Spanking Boss Novels & Stories

’ “BOSS! I GOT THE CRAZY OLD MAN!” The bald man was really annoyed and his vicious gaze landed on his subordinate. “Why did you bring him? Do you want me to do your job?” He huffed. “No, boss. I apologize.” The thug subordinate pushed the crazy old man in front of the bald man. This was his time to show off that he was fierce and deserved to be promoted. He stepped on the old man’s chest and loudly asked. “Do you know this lady?” The bald man took off the other pair of his shoes and hit the subordinate’s leg a few times. “What b-llsh-t are you doing? Get your legs off the old man!”

And, I bet that it's more than a hundred words. This is just so effin' great! A bossy, perfectionist, arrogant, and a bit of a jerk for a boss... I'm gonna be enjoying this for sure. Damn!

It’s a bit of an adventure. He stood up slowly. I felt the thick head of his mature cock rub against my soaked entrance, teasing. He slid it up and down my slit, coating himself in my juices and the mess he’d just cleaned. “Please…” I whispered brokenly. My boss chuckled softly. “I am going to fuck the hell of you today. You’ll definitely work for every penny of the payment you received.” He pushed into me much faster in a single forceful thrust than any of the men ever had.

This time, I know damn well that I feel her squirm against me, and I know damn well that I can feel a heat against my thigh where her little pussy is pressing into me. “You wanna sass me, princess? You want to knock me over the head and run off and see how far you get before they find you? Well, it’s not gonna fucking happen. So in this cabin? Yeah, you’re damn right I’m the boss of you,” I growl, spanking her ass once more and relishing the whimper and the barely contained moan that drips from her lips. She’s fucking loving this, even if she’s trying her hardest to pretend she isn’t.

"Bend over, kitten." I leaned over the cold wood, my ass up, cheeks burning with shame and excitement. His hand cracked down on my right cheek, a sharp spank that stung. I yelped, but he did it again on the left. "Quiet," he whispered, his breath hot on my ear. "This is for being such a tease in those tight skirts." He spanked harder, alternating sides, each hit building heat in my skin. As he did, he leaned in, whispering dirty things. "You like this, don't you? Your pussy's getting wet for your boss. Imagine my cock inside you, stretching that virgin hole."

"I don't have any patience for this shit show.” Macey rolled her eyes, clearly Pauline wasn't getting the hint. "Hello, boss. Pauline, meet Mr Chad Steele, I and Olivia's boss,” she said. “Are you kidding me? Boss?” Pauline laughed loudly, "Even after work hours, what sort of psychotic madman does that?" she challenged. Turning to her with a sneer, "What I do with her is not your business, over dressed little thing,” Chad spat. Pauline's eyes widened and she slammed the table. "How dare you?! How dare you try to ruin our night, you pompous prick, why should Olivia listen to you when she's not working tonight, huh?” She asked and pointed at him.

She stops at the head of the table. “Good day gentleman. You can all stand up. The Boss will be entering now” she says and her voice sounds familiar but I just cannot place where I have heard it before. The Boss enters the room with a black cloak covering his face. He walks around the room and takes the seat at the head of the table, right below the vent where Lilliana and I are hiding. The Boss places his hands on the arm rests and I notice a ring on his left small- finger. Johnny has told me about these rings, he has one just like it. The rings are a symbol of your position and rank as a Mafia boss. This Boss has the same symbol on his ring that Johhny has. It carries the engraving of a fa

“Don’t stop!” He fucked me like an animal. Deep, powerful strokes that hit every sensitive spot. I came first, my pussy clenching around his cock. My legs shook, and I moaned his name over and over. But he did not slow down. He kept going, spanking me again while he thrust. “You like that, don’t you?” he growled near my ear. “Being bent over your boss’s desk like a dirty girl.” “Yes,” I gasped. “I love it. I’m your slut.”

Just like that, every pleasant feeling disappeared. I straightened in my chair and forced myself to open the next file on my desk. No. Whatever this was, it had to stop. Lucas was my boss, nothing more. And that was exactly how it needed to stay.

Roll your eyes" I can always replace lunch at dinner time. And regarding work, you know I can't leave it, how would I pay for the house? Now it's my turn to roll my eyes. This is a town where, even as a homeowner, you have to pay a monthly fee for always living here. Go town. Wow boss. The whole town is run by one person: the boss of the Russian mafia, or as many call it: The Boos. Few people have seen his face, few people know where he is, and few people know exactly what he does. I don't know what he does with all the money from the townspeople, since being so filthy rich I highly doubt he needs it. But hey, it's not like I'm going to ask. I've told you a thousand times that... "And I have