My First Time


When we start messaging on OKCupid, I’m unsure if it will go anywhere. You’re a simply country boy working as a cleaner and attending community college, and I’m an Ivy League student and a city girl. But once we meet, I immediately feel at home with you. Logically, it shouldn’t work, but there’s an intangible soul connection. It’s evident in the weird things we have in common: We both dabbled in New Age spirituality as kids; we share the same irrational pet peeves (Lady Gaga, the phrase “have your cake and eat it too”); we’re both torn up inside when we see caged lobsters in grocery stores. And physically, you’re just my type: tall, skinny but well-built, blonde hair falling over blue eyes, freckles speckling your nose.


On our second date, after a movie on my bed, we lean into each other and kiss, your hand running up and down my leg. On the third, we slow-dance on the green outside my dorm. Afterward, I end things with another guy I’m casually dating.


“Does this mean I’m your boyfriend now?” you ask.




“That’s the best thing I’ve ever heard.”


I immediately change my Facebook status to “in a relationship.” I’ve never had a boyfriend before, and I’m so giddy.


It seems that you are, too. On our fourth date, you bring me Peter Singer’s Animal Liberation and some philosophy books your grandparents owned, and we talk about them at a hookah bar. Afterward, we lay side by side in my bed, making out, and you reach into my pants. Your finger slowly makes its way between my pussy lips and thrusts in and out as we kiss, leaving me breathless on my bed as you say goodnight.  


Before our fifth date, my mind turns to sex. How could it not? The thing is, I haven’t done it yet. Everyone’s surprised when they learn I’m a 20-year-old virgin. I talk about masturbation and orgasms and porn at parties. I have a shoebox full of sex toys under my bed. I’m openly sexual and sexually empowered. But I don’t want to share my sexuality with just anyone. I haven’t been in love yet, and I’m holding out for that feeling.


There have been times I came so close, times I backed out just before it went in. It took all my will-power. I have never felt a pull as strong as when I’m in bed with a man, feeling his cock push against me. It’s almost impossible to resist that unbearable ache of feeling empty, that pining to be full. But I have. I want to make sure that when it happens, I feel not degraded but even more empowered.


You’ve said “I love you,” and I think I may feel it too… but I’m not certain enough to say it back yet. Still, I don’t know how much longer I can hold out. And this wouldn’t be the worst situation to do it. I know you care about making it perfect for me, and I know you’ll only adore me more in the morning. I buy a couple condoms from my school’s vending machine just in case.


After dinner, we return to my room and lie down on my bed, where we slowly undress and caress each other. Your skin feels so smooth under my fingers. We decide it would be hot to touch ourselves side by side. As The National plays on Spotify, I take out my rabbit vibrator, and you put a hand around your cock and stroke yourself.


I’m so inexperienced, I’m embarrassed to look at it. But curiosity gets the best of me. I can see your muscular chest heave as you pump away at it; it’s swollen pink with desire — though not as pink as my own toy. As it vibrates and revolves inside my increasingly wet pussy, I can’t help but imagine it’s your cock instead, pounding in and out of me, exploring my uncharted territory. I’ve been using vibrators for years, but my body hungers for human skin fucking it, filling it, caressing it from the inside. It has hungered for so long. And now, it’s hungering for you. I turn to face you.


“Wanna know a secret?” I ask. “Sometimes, when I do this, I like to imagine it’s the real thing. It would feel good, don’t you think?”


“Yeah,” you pant.


“I think I want to do it soon.”


“How soon?”


“I don’t know.” But my body does. “I bought condoms.”


“Me too. How many?”




“Me too!” Once again, we’re on the exact same page.


“Want to get one?” I ask. You get up and scramble through your bag. I suddenly get nervous. “Please make this good for me,” I implore you.


“I wouldn’t want it any other way.”


“Just stop if it hurts, OK?” My friends have warned me about this and I’m terrified.


I lay on my back with my legs spread wide so that my pussy stretches open, and you kneel in front of me. I don’t think I’ve ever been this excited in my life. This is the moment I’ve been waiting for since I learned what sex was. Seeing your strong shoulders, well-defined abs, and angelic face above me in the dim light makes me want you so much. I can feel a part of me deep within my pussy open wide for you. My body wants to let you in just as much as my heart.


