Office Perks

Tommy and I started our own business as young men straight out of college, and the company took off almost right away. Within just a couple years we were moving out of Tommy's basement and into our own office space. By then, we were already financially stable enough to hire our own employees at a decent wage. One of the lessons I noted during that early phase of hiring was that women were better employees, especially young women who were more adept with computers and other technology related to our business. Young women also made the workplace more fun, as we would find out.

Tommy wasn't a long-time friend of mine or anything. In fact, we weren't much of friends at all - just business partners. We met during our senior year of college and happened to like each other's ideas, so we decided to go into business together. Outside of our shared company, we had few things in common and rarely, if ever, saw each other outside of work. Even at work, we had split our responsibilities so that each of us was essentially running his own department within the company with little day-to-day interaction with the other. It really was a perfect setup for us, since we were each very capable of managing our respective aspects of the company on our own.

The atmosphere at work started to change about five years into the life of our business when I hired a reliable female friend of mine named Kaitlyn. I brought her on board for the same reason I employed other young females at the time: she was qualified for the role and reliable. Since she was my friend, I knew I could trust her. It wasn't my initial intention to have sex with her, especially since I hadn't been attracted to her in that way for as long as I'd known her.

My mindset shifted regarding Kaitlyn, however, when the idea of banging one of my employees crossed my mind. It was a really hot thought, but the only truly feasible option was Kaitlyn. I knew Kaitlyn had a crush on me too, so it wouldn't be hard at all to get in her pants. She wasn't quite as arousing as some of the other chicks I'd banged, but she was certainly cute, standing about 5'7" with short blond hair, blue eyes and a thicker but not overweight frame that contributed to her big boobs and nice ass. Actually, she seemed to get hotter the more I entertained the thought of having sex with her.

I didn't act on the impulse to show Kaitlyn who was boss right away. The temptation to fuck her grew more and more, but I successfully resisted for some time because I was dating a girl with whom I thought I had a future. This girl's name was Jessica, and though we'd been dating for only three months, it was actually our second stint dating, and I thought we'd grown up enough since we first dated for us to make it work the second time around. We were talking about moving in together and even the whole kids thing and happily ever after.

Well, Jessica ended up breaking up with me suddenly and painfully. Actually, she never really did break up with me, technically. She simply stopped talking to me. She didn't answer my calls or respond to my texts. The last thing she said to me was that she was really busy and would call me later. Here's the kicker: it was the same manner in which she broke up with me the first time. To say I was bitter and heartbroken is an understatement.

My breakup with Jessica was the last straw I needed in order to be convinced to bang Kaitlyn. One afternoon at work a couple years back, I asked Kaitlyn out, and things progressed quickly from there. We got dinner for the first time the following weekend, and I fucked her at my apartment that very night. It was even hotter and more wild than I imagined it would be. Needless to say, she was ready for it, and it really turned her on to sleep with her boss. We continued to fornicate but kept it on the down-low, of course, because of our work relationship.

What really sounded like fun to me was having sex at the office. Kaitlyn and I succeeded at that feat just a few weeks into our new relationship. It was pretty easy to pull off fucking at our place of work since Tommy and I ran the place. I could go in anytime, whether after hours or on a weekend, and take in whomever I wanted and do whatever I wanted since I had to answer to no one.

The first few times we did it in the office, Kaitlyn and I banged over my desk, doing all the traditional positions, such as bending her over or laying her on her back with her legs over my shoulders or my back on the desk while she rode me. We almost always dressed office appropriate, i.e., dress shirts and ties for me, while she sported skirts and high heels. Eventually, we moved on to fucking in the conference room as we continued to regularly fuck at the office.

It was a dream come true, and we remained undetected for about a year. One night, however, as Kaitlyn and I were cleaning up from an especially intense session in my office, we heard some noise by the front entrance and realized we had company. While Kaitlyn hid in my office, I went out to check out the commotion under the guise of stopping in late to pick up something I'd mistakenly left at work. I wasn't too surprised to see Tommy. I was indeed surprised to see Laura with him, a girl who worked in Tommy's department.

