Losing ‘It’: A Collection of V-Card Swiping Moments

Doing “it.” Popping your cherry. Giving away your flower. Knocking boots. Losing your v-card. Going all the way. Bumping uglies. Making love. Having sex.

No matter what you call it, we all know how it goes: from the age of about twelve or thirteen, the idea of losing your virginity is something that is ever-present; a blanket of sorts on your mind. Having sex is, at once, a terrifying and enticing idea. When the moment comes around – three, four, ten years later – no matter how much you’ve thought about it, you’re never really ready. Sex often comes with a mess of emotions, confusion, and bodily fluids (ew). Your first time is never what you expect it to be and everyone’s story is different.

I asked twelve girls to recall their first time and share their stories with the world. I told each of them that I wanted their story, in their words. I told them to include as much or as little information as they were comfortable with; whatever they thought was necessary to accurately portray their first time. Here are the stories of their first times having sex.

Splitting Logs

No one knows the real timeline of when I lost my virginity. I’ve blurred the facts to most of my closest friends, not because I regret it or feel ashamed of it, but because I know they wouldn’t understand. I lost my virginity to more or less a forbidden love. I had known him for three years at the time, yet we had never been sexually involved. I had harbored strong feelings for him almost from the start but distance and bad timing kept us apart. We had only ever met a few times in person but talked for hours every single day. I’m not proud to admit that he had a serious girlfriend through most of our friendship. When we kissed for the first time, he still had that girlfriend. The day we took things a step farther was the day they broke up. That’s the fact I don’t tell people. I don’t want the judgmental looks to ruin something this important. I have never regretted losing my virginity to that person, at that time, and at that place. I knew that regardless of whether we ended up together or not, he was the person I wanted to share that experience with.
Now, about the sex itself. Have you ever split logs or chopped firewood? Because that’s paints a good mental image of the pain I experienced. I don’t think I’ve ever felt more like my body was going to split right down the middle. I truly remember thinking “Jesus Christ, I better not get pregnant from this, because if this is what something two inches wide does, I’m NEVER pushing out a baby.” It hurt. Dear God, it hurt. But I made it. We went slow, we talked, he made sure I knew we could stop if it hurt too much. In fact, he felt so bad about hurting me that I was the one who had to convince him to keep going. He was and continues to be my best friend. Regardless of where life takes us, I know I shared that experience with the right person. Oh, and it no longer feels like chopping logs. Practice makes perfect, right?

This One Time at Summer Camp…

I was nineteen. We were working at summer camp. I made him watch Dirty Dancing with me first. He was the first guy I had ever been entirely naked in front of. The condom we used came from a school project he had done. I had absolutely no idea what I was doing. We were in my single bed and all the sheets came off. A lot of laughing, confusion, and silliness occurred before we really figured out how to do it. Afterwards, we shared a bottle of water. I can’t imagine a situation that would have been any more perfect.

The Birth of Venus

I had a plan when it came to losing my virginity. I had just lost a parent and had just started college; every event in my life felt too big for me and seemed to chant “grow up, grow up, grow up.” I didn’t feel like a kid anymore but I had held onto one childhood relic through it all and I wanted it gone. I had this idea that I would cast off my virginity like it was the last thing that still made me a kid and without it I would be some tough-as-nails broad with nothing to lose. I thought I could make myself forget how I wanted it to paint a beautiful picture in my mind and how I wanted to cherish “his” words whoever “he” turned out to be. Who “he” turned out to be was my manager at the college deli where we worked. We entered a weird sort of pseudo-friendship, fooled around, and remained confident that nothing extraordinary would happen between us. But then, a few months in, he said to me that he would never forget me and he wished there was something he could do so that I would never forget him. And as luck would have it, there was. He took care of my hamster one week when I was away, and when I came to get her, it happened. I took off all my clothes by myself and he told me I looked like the Birth of Venus only he couldn’t remember the name and called it “the one where she’s in a half shell.” I kept my eyes on his poster of the teenage mutant ninja turtles eating pizza and it was short. I left with my arms full of hamster cage and a few weeks later he bought me a used copy of my favorite book. My plan didn’t exactly work. I didn’t discard my last girlhood emblem in a fit of “lost everything else syndrome” and I didn’t emerge cynical or without a beautiful picture in my head. My loss became a gain. Suddenly a second hand paperback and a TMNT poster seem like incredible things, and the Birth of Venus makes me laugh. I tried to skirt around a beautiful image and words I’ll always cherish but I remember them that way anyway. Because they were mine.

