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Ashlynn Goes to Work

By: kimbelina



It all started at Thursday's staff meeting, just two days ago. That's when my working relationship with my boss started to change. Perhaps I should back up just a little, to set the stage.

My name's Ashlynn, and I started working for John three years ago, when I was fresh out of college. He's a VP for the company, responsible for about 50 employees in our regional office. I was originally hired as a receptionist, just trying to get my foot in the door, but John claimed me as his personal assistant just a few months later, and we've worked together ever since.

At first I was suspicious that he'd picked me because of my looks - I'm 5'8", lean but curvy in just the right places, with perfect C-cup tits, a tight ass, big green eyes, and a pretty face framed by long, wavy auburn hair. Let's just say, it wouldn't have been the first time in my life that a guy singled me out for my looks. But the more I worked with John, it was clear that the most important thing to him was to surround himself with people he could trust, in terms of both competence and discretion. And because I brought both to the office each day, I'd become his trusted right-hand girl, as he was fond of calling me.

Anyway, back to the staff meeting. John liked to have me attend most of his meetings with him, so I could be fluent in his workload and prepared to assist him with anything that might come up. I have to admit, it was sometimes dull, but I do appreciate the trust he places in me, which has grown so strong that he's even started asking my advice on matters of company policy or business strategy. 

But don't let that fool you, I'm still responsible for the most mundane of office tasks. In the case of this particular staff meeting, that meant that after making the coffee and preparing copies for everyone attending, I was also the one to jump up on the conference table to get the projector on the correct setting. I was very aware of many sets of eyes on me as I worked to quickly complete the task while not giving too many easy glances up my short skirt.

An hour later, as John and I walked back into his office after the meeting for our usual one-on-one debrief, he asked a question that threw me off-guard.

"So, Ashlynn, all this time, I've never known that you have a tattoo?"

"Huh, oh, um, yes.... wait, when did you see it?"

"When you climbed onto the conference table. Don't worry, I'm not offended! Just curious, that's all. You've never struck me as the tattoo type. Here," he said, motioning for me to sit down as he closed his office door behind me, "have a seat."

"I know, it was one of those college things."

I hoped he'd leave it there, as it wasn't a story I was particularly proud of, but of course if John asked, I'd have to tell him.

"And not just a little butterfly on the shoulder, but a tramp stamp?"

I blushed, slightly shocked, but smiled back at him. It was typical John to get straight to the point. He also had always amazed me with his confidence in talking to much younger women. He was, after all, nearly twenty years older than me. He smiled as he sat down at his desk, across from me.

"Well, yeah, it wasn't the best decision I ever made."

"OK, now you have to share. Diligent, hardworking Ashlynn made a bad decision? I don't believe it!"

I laughed. "Oh, alright, I'll tell you. It was my 21st birthday, and my two best girlfriends dared me to do it. Needless to say, we were all a bit drunk. When I refused, they told me they'd do it with me, so the three of us took the plunge together."

"So what's wrong with that? It's just some innocent Chinese characters, right? Come over here, so I can see it again. I studied a bit of Chinese a few years back."

I stood up, walked around his desk and turned around, lifting my blouse slightly so he could see the tattoo. He could be bluffing about the Chinese, but in case he wasn't, I'd have to tell him the rest of the story.

"Well, the problem is that in my inebriated state, I didn't do my homework on those innocent Chinese characters. It was supposed to say 'love, happiness, and abundance,' but I've since learned that two of the characters are slightly off. And given the location on my body - the 'tramp stamp' as you called it, well, let's just say it sends slightly the wrong message."

I blushed again. 

"Yes, Ashlynn?"

"It basically says that lots of sex makes me happy."

"Ah, I see. A subtle, yet important distinction."

Nervous and surprised that I'd just shared this story with my boss, I babbled on, "and don't get me wrong, it's not that I'm a prude, it's just..."

"I completely understand, Ashlynn, how about we change the subject now."

"Yes, please," I replied, thankful that my classy boss was about to save me from further embarrassment. I turned to face him and reached across his desk to grab my notepad.

"So, did it hurt?"

