I’m Not Sure When I Lost My Virginity

It was a kind of confusing two day ordeal

I can tell you with certainty that I lost my virginity at sixteen. I can also tell you that it happened early September.

But if you ask me to pin down the exact date, that gets tricky. And my answer has changed over the years.

That’s because losing my virginity was less of a wham bam event, and more of a two-day process.

Day One: My Bedroom

The first time I had sex, it wasn’t for what most people would call the right reasons.

My first boyfriend left me because he thought he might have a chance at dating my best friend. He didn’t want to miss out on the opportunity by being tied down to me.

That hurt, but I wasn’t ready to let him go. Even after what he had done to me, I still felt madly in love.

I thought sex could win him back. Maybe, if he got a taste of it, he’d know what he’s missing and he’d be mine again.

The girl he left me for was still a virgin, too. Fucking him would give me a competitive advantage.

But that wasn’t the only reason I did it. I was also eager to get this whole sex thing over and done with.

I was sixteen and just a few months away from turning seventeen, and I believed the kind of dumb shit sixteen year olds believe.

I felt like the clock was ticking. If I didn’t lose my virginity soon, it would become a big deal. I would no longer be Emma - I’d just be The Virgin.

I had a willing accomplice, so why not just do it?

We hung out. We got high in the middle of the day. And I told him I might be ready to have sex.

He was down, so I took him to my bedroom.

But as we laid on my bed, my confidence melted away.

I was no longer so sure I wanted to go through with it.

I lay there for a long time trying to decide if I really was ready. I have no idea how long it took me to make up my mind, but it felt like an hour.

And I really do mean I laid there. We didn’t kiss. We didn’t touch. We didn’t hug or snuggle. We just laid next to each other while he periodically asked “So, are we going to do this?”

It’s obvious to me now why I was so hesitant. I wanted the first time I had sex to feel a bit special, and this wasn’t special. I wasn’t expecting a bed strewn with rose petals and the perfect romance or anything like that. But I did hope for more than an impatient fifteen year old sighing next to me.

But worse than that, I wasn’t even horny. And it was ridiculously easy to get me horny at that age. A cute stranger brushing against me could do it. Some affectionate touching would have have gotten me there in no time.

Instead, it felt like I was rubber stamping the decision - just giving my formal approval to having sex.

Eventually, he said “Are we going to do this or should I just go home?” I figured it was now or never, so I took a deep breath, said okay and took off my pants and underwear.

He took his off too, pulled on a condom, climbed on top of me wordlessly, and tried to penetrate me.

“Tried” is the keyword here. No matter how often he pushed his dick against my pussy, it just wouldn’t go in.

Of course, I was as dry as can be. What we did leading up to this moment was the exact opposite of foreplay. It was, at best, forelay, and it did not prepare my body for sex.

I’m also pretty sure he wasn’t fully erect. I mean, how could he be? I’m honestly surprised he even managed to get a chubby after spending such a long time being bored and annoyed.

Our attempt to fuck ended as unceremoniously as it began. He got frustrated, said he didn’t know why it wasn’t working, and then said “I should just go.”

And he did. He put his pants back on and left.

And I was… Well, I was confused.

Did I lose my virginity? Did I just try and fail to lose it? Is attempting to do it enough? Does dick-on-vag contact count even if he didn’t actually enter me?

I thought it would be obvious. That I’d just know. Nothing prepared me for how ambiguous giving my virginity could be.

Day Two: His Parents’ Bed

After reading about that whole ordeal, you’re probably crossing your fingers and hoping I just forgot about that guy and moved on with my life.

I’m sorry to say I wasn’t the self-possessed woman I am today. Instead of getting rid of his ass and looking for someone who could treat me right, I went to his place the very next day.

Things went much better that time. For one thing, there was actual physical contact - we made out on the couch for a while.

I was getting aroused - he might have been an asshole, but he was still a really good kisser.

So, we moved to his parents’ bedroom to try this whole sex thing again.

There was no hesitation this time. I wasn’t nervous because I didn’t feel like a virgin anymore. The awkward dick bump I got the day before was enough to make me think of sex as just something I did now, not something I was going to do someday.

We took our pants off, he climbed on me, and this time he managed to penetrate me. He was fully erect. I was wet from the makeout session and the anticipation.

That’s when I discovered that sex wasn’t just something I found fascinating. It’s not just something I was curious about. It was something I really enjoyed.

I wouldn’t call it good sex. Neither of us engaged in any real foreplay. I didn’t have an orgasm. He didn’t say a lot of sweet things to me after we were done. But it was still a good experience overall.

It was comfortable and easy. There was none of the pain or discomfort I had been warned about. It just felt really fucking good.

There were no questions this time. I had full-on penetrative sex. I was no longer a virgin.

Who Knows When I Lost My Virginity (Maybe It Doesn’t Matter)

I used to consider Day One of my two-day attempt at losing my virginity to be the day it happened. I felt like I had ripped my V card into tiny pieces the moment I got a guy to slip on a condom for me.

These days, though, when I try to pinpoint the moment, it’s Day Two that feels like the day I joined the ranks of people who have sex.

It’s when I actually experienced penetration, yes, but it’s also when I got a taste for how good sex could feel.

It also felt more sexual. Day One was more of a formulaic “let’s just get a dick in me” experience. On Day Two I was horny. I really wanted it. I was actually wet, for Christ’s sake.

Still, it’s a bit fuzzy. I can still make a case for Day One. There was no penetration, sure, but it’s the day I decided to try and did. It’s the day I overcame all my nervousness and fear. I took a leap and went for it.

But I’m not sure pinpointing when I lost my virginity really matters all that much.

For one thing, I feel like I did it twice. No, I don’t mean on Day One and Day Two. I mean when I had sex with a woman. That felt like losing my virginity all over again.

And then there are all the other moments that stick out in my memory as grand, important highlights in my sexual history.

My first time masturbating and my first time giving myself an orgasm are formative experiences for me.

My first handjob introduced me to the sometimes decent, sometimes blah, but mostly exciting world of cock.

The first time a partner gave me an orgasm felt like I had crossed some kind of threshold - like, now I knew how amazing sex could be.

The first time someone went down on me was also really fucking eye opening.

When I had an orgasm that was so good I laughed my ass off from the euphoria, it was a revelation that I hadn’t even come close to exploring everything my body can feel.

So, I can’t say with one hundred percent confidence at exactly what moment I lost my virginity. But losing my virginity is also not the only - and maybe not the most important - defining sexual event in my life.

At sixteen, I thought the day I fucked for the first time would be the day that changed everything. But now I know that it’s not the only one. The day I agreed to have sex and tried was a big deal to me. The day I experienced penetrative sex was a big deal, too. I don’t need to decide which one mattered most.

If you liked this article, you should totally check out the Pillow Humpers and Stuffie Fuckers (Grinding, Pillow Porn, and Recreational Humping) episode of my dirty and intimate sex podcast, Pillow Talk With Emma Austin!