My Best Friend’s First Time in His Room

I’m not going to pretend that what happened was an accident, although at first it did start as one of those impulses that cross your mind and make you act before considering the consequences. I’d been overwhelmed for weeks by university, by the people in my program, and by a string of dramas that had left me with zero patience. Whenever I feel that way, I always end up looking for the same man: my best friend, the only one I can flop onto a bed with and talk crap for hours until my anxiety subsides.

I’ll call him Darío. We’d known each other for years, since we were both clumsier, more insecure, and considerably more naïve. He’d always been reserved around women, excessively polite, one of those tall, slender guys who attract attention without realizing it, but who get tangled up the moment a woman holds their gaze for two seconds too long.

I knew a lot about his life, and he knew far too much about mine. Among those mutual confessions was one that occasionally came up as a joke and that, deep down, genuinely weighed on him: he was still a virgin. Not for lack of desire. Not for lack of wanting it. More because of a mix of shyness, fear of doing it wrong, and the habit of freezing up precisely when a situation might become real.

That day I arrived at his house with my backpack over my shoulder, my head full of complaints, and a tremendous desire to lock myself in his air-conditioned room. His parents weren’t home, something he told me as soon as he opened the door with that resigned half-smile he always wore when he saw me turning up without warning.

“They left food in the kitchen,” he told me. “They spoil you more than they spoil us.”

“Because I’m charming,” I replied, squeezing his cheeks.

He complained, pulled my hands away, and led me to his bedroom. It was a comfortable room, with the bed against the wall, a desk with the computer on, and that typical male mess belonging to someone who swears he knows where everything is, even though it looks like chaos. I threw myself onto the mattress while he sat in front of the monitor and started playing videos to keep me company while I ranted about half the world.

More than an hour passed like that, between anecdotes, laughter, and idiotic comments. I was in a better mood. So was he. I came up behind him to look at the screen over his shoulder, and that was when, without entirely planning it, he asked in a low voice:

“How do you girls manage to talk so easily to people you like?”

“Who are ‘you girls’?”

“Normal people,” he murmured, without taking his eyes off the video. “I freeze up. It always happens.”

I looked at him in profile. His jaw was tense, and he had that expression that was half embarrassed, half frustrated. It wasn’t news to me, but that day I noticed something heavier in him, as if he truly felt behind everyone else. Then I thought about how easy it was for me to touch, kiss, and tease, and about how completely inexperienced he still was in all of that.

The idea came to me just like that, all at once.

I leaned over, held his face in one hand, and kissed him.

It was a gentle kiss at first, barely a brush of lips that left him motionless. Darío took one long second to react, as if his brain were trying to understand what the fuck was happening. I smiled against his mouth and kissed him again, this time more firmly, parting his lips slightly with mine until I slipped my tongue inside.

He was clumsy. Very clumsy. But he was attentive too. When I set the pace, he followed me. When I gently bit his lower lip, he let out a short gasp. When I pulled away, he stared at me as if I’d just changed the language of the world.

“Well?” I asked, sitting on the bed.

“You just gave me my first kiss,” he finally said. “My first real kiss.”

I laughed.

“Then you learned something today.”

He ran a hand through his hair, still incredulous.

“Why did you do that?”

I thought for barely a second before answering.

“Because I wanted to. And because I came up with something better.”

He frowned. I sat up and faced him, enjoying the mixture of nerves and curiosity visible on his face.

“If you want, I can be your first time.”

He went completely still.

“What?”

“You heard me. No drama, no pressure, no making you feel like an idiot. I know you, you trust me, and I’m not going to judge you. I’ll teach you, we’ll try it, and that’s it.”

Darío swallowed. I saw his fingers tremble slightly on the arm of the chair.

“Are you serious?”

“Yes.”

“I don’t want you to think I’m taking advantage.”

“You’d be terrible at taking advantage of anyone, so I’m not worried. It was my idea.”

“But… right now?”

“Right now.”

I stood up and motioned for him to come to the bed. He almost tripped over his own feet, which made me laugh, but I didn’t tease him any further because he really was nervous. When he sat on the edge of the mattress, I knelt in front of him and kissed him again, this time without giving him time to think too much.

I guided him patiently, showing him with my mouth how to open, how to respond, how not to tense his jaw so much. My hands moved over his neck and chest, then slowly descended to the obvious erection beneath his pants. The moment I brushed the bulge with my palm, he let out a muffled moan into my mouth.

“Breathe,” I murmured. “You don’t have to do it perfectly. Just feel.”

I took his shirt off first. I wanted him to get used to being looked at. To feeling desired. He let me do it, red to the tips of his ears, with that mixture of embarrassment and arousal that was turning me on more than I’d expected. I took off my blouse in front of him, then my bra, leaving my tits bare. His eyes fixed on them with such clean, hungry intensity that my pussy clenched instantly.

“Touch them,” I told him. “They’re tits, not a bomb.”

He slowly raised his hands, as if he still needed permission. His palms were timid at first, barely making uncertain contact, but when he felt my hot skin and saw how I arched my back to offer him more, he loosened up. He kneaded my breasts more firmly, brushed my nipples with his thumb, and then leaned in to suck them.

