Best I Ever Had

I’m attracted to you the moment we meet eyes in Chelsea Market. I recognize you immediately from your OKCupid profile: curly black hair, tan skin, thick, muscular arms, stocky but average height, in a blue and white button-down shirt. My eyes fall to the foor when we meet; I’m intimidated by your rugged good looks. Yet my nerves melt into a surprising comfort as we begin to joke around like old friends.


Everything we do together that night feels natural: giving our leftovers to a beggar, holding hands at a concert, imitating our funny pets. You get my silliness. I don’t have to explain. Late at night on the highline, we lean into each other and share our first kiss, our faces like two magnets pulled together.


Our first date becomes a second, and our second becomes a third the very next afternoon. We make out in my bed this time, and both our shirts come off. We lie there shirtless, so comfortable, as we open up OKCupid’s survey questions and talk about how we answered. We seem to agree on everything: sex, love, work, politics.


When it’s time to go, we kiss again, and your hand wonders into my pants. You tease me by stroking the soaked outside of my underwear. With your other arm wrapped around my shoulders, you have a way of putting me at ease. My mind goes blank. Then you reach into my underwear, with more force this time, and put a finger inside me, then two, moving them out then pushing them back in harder. I’m breathless. I moan into your mouth as I feel you push up into me.


But when you take your hand out and tug at my shorts, as if to ask me if I want you to take them off, the timing doesn’t feel right yet. “Let’s continue this at a later date,” I say.


“I was thinking the same thing,” you tell me.


Then, you ghost me. I don’t hear from you for over a year — until I’ve broken up with my next boyfriend, and in attempt to help myself get over him, I re-friend you on Facebook. You accept my request immediately, explaining that you got back together with an ex and felt terrible about it. You’re living in Boston now and tell me to let you know if I’m ever there. A few months later, I am. You say I can stay with you.


My first night in Boston, we go out for hot pot, and we talk as if we’ve been dating forever. Later, we continue what we started that past summer, just as I’d suggested. In the middle of a movie, with my head on your lap, I follow the magnetic pull upward to meet your lips. Soon, we move onto the bed. You’re behind me this time, with your fingers back in me, going harder until I’m screaming in ecstasy. You moan along with me, as if you’re feeling my pleasure vicariously, and then I collapse in your arms.


The next night, your fingers are doggedly back at it, rubbing circles on my clit. “I want you,” I tell you this time.


“Want me to get a condom?”




I’m 23 and socially awkward, and I’ve only gone all the way with two people, both serious boyfriends. I didn’t expect myself to do this. But I’m so attracted to you, I can’t help myself. I want you so much.


I love to feel your substantial weight over me, your thick cock inside me. There’s something about it that’s angled just right. You fuck me hard and good, not holding back as you grab my waist from behind and pound into me.


In the morning, I feel confused: What do I want from this relationship, anyway? You’ve told me you don’t want anything serious. I don’t want to get my hopes up. But whatever happens, I don’t regret it. It had to happen. You and I could not have gone our whole lives without feeling each other like this. It was as if nature intended it.


A few months later, you join me in New York for a music festival. The night before, we order pizza and eat it on the floor of my room, talking like old friends. Then, we move to the bed. After a few minutes of passionate kissing, you take off my shorts again, and your fingers are back inside me. Oh, how I missed those fingers. I start rubbing the outside of your shorts; eliciting an “Mm” from your mouth. “Do you have condoms?” you ask. I do — I bought some right before you got here, desperately hoping we’d get to use them. The “ribbed for her pleasure” kind. I hand you one.


As you strip down to put it on, I realize I’ve never actually seen you naked in the light. You have a bubble butt, which I love; my hands can’t wait to grab it. You’ve got a little bit of a belly and a lot of muscle. God, you’re sexy. I push you down on the bed and straddle you so that you’re sitting. You look a little squished against the wall. “Are you comfortable?” I ask.


“No.” We both laugh. I already knew that.


“Let’s try this,” you say, and you lie down on my pillow. Perfect — I have access to all of you this way. I can have my way with you. I climb back on top and gasp as I lower myself around you. Then, I start moving. I grind my hips back and forth over you, feeling your cock massage every crevice of my pussy and your stomach grinding against my clit.


God, that feels good. I completely lose control, using my knees on the bed and my hands on your chest to propel me faster and faster. Once you see how I like it, you sit up and grab my ass, hard, moving me back and forth yourself so that I barely need to do anything. Now that you’re taking care of me, I can just focus on the sweet sensations. I rest my hands on your muscular shoulders, giving up control, letting you take me on a ride.


I start screaming. I don’t think about the fact that my roommate’s in the next room. As far as I’m concerned, I’m not even in that apartment. I’m on some other plane, floating higher and higher up. I get louder.


Before I even realize what’s happening, I levitate up off of you and squirt all over your stomach. It surprises you as much as it does me. “Woah!” you say with fascination in your eyes.


“Sorry,” I laugh.


“No, it’s OK!”


I climb right back on you, grinding away, my arms wrapped around your back, milking you for all you’re worth. You love to let me use you; you just stare up in awe as I ride you. Then, time stands still. I grind into you harder and slower, throwing my head back, drowning in pleasure. I scream louder than I thought possible, not caring if I wake up the whole building. It’s instinct; I couldn’t stop if I tried. From wherever the hell I am in the universe (or possibly outside it?), I hear moans coming from your mouth as well.


Next thing I know, I’m laying on my stomach with my head on your chest, gasping for air, your cock still in me. I don’t remember how I got here. I blacked out. “Wow,” I pant, then erupt in laughter, kissing your chest. You laugh as well with a proud smile; you like knowing you’ve taken me to such heights. We kiss, and I climb off to go to bed.


It’s funny, I think: I was always told that the best sex was between two people in love. Yet my best ever had just happened with someone I’d only been on a handful of dates with and was not in love with. Or was I?


The next day at the festival, I can’t help but stare at you and smile, trying to stop my eyes from darting downward as I think of the magic wand between your legs. On our way home, you put your hands on my shoulders protectively as someone bumps me in the line. We sleep next to each other that night, but we don’t make love. I want to ask you, but you seem tired, and I’m too shy.


The next day, I cry as I walk you to a cab. We stop at the street corner for a prolonged kiss, and you almost miss your train. I wish you could stay forever. But I’m about to move to San Francisco, and I know you’re not looking for a relationship. So I let it go. At least I’ll always have these memories.


The truth is, I do love you. But love isn’t always meant to last a lifetime. Sometimes, it graces us just for a season or two, then another down the line if we’re lucky. And sometimes, those fleeting seasons are among the most beautiful of our lives. Just because this ended doesn’t make me any less grateful that it began. You’ve shown me what a relationship can be, what sex can be. I now know it can be so much more than I ever thought.


As expected, we drift apart after I move across the country. You’re with someone else now, if Facebook is any indication, and so am I. But still, to this day, you remain the best I’ve ever had. For that reason and many others, you’ll always have a place in my heart… and my pussy.