My First Time with My Best Friend’s Brother

I met Andrés in October of last year, when Sofía invited me to her house for the first time. He was in the kitchen making coffee, with his back to me, and when he turned around and looked at me I couldn’t look away. He had light brown hair, slightly wavy, hazel eyes behind black-rimmed glasses, and a calm smile that took an extra second to appear, as if he was always thinking something over before showing it.

He was twenty, one year older than me. He wasn’t the kind of guy who shouted at parties or needed to be the center of attention. He was quiet, straightforward, and had that habit of looking at you when you spoke, really looking at you, as if what you were saying mattered more than anything else in the room.

Over the following months I found any excuse to go with Sofía to her house. Sometimes I pretended I’d forgotten something there. Sometimes I just showed up “on the way.” Andrés always received me with the same ease, with no suspicion, or at least that’s what I believed. But he watched me. He watched me in a way I noticed and that he never turned into anything concrete.

That Friday afternoon I made up my mind almost absurdly, while I was putting on lipstick in front of the mirror. Today. I didn’t know where that certainty came from, but it was there, firm and clear. I wanted Andrés to be the first person to fuck me. I’d spent nineteen years carrying around my untouched cunt as if it were something that had to be handed over at exactly the right moment, and at last I felt that moment had arrived.

I called Sofía before leaving. She didn’t answer. I texted her: “I’m on my way to your house.” Nothing. She was probably in dance class, like every Friday. I went anyway.

When I rang the bell and heard his steps on the other side of the door, my heart started racing. Andrés opened it with his hair a little messy, wearing a white T-shirt and gray sweatpants, a mug in his hand. The pants outlined the bulge of his cock through the fabric and I couldn’t help dropping my eyes for a second.

—Lucía —he said, surprised but not uncomfortable—. Sofía isn’t here. Did you know that?

—I know —I replied—. I didn’t come for her.

There was a second of silence. Not awkward tension, but the kind of silence where two people really size each other up for the first time. He looked at me. I held his gaze.

—Come in —he said at last, stepping aside to let me in.

The house was quiet. His parents weren’t there. He set the mug down on the entryway table and followed me into the living room without saying anything. I turned to him before he could sit down.

—Andrés, I’ve been thinking about this for months. I don’t want you to feel pressured, but I have to tell you. I want you to be the one to fuck me for the first time.

He frowned, not in anger but in concentration.

—Are you sure you know what you’re asking me?

—Absolutely sure —I said—. I want you to put it in me. To be the first to open me up.

He didn’t answer right away. He came closer slowly, as if he wanted to give me time to back out, and when he reached my height he put a hand on my cheek. It was warm. He held my gaze one second longer, searching for something in my eyes, and then he kissed me.

At first it was a slow kiss, almost cautious, as if neither of us wanted to ruin it by moving too fast. But as soon as I felt him respond at the same rhythm I was pushing for, something gave way. I moved closer, he wrapped his free arm around my waist, and the kiss became longer, deeper. His tongue slipped into my mouth and I sucked it, biting his lower lip, feeling his cock harden against my belly.

I ran my hand over his sweatpants and squeezed. He was already rock hard, thick, throbbing against my palm. Andrés let out a short moan against my mouth.

We pulled apart a few centimeters and both laughed, for no reason, just because we were nervous and relieved at the same time.

—Come on —he said, taking my hand and leading me to his room.

***

The room was tidy, with natural light coming in through a slightly open window. I sat on the edge of the bed and he stood in front of me, taking off his shirt unhurriedly. He had broad shoulders, a smooth chest, and I couldn’t help running my hands over his stomach when he leaned down to kiss me again. I untied the drawstring on his sweats and pulled them down just enough to slip my hand inside. His cock was so hard it barely fit in his boxer briefs. I pulled it out. It was the first cock I’d ever touched in my life, and it felt heavier than I’d imagined, the tip already wet with pre-cum.

—Suck me off —he asked quietly, and those two words from him, so calm as he always was, made my cunt flood at once.

I knelt in front of him, my mouth at the level of his cock, and took it in both hands. I licked it first from the base to the head, very slowly, tasting the salty flavor of the tip. Then I took it into my mouth. I couldn’t fit it all, it was too thick, but I sucked it as much as I could, bobbing my head up and down, pressing my lips around the shaft and using my tongue around the crown.

—Like that, Lucía, like that… —Andrés held my hair back with one hand, not pushing, letting me do it at my own pace—. You suck cock so well for a first-timer, fuck.

I pulled it out with a wet sound and licked his balls too, one by one, looking up at him. His mouth was slightly open and his eyes were fixed on me. I took him back in, this time deeper, until the tip touched the back of my palate and I had to pull away coughing a little. A thread of saliva hung from my lip to the head of his cock.

