His First Time Was With Me, and I Don’t Forget It Either

I always considered myself a no-fuss kind of girl. Not in the bad sense, but in the most honest one: while my friends got tangled up in couple drama, jealousy, and late-night texts, I enjoyed sex as something simple and pleasurable, without labels or expectations. At twenty-eight, with a graphic design job that demanded more than was reasonable and a life that barely left me room to breathe, I didn’t have spare energy to deal with complicated feelings. My name is Valeria. I have green eyes, dark brown hair, and a habit of laughing at everything before it turns serious.

It all started on a Friday. We met up with Rodrigo and Claudia at our usual bar, the one with the uncomfortable chairs but the cold beer. The four of us were regulars, although Rodrigo and I had had something two years earlier. It ended well, with no hard feelings. He was already looking for something steady; I was still me.

That night, sometime between the second beer and the third, Rodrigo kept staring toward the bar with that expression of, “oh, look who’s here.” There was a man sitting alone on a barstool, wearing gray linen pants and a slightly wrinkled pale blue shirt. He was drinking sparkling water and looking at the foam as if it were the most interesting thing in the room.

—Do you know him? —I asked Rodrigo.

—That’s Santiago. He works at the Cultural Foundation, handles the historical archives. He’s a good guy, but he’s bad at socializing.

—Why don’t you call him over?

Rodrigo gave me a sideways look.

—Because you’re here.

—And what does that have to do with anything?

—That with you around, Santi goes completely paralyzed.

I was a little offended and a lot more amused. I told Rodrigo to bet whatever he wanted that in five minutes I’d have him sitting with us. I got up, straightened my blue dress, and walked toward the bar, looking straight at Santiago.

He saw me coming from far away. I saw him stop looking at his glass, saw him glance to the side to confirm that yes, I really was heading for him. When I reached him, his shoulders were tense and he was clutching the glass with both hands as if it were a life raft.

—Hi. You’re Santiago, right? I’m Rodrigo’s friend. We’d like you to join us at the table.

He opened his mouth. Closed it. Swallowed.

—I... don’t want to intrude.

—You’re not intruding. Come on.

I didn’t give him time to come up with an excuse. I took him by the arm gently and led him to the table. Rodrigo stood to greet him with that exaggerated warmth men use when they’ve just lost a bet. Santiago sat down between us, stiff as a post, not knowing what to do with his hands.

The discomfort didn’t last long. I asked him about his work out of genuine curiosity, and that changed everything. It turned out the Foundation archives included eighteenth-century documents, handwritten letters, maps that no longer matched anything real. Santiago talked about all of it with a precision and passion that had nothing to do with the man who had been frozen ten minutes earlier. His voice settled, he stopped stuttering, and in his eyes appeared something I hadn’t noticed when I looked at him from across the room: intelligence, and something harder to name.

That night we convinced him to come back the following Friday. And the one after that. By the third time we met, I’d learned that Santiago was thirty-two, lived just ten minutes from the bar, and had never in his life made the first move with anyone. Not because he didn’t want to. But because humiliation terrified him more than desire mattered to him.

What else I learned: he looked at me. A lot. With that long, lingering kind of stare shy people think is discreet and is actually the opposite. And in every one of those stolen looks I could tell where his eyes landed: on my neckline, on the curve of my thighs when I crossed my legs, on my mouth when I ran my tongue over my lip. A thirty-two-year-old man staring like a starving teenager. The idea of having him between my legs, awkward and desperate, started taking shape in my head that Friday, and by the time the third one came around I already knew exactly what I was going to do to him.

***

That third night, when the group started to leave, I told Santiago my bike had a mechanical problem and asked if he’d mind taking me home. It was a lie. My bike was perfectly fine in the building’s basement. But I wanted to see how he’d react.

He reacted as always: swallowed, looked away, said yes.

His car was a dark green hatchback, clean and orderly like everything he did. I got in beside him and, not by coincidence, the skirt I was wearing settled in a way that showed more leg than usual. Santiago stared straight ahead with a concentration that would have been admirable under any other circumstances. At every traffic light, his eyes darted for half a second to my knees before returning to the street.