After Chickening Out

I can remember the night I lost it as clearly as if it were yesterday. It was November and I was sixteen, and we had been talking about “taking the next step” for weeks. We had even tried a few times, but I chickened out and said I wasn’t ready at least twice before. But that night, I felt different. That night, I knew that I wanted him.
I had been at his house for a few hours and we were watching one of those unremarkable made-for-TV movies to fill time before dinner – which his mother was in the kitchen making at the time. I remember catching him looking down at me, just watching me breathe. I looked at him and smiled, but before I said anything, he was kissing me as if he hadn’t in years, like he couldn’t get enough of me. I could feel his fingers in my hair and holding my waist under my shirt, and I was starting to feel warm on the inside. He had started kissing and nipping at my neck when I told him to wait, and he pulled back, looking confused. I pulled out a condom and held it out to him. He asked me if I was sure and I nodded. It wasn’t like any of the last times, I was ready this time. He smiled and began to kiss me again, and I giggled as quietly as I could while he fumbled with the condom, then pulled a blanket over both of us when he was finally ready. The sex itself was short, but the thing that I remembered the most was his eyes. Not once did we break eye contact in the minute or so that he lasted. I don’t even remember feeling anything, discomfort or pleasure, all I remember was what I saw in his eyes, like this was where we both wanted to be.
The rest of the night we stole shy, secretive glances at each other across the table, while we ate the dinner his mom had cooked one room away from where we had sex for the first time!

The Right Feeling

It was the beginning of my junior year in high school and I had been dating my boyfriend at the time for about 6 months. He was my first love and it just felt right. We didn’t plan it in advance or anything, it just happened one day. If I had to explain why I knew I wanted to lose it to him, I wouldn’t be able to, other than ‘it just felt right.’

The Twin Mattress on the Floor

The first time I had sex… it wasn’t joyful or awesome and it felt awful. I mean it got a lot better after that time but I’ll always remember how bad that first time was. But saying it was bad is pretty dang vague so I guess I’ll describe it.
It was in a college dorm room. On a twin bed. That’s already kind of bad enough, but hell, I didn’t know the difference. That’s all I knew. Looking back on it that part alone was shitty. But that’s a very small factor looking back on it. Now that you know it was in a dorm room, here was the rest of what was going on in my mind.
First of all, I couldn’t believe that this really hot guy wanted me at all. He is still one of the most attractive people that I have ever hooked up with. Things were getting pretty hot and heavy and for the first time; I really wanted to have sex. I could tell that my body was saying “heeeell yeah get it in!” I was reluctant since we weren’t actually dating but I gave in because I wanted to know what it was like. I was curious, and now extremely horny.
I was super nervous because no one had ever seen me completely naked (unless you count my parents and that stopped when I was really little and could take care of myself). I was really self-conscious about my body. So combine that with the fact that I was about to hook up with a really hot guy. Nerves out the cazoo.
Well, he had a condom and he knew what he was doing. But I was so tight (nerves, being a virgin) that everything hurt so badly and we could barely have sex at all. I’m still not sure if he ever finished, but when we were done I remember rolling over so that my back was to him and I just started to cry. I thought sex was supposed to be amazing! Instead it hurt so badly, I exposed myself for pretty much nothing, and he might not have even been pleased about it either. And we were on a twin bed, remember? My experiences have been a lot better since then (at least physically), but I’ll always remember those weird emotions, the twin mattress on the floor so that we didn’t wake anyone up, and how I thought sex sucked. I was still curious after that first time, so I tried it again with him and damn, it actually started to feel fan-fucking-tastic.


I was 17 he was 24. He was really experienced. I was awkward. Even though it was an accident and we only did it once he was amazing and I wouldn’t trade it for anything.

