Greg’s question still hung between us, heavy, raw.
“You wanna go further?”
My chest was heaving, lips swollen, chin wet with spit, my cock straining against my shorts. I didn’t even have to say it…my whole body was screaming yes.
But my voice came out anyway, shaky, low. “You mean… fuck?”
Greg grinned, lazy and cocky, like he loved hearing me say it out loud. “Yeah, man. What do you think?”
I swallowed hard, eyes flicking down to his cock, thick and pulsing in my hand. “I… I don’t know, Greg. I mean, fuck. Look at you. You’re huge. I don’t even know if I can…”
He laughed, a low, rumbling sound that made my stomach flip. “You saying this cock’s too much for you?”
Before I could answer, he leaned forward, tapped the wet head of it against my tongue. A string of spit connected us. “C’mon, you took it in your mouth just fine. Don’t psych yourself out.”
I let out a muffled sound, my tongue flicking against the tip without thinking.
Greg chuckled again, softer this time, almost reassuring. “Relax. I’ve never fucked a dude either.” His hand slid through my hair, gentler now. “Don’t worry, we’ll figure it out. We’ll take it slow. Together.”
That word together sent a jolt through me.
He tilted his head, eyes narrowed like he was thinking it through. “Shit, man. I don’t even know if it’ll feel the same. Like…pussy, ass…fuck if I know. But I wanna try it. With you.”
My throat tightened. “Greg…”
He smirked, but softer, like he could see I was nervous. “Hey. Don’t overthink. Just trust me.”
I nodded, breath shaky. My hands were trembling, my whole body wound tight.
Greg leaned back, cock resting heavy against his thigh. “Why don’t you strip down for me, huh? Let me see you.”
The heat shot straight to my face. But I stood, shaky, and hooked my thumbs under my shirt. It peeled over my head, leaving my chest bare, my skin flushed. I could feel his eyes on me, heavy, following every move.
My shorts were next. They slid down slow, pooling at my ankles. My cock sprang free, hard and dripping, my briefs sticking to my legs from how wet I already was.
Greg let out a low whistle. “Fuck, look at you. Already leaking.”
I froze, embarrassed, but his grin only widened.
“Don’t hide it, man. That’s hot as fuck.”
I shoved my briefs down the rest of the way, kicking them aside, standing n@ked in front of him. My skin burned under his gaze.
Greg sat up straighter, eyes roaming over me like he was memorizing every inch. Then he jerked his chin toward the bed. “C’mon. Get on up there.”
I climbed onto the bed, heart racing, laying back against the sheets.
Greg smirked. “Spread your legs for me.”
The words hit me like a punch. My thighs trembled as I obeyed, spreading wide, exposing myself to him.
Greg stood, finally moving, and my breath caught at the sight of him towering over me. He stripped off his own t-shirt, muscles flexing, then shoved his shorts and briefs down in one motion, kicking them aside. His cock hung heavy still glistening from my spit.
He climbed onto the bed, moving behind me, his presence overwhelming. His hands slid down my thighs, strong… until he spread me open.
“Shit…” he breathed, his voice rough with surprise. “That’s a cute tushy you got there.”
I buried my face in the pillow, grinning despite myself. “Gregg….”
Greg laughed, the sound warm. “Nah, man, I mean it. You’re… smooth. Fuck.” He spread me wider, his thumbs brushing against the sensitive skin, making me jolt. “Never thought I’d be here. But damn, I like this view.”
I shivered, every nerve alive under his touch.
Greg leaned closer, his breath hot against me. “You nervous?”
“Yeah,” I admitted, my voice small.
He squeezed my thigh gently. “Good. So am I.”
That made me smile, relax just enough.
Greg’s fingers traced lightly, teasing, exploring. My body tensed, but the way he touched me…curious, unhurried…made me melt a little more each second.
“Relax,” he murmured again, almost like a promise. “We’ll figure it out.”
His hand slid up my back, grounding me. His cock pressed against my thigh, hot and heavy, a reminder of what was coming.
“Fuck, you look good,” he muttered, spreading me open wider.
My heart was racing so hard it hurt, but underneath the nerves was something stronger…want.
I turned my head, looking back at him, my voice shaky but steady enough. “Greg… I want it.”
He froze for a second, eyes locking on mine. Then his grin returned, slow and hungry. “Yeah? You want this cock?”
I nodded, biting my lip.
Greg spat into his hand, coating his cock up, the wet sound filthy in the quiet room. He wrapped those big fingers around his shaft and stroked slow, milking himself just enough that I could hear it, the wet slide of his spit over thick skin. Then he pressed the swollen head against me…just resting it there, hot and heavy, like a brand.
“Fuck…” he groaned, his voice low, almost pained. His eyes fluttered shut for a second. “You feel warm already.”