He grinned and winked at me when our eyes met again, clearly enjoying the fact that he had me in such an awkward position. 

"I thought we were going to change the subject?"

"Oh, come on, it's a simple question..."

I rolled my eyes before indulging him. "Actually, I didn't mind the pain. I have to admit, it was kind of an exhilarating experience."

"So, Ashlynn, this is a whole new side of you I'm seeing today. In the span of just a few minutes, you've shared with me that you enjoy sex and don't mind pain."

I blushed hotly now, profoundly embarrassed that my boss was calling me out on what amounted to a highly inappropriate conversation in his office.

"What's that look on your face, Ashlynn, you look like you've seen a ghost?"

"Sir, I just can't begin to tell you how sorry I am..." 

I began to back away, to head back to the chair across from his desk, but John grabbed my hand and stopped me from moving any further.

"What are you talking about, Ashlynn? I'm not angry. Quite the opposite. I'm intrigued."

"Um, excuse me?"

"I've been thinking for quite a while now that it's time we take our professional partnership to the next level, but I wouldn't dare raise the subject until I had some idea that you might be open to it."

"John, I'm not sure I understand?"

"Listen, Ashlynn. You're hot, and you know it. I've wanted to fuck that hot little mouth of yours ever since the day we met. I've wanted to take you from behind right on this desk. But I have a reputation to maintain in this company, and I wouldn't have dreamed of pursuing you until I knew I could trust you completely."

He was still holding my hand, and he squeezed it more firmly as I let myself sit on the edge of his desk, shocked and excited by what he had said. The truth was, I'd been attracted to John since the first day I met him. His confidence, his strong, athletic body, his deep blue eyes and five-o-clock shadow that developed by the time we wrapped up the day's meetings, everything about him turned me on. But I'd become an expert at burying those feelings deep inside me, just to get through the day. Now I had to admit it was John I really wanted buried deep inside me.

"Oh, John, I've fantasized about being with you, too. But are you sure it's a good idea?"

"Get on your knees."

"What, right here? Right now?"

"I thought you said you weren't a prude."

Taking his words as a challenge, I obeyed his command and dropped to my knees in front of him. He leaned back in his chair and spread his legs, while simultaneously reaching for his phone.

"Helen," he said after a moment of silence, "please hold my calls, and please just ask my 4:00 appointment to wait when he gets here. Ashlynn and I have a couple of important things to wrap up from the staff meeting."

As I unzipped his slacks and pulled his half-hard cock out of his boxers and into my hands, he finished his conversation with a "thank you" to Helen and hung up his phone, relaxing back into his chair with a sigh.

"Now, Ashlynn, you know nobody will walk in, but you also know how thin the walls are in this place, so you'd better be quiet."

I smiled up at him as I slowly took him into my mouth, feeling his cock steadily grow under my touch. I let my left hand fall to his balls, gently rolling them between my fingers as my right hand stroked the base of his shaft and I began moving up and down on him with a steady rhythm.

He reached down and unbuttoned my blouse, and slipped his strong hand inside my bra and began squeezing my right breast, teasing the nipple occasionally with a strong pinch. As I picked up my pace, bobbing up and down more quickly now, he put his other hand on the back of my head, gently but firmly forcing me to take in more and more of his shaft until I finally had to remove my hand and take him all the way into my throat.

Fighting my gag reflex, I relaxed my throat until I was able to take in all of his cock - which I guessed to be eight inches. He continued to play with my tits with one hand while the other hand now gathered my hair into a tight, painful ponytail which he used to control my rhythm up and down on him.

I let a moan escape as he gave my nipple an extra hard pinch, but realized the error of my ways when he grabbed my hair even tighter and pulled me completely off his cock, twisting me around so that I was forced to look up into his eyes. He pulled his hand out of my bra and brought a finger to his lips, reminding me that I needed to be as quiet as possible, and I nodded obediently.

Once he was confident I understood, he forced me back down on his cock in one fast motion, and then encouraged me in a very fast up-and-down rhythm. Any guy I'd been with in the past would have cum after just a few moments of this treatment, but I could sense that John had a level of stamina I'd never experienced.