We arrived at my building. He parked. Neither of us moved.

—Do you want to come up for a bit? —I asked.

The handbrake he pulled too hard was answer enough. Then he said, very quietly:

—I don’t know if that’s a good idea.

—Why not?

—Because... I’m not really sure how this works.

I looked at him. He was looking at the steering wheel.

—You come up, we have a drink, we talk. Nothing more than that, if you don’t want anything else.

He nodded without saying anything else, and we got out of the car.

***

My apartment has sand-colored walls and shelves everywhere, filled with books on design, typography, and a bit of fiction. Santiago came in and stood still in the middle of the living room, looking at the spines as if he’d found something familiar in an unfamiliar place. His body relaxed a little.

—Make something to drink —I said, pointing to the kitchen—. Whatever you find. I’m going to change and I’ll be right back.

Giving him something concrete to do was strategic: keep him from overthinking.

When I came back, he’d made coffee. Two cups. He was standing by the bookcase with one in his hand, looking at a book on historical cartography I’d bought at a fair and never gotten around to opening. I’d changed into more comfortable clothes, which in this case also meant less clothes: a thin tank top without a bra underneath and short shorts that barely covered my ass. My nipples showed through the fabric; I’d done it on purpose.

—Cartography of the Río de la Plata, nineteenth century —he read quietly, mostly to himself.

—You’d make better use of buying it.

He smiled without looking at me. It was the first time I’d seen him smile like that, slowly, without it seeming like an effort. When he finally looked up, the cup nearly slipped from his hand. His eyes dropped to my tits and then back up, red all the way to his ears.

We sat on the couch. We drank coffee. We talked about maps, about how geography got distorted depending on who drew it. At some point I put my hand on his knee, not hard, just resting there. I felt the muscle tense under the fabric. I slid my hand a couple of inches higher, along the inner thigh, and noticed the bulge already showing in his linen pants.

—Santiago, I like you.

I didn’t say anything else. I waited.

He looked down at his cup. Then at my hand. Then at me.

—I’m a virgin —he said.

He said it in the same tone someone would use to say, “I forgot my wallet.” Direct, no drama, as if he wanted to get the information out before nerves could stop him.

Two seconds of silence. Three.

—Okay —I said.

—Okay?

—Okay. Does that change anything for you?

He thought about the answer carefully.

—I don’t know how... I don’t really know what you do. I don’t want to do something wrong.

—What if I make sure nothing bad happens?

He looked me in the eye for the first time since we’d entered the apartment. In that look there wasn’t exactly fear, but something more like a question he didn’t know how to ask.

I took the cup from his hands and set it on the table. I moved toward him slowly, without any sudden gestures, and went for his mouth.

It took him a second. Then he kissed me back.

***

He kissed with a lot more intention than I’d expected. Maybe that was exactly it: without learned habits, without automatism. Just presence. His hands didn’t know where to go, and that turned out to be strangely intimate, watching him decide first on the sofa arm, then my shoulder, then my side, as if he were measuring everything. I took his right hand and placed it directly on my tit, over the tank top. I felt his breathing catch.

—You’re not going to break it —I told him against his lips—. Squeeze it.

He squeezed. Clumsy at first, firmer after that. I grabbed his wrist and showed him how to circle the nipple with his thumb, to pinch it slowly through the fabric until it hardened completely. When I moaned softly, Santiago opened his eyes as if he’d just discovered the sound was real.

I led him to the bedroom with his hand in mine. I didn’t pull him; we walked together.

—Sit down —I said, pointing to the edge of the bed.

He sat. I remained standing in front of him and pulled my tank top off over my head, unhurried, watching him. My tits were bare thirty centimeters from his face and he swallowed in a way that was almost audible. My nipples were standing up, dark, rigid. I took him by the back of the neck and pushed his face against them.

—Suck.

He did. At first timidly, as if afraid of biting me, but when I tangled my fingers in his hair and asked for more force, his mouth gave itself over completely. He was sucking one nipple while squeezing the other tit with his hand, alternating, and I felt every tug straight in my pussy. I was already wet and he hadn’t even touched me down there.

—Do you like what you see? —I asked, throwing my head back.

