The Curious Straight Guy Who Set Three Conditions

The phone vibrated on the little table with that dull persistence you only hear when the rest of the world is asleep. Half past one in the morning. The app was still awake even though I was on the verge of not being, and I almost ignored the notification. But the “like” came from a profile with no photo: a cropped torso, no face, black background. That old friend curiosity won out.

I opened the chat.

—Hi —I wrote, expecting the same lukewarm reply as always.

The typing dots appeared at once. “Hi. I’m new to this. I’m not really sure how it works.”

—Don’t worry, it’s easy. How can I help?

There was a long pause. Then a whole paragraph, no breaks, like someone finally letting out something they’d been holding in for far too long.

“I’m going to be honest because I don’t have patience for beating around the bush. I’m straight. I’ve had a girlfriend for years. But there’s something that’s been going through my head for months. I want to try being the receptive one. For the first time. In that, I’m a virgin.”

I stared at the screen. The confession, so direct, caught me off guard. He was the archetype of the curious guy: the one who carries a fantasy in secret and, one night with a couple too many drinks and a courage that won’t last, decides to take the plunge.

—Interesting —was all I typed—. And why me?

“Your profile looked normal. Not a veteran, not an exhibitionist. You seemed confident.”

—I suppose I am —I answered, with a smile he couldn’t see—. And I suppose you have conditions.

“Three. And they’re non-negotiable.”

—Go on.

“The first: condom. Always. No excuses.”

—Logical, I thought, and wrote it to him—. Fine.

“The second: you have to prepare me properly. I said I’m a virgin, so I imagine it’s not just a matter of putting a key in a lock. I want it to be pleasant. For it not to hurt, or to hurt as little as possible.”

The sentence made a knot in my throat and sent a warm rush much lower down. The bluntness of his language mixed with the innocence of the request was an explosive combination.

—Understood. And the third?

“The third is the most important. If at any moment, from the second you open the door until the end, I get scared, regret it, or simply stop wanting it, you stop. And you back off, no questions asked. No insisting.”

I read that condition three times. It wasn’t a request: it was a trust pact built on the possibility of refusal. And in that absolute vulnerability I found the most erotic point of the entire conversation.

—Agreed. Your three conditions are my rules.

“Seriously? That easy?”

—That easy. If you’re going to do it, do it properly. And feeling safe is the only way it can be.

“Send me your address. I’m fifteen minutes away.”

***

Sixteen minutes later the doorbell rang. I opened the door and found a guy taller than I’d imagined, his gaze lost somewhere above my shoulder. Neither handsome nor ugly. Normal. And in that normality lay all the appeal of the situation.

—Hi —he said, in a rough, slightly trembling voice.

—Hi, Darío. Come in.

I closed the door and the apartment’s silence became almost solid. We stood in the living room, the air thick with electric tension.

—Do you want something to drink?

—Just water —he replied.

While I poured him a glass, he spoke from the sofa, not looking at me.

—I don’t know if I’ll be able to do this. I’m really nervous.

I sat down beside him, but without touching him, at a prudent distance.

—It’s fine. You remember condition three, right? You can back out right now. Drink the water, leave, and it’s as if you’d never come. There’s no pressure.

He downed the glass in one swallow and set it on the table with a sharp clack. Then, for the first time, he looked me in the eye.

—No. I want to do it.

I nodded. I got up and held out my hand. His was sweaty. I led him to the bedroom, where the bedside lamp cast an intimate, shadowy atmosphere. He stopped in the middle of the room, rigid as a soldier waiting for an order.

—Lie face down —I whispered, trying to make my voice as calm as possible.

He obeyed. He stretched out on the bed with his face buried in the pillow. His body was a plank of tension. I knelt beside him and ran my hand down his back slowly, feeling his muscles contract under my palm.

—Relax —I told him—. Breathe. This is for enjoying.

My hand slid down his back to his waist, then to the start of his ass, firm and warm. I gently spread his legs. He allowed it, with a stiffness that betrayed his inexperience.

***

I picked up the lubricant. I squeezed a generous amount onto my fingers and rubbed them together to warm it. With my other hand I kept stroking his back while my index found his entrance, closed, tight. I began tracing circles around it, not entering, only caressing, telling him with touch that he was safe.

A muffled moan escaped into the pillow.

I kept at it for a good while until I felt the ring of muscle begin to yield, to loosen under pure contact and repetition. Then, with exasperating slowness, I slipped in the fingertip. Only a little. He tensed at once.

—Shhh. Easy. It’s just one finger. Take a deep breath.

—It hurts a bit —he said, voice breaking.

—It’ll pass. It’s the first contact. Hang in there.

I stayed still, letting him get used to the intrusion. With my thumb I massaged the small of his back. After a minute the pressure eased. I went a little farther, to the knuckle. His body trembled, but this time not from tension, from anticipation.

I began moving my finger, very slowly, exploring, searching for that spot that would make him change his mind forever. And then I found it. As I brushed it, his back arched like a whip and a low, deep moan filled the room.

—Fuck… what is that?

—That’s your prostate —I smiled—. And you’re going to love it.

I kept up the massage, now more confidently, and watched him relax completely, his hips beginning to move to the rhythm of my hand, looking for more. I added a second finger. The resistance was minimal. He opened for me. I prepared him carefully, with the dedication he had asked for, stretching him, lubing him up, turning that shut door into a passage that no longer resisted.

***

When I felt he was ready, I stopped. I stood up, went to the bedside table, and took a condom from the box. The sound of the wrapper tearing cut through the silence like a distant thunderclap.