He pulled me away once again, this time letting go of my hair and pulling me up to be as tall as I could while still on my knees. He unhooked my bra, smiling that the clasp was in the front, and pushed the lacy fabric aside. He then took one of my hands in each of his, positioned them on my breasts, and encouraged me to press them together as he pulled me close and placed his cock between them, rubbing slowly up and down, the tip of his cock just reaching my lips and outstretched tongue with each stroke. 

We continued this motion for a few moments more, until he put a finger on my chin and encouraged me to look up at him.

"You've made me so hard, Ashlynn. Would you like to feel me inside of you?"

"Oh, god, yes, John."

"Are you wet? I want to make sure your tight little pussy is ready for my big, hard cock."

I stood up and slowly pulled my skirt up to give him access to explore. His hands worked their way up my inner thighs, pushed my panties to one side of my warm, wet pussy, and he rubbed his fingers firmly against my pussy lips.

"Oh, my goodness, Ashlynn, you certainly are wet. That's a good thing, because I'm not interested in any more foreplay. Are you ready?"

"Yes, please."

He brought his legs closer together, allowing me to spread mine to straddle him. With one smooth motion, he put his hands on my upper thighs, raising my skirt all the way up as he pulled me down on him, burying himself deep in my pussy on his first stroke. It took all my willpower to remain silent as he filled me more completely than I had ever been filled before.

Once I was used to the sensation, I began riding him, slowly at first, then more quickly, although each time I moved closer to a climax, he would slow my motions to bring me down from that high. I wanted to cry out, to plead with him to let me cum, but I also knew that if I trusted him, John would likely bring me to a more powerful orgasm than I'd ever experienced.

He pulled me close, his mouth on my ear, and as if reading my mind, whispered, "don't worry, Ashlynn, I'll let you cum first. But only if you let me cum in your mouth, and promise to swallow every drop. I can't very well have you leaving my office with cum all over your chin, right?"

"No problem, John. I promise."

"OK, stand up, and turn around."

I quickly did as I was told, pulling myself up off of his throbbing cock, turning around, and placing my hands on his desk. He pushed me down further, so that my forearms were pressed against the papers scattered across his desk, and forced my legs apart as he plunged deep into me with one firm motion.

I pressed my face into my arm, once again having to work hard to avoid crying out in a combination of pleasure and pain as he pounded me from behind. I had lost all concept of time at this point, but it can't have been long before my orgasm began building. John reached around and fondled my clit with two fingers just as I reached my climax, forcing me over the edge, and the waves of pleasure were still moving through my body as he pulled out of me, spun me around, and forced me to my knees.

He stroked himself furiously for a few more seconds before forcing himself into my mouth once more. For a fleeting moment, I realized that I was tasting my own juices for the first time, but that thought soon left my head as he jerked and shot his load deep into my throat. I pulled away slightly, catching the rest of it in the front of my mouth, where I could relish its salty flavor while still swallowing every drop, as he had asked me to.

As soon as he was finished, he returned to the businesslike demeanor I was so familiar with. He adjusted himself back into his boxers, zipped his slacks, and helped me fasten my bra and button my blouse. He pulled his fingers through my hair to bring it back to a respectable look, and then motioned for me to sit back down in the chair across from his desk.

I adjusted my panties as best as I could, my own cum still dripping from my pussy, picked up my notebook, and sat down.

"Now, Ashlynn, there's a meeting tomorrow that I'd like you to attend with me."

Work-related thoughts gradually filled my head as I came back to reality, and I gave him a quizzical look. After all, I knew his calendar better than he did.

"But you don't have any meetings tomorrow."

"I will after you add this one. We'll need about two hours, starting at 1pm."

"Um, OK. What should I title it?"

"Strategy Discussion."

"I don't suppose you could give me any more details, so I can be sure to be prepared?"

"Just use your imagination this evening, and come prepared for anything, as I know you always do, Ashlynn. You're a wonderful assistant, always doing such a tremendous job of anticipating my needs. Thanks, that will be all, I'm sure my 4:00 appointment is waiting. Why don't you go ahead and head home for the evening, I'll see you tomorrow."