From there, Tommy and I found some rare common ground: we both liked having a cute chick on our payroll that we could bang in the office. I found out he had fucked two different girls on his staff in the past couple months alone, and we kind of got a laugh out of the fact that we'd both been doing the same thing for a while now and getting away with it. Now that we realized that we were both doing the same thing, the paranoia of being caught was all but gone.

I continued my sexual relationship with Kaitlyn for just a couple months after encountering Tommy that night, but during those months, Tommy and I socialized a lot more. While before our conversations had been strictly about work almost 100 percent of the time, the dominating topic became our sexual conquests. Tommy wasn't one to be tied down, as he told of exploits with a few different women. All of my stories were about Kaitlyn at first, since I was a pretty strict monogamous at the time, but then something happened that caused me to consider expanding my horizons.

Eventually, I found out Kaitlyn had slept with a friend of a friend of mine, and I just didn't have it in me to continue on with her. To be honest, though, I was kind of relieved to have a way out. Even though Tommy knew about Kaitlyn and me, Kaitlyn had insisted on keeping our office romance a secret, and I wasn't completely on board. At the end of the day, I realized Kaitlyn just liked getting nailed by her boss and that I really just wanted to move on anyway.

Kaitlyn worked for the company for a few more months after we stopped seeing each other and then got a job elsewhere. It was just as well. We remained friends but had to constantly pretend that there was no tension between us.

Once Kaitlyn put in her two-weeks notice, I went right to work on hiring a replacement, which is where Tommy became a help. He'd interviewed a girl named Abigail but didn't hire her because someone else was simply more qualified, and his department needed more than what Abigail could provide. When I asked Tommy what made Abigail qualified to work for my department after failing to join his, he surprised me with the honesty of his answer.

"Because she's super cute, and we can fuck her." He sold her qualifications a little short, to be fair. I did interview Abigail, and she was a sharp, young girl who was still finishing college. She didn't have all the qualifications Tommy likes to look for, but my philosophy has always been to hire people who are willing to work hard and let them grow into the roles that you need. Oh, and Abigail was indeed a super cute girl with long, straight light-brown hair, glowing green eyes and a pale, thin, 5'5" frame Tommy and I did end up fucking her, in fact. A lot.

Like Kaitlyn, Abigail too was turned on by being fucked by the boss, and she developed an instant crush on me. Within two months of hiring her, I was nailing her on the regular, most of the time at the office after hours, just like I had done with Kaitlyn. I kept Tommy appraised on the development, of course, and he eventually asked for a run with her.

I was OK with sharing Abigail. After all, we weren't exclusive, and she was dating someone pretty steadily as it was. I just didn't know if Abigail wanted to fuck Tommy, as much as Tommy didn't want to hear it. However, it was Abigail, actually, who suggested that Tommy and I team up on her in a single session.

Neither Tommy nor I had group sex experience before Abigail, and we were two fiercely heterosexual men - but a Devil's threesome still sounded like a lot of fun as long as we kept it straight. To be honest, the idea of a male-female-male threesome had always been a fantasy of mine that was really hot, but I thought it was shameful, so I never pursued it. However, Tommy and I knew we would be bullshitting each other to suggest anything other than total willingness to double up on sweet little Miss Abigail.

Threesome sex turned out to be madly hot, even more enjoyable than I'd fantasized. It was a little awkward and uncomfortable at first having another dude present, but once we got Abigail naked and started taking turns fucking her on the conference room table that first time, it was wild. It helped a lot that Tommy and I were little more than work associates; it really eliminated any lingering awkwardness. To cap the threesome off, we split-roast Abigail on the table, switching ends every few minutes before we dropped two loads of cum on her pretty grinning face.

Tommy and I shared Abigail for about a month and a half. We mostly took turns with her but often finished up our sessions by having her pleasure us simultaneously, with one of us in her pussy while the other enjoyed her mouth, hand or tits. The more threesomes we had, the more of them I wanted. After teaming up with Tommy only three or four times, I hardly desired one-on-one sex with Abigail at all. If she wasn't pleasuring two cocks in one sitting, it wasn't really worth it to me anymore.

