Ashlynn Goes to Work Ch. 03

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“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 bursa escort 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.”


“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 bursa escort bayan 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 escort bursa 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…

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