But I didn’t kneel behind him, as he expected. I stood beside his head, level with the pillow. My erection, now free of clothing, was fully exposed, hard and firm. Darío lifted his face, awkwardly turning his neck, and his eyes met my cock for the first time, just inches from his mouth. He froze, pupils dilated, fixed on the shape, on the thickness.

With almost theatrical slowness I rolled the latex down over myself, never taking my eyes off him. The rubber snugged into place in one smooth motion all the way to the base.

—Do you know where this is going to be in a moment? —I asked him, my voice reduced to a low murmur.

His gaze drifted back to my erection, as if trying to memorize it. He swallowed hard. There was a second of hesitation that stretched into eternity. Then he spoke, in a voice firmer than I’d expected, charged with submission and desire.

—Inside me —he said—. It’s going to be inside me.

The bluntness of his answer, spoken with that newly minted innocence, was all the permission I needed. The pact was sealed. All that remained was to fulfill it.

***

I knelt behind him on the bed. I grabbed the bottle and poured a thick, cold stream over the latex, spreading it with my hand until it was completely covered.

—You’ll enjoy it more like this —I whispered.

I put my hands on his hips. They were narrow, his skin burning hot under my touch. I pulled him gently upward until he was in the perfect position, offered. I set the tip at the center, without going in, applying constant, promising pressure. I felt his muscle contract in an involuntary spasm against me.

—You’re going to be the one moving —I told him in his ear, my breath hot against his neck—. Push back, little by little. You take control. You decide when and how.

He stayed completely still for a few seconds, absorbing the order. It was the ultimate expression of condition three: the final power in his hands, right at the moment of greatest surrender. Then, with a visible tremor, he began to move.

The first movement was tiny, an almost imperceptible retreat. The tip sank in barely a millimeter and he stopped dead, with a muffled cry against the pillow.

—Breathe —I encouraged him, without letting go of his hips—. Keep breathing.

He drew in air, deep and shaking. He pushed back again, this time with more determination. I felt enormous resistance, a pressure refusing to give. And then, like a dam breaking, I slid in with a smooth, wet motion.

He went motionless, gasping, with only the tip inside him. His body was a taut bow. I gave him a moment to get used to the new sensation of being filled.

—Keep going —I ordered gently.

And he obeyed. A slow, hypnotic back-and-forth began. Every time he leaned back, I eased farther in, sliding through a channel that tightened and opened at the same time. He tested, advanced, sometimes retreated, startled by the intensity of his own sensation. Until, with one last slow, deep push, his ass came to rest against my pelvis. I was inside him, all the way.

***

I stayed still, letting his body accept me. His breathing was a rhythmic panting, as if he were taming something inside himself. After a long minute he spoke, his voice broken by the pillow.

—Fuck… —and the word sounded like a discovery—. I feel everything so full. It’s like pressure, but not a bad one. Like something that was always closed is now complete.

He paused, moving his hips with an experimental awkwardness.

—And there’s something else. A little stab. Every time I breathe or move a bit, you hit a spot and a current runs up my whole back. Like a cramp, but pleasurable. I’ve never felt anything like it.

His words were the live account of his initiation. Then, all of a sudden, he stopped.

—Stop —he asked—. Don’t move. It’s nothing.

I did as he said. I stayed like a statue, buried in him. I understood what he wanted: not condition three, he wasn’t backing out. He was asking for a truce so his body could surrender, so it could stop fighting and begin adapting. For a couple of minutes all we heard was our breathing. I felt the spasm of his sphincter relax completely, his muscles stop contracting and start to embrace me.

—It’s okay —he whispered at last—. It’s okay now.

And then he started moving again.

***

At first it was a slight rocking of the hips. But soon that rocking became deliberate. He leaned forward until I was almost out, then impaled himself again all the way in, slowly. A long, deep moan escaped him, a sound that was no longer pain or fear, but pure discovery.

He did it again. And again. Each thrust surer, deeper. He was no longer probing. No longer exploring. I let go of his hips, because he no longer needed guiding. I placed my hands on the bed, on either side of his torso, and simply enjoyed the show. He had taken complete control. The pace quickened, the sound of his skin against mine filling the room. He was no longer the nervous guy who had crossed my threshold.

Suddenly he stopped dead, with me buried to the hilt, breathing hard. It wasn’t a pause to rest, but to process: his head, flooded with new stimuli, needed to catalog what he was feeling. Then he changed the movement. It was no longer the linear back-and-forth from before. He began to circle his hips in slow, wide loops, as if sweeping his own insides with me. With each rotation came a different moan: sometimes a sharp gasp of surprise, sometimes a low, guttural growl.

And then he found it again.

On one especially deep turn, the pressure hit that exact spot. His body went completely rigid. A strangled cry caught in his throat. He froze, head lifted and eyes wide, staring into nothing, as if a jolt had run from top to bottom through him.

—What… what was that? —he managed to stammer, his voice shaking between panic and wonder.

I didn’t answer. I leaned back a little and entered him again, this time at a higher angle, deliberately searching for the same spot.

—There! —he shouted, no longer swallowing the sound. His legs trembled uncontrollably—. Fuck, there again!

The discovery had broken him. The man who had come into my apartment convinced of who he was had vanished, and in his place was someone driven by an instinct he hadn’t known was inside him. He abandoned the circular motion, abandoned caution. Now there was only one goal: feel that again, and again, and again. He threw himself backward, hunting for the exact angle, and each thrust tore a sound from him halfway between a moan and a roar. His hands no longer clutched the sheets: they twisted them. His body no longer trembled: it convulsed. He had found a switch he hadn’t known existed, and there was no way to turn it off.