Showing Abby Who's Boss

Five years ago, Abby strolled into the meeting room and into my life as a 18-year old having just completed high school. I still remember what she wore: red gym shorts, a blue tank top and black flip flops. Her light brown hair came down loose to her shoulders, swaying as she sat down in the seat next to me while we both prepared for the first day of orientation for a summer job for which we had both been hired as temporary employees.

My first thought was that Abby was awfully cute, but my second thought was that she was a little young for my taste. Even then, though, my mind couldn't help but wander, considering how I'd like to defile this girl one day. I couldn't help but notice her slender frame, bright green eyes and light freckles that were all but covered up by her makeup, all combining to lead me to believe that, with a little more seasoning, Abby would be an exceptional talent as far as my lust was concerned.

As it turned out, Abby and I hit it off right away. I realized quickly that she was a very sweet and very fun girl. I also found out that she had a boyfriend and that she was still six years younger than I. Oddly enough, she remained very friendly with me, leading me to believe that there was some sort of mutual attraction between the two of us. However, I'd let my imagination get away for just a few minutes before always pulling myself back and remembering the whole contemplation was moot anyway. I had plenty of reasons to resist any temptation with the young girl - for now, that is.

We worked together for just those couple brief months, but we stayed in touch through the years, mainly via social media. While it would be more than four years until we would meet again under fortuitous circumstances, I never took my eyes off her, figuratively speaking, of course. I noticed when she dumped her boyfriend a couple years later and soon after found out through a mutual friend that Abby did in fact have a crush on me. Despite my attempts to meet up with her, I was met with frustration for a number of reasons until she was off the market again.

Finally, last summer, now in a career job, I was hiring in my department after a couple people left the company. The majority of my staff was female, and a few of these ladies were young and attractive. For the past couple years, I'd successfully fought off the urge to pursue a sexual relationship with a couple of them, but I started to change my mind about the risks involved in hooking up with an employee when a particular application came through my email.

I called Abby immediately after receiving her resume and set up an interview for the following day. While personally I was excited at the prospect of being Abby's boss, professionally I wasn't sure if Abby was the most qualified candidate for the job. Of course I was going to give it to her, but in my mind she was still the 18-year old with a history of immature relationships. The work required in the position for which I was hiring demanded more than entry-level skill.

On the day of the interview, I greeted Abby for the first time in four years. Right away I noticed that the young girl was growing up into a capable woman. At 22 now, she still had a lot to learn, but I realized how unfair I had been to judge her based on my work with her when she was 18. She went on to nail the interview from start to finish: arriving early, dressing professionally, presenting an impressive cover letter and resume (for a girl just finishing college) and answering all my questions very well. Of course, the interview was more casual than most of the ones I conducted, and by the end we were just catching up. Afterward, though, I just had to cross a few t's before I called her the next day to offer her the job.

Abby continued to only impress me. She caught onto the job duties quickly and was one of my top performers within a month. She was also just as cute and friendly as I remembered her, only now she was more mature. Without even realizing it, I was spending more time than I needed to with her at work, and we were drawing out email conversations to an extent that was no longer professional. Things between us were going so well both personally and professionally that those fantasies soon returned, although I originally had no intent on carrying out my thoughts.

This past spring, the chemistry and sexual tension between Abby and me reached a fever pitch. She was still performing admirably at her job and was more and more often the star of my lustful fantasies. By May, I was at a place in my life where I was no longer satisfied with just thinking about my cute employee. I was going to pursue actually fucking her.

Becoming personally involved with an employee was risky, obviously. I knew, for what it was worth, right from the start I wasn't looking for anything serious with Abby. She was cute, but I didn't want a lasting relationship - just a fun time and a good story. Even though I had entertained the thought of having sex with Abby for a few years now, the fact that I was her boss made it even hotter.

