Stoya On Virginity Anxiety

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We love chatting with Stoya — writer, thinker, on-screen-sex haver — about all manner of sexual, sensual, and feminist topics. In fact, we had so much fun talking with her, we asked her to write a monthly sex and relationship advice column. Have a burning question? Send any and all queries to stoya@refinery29.com. No dick pics, please.
I'm 24 and a virgin. I've recently (very recently) started dating one of my best friends whom I've known (and been half in love with) for five years. It's everything I hoped dating my best friend would be, but I have a problem: He doesn't know I'm a virgin. I grew up in a very religious household and was taught to never have sex before marriage. Although I don't believe in that anymore, the older I got, the more protective of my virginity I became — so it never happened for me.
My friends assume I've had sex. I started out thinking it wasn't any of their business, so I never admitted to being a virgin. I know J. [the guy I'm dating] doesn't think I'm a virgin — and we've come to a point in our relationship that I know he's expecting it soon. We've taken it slow because of our friendship, and although I do want to have sex with him, I'm not sure I'm ready (I'm so nervous I'll be awful at it) and I don't know how to tell him or how he'll react. He's said before that he hates having sex with virgins. PLEASE HELP! — H
Having sex for the first time can be a big, expectation-heavy deal for a lot of people. One thing you didn’t talk about was whether the sex and the relationship are linked for you. If your desire to have sex with J. is in any way dependent on the condition that the two of you have a significant romantic relationship, it is extra important that you two have a serious conversation and make sure you’re on the same page. I’d hate to see either of your feelings get hurt because one of you is expecting more than the other; plus, this type of discussion is generally a good thing to have in any dating-type of relationship.
Have this conversation when you can both focus and carefully listen to each other. Talk about your feelings and what you think you want out of the relationship you’re having. Make sure to ask him about his feelings and expectations as well. Define what things like “dating” or “boyfriend” mean to each of you. Once you’ve covered that, start talking about sex. This is where I strongly recommend you tell him you haven’t had sex before. You should also discuss things like what, if any, sexual activities you have engaged in (masturbation, oral sex, etc.) and talk about safer sex practices.
If he’s really into you, there’s a pretty decent chance he’ll be willing to be your first sexual partner. He might not be willing, though — so you should be prepared for that possibility.
There’s one more thing you should prepare yourself for: The first time you have sex is probably going to suck. It might hurt a little bit, it might hurt a whole lot, and it is definitely going to be awkward. I’ve had a ton of sex and it is still awkward pretty regularly. "Awkward" doesn’t mean you’re bad at sex or have failed; it means you’re a human being mashing your body together with one or more other human beings — "awkward" is just part of it.
Set your expectations for your first time (or twenty times) as low as possible, and remember that the only way to get better at something is to practice.
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Hello, my question is: Why does it burn after I have sex with my boyfriend? — A
Call a gynecologist right now and schedule an appointment. Private physician, Planned Parenthood, free clinic, I don’t care which one. Just make an appointment with a specialist.
Now, while you’re waiting for your scheduled doctor visit, get a hand mirror, a flashlight, and an anatomical chart of the female genital area. Type “female genitalia diagram” into Google, and you’ll find plenty.
Put the mirror on the floor. Take all your clothes off. Squat over the mirror. Shine that flashlight into your crotch and start familiarizing yourself with your parts. Learn what the damn names of them are, so that when you’re trying to tell your doctor what burns, you can be a little more specific than “it.”

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