He nodded with a small, honest motion, without taking his mouth off my nipple.

I knelt on the bed and kissed him again, deeply, slipping him my tongue. This time my hands started unbuttoning his shirt while we stayed connected. When I finished the buttons, I parted the fabric and ran my palms over his chest. It wasn’t a trained body; it was simply his body: thin, with skin a little pale, with tension built up in the shoulders that I worked out under gentle pressure.

—Breathe —I told him near his ear.

He exhaled. The relief on his face was almost comical.

I went down his neck, his chest, his abdomen, leaving a wet trail with my tongue. I undid his belt with calm movements, lowered the zipper, and pulled his pants to his ankles. His boxer briefs rode up around his hard cock, straining the fabric, and a dark stain marked the tip. Santiago squeezed his eyes shut. I put a hand on his cheek.

—Look at me.

He opened them.

—Look at me while I take it out.

I hooked my thumbs in the waistband and slowly pulled his boxers down. His cock sprang against his stomach, bigger than I would’ve guessed from the way he moved through life: thick, red at the tip, with a vein running along the side and a drop of pre-cum shining on the head. I heard him hold his breath when he saw it exposed for the first time in front of another person.

I took it in my hand first, slowly, feeling how it responded to every variation. He gripped the comforter, let go, gripped again. I worked it up and down with a closed fist, using the moisture from the tip itself to lubricate the stroke, and with my thumb I brushed over the corona on every upward pass. Every time I reached the head he let out a short, helpless moan.

—Look what you had hidden away —I said, smiling—. It’s a gorgeous cock.

He babbled something that didn’t quite become a word.

When I lowered my head and took it in my mouth, he swallowed a sound that was half surprise, half something unnamed. I sucked him all at once, until I felt the tip bump the back of my palate. I stayed there a second, my tongue wrapping his shaft, and then I started moving up and down, letting saliva run down the base to his balls. I licked the tip as if it were an ice cream cone, then took it back down my throat. I grabbed his balls with my free hand and massaged them gently. Santiago was moaning without restraint now, his hips wanting to thrust upward but holding back.

—Va... Valeria... I’m going to...

I didn’t take it out. I kept sucking harder, squeezing his balls, and when I felt him start to shake I took him all the way to the back of my throat and swallowed him whole. The first spurt hit my throat hot and thick; the next ones filled my mouth. I stayed there, sucking him to the last drop, until he had to gently push me back because the sensitivity was too much.

I sat up, ran my thumb over the corner of my mouth, and showed him as I swallowed what was left.

It didn’t last long. It wasn’t supposed to last. What mattered was that he understood pleasure wasn’t something you had to earn or control, that you could just let go. When he finished, with a tremor running through his whole body and a moan that was almost disbelieving, I stayed still for a moment before letting him go.

—I’m sorry —he said immediately, voice rough—. I didn’t mean to... that fast.

—I did it on purpose.

He looked at me.

—I wanted you to understand there’s nothing wrong with this. You don’t have to control anything. And besides —I ran a finger over his lower lip— this way you’ll last longer for round two.

It took him a while to process that. Then, awkwardly but with intention, he opened his arms. I slid in between them. We stayed like that for a while in silence, his breathing settling little by little. I felt how, against my hip, his cock was starting to wake up again sooner than I’d expected. The good thing about thirty-two years without releasing was that it had its upside.

***

When I asked him to look at me, he did without looking away. I stripped off my shorts and panties in one motion and ended up naked on my knees over him, with my legs on either side of his hips. I took his hand and brought it down to my pussy. I was soaked; I made him notice by pressing his fingers into me.

—Feel how wet I am?

He nodded slowly, mouth parted.

—You did all this.

I guided his fingers over my wet lips, showed him how to open me, where the clit was, how much pressure to use. I put his middle finger inside me and taught him the rhythm, up and in, looking for that spot I only ever knew how to find the first time.

—Like this —I said, and felt him focus.

He learned fast. Or maybe he just paid attention in a way most people don’t. When I let go of his hand and he kept going on his own, he found the rhythm himself, and within a few minutes I was riding his finger, head thrown back, moaning his name. He slid a second finger in without being asked and pressed my clit with his thumb. I held myself back from finishing right then and there.

