Evaluations and proposals.

Ashley showed up in my office after exactly a half-hour, presumably done with the busywork I had assigned her, and also looking remarkably well-composed considering the corrective measures she had already received tonight. She bowed politely upon entering then stood just opposite my desk, waiting for me to address her.

“Well, Ashley, that’s your first day. I trust you didn’t run into any more problems?”

Ashley blushed again, but shook her head, “No sir, everything was very clear, and I learned some valuable lessons.”

I nodded. “That’s what I like to hear. I’m a very busy man, and I expect the most out of my employees.”

Ashley smiled and stepped closer, “I’m always willing to go the extra mile, sir. Would you like me to rub your shoulders?”

I nodded again, and Ashley quickly took her place behind my chair, her slender hands finding purchase on my shoulders. As she eased the tension, I collected a blank piece of paper from the desk. On it, I scribbled a few numbers and notes. I enjoyed Ashley’s shoulder rub for a couple more minutes, before standing up and stepping away from my desk.

“Come around here and give this a look, Ashley.”

Ashley gave an excited “Yes sir!” before scurrying around and squeezing into the space between me and my desk, making sure to push her shapely ass back against my crotch as she bent over to read the paper.

“It’s an evaluation of your work thus far. As you can see, you have great potential,” I reached down and rubbed Ashley’s thigh just below the line of her skirt. “If you’re willing to take on a few additional responsibilities, join me on some training retreats, and show up for a few after-hours meetings,” I moved my hand up, pushing Ashley’s skirt up with it and revealing her bare nethers, “I think we’ll enjoy a long and pleasurable working relationship. How does that sound, Ashley?”

“I don’t know, sir,” Ashley said, her feet slowly moving in opposite directions, “It sounds like a lot of responsibility to take on so soon.”

“Well, the choice is yours, Ashley,” I explained, a hand slipping down so I could tease her labia from behind, “But it’s clear that you enjoy working beneath me.”

“Mmmm,” Ashley moaned, wiggling her hips in response to my hand, “I love working beneath you, sir. But these late-night meetings seem like a bit much, don’t they?”

“I’m a very busy man, Ashley. My need for an assistant doesn’t disappear once the sun goes down.” My middle finger had found her clit, and I began to tease it, “There may be nights where you don’t make it home at all.”

Ashley’s breath hitched in her throat and she leaned down further, her elbows braced against the desk. “Ah, uh, you’re right, sir. But, oh, isn’t that, uh, why you hired a maaaaiiiid?” Ashley’s head drooped as my dextrous manipulations started to wear away at her focus.

“A maid?” I asked, temporarily slowing my handiwork. This was the first I had heard about any maid.

“Yes, sir,” She said, looking back at me with a strained smile, “I think you said her name was Ashley?”

“What a coincidence.” i withdrew my hand completely and unzipped my pants.

“I can take care of whatever you need tonight, sir, but I believe your maid starts tomorrow.”

Ashley clearly was enjoying these submissive games more than I had anticipated, but I wasn’t in a position to complain. “Very well, Ashley,” I said, placing a hand on her upper back. “Shall we get back to work, then?”

“Please, sir.”

I applied pressure, and Ashley’s arms gave out as her upper body was pressed into my desk, likely scattering or wrinkling any theoretically important papers. With her properly pinned down, I finally aligned my cock with her sweating pussy and pressed forward. No matter how many times I’d been inside her before, Ashley’s pussy never lost it’s magic. Tight and warm and hungry, it accepted my length easily. I didn’t waste time by starting slow, immediately setting to work with hard, deep thrusts that squished her against the desk each time.

“Thank you sir!” Ashley squeakily whispered, “Ah! Yes!”

“You know, Ashley,” I grunted, “We’re the only people in the building. You don’t have to hold back.”

“Oh!” She squeaked again, louder this time, “Sorry, sir! Fuck!”

Ashley’s cries slowly grew in volume as I continued fucking her into the desk, until she was screaming long, drawn out syllables as she desperately tried to withhold her climax. She knew, of course, that I was planning to align our climaxes, and while her muscles clenched around me on every thrust, she managed to keep from coming until I could no longer do the same.

“Shit, Ashley, I’m-”

“Me too, sir. Ah!”

Speaking had broken the spell of concentration that had kept our orgasms at bay, and we came in unison. My orgasm felt in no way diminished by our earlier session that night, and Ashley’s, if anything, seemed more intense, her arms twitching uselessly by her side as she let out a long, low moan. I collapsed forwards, my hands braced near hers on the desk to support my weight. After recovering somewhat, i wrapped my arms around her and sat backwards, pulling her with me into my chair.

“Rutabaga,” Ashley panted out, leaning her head back on my shoulder. “That was good.”

“Yeah, it was,” I agreed, looking down to meet her inverted gaze, “Were you serious about that maid line, though?”

Ashley grinned, “Of course, sir. I’ve been looking for an excuse to dig out that costume again, anyway.”

“Sir?” I asked, raising an eyebrow, “I thought the game was over.”

Ashley rolled her eyes, “Ugh, please just shut up and take me to bed.”

I gave her a kiss, and then did just that.