An unfortunate hiring leads to the best possible payback.
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?"
The look on Jessica's face morphed from surprised to sinister after a brief moment of silence. "Sure!" she said, appearing eager to please me as she pulled her shirt back on. "If you've done it before, then why not? That sounds like a lot of fun!"
It was just like Tommy had said it would be and almost too easy.
* * *
Unlike with Abigail, I was proactive this time with suggesting double penetration, which really was a deal-breaker for me. Instead of letting Jessica do her own research on the subject and risk her becoming unnerved, I looked some things up myself to see the plausibility of such a dastardly act that had always turned me on but that I had never actually done. I was discouraged at first by the lack of real and positive information on DP, not so much because I was concerned for Jessica's well being but because I wanted to have something to show her that would convince her to willingly go through with it. I was also starting to grow worried that DP was just something that looked hot in porn but didn't really work in real life for anyone but pornstars.
At last, I came across a website wherein a girl laid out tips for a male-female-male sandwich, promising, if followed, intense enjoyment for not just the men but the woman as well. I printed out the webpage and brought it to work the very next day. Around lunchtime, I strolled over to the other side of the office to where Jessica was hard at work. I'd noticed that having such little respect for this woman actually made it easier to trap her into Tommy and my plan. In this instance, I had no real trouble making the proposition to her. I can't imagine even suggesting such a thing with a girl I actually respected.
"I've been doing a little research into the activity we have planned for this weekend," I said to Jessica, who was just finishing up some paperwork before she dug into the salad that was on her desk. "I came across some interesting ideas. What do you think of this?"
Jessica took the paper from my hand and began to read it. She was silent at first, an inquisitive expression on her face. She didn't seem surprised or startled by what she was reading, though; rather, it appeared that she was taking it very seriously, reading the page and considering her options.
"Is this something you'd be comfortable doing?" she asked, at this point communicating some incredulity.
"Definitely," I said confidently. "I think it would be a lot of fun, if we did it right."
"You'd be comfortable being that close to . . . you know . . .," she then whispered just in case anyone could hear us, "Tom?"
"I've considered all the pros and cons," I responded. "And, trust me, he's on board if you are."
"Let me think about it," Jessica said. "I've done, you know," she whispered the next word as well "anal." That fact was a new tidbit for me that excited me because it made my proposition more likely, even if only slightly. "But I've never done it like this," Jessica finally finished.
"Take all the time you need," I said, "but just let one of us know by the end of tomorrow." I left Jessica to her salad and made my way back to my office. By the time I had grabbed my own lunch, I was gripped by anxiety that I was making it too easy for Jessica to refuse something on which I had set my heart. Before I finished my sandwich, I decided to text Jessica, which allowed me to be less discreet. "Honestly," I texted, "after reading into it, I see no reason to not give it a try. I think DP is really hot. Wouldn't you like being the center-of-attention like that? I think you'd be really sexy." I felt bad for pressuring her, but all I needed to do was remind myself of what a bitch Jessica had been to me, and I was OK with myself.
Not even a minute later, my phone buzzed. My hand shook with excitement as I grabbed the device, almost knocking over my bottle of water as I reached. "What the hell," the text read. "If you think it will be fun, then why not?" My heart leaped in my chest from excitement before another message came through: "I agree with you, actually - it sounds really, really hot!"
"Let me go tell Tommy the good news," I texted back, glad that she couldn't see my excessive excitement or the boner in my pants. Then, almost as soon as my text was delivered, another response came through.
"Do you want to hang out tonight? I have something in mind."
* * *
We were both panting heavily. Jessica was positioned in front of me on her hands and knees with her ass facing me. She twitched her neck to fling her long, brown hair over her shoulder and out of her face so she could watch me as I tried something that was new for me but not for Jessica. With those brown eyes intently looking at my erect cock, which was hanging free, I used both of my hands to spread Jessica's ass as wide as I could.