"Um, OK, John. Thanks for everything."

"No, thank you."

I left his office not quite sure what to think. I had just experienced the hottest sex of my life. I knew I could trust John, but was still filled with a vague sense of mystery about where he intended to go from here. Was he teasing me about the meeting the next day? Was it really just another boring meeting, or was he asking me to schedule a rendezvous for the two of us? My heart raced as I imagined the possibilities.

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.



Ashlynn Goes to Work Ch. 03



"Ashlynn, could we catch up for a minute, please?" John had said these exact words more times than I could count, usually on his way past my desk, returning to his office after a meeting.

"Of course, John," I replied with a smile, and gathered up my notepad and a few files before getting up to follow him into his office, where he closed the door behind us.

It was such a regular occurrence that the several coworkers within earshot didn't even look up. It had been a few weeks since John had seduced me in his office, adding a sexual dimension to our professional relationship, and as best I could tell, nobody suspected a thing. And why would they? John had a stellar reputation within the company as a great guy and a hard worker, and everyone was used to the fact that as his personal assistant, I spent most of every day at his side.

"Have a seat," he said as he sat down across from me behind his desk, "we have a few minutes before the 3pm conference call and there are some things I'd like to go over."

In spite of our newfound intimacy, John still held both of us to the same high standards that he always had. This kept me constantly on my toes, because I never knew whether his next request of me would be to proofread his draft of the quarterly report or to drop to my knees and deep-throat him before his next meeting started.

"So, Ashlynn, I'd like you to sit in on this conference call. I need you to have an understanding of these financials because they will come into play in the proposal we need to finish by the end of the week."

Ah, so he was all business this time around. Time to get my mind out of the gutter and put on my work hat. "No problem, John. Do I need anything with me? I already have the files for that account," I added, pointing to the paperwork on my lap.

"No, that's good. I just need you to listen in. Why don't you come sit over here, and we'll put them on speakerphone."

I stood up and started to grab my chair to move it around to his side of the desk, but he interrupted me, "no, why don't you just sit on my desk."

Hmm, mixed messages. I really would have to be on my toes this time. I did as instructed and walked around the desk, set my notepad and files down, and climbed up onto the desk, watching his eyes as he watched my skirt ride up my legs when I sat down.

He looked at his watch, then turned his arm so that I could also see it was time for the meeting to start. I leaned over so that I could reach his phone, and as I was dialing the multiple numbers for the conference call, he slid his hand up my skirt.

After the call connected and John said a few hellos to his peers from around the company, he hit the 'mute' button on his phone and turned to look at me, his hand beginning to explore my inner thigh, closer and closer to my pussy, which was quickly growing wet.

"Now, Ashlynn, I'm going to ask you to exhibit a bit of discipline here. I've been thinking all day about how much I want to feel your tight little pussy. But I also need you to pay attention to this call. Can I count on you to stay on task, no matter what I do?"

"Yes, sir."

"And, of course, I need you to keep quiet, because there will be parts of this meeting I need to actively participate in."

"Yes, sir."

"Very good, Ashlynn. Now, spread your legs for me."

I uncrossed my legs, and did my best to keep my attention on the businesslike voices coming from the speakerphone, while also enjoying his touch and obeying his every command. The whole scenario was a huge turn-on, which made my job even harder!

His fingers had now reached their goal, pushed my panties aside, and he was now gently fondling my pussy lips.

"Ashlynn, I've been thinking about something ever since our time at the hotel."

"Yes, John?"

"Do you remember when I used that little toy in your ass?"

"How could I forget? It was my first time, and it was amazing!"

"Well, I think it's time for you to prepare for a little more attention for your tight little ass."

"What did you have in mind?"

Before answering, he put his finger to his lips, then to the 'mute' button on his phone, unmuting it before impressively shifting gears and speaking to the group on the conference call for a few minutes. I listened intently, and scribbled down a few notes that I knew I would need later, all the while biting my lip to keep from panting as he pressed a finger inside me.

When he finally muted his phone again, I set down my notepad and let out a sigh.

