My new arrogant boss is someone I know - Chapter 5 (Patreon)

All characters are consenting adults (18+). All sexual acts depicted are consensual between the adult characters

Chapter 5

Calum told me at four in the afternoon of a Friday.

He didn’t look up from his screen when I stepped into his office. He just spoke while signing something.

“You’re coming with me tonight. Private dinner. Two investors. Wear the dark suit. No underwear. And put this in before we leave.”

He opened the top drawer and slid a black silicone plug across the desk. It was thick. Heavy. Demanding.

“Go to the bathroom. Put it in. Then wait for me in the lobby at seven.”

I did as I was told.

The plug stretched me open the moment it seated inside. Walking back to my desk already felt different — every step reminded me it was there, thick and unyielding. By the time seven came, my cock was half-hard just from the constant pressure.

Calum met me in the lobby wearing a charcoal suit and that same cold, unreadable expression. He looked me over once, eyes lingering on the way I stood a little too carefully, then gave a short nod.

“Car’s outside.”

The restaurant was the kind of place that didn’t put prices on the menu. Private dining room on the top floor, city lights stretched out beyond the glass, thick carpet that swallowed the sound of our footsteps. Two men were already seated when we arrived — both in their forties, expensive watches, the relaxed confidence of people who never heard the word no.

Calum introduced me only as “my social assistant.”

I sat to his right. The plug shifted inside me every time I moved. I kept my back straight and my eyes down the way he had trained me.

Dinner started normally. Wine. Small talk about markets and projections. Calum was sharp, controlled, charming in that distant way of his. I barely spoke. Every few minutes the plug pressed against something sensitive and I had to breathe carefully through my nose. I ate everything Calum chose for me.

Halfway through the main course Calum set his glass down and looked at me.

“Go to the restroom.”

It wasn’t a suggestion.

I stood, feeling both investors’ eyes on me for a second, and walked out of the private room. The hallway was quiet. I locked myself in a stall, hands shaking slightly, and waited exactly three minutes the way I knew he expected. When I returned, Calum didn’t look at me. He simply slid his chair back a few inches and tapped two fingers against his thigh under the table.

The signal.

I dropped to my knees on the thick carpet and crawled under the long table.

The space was tighter than the conference rooms at the office. I settled between Calum’s legs. He had already unzipped. His cock was heavy and slightly sweat from the working day when I took it into my mouth. Above me the conversation continued without a single pause.

“As I was saying,” Calum said calmly, “the projected return over the next six quarters is conservative.”

I sealed my lips around him and started sucking slowly, carefully, keeping every sound as quiet as possible. The plug inside me felt enormous in this position. My own cock strained against the fabric of my suit pants.

One of the investors chuckled at something. A glass clinked. Cutlery moved against plates.

Calum’s hand came down and rested on the back of my head — not forcing, just reminding me he could. I took him deeper, letting the thick head push into my throat. His thighs tensed once, then relaxed again. His voice never changed.

“The risk profile is lower than the previous structure we discussed.”

I worked him with long, wet strokes, spit starting to gather at the corners of my mouth. The carpet dug into my knees, at least it was comfortable. Above me the two men kept eating and talking as if nothing unusual was happening three feet below their plates.

Calum shifted slightly in his chair, spreading his legs wider. His hand pressed more firmly, guiding me all the way down until my nose brushed the fabric of his open pants. I held myself there, throat fluttering around him, eyes watering. When he finally let me up for air it was only for a second before he pushed me back down again.

“I think you’ll find the terms more than reasonable,” he continued, voice perfectly even.

I sucked him harder. The wet sound of it stayed trapped under the tablecloth. My jaw ached. The plug felt like it was splitting me open every time I moved. One of the investors asked a question about timelines. Calum answered without a single hitch in his breath, even as I took him into my throat again and again.

After a while his hand tightened in my hair. His cock swelled heavier against my tongue. I felt the first warning pulse and stayed down, swallowing around him the way he had taught me.

He came in near silence.

Only the faintest tension in his thighs and a short, controlled breath through his nose gave it away. Thick, hot pulses flooded my throat in heavy spurts. I swallowed every one, eyes streaming, nose pressed tight against him until he finished. Even then he kept me there for several extra seconds before slowly pulling me off by the hair.

I stayed on my knees under the table, breathing hard through my mouth, chin wet, the thick taste of his cum on my tongue. Above me Calum calmly reached for his wine glass.

“I believe that covers the main points,” he said. “Shall we move on to the paperwork?”

Chairs shifted. The two men agreed. I heard the soft sound of Calum zipping his pants. His hand came down once more, two fingers tapping the back of my neck — the signal to stay.

I stayed.

They talked for another twenty minutes about contracts and signatures while I remained under the table on my knees, plug still buried inside me, cum still sliding down my throat, listening to the ordinary sounds of a business dinner. When the men finally stood and shook hands, Calum’s shoe nudged my knee.

“Stand up.”

I rose from the floor on slightly unsteady legs. The plug shifted heavily inside me. Both investors watched in silence as Calum’s voice stayed perfectly calm.

“Turn around. Lower your pants.”

My hands moved before I could think. I unbuttoned, pushed the trousers and underwear down to mid-thigh, and bent forward slightly when he gave a short nod. 

The thick base of the plug was clearly visible between my cheeks, stretching me open. Cool air touched the stretched rim of my hole.

Calum’s tone didn’t change at all.

“This is part of the goodwill I mentioned earlier. Now that the contracts are signed, you’ll have access to my personal assistant whenever you’re in the city. He’s trained, discreet, and available. Consider it a practical benefit of the partnership.”

One of the men let out a low, appreciative breath. The other simply stared. Calum reached out, gripped the base of the plug, and turned it slowly inside me so they could see exactly how open I was.

“He doesn’t speak unless told to. He doesn’t refuse. And he cleans up after himself.”

He released the plug and gave my hip a short, dismissive push.

“Pull them up. Sit down.”

I did, face burning, the thick silicone still forcing me wide while the two investors looked at me with new, open interest. Calum had already returned to his wine as if nothing unusual had just happened.

After a few minutes the investors left.

“You held still. Good.” Calum said to me.

“Thanks, Mr. Calum.”

He adjusted his cuffs, picked up his phone, and already started toward the door.

“There’s a car downstairs. It will take you home. Be at the office at eight next Monday. And leave the plug in until I tell you otherwise. I’ll send you a text when you’re allowed to.”

He walked out without waiting for an answer.

I stood alone in the private dining room for a moment longer, suit wrinkled, mouth tasting of him, the thick plug still forcing me open with every breath.

Then I followed.

The car was already waiting at the curb.

I sat in the back seat with my hands on my thighs, the city lights moving past the window, and the clear knowledge that next week he would use me again…

What my best friend would think if he knew what his father is doing to me?

Shit…