Ashlynn Goes to Work, Chapter 4

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.”

Ashlynn Goes to Work, Chapter 3

“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...