Temporary Arrangement with Mr. Greg | EP 5: Don’t Be Shy

This fictional story features only adult characters (18+) and portrays consensual interactions throughout.

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“What? Like seeing your boss’s bulge?”  Greg chuckled, shaking his head.

The words hung in the air, half a tease, half a challenge. My throat tightened.

“I didn’t Greg,” I stammered. “I didn’t mean that —”

Greg’s lips curved, slow and knowing. His hand was still resting casually over the swell in his sweatpants, stroking his fingers across the fabric as if it were nothing, as if this were just another late-night conversation between us.

“It’s okay,” he said, voice low. “Don’t be shy. I saw you looking at me in the kitchen this morning too. When I was in just a towel.”

My heart thumped. I tried to swallow the heat in my face. “Uh… sir. Mr. Lawson. I’m sorry. I didn’t mean—”

His other hand shifted, brushing against my thigh, barely there but enough to make my cock twitch inside my shorts.

“No, no. It’s okay.” His tone softened, almost reassuring. “I don’t mind it.”

The words settled inside me like permission. My eyes flickered downward before I could stop myself. The bulge in his sweats had grown, pushing forward, stretching the fabric tighter. His fingers rubbed over it lazily, and it seemed to swell under his own touch.

He caught me staring again.

“You want to touch?” Greg asked.

My stomach clenched. I froze, caught between instinct and reason.

“I - I mean…”

But my hand was already moving, as if it belonged to someone else, hovering uncertainly before landing on the warmth of his thigh. The muscle under my palm was hard, solid. My fingers flexed against it, feeling the strength there.

Greg didn’t move away.

“Go on,” he murmured. “I’m your boss in the office. But here…” He paused, his lips quirking. “…here, I’m just your mate.”

The word lingered, heavier than it should have.

I exhaled slowly, then slid my hand higher, the soft fabric of his sweats dragging beneath my palm until I pressed against the firm weight straining behind it. My hand trembled as I gave the gentlest squeeze, and Greg let out a quiet sound, almost a hum, like approval.

“Yeah,” he breathed. “Just like that.”

My pulse was a drum in my ears. I wrapped my fingers around him, feeling the shape of his cock through the thin cotton…thick, heavy, filling my grip more than I expected. I stroked slowly, testing, and the bulge twitched under my touch, growing harder with each movement.

“Fuck Alexx,” Greg muttered, eyes half-lidded. “That feels good.”

He reached down then, his hand brushing mine away for a moment. My chest tightened, thinking I’d crossed too far, but instead he tugged at the waistband of his sweats. With one smooth motion, he pulled them down to his thighs.

He wasn’t wearing any underwear.

His cock sprang free, thick and flushed, curving slightly upward as it slapped against his stomach before settling heavy over his lap. The sight punched the air from my lungs.

The shaft was long, at least eight inches, cut clean, veins running along the sides. His tip was swollen and slippery with precum already, shining in the dim light. Dark, wiry pubes framed the base, thick but trimmed just enough to look deliberate.

I couldn’t stop staring.

I’d imagined it, sure. Ever since that night I’d caught him jerking off. But seeing it this close…seeing the reality was different. His cock wasn’t just big. It was perfect in that raw, masculine way. Heavy, proud, made to be gripped and worshiped.

Greg caught the look on my face and smirked, leaning back on one hand. “Bigger than you thought?”

The words slipped out before I could stop them. “Uh… yeah.”

I froze. My brain caught up a second later, realizing I’d basically admitted I’d been thinking about my boss’s cock. “I mean…I wasn’t… I didn’t mean…”

Greg’s smirk deepened. “How about we stop pretending you haven’t had a crush on me since forever?”

My eyes flicked up to him, shame burning hot in my chest. “Mr. Lawson…”

“Alex,” he said slowly, steady, like he’d been waiting for this. “You think I don’t know?”

His hand slid down, holding his cock in his hand as he kept talking. My gaze followed helplessly.

“All those meetings,” he murmured, fingers tracing himself lazily, “you’d sit across the table, eyes stuck on me instead of your notes. I’d stand at the board and you’d get that glassy look, like you were somewhere else entirely. And don’t tell me you never checked me out when I leaned over your desk.”

“I —I’m sorry,” I whispered.

“Oh, don’t be.” His tone was light, but his palm grip tightened around his cock… “When someone looks at you the way you do…” He slapped his thick cock against his palm once, a wet sound cutting the air. A smear of precum shone across his skin when he pulled his hand away. “It feels good.”

My breath caught. My eyes locked on the head of his cock, flushed and leaking.

“So,” Greg said, voice lower now. “Do you wanna keep looking, or do you wanna touch?”

I shifted closer without meaning to, body leaning toward him like gravity was pulling me down. “I… I—”

His fingers caught mine, steady and sure, guiding my hand forward. I hesitated in the air, then finally wrapped around the base of him. The heat hit me first. Alive, thick, pulsing in my palm. My fingers didn’t even close all the way, he was too big. Too much.

I gave a slow stroke, dragging my hand up the length until my thumb brushed his dripping  tip. Precum smeared across my skin, sticky and hot.

Greg let out a low groan, his head tipping back for a moment. “Shit. That’s it, boy.”

I couldn’t stop now. I stroked again, then again, each movement more confident than the last. The precum leaked steadily, dripping down over my fingers, making everything slippery. My breaths grew shallow, my cock twitched in my shorts as I stroked him.

“Come closer,” Greg said suddenly, his voice rough.

I shifted on the bed, moving lower, closer between his spread thighs. My knees pressed against the mattress, my chest nearly against his side. From here, I could smell him; the mix of beer, sweat and something darker, muskier.. manlier...

My hand kept moving, pumping him slowly, twisting at the tip. His cock throbbed in my grip, leaving trails of precum over my knuckles, dripping down to stain his sweatpants where they bunched around his thighs.

“Fuck, Alex,” Greg muttered, watching my hand on him. “You’re good at that.”

“Fuck, Mr. Lawson…” The words slipped out before I could catch them.

Greg’s eyes snapped open, amused, hazy with lust. “Uh… do you wanna…?”

He didn’t finish the sentence. He didn’t have to. His eyes flicked down toward his cock, then back to me, questioning, waiting.

My lips parted. My throat felt dry. Every nerve in my body screamed yes, but the weight of what we were doing pressed down on me. I stroked him again, slower this time, my hand gliding over the thick shaft, thumb brushing across the swollen head. Precum smeared across my skin, warm and slippery.

Greg’s breath hitched, his hips twitching upward into my grip.

I looked up at him, caught in his gaze. His face was tense, flushed, his jaw clenched as if holding back.

“Do you wanna.... maybe ....taste it?” he asked again, quieter this time, almost gentle.

The silence stretched between us, heavy with the choice. My hand never stopped stroking him, precum dripping steadily onto my fingers, sticky and slick.

And I knew, in that moment, I’d already made my decision.

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