"Just do it," Jessica said between breaths. "Just do it, baby. I want you to." I leaned forward, my sprung cock poking at the dark, unfamiliar hole of my ex-girlfriend. Once I had steadied my tip between Jessica's ass cheeks, I took one hand off Jess's butt and held my cock instead. As soon as I had leverage, I very slowly pushed forward, sinking just the head of my penis into the girl's asshole.
Letting out short, forced breaths, Jessica became rigid and continued to watch me over her shoulder as I entered her through the back door. All of my instincts told me to be gentle, since I can only imagine how rough anal sex can be. However, after I had inserted another inch or so of my prick into Jessica's tight, tight hole, I remembered my lack of concern for this particular girl.
Jessica screamed and tensed even more once I suddenly and selfishly shoved the rest of my length into her shitter. She didn't scold me or complain - we both knew she was in no position to complain. Now with both hands on Jessica's ass again, I ground my hips up against her, bottoming out in her lubricated ass, pressing my balls against her taint, just above the hole with which I was much more acquainted.
From there, I held on firmly to Jessica's ass and began to thrust back and forth, in and out of her ass. How constricted it was dominated my thinking as I fucked it. I had screwed my fair share of tight cunts, but nothing like this asshole. I moaned without filter and shamelessly pounded that bitch's was without mercy, taking only a moment to adjust to the sensations of Jessica's raw anal walls before just going to town on it.
Jessica managed to put a lid on her cursing and crying after a minute or two and then just took the ass-fucking like the whore she is. She straightened her back and looked forward, holding herself up on her hands and knees and appearing more comfortable as she adjusted to the situation to which she had willingly submitted. I railed her in the ass to my heart's content until, at last I felt my cock begin to swell. Undeterred, I relentless thrust in and out of her until I nutted in my ex's ass.
Jessica cried out with what sounded like a mix of surprise and amusement as I unleashed my entire load in her rectum. When I finally pulled my cock out of Jessica's butt, a trail of cum dribbled out as well. As I caught my breath, I asked her if she wanted to taste her ass. I gave her the options since I figured a little mercy might go a long way. She declined, which was OK. She wouldn't have the luxury of declining anything once Tommy and I had our way with her in a few nights.
* * *
Jessica had tested and proved her ass and now was ready for the main event. Even after the rough ride I'd given her, she still appeared eager to go ahead with Tommy and my depraved plan. It was even her suggestion that we not have sex again until the big night so that I could save up my load for her. For that reason, I was happy to abstain from any sexual action for the next few days and advised Tommy to do the same.
Since it was so late in December by the time we were ready to go, we intentionally set the date of the threesome for December 31, New Year's Eve. None of us had any obligations that evening, so we all planned to ring in the new year together in the hottest way possible. If it went according to plan, Tommy and I would be plugging up my ex-girlfriend right at the turn of 2016.
For the first time, Tommy and I closed the office on New Year's Eve. The day off would give Jessica the day to rest up and mentally prepare, while Tommy and I would have been too distracted to get any work done anyway. Our other employees, of course, were just happy to have the day off, so there was no questioning the somewhat unusual closing.
Tommy met me at the office around 10:30 pm. I had been there for half an hour already. I was too excited thinking about the threesome to do anything else leading up to it, so I had shown up early and made sure everything was straightened out and in order. By the time Tommy arrived, his help wasn't even needed. He was greeted by a fully cleaned and prepared conference room, complete with wine, some light snacks and a big clock that would let us know when it was the new year.
Once Tommy was there, we both sat in the conference room and waited for Jessica's call to let us know she was in the parking lot. We were both pretty excited to be teaming up on a girl for the first time in a long time and really eager to try our first double penetration. For me, it was an especially satisfying evening as I would be fully venting my remaining frustration and bitterness toward my ex-girlfriend. Honestly, after tonight, everything she had done to me would be all worth it.
True to form for most females, Jessica was about 15 minutes late. It felt more like an hour to us horny guys who were agonizing over finally getting things started. My heart was beginning to sink as I thought that she wouldn't show, which wouldn't have totally surprised me. Finally, my phone vibrated to indicate that my co-worker had arrived.
