Ashlynn Goes to Work Ch. 02

Alone in my apartment that night, it took me forever to relax. Even after a long shower washed his scent from my skin, my mind raced with vivid memories of my encounter with John in his office. When I finally did fall asleep, my dreams were filled with the hot images of what I hoped he might have planned for the next day. I awoke to find my fingers teasing my clit and exploring my wet pussy.

I indulged these sensations for only a few moments more before realizing I needed to get ready for the day and pulling myself out of bed. Naked, I walked across the bedroom to my closet, opened the doors, and pondered my options. The logical, practical part of me knew that I should dress just as I would for any other day at the office. But what if John really was planning a rendezvous for us that afternoon?

The compromise was simple: a professional exterior, and my sexiest matching undergarments. I chose my favorite bra, pink and satiny, and matching thong panties. It was all I could do not to touch myself as I posed in the mirror. But a quick glance at the clock put me back on track, as I realized I'd be late for work if I didn't hurry. I selected a form-fitting but professional dark blue v-neck sweater, black slacks, pumps, and a pearl necklace, and headed out for the office.

After settling in at my desk, I scrutinized my coworkers' faces as they said their good mornings, looking for any sign that any of them were aware of the naughtiness that had taken place the previous afternoon. Each time John passed by my desk, e-mailed me with a new task, or talked to someone else, I searched for any clue of his intentions for our meeting later in the day.

The morning crept by. I felt as if I was the only person operating at normal speed, while everyone around me was in slow-motion. Just before noon, John stopped by my desk, and talking loud enough for anyone within earshot to hear clearly, said, "I'm heading to lunch now, Ashlynn. Why don't you do the same, and then meet me at my car at 12:30 so we can be sure to be at that meeting on time?"

"You got it, John," I said as calmly as I could, "see you then."

Still I didn't know. He could just be teasing me. Maybe John viewed yesterday afternoon as an isolated thing, a momentary lapse in otherwise good judgement. Or maybe he did indeed have something planned for this afternoon. But that was the beauty of it. Nobody in our office would suspect a thing if we drove off together for a few hours. After all, it happened all the time. As John's 'right hand girl', I was often by his side for meetings. Little did our coworkers know where my right hand had been yesterday afternoon in his office, or for that matter, this morning in my bed as I relived the experience.

I was far too excited to eat lunch, so I gathered my things and took a walk outside, making a few loops around our office building to get some fresh air and compose my thoughts. After repeated glances at my watch, it was finally time, so I made my way to the parking garage, down a level to the spaces reserved for executives like John, and waited for him to arrive.

A few moments later, he emerged from the elevator and walked towards me. He was carrying his briefcase, as he always did when he left the office for a meeting, and finishing a conversation with a colleague he'd obviously bumped into on his way, before shaking the man's outstretched hand and taking the last few steps towards me with a smile.

"Ready, Ashlynn?"

"Yes, sir! Although I still wish you'd tell me a bit more about this meeting we're going to. You know how I hate to be unprepared!"

"No worries, Ashlynn, there will be plenty of time to fill you in on the drive there."

Once again, this dialogue was loud enough for anyone close by to hear, and once again, it was so typical of our interactions that it couldn't possibly raise any eyebrows.

As soon as we pulled out of the garage, his demeanor changed.

"So, Ashlynn, there's something you said yesterday that I can't get out of my head."

"Oh, really, what's that?"

"You said that you didn't mind pain, that you actually find it exhilarating."

"Oh, that. Well, yes, that's true."

"I thought perhaps we could explore that this afternoon."

"Hmm..." I was relieved to know that we wouldn't be sitting in a boring meeting, but had to admit to him my nervousness. "Well, I can't say that I've ever explored it before, except that one time with the tattoo."

"Don't worry, Ashlynn. You can trust me. Spread your legs."

"Now, in the car?"

"Yes. And please, no questions, just do as you're told."

"Yes sir."

I spread my legs as wide as I could, and he began caressing my left thigh with his right hand. I relaxed back into the seat, resting my head on the head rest and looking over at him as he drove. Just as I let out a calm sigh, he raised his hand and smacked my inner thigh, hard. I squealed in surprise, but made no move to stop him from continuing.

"Good girl. Do you want more?"

