Dear Di,
I’ve recently started dating someone, and I really want to have sex, but I’m worried that I’m going to embarrass myself because I’m a virgin and I don’t really know what to do. Do you have any tips on how virgins can knock it out of the park on their first time up to bat?
—Raunch Rookie
Dear RR,
First of all, virginity is a social construct that has no biological significance. I’m not trying to diminish your concerns about never having had sex before, I just want to be clear that there’s a lot of hullabaloo around virginity that isn’t based on facts.
The concept of virginity is based on the idea that, in a heterosexual couple, a woman “loses” her virginity when a man puts his penis inside her vagina, thus perforating the hymen. However, the hymen doesn’t actually fully cover the vagina; instead, it is a partial layer around the vagina. In some cases, a woman does have a hymen that fully covers her vagina—this condition is known as an imperforate hymen. If you’ve ever gotten your period, you don’t have this type of hymen.
Bleeding is common for female first-timers because of tears of the hymen, but it’s not necessary to “lose your virginity.” The idea of virginity is a pretty loaded concept that puts a lot of pressure on women to be “pure,” to the extent that women have virginity tests conducted on them and go through costly “hymen restoration” surgeries (which, I should note, are a complete scam). From now on I will refrain from using the term virginity, and say having sex for the first time.
This brings me to my next point—have you engaged in any other forms of sexual activity? Too often we consider sex to be solely penis-vagina sexy times, when there are so many other sexy times people have that I wouldn’t want you to miss out on.
I subscribe to the Jessica Valenti school of thought in her book, The Purity Myth, that you have sex for the first time in your life when you orgasm. So whether it’s the first penis-vagina penetration, first oral sex experience, first fingering, or the first time you saw Titanic, each person’s first time is going to be different.
Now to finally get to your question, what can you do to up your confidence if you’ve never had sex before? Masturbate, masturbate, masturbate. You won’t be able to tell someone how to touch you if you don’t really know what you want. I recommend purchasing a vibrator (re-chargeable if you can, it will save you money over battery-operated toys in the long run), and sink into your favourite sex fantasy.
For men, you can skip the pricey toys, and stick to lube and your own two hands to reach ecstasy. Don’t be afraid to dive into porn-watching to familiarize yourself with different sex positions, but be aware that porn can be highly misleading.
Finally, when you’re getting it on with that special someone, communicate. Check in with them when you’re getting hot and heavy, ask them what they like, and don’t worry if there are a few awkward moments. Most people get pretty excited when someone wants to get naked with them, and if your partner isn’t excited, they aren’t worth your time!
Love, Di
Horny Homework: Oral Exam
Have your partner lie on their back and kiss them until you get between their legs and are going down on them. Use two fingers to penetrate them in their vagina or anus, and the other to touch their chest.
Dishing with Di: Maybe you’re born with it, maybe he ejaculated into your hair
The Ancient Greeks have contributed enormously to Western civilization, but one of their weirder ideas was why a long head of hair has traditionally been considered sexually attractive on women. According to Hippocrates, “hair was a product of the congealing of sexual fluids such as semen.” He believed that during sex semen would travel all the way from the penis up a woman’s body and into her hair. With the absurd costs of women’s hair products, I wonder if Hippocrates ever figured out if semen was a decent moisturizer? Maybe with a little avocado and honey?