I gasped, my body clenching tight, every nerve sparking at the weight of him nudging right at my ass. It wasn’t even in, just there, threatening, teasing and still it felt like more than I could handle.
Greg leaned over me, chest brushing my back, his breath hot at my ear. “You ready, Alex?”
The question vibrated through me, heavy and electric. My whole body ached with it, but I still hesitated, chewing my lip.
He must’ve felt me tense, because his hand stroked slowly up my thigh, grounding me. “Hey, relax. Don’t overthink it. Don’t worry…I’ll be gentle.”
His voice dropped, steady, confident. “I’m not gonna hurt you. Just take it slow. You trust me, right?”
I nodded, quick and shaky.
“That’s it,” he murmured, kissing the side of my shoulder, the scruff of his jaw scraping lightly against my skin. “Just breathe. Let me take care of you.”
I inhaled deep, exhaled shaky. The tension in my body eased just a little.
Then I felt it again…the blunt crown of his cock nudging, rocking gently against my hole. Not pushing in, just testing, knocking at the door. A filthy tease.
Greg groaned softly. “Fuck, look at that. Your ass is excited.”
I whimpered, face pressed to the pillow. “Greg…”
“Shh.” His hand rubbed circles into my hip. “It’s good, man. You’re good. Just let me—”
He spat again, this time not into his hand but directly onto my ass. The warm wetness landed on my hole, sliding down my crack. He spread it with his thumb then pressed the head of his cock back against me.
“Better,” he muttered, half to himself. “Nice and wet now.”
I jolted when he gave a light tap…his cockhead smacking against my hole, playful, taunting. Then again, a sharper slap…
Greg chuckled, low and dirty. “Like teasing you, man. Watching you twitch every time I tap it right there.”
I buried my face deeper into the pillow, groaning.
“You want it, don’t you?” he asked, grinding the fat head in little circles against me. “Your tight little hole’s begging for it.”
“I—I don’t know if I can take it,” I admitted, voice small, breaking.
Greg kissed the back of my neck, his lips warm, his beard rough. “You can. Trust me. I’ll go slow. We’ll stop if it’s too much.”
He spat again, rubbing it in with two fingers this time, massaging the rim of my hole until I squirmed from the pressure. Then he lined himself up again, cock wet and heavy, and just nudged…soft, insistent, steady.
“Fuck…” I gasped, my fingers gripping the sheets tight.
“That’s it,” Greg whispered, his voice low and soothing. “Feel that? Relax…Not even inside yet.”
He rocked his hips, sliding the head up and down my crack, dragging it across my hole, smearing spit and precum all over me. Each pass made me shiver harder.
“Ah fuck,” he muttered, almost like he was talking to himself. “Never thought I’d want this. But fuck, your ass is fucking perfect.”
My body trembled, equal parts nerves and heat. “Mr. Lawson”
“Yeah?” he murmured, pressing the crown against me again, steady and firm but still not breaching.
“I want it,” I whispered, voice cracking. “But… just…just go slow.”
Greg groaned, kissing my shoulder again. “Don’t worry. I’ll take care of you. I promise.”
His cock nudged harder, a little more pressure, enough to make me whimper into the pillow. Then he eased back, just to rub himself along me again, teasing me into desperation.
“Shit,” he groaned, his voice ragged. “If it feels this good just grinding against you… I can’t fucking imagine being inside.”
My body clenched, hole fluttering at the thought.
Greg chuckled softly, almost in awe. “Fuck. You’re suck-ing me in already, and I’m not even in yet.”
His hand slid up my chest, pulling me back against him, making me arch. His cock pressed firm and steady at my hole again, heat radiating, the tip snug against me, throbbing.
“You ready?”
And when I whispered yes, breathless and wrecked, I knew…next time, there’d be no stopping.
Greg’s cock was pressed against me, heavy and pulsing, smearing spit and precum all over my hole. He had me on my knees at the edge of the bed, face buried in the sheets, ass spread open in his big veiny hands. Every time he nudged the head of his cock against me, my whole body twitched, nerves sparking like a live wire.
He groaned above me, his breath ragged. “Relax, Alex… I got you….. You ready?”
My voice cracked, muffled in the sheets. “Y-yeah.”
Greg bent down, chest grazing my back, his mouth brushing my ear. “Relax. Just breathe, man. I’m gonna go slow. I’ll stop if it’s too much.”
I tried to breathe, but my heart was pounding too fast. I could feel the heat of his cock pulsing at my hole, feel the weight of it pressing steady. My body was trembling, clenching before he was even inside.
“Hey,” Greg said softly, but firm. “Breathe with me. In…” He dragged the head of his cock up and down my crack, smearing more precum against me. “…And out.”
I exhaled hard, my hole twitching when he tapped his cock against it again.