"Yes, John, please."

For the rest of the drive, he abused my inner thighs, alternately pinching and slapping them until I was aware of little other than the stinging sensitivity of that skin. I closed my eyes for a few moments, opening them again to find that we had entered a parking garage. Although I'd been paying little attention to the drive, I quickly realized that I'd been to this place before. It was the hotel at which our company maintained a suite.

You see, there was enough wining and dining to be done with business partners, enough executives being flown in from other regional offices, that it was more efficient for the company to maintain one location than to have to deal with making reservations each time around. I'd been here many times, although never as a guest. My role was usually to pick someone up to deliver them to a meeting, or to drop someone up after picking them up at the airport. Needless to say, this was the first time I'd been brought here for a mid-day rendezvous.

"Are you sure we'll be OK here, John?" I asked him as the elevator doors closed on our way upstairs. By his answer, he obviously knew what I meant.

"Don't worry, Ashlynn. I told the office I was meeting a VIP here, a potential new client. I said I couldn't share his name until we closed the deal. And of course nobody will think anything of the fact that you came with me. Don't worry about a thing."

Impressed with his calm and his ability to plan something like this amidst all of his other responsibilities, I wondered for a moment how many other times he might have done this, and with how many other girls. But I quickly decided I didn't really care. All that mattered at this moment was that I was here with him.

"Wow," I said as he let me into the suite and shut the door behind us, "it really is beautiful, isn't it!"

It was the penthouse suite, with a view of the downtown skyline from the expansive entertaining area. But before I could soak in much more of the view, John took my hand and led me into the bedroom, spacious enough to seem, well, spacious even with its king-sized bed.

He set his briefcase down on the corner of the bed and began taking his clothes off, while I awaited my next instructions. I watched as he neatly folded and stacked his clothes on a chair in the corner of the room, then turned to me again.

"Take off your sweater and slacks. But leave the pearl necklace. I want to see you in that with just your bra and panties."

"Yes, sir."

I quickly undressed, handing him my clothes, which he stacked on top of his.

"Now, Ashlynn, get on your knees. Crawl over to the bed, and open the briefcase."

I did as I was told, and gasped as I opened the briefcase. Instead of the usual papers, it was filled with various objects which I quickly realized to be an arsenal for both pain and pleasure. There was a riding crop, angled just so to fit in the briefcase. There were handcuffs, and also ropes, clearly for being tied up. There was a small wooden paddle.

I turned around to find Josh immediately behind me, straddling me so that his growing cock was directly behind my head.

"So, Ashlynn, what do you think?"

"I've never done anything like this before, but I've always said there's a first time for everything!"

"I like your attitude. Turn around."

I remained on my knees but turned to face him, and he grabbed me by the hair and shoved his cock in my mouth. I eagerly reached up to use my hands as well, but he stopped me, grabbing my petite wrists in his big, strong hands and pulling my arms up over my head, so that I had no choice but to take him completely into my mouth and, as he grew, into my throat.

He freed one of his hands, still controlling my wrists with his other, and reached down to pick up the wooden paddle. With no protest from me, since my mouth was completely full, he began swatting my ass with the paddle, gently at first, then more firmly, as I gasped for air. I maintained my composure as best as possible, fighting to continue a regular motion up and down on his cock in spite of the occasional blast of pain to my ass cheeks.

After a few more minutes of this treatment, John suddenly pulled me to my feet, kissing me passionately as I felt the blood rush back into my lower legs after so much time on my knees.

"Take off your bra and panties."

I once again did as I was told, watching John put down the paddle and pick up the riding crop. Once I was completely naked save for the pearl necklace he obviously wanted to remain, he spun me around so that my back faced him, and embraced me from behind, his hard cock slipping between my legs and rubbing against my pussy lips. He gently swatted at various parts of my body with the riding crop as he used his free hand to pinch my nipples hard, squeezing and twisting them in his fingers until I writhed and squealed under his touch.

I nearly came under this treatment, with the riding crop settling on my clit, his fingers torturing my nipples, and his big strong body enveloping mine, but before I could reach a climax, he backed off and pushed me down onto the bed. He now tossed down the riding crop and pulled from his briefcase two sets of black rope.