That did surprise me.

He did it with delicious clumsiness: too softly at first, then harder, and finally with a little bite that drew a genuine moan from me. I grabbed his hair and pulled him closer to my chest. Feeling his mouth on my nipples, his hot breath, and those large hands squeezing me made me get wet fast.

“Like that,” I whispered. “Keep going.”

When he lifted his face, his mouth was wet and his eyes were dark with desire. I lowered my hand to his pants, opened the button, and slipped my fingers inside his briefs. His cock was truly hard, tense, hot, throbbing in my palm.

“Fuck,” I said, smiling. “At least this already knows how to work on its own.”

He let out a nervous laugh, but it was cut short when I lowered his pants and underwear in one go. I pulled them off, leaving him exposed and erect, the tip shining with precum. It wasn’t huge, but it was very pretty, thick enough, and completely stiff from the situation alone. I grasped it at the base and watched the air leave his lungs.

“Look at me,” I asked.

I kept watching him as I slowly moved my hand up and down, spreading the fluid from the tip over the entire shaft. My fingers squeezed just right, twisting my wrist slightly on the upward strokes, and every movement drew a more broken moan from him. Then I leaned down and ran my tongue over the tip, just one slow lick that made him squeeze his eyes shut.

“No, look at me.”

He obeyed.

I put him in my mouth without looking away from him. First just the head, surrounding it with my lips and sucking gently. Then a little more, halfway down, using my hand at the base to keep a steady rhythm. His breathing became uneven immediately, and I loved that sound. It was the moan of a man who didn’t know where to put his body because everything felt too big with arousal.

I went lower, relaxing my throat so I could take almost all of him. I felt the brutal shudder that ran through his abdomen when my lips reached the base. I began sucking him for real, moving up and down with my wet mouth, letting saliva run while I used one hand to caress his balls.

“Shit…” he gasped. “Shit, that feels so good.”

That encouraged me to pick up the pace. I sucked him without pretending to be delicate, eagerly, feeling his cock grow even harder inside my mouth. I licked his frenulum, the tip, his entire shaft, alternating deep sucks with slow sweeps of my tongue. He watched me at times, and at others threw his head back, completely surrendered.

I saw him coming before he said anything. His thighs trembled. His hips tried to thrust on their own. I held one of his legs to keep him still and took him all the way down, swallowing his entire cock while he moaned against me. He came with a sharp spasm, releasing a hoarse sound that made me incredibly horny. I felt his cum fill my mouth and kept sucking slowly, without stopping, to milk out every last throb.

When I finally pulled away, he was trembling.

“That was… I don’t even know how to describe it,” he stammered.

I wiped the corner of my mouth with my thumb.

“You don’t have to say anything. Now it’s your turn to learn how to use your tongue.”

I took off my pants and panties in front of him, hiding nothing. I opened my legs while sitting on the bed and watched him stare at my soaked pussy with almost reverent fascination. I liked that expression so much I bit my lip.

“Come here.”

He knelt between my legs. I grabbed the back of his neck and pulled him closer.

“First kiss it. Yes, like that. Don’t be afraid.”

His lips touched my pussy with a gentleness that made me shiver. He repeated the gesture several times, giving me clumsy, wet kisses, then ran his tongue over my entrance as if he were truly tasting something new. I let out a low moan and opened my legs wider.

“The clitoris is higher up. That little button. Lick it slowly.”

He obeyed at once. The first pass was uncertain, the second better, and the third already had purpose. I corrected his rhythm with my voice, telling him when to be softer, when to be firmer, when to keep his tongue flat and when to narrow the tip. He learned fast, the bastard. Very fast.

“Now suck it a little. That’s it… not so hard… yes, fuck, like that.”

He already had me moaning without restraint. My hands sank into his hair and guided him against my pussy, feeling his mouth grow more confident. When I asked for two fingers, he slipped them in somewhat clumsily, but he had good intentions and long hands that showed promise. I adjusted them for him.

“Curl them upward,” I told him, panting. “Look for the rough spot. Yes, there. Right there.”

He fucked me with his fingers while sucking my clitoris, and that combination brought me to the edge very quickly. I opened myself wider for him, rubbing against his face without shame, getting his nose wet with my pussy. He kept going, hungry, less timid by the second, more immersed in his role of making me come.

“Don’t stop,” I moaned. “Don’t stop, you bastard.”

But I stopped just before coming. I gently pushed him back and took a deep breath. I needed to feel something else. I needed to have him inside me.

“Lie down.”

He lay back at once, his face still shiny with my wetness. The sight sent a brutal jolt of desire through me. I went to my backpack, took out a condom, and opened it with my teeth.

“I don’t know how to put it on,” he admitted.

“That’s why I’m here.”

I slowly rolled it onto his cock, hard again, showing him how to hold the tip and how to unroll it properly all the way to the base. Then I straddled him without putting it inside yet. I only rubbed it between my lips, letting him feel how wet I was.

“Listen,” I said, leaning over his face. “If you come before I do, I’ll forgive you. But try to hold out, okay?”

“I’ll try not to die first.”