"Let me in!" was all she said when I answered, and she hung up. I immediately made my way to the front door, where I could see through the glass that Jessica was waiting in a long, heavy coat that covered almost all of her body. What I could see was that her hair hung straight down and that she was wearing black high heels, even though it was snowing and a little icy outside.
I opened the door, greeted by a blast of cold air and a hot brunette. In that moment as we anticipated the raunchy fun we had planned, I almost forgot my disdain for this girl, and it actually kind of warmed my heart to see her. Also, while I'd always thought she was beautiful even though I hated her for most of the time I'd known her, Jessica seemed to be getting prettier and prettier lately. I couldn't wait to see what was beneath that long jacket.
Jessica did her usual small talk, acting as if she were oblivious to what was going on, kind of like how after a month since reconnecting with me, she'd yet to indicate any awareness at all of our past relationship. It didn't matter anymore, though. Tonight would be a night I would remember for the rest of my life. Once Jessica let me fulfill this fantasy, I could consider us even.
I led the young woman into the conference room where Tommy was, and Jess was delighted by the setup in there. Tommy had a glass of wine ready for her before she even began to take off her jacket. I realized, as much as I wanted what was about to transpire, it was a little depraved even for me and that a drink or two might not be a bad idea to help take that edge off.
The first glass of wine I poured ended up spilling mostly on the floor because of my shaking hand due to the fact that right then Jessica took her coat off. I didn't expect her to catch me very much off guard, since I had already seen her naked and nailed her a bunch of times, not to mention fucked her ass even. However, out of those several times we'd been intimate, Jessica had never dressed up for me - until tonight.
As Jessica hung her coat on the back of one of the chairs by the table, I hardly paid notice to the alcohol I had wasted on the floor while I took in the arousing specimen before me. Jessica stood erect and threw her hair back as if to subtly display what she was offering tonight, which was her thin, curved frame that she had draped in a sexy blue dress. The garment hung from her shoulders by two thin straps. It was very low cut, showing off Jessica's boobs, which were pressed together and practically falling out. From there, the dress clung to her hips and tapered off about halfway down her thighs. To accentuate the outfit, Jessica sported four-inch black heels, a pearl necklace and two silver bracelets on her right wrist.
"Damn, girl," I said. "You never dressed up like this for me before."
"I've never had to please two men at once before," she answered as she had her first drink.
"And one of them is your boss, remember," Tommy chimed in, taking a drink himself. Then, wasting no time, he stepped behind the girl, running one arm down her side to her thigh. Looking at me he said, "How about we get this lady a seat and some more to drink?"
Grabbing the wine and first finally pouring myself a glass without spilling it, I made my way toward Jessica and Tommy. I quickly imbibed my first drink and then poured myself another, setting it down on the table along with the wine bottle before pulling a chair out from the table for Jessica. The chair didn't have wheels on it or anything, so it would work for what we had planned. Once the chair was positioned against the wall, I took Jessica's empty wine glass and filled it up again, handing it back to her. I, too, took another drink, which would be just the right amount to eliminate my inhibitions while not getting silly.
The clock showed us it that there were only 20 minutes left in 2015, so we had to move on with our plan if we were going to both be inside Jessica at the turn of the year. Tommy and I, of course, were already sporting large bulges in our pants, so without further delay, we started to undress. We had dressed up as well, wearing office attire, including dress pants, button-down shirts and ties, but those pants were coming off now, along with our boxers. Jessica squealed with delight as these two boners approached her. As soon as I was close enough, Jessica grabbed my tie first and looked up at me with those pretty brown eyes. For a moment, I began to feel my fondness for my ex-girlfriend return.
