Our First Time Didn’t Go as We Expected

Carolina was my first real love. Not that childish teenage crush, but the first woman with whom I felt time stop when she looked at me. She was short, barely five feet two, with a round face full of freckles she hated and I adored. She had light brown hair, almost blond in the sun, and huge tits that didn’t seem like they belonged on such a small body. Her temperament was another story: she could go from the softest tenderness to the coldest silence in a matter of minutes. But I was gone.

We started out as friends. We studied together at university, in Medellín, both of us in our second year of communications. We shared classes, notes, and an endless coffee in the fourth-floor cafeteria. Months went by like that, until one afternoon, after a brutal exam, I asked if she wanted to go to the movies with me. We never made it to the movies. We ended up on a bench in the neighborhood park, talking until the lights went out, and when we said goodbye we kissed as if we’d been waiting years for it.

From that day on we were a couple. And from that day on, the waiting began. We both lived with our parents, we both had nosy siblings, neither of us had a car. The chances we got to be alone could be counted on one hand, and they never went beyond long kisses on stairwells, hands under a T-shirt in empty theaters, sighs against a wall in some corner of campus. In one of those corners, one night, she slipped her hand into my pants and grabbed me over my briefs, squeezing my cock until a moan escaped me, then ran off laughing her head off. Another time, I slipped my fingers inside her thong in the back row of the cinema and felt how soaked she was, but an usher came by with a flashlight and we had to stop. Desire piled up like pressure we didn’t know how to let out.

“Sooner or later it’s going to happen,” she’d tell me, biting her lip. “And it’s going to be unforgettable. I’m going to fuck you until you’re dry.”

I’d nod without knowing what to answer, because the truth was I was terrified. We were both virgins. I had read enough to know theory was useless when the time came, and she, who was the quiet one on those matters, only said she trusted me.

Finally, one Friday it happened. My parents were going to a birthday party out of town, my younger brother was staying the night at a friend’s house, and I was going to have the whole house to myself from three in the afternoon until the next day. I texted Carolina as soon as my mother shut the car door. Three words: “Come over here.”

She arrived in less than an hour, her face half made up and a small bag slung over her shoulder. I was waiting in the living room pretending to watch TV, with sweaty hands and a knot in my stomach. When I hugged her, I realized she was trembling too.

“Are you sure?” I asked in a low voice.

“I’ve been sure for six months,” she answered. “I want to come with you until I lose my mind.”

We went up to my room without saying much more. I locked the door, even though there was no one in the house, because that gesture made me feel like the rest of the world had ceased to exist. She sat on the edge of the bed and looked around with curiosity. It was the first time she had ever been in my room. I smiled at her, sat beside her, and we started kissing like so many times before, but this time without urgency, knowing that for once there was no clock.

***

I took off her sweater first, carefully, as if I were afraid of breaking her. Underneath she had on a white T-shirt that clung to her body. When that came off too, I just stared at her without saying a word. She was wearing lingerie I had never seen before: a dark blue lace bra that barely held her tits in and a thong of the same color, with embroidered details that disappeared between her hips and a tiny triangle of fabric that buried itself in her pussy.

“I bought it for today,” she whispered, a blush rising up her neck. “I wanted the first time you saw me like this to be today.”

I didn’t know what to say. I just kissed her again, harder, while my hands discovered the skin of her back. It was soft, cool, with a coconut cream smell that would stay in my head forever. I slid my tongue deep into her mouth and she sucked on it slowly, hungrily, while digging her nails into the nape of my neck. I pushed her down onto the mattress and settled on top of her, and when I rubbed against her I felt the bulge of my cock crushed against her pubic mound. Carolina spread her legs instinctively and began moving beneath me, grinding her pussy against my pants, breathing faster and faster.

“I’m already wet,” she whispered in my ear. “Since I left my house.”

Carolina started unbuttoning my shirt, button by button, biting her lip. When she got to my pants, she hesitated for a second. I took her hands.

“Easy,” I told her.

