Ashlynn Goes to Work

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.