The Adult’s Guide To Losing Your Virginity [NSFW]

Not all of us lose our virginities at age 16 in the back of an old Camry. If you’re still a virgin later in life, it can feel like you’re the last person on earth who hasn’t had sex, but you aren’t alone. Whether you’re waiting for your wedding or just haven’t found the right person, here’s what you should know about losing your virginity as an adult.

Illustration by Tina Mailhot-Roberge

What To Expect

You probably know the basics of where everything goes, but let’s start by talking about what you should expect before, during and after losing your virginity.

Before

First things first: what does virginity mean to you? Most people think that p-in-v intercourse is what defines losing one’s virginity, but that really shouldn’t be the default. Intercourse might not be a part of your desired repertoire, or there may be other acts that have more meaning to you. It’s really up to each of us to decide what act constitutes losing our virginity. Aside from the logistics, there’s also the emotional weight that you assign to your virginity. Would you like to lose your virginity with someone you care about? Are you saving it for marriage?

On that note, a lot of older virgins struggle with whether or not to lower their standards (in one way or another) to get it over with. Being clear on what your virginity actually means to you may help you stick to your guns a bit more. Being self-conscious about your virginity status is understandable, but do you really want to remember this experience as “that time when I got desperate and threw my standards out the door”?

One of the biggest questions that comes up for later-in-life virgins is whether or not to tell a potential first partner about your virginity status. My advice tends to be yes: your virginity isn’t anything to be ashamed of, so you don’t need to hide it. Virginity means different things to different people, so you should allow your partner to decide whether or not they feel comfortable being the one to take yours.

You’ll also need to figure out how you’re going to protect yourself from sexually transmitted infections and (if there are male and female parts involved) pregnancy. Have a conversation with your partner about their STI status and what sorts of barriers to use. Do this before you’re naked and horny.

You’re probably going to be a big bundle of nerves before losing your virginity. That’s OK! No need to force yourself to act nonchalant if it feels like there’s a colony of butterflies setting up shop in your stomach. Let yourself feel whatever you need to feel before, during, and afterwards.

During

Let me be real with you: your first time is probably going to be short (if there’s a penis involved), a little awkward, and not particularly fantastic. It will feel like there are an awful lot of limbs involved and no good place to put any of them. It takes time and practice to learn how to have great sex. You’ll get there eventually, but not your first time — and that’s OK! Try focusing on the acts you’ve already done and feel comfortable with to bolster your confidence.

If there are lady parts and penetration involved, your first time may also be somewhat painful and bloody. Most people think that the hymen is responsible for these unfortunate side effects, but that’s not necessarily the case. The oft-misunderstood hymen doesn’t block off her vaginal canal, and doesn’t “pop” during sex. It’s a permeable membrane that likely already has a number of perforations in it. If she does experience pain, it’s probably because the sensitive tissues of her vaginal canal aren’t used to being penetrated in this way. Bleeding can come from the hymen, but it’s just as likely to originate from the tissues of her vagina, which again, aren’t used to this kind of intrusion.

After

Be prepared for clean-up. As mentioned above, there may be some blood involved. There may also be lots of bodily fluids that are rapidly sliding their way out of your orifices. Have a box of Kleenex or a towel nearby.

If you’re a lady, be sure to pee afterwards! Bacteria can get pushed into your urethra during any sort of sexual contact. You do not want to celebrate losing your virginity with a nasty UTI.

My Advice To You

When my clients talk about losing their virginity, the phrase “I wish I had know that beforehand” comes up over and over. Here are some tips to for avoiding many of the common virginity-losing pitfalls:

• Talk about your expectations beforehand. Simply talking it out can help decrease your nerves and set more realistic expectations. Your partner might tell you that they just want to get the first time over with and focus on making the second time more fun. Or maybe you both agree to take your time and make it special.
• It doesn’t have to be your wedding night. If you’ve decided to wait until marriage, I highly recommend doing it the day after your wedding. You’re going to be so exhausted from the festivities that you’re going to be dangerously close to passing out the second that your head hits the pillow. Sure, you could force yourself to have sex, but who wants that as their first-time memory?
• Be sober. Navigating your first time takes a little effort, so you want to have all your wits about you. Being drunk or high will make it more likely that you’ll experience pain and less likely that you’ll enjoy yourself (or even remember the experience at all!). A glass of wine is fine to calm your nerves, but try not to get too tipsy.
• Spend plenty of time on foreplay. Some people are so eager to get to “the main event” that they forget that the “foreplay” is more than half the fun. Plus, it will help you both relax and feel more excited about sharing this experience.
• Use your fingers to help guide your penis into her vagina. This practical tip is for you straight dudes out there. The vagina is a little harder to locate than you might think, especially if you’re eager and nervous. If you let your fingers do the finding, you’ll avoid awkwardly jabbing at her with your penis.
• Use lube. Lube can help decrease the pain and make things feel so much better for both of you, especially that first time.
• Keep it simple. Remember, your expectations are supposed to be low, so there’s no need to try to impress your partner with a ton of crazy gymnastics. Stick with simple positions that will feel comfortable and allow for some emotional connection (if you want that).
• Don’t pressure yourself or your partner to orgasm. There are enough things to worry about without adding orgasm to the mix. Focus on enjoying the sensations instead.
• Don’t worry if you don’t enjoy it. Lots of people didn’t particularly like sex the first time they had it. Having a crappy first time is not a harbinger of sexual doom. Think of it as an excuse to try again really soon.

Have fun, and welcome to the wonderful world of being a sexually active adult!