Jessica didn't say a word, and I caught myself no longer looking into her eyes with fondness but now down her dress with lust. Meanwhile, Tommy stepped up on Jessica's right and grabbed her wrist, pulling her hand up to his cock. Jessica tore her gaze away from me and grabbed her supervisor's cock, looking up at him and saying, "Is this what you want, boss?" Tommy just sighed with pleasure as his employee began to stroke his stiff erection. She then looked back at me. "How about you, lover?"
The feeling of Jessica's soft hand sliding up and down my shaft made me not even care that she had referred to me as her lover. I just sighed and watched on as Jessica beat us both off at once. I first ran my hand through her soft, golden brown hair and then decided to pull the strap of her dress past her shoulder, which revealed a little more of her left boob. Tommy saw what I did and followed suit, only he didn't just push the strap down but used two hands to follow up by pushing the dress down past Jessica's large tits so that they both fell out and were exposed.
"No bra," Tommy commented.
Jessica looked at him, smiled and shook her head. Then she leaned forward, putting her head level with Tommy's prick as she stuck her tongue out and began to lick the tip.
Tommy cursed putting both hands on Jessica's head and forcing her to suck him off after just a few seconds of her licking his dong. Meanwhile, she continued to stroke my cock on her other side. For the next couple minutes, Jessica alternated between Tommy and me, sucking our cocks and gently rubbing our balls. Having slept with Jessica many times in the past, I had seen her in her fair share of hot situations. However, none of my past experiences were quite as hot as watching this topless babe go back and forth between sucking two cocks - and we were just warming up.
While I would have loved to have allowed Jessica to continue with the blowjobs, Tommy and I pulled away after just a couple minutes. We were running out of time if we wanted the main course by midnight, and it was more important that we preheat Jessica for what was in store than that she pleasure us. Without hesitation, Jessica briefly stood up to push her dress down the rest of the way, revealing a cute black thong, which also ended up around her ankles with no delay. As Jessica stepped out of the clothing, she quickly unclasped her necklace, at which point I advised her to leave the remaining jewelry on as well as the heels. To my request, Jessica simply smiled, dropped the necklace on top of her dress, and kicked all the discarded clothing aside.
Now nude, save for her shoes and a couple bracelets, Jessica was seated again. The clock read 11:48 pm, so we had really no more than 10 minutes of foreplay with Jessica before we needed to get her into position. At this point, Tommy and I took off the rest of our clothes but stayed on our respective sides of our female employee, who suggestively spread her legs for us as she remained in the chair. Tommy leaned right in and kissed her, squeezing her left boob. I, meanwhile, squatted down and picked up Jessica's heel, bringing the shoe to my face. I started my foreplay by licking the top of Jessica's foot and travelling all the way to her knee. Jessica moaned and quivered a bit while still making out with Tommy as he fondled her breasts.
Next, I lifted Jessica's leg over my head and drew closer to her exposed twat. First, though, I slid my free hand underneath her, searching for her asshole while I rested her leg on my shoulder. I had never fingered a girl's ass before and didn't really want to this time either, but I knew our best shot of getting right to double-fucking Jessica was to work her ass in a bit before putting a dick in there. Jessica gasped when she felt my finger poke her stink but she allowed me to proceed without complaint. As my finger slid inside her, still not really my thing, Jessica put one hand on Tommy's head, which was now sucking her tits, and the other on my head. Her fingers combed through my hair as I began to thrust my finger in and out of her tight butthole.
One finger became two, and then I was ready to lean forward and eat my ex's pussy. Jessica really cried out now as her ass, pussy and tits were all stimulated at the same time. As I licked Jessica's pussy and sucked on her clit, I knew as well as anyone in the room that she was nice and wet, ready to fuck.
With only a few minutes to go until the new year, it was time for the main event. Tommy and I pulled away from Jessica's body and lifted her up from her seat, leading her over to the conference room table. It was wooden but solid and sturdy. Remember that we had been fucking girls in this room for a while now, so all the furniture was purchased with that purpose in mind, even for the most extreme scenarios. This table would be more than capable of supporting all three of us if it needed to do so.