She finished taking them off, while I sat up to make it easier. I was left in my briefs, and in those briefs it was crystal clear how nervous and aroused I was: the tip of my cock was pressing against the fabric and there was a dark stain of pre-cum right where it pointed. She stared at it for a moment, eyes wide, and let out a little laugh. Then she reached out and squeezed me through the cotton, wrapping her fingers around the shaft, and I let out my breath in one go.

“Don’t look at me like that, you’re making me shy,” I protested, and we both laughed.

“It’s rock hard,” she said, not stopping squeezing. “I can feel it beating.”

I gently pushed her back onto the bed and kissed her neck, her shoulders, the line between her breasts. I fumbled with her bra unclasping it. When it dropped onto the mattress, I stopped to look at her. Her nipples were erect, thick, a light brown color that contrasted with her pale skin, and her tits spilled out to the sides under their own weight. I stroked one with my fingertip and felt her shiver. I took both in my open palms, squeezed them, brought them together, licked them from below until I caught one nipple between my teeth.

“Is this okay?” I asked.

“Don’t stop. Bite them, go on.”

I lowered my mouth and started sucking them slowly, alternating between one and the other, while she breathed harder and harder. I tugged one nipple with my lips, ran my tongue around the areola, then bit more firmly. Carolina gave a moan and arched her back, pushing her breast deeper into my mouth. I ran my hand along her thigh, slowly moving upward, and when I reached the edge of her thong I felt her curl inward. Not from fear, but from anticipation. I slipped a finger under the fabric and touched the damp hair, and farther down the soft, slippery flesh. She spread her legs wide and guided my hand with hers.

“There, deeper.”

I slid my middle finger in up to the knuckles and pulled it out shining wet. I put it back in, this time with two, and she started moving her hips against my hand, fucking my fingers with a desperation I had never seen in her.

***

“Turn over,” I asked, and she obeyed with a smile.

I slowly lowered her thong over her ass, over her thighs, over her calves, until I pulled it off her feet. She had round ass cheeks, a little bigger than they looked with clothes on, white and firm, and the cleft of her ass opened with every movement. I kissed each one, then gave them a soft bite, and ran my tongue between them until I brushed her little asshole. Carolina let out a strangled squeak.

“Hey, not there, you perv!” she said, but she didn’t move.

I made her turn around again. I looked at her whole, naked on my bed, with her tits falling to the sides, her belly button with its silver piercing, the brown hair of her cunt, her thighs shining with dampness, and I felt myself run out of air.

“Stop staring at me like that,” she said, covering herself with her hands.

“I can’t stop looking at you. You’re good enough to eat whole.”

I knelt between her legs. She was soaked, so much that her pussy lips looked swollen, shiny, parted like a cut-open fruit. She always complained she had too much hair, said shaving irritated her, but I didn’t care: the brown hair framed her sex like a painting. I lowered my mouth and kissed her there, first gently, then with my tongue. I parted her lips with my thumbs and traced the tip from the entrance to the clit, very slowly, feeling her whole body tighten. Carolina arched her back and made a sound I had never heard from her before, a sort of stifled moan that ended in a nervous laugh.

“I didn’t know you did it like that,” she murmured. “I mean, I’d read about it, but…”

“Me neither,” I said against her skin, and she laughed even harder.

I stayed down there a long while, lost. Time stopped existing. I ran my tongue all over her, kissed her lips, dipped the tip into the hole and pulled it out, sucked her clit with my lips like it was a little candy. I slid two fingers into her while I licked her, curling them upward, looking for that spot I had read about on some forum, and when I found it she jolted and drove her heels into my back.

“There, there, don’t move from there.”

I kept sucking her clit while I moved my fingers faster. She had a strange and delicious taste at the same time, sweet and salty, metallic, with a little something of the sea, and a smell that would haunt me for weeks. I could feel her tightening around my fingers inside with contractions that came more and more often, and her breathing became short, broken, almost an animal pant. Suddenly she went rigid, pressed my head against her pussy with both hands, and let out a muffled cry into the pillow. I felt her orgasm all the way through, throbbing in my mouth, running down my chin. When I lifted my face, she was looking at me with tearful eyes and a silly smile.