When it came to group sex, what had really turned me on for several years now was double penetration; specifically, one cock in a girl's pussy while another man filled her asshole at the same time. There was something about a sexy girl's being sandwiched and dominated by two guys at once that I thought was super hot and incomparable to any other sexual act. My threesomes with Abigail helped me finally get over the shame of admitting my fantasy to the point where I comfortably proposed it to Tommy with Abigail. He agreed that it would be hot and was on board to present the idea to the girl.

To my delight, Abigail was initially willing to give double penetration a try. However, after researching the subject, she got nervous and backed out. The facts she gathered made her really nervous about the pain she'd experience to the point where she simply couldn't agree to it. Tommy and I certainly didn't press the issue with her since she was an employee of our company, and we were already doing some pretty questionable stuff as it was. Therefore, we took DP off the table for Abigail's sake.

Not long after the failed attempt at a sandwich threesome, Abigail's relationship with her boyfriend moved on to the next level, and her sessions with Tommy and me became fewer and fewer until they were non-existent. Abigail remained in the company, but those blissful two-on-one episodes became a thing of the past. Her raunchy experiences with her bosses stayed as simply our dirty little secret.

Tommy and I, though still not real friends in the true sense of the word, continued to casually discuss our sexual exploits with each other, but as far as picking up hot tail among our workforce, we had both hit kind of a dry patch. We didn't share another girl either for a while, but when we finally did, all our other conquests paled in comparison to what we would pull off this time.

* * *

"I think I got our next specimen," Tommy said to me one afternoon. I knew he had been interviewing someone but I didn't see the candidate. "She's smart as a whip and totally qualified, but she's hot too, in her early 30 and totally flirty. I think she'll break in just nicely."

I didn't ask any questions, though I probably should have. I was excited at the prospect of having another potential work slut in the fold but, it was Friday and, in the moment, I had other things on my mind. Instead of gathering more details about our soon-to-be new employee, I just said, "Sounds great, Tommy. Get her on the payroll, and we'll give her our payload."

Another benefit to running our own company was our control over human resources. Instead of miles of red tape that made hiring someone take weeks, we could have new employees starting in mere days. At the close of business the following Monday, Tommy told me that the new girl started the next day. At that point, I asked him to tell me more about her.

She was indeed impressive. She had gone through graduate school and had held some pretty good jobs over the years. "Why do you think she's looking for work here?" I asked.

"I guess she had some sort of moral dilemma at the last place she was working," Tommy said. "It doesn't matter to me. I really think she's our next Abigail."

"I hope she'll do even more than Abby did," I responded, a little blood rushing to my cock from just the thought of what could be. "What was she like? How does she look?"

"Long, straight, light-brown hair, like Abigail's, only a lot longer," Tommy,said. "Brown eyes, like a light brown. I think she's got a little Asian in her, actually." This description was starting to sound all too familiar. "I'd say she's about 5'7", give or take an inch. And her rack and ass, bro? Perfect. Plus, she was really funny and flirty, so I think she'll put out for sure, if we play it right."

"Did you say what her name is?" I asked.

"Jessica."

"Dude," I said, my heart stopping, "I think you just hired my ex."

* * *

"Heeeey!" That voice that at one time made my heart leap for joy now rang obnoxiously through the air of my work space. Jessica wasn't 15 minutes into her first day at my company before she found my office. Not that my office was hard to find, but didn't she have more important things to do, such as learn her fucking job? At least she didn't act surprised to see me, since I had been working here during both of our dating stints, but she did act as if there had never been any type of falling out between us. Typical.

"Oh, hey," I said halfheartedly. "I heard you were going to be working here."

"Long time, no talk," she responded, as if, again, nothing had happened. "What have you been up to?"

No matter how curt my responses to Jessica were, she continued to chatter. For someone who had broken up with me twice, she certainly wanted my attention now. Jessica's inane rambling went on for a few minutes until Tommy, recognizing my distress, mercifully pulled Jessica away and gave her instructions to shadow with a gentleman in his department (no, we couldn't hire females exclusively!)