—Come here —he said, and lifted me off the floor by my arms.

He started on my neck, with his mouth. Slow kisses, then pressure, then very gentle teeth on my skin. I had to bite my lip not to make noise.

—Does that bother you? —he asked against my throat.

—No. Bite harder.

He did. I felt him leave a mark and I didn’t care. He unclasped my top from the back with calm hands and let it fall to the floor. What he did next made it hard to keep breathing: he took his time with every part of my skin as if he weren’t in any rush, as if my body was something he wanted to stay in. He kissed my shoulders, went down to my tits and took them in his hands first, weighing them, pinching my nipples between his fingers until they were hard as stones. Then with his mouth: he sucked one nipple while pinching the other, switching from one to the other, nibbling them with a patience that drove me crazy and that no guy my age had ever given me, mainly because no guy my age had ever gotten this far with me.

By the time he finished with my upper half, I was already unable to stay still. My panties were soaked and my thighs were clenched without me realizing it, rubbing against myself in search of friction.

—Stay still —he told me quietly, and it sounded more like a caress than an order.

—I can’t —I replied, laughing—. My cunt is dripping, Andrés.

—Let me see.

He pulled my pants down and then my panties, and took a moment to look at me before doing anything else. Not in a way that made me uncomfortable, but in a way that made me want him to look at me. He opened my legs with both hands and let out a low whistle.

—You’re soaked, fuck. Your pussy’s shining.

He knelt on the floor, put my legs over his shoulders, and started with his tongue. Slowly at first, exploring, adjusting to every reaction from me. He licked my outer lips first, then parted them with his fingers, sliding his tongue between the folds, up to my clit and back down to the entrance. He learned fast. In less than five minutes he had found exactly the spot that made my whole body tense and my fingers clutch his hair.

He slipped a finger inside me while he kept sucking my clit. I was so tight I felt the finger as if it were something much bigger. He moved it slowly, curling it upward, and found a place that made my back arch against the sheets.

—Oh God, oh, keep going, keep going, keep going…

He slid in a second finger and sped up his tongue on my clit. I came close to the edge and pulled away without meaning to, clamping my legs shut around his head.

—Sorry —I said breathlessly.

—Don’t apologize —he answered, his mouth shining with my juices, and sat up to kiss me on the lips again. He kissed me with my own taste still on his tongue and it seemed like the dirtiest thing I had ever done in my life up to that moment.

He stood up and took off the rest of his clothes. I looked at him. It was the first time I had ever seen a man completely naked, not in photos but in person and less than a meter away from me, with his hard cock pointing toward me, thick and veined, the head red and swollen. The only thing I could think was that I wanted him to come closer and put it in me already.

—I’m going to go slow —he said, with a naturalness that calmed me more than anything else he could have said—. If at any point you want me to stop, you tell me.

I nodded.

***

I lay back on the bed. He positioned himself between my legs, ran his hand over his cock a couple of times to slick it with the moisture on the tip, and pressed it against my entrance. I felt the head pushing, sliding up and down over my dripping lips before finding the spot. He went in slowly, centimeter by centimeter, watching me the whole time. There was pain, yes. A sharp burn that made me clench my teeth and grab the sheets with my fists when he passed the barrier of my hymen.

—Okay? —he asked, still, with his cock buried halfway inside me.

—Yes —I answered, and it was true. It was a pain that made sense, a pain I had chosen—. Put all of it in me.

He pushed the last few centimeters slowly until I felt his balls against my ass. I was full to overflowing. The burn faded, turning into something else, a dense, warm pressure filling a space I didn’t know I had.

He started moving gently. Almost all the way out, then slowly in, out, in. I loosened my grip on the sheets. I started moving too, looking for his rhythm, pushing my hips up toward him every time he came down.

He kept building intensity little by little, as if the two of us were calibrating together how much we could give. I asked for more with my hips before I asked for it with my voice, and he understood without me having to say it.

—Harder —I said at last—. Fuck me harder, Andrés.

And he did, never taking his eyes off me. He started driving into me with long, deep thrusts, bracing his hands on either side of my head. Every time he rammed all the way in, the mattress creaked and a sharp moan escaped me.

—You’re so tight, fuck —he panted near my ear—. You’re milking my cock.

—Give it all to me, give it all to me…

He put my legs against my chest, bent, so he could drive into me from above at a more vertical angle, and from there I lost track. Time compressed in a way I couldn’t explain afterward. At some point I stopped counting minutes and there was only that: him on top of me, his weight, the wet sound of his cock going in and out, his rhythm, his face a few centimeters from mine. I moaned without shame, louder and louder. I dug my fingers into his back, dragged them over his shoulder blades. I heard myself saying things I hadn’t planned to say.

