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His First Time

He was right where his text said he’d be, standing in the bathroom in front of the big mirror in nothing but socks. I could see that this 19 year-old twink, with his slender, toned body, short blond hair, and sweetly angelic face, was a prime internet catch—I thanked my star again for having such a compelling profile myself. At 6’1”, 173 lbs, still lean and mean at 38, I towered over the boy, who couldn’t have been more than 5’6” and 125 lbs, and I felt that size differential causing a stirring in my pants. So much you could do with a tight, tiny guy…. What’s more, this was his going to be his first time with another man. I’ve always loved popping the gay cherry.

Sticking out and up from beneath a perfectly flat, perfectly hairless stomach was a medium-sized, but superlatively erect penis. I could see the boy’s eyes fluttering a little as he watched me watch his junk—nervous, of course. So I smiled and said, ‘impressive,” to put him at ease, or at least more at ease.
As I entered the bathroom, he made to turn around, facing the mirror, head down, ass clenched up behind him. This wasn’t the way to start—I needed to warm him up a little. So I spun him around with one hand while at the same time kneeling to the floor. He was so surprised that he let out a little, high-pitched squeal as his cock slapped my cheek in the turning and kneeling. I got even more excited, because I knew I could expect more of those little noises later.

On my knees, I got straight to work. With my right hand I gently pulled down the eager mast of his cock a little, so it was almost parallel with the ground, and cupped my hand around the base. Then, with just the tip of my tongue, I swirled, gently, the head of his cock. I had done it a thousand times, and had it done to me, but apparently it was a new sensation for the twink, who shuddered with pleasure and tried to push his cock into my mouth. What the hell, I thought, it’s his first time, so I’ll let him. For a little guy, he had an impressive instrument, not very long but thick, smooth, and swollen with his anxiety and desire. I had to open my lips very wide, but then, my tongue cupped underneath his shaft, my throat relaxed, I was taking him all the way in, with faster and faster bobs of my head. He groaned, and out of the corner of my eye I was he was looking to the side, watching himself get sucked off in the mirror, by a reasonably handsome, orally talented older man—the twink was star of his own gay porno, having no doubt watched countless others leading up to this online Casual Encounter. He began to push his hips a little faster, and so I reached up with my free left hand and encouraged him to do so by swaying his hip into me.

This went on for some time, me deep-throating the twink, him getting more and more excited, and so I reached around behind his tiny, firm ass with my left hand and slipped it in between the cheeks, which were clenching and unclenching with every thrust. I let the moisture in there (sweat, or from an earlier shower? He looked so clean and fresh and pristine…) wet my index and middle fingers. These I pushed in deeper, right up to his puckered, tiny anus, I forced first my index in, about two knuckles, and then the middle finger. Tight and smooth, just like the rest of him. The twink yelped again, and jumped a little, but he did not try to pull away.

I dropped my right hand from the base of his shaft to his balls and scrotum, which were already up against my chin anyway. I cupped his balls, massaging them a little, and stuck the first two fingers of this hand back, to rub his choad. And all this without ever “breaking stride” with my mouth work on his cock. Now, he was being simultaneously stimulated in the ass, on the choad, beneath his balls and around his cock all at once. I was also, almost, holding him up in the air, riding my saddle of manual and oral pleasure. This produced the sensation of being somewhat held up by me, while demonstrating the strength I knew a submissive little guy like him would find attractive. His thin hips bucked back and forth in delight.

It was took much for him. As the distinct salty flavor of some leaking cum hit the back of my throat, I realized the boy was about to blow his load. I immediately stopped sucking, jerked more than slid out my fingers from his ass, and clamped down by squeezing, firmly and decisively but not painfully, on his scrotum.

I got his attention instantly, of course. “What’s wrong?” he half-moaned, half whispered, in a gesture of annoyance—or rather, of a frustrated desire that had become physical and demanding. He had been very close to cumming, then. And there’s nothing wrong with that, just as there’s very little I don’t enjoy about swallowing cum. Most times, give a guy 20 minutes, and his battery is recharged. But this was his first gay sex, and I knew that after he came, he might feel a little… weird. Awkward. He might not want me to proceed, and I knew from the second I walked in the room I was going to fuck this twink prodigiously. He wasn’t allowed to have second thoughts, not now.

I answered the first words either of us had spoken with a falsely stern severity: “you were about to cum. You can’t do that until I give you permission.”

He loved this, nodding eagerly—a boy who understood his duties and responsibilities, was all too happy to carry about my commands.
“Now,” I continued, “what comes next?”

The question threw him, a little, but only for a second. He straightened, his still hard and now quite slick cock bobbing up and down a little, and said, “are you going to fuck me now?”

“You have to ask,” I said, “nicely.”

“Ok, Daddy… would you please fuck me? Would you pop my cherry? Pretty please?” He was really enjoying this, but I could also see him looking at my long, hard cock—defining a dark, predatory mound and shadow in my pants—and worrying about how that would feel. Good: fear and desire combine well in sex.