“Good boy,” Greg murmured, kissing the back of my neck. Then he lined up and pushed, just enough for the tip to catch.
My breath hitched, my body tensing like I’d been shocked.
Greg groaned, low and guttural. “Fuck… you’re so tight.” His hand rubbed my hip, steady, grounding me. “Don’t fight it. Just let it happen.”
I buried my face deeper into the mattress, my fingers twisting the sheets. My ass clenched around the fat crown of his cock as it pressed and stretched me open, slow and relentless.
“Easy…” Greg whispered. “Don’t squeeze. Just breathe.” He spat again, rubbing it down with his hand, then pushed forward another inch.
“Aah—fuck—” I gasped, my whole body jolting.
Greg’s hand slid up my back, calming me. “Shh, it’s okay, Alex. That’s just the tip. You’re doing so good boy.”
I panted into the sheets, sweat already sticking my hair to my forehead. My hole felt like it was being split in two, burning and full and new all at once.
“You okay?” he asked, his voice tight but patient.
“Yeah… yeah, Mr. Lawson…”
Greg groaned, his cock throbbing against me. “Fuck, hearing you say that…” He gritted his teeth, pushing another inch inside.
I moaned, my body arching back against him, a raw sound ripping out of my throat. “F-fuck…”
“That’s it,” he whispered, kissing my shoulder. “Take it. You’re opening up, man. You got this.”
“Relax…”
The pressure eased slightly as my body adjusted. I sucked in air, moaning again as his cock slid deeper, inch by inch, stretching me more than I thought I could take.
“Holy shit,” Greg gasped, sweat dripping off his brow onto my back. “I can’t believe I’m inside you. Feels so good, Alex. Better than anything.”
He bottomed out with a groan, his hips flush against my ass, his cock buried to the base inside me. My body shook, overwhelmed by the weight and fullness.
“Fuck…” I whimpered, muffled by the sheets.
Greg leaned down, his mouth at my ear again. “You’re taking me so good. Can you feel it? All of me inside you?”
I nodded frantically, my hole clenching around him.
“Shit—don’t squeeze like that,” he groaned, his hands tightening on my hips. “You’ll make me cum already.”
I moaned louder, my ass flexing again just to hear his reaction.
Greg laughed breathlessly, smacking my ass once, firm but playful. “Little tease. You like hearing me lose it, huh?”
My face burned, but I couldn’t deny it. “Y-yeah.”
He kissed the side of my neck again. “Good boy.”
Then he pulled back…slow, dragging his cock out inch by inch until only the tip stretched me, then drove back in just as slow.
The sound that left me was half moan, half cry. My hole clamped down around him, my body rocking forward into the sheets.
Greg groaned, his voice sharp. “Fuck. You feel unreal, Alex. Wet, tight….”
I whined into the pillow, my own cock straining hard against the sheets, leaking precum onto my stomach.
He thrust again, still slow, letting me feel every inch slide in and out. The wet sounds filled the room, mixing with our ragged breathing.
“You doing okay?” Greg asked between thrusts.
“Yes…” I gasped, my voice breaking. “…Yes, Mr. Lawson.”
He groaned deep, kissing the back of my neck again. “Good. ’Cause I wanna fuck you, Alex. I’ve been starving for this. And your ass…” He slammed in a little harder, making me cry out. “…your ass feels better than anything I’ve ever had.”
I moaned, my body jerking forward, but his grip on my hips held me steady.
“You want me to go harder?” he asked, his voice low and rough.
My head shot up from the sheets, hair plastered to my face with sweat. “Yes. Please.”
Greg growled, pulling almost all the way out, then thrusting back in harder, the slap of his hips echoing in the room.
“Fuck!” I yelped, gripping the sheets.
“That’s it.. You’re doing so fucking good Alex,” Greg said, his voice sharp but steady. “Take it.. This cock—” He slammed in again, making me moan loud. “—is yours.”
The rhythm built, slow at first, then deeper, harder, his balls smacking my ass with every thrust. The burn turned into heat, the stretch turning into something filthy and addictive.
My hole clenched around him, milking his cock as he pounded me steady.
Greg’s breathing grew heavier, his body slick with sweat against mine. “Jesus Christ. First time fucking a guy… and it’s you.” He spanked me again, his palm echoing on my ass. “You like that?”
“Yes!” I moaned, my voice breaking. “Fuck, yes sir!”
His thrusts picked up, pounding harder now, every inch filling me, every stroke deeper than the last. My cock leaked all over the sheets, untouched, dripping precum with every thrust.
Greg’s hand slid up my spine, pressing me into the mattress as he fucked me, his other hand gripping my hip like he’d never let go.
“Sound so good, Alex,” he growled. “Moaning like that. You’re making me lose my fucking mind.”