I would come to find out that Abby was looking for nothing more than I was too. It turns out that even though she was attracted to me, she went down this path with me only because the thought of getting railed by her boss really turned her on. Also, I think she was hoping for some extra perks for her job. Regardless, for now, though, I had no reason to believe she was seeing or committed to anyone else or not looking for commitment, so I had to play my cards carefully.

By my design, Abby and my conversations became more casual and often not even born from professional matters. I was encouraged at how easy it was to talk to her on a much more mundane level. Yes, I'd always been comfortable talking with her, but she seemed especially agreeable with developing a real friendship outside of work - perhaps even eager to push our relationship along, something I was never able to do before she worked for me. Within two weeks of determining to sleep with her, I was comfortably joking with her about sex. It wasn't long at all after that point that I was suggesting a little office romance.

"That would be fun," I said over a casual lunch one Saturday afternoon. My heart was going weak as I tried to sound just casual enough to not seem like a creep but confident enough so she would take me seriously. It was quite the tightrope to walk after just implying to a subordinate that we have sex together. "What do you think?"

"Please tell me you're serious," Abby answered. My heart was pounding now, and I almost forgot to breath.

"I am if you are," I practically choked out. "Maybe tonight?"

"We can go to my place tonight!" The words spilled out of her mouth. It struck me that she was even more nervous than I. "I thought you'd never ask."

Abby and I had already made separate plans for the rest of the day, so we split up after lunch and agreed to meet up later that night. As I spent that afternoon with my friends, my mind kept going back to what was about to transpire. Even though I was enjoying the company of my friends, as always, that day really dragged on. I didn't talk with my friends about the dream I'd be living that night, though, because I don't like to count my chickens before they hatch.

For two years, since I started managing females at work, I'd fantasized about sleeping with more than one of them, but I'd never pursued it. It was an exciting endeavor I had planned for this evening, one I wouldn't forget anytime soon. I knew I'd have to be careful about bragging about it so that neither one of us got into any trouble at work. At this point in my life, though, I had already expertly navigated at least one complicated sexual conquest, so I wasn't nervous about blowing our cover.

Abby and I met at a coffee shop where she worked before coming to my company. She wore a cute and tasteful outfit, starting with a blue, short-sleeve, button-down shirt with no other shirt underneath so as to reveal a little cleavage. Her pants were tight black stretch pants that reached down to her black flat shoes. Sure, it wasn't the most arousing outfit I'd seen before sex, but we did meet in public, for one, and it was something she'd wear to work if it were buttoned up a little more. Come to think of it, I should have dressed up a little more to take on the boss role, but for the first time there was no need for role play when, in reality, I was her supervisor.

Anyway, we ordered some cold caffeinated drinks from a cashier with whom Abby was familiar, having been coworkers in the past. We sat down as we waited, not saying much since we were both pretty excited and nervous to do what both of us had wanted to do for, I presume, years now. The added element of the professional relationship simply made the long wait worth it.

When our order was ready, Abby insisted on getting up to grab the drinks and bolted to the counter. Handing Abby the drinks was the same girl who took the order. Our table was too far away for me to hear the words that were being exchanged, but there was definitely some whispering and giggling going on. When Abby sat down, she was still grinning and blushing a little bit, so I asked her what the commotion had been about.

"I told her who you are, that you're my boss," she said, " and that after we leave here, I'm going to fuck your brains out." Abby blushed even more, barely able to get those last dirty words out without giggling more. I could hardly breathe.

We didn't linger at that coffee shop. Within an hour, we were in her apartment. It was very neat and clean, more so than one would expect, as if she'd prepared for my arrival. The dwelling seemed kind of big for just her, but she insisted she did not have a roommate. Also, there was no way she was affording this place by herself on what I was able to pay her, but I just assumed her parents were covering some bills for her or something. It was the only scenario that made sense, especially since she told me she had just started school again.