—Enough —I said, grabbing his wrist—. I want to come with your cock inside me.

I saw his face when I said that: the way his pupils dilated, the way his cock, already hard again, twitched against his stomach.

I handed him a condom, and I put it on him myself, enjoying how he trembled while I rolled it down his shaft. I settled on top of him, grabbed his cock with my hand, and rubbed it along the lips of my pussy, wetting the tip completely. He let out a low moan, almost a plea.

—Please —he murmured.

—Please what.

—Please... put it in me.

I smiled. With the tip lined up, I pushed down slowly, opening myself centimeter by centimeter to his cock. Santiago closed his eyes and made a sound that was pure surprise, pure physicality, as if his body was processing something his mind hadn’t finished understanding yet. When I had him all the way inside, I stayed still for a second, feeling him pulse against my walls.

—Open your eyes. I want you to see me fuck you.

He opened them. I started moving, first gently, bracing my hands on his chest, rising and lowering with my hips. I could feel his cock filling me with every descent, the head touching my back wall. I picked up the pace, bouncing on him, my tits moving in front of his face, and he watched them as if hypnotized until I grabbed one of his hands and put it on a breast so he could squeeze it while I rode him.

—That’s it, baby. Squeeze me.

I moved first. He followed after, with tentative motions that became more confident as we went on. He started thrusting from below, syncing himself to my drops, and suddenly every stroke was twice as hard. Our bodies made a wet sound when they collided and the bed creaked beneath us. At some point I stopped noticing the difference between what I was doing and what he was doing; we became one moving thing.

—Turn me over —I told him, almost out of breath—. Fuck me from behind.

It took him a second to understand, but when he did he gripped my waist with a new firmness and pulled me face-down, lifted my hips, and got behind me. I felt him enter me again in one thrust, this time deep in a different way, and I cried out into the pillow. He grabbed my hair without thinking too much, tugging just a little, and started fucking me with a rhythm that had nothing virginal left in it. With every stroke, my clit rubbed against the sheet. His hands squeezed my ass, spread it apart, then squeezed it again.

—Harder —I asked him—. Fuck me harder.

And he obeyed me. I heard his hoarse moans behind me, the smack of his hips against my ass, the sloshing of my soaked cunt around his cock. I felt myself about to come and shoved his hand down between my legs.

—The clit. Two fingers. Fast.

He did it. The bastard learned everything on the first try. With his cock pounding inside me and his fingers rubbing me outside, I couldn’t last another minute. His hands found my waist, firm, real, anchored in me.

—Valeria —he said, just that, my name, his voice broken.

It was enough.

When I came, it was with a long, sustained shudder that ran from my waist downward in waves, squeezing his cock inside me with every spasm. I came out screaming, without holding back, and felt liquid run down my thighs. Santiago held out for three or four more thrusts against my contractions and then he came too, this time with his eyes open, looking at me over my shoulder, as if he wanted to save that moment too. I heard him groan deeply and felt his cock throb inside the condom as he emptied himself.

He collapsed onto my back, sweating, panting against my nape. I stayed face-down, with him on top of me, feeling him slowly slip out of me.

***

After that we stayed still. The room was dark and he had an arm over my back, heavy and warm. His breathing gradually slowed.

—Are you okay? —I asked.

—Yeah —he said. A pause—. Very okay.

I smiled against his shoulder.

—Are you afraid it was too easy?

—I’m afraid it won’t happen again.

I hadn’t expected that. I propped myself up to see his face. He wasn’t joking.

—It can happen again —I said.

—Will you promise?

I laughed. It was the first time I’d heard him ask for something directly, without detours or apologies first. Maybe that was part of what he’d learned that night too.

—Yes —I said—. I promise.

He fell asleep before I did. I watched him for a moment: the even breathing, the relaxed expression, so different from the tension with which he’d entered the bar three Fridays ago.

I had always preferred uncomplicated sex. No commitments, no continuity. And here I was, promising something to a man who had fallen asleep in my bed after his first time, with the smell of semen and pussy mixing in the sheets.

The weird thing was that I didn’t regret it at all.