"Now," he said, "where were we?" He plunged a second finger inside my pussy and began pressing in and out.

"You were about to describe the attention you think my ass deserves?"

"Ah, yes." I was expecting him to describe some sort of role-playing involving a little spanking, but I turned out to be quite wrong. As usual, John got right to the point. "I've been thinking, I really want to fuck that tight little ass of yours."

I gasped, partly in reaction to what he had said, but also because he punctuated his statement by thrusting yet another finger inside of me.

"Yes, Ashlynn? You're not complaining, are you?"

"No, sir. Please, go on."

"So, since I know you're a novice in this area, I'd like to ask you to do some preparation for me."

"Preparation?"

"Yes, you know, the kind you do so well whenever I ask you to handle anything work-related? I want you to apply that same dedication to preparing your tight little ass for my big, hard cock."

He was finger-fucking me furiously now, and it was all I could do to remain still and quiet as he once again pressed the 'mute' button on his phone and rejoined the conference call. With four fingers now pounding my dripping pussy, he calmly addressed his colleagues on a topic I was following the best I could.

I put one hand over my mouth as he brought me closer and closer to climax. He finished his comments and muted the phone call again, just as I was starting to worry that the people on the call would be able to hear the fairly unmistakable slapping sound as his fingers thrust in and out of my incredibly wet pussy.

He stood up and pulled close to me as his fingers continued their furious motion, his lips locking with mine as a powerful orgasm wracked my body. He pulled his fingers out and thrust them into my mouth, and I immediately understood he wanted me to both taste my own juices, but also clean his fingers so that he could get back to work.

"Do you understand, Ashlynn?" He sat back down in his chair, and just as I was about to answer, he unmuted his phone once again to rejoin the conference call, which was thankfully winding to a close.

As soon as he finished the call, I responded.

"Yes, sir. Preparation and discipline."

"That's right, Ashlynn. I want you to be prepared, even without knowing exactly when, where, or exactly how it might happen. And I don't want to hear any complaints about how I'm too big, or it hurts, or anything of the kind. I want you to be ready to take whatever I give you."

"Yes, sir." I tried to exude confidence, as I did whenever he gave me a seemingly impossible work task. But truth be told, I wasn't sure exactly how I was going to accomplish this.

"And the next time we're together, I want you to describe to me exactly how you are preparing for me."

"Yes, sir."

As I drove home from work that evening, I wasn't sure exactly how to approach the assignment he had given me. There was no doubt in my mind that I would do as he asked. And, as I went over his words again and again in my mind, there was no doubt that he'd uncovered a fantasy of mine that I'd never shared with a soul. But how to prepare my tight, virgin ass for his big, hard, eight-inch cock?

I stopped by the store for some groceries, and somewhat bashfully added some personal lubricant to my cart while there. Thank goodness for these stores with the self-checkout lines, gone were the days of inquisitive glances from checkers! When I got home, I tossed the groceries carelessly onto the kitchen counter, threw my jacket over a chair in the living room, and took the lubricant into the bedroom, setting it on my dresser.

I undressed, clipped my hair up to keep it out of my face, and climbed in the shower, my hands exploring my body as I lathered soap over my skin. I played with my perfect C-cup tits until my nipples were hard and erect, and then played with my clit with one finger while my other soapy hand gave my ass a little more attention than it might normally receive in the shower.

I watched myself in the bathroom mirror as I toweled dry, my green eyes bright and my cheeks flush with excitement. I removed the clip from my hair and my long auburn locks tumbled down to my shoulders. I returned to my bedroom and spread the towel on my bed. I went to my dresser, pulled my favorite vibrating toy from my drawer, and brought it and the lubricant over to the bed, where I sat down and pondered my next move.

My clit was tingling and my pussy was hot and wet, but neither fact gave me any confidence about how to approach penetrating my tight ass. I decided to start with a finger, covering the middle finger of my right hand with lube before lying back onto the bed and rolling onto my side. With my left hand exploring my pussy lips and teasing my clit, I slowly pressed that finger until it was buried inside of me.