I got up on the table first and lay down, followed by Jessica who hovered over me on her hands and knees. I put one hand on her lower back while holding my cock with the other and aligning it with that wet pussy. Jessica briefly used one hand to help me find her hole and then went back to supporting herself with her hands as she sank down on my cock. We both moaned in unison as Jessica lowered herself until she was on the very base of my cock.
It was almost midnight, so there was no time to work Jessica up to Tommy's entrance. Instead, Jessica's boss stood right up behind her, in between my and her legs as he spread her ass with one hand and steadied his prick with the other. Jessica looked intently over her shoulder while I held her in place and Tommy put one hand on her lower back, pressing his cock against Jessica's alternate entrance. Then I felt it, the head of the other man's cock pushing into the hole adjacent to the one I was filling. It was a weird feeling, but hot more than anything else. While Tommy and I were straight guys who had never had our parts this close, it wasn't our first time sharing a girl either, so neither one of us felt very awkward.
Jessica laughed and began to mutter something as I felt a little more of Tommy's dick penetrate her, but she was cut short as soon as the other man thrust forward suddenly. I could sense Tommy's dick sink all the way into Jessica's ass, at which point the bitch gasped and collapsed on top of me, burying her face in my shoulder as she adjusted to what was the first double-penetration experience for all of us. As Jessica remained still and silent on top of me, Tommy slid his hands up her back until he was holding onto her shoulder. Meanwhile, I held the girl in place at her hips while Tommy and I got ready to give this girl a fucking like she'd never had before.
My mouth went dry, and my heart pounded in my chest as it began to sink in that I was finally living out my dirtiest, most debauched and shameful fantasy as I was balls deep inside a hot girl's pussy while another man filled her ass. The fact that I was simultaneously venting my remaining bitterness toward my ex was just a bonus. As Tommy and I ground up against the still bitch's body, we took a few seconds to adjust to the tight confines and then proceeded to double-fuck Jessica.
Tommy got going first, thrusting confidently in and out of Jessica's ass while Jessica remained silent, no doubt feeling a great deal of discomfort from being double-filled for the first time. I turned my head to face her and saw, even with her face buried in my shoulder and her hair obstructing most of my view, that her eyes were winced shut and her teeth were clenched. I considered mercifully kissing her and maybe whispering in her ear or something, but the residual bitterness from our past relationship won out and filled me with satisfaction.
As I looked at my ex-lover, she suddenly sprung up, her hair flying around as she held her head up and hovered over me again. A smile then crept across her face, and she said, "Happy New Year!" Our plan to double-penetrate my ex at the turn of the year had been successful.
"Happy New Year, bitch," I said back to her as I began to thrust up harder into her pussy. At the same time, Tommy began to pound Jessica's ass powerfully, and Jessica, still smiling, lowered her head back down, her soft hair falling in my face as she looked down at me and took both cocks in her other end.
After just a minute or so, Tommy and I got into a rhythm where I sank into Jessica's twat once Tommy pulled back in her ass and vice versa. It made the whole experience more endurable for Jessica, but it wasn't her comfort with which we were concerned. Taking turns in her holes actually made it easier and, in a way, hotter for us guys as we plundered her at the same time.
Once we got going, Jessica began letting out one brief moan after another. Every few seconds she would throw her head up, causing her beautiful hair to flash about as Tommy and I rocked her sexy body back and forth with our thrusts, plummeting us deeper into depravity with each passing moment. Her perfect boobs hung over my chest as her moans grew louder and louder. As more time passed, it seemed like her noises progressively indicated pleasure more than pain. While I had no intention to please my ex-girlfriend, the thought that slut was enjoying it made the whole experience even hotter.
Tommy and I were now steadily sawing in and out of Jessica as the sturdy table creaked slightly but continued to support us. We were all breathing pretty heavily too, and the sound of male flesh slapping against Jessica also added to the audio. The dominant sound, however, was Jessica's moaning, which got louder and more and more constant as the sinful, shameful activity progressed. More turned on than ever before in my life, I thrust harder and faster into my former lover while her boss matched my pace almost instantaneously.
