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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…continue reading…

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Fretting Over My First Time


I’m a 17-year-old virgin. My partner and I tried having sex, but we couldn’t get it in. I went to the doctor for contraception and I asked her why we couldn’t get it in. She said that I needed to relax; how the hell do I relax?! During sex (or trying to) I wasn’t worried. I was a bit daunted by it because I had no sexual experience — none, nada, nothing! Do you have any advice on how I can relax?

Secondly, I’ve never given oral. I want to try everything at least once. In my head I think, “I can totally do this, I’m fine, I’ll just go for it,” but when I was in the situation where I could give him oral, I couldn’t do it. I think at best, I’m worried about the taste. I’m also worried about whether he’ll like it or not, or whether it’ll accidentally brush against my teeth. Do you have any advice on how I might overcome this? Or any advice on giving head?

When I’m not writing this column, I’m teaching workshops about sex and consent. Teaching these workshops to youth has made one thing clear: Teens are getting a lot of confusing and inaccurate information about sex. Most problematically, movies, porn, and music rarely portray anyone talking to each other about the sex they’re having.

So, you’re taking great first steps towards your first time by including visiting your doctor, discussing contraception (Please also discuss STI/STD protection with your doctor and partner), voicing your worries, and seeking reliable information.

Here’s my best advice for all your questions: Talk with your partner. This sounds simple, but it works wonders and is No. 1 on the list of things-I-wish-I’d-done-differently-my-first-time amongst adults…continue reading…