Not much challenge, and also not much sensation, I thought to myself, suddenly confident and intrigued to push my limits further. My dainty fingers were no match for a big, hard, cock, after all. I picked up my dildo, which was roughly the same size as John's cock. I covered it with lube, held the base of it in my right hand, and began gently pressing the tip against my clenched hole.

I then did everything I could to distract myself from the pain I felt at trying to insert the large dildo into my virgin ass. I gently played with my clit with my other hand, and closed my eyes, imagining John's hands on my body and his instructions to me to prepare for his big, hard cock.

For a few moments more, I was still struggling against myself, but as soon as I gave in to the my fantasies, I relaxed and felt the incredible combination of pain and pleasure as the knob of the dildo slipped into my ass. I twisted the end of the device gently until the vibrator came on, at its slowest speed, and moaned at the incredible sensation, which was unlike anything I'd ever felt before.

I now slipped two fingers of my left hand into my pussy, at an angle so that they passed over my clit each time they thrust inside, and was amazed at the tightness in my pussy that was created by having my toy in my ass. I began a slow, steady rocking motion, with my left hand moving back and forth against my clit and into my pussy, and my right hand slowly pushing the vibrating dildo further into my ass, until I reached the maximum I could handle, which I guessed to be about four inches.

I then reluctantly removed my left hand from my clit and pussy, reached for the bottle of lubricant, slid the dildo back out to the point where just the knob was inside of me, and added substantially more lube before sliding it back inside. I was now able to begin a steady in and out motion as my left hand dropped the lube bottle and focused once again on my dripping wet pussy.

I lost all concept of time and place at this point, so overwhelming were the sensations. It was all I could do to keep up my steady rhythm as an incredibly powerful orgasm began building deep inside. The combination of pain and pleasure sensations from thrusting the vibrating dildo in and out of my ass were fantastic, and the intense pressure that they created for my pussy was amazing. Never before had I been able to fill my pussy so completely with just a few fingers. I cried out when I finally reached my climax, which was ten times more powerful than anything I'd ever experienced when pleasuring myself.

I could hardly wait to tell John how prepared I was, and experience the pleasure of having his big, hard cock buried deep in my ass. But that would have to wait until work the next day...



Ashlynn Goes to Work Ch. 04



I chose my outfit very carefully the next morning, hoping that John would be inspired to follow through on his desires that very day. I'd learned quickly over the past few weeks that John had strong opinions about the importance of dressing professionally in the workplace, but that he also expected to find me in sexy, matching undergarments should the mood strike him to explore beneath that professional exterior.

I selected my favorite purple lace bra and matching thong, and then added matching garters to which I hooked my thigh-high stockings. I smiled at myself in the mirror as I took in the view for a moment before adding more layers. I pulled on a fitted, knee-length black skirt and stepped into my black heels. Next was my purple silk blouse, then the blazer to match the skirt. I pulled my auburn hair back into two small clips, one above each ear, and then rummaged through my jewelry box to pick just the right accents. Pearl stud earrings and a pearl necklace, perfect.

It was 10:30 before I finally saw John, who was late to the office after an early-morning meeting off-site. As he passed by my desk, he paused, smiled, and asked - as always, loud enough for our co-workers to hear - if I could join him in his office to go over some figures. I hoped he planned to go over mine, but tried to tell myself to be patient, as it was always possible we wouldn't have time to do anything but work.

John seemed serious that morning as he motioned for me to sit down across from his desk, and proceeded to delegate a long list of tasks to me. It was at least a week's worth of work, and he told me that he needed it in two days. Yikes! My anal explorations of the night before - and my desire to share that story with my boss - were suddenly the furthest thing from my mind.

When I finally looked up from the notepad on which I had been furiously scribbling, John was giving me a sympathetic smile. "I'm sorry, Ashlynn. I realize I'm asking a lot. But you know I wouldn't delegate all that work unless I had an even bigger list of tasks for myself."

"Absolutely, John. No worries, that's my job, and I'm happy to do it!"

"Thanks, Ashlynn. As always, I appreciate your positive attitude."

"OK, then, so I should probably get to work on all this?" I got up to leave, but John quickly interrupted me.

