to college still a virgin. Most of my friends have already had sex and I always feel like I’m missing out on something when they talk about it. I think I want to give my boyfriend my virginity for his birthday. Is there anything I should know to prepare? Do you have any pointers for first timers?
-Ready (she/her)
A:
Dear Ready,
Let me first start off by saying that in 2022 we don’t use phrases like lose my virginity or give my virginity anymore. We say, have sex for the first time or first shared sexual experience because virginity is a construct that shapes the way we think about sex, our bodies, and our identities for the rest of our lives.
From your message, it sounds like this construct has already informed some of your thinking around sex, as you see giving your virginity as a gift to give up and something your boyfriend gets, as in gets some. So let’s take a step back and consider, dear Ready: what does sex mean to you? Being that you haven’t had it yet, I realize this might be hard. But I implore you to think long and hard about what place you want sex to have in your life, both now and into the future.
Will sex be something you get, give up, withhold, or use as a reward or punishment? What is its purpose in your life—pleasure, power, or both? Is it something you perceive as scary and constricting, or exciting and exhilarating? Is it evil or divine, dirty or sacred? What feelings do you hope to feel after your first foray, and after a sexual experience overall?
The best lovers know that sex isn’t some act—a thing you do—but rather, it’s a place you go. I often ask people to consider partnered sex as an erotic exploratory journey you get to go on with another, where you see and find parts of yourselves that you never knew before. That’s where the fun lies! At the very least, I hope you can reframe sex as a shared experience of mutuality and pleasure, rather than some ideological myth of giving away your v-card.
I know parents and previous generations like to perpetuate the idea that sex is deemed acceptable only if you love someone (or the more antiquated view—only if you’re married), but that’s simply not true! The conflation of sex and love has caused much confusion and many heartaches, Ready. Sex and love are two different things and exist without the other, though they do go quite nicely when paired—just like bread and butter, strawberries and chocolate, ketchup and french fries, or pancakes and syrup.
So when is sex acceptable? When there is enthusiastic consent, you’re safe and responsible, you truly desire to have it and are not being pressured or coerced (by a partner, friends, culture, or otherwise), and when you’re with someone who is respectful of you, your body, your needs, and your pleasure.
First, start an honest conversation with your boyfriend about consent, desires, expectations, birth control, and safety. Then figure out the logistics. Where and when will this happen? What ambiance do you want? And most importantly, do you have a safe word in case you want to stop? I know it might not seem that sexy to talk about it, but trust me, having these conversations beforehand will contribute to higher odds of it being a positive experience.
Next, think of where your own pleasure fits into this equation. If you’re not regularly masturbating and exploring your body, I encourage you to start ASAP. If you are, do you orgasm consistently when you masturbate? There’s no right or wrong answer here, my only point is that we must be intune with our bodies first before we go attempting to play a harmonious duet with another. The big-O is something you do and share together, not some magical gift he springs on the well of your body.
Before jumping into penetrative sex for the first time, have him get you off with his hands or his mouth (if he hasn’t already). When I was in college, I used to wonder why my girlfriends were willing to risk an STI or pregnancy if they weren’t even going to cum. But the truth is, sex doesn’t have to be all about orgasms as the grand finale. Great sex happens often without climax; sex satisfies our needs for sooooo many things such as creativity, connection, intimacy, pleasure, feeling alive, and in your case—curiosity.
And you know what? That’s totally cool and your choice! With your perfectly normal curiosity, you’re well aware of what you want and why you want it, and you’re clearly not using sex to manipulate your boyfriend or the relationship. I’d say that’s pretty solid, Ready. But again, please think more about sex and what meaning you wish to create for it in your life. It might shed more light on other aspects of your internal motivations and desires, and deeper self-awareness can only help you on your journey of becoming a lover extraordinaire.
Now let’s get to the real talk. Your first time likely won’t be fireworks or orgasmic explosions. The best part of it will probably be the tenderness, foreplay and kissing before penetration, the cuddling after you’re done, the shared giggles and intimacy over the awkwardness of it all.
My first time I bled. And it hurt—really badly. I should have used more lube. But I did it again the next day, and the next day. I kept going. I guess you could say it’s kind of like learning how to waterski or ride a bike. You have to really attune your body to what you’re doing in order excel at it. It’s a skill that takes practice, on your own and with your partner(s). Sex for the first time might seem like an event, but remember, this is only the beginning of the process that is the evolution of your sexuality. It’s like opening a door to a magical land that has yet to be discovered and explored. Keep exploring.
And FFS, be sure you both know how to use a condom properly—from how you open the wrapper, to how it’s put on. They are only effective if used properly. Def don’t skimp on the lube—more specifically—a water-based lube. Oil based lubes and even alternatives like coconut oil can break down the integrity of condoms. WATER-BASED LUBE!
Don’t worry about whether or not he thinks your thighs are fat or if he sees that pimple on your bum or what he thinks of the way your pussy looks. He’ll be so excited that his rocket ship is about to blast off into your supernatural V of galactic outer space for the first time, he’s not going to pay attention to whatever it is about your body that makes you insecure. We all have something we’re insecure about—even him—so don’t sweat it.
Finally, be sure you’re relaxed and in a safe comfortable environment. Don’t just go for it. Take your time. Spend a long time kissing and working your way up to that moment. Giggle along the way—it builds intimacy and comfort. When you do finally go for it, breathe deep. Don’t clinch. Relax. Let go.
And remember, sex is like meatloaf. The first time you try it from your school cafeteria, it tastes so god-awful-horrible, you swear off eating meatloaf ever again. You think there’s just no f*kng way something that disgusting could make a come back on your tastebuds. But then you’re visiting a friend’s house for dinner and the main course is grandma’s homemade meatloaf. To be polite, you reluctantly serve yourself a small piece. To your delight and surprise, it is the juiciest most delectable morsel of heaven you’ve ever had on your tongue and you go back for more.
My point is, don’t judge sex forever by the first sexual experience(s) you have. Be open to trying it again with someone new, somewhere new, with different variables. Maybe it’s just the seasoning and the type of meat that needs to change! Be willing and open to thinking about sex in new and different ways. There’s an infinite amount of variation out there in this world, and you’re sure to find at least one varietal where you feel like you can’t seem to get enough.
Love Always,
Mal