Page 19 of The Boss


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“Thanks. Later, Leo.” I ended the call, tossing my phone on the island and staring blankly at the fridge. I should make dinner and decompress with a good book and a hot bath before bed. My day would start early tomorrow, and while I wasn’t worried about starting my new job, being well rested would make the first day go more smoothly.

Or, I could text the sisters and see if Charlotte was available for a last minute play session.

I picked up my phone and sent the text before opening the fridge and studying the contents. I grabbed a beer and made a quick sandwich from leftover roast beef, adding some raw veggies to a plate with hummus before sitting at the island to eat. After nearly two days of listening to my parents’ constant badgering, the silence of my home was a welcome relief. I scrolled through Facebook as I ate my sandwich and veggies.

Twenty minutes later, as I was scraping the final carrot through the last dredges of hummus, my phone dinged with an incoming text. Excitement and trepidation mixed in my belly, and I opened the message from the sisters.

A wide grin crossed my face. Charlotte was available for a play session, and she’d be here in half an hour.

* * *

It was quiet enough in the house to hear the front door opening. My stomach tensed, and I had to work hard to keep my body still and calm. Charlotte was light-footed, but I still heard the creak of the second stair from the top and the click of the bathroom door as it shut.

I grinned. Her refusal to drive without underwear or a bra was cute as hell. I sucked in a deep breath, more nervous than I usually was during a play session.

Maybe because of how quickly you lost control at the last one?

I grimaced. I had lost control, and the urge to take things further was tough to deny. Knowing that Charlotte wanted it had only made it more difficult. I’d only meant to kiss her, to test her reaction and confirm she wasn’t afraid of me. Her desire was immediately obvious, and the taste of her lips, her soft moans, and her magnificent breasts had nearly wiped out my self-control. The way she’d rubbed her little pussy against my leg, looking for her pleasure… fuck, what it had done to me.

If my alarm hadn’t gone off, reminding me our playtime was over, I would have undoubtedly touched her soft cunt, and made her come all over my fingers until she moaned my name. I couldn’t even say goodbye at the last play session. I’d stayed right where I was at the coffee station until I heard the front door close. Then I’d gone straight upstairs and jerked myself off to the memory of Charlotte’s kisses and her lush body rubbing against mine.

My dick was already hard as a rock, and I adjusted myself roughly before scanning my office. The play scene was set and ready to go. I had a document on Charlotte’s desk for her to type. It was just an old contract I’d printed off the internet, but I hadn’t had much time to prepare.

My gaze drifted to the filing cabinet. A stack of file folders sat on the floor beside it. I’d gone through the cabinet and pulled a bunch, mixing them up and stacking them on the floor. They were all dummy files with fake names, and most contained only one or two sheets of plain paper, but it worked well as another ‘job’ Charlotte could do while she was here. And as a bonus, I’d get to see plenty of her plump ass as she bent to do the filing.

I heard Charlotte’s footsteps in the hallway, and I quickly stared at my laptop, deliberately not looking up or acknowledging her when she entered the room. I checked my email and even managed to reply to one or two while keeping Charlotte waiting on her knees for nearly five minutes.

Normally, I would make her wait fifteen minutes. It was a good test, especially for those new to this type of play, but my own enthusiasm wouldn’t let me wait a second past five minutes. I looked up, pride washing over me when I saw Charlotte kneeling on the cushion exactly as I had instructed. My girl was doing so well already.

I studied her closely. Her dark hair had been straight and sleek the last time she was here. This time, it was a delightful mass of curls piled on top of her head, with a few stray curls framing her face.

My clothes were casual tonight - a Polo shirt and jeans, but she wore business attire. The scoop neckline of her pink top showed off her tits and the fabric hugged the curve of her stomach. My dick pressed against my jeans as I imagined pulling the neckline down so I could feast on her perfect naked breasts.

She’d paired the top with a dark gray pencil skirt and stockings. I itched to run my hand over the smooth skin of her legs. I should have told her to lose the nylons as well.

So, you’re planning on doing more than just kissing tonight?

I stood. Why shouldn’t I? Why wouldn't I reward Charlotte if she was a good girl tonight?

Some men looking for a woman to be their good girl believed punishment and being strict were the keys to success. They were wrong. If they found a woman who blossomed under that type of guidance, then the woman didn’t have a praise kink, at least not the praise kink I was looking for.

I might crave a woman’s obedience, but I wanted her to give it because it made her happy and because being my good girl fulfilled a need for her, not because she was looking for punishment. It’s why I didn’t care for brats. While I had no problem being stern and even doling out the occasional spanking if necessary, ensuring she knew how special she was, how happy she made me, and giving her the praise she craved were the real keys to success.

I stood and crossed the office to stand in front of Charlotte. She kept her head bowed and her hands in her lap, but her fingers tapped against each other, clearly showing her nervousness.

“Good evening, Charlotte.”

“Good evening, Mr. Steele.” Her voice was as soft and sexy as I’d remembered.

“You’ve followed my instructions very well,” I said.

She smiled happily at me. “Thank you, sir.”

“You’ll find a document to be typed at your desk,” I said.

“Yes, sir.” She stood, and I watched the sway of her perfect ass as she walked to her desk. I returned to mine, watching surreptitiously as Charlotte started to work.

She squinted at the screen and the document, and I said, “Charlotte if you usually wear glasses for reading, you should wear them when you’re here.”

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