"Leaving so soon? I was hoping you'd have a story to share with me, about your progress on that other little task I gave you?"

"Um, well, OK..."

John reached over to his phone, dialed four digits, and hit the speakerphone button. I recognized the number immediately from the motions of his hands; he was dialing out to the secretary who sat outside his office.

"Helen, I've just given Ashlynn a huge task list, and now I'm going to keep her away from her desk even longer to go over more figures with me. Could you please order us both some lunch from that deli on the corner, my treat?"

"Yes, John, no problem," replied Helen's sweet, grandmotherly voice from over the speakerphone.

"I'd like to have the food delivered at noon, that gives us about an hour to work. Could you please hold all my calls and make sure we're undisturbed during that time?"

"No problem, sir. I'll buzz you when the food arrives."

"Thanks, Helen."

"So, Ashlynn," he said with a smile after hanging up the call, "where were we?"

"You had just asked me to give you a progress report on my, um, homework?"

"Ah, of course. How could I forget. So, why don't you come sit over here with me, and tell me about your evening?"

I stood up, set down my paperwork, and walked around his desk. I reached down and took the fabric of my skirt into my fingers, and slowly raised it. John smiled and gave me an approving glance when he saw the garters. When I had raised my skirt up to my hips, I straddled John and lowered myself down onto him, and could feel his cock begin to grow hard, pressing against his slacks, as I rubbed against him.

I began a slow, steady grinding motion as I began to describe to him how I had so eagerly followed his instructions to explore my limits of pain and pleasure.

"I'm ready for you, John, just liked you asked me to be. I used my favorite toy to fuck my tight virgin ass, and I loved every second of it. I can't wait to be your dirty little slut."

"Oh, really? So you're telling me you actually like that sort of thing? You didn't think it was too dirty, too naughty for a nice young lady such as yourself?"

"Oh, hell no. It was the most amazing sensation I've ever experienced. And I dreamt all night about how it would be even hotter if it was you penetrating me. Please take me, John. Take me in the ass, right here in your office."

"Well, OK, Ashlynn, if you insist."

He took hold of my hips and ground against me harder now, and I could feel how much his cock was straining to be free of its workday constraints.

"But before I take you in the ass, there's a few other parts of your body I'd like to explore with my hard cock, if you don't mind?"

"Anywhere you like, John. Your wish is my command."

He smiled and pulled me up off of him before pushing me down to my knees. I needed no further instruction before tugging at his belt and zipper to free his cock. I took him into my mouth in one long, smooth motion, my hands reaching to massage his balls as I deep-throated him.

He sighed, leaning back into his chair for a moment to enjoy the sensations before sitting up again and reaching down to unbutton my blouse. Each of his hands found one of my tits, and he began gently, and then not so gently, kneading them and rolling my nipples in his strong fingers.

"Your mouth feels so amazing on my cock, Ashlynn," he whispered, "but you know where I'd really like to have it, is between your gorgeous tits."

I slowly pulled myself up off of his hard cock, which glistened with my saliva, and finished the work he'd started to unbutton my blouse. I started to try to take off my blazer and blouse, but he stopped me, wagging his finger.

"Not so fast, Ashlynn. Remember how close our co-workers are. Always remove as little clothing as possible."

I pulled my tits out of the cups of my bra and squeezed them together, remaining on my knees but pulling closer to him. He scooted to the edge of his chair and rubbed his hard cock against my nipples.

"I don't suppose you brought any lubricant with you?"

"No, John, I'm sorry."

"Then I need you to spit on it. Spit on my cock."

The words sounded so naughty to me, and it felt like such a slutty thing to do, to spit on command, that I was even more turned on. I summoned as much saliva as I could, leaned down, and quietly spit on his him until his skin was dripping with my saliva. He forced his cock between my tits and began fucking them furiously. I squeezed my tits together as hard as I could to create as tight a space for his throbbing cock as possible, and then opened my mouth and stuck out my tougue, which could just barely reach the tip of his cock on each stroke.

