The Monday Routine

If there’s one thing I have to praise Ashley on, it’s her commitment to her characters. Well, that, her sexy body, and her insatiable sex drive, of course. In any case, Ashley’s willingness to go the extra mile continued to impress me. Shortly after “hiring” her as my “secretary,” Ashley decided that she enjoyed the role so much that she wanted to be able to play it again regularly.

So here I was, on the first Monday evening of a hopeful many, taking a seat at the desk of my home office, waiting for Ashley to arrive. As if on cue, I heard the distant sound of my front door opening and then closing, and I checked my watch. 7:45, a full 15 minutes before the start of her "shift,” a good sign for her first day. A few minutes later, a knock on my office door followed, and at my bidding, Ashley let herself in, a cheerful smile on her face.

“Good morning, sir!” She said, giving a slight bow, before hurrying to my desk and handing me a steaming mug of coffee. I recognized the mug from my own kitchen, but I hadn’t turned on the coffeemaker this evening, which meant she must have transported the hot liquid from her house and simply poured it into one of my mugs upon arrival. I gave the coffee an experimental sip, and found it, unsurprisingly, to be perfect. Not too strong, not too sweet, and not too hot. I personally would have been satisfied with a mug of warm water, but the fact that Ashley both knew how I preferred my coffee, and also went to the lengths necessary to prepare it before heading over spoke quite a bit about how seriously she took her character.

As I thoughtfully sipped at the coffee, I took the time to examine Ashley herself. She was dressed in the same outfit she had worn last time, at least in terms of outerwear. From my seated position I couldn’t tell what she was wearing underneath her blouse and skirt, but since the lingerie she had worn during the interview scene were still in the drawer of the desk in front of me, she had either picked out a new set of undergarments, or she was going without. Ashley subtly posed for me as I examined her, before reaching down to my desk and “accidentally” knocking a pen to the ground.

“Oh! I’m so sorry, sir,” She gasped out in mock worry, before turning around and bending over purposefully to retrieve the pen, incidentally causing her short skirt to ride up, exposing inch after inch of exposed leg, though not quite riding high enough for me to learn what panties, if any, she was sporting. Still, the skirt clung to her well-formed ass wonderfully, and I appreciated the sight as she wiggled in place, spending a little too long before straightening back up and turning around, pen in hand. "I'm so sorry sir, I'm just a bit nervous. It's my first day, and this job means a lot to me."

I gave Ashley a stern look. "Just because it's your first day doesn't mean I'll be taking it easy on you, Ashley." I selected a piece of paper from my desk and held it out to her expectantly. She gingerly accepted it and read the instructions printed there. "Get those documents filed, schedule those appointments, and get back to me when you're done. And Ashley?"

At her name, Ashley looked up to meet my gaze, "Yes, sir?"

"Thank you for the coffee."

Ashley blushed, tilted forward in a slight bow, then turned away and rushed out the door, paper in hand. I didn't actually have any filing I needed done, so the instructions on the paper directed her towards a few minor household chores, as well as a place to be in five minutes.

I did a bit of writing before heading to the "Supply Closet," which was actually just my walk-in pantry, and was pleased to see that Ashley was waiting for me there, wiggling her hips back and forth while pretending to struggle with something on the top shelf.

I closed the door behind me upon entering, sealing us both in the tiny room, and stepped towards Ashley. She pretended not to notice me until my hands found their way to her hips, causing her to freeze in place. "Here's where you snuck off to, Ashley. What are you doing?"

Ashley wiggled in my grasp, trying to turn around, but with my hands on her hips, she found the task difficult and quickly gave up, “Oh my gosh, I’m so sorry, sir, I just came down here to get some paperclips. After I finished filing those documents, I noticed you were running low, so I came down to find some and that took a while, and then when I did find them, they’re on the top shelf and I can’t quite reach and-”

“Enough!” Ashley immediately quit rambling, and hung her head in shame, muttering out a few more quiet apologies, “I’m glad you at least finished with those files, but if you had come to me when you first noticed a problem, I would have told you where the paperclips were, and where the step ladder is, as well.” I reached up past Ashley’s head, making sure to press myself against her back as I did so, and grabbed an arbitrary item from the top shelf, which happened to be a bag of sugar. “Instead, I had to come down here and get these paperclips myself. From now on, Ashley, you come to me with your problems, got it?”

Ashley squeaked out a sad “Yes, sir,” and whimpered slightly before asking, “I am sorry I let you down. Do you need to punish me, now?”

I set down the bag of sugar, took a hold of Ashley’s arms, and directed her hands to take hold of the lower shelf in front of her, which **** her to bend over at the waist as well. “Well, it is your first day, so I expected a mistake or two. That said, a bit of corrective action is the best way to prevent future mistakes, don’t you think?”

Ashley spread her legs as wide as her tight skirt would allow and thrust her ass further backwards, offering up a tempting target, “Of course, sir. Please, help me to be a better secretary.”

I could not refuse such a heartfelt plea. I reached down and groped her through the fabric of her skirt for a while before rolling it up and exposing the bare flesh beneath. “No panties,” I commented, running a testing finger along her exposed slit and pulling a low moan from my slutty secretary.

“I wanted to save you the extra step, sir.” Ashley offered, already breathless and shaking.

I smiled at that, then slowly worked a finger into her pussy, which rewarded my efforts by clamping down on the digit, moist and eager for attention. I pushed the finger in and out of Ashley for only a couple seconds before withdrawing completely, after all, she was in need of punishment, and I didn’t want to be too soft on my new secretary. I adjusted my position as ideally as possible within the cramped pantry, rose my hand into the air, then brought it down against Ashley’s right cheek with a clap that filled up the room, momentarily silencing Ashley’s whimpers and gasps. I delivered the next slap with just as much ****, and Ashley thanked me for the effort, before asking for another. I obliged, and threw in a few more for good measure before deciding to move forward.

Ashley’s head perked up at the sound of my zipper coming undone, and I could see that it was taking some effort for her to stay facing forward. We were both fairly aroused by this point, so I didn’t see much point to wasting more time, instead lining myself up with her wet pussy, and giving one sure, powerful thrust, bottoming myself out in that familiar warmth. Ashley moaned and gripped me tightly. “Th-thank you, thank you, sir, oh, thank you…” She continued to thank me enthusiastically as I began fucking her in earnest, the **** of my thrusts causing the shelf she was bracing herself against to shake unsteadily. I’d rather not do any real damage to my home, so after a handful of thrusts I peeled Ashley’s hands away from the shelf and pulled her into a standing position, before whirling her around and pressing her now against the door. The door was much steadier as I fucked Ashley against it, her muttered words devolving into meaningless noises of pleasure. Her orgasm arrived with a particularly hard thrust, the spastic quivering of her cunt bringing my own climax shortly after. I moved my hands from her hips to wrap around her waist as I pumped my seed into her, holding her in place as we both caught our breath.

“So, Ashley, have I made myself clear?”

Ashley turned her head to look back at me, her face practically glowing, “Yes, sir. Next time, I’ll come to you.”

I gave one last pointed thrust before pulling out of Ashley and releasing my hold on her, “Good girl. Now go finish that scheduling, and meet me back in my office in a half-hour for an… evaluation.”

Ashley slowly straightened herself up, rolled her skirt back down so it covered her pussy, and gave a cheery “Yes sir!” I patted her ass, opened the door, and watched her confidently march away, her stride in no way betraying the cumload that was slowly leaking its way out of her pussy.