"OK," Jessica said with a laugh, breaking the silence, "a little slower." She held herself up halfway between our thrusting bodies, clearly oblivious to our lack of concern for her well being.
"I'm the boss, bitch," Tommy said, "not you." He continued to fuck her ass hard and relentlessly, and I did the same in her tight, wet cunt. Jessica once again collapsed on top of me, accepting her fate as she buried her face for a second time. Her laughs turned to moans which began to sound like hopeless groans. Unsympathetic, I wrapped my arms around her waist, and Tommy held tightly to her thighs as we continued to take turns inside her holes, our balls alternating between slapping against her taint as we rocked her body back and forth, filling both of her holes as we mercilessly fucked her.
Jessica was now holding onto my shoulders, her moans filling my ears. After a minute or so of our rough treatment of her, she seemed to calm down a bit, although we didn't change the pace or force with which we were screwing her. Jessica let out one particularly loud moan that sounded more like pleasure than pain, but her head remained pressed against my shoulder for just a moment longer. At last, she pushed herself up again, her hands still tense and her fingernails clawing at the table, but she straightened out her back and accepted what was happening to her as Tommy and I slammed in and out of her ass and pussy simultaneously.
Another minute passed, and Jessica's cries became more high-pitched as she was rocked back and forth by us guys. Tommy remained upright behind her as he held her by the thighs and pummeled her ass. Meanwhile, I gripped Jessica's sides and looked into her eyes while pushing up into her cunt. Most of the time, Jessica had her head down near mine, and every time our eyes met, she would smile as she moaned. Once in a while, she would lift her head confidently and look straight ahead as we persistently stuffed both of her holes.
Tommy and I began to grunt louder, and the sounds of Jessica's holes' squelching joined the audio of the moans of our girl, the slapping of flesh and the creaking of the table beneath us. Jessica's cries became even higher and more deliberate, her body helplessly pushed back and forth by our thrusting male bodies. Still crying out, Jessica tucked her head near my chest again. I think she was sincerely enjoying her predicament for a while there, but now it seemed that she was reaching the end of her rope. It didn't matter to us boys, though, who kept on ravaging her as she rocked and thrashed between us.
Jessica's cries began to sound like those of an animal, and I remembered in my research how it said the girl might make odd noises after being double-penetrated for a while. In response, Tommy and I focused less on shoving our whole lengths in and out of Jessica and more on just pounding her hard and fast, which really made her cry out. We nailed her tight holes in that manner for a minute or so before going back to steadily rocking her back and forth.
More than a couple times I thought Jessica would beg us to stop, but each time she regained her composure and pressed on. I couldn't help but admire her for her stamina. The idea had been to give her one good depraved fucking and then leave her, but I was starting to think I could be onto something here with her. As Tommy and I relentlessly sawed in and out of our employee, she continued to moan, deeper and more labored. Every few seconds she threw her head back, causing her hair to fly up near Tommy's face. She was breathing hard and now coated in sweat. I'd never seen anything sexier in my life.
One of my anxieties going into my first double-penetration threesome was a quick trigger. However, my cock was holding in my load unbelievably well, as if it too wanted this experience to last forever. However, after a while, I knew I couldn't hold off cumming much longer. As I realized it was time to decide what to do with my climax, Jessica had finally reached her limit and begged us to stop.
"OK," she gasped at last, "I can't do this anymore," and laughed. While neither one of us guys really cared how much Jessica felt she could take, I know I, at least, was on the verge of erupting, so a break to hold off my orgasm wasn't a bad idea. Sure, we could have banked on having two orgasms each, but it was already late, and we'd be getting tired pretty soon. Neither one of us wanted to be finished just yet.
As Jessica caught her breath, Tommy slowly slid out of her ass and stepped away. Then Jessica got to her knees and pulled herself off me before rolling over and lying on the table for a few seconds while I got up as well. We offered Jessica the opportunity to freshen up in the bathroom, and she took us up on it. Still wearing nothing but her heels and the bracelets on her wrists, Jessica strutted out of the conference room and down the hall.
