Share Post

When I was seventeen, I decided I was ready to lose it – and by lose it, I mean pop my cherry, park the pink Porsche, go all the way. The fact is, I was sick and tired of being a virgin. My mindset was – just get it over with, so you can have fun. My V-card was beginning to weigh on me like wearing a down-coat during a Manhattan summer.

I should preface this story that I was going through a particularly rebellious period in my life. I was angry at every one, especially my parents, and felt all alone. It got so bad that my parents actually pulled me out of boarding school, during the spring trimester of my junior year. There I was. Angry. No friends. And stuck at home.

In order for me to complete my schoolwork in time to return for my senior year, I started seeing a tutor. This tutor, let’s call her Mrs. Handle, liked to know everyone’s business. She poked and prodded at me endlessly to get the full scoop on why I had been pulled out of school. When I didn’t acquiesce, she turned her laser focus to my love life. That’s when she brought up her other student, Devon.

Oh, yes. I knew Devon, but I hadn’t seen him since high school started. I had gone on a double date with him, when I was 13 and he was 12. I thought he was really cute, with his relaxed t-shirts, easy smile, and rich kid sex appeal. We went to see Mission Impossible, starring Tom Cruise, at the local movie theater – the kind of cinema that has one theater and shows one movie at a time. We sat in the back, under the mezzanine. He asked if he could taste my lipgloss and leaned in for the big kiss. Then, very swiftly, his hands were between my legs and I was being introduced to a whole new level of “making out.”

It hurt like hell and he had no idea what he was doing, but I was never the kind of girl to say no.

So, yes, Mrs. Handle, I knew who Devon was.

We were set up again and started to hang out regularly. He had recently suffered from a family tragedy regarding his older brother, and I got the feeling he liked the distraction. We spent a lot of time in his room, making out. He grew up in a huge, hidden mansion, so there was never any risk of being caught.

I saw my opportunity. My last place of revenge against my parents. If I can’t do anything else, I thought, at least I can screw whoever I want to. And anyway, he was experienced. Devon had definitely been around the block and back.

So, I mentioned it to him. No, I promised him.

”Next time, let’s have sex.”

As soon as the words were out of my mouth, I regretted it. I mean, I had just started to be able to have oral sex without gagging. But there was no turning back. And he wasn’t exactly disappointed that I had mentioned the big S.E.X. He was sixteen. This was exactly what he was hoping for.

So, there we were, on a Wednesday night, making out, as usually. But this time, he pulled me onto his bed and grabbed a condom from his dresser.

“Oh, god, this is it,” I thought. “I’m not ready. I’m nervous. I really don’t want to do this. Why did I mention it?”

But I didn’t share any of my regret with Devon. He was not caring. He was not concerned. In fact, he made me be on top – a position, I think is totally unfair, since I was the inexperienced one. He kept falling out of me. I didn’t know what I was doing. I didn’t know where to put my hands. I won’t lie. It was awkward and uncomfortable and completely without affection.

Then came the knock at the door.

Bang, bang, bang.

We both froze.

“Honey? Do you guys want some snacks? Some popcorn?”

It was Devon’s mom.

“No, Mom, we’re okay!”

Are you kidding me? Did his mom just knock on the door as I am losing my virginity?

Yes. Yes, she did. And after that, it was over very quickly. He was finished. Condom came off. I got dressed. I left. We never spoke again. I convinced myself it was fine. I steeled myself against my heart, thinking that I got what I needed from him.

Looking back on it, many years later, I don’t regret it…really, because I have gone onto discover how amazing sex can be when you love the person you are with. But I do wish I had stood up for my doubts and fears the first go around. At the time, I felt like I couldn’t go back because it had been my idea. Because Devon and I did not have a close relationship, I didn’t feel comfortable telling him any of my concerns. Honestly, it has taken me over ten years to be able to do this. I wish I could have seized the opportunity to talk about both of our broken hearts. I wish I could have not only shared my fears, but asked him about his. I wish I could have been strong enough then to stand up for myself. I wish I had been able to say no. No, not now – not like this. I’m not ready and I’m scared.

But I didn’t. And that’s life.