After a few minutes, he pulled away from me, stood up, took my hand, and led me to the leather sofa on the other side of his office. He motioned for me to lie down, put a pillow behind my head, and straddled my chest. I once again spit on his cock as he presented it in front of my mouth, then pressed my tits together for him. In this position, he was able to thrust more powerfully, and I was able to actually take a few inches of his cock into my mouth on each stroke.

He reached a hand behind his back, spread my legs, and began playing with my pussy lips and clit, and causing me to squirm beneath him. I did my best to maintain my focus on his cock as he agressively fondled my clit and I felt my pussy begin to grow very hot and wet. Just as I felt that John was approaching a climax, he slowed his motions and then pulled away from me, kneeling on the floor next to the sofa.

"My god, Ashlynn, you have the most perfect tits. I would love to cum all over them, but we'll have to save that for a time when you don't have to walk back out of my office afterwards."

He then returned a hand to my pussy, thrusting two fingers into me as I arched my back to give him more depth. He used his other hand to squeeze my breasts and alternated between them, taking first one, then the other nipple into his mouth and gently nibbling. Stopping just as he had me completely flustered, John pulled away once again and asked me a simple question.

"Are you ready?"

"Absolutely."

He climbed back onto the sofa, and sat down next to me, his cock jutting straight up from his body as he pulled my legs together and helped as I removed my panties and tossed them to the floor. I sat up, straddled him, took his cock in my hand, and rubbed the tip against my pussy lips for a few moments before lowering myself onto him. He kissed me passionately as I rode up and down on him for a few moments, just long enough to provide the lubrication for what I knew he had planned next.

Before I was ready to stop, he pulled me up off of his cock and took my hand, leading me back to the area behind his desk, bringing a pillow from the sofa with us. He positioned me on my knees with my forearms flat against the floor and the pillow to cushion my face. With the height differential between us, he found himself in the perfect position when he went down to one knee.

John was the one to spit now, and I squirmed as I felt the warm liquid hit my ass. With one hand reaching around to fondle my clit, he used the other to help as he began pressing the tip of his cock, lubricated with only his spit, against my tight asshole. Remembering the immense pleasure I'd brought myself the night before, I did my best to relax, focusing on his expert fingers on my clit rather than the incredible twinges of pain I was feeling.

After a few moments, I realized that he'd been able to slide a few inches inside of me, and he was beginning to move in and out, slowly and gently. Pleasure was quickly overcoming pain as I learned to relax even more. He was whispering towards my ear, "oh my god, Ashlynn. You're so incredibly tight. Can I go further?"

"Yes, yes, please. I want your big, hard cock to fill my tight little virgin ass!"

I reached behind to fondle him as he began pushing a bit harder, a bit faster. He moaned when my fingers found his balls, and dropped his hand from my clit and moved both hands to my tits, squeezing them furiously in rhythm with his cock moving in and out of my ass. After a few moments of this, I was completely at his mercy, unable to do anything but feel the alternating waves of pain and pleasure as he took me from behind.

His hands fell away from my breasts now and I felt him pull up off of his knee, shifting his position so that he was crouching behind me. I did my best to lift my tight little ass even higher in the air for him, giving him easier access to pound me with abandon now. He was moving too quickly for me to keep a hand on his balls, so I brought my arm back around, wet my fingers in my dripping pussy, and began stroking my clit. 

I came almost immediately, completely overwhelmed by all of the sensations. As I came back down from my high, I realized that my own orgasm had a side benefit for John. I somehow relaxed enough in that moment of pleasure that he was now completely inside of me, his long, hard cock buried in my ass. Once there, he held that position for a few moments, my muscles clenching around him, before stroking in and out a few more times, and then I felt him jerk and became aware of a new sensation as he shot his load deep inside of me.

We stayed there for a few moments more, panting, catching our breath, before he stood up, zipped his slacks, and then helped me to get up and get dressed. I glanced at the clock and realized that we'd managed to use almost the entire hour available to us before lunch would be delivered.

"Well, Ashlynn," John said, summoning his commanding work voice, "you certainly did an excellent job of preparing. I'll have to think up another, equally inspiring task for you next time!"

"Your wish is my command, sir."