The V-Spot: Like a Virgin

Dear Yana, I’m a 19-year-old girl who has never had sex. I want to sleep with my boyfriend, 23. He’s had sex before, but doesn’t know I’m a virgin. I don’t really want him to know I’m a virgin, but I know I’ll probably have to tell him. The only reason I haven’t told him is because everyone kind of assumes I’m not a virgin since everyone says I’m pretty. We’ve done other things, but never gone all the way. I’m excited about having sex for the first time, but I’m worried about it being painful. Do you have any advice for how to make it more pleasurable? Are there any lubes or positions that would work best?

— Looking to Lose It

Before you unlock the chastity belt, let’s untie some of these knots you’ve got your virginity all twisted in!

Virginity holds a lot of differing, complex cultural values that, historically, have little to do with enjoying sex. The “value” associated with women’s virginity has been created mostly by people and systems not run by women — men, religion, family, and pop media — to control the bodies of (typically) young women. To some people, Virginity with a capital “V” is a real Big and Very Specific Deal.

But here’s another way to consider your virginity: It’s just some made up bullshit. This isn’t to say that First Times can’t be special and celebrated! But the common conception of what it is to lose your Virginity-Proper needs to be expanded.

Now, for many people, “losing your virginity” is defined as the first experience of vaginal penetration with a penis. If I only slept with women for my entire life, would that make me a forever-virgin? I don’t think so.

I scoff, but this restrictive P-in-V concept of virginity is real and its loopholes are made from people twisting themselves to fit into its tiny, identity-erasing boxes. For example, teens who take virginity pledges as part of conservative abstinence-only education programs are more likely to have anal sex in order to avoid having “real” sex before marriage, according to Sloan Caldwell, 2015, Let’s Talk About Sex: The Failure of Abstinence-Only Policies in America’s Public Schools). Anal is a sexual experience that requires way more skill and comprehensive sex education than an abstinence-only program will ever provide.

This misguided conceptualization of virginity can also look like someone’s physical “prettiness” being equated with their “virginity,” a word that holds synonyms like “chastity,” “honor,” “purity,” and “innocence.”

Well, LtoL, you can still be honorable and pretty and not be a P-in-V virgin. You can be exactly who you are and have a whole variety of sexual experiences that you and your partners get to decide are a Big Deal or not. This is your sex life and your body.

To make this experience more pleasurable and less painful, talk to your boyfriend. If you want to tell him about your lack of experience with P-in-V penetration, you can, and if you don’t want to you also don’t have to. The nice thing about taking virginity off its fool’s gold pedestal is that no one defines it anymore except for you. I will say, it is valuable to share your story, desires, and worries with a partner with whom you’re going to share a First Time. My rule of First Times is, if you can’t talk about it with the person, you shouldn’t do it with them.

Lube is a great tool to have in your sex box and I recommend a water-based lube without glycerin or parabens such as Sliquid Sea. You can read more of my advice about lube and the ol’ V-card in my past column “Something Borrowed, Something Lubed.”

Positions that keep you in control of depth, speed, and angle, like being on top of him facing him, is a good idea for all first time penetration acts because it keeps you in charge in case something feels ouchy. If you go slow, take lots of time to warm up your body and mind, and use plenty of lube, any pain will likely be reduced and/or fleeting.

Most importantly, define your sex life for yourself: You’re experiencing new things with your boyfriend, not losing or giving away anything to him as a token of your value.

Yana Tallon-Hicks is a pleasure-positive sex writer and educator living in the Pioneer Valley. She has a website bursting with sex advice, resources, and workshops at

Yana Tallon-Hicks

Author: Yana Tallon-Hicks

Share This Post On

Sign up for our daily newsletter!

You don't want to be left out, do you?

Sign up!

You have Successfully Subscribed!