"Holy hell," I said. "Was that hot or what?"
"Unbelievable," Tommy said, catching his breath.
"We're not done DP-ing her, right?" I said to Tommy once Jessica was out of earshot.
"Hell no," he said. "I may never be done DP-ing that girl." We then sat down and waited about 15 minutes before Jessica finally returned. She had definitely cleaned herself up, as the sweat was gone, her hair was fixed and she had reapplied her makeup. She explained she had a kit at her desk.
"Did you like your first DP?" Tommy asked her.
Smiling as she sat down in another chair, she nodded in the affirmative.
"Ready for round two?" Tommy said. A look of hesitation briefly crossed Jessica's face, as certainly she had endured her share of discomfort already and was probably sore now, leaving her little, if any, desire to take it in both holes again. She didn't know, of course, that she had no choice, but it was fun to let her think she did. We knew she would consent. She wouldn't have been here tonight if she wasn't going to go along with anything we wanted.
Surely enough, within a minute, Tommy was lying on his back on the table now while Jessica joined him. Initially she began to get to her hands and knees again, but Tommy and I flipped her around so that she was facing the ceiling this time. We explained to her that we were going to do it the other way now. We knew it would likely be more uncomfortable for her, but it would be hot as hell for us.
Jessica breathed harder once Tommy lowered her on his dick, impaling her ass. He'd be getting the butt again because it was better fitted for him, and switching between the ass and pussy wasn't a good idea, I'd read. Also, I really wanted to be on top and in my ex's pussy while we sandwiched her.
With little resistance, Jessica sank down to her boss's balls. Then, propping herself up with her arms behind her, she looked at me, her chest heaving up and down as she lifted and spread her legs, presenting her shimmering open vagina that needed to be filled. I stepped up on the table with the other two, the piece of furniture easily supporting the weight of all of us just like I knew it would. Then I stepped between Jessica's outstretched legs, her heels pointing toward the ceiling, and lay down on top of her, guiding my cock into sweet center of sin.
Even with the neighboring hole stuffed to capacity, I didn't have much trouble slipping my member all the way into Jessica's cunt. It was tight of course but very wet and very eager to take me in. As I slid down between Jessica's legs, I lay down on her stomach and chest, sinking my cock into her wonderful pussy as I put one hand on her stomach and the other on her shoulder. My cock slid all the way inside my ex while her boss underneath her held her by the ass and spread both of her holes to give us full access to her sexy body.
Once we were both balls-deep inside Jessica, she cried out and never stopped moaning after that first noise. While Tommy and I were still adjusting to both being inside the same woman again, Jessica lay down, her back now against Tommy's chest while my chest was pressed against her boobs. I now had my right hand on the table while the other remained on her stomach. Beneath us, Tommy still held Jessica's ass cheeks. At last, Jessica was sandwiched firmly between us.
We began to fuck Jessica again, and the rhythm came back to us right away. Tommy and I were sawing in and out of Jessica in no time, alternating with each other as each of us filled his respective hole. Jessica's right hand shot out and grabbed my back as I started to thrust in and out of her pussy. I could feel her nails sink in my back as well as the cool metal of the bracelets against my flesh. Her other hand appeared to be on Tommy's, which was on her ass.
Jessica's legs remained straight up for just a few seconds and then bent at the knees and hung in the air, her thighs resting on my hips as I used all my might to fuck her cunt. From this angle, it was harder to avoid incidental contact with Tommy's thighs, but both of us boys hardly noticed any occasional male-on-male contact because we were having the time of our lives as we fucked this hot girl. As more time elapsed, we simultaneously railed her ass and pussy harder and faster, keeping the squirming bitch pinned tightly between us as we enjoyed our hot Jessica sandwich.