I laughed, then positioned him at my entrance. I lowered myself very slowly, feeling the tip open me up. He opened his mouth in surprise and gripped my hips tightly. I kept lowering until I had taken him all the way inside me. We exhaled at the same time.

“Fuck,” I whispered.

He was tense, motionless, almost frightened by the intensity. I stayed still for a second so he could feel how my pussy squeezed him, how it wrapped around him completely, wet and hot. Then I began to move. Slowly at first. Up and down. Letting him get used to the sensation of being inside a woman for the first time.

Darío looked at me as if he couldn’t believe it.

“Does it feel like this?” he asked breathlessly.

“Like this,” I told him. “And it can feel even better.”

I increased the pace. My pussy slid over his cock with a wet sound that filled the room. His hands rose to my tits and he began groping them without coordination, squeezing too hard at times, pinching one nipple and then the other. Nothing perfect, but genuine. And it was driving me crazy.

I leaned down to kiss him while riding him harder. I felt every thrust from inside, every rise and fall, the exact brush of his cock against my walls. His breathing turned into increasingly unrestrained moans, and I joined him with my own, letting the heat take over everything.

“Put your hands here,” I ordered, guiding them to my ass.

He obeyed and squeezed my buttocks while I impaled myself on his cock, faster and faster. The sound of my flesh striking his pelvis became harder and clearer, and it turned me on even more to feel him completely at the mercy of my rhythm.

“Now move your hips a little when I come down,” I told him.

He tried. Uncoordinated at first. Then better. Then suddenly he thrust upward and made me cry out. I smiled from sheer arousal.

“That’s it, there you are. You’re starting to understand.”

He held me more firmly and began thrusting upward whenever I descended. I kept riding him, but now there was a real response, a man beginning to fuck me properly beneath me. The combination was devastating. I felt his cock going in and out, the condom sliding wetly, his hands on my ass, his mouth swallowing my moans when he kissed me roughly.

I wanted to change positions before I came. I got off him for just a second and knelt on the bed.

“Come here. I want to feel you pushing into me.”

He moved behind me, nervous again.

“I don’t know if…”

“I’ll guide you. Grab it and put it in.”

He did it with adorable clumsiness, brushing my ass first, then my pussy, until he finally found my entrance. When the tip slipped in again, I threw my head forward and moaned. I pushed his ass with my hand to show him how deep to go.

“That’s it. Now get inside.”

He penetrated me slowly the first time, going all the way in as if he didn’t want to break anything. The second was firmer. The third came almost naturally. I arched my back, offering him more, and began moving my hips backward to receive him.

“Harder,” I asked him. “You’re not going to break me. Fuck me.”

That ignited something in him. His hands clutched my hips and he began pounding me more decisively. The sound changed again: wet, repetitive, his pelvis striking my ass, my bed creaking beneath us. Every thrust shook my entire body and forced me to bite the sheet so I wouldn’t scream too loudly.

“Shit, you’re so tight,” he blurted, now without the shy filter he’d had at the beginning.

“And you’re fucking me very well for your first time,” I panted. “Keep going. Don’t slow down.”

That praise went straight to his head. He fucked me better. Looser. More animalistic. One hand left my hip to search for my clitoris, clumsy but well intentioned, and I replaced it with my own so I could come the way I needed to. I touched myself quickly while he kept driving all the way in, again and again, his breath broken beside my ear.

I was at my limit. My pussy throbbed around his cock, and every thrust brought me closer.

“Don’t stop, don’t stop, don’t stop…”

I came with a powerful spasm, squeezing him inside me while my knees trembled. The orgasm rose through my belly and escaped my mouth in a filthy, long moan that was impossible to hide. I felt him lose control when he sensed my contractions.

“I’m going to come,” he said through clenched teeth.

“Do it. Come.”

He gripped my hips hard and gave me four more deep, desperate thrusts, then stayed buried inside me as he came into the condom with a hoarse gasp. He remained trembling behind me, pressed against my back, unable to catch his breath.

We stayed like that for a few seconds, sweaty and panting, hearing only the air conditioner and our bodies trying to return to normal. Then I slipped out from beneath him, and we both collapsed onto the bed.

I turned my head to look at him. His face was contorted with pleasure, his chest rising and falling rapidly, and an incredulous smile that filled me with tenderness.

“Well,” I said. “You’re not a virgin anymore.”

He burst out laughing, still breathless.

“I definitely didn’t expect my day to end like this.”

“Neither did I. Though I have to admit you turned out to be a better student than I thought.”

He pulled me close and kissed me again, but this time he wasn’t as clumsy. He’d learned something even there. I ran a hand over his chest and kept watching him, wondering whether this would complicate our lives or, on the contrary, lead us into territory we would no longer want to leave.

We went to the bathroom to clean ourselves up and returned to the room half-dressed, still laughing like two idiots who had just done something deliciously crazy. Then we turned the computer on again, as if it were possible to return to normal after teaching my best friend how to kiss, how to eat pussy, and how to take a cock with enthusiasm.

The truth was that nothing ever became exactly normal again after that.

And if you ask me whether I regret it, the answer is still the same: not one bit.