Men are obsessed with “the first time.” Everyone knows that. They want to be the first to conquer your soul, your body, the ones who got your virginity like it’s some trophy they can polish and brag about to their friends. But let’s be real: we women are worse. We romanticize it even harder. First date, first kiss, first time he says “I love you.” And then, of course, the big one: the first time you let someone inside you. Losing it.
Back then I was 22 and terrified that this was some huge, irreversible step, a privilege I was supposed to save for “the one,” the love of my life. I had a boyfriend, but he didn’t feel special to me. Sure, he made me fantasize about sex, got me all worked up and horny in that shallow way, but it wasn’t true love. We’d done the usual stuff: making out until my lips were swollen and tender, his hands sliding under my bra, my thighs shaking while he rubbed me over my panties and then inside them.
One night, we were at his apartment, watching some cheesy romantic comedy. It put me in the mood, but I still wasn’t ready for full-on sex. So I thought I’d use my mouth instead.
I wasn’t terrible at it, but watching him lying there, eyes half-closed, practically in ecstasy, I remember thinking, What about me? This doesn’t feel like love. I’m just serving him. I felt disappointed, almost used. I pulled back and tried using my hand instead. He wasn’t happy about the switch and kept trying to coax me back down. Eventually, he guided my head lower again, pushed himself deeper, and started thrusting into my mouth.
He didn’t last long after that. He pulled out at the last second, trying to be polite, I guess, but he missed completely. It hit my face in warm, messy streaks, the sharp smell cutting through everything. I froze, feeling it drip down my cheek, tasting it when it reached my lips. Right then, I would have preferred he’d just come in my mouth, be over and done, instead of leaving me sitting there sticky and marked. In that instant, the whole idea of oral sex turned sour.
Afterward, our relationship started to fade. I wasn’t in the mood for another round of that, and he clearly wanted more, so two weeks later, he ended it.
Months late,r I met Leo. He was 33, funny in this dry, understated way that always caught me off guard and made me laugh when I least expected it. There was something quietly authoritative about him. I felt seen in a way I hadn’t before. It made my pulse race and calm at the same time.
When I told him I was still a virgin, he just raised an eyebrow, took a slow sip of his drink, and said, “Okay.” No fireworks, no possessive gleam in his eye. Just okay. It threw me off at first how little it seemed to matter to him. But honestly, it was a relief. I think he wasn’t too happy about no blowjobs either, but he pretended not to care.
We dated for weeks without any rush. He kissed like we had all the time in the world, slow, deep, filthy. His hands explored every inch of me, patient and deliberate. You won’t believe me, but those long make-out sessions and heavy petting left me soaking wet. My panties would be drenched, and I’d feel almost embarrassed when his fingers brushed there and he felt how ready I was.
I was falling for him, hard. Not in that dramatic, movie way, but in the quiet, real way where you start imagining what it’d be like to wake up next to someone every morning. I trusted him. That’s what made the difference.
One night we were already in bed, in our pajamas, just cuddling before sleep. He was teasing me gently, his palm cupping my breasts. The warmth of him, the safety of his arms around me, it all clicked. I grabbed his wrist and guided his hand lower, between my legs. He stripped me quickly and reached into the nightstand drawer for a condom. I didn’t say anything; it was a silent yes. He rolled it on, settled between my thighs, and pressed in.
It hurt. Not the pretty, romantic kind of hurt you read about in books. My whole body locked up. He sensed how tense I was and stopped immediately. I told him to continue, but he knew it wouldn’t be the best idea. He gathered me against his chest, kissed my temple like I was something fragile and precious, and held me while I whispered, “I’m sorry.”
“Don’t be,” he murmured.
We fell asleep like that, naked, curled together. I woke up to morning light and Leo kissing my shoulder, his hand already sliding down my stomach like it was the most ordinary thing in the world. A few minutes later, I was wet again, nudging my legs apart. No swelling music, no rose petals scattered on the sheets. He pushed in slowly. I tensed, bracing for that horror-movie stab of pain. It still hurt, but somehow it didn’t matter as much anymore, because he was looking at me like I was everything, whispering my name softly, checking in with his eyes. He kept going until he was fully inside me. He lasted maybe ninety seconds and came with a quiet grunt.
Then it was over.
I lay there waiting for the angels to sing, for fireworks, for some profound life-changing epiphany. But nothing came. I waddled to the bathroom, mortified by the blood streaked on my thighs like I’d started my period early. I cleaned up, came back, and crawled into bed like nothing monumental had happened. I felt strange for a moment, a mix of regret and relief, but soon I realized it didn’t matter.
Two weeks later, we were having sex almost every day. I quickly learned there are so many other first times in a sex life: my first time cheating on Leo, my first dildo, my first orgasm from penetration. All those “firsts” only matter if you let them. The real freedom comes when you stop keeping score.
By the time I was 25 and backpacking through Europe, everything had gotten a lot more interesting. At a charming little hotel in some sun-drenched town, I met two charming friends, Alex and Marco. We shared some good wine on the balcony, trading stories about bad hookups and worse hostels. Strangely, I was attracted to both of them, and I didn’t feel like choosing just one. We ended up in my room, clothes disappearing somewhere along the way. It wasn’t the perfectly choreographed scene most guys seem to imagine, no complicated positions, no one pushing for the things porn makes obligatory. I then learned that every experience mattered, painful or messy or perfect. The difference was learning to choose them myself, on my own terms, instead of waiting for someone else to decide what they should mean. That’s what finally felt like freedom.