In the Dark

I was a sophomore in high school. 16 or 17, I can’t remember how old exactly. Not that it matters. We had been best friends for a while and I remember the first time I texted her saying “I like you more than just a friend.” She told me the feelings were mutual. I was excited because this was the first time I was sexually attracted to someone, but I was terrified because she was a girl. What if my other friends found out? What about my teachers? And my parents?! So our two year love affair was kept a secret. Our first kiss was in my bed, followed quickly by her unhooking my bra. She did it in a second. Had she been practicing? Should I have practiced? I tried to be as swift as she had been, but I fumbled, giggling in the darkness, her hair falling down into my face. We kissed while I miserably failed to undress her. I finally got it and we both paused. The lights were out. We couldn’t see each other’s bodies in the dark. But I was still so self-conscious. But we continued to strip down until we were naked. I guess she had been doing her homework, because she knew exactly what to do. When I flipped us over, I followed her lead, adding my own twist on things. We were both very quiet, keeping it down because my family was home. I think we were also afraid to let the other know that what we were doing felt right. There was no doubt in my mind that having sex with a woman was comfortable for me, but part of me didn’t want her to know how good it felt. We cuddled afterwards and whispered to each other until dawn. Eventually we fell asleep, my arms wrapped around her. When we woke up, we did it all again :).

What They Don’t Tell You in ‘The Talk’

Freshman year. Boy I met at a dance. Dorm room. Sober. Honestly? It was a relief. Looking back, it’s kind of a blur, though (un?)-fortunately I was one of those girls who kept a journal that, despite the best of intentions, just turned into a tedious account of ongoing interactions with boys. Needless to say, my first time, and those before and after it, was pretty well-chronicled. We’d been “together” for two months (two months! No one waits that long anymore!) before I was ready. The second time we ever hooked up I freaked out when we went to his room and he immediately started pulling off his pants. Ummm I was expecting some really intense making out and maybe I’d let him go to second base with my bra on? So when he whipped it out, my cute ‘lil celibate self doubled back and he didn’t mention it again. More guys should be like that.
A shortlist of things that I remember most about the first time: my heart exploding when he confirmed we were exclusive (prerequisite), trying for half an hour just to get it in (journal: “he’s…you know, 6’3”…”), the funny low noises he made, holyshitthequeefing, and that my butt had the worst fate. They do NOT warn you about those last two in The Talk. I considered myself lucky that we both had a sense of humor about it, but damn, what is it with guys treating a girl’s ass like their personal stress ball? Bruises, people. Overall, it wasn’t particularly romantic—I mean, it was in a dorm and neither of us saw stars—but it was right. For me it felt like I was finally inside this world that I’d been excluded from for so long. It wasn’t about power or edge; it was that I had finally crossed this threshold, the biggest threshold, into adulthood. I could make casual comments about good sex or bad sex or make the Mona Lisa smirk when I passed by him on the quad or in the dining hall. I didn’t wax philosophical about “losing it” versus “giving it”; I was just glad that I DID it. Because that meant more doing it. And rocking that sexy-sweet post-coitus glow. And, arguably most importantly, having an awesome excuse to buy exciting bras and underwear.

Doing All the Work

My first time was such a long time ago, plus the guy cheated on me so I’ve basically blocked out every memory of him, so I can’t remember much. I’ve also had way better sex with other boyfriends since we broke up, so why would I bother remembering the bad and awkward times? From what I can remember, he sucked at it. Every time he thrust and pulled back out to thrust again, he would slip out of me and have to find the hole again. He couldn’t even get it in at first, I had to do all the work. It was such a mess, and so sloppy, I’d be surprised if I got any pleasure from it.  I don’t blame myself for not remembering it!

Each story, whether good or bad, is memorable and unique. Whether you’ve “lost it” and loved it, “given it away” and regretted it, or have yet to “go all the way,” there is no doubt that everyone’s first time has a valuable story. Having sex is not shameful – don’t be afraid to share your story; you’d be surprised by all the people who want to share back!

Featured Image via Unsplash


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