You’re more experienced than me, but not that much, and I can tell you’re a bit clumsy as you position your cock at my entrance with your hand. But all the clumsiness evaporates as you guide the head between my pussy lips, slowly move your hips forward so that it pushes its way through the entrance to my pussy, then glide further and further until the shaft’s all way in. Oh, god, yes. This is it. This is the sensation my body’s been craving for. But I remember my friends’ warnings. Maybe the pain is on its way. “Are you all the way in?” I ask.




“Oh. That feels really good!” You laugh at my relief.


With your hands on the bed on either side of me, you push yourself out so slowly, I barely notice you leaving — until you’re gone and I need you back in. You read my body and slowly inch yourself forward, touching me deep inside again.


We’re not doing anything out of the ordinary; just good old in-and-out missionary. But my god, the way it enlivens my nerves, the way it brings out my instinct, it feels like the most passionate, satisfying, divinely guided lovemaking in the world — as if we’re Adam and Eve having the very first sex.


“Right” is the best word to describe how it feels. This is what my body was designed to do. It feels like I’ve done it many times before, like there’s an ancient remembrance in my DNA. My hips know how to rise up to pull you in deeper. My hands know how to caress your back to bring you in closer. My voice knows how to cry out to make you press harder. My head knows how to lift up to kiss you for longer. Each time you thrust into me, it feels like the fulfilling of a deep emotional and physical longing, and each time you pull out, I feel like I will die if I don’t feel you back in again. There is something deeply nourishing about this, as if your cock is the food for my pussy.


With each stroke, my body opens up to you a little more, and you awaken a deeper part of me. I can feel you caressing my womb, connecting to my most inner being. Yet the further you push in, the hollower I feel, and the more I want you closer. You’re fanning the flame at the moment you put it out. My hips grind up against you more and more wildly, my soul needing to eradicate the distance between you and me.


Unfortunately for my soul, we hear a noise at the door. My roommate must be coming home. As quickly as we made the decision to start, we stop, pull ourselves up, get dressed, and greet her like nothing just happened — though, given my flushed cheeks and bright beam, she can probably tell something did.


We get ready for bed together and get under the covers. “Thank you for making my first time special,” I murmur between kisses as we lay holding each other. “How do you feel?”




“What kind of happy?”






“It was our first time.”


The next morning, you awake me by wrapping your arms around me and pulling me into your chest. There’s a throbbing deep in my womb unlike I’ve ever felt before. All I can think about is getting my fill of you again. But my roommate’s still asleep. “Want to do it in the bathroom?” I ask. We tiptoe down the hallway, and you lift me up onto the sink. I don’t need any warming up; I’m already aching for you. I lift up my nightgown and let you back into me.


I breath heavier as you thrust your body upward from a standing position. You cover my mouth so no one hears me. We go on long enough for you to finish this time. I love to feel your cock reach even further than before as it pulsates in me.


You clean yourself off and drive us to your parents’ house for the day. On the way, I beg you to pull over so we can do it in the car. You don’t think that’s a good idea, so I beg again once we’re there. You climb on top of me on the floor of your childhood room and pound me into the floor while I softly whimper. That evening, in the back of your childhood best friend’s car, I finally say “I love you” back.


On our next date, you undress and lie back on my bed, and I ride you for the first time. It takes me a while to get the hang of it; it’s unlike the way we’ve done it before. I’m grinding back and forth this time instead of in and out, and I can feel you higher up, with more pressure against my G spot. It feels so good, I can’t help but completely lose my inhibitions. I grind so hard, we end up on the other side of the bed. I’m squealing and screaming by the time I squirt all over your stomach. Then I do it again. I feel refreshed and uplifted and euphoric. This is the ultimate high. I climb back on you a few minutes later.


It goes on like this for months, and it never gets old. I ride you in the field outside your house, then we go home to wash my period blood off you. You make me squirt again and again by thrusting my vibrator into me when your cock gets tired. You wake me up in the morning with romantic spooning sex. We decorate each other with edible body paint and lick it off. There is so much to try. Everything is new.


It continues this way up until the end of our relationship nine months later. We ultimately realize we’re not the right match, as first loves often do. But what I learned from our relationship stays with me: that sex should always be thoroughly enjoyed by both people, should always be had out of genuine desire, and never has to hurt, whether it’s your first time, your tenth time, or your hundredth. I wish all women knew that sex could be so unequivocally positive from the getgo, if only you wait for the right time and the right person.