“I came,” she said, as if she couldn’t believe it. “I came in your mouth.”

“I noticed.”

“I want to do something to you too.”

***

I lay back and she pulled down my briefs. My cock sprang upward, hard, swollen, the tip purple and a fat drop hanging from it. Carolina opened her eyes wide and covered her mouth with one hand.

“That isn’t going to fit in me,” she said, half joking, half serious.

“It’s not that big,” I replied, laughing.

“It’s huge, seriously. Look at it.”

“You’re exaggerating.”

“I’m telling you it’s huge.”

We argued for a while like two idiots, in whispers, until she finally made up her mind. She took it in both hands, looking at it up close as if it were the first time she’d ever seen one—she was—and started moving her hands up and down. She did it slowly, carefully, asking me every so often if it was okay. I told her yes, to keep going, to squeeze harder, not to worry, it wasn’t going to break. I showed her how to twist her wrist at the tip and go down to the base, and she learned fast. The fat drop turned into a thread that she caught with her thumb and took into her mouth to taste.

“It tastes weird,” she said, wrinkling her nose.

Then she bent down and took me into her mouth.

The first sensation was warm, wet, enveloping. The second was clumsiness. Carolina didn’t know what she was doing, and every now and then her teeth would slip and I’d jerk. But I didn’t care. Watching her there, with my cock going in and out between her lips, with her hair falling over her shoulders and her eyes looking at me every so often to see if she was doing it right, with a string of saliva hanging from her mouth each time she pulled back, was more erotic than any video I’d ever seen online. I stroked her head, grabbed her hair into an improvised ponytail, asked her to go lower, to suck my balls. She did. She took them into her mouth one by one, very gently, while she kept jerking me with her hand. I closed my eyes and bit my lip so I wouldn’t come right there.

“Slower, slower,” I begged. “Or I’m going to cum.”

She stopped, smiled, looked up at me from below with her mouth still full of saliva and me.

When I opened my eyes, she was between my legs again, her face flushed and her breathing ragged.

“I want to do it,” she said. “I want you to put it in already.”

“Are you sure?”

“Sure. Fuck me.”

***

I took a condom from the drawer. I had bought it two weeks earlier, in a pharmacy far from my neighborhood, with absurd nervousness. I opened it with clumsy fingers and put it on wrong the first time, with the roll inside out. Carolina laughed. I did it again, this time properly, rolling it down to the base, and positioned myself over her, supporting myself on my elbows. She spread her legs and grabbed her knees to leave her pussy open wide for me.

“Look at me,” I asked.

I lowered my hand, guided my cock to her entrance, and rubbed it along her pussy lips a couple of times to get myself thoroughly wet in her moisture. Then I started pushing slowly. And that was when everything changed. Carolina made a grimace of pain as soon as she felt the pressure. I stopped.

“Keep going,” she said through clenched teeth. “Keep going slowly.”

I pushed a little more, just the tip. I felt an elastic resistance, a barrier that wouldn’t give. She squeezed her eyes shut hard. She made that grimace again, this time with a muffled moan that wasn’t pleasure. I stopped again.

“Cari, not like that,” I told her, stroking her cheek. “This is supposed to feel good, not like torture.”

“Come on, come on, it’s going to pass. Just shove it in.”

I tried two more times, attempting to get in little by little, and although the head went in all the way, the rest wouldn’t yield. Carolina clenched her jaw and a tear slipped out. I tried with more saliva, licked my fingers and lubed up my cock again, ran my tongue over her pussy to make it wetter, but when I pushed again the same wall came back, the same expression of pain. When I pulled out, I saw a small stain of blood on the latex, and even though I knew it was normal, something clenched inside me.

“We’ll stop,” I said.

“No, please, let me try again,” she begged. “I want to, really. I can do it.”

“I want it too, but not like this. This isn’t what your first time is supposed to be.”

Her face broke and she started crying. It wasn’t tears of pain. It was frustration, that intimate rage you feel when your body won’t do what your mind wants. I held her tight against my chest, still with my cock hard between us, and let her cry without saying anything.