We were too excited to do anything other than head to the bedroom. We made out a little as we stood in the living room, marking the first time I ever kissed a girl who worked for me. When we entered the bedroom, I was greeted by a sweet smelling scent and a large double bed against the far wall. In this room, too, everything was cleaned and organized. There were a couple candles on the nightstand that Abby lite as soon as we entered so that there was no need to turn leave the light on, so I turned it off. In just a few seconds, the smell of lilac began to join the already sweet aroma in the room.

After some touching, I pushed Abby down on her bed. The mattress felt relatively new, very soft and comfortable. We made out for a couple minutes before I backed off to allow Abby to unbutton her shirt, revealing a pink push-up bra. As Abby worked on her top, I knelt beside her and pulled her pants clean off her body, knocking her shoes off with them. At that point, I started to take my own clothes off, and from there we continued until we were both completely naked.

As soon as the pink bra hit the floor beside the bed, my naked employee pulled the blankets up and slid under, taking her bare boobs away from me as soon as they had been presented, and invited me to join her. I eagerly complied; after all, even as the boss, I was always open to the suggestions of my staff. As soon as I joined her, Abby took my already raging cock in her hand and stroked it vigorously. she smiled as I sighed, the two of us lying on our sides while she jerked me, her soft hand sliding quickly up and down my stiff erection.

After stroking my cock for about half a minute, Abby slid under the covers, causing my heart to leap as I prepared for the next level of pleasure. For the next few minutes, she sucked my cock, which she continued to hold at the base. I lifted the covers so I could look in and make eye contact with my favorite employee while her head bobbed up and down, her tongue pressed against my shaft. While she demonstrated her cock-sucking ability, I uttered the words, "Fuck me, Abby."

"Yes, boss," she replied, pulling her head back and jerking my now slick penis. I hadn't even been going for the boss-employee dynamic there, but I'm glad she took it that way.

Emerging from the covers, Abby spread her knees so that they were planted on either side of my hips. My cock was now pressed against her shaven pussy while the blanket rode around Abby's waist. She looked up at me one more time, those green eyes reflecting the candlelight, which also cast a warm glow on her freckled face, though her freckles were, as usual, mostly obscured by her makeup. Then she looked back down at my cock as her light brown hair hung down around her neck and shoulders. Abby grabbed my cock, slightly lifting her body, and slipped my member into her pussy.

Abby's young, 22-year old pussy was warm and wet as my cock slid into it, while my employee's smooth flesh slid against mine until my balls were touching her taint. She leaned forward, putting both hands in front of her on my stomach as she rotated her hips and ground against me. We moaned in unison while I gripped the sheets beneath me.

"Ride me," I said, this time fully intending for her to take it as an order from her supervisor.

"Yes, sir," she said meekly, smiling sweetly at me as she submitted. She briefly humped my cock a bit before lifting her back end up and sliding back down to my balls, grinding against my hips for a second and then sliding back up. My hands shot out onto Abby's thighs just as she began to steadily ride my cock.

Abby kept her hands on my stomach but made her arms rigid, pulling away from me just a little as she slid up and down my engorged prick. Her pussy was tight and wet, maybe the tightest I've felt. She was certainly the youngest girl I'd been with, even if just by a bit. She was obviously not a virgin and led me to believe she was no rookie either.

I moaned a little louder as Abby rode up and down my cock over and over again, going faster and faster as she continued. Her boobs and hair bounced along with her, and she started to breathe more heavily. Eventually, she pushed herself straight up, bucking her hips and putting one hand in her hair and the other on her right boob while she continued to fuck me. The mattress creaked slightly underneath us, and I clutched her thighs as the realization only began to sink in that I was having sex with one of my staff members. Sure, I knew her before I gave her the job, but that fact didn't make the experience any less incredible.

By now, the blanket had fallen off Abby's back altogether, now mostly on our legs while she fucked me. I desperately held onto her as, before long, she was going at a crazed pace, indicating that she was just as turned on by fucking her boss as I was by being fucked by my employee. She began to cry out and yell as my cock jammed deep inside her juicy cunt again and again until she shouted that she was cumming. I don't know how thick the walls in that room were, but I couldn't imagine she went unheard.

