What if I’m bad at it?

This question haunted me. I was a perfectionist in school and a pretty responsible adult, so the thought of letting someone down in bed was utterly humiliating. It’s also the sort of thing that gets worse in your mind with each passing year that you don’t have sex, and unfortunately, the humiliation manifested itself in a real way for me in the form of a quasi-breakup. I happened to fall for a guy in college who now I credit with destroying my self-confidence and rendering me incapable of intimacy with anyone for seven years. At the time, we were ambiguously inseparable – the type of couple that people were always wondering about. After over a year of back-and-forth (and other crushes in-between), I asked him what we were doing, and he told me that he didn’t want to date a friend. Unsatisfied with the answer, I asked for a better one, and he said that he wanted to be with someone who was more “experienced.”

Because of that shithead word and that shithead person, I missed out on fun sex in my early twenties. I let the idea of my inferiority – based on one person’s completely unfounded inference, by the way – control my happiness for seven years. The truth is, I was bad at it at first. Everyone is. And being an older virgin, you’re likely to be with someone who is more experienced when it actually happens.

Assholes like that one I mentioned usually reveal themselves if you trust yourself and consider the signs, and they’re definitely not worth sleeping with. There was a reason we hadn’t slept together when the question came up, and it wasn’t because of my inexperience — it was because of his selfishness. Being a virgin is a good thing to a good partner. Whoever you’ve decided to sleep with first should consider it an honor, especially because they’ll have a hand (and many other parts) in shaping your sexual future, too.

Communication is also incredibly crucial. If you’re feeling insecure, it’s OK to say something. If your partner’s mood is shot by your honesty, then fuck them. (But don’t actually fuck them, if you know what I mean.) More than likely, they might take the opportunity to build you up, to tell you why they think you are sexy, and you should listen to them, because they’ll be telling the truth. If you’re not sure about how to do something, ask. Asking the question means getting the answer, and getting the answer means learning something.


What’s it like to lose it when you’re 27?

At 27, high school, college and post-college were behind me. I was at the end of my second real-world job. I had experienced all my friends’ hookups and relationships as a third wheel, and I had consumed more romantic comedies than I realized. So I had arrived at an unholy trinity of high, low and no expectations. No expectations, because I hadn’t experienced sex before, and it had been nine years since I had kissed someone. Low expectations because I had gathered that many guys were untrustworthy in life and selfish in bed and I assumed I was going to be horrible at it. And high expectations because 27 years is more time than most people get to build them up.

I felt an anticipatory, subconscious calm the night it happened. I was staying at my parents’ house, having just returned from a trip, and I drove a couple hours to meet up with him. I wore something that made me feel confident, and we went to dinner. I don’t remember what we talked about, but I know I felt relaxed. After paying for my meal, he asked me if I’d like to come back to his apartment for a drink.

The walk was short, and I was smiling nervously the whole time. The feeling of being next to someone in public and knowing they wanted you was thrilling, energizing and completely foreign to me. For that night he was mine and I was his and no one could get in our way.

We drank a lot, probably more than we needed to, but I know it helped ease my anxiety. Even as we made out on the couch and transitioned to his bed, I knew I’d be nervous just to show my body to someone else and to see someone else’s body for the first time. I think my age and the alcohol settled whatever insecurities I had about my own body, but I hadn’t seen many naked male bodies before, and I definitely hadn’t seen one that wanted to have sex with me.

Somewhere in the process, I told him I hadn’t had sex before. From my drunk standpoint, he seemed fine with it, because we definitely kept doing it. I followed his lead the whole time, and I was as open-minded as he was patient – an example being that I learned the “no teeth” rule pretty quickly.

I feel comfortable saying that he slept decently that night and I did not. I can’t imagine how I would have been able to fall asleep; being an only child, I struggled to fall asleep at sleepovers and took my sweet time getting used to having roommates in college. Moreover, I had never slept naked by myself, let alone with another person naked next to me.

We woke up with our heads throbbing – in his case, in more ways than one. (I’ll get to that later.) Hungover, I put on my dress and shuffled to the bathroom, only to realize that I had left a trail of blood droplets behind me.

I knew that sex could be painful the first time, and that I might even bleed, but I still wasn’t mentally prepared for the blood. I was mortified – though I wasn’t hurt, and what happened wasn’t bad or wrong. It just meant I was (a) a human with feelings who had (b) just lost her virginity. I couldn’t help feeling gross, though. I felt the same way I felt when I got hit in the face with a soccer ball in high school and my nose started gushing. I just didn’t want anyone to look at me.

Just like my high school pals – who actually wanted to look at my face so they could help me stop the bleeding – he didn’t care. I believe his exact words were, “I know how bodies work,” which was sweet music to my ears at this critical, impressionable moment. He didn’t find me gross.

I grabbed some paper towels from his kitchen, and he followed with cleaning supplies and just let me do the carpet-blotting I wanted to do.

After that, I showered – blood still spattered at the hem of my dress – and then we said our goodbyes, and he very honestly admitted, “I really need to jack off.” Of course. He was a gentleman the whole night, but he still had needs. So I left him to it and went home.


Putting it out there

You’ll have to learn just like me 
And that’s the hardest way
Ooh la la, ooh la la la la yeah
I wish that I knew what I know now 
When I was younger
–- "Ooh La La," Faces

I lost my virginity at age 27, after I quit my job, between international trips and before I moved across the country. I had opportunities to have sex before then, but that moment in time when it actually happened made the most sense. The guy I slept with was not someone I loved — though I thought I did later, because the thing that happens in movies where you get attached to the first person you sleep with does happen in real life — nor was he someone I’d known my whole life. I always thought those two things needed to be true, but I’m so glad they weren’t. He was a good guy, though, and I’m grateful to him, especially because he didn’t freak out when I dripped blood all over his carpeting. He just said, “I know how anatomy works!” and got me some paper towels and let me do the embarrassed cleaning I wanted to do.

The experience of losing my virginity was both the biggest deal in the world and the smallest deal imaginable. I felt a sense of profound relief, because I no longer had to fake basic knowledge about sex in conversation, and because I had solved the mystery for myself. And yet I felt sick, because sex hurts the first few times (see: blood in previous paragraph) and I didn’t know how to handle being nearly 30 and having feelings of teenage affection for someone. And I was hungover.

In the months after having sex, I began to talk about it, and most conversations teetered around the same empty congratulatory statements — from people I knew and loved. They, too, were relieved, but in this disappointing, patronizing way. I had always struggled to converse with people about sex, yet even after I had it, I still wasn’t getting what I wanted out of the having-sex world. But I also learned that a couple of my friends were in the same boat, similarly hesitant to talk about it because of how lonely and mysterious the older-virgin existence is to everyone else.

This site is for those of us who found — or still find — ourselves virgins much later than we ever intended. It’s for those of us who are just as scared about our futures as we are curious. It’s for fifteen-year-old me. It’s for fifteen-year-old you.

But this site is also for them, the family members, friends, would-be lovers and curious strangers who learn this thing about us and either don’t know how to respond to it or don’t give us what we need. Because we need you, just not how you think we do. I can’t claim official expertise or a degree in the subject, but I can tell you that I’ve been there, and I’d like to be there for you.