“I always please you,” she said between sobs. “And today I couldn’t. I’m useless.”

“Don’t say that. You’re the best thing that’s ever happened to me.”

“I swear next time I’ll be able to.”

“There’s going to be many next times.”

I kissed her forehead, her eyes, her mouth. I wiped her tears with my thumb. Little by little the crying eased, and she went still, looking at me with those reddened eyes that suddenly seemed like the most beautiful in the world.

***

“Let’s take a shower,” I suggested after a while.

“Together?”

“Together.”

We got in the shower. The water was a little cold at first and we both jumped, laughing. It was strange seeing her naked under the white bathroom light, with no sheets half-covering her: her tits hanging with their wet weight, nipples hard from the cold water, the hair on her pubis stuck to her skin. I worked shampoo into her hair, avoiding wetting it more than necessary because she hated washing her hair without a dryer handy. She returned the favor with the soap, running her hands over my back, down my waist, slipping her fingers between my ass cheeks with a mischievous smile. When her hand reached my cock, still half hard, she soaped it slowly, sliding up and down with the foam.

“It doesn’t want to go down,” I told her.

“Then don’t let it go down.”

Then she knelt in front of me, without me asking. Water ran over her face, over her lashes, over her parted lips.

“You’re not done,” she said simply.

“You don’t have to…”

“I want to. Let me do at least one thing right.”

She started touching me with both hands, then with her mouth, this time more calmly and more confidently. She took me in all the way until I felt the head hit the back of her throat, coughed a little, spat out saliva, wiped her mouth with the back of her hand, and went back to it. I told her she was doing it perfectly, slower, faster, to lick the tip, to take my balls into her mouth. She did exactly what I asked. She would pull me out all the way, run her tongue from base to tip like I was an ice cream, then take me back deep again and make a sucking noise that drove me crazy. With her other hand she pinched the inside of my thigh, or fondled my balls, or touched her own pussy between her wet thighs. The water fell over us and my head spun. I felt everything building at the base of my spine, the tingling rising, my balls tightening. When I felt I was about to finish, I warned her.

“Where do you want it?” she asked, looking up at me from below with her mouth still a centimeter from the tip.

I didn’t get to answer. My body won. She took me back into her mouth and the first spurt went straight down her throat, but then she pulled away, maybe in surprise, and the rest came all at once, over her face, her tits, her stomach, that silver belly-button piercing of hers, which filled up as if it had been a small bowl. It was four or five thick spurts, more than I’d expected myself, hanging in strings from her chin to her nipples. Carolina stared at herself for a few seconds, eyes wide, and burst out laughing.

“Look what you did to me,” she said, still laughing, as she ran a finger over her chest and took the sample into her mouth. “Tastes better than I thought.”

I lifted her up and held her under the water, letting the shower wash us both clean. We kissed for a long time, tasting of salt and cheap shampoo and myself between our lips.

***

We dressed slowly, in a complicit silence. I walked her to the bus stop because her parents thought she’d spent the whole day at a friend’s house. Before getting on, she cupped my face with both hands and kissed me like she wanted to leave me a message without words.

“Next time is going to be perfect,” she said. “I’m going to fuck you until you forget your name.”

And it was, two weeks later. But that’s another story. The one I’m telling today is this one: the afternoon I discovered that losing your virginity wasn’t the epic event the movies promise, but something clumsy, funny, painful, and deeply human. The afternoon I understood that sex doesn’t have much merit when everything goes right, but becomes a memory forever when everything goes wrong and they still love you anyway.

Carolina was my first love, my first frustration, and my first certainty that the body doesn’t rule alone. The years went by, other partners came and went, an entire life passed. But when someone asks me what my first time was, I always struggle to answer. Because the real answer isn’t the night I finally entered her, two weeks later, on a borrowed bed. The real answer is that Friday afternoon, with briefs put on wrong, blue lingerie, a clumsy condom, and a shared shower after failure.

That was my first time. And I remember it every day.