My cock took turns with Tommy's going inside my ex-girlfriend, I in her pussy and he in her ass. We went in and out of her relentlessly as she thrashed and writhed between us, moaning louder and louder as we continued. This time, Jessica was either really enjoying being sandwiched or just didn't bother to voice any discomfort. I couldn't tell either way, but perhaps she was catching on that we intended to treat her sexy body roughly.
We were all breathing heavily and sweating profusely. Jessica, in particular, was glimmering in the light of the office with her own sweat and that of two other people. As I fucked Jessica's pussy, I occasionally looked over my shoulder to see her sexy legs propped up in the air, bouncing with each of my thrusts into her cunt. How I would have loved to have seen her holes filled and her taint stretched out as she took as much cock as she could handle!
The room was very hot by now. Sweat was dripping down my face and chest, and I was forgetting to breath. I remained positioned over Jessica's left shoulder, her right arm sinking into my back still while Tommy lay beneath her, his head over her other shoulder so that we two men weren't an awkward distraction to each other. Jessica's body rocked between us as we sandwiched her, fucking her holes relentlessly as the girl was practically screaming again, all but drowning out the slapping of damp flesh, Jessica's squelching holes and the creaking of the table beneath us.
It was a miracle that neither Tommy nor I had come yet, but inevitably we reached that point. At last, I said to Tommy, "Ah shit, let's cum on her." With those words, I immediately pulled out of the ravaged, used bitch and jumped off the table. Tommy quickly shoved Jessica off him, and she got on the floor and dropped on her knees without any need for instruction. Tommy joined me in front of Jessica, and we beat off as the girl lifted her head up, closed her eyes and tried to catch her breath.
I cursed out loud as my long-awaited cumshot erupted from my dick, which was pointed straight at Jessica's face. I must have unleashed five or six good hard ropes of cum, all of which plastered Jessica's face. About halfway through my orgasm, Tommy had his own, he too dousing the girl's face while also shooting off a couple spurts at her heaving rack. By the time we were finished, Jessica had the majority of two loads dripping down her nose, cheeks and chin, with a little bit near her eyes and in her hair, while the remainder of our man juice splattered on those gorgeous boobs.
"Holy fuck!" Tommy shouted and then stuck his cock back in Jessica's face for her to clean it up. This time she had no choice but to taste her ass. Once Jessica had sucked his cock for a few seconds, Tommy collapsed in a nearby chair. Jessica hardly reacted to her humiliation, unable to open her eyes because of the cum on them. "That shit just might get you a raise," Tommy added.
Jessica wiped the cum from her eyes and stood up, her eyes appearing to sting a bit. Out of breath and with very few words exchanged, we all cleaned up and got dressed. We straightened out the office a bit, but Tommy and I knew to just come in earlier on Monday to make sure everything was in order.
By the time we had locked up and were in teh parking lot, we had all recovered rather sufficiently, though I can't imagine how sore Jessica was. Still, she was laughing and joking as we walked her to her car. Just moments after the wildest, most fun experience of my life, it was hard to believe that it had actually happened.
* * *
Jessica texted me a lot that weekend, but I responded in a familiar fashion by not responding at all. While part of me wanted nothing more than to pursue a debauched relationship with this girl, I knew I had no future with her. At work the following week, I was polite to her but didn't say much. I had gotten my revenge on her for hurting her and was now ready to move on. I think she got the hint after a few days because she started to keep her distance after awhile - or maybe she would have stopped talking to me after a couple days either way.
Tommy, however, had no reason to separate himself from Jess. Within a couple weeks, the two were pretty much an item. It meant she'd was still in my life for a while, but, like I said, I'd gotten the closure I needed, so I was OK with it.
Then one afternoon, Tommy said to me that he had been considering having another devil's threesome with Jessica but that the girl hadn't been responding to his texts and was even avoiding him at work as much as possible, which is quite a feat since Tommy was still her boss. "That's Jess," I told Tommy. At least I had learned my lesson this time and had gotten out of it what I wanted. I guess some things never do change, but you can make the most of the moments while they last.
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