Being pretty close to cumming myself, I grabbed Abby's lower back while she shuddered from her orgasm and, leaving my cock buried in her, rolled her onto her back and lay on top of her. As she came down from her orgasm, I lay down flat against her, her boobs pressed against my chest as I kissed her and began to thrust in and out of her. Abby wrapped her legs around me, kicking the blanket off and clawing at my back as I pounded her against that mattress which was now creaking louder beneath us.

We were now coated in sweat, which was mingling together as I slammed into Abby hard and fast. We moaned into each other's mouths while I put one arm around her back and held her head with the other. Our bodies slipped together while she squirmed below me. I could feel my balls preparing to burst as they slapped against her taint.

"How does it feel to get nailed by your boss?" I managed to say, fucking Abby as hard as I've ever fucked anyone. She just laughed and sank her nails deeper into my back, taking the pummeling. At last, I felt my cock ready to erupt, so I warned Abby, who relaxed her arms and legs in response, allowing me to rise to my knees.

As soon as my cock slipped out of Abby's wet sex hole, I took the initiative to jerk myself off furiously as I gazed at my pretty employee. Her body shone all over with sweat that glowed in the soft candlelight. As Abby caught her breath, her boobs heaving up and down, I decided between plastering those tits or her face.

Before I could make up my mind, the first shot of my jizz fired right at Abby's chin, making the choice for me. I went with it and proceeded to paint as much of Abby's face as I could with my cum, first splattering it over her nose and eyelids before moving to her left cheek and then her forehead. One errant shot struck in her hair. I continued to masturbate until the last few ropes of cum escaped onto her mouth, and then I was spent.

I collapsed next to Abby, who turned over briefly to blow out the candle on the nightstand, leaving us in the dark. She reached for some tissues to wipe off the cum that now gleamed in the pale ray of moonlight that shone through her blinds. She turned to me and asked, "How did I do, boss?" As my heart was still slowing down, I laughed a little and told her she'd outdone herself for sure. I think at that point I fell asleep, because I don't remember anything else.

I stayed the night, but beyond that meeting, we didn't see each other out of work again for a while. It was about three weeks until we had sex again, but I'm getting ahead of myself. Before the next session, Abby one day started to try to explain she wasn't ready for a relationship, at which point I cut her off and told her I sincerely was just looking for fun right now. She seemed relieved with that answer and said something about how hot it was to have sex with her boss. I told her I agreed that the dynamic was really sexy and suggested we do it in my office sometime.

"I was just about to say that!" she said excitedly.

Things continued on pretty normally for the next couple weeks. Usually after I'd have sex with a girl, I'd get antsy and try to expedite the next session, but I didn't feel that way with Abby. It certainly wasn't because it wasn't a memorable experience. In fact, it was quite the contrary. Not only did I sleep with one of my employees, but I'd longed to plug Abby for the past four years. At this point in my life, though, I wasn't ready to trust one girl with any type of connection, be it physical, emotional or both, so the whole situation was beyond ideal. I was pleased that we were in agreement, though I'd yet to find out the reason for Abby's compliance.

All that said, we referenced our night together a few times over the course of the next few weeks, even while talking casually at work. Most of the time it was through text, though. After a couple weeks, we were texting about arranging a tryst in my office to really bring home the boss-employee dynamic. After all, that fantasy was a pretty common one.

Fucking one of my staff members in my office had been a dream of mine for a couple years now. Sure, maybe I was kind of cheating by hiring a girl I'd already wanted to bang and who'd already had a crush on me, but it was still going to be hot as hell. We just needed to arrange it appropriately so we wouldn't get caught or raise suspicion.

My office, fortunately, was one of the most secluded in the building. It wasn't even accessible from the main hallway. You'd have to go through one door and then down another hallway just to get to it, so no one was going to just stumble upon it, and evening security had no reason to be down there. There were also no windows, which was awful on these summer afternoons, but it was going to work in my favor this night.