—I’m going to come, I’m going to come on your cock, Andrés…

My clit swelled against his pubic bone with every thrust, and suddenly something inside me snapped and I came screaming, clamping down on his cock with my inner walls while he kept thrusting without stopping. Andrés held on a few seconds longer, until he sank all the way in, went rigid, and pulled out his cock just in time to come in hot spurts over my belly and tits. He came a lot, a long white stream, and I watched him, hypnotized.

When he lay down beside me, the two of us breathing unevenly, I stared at the ceiling with a strange feeling in my chest, not of loss but exactly the opposite: of having arrived somewhere.

—Are you okay? —he asked after a moment, running a hand through my hair and absentmindedly wiping the semen from my navel with his thumb.

—Better than okay.

There was a comfortable silence. Then he spoke, with the same calm as always:

—There’s one more thing we can do, if you want. No obligation at all.

—What thing?

—Through the ass.

I looked at him. I didn’t feel fear exactly, but a curiosity that pulled harder than caution.

—Does it hurt more?

—At first, yes. But if we do it right, a lot less than it seems. And if you let yourself, you’ll like it.

—I want to try.

***

This time he went even slower. He put me on all fours on the bed, ass up and head resting on my arms, and took a long time just preparing me. He pulled a little bottle of lube out of the nightstand drawer, put a generous amount on his fingers, and coated my hole well. He started massaging the outside with his thumb, in circles, until I relaxed, and then he slipped in the tip of one finger. Then the whole finger, very slowly. Then two.

—Take a deep breath —he asked me—. Don’t clench. Open up.

I tried. I felt his fingers moving inside me, opening me, and a strange shock running up my spine that wasn’t unpleasant. He slid his other hand underneath me and rubbed my clit at the same time, and that made me push my ass back against his fingers without realizing it.

—You’re ready now —he said.

He put more lube on his cock, knelt behind me, and pressed the head against my asshole. When he started to enter, the sensation was more intense than the first time and an involuntary sound escaped my throat. It burned. I felt the ring stretch around the head of his cock and for a second I thought it wouldn’t fit.

—Do I stop?

—No. Keep going. Slowly.

He pushed another centimeter and held still. Another one. He held still again, giving me time to get used to it. My face was pressed into the mattress and I was panting with my mouth open, feeling my ass adjust around him little by little.

—It’s halfway in now —he whispered—. Do you want the rest?

—All of it —I said, my voice trembling—. Put it all in me.

When he had it buried all the way, he stroked my back from top to bottom until my shoulders relaxed. He started moving in tiny thrusts, just a few centimeters of give and take, and slipped his hand under me again to touch my cunt while he fucked me from behind.

It took me a few minutes to get used to that different pressure, denser, coming from another angle. Then something changed, and what had been only pain became something harder to name: an intensity that made the moans I let out sound nothing like complaints. Andrés noticed and adjusted the rhythm without my saying anything, lengthening his thrusts, gripping my hips with both hands and pulling me back against him every time he drove in.

—That feels so good, fuck, so good —I panted into the mattress—. Fuck my ass, Andrés, harder.

He fucked my ass harder. The sound of his hips hitting my cheeks filled the room, along with my moans, sharp and unchecked. He slipped two fingers into my cunt while he kept pounding me from behind and that double sensation made me come for a second time, trembling all over, melting against his hands.

Andrés held on a few seconds longer, thrusting faster and faster, and ended up pressing his forehead against my back a few seconds before coming inside me with a rough moan. I felt the spasms of his cock and the heat of the semen filling my ass, and that small gesture of his, forehead resting against my spine while he emptied himself, was what I liked most of all.

***

He turned on the bathroom light and came back with a damp towel. There was some blood on the sheets, not much, but it was there, mixed with the stains of semen and lube.

—Normal —he said matter-of-factly, and cleaned me carefully between my legs and from behind.

He helped me get dressed and then we went back to bed, lying on our sides, staring at the ceiling. Outside, the sun had begun to go down and the room had filled with a still orange light.

—Do you regret anything? —he asked after a while.

—Nothing —I replied.

And it was the simplest, most absolute truth I’d said in a long time. I could still hear the silence of the house and think that Sofía would come back at some point, that something would have to be explained or nothing would have to be explained, that the world would keep turning exactly as before. But I wasn’t exactly the same girl who had walked through that door a few hours earlier, and that seemed enough to me.

Andrés put an arm around my shoulders and I rested my head on his chest without saying anything else. There was no need.