Then Beg For It |18+

2| O

Kathleen

The elevator doors slid open and Simon was already pointing in the direction of Roman's office by the time I came into view. I chuckled, "Good morning Simon."

He smiled, "Great morning it will be Kathleen." I had my talk with Roman the previous morning and we were all clear with how he wanted to be treated. I've only dominated men a few times down the line; I had a stomach and an aching want for it. I was sure about Roman, there was something in his eyes when he shook my hand the first time we met. He needed it.

I opened the doors and Roman jumped a bit from his seat at the sight of me. I smiled, "Nervous?" We had agreed to try something out, I was hiding it in my bag.

"How'd you sleep?" I came over slowly, "I was up all night thinking about today, could barely sleep."

I set my bag down on the chair, "Yeah?" It made me excited to think of him tossing and turning in his bed. He was willing, he was desperate for it. "Good."

"The workers come in at ten." I imagined him hanging from ropes naked, a ball gag deep in his throat. "The room is sound proof, been that way for a while."

I stood up and he jolted slightly in his seat once again. I smiled biting my bottom lip, "Calm down." I walked over to his seat behind the desk, "It won't hurt bad." I spun his chair around so that it faced me, "Roman?"

"Yes Miss?" Miss. That means the start of our fun.

I put my hand on his chest and bunched his dress shirt in my hand pulling him towards me. I could smell the sweet hard scent of his cologne. I licked the bottom of his lip, "Go lay down on the desk, and make sure that your ass is bare and visible for me to play with."

I stared up at him waiting for an answer, "Yes Miss."

I pulled at the belt holes of his pants and I could feel his breaths stutter on my nose, "Never make me wait." I bit down on my bottom lip, "Because I get angry."

He nodded, "Yes Miss." I let him go and he walked over to the desk, unbuttoning his pants as he did so. He pulled his pants down and his chiseled ass cheeks came into view. He laid down on the brown desk, his head turned to the right away from me. I took a step towards my bag and he shook a bit, oh gosh.

"Didn't I say to calm down?" I unzipped my bag and took out one of the wooden paddles I had. I laid it on the desk and took out a bejeweled paddle second. I picked up both and stood behind him, "Roman?"

I could see his ass cheeks clench at the sound of my voice and my presence behind him, "Yes Miss?"

I smirked, "Tell me which one hurts more." I gripped the handles of the paddles as I struck them down on his behind. He gasped in pain and I could see red slowly spread across his white bottom. "Hmmm?"

He didn't say anything and I landed the paddles on his ass once again. "The right one!" He yelled out and I squeezed my thighs together at his pained cry. He groaned softly, "The right one Miss."

I twirled the bejeweled paddle in my right hand, "Do you like it, or should I stop?"

"I like it Miss." I placed the bejeweled paddle on his left cheek and he jumped slightly at its touch, "I want to be punished for being the naughty boy that I am."

I bit down on my bottom lip, "You're a naughty boy?" I slapped his left cheek with the paddle, and I could see the slight indents of the jewels on his ass. He let out a small grunt and I leaned over to his ear, "I'm going to have my ways with you then..." I put a hand on his ass and began to massage it, "I love a naughty boy."

I licked his ear and slapped his bottom with my bare hand. He moaned, "Harder Miss." Fuck he was a wild one, and I loved the opportunities that want would bring to our sessions. "Can I touch myself?"

The pain had to be pushing so much pleasure to his dick, I wanted to have him hurting even more. "No." I slapped the bejeweled paddle against his ass harder, "Why would I let you enjoy your punishment?"

He moaned, "Please Miss..." I could see his hands slowly slip off the desk and towards his front side. I put the paddle under my arm and grabbed both of his hands, holding it behind his back. I struck the bejeweled paddle across his entire behind, "Fuck..."

"You tried to touch yourself despite being told not to." I took off my underwear and used it to keep his hands restrained behind him. I pulled him up and turned him around to face me. His dick was long and hard, close to touching my own stomach as it protruded.

I gripped the paddle in my hand harder at the sight, a heavy heat settling between my thighs. I pushed him back on the desk and he winced as his ass hit the table. He instinctively went to get up and I held him down by his shoulder, "Sit." Pain scattered across his face and his jaw clenched. I shrugged, "Next time you listen."

I set the bejeweled paddle down and began to unbutton his dress shirt. I stared into his eyes as I did and brought my body closer to his. His dick easily slipped under my bunched up skirt, hovering below my aching front side. I opened up his shirt and ran my hands down his chest, my fingers playing with his nipples. I tugged on them and he groaned, biting his full pink lips, "I'm sorry Miss."

"You should be." I went for my bag and tugged out a chain with pinchers at the ends. I opened up the clamps and brought them to his chest, "This time you'll learn." I let them shut over his nipple and he let out a heavy scream. He sucked air through his teeth and I watched as his eyes shut, his muscles tensed.

I smiled and stepped back a bit, his chest rising and sinking quickly, "How does that feel Mr. Sterling?"

His dick was still fully erect, "Amazing..."

I put my fingers in his mouth letting him gag on them a little. I slowly pulled them out, spit trailing out of his mouth, sticky on my fingers, "What do you say?"

"Thank you Miss."

——

End of Chapter Two.