I gasped, my ass clenching tighter around him.
“Don’t squeeze… arrghhh…fuck!” he groaned, his thrusts stuttering for a moment. “You’re gonna make me cum if you keep doing that.”
I whimpered, my voice high and broken. “Don’t stop.”
Greg leaned down again, pressing his mouth to my ear. “Don’t worry. I’m not stopping. Not until you tell me to.”
His hips slammed into me, harder now, driving his cock deep into my ass over and over. The room filled with the sounds of our bodies colliding, the wet slap of his cock inside me, our moans and groans mixing into one filthy rhythm.
“Goddamn boy,” Greg growled, teeth grazing my neck. “I missed this. Fucking someone. You’re doing so fucking good, Alex.”
I moaned so loud it broke into a cry. My body was wrecked, shaking, but I didn’t want it to end.
Greg’s thrusts grew sharper, his breathing ragged. “Feel so fucking good… I don’t know how long I can hold it.”
I dug my nails into the sheets, head pressed against the pillow, my voice cracking as I gasped, “Then don’t hold back Greg.”
That made him freeze for a split second, shocked, his cock buried deep inside me. His eyes flicked down, wide, chest heaving, like he couldn’t believe I’d just said that.
“Alex…” his voice broke, rough with restraint.
“Please,” I begged, tilting my hips back against him, feeling the thick length of him straining inside my ass. “Don’t hold back. I want it.”
That was it. Something in him snapped. He gritted his teeth and slammed forward, cock spearing into me with a sound so filthy I nearly screamed. His hand clamped tight on my hip, the slap of his body against mine echoing in the quiet room.
“Fuck—” Greg growled, rutting into me, his thrusts heavy, merciless now. “You’re so fucking tight… fucking hell…”
My moans spilled out, shameless, high-pitched, my body taking every deep stroke. “Ahhh—ahh, fuck, Mr. Lawson—fuck!”
His grip shifted, one hand pressing on my back, adjusting me down into the mattress while he pounded me from behind. The air punched out of my lungs with each thrust. He was sweating, dripping onto me, the bed groaning beneath us.
And then, with a strangled laugh, he muttered against my neck, almost shocked at himself, “Fuck…I forgot…I don’t really have to pull out with you.”
The words shot straight through me. I clenched around him hard, groaning into the pillow.
Greg swore, hips smacking into me faster, desperate. “Shit, Alex—shit—I’m gonna cum, I can’t—fuck, I can’t stop—”
“Yes! Yes…fuck m…—don’t stop, please, Mr. Lawson—ahh, fuck—”
He slammed deep, his cock throbbing inside me, and then I felt it…thick, hot cum spilling, pulsing into my ass.
Greg’s whole body shuddered as he groaned, long and guttural, collapsing forward slightly, grinding his cock into me as the last spurts spilled out. “Ohhh fuuuck…”
I moaned, my face buried in the sheets, feeling the wet heat of him filling me. The weight of his body pressed me down, his cock jerking inside me as the last drops leaked out.
For a moment, neither of us moved. Just his heavy breathing above me, the sticky warmth spreading inside me, dripping out around his cock.
Finally, Greg pulled out with a wet sound. I gasped, empty suddenly, my hole clenching at the loss. He smirked, standing over me, and tapped his softening cock against my messy, stretched hole, leaving streaks of cum across my ass.
“Jesus Alex…” he muttered, running a hand through his sweaty hair.
I collapsed flat onto the bed… my legs trembling. My chest heaved as I tried to catch my breath.
Greg stood there, sweat dripping down his abs, his cock hanging heavy, a bead of cum sliding off the tip. He looked like a fucking god.
“So…” he said finally, his voice low but playful. “How was it?”
I turned my head toward him, my lips curving into a weak, blissed-out smile. “Better than expected.” My voice was hoarse, shaky.
He chuckled, still watching me with that mix of pride and disbelief.
I hesitated, staring at his body, his muscles gleaming with sweat, the outline of his cock still thick even soft. My throat went dry as I asked, “And… how was it for you?”
Greg smirked, his eyes dark, and took a step closer. A string of cum dripped from his tip, landing on the floor between us.
“So much better,” he said, almost laughing under his breath, “when the person you’re fucking is actually into it.” His smile lingered, softer now, like he couldn’t quite hide it.
Then he bent, grabbed a towel off the chair, and slung it over his shoulder. “I’ll go shower now.”
He gave me one last look, his eyes warm, before walking out.
I stayed there on his bed, still spread out, body aching, hole dripping with his cum. My smile grew wider without me meaning it to. My boss had just fucked me and it was better than anything I’d ever imagined.
And I wasn’t sure if I’d ever want to stop.
If you enjoyed this story, consider supporting the author on Patreon.