I stepped up to him. I pulled off my shirt and he immediately began to run his hands down my thick, hairless chest, my hard, rippling abs. Clearly, he liked muscles, not having very big ones himself. He then began to undo my belt buckle, purposefully if a little clumsily. The zipper was next… and my cock flopped our, right into his hand. I don’t think he was expecting that, not right away, but I wasn’t wearing any underwear. It was probably the first cock he ever held that wasn’t his own. But his stroking was just right, a little pressure, a little moisture from my pre-cum, a little variation in speed. He made as though to kneel, but I stopped him: chances were, he’d botch his first blow job, and besides, I was ready for his ass now. But I held it off just another minute, grabbing his cock and rubbing it against my own and his hand while he kissed my beard and neck.

For the second time, I spun him without warning, flinging him back to more or less the position he was in before. His arms were spread out, the palms pressed to the bathroom counter, his head was slumped, a little, toward the mirror, and his back and legs made something more like a straight line in their travel to the floor.

I knew how to fix that. I went up behind him and once again got on my knees. I put my hands on his hips and pulled them back toward me, and then I shifted my hands again, spreading wide the cheeks of his ass, and took a look down there. Just as up front, smooth and hairless. Even after my probing fingers, his anus was so tight that I knew it would feel amazing wrapping my cock, and—but first things first.

I began to ream him, licking and kissing the area around his sweet little hole, which produced in him some other, moan-worthy sensation. I could hear more than see that he was stroking himself, and I thought I felt him squeeze his ass for just a second. He was loving it. We both were. Now, my mouth work got a little more involved. I made sure to cover the whole area with saliva by licking it profusely. I dragged my tongue lightly in a circle around his anus and then—the trump card—I pushed my tongue into his ass, about a half inch, and began to move it around.
Almost disaster again: I noticed that the twink was furiously beating off, that his breathing was heavy and fast, that he was rocking on his feet—he was going to cum again! I dropped everything, and he gave me the same look of tortured grief as before.

“I didn’t say you could cum, twink, so don’t.” I could see that, without my intending to, I might have given him the impression that I’d never let him climax at all. This would clearly disappoint him, but not very much—he was here, or rather, I was—so he could get his ass fucked, really fucked, for the very first time.

I stood up and positioned myself right behind him, my thick 8” of cock falling onto the landing strip or valley between the two cheeks of ass. He looked up at me in the mirror—fear, desire, but also a “let’s do this” look in his eye.

So that’s what we did. I started very slowly, sliding the wet, pulsing head of my cock little by little into his ass. He grimaced a little in pain.

“Shh,” I said, “it gets better, baby.”

He nodded, putting his head back down, and at that instant the head of my cock slipped all the way in. He let out some breath he’d been holding. That’s right, breathe.

I slid in deeper, almost 3” now. He was still tense. Another couple inches—god, it was so deliciously tight in there—and then, at first slowly I began to pull back out, then push back in, out, in out. As of this moment, I was fucking his ass. My hands on his hips, my eyes staring straight ahead into the mirror, or looking down at his back, which I occasionally had to press so his ass was up, I felt so, so, good. Not only was I having sex with a gorgeous little twink, not only was I deflowering his ass, but I had done things the way I wanted them. I was in control. The ass cheeks into which my cock kept plunging and diving was bobbing down below me, this little man now resting his head and his forearms on the counter was my toy. Pump, pump, pump.

The twink was starting to get into it. Inside him, the repeated thrusts of my cock had become like a pulsing massager, and he was playing with his hard cock again. More, he kept throwing back his hips as I pushed into him, to bury me even deeper inside him. He loved the way this felt.

So I gave him a little treat. I reached around with my right hand and found his cock, which he gratefully surrendered to my control. I tried to time the strokes of my hand to coincide with those my own cock was doing inside of him. It worked, and soon we were moving together in perfect tandem. He was watching me in the mirror now, my muscles rippling as I delivered this new kind of pleasure. He might have sex with women again (why?), but he would never not get ass-fucked again. He was hooked—quite literally, in fact.

“Fuck me, Daddy! Fuck me!”

I grunted in response. Harder. Deeper. Faster.

I could tell that, for the third time, he was about to cum.

“I’m about—“ he started to say.

“I am, too,” and I let myself chase down the orgasm. It was there, at the back of the part of him inside where I was—push, push, push and…

…we came together. His juice was so intense it flew over to the mirror and stuck there, as well as to my hand, as well as to its creator’s chest. Mine I decided to leave in him, so he could feel it squirt there, and dribble out later. Hours from now, he would still be dripping my cum. He would probably love it.
Still, I did lean down and lick and suck the rim of his ass one more time. I handed him a towel for this rest and grabbed one for myself. He was still facing the mirror, panting.

“Thanks,” he said.

And I just turned and left that place.