Although I had never been tied up before, I immediately understood their purpose, and rolled over onto my back and stretched out my limbs so that he could position me as he wished. The ropes had pre-tied loops for wrists and ankles, and in just a matter of seconds, he had me spread-eagled on the bed, one limb connected by the rope to each corner of the bed.

I suddenly realized how vulnerable I was in this position, and almost without meaning to, fought against the ropes for a few moments.

"It will be much easier if you relax, Ashlynn. See how they work? If you fight, the ropes tighten against your skin. If you relax, they actually give you some room to move."

"Yes, sir. I understand."

He climbed on top of me in a 69 position, his hard cock directly above my mouth. Once again, I wanted to reach up to touch him, to pleasure him with both my hands and my mouth, but clearly now I had no choice but to use just my mouth and throat. He slowly lowered himself into me, and the angle created by this position allowed him even more depth into my throat than before. He moaned with pleasure as he held himself in this position, as I struggled to breathe.

Just as I relaxed enough to realize that I could breathe through my nose, he began playing with my pussy with his fingers, causing me to gasp and my heart to pound once again. His touch was expert as he slowly spread me apart, tickled my clit with his tongue, and probed me with his fingers.

I began to feel him getting closer to a climax as he pounded in and out of my throat, but just then, he pulled out and climbed off of me, crawling down to position himself on his knees between my legs. He reached up to put an extra pillow under my head so that I could easily see what he was doing, and then quickly inserted one, then two, then three, then four fingers inside of me and began a furious pounding of my dripping wet pussy.

The sensations were unlike anything I had ever felt, especially as he bent down to suck my clit into his mouth. To be unable to move, unable to control any aspect of his motions, and all the while to be able to watch, was more than I could take, and my body soon shuddered with a profound orgasm.

Before I had even come down from my high, my eyes closed as I enjoyed the sensations, I felt him releasing my wrists, and then my ankles, from the ropes. As I sat up and stretched my limbs, he rolled over onto his back in the middle of the bed, caught my eye, and asked a naughty question.

"Are you ready to ride me until I cum, no matter what else I do to you?"

"Yes, of course. You can to anything to me that you like."

He smiled, picked out a few items from his briefcase, and said, "good girl. Climb on."

I stroked his cock a few times with my hands, then straddled him and slowly lowered myself onto him. Once he was completely inside of me, I held there for a few moments as he took one of my breasts in each hand and firmly pinched each nipple. As I began riding him, he held my tits firmly in his hands, creating an intense feeling as he kept them from moving as the rest of my body traveled up and down.

He then suddenly let go, allowing my breasts to bounce freely, and I watched him reach once again for the riding crop. He began swatting me on my ass cheeks and lower back, sometimes gently, sometimes anything but, as I rode him faster now.

"Slow down, Ashlynn. Slow down."

I responded immediately, and locked my eyes on his as he put down the crop and reached for something else that was out of my view. Suddenly, I felt something - it must have been a small dildo - pressing against my virgin ass. I whimpered and resisted for a moment, but could see in his eyes that he was imploring me to trust him, so I relaxed as much as possible as he slowly pressed the object into my ass.

Once it was inside, he held it in position and whispered to me to begin riding him faster once again. The feeling of fullness for me was, obviously, unlike anything I had ever experienced. And I could sense from his reactions that it added a tightness for him as well. His hands once again came to my breasts, kneading them as I now began riding him furiously. My muscles kept the dildo in place as I experienced yet another powerful orgasm.

And once again, John's stamina outlasted mine. After allowing me to ride out my climax, crying out as I rode him, he lifted me off of him, gently tossed me down to the bed, and straddled my chest, stroking himself for a few moments more before he shot a huge load of cum all over my chest, covering my tits and running down to my belly.

I took it upon myself to show him my appreciation by rubbing his cum into my skin, massaging my tender nipples and sore breasts before finally tracing a finger through the warm sticky goo and lifting it to my mouth for a taste.

John smiled, kissed me gently on the lips, then helped me off the bed.

"We've just got time to get cleaned up before heading back to the office. You'd better shower, I'll get the room tidied up."

It couldn't have been more than 30 minutes before we were back in the office. As nervous as I had been that morning that someone might have suspected something, I was now equally confident that nobody would. I could only imagine what John would come up with next.