"What are you doing, man?" Tommy said to me, sounding slightly angry.

"What do you mean?" I answered, legitimately confused.

Tommy closed my door. "We're not going to double-fuck that girl if you're blowing her off like that! Don't mess this up!"

"Seriously, Tom?" I was getting frustrated now. "That's my ex-girlfriend!" I knew right away I needed to lower my voice before I continued. "That bitch hurt me bad, twice. Excuse me for wanting nothing to do with her, but I can't act like nothing ever happened."

"Uh, duh," Tommy said. "Of course. I'm not asking you to fall for her again. Don't you want to double-team her, though?"

"Not really. Not her."

"And why not? Dude, that makes her all the more perfect a prospect. Isn't there any part of that bitterness that would like to just give it to her and leave, just vent out all that anger?"

I got quieter. "I'd never really thought of it that way."

"Now imagine if we both fucked her, like Abigail, only with Jessica it would be merciless. We could even sandwich her. How satisfying would that be for you?"

My cock was getting hard just thinking about double-penetrating Jessica during rough grudge sex. "That would actually be really hot . . .," I trailed off.

"Darn right!" he said. "So don't blow this!"

It then dawned on me that Tommy was talking like a crazy person. "Like she'd go for that!" I countered. "As if she's trying to get back in my pants anyway, let alone let me bring you in."

"I think she misses you," Tommy offered. "I think she misses the attention you used to give her and I bet, for a small window of opportunity anyway, she let's you get what you want." It all made sense to me now. If I pursued Jessica a third time, it didn't matter if she grew bored of me again. All the better, actually. I just needed to keep her attention long enough to live out my dirtiest fantasy with her. If that fantasy ever were to happen, this opportunity was my best chance.

* * *

My bed creaked loudly beneath us, drowning out our moans of pleasure as my cock began to swell up inside that tight, wet pussy that I had missed more than I realized. The smell of sweat and sex surrounded us in that warm room as more than half an hour of intercourse neared its end. It was only the beginning of releasing my bitterness.

"Cum wherever you want, baby!" Jessica shouted as I thrust into her just a couple more times, nice and hard until my cock was nearly erupting inside her. I pulled out of her cunt, holding myself up by one arm while using my free hand to stroke my cock, which ejaculated instantly while Jessica cried out with delight as she lay on her back on my bed, her legs falling to the mattress after being wrapped around my waist. My first spurt of cum streaked across Jessica's right shoulder, and then I got better control over my aim and unloaded the rest of my man juice on her perfect boobs. "Oh yes," Jessica said amid her deep breaths, "that's so hot!"

As soon as my cock was spent, I pushed myself all the way up and started to catch my breath as I knelt between Jessica's legs and admired the big load with which I had generously doused those big boobs of hers. Then my eyes traveled up and down the rest of her sweating, panting naked body, which I'd also missed. Having sex with Jessica that night had been really fun, but it was the first time I had ever been intimate with someone for whom I felt such disdain.

Tommy had been right: Jessica, ever the attention whore, had been feeling pretty lonely lately and missed the companionship she had with me. The "moral dilemma" at her old job was accurate, according to Jessica, but she chose to apply at my company solely because of me. She didn't come right out and offer those details, but she said it in so many words. I took Tommy's advice and let Jessica in, although it was against my every impulse. I knew it wouldn't be long until she got used to me again and left me anyway, so I moved fast. I had fucked her within two weeks of her start date.

As we recovered from, I have to say, really good sex, Jessica started to clean off her boobs as she asked, "So my boss wants to screw me too, huh?" Yes, I had told her that much.

"He was saying from the day he interviewed you that he thought you were hot. It wouldn't be the first time he and I were hitting the same girl."

"Really?" Jessica said, her eyes wide as she sat up and began to dress. It was a Saturday afternoon, and we had the whole day ahead of us still. "I thought you guys weren't that close."

"We're not," I clarified, "but that didn't stop us from tag-teaming a girl that worked for us." I paused and then went for it, not giving Jessica the chance to respond, "Would you go for that?"