Office Wager


It was one of those stupid bets that one can only make when one has been drinking with coworkers. Little did I know that it would change not only my life but also the nature of my soul.

"You know, Janice, we have a lot riding on this proposal tomorrow to obtain the Anderson Corporation as a client. If your presentation goes well, we should be in good shape to turn quite a profit next quarter," said Ted, as he downed yet another margarita at the local watering hole near our workplace. "But I don't think you have prepared well enough. I don't think we're going to get this account."

"I feel quite good about it," I added. "So good, in fact, that I would be willing to wager that we will get that account."

"Oh? What kind of wager?" said Ted.

"Well, if we don't get the Anderson account, I will let you guys decide how you want me to pay up, actually. It will be your call. However, if we do get the account, all of you guys will have to sign over your year-end bonuses to me," I replied.

The guys at the table--all five of them--looked at me in measured silence. They knew that I was deadly serious. You see, we all work at an advertising firm, and a portion of our yearly wages come in the form of year-end bonuses. In a good year, the bonuses usually end up being pretty substantial, somewhere around $40, 000 to $50,000 per person. This is usually in addition to our salaries, which vary, but typically are in the $80,000 to $100,000 range. I knew if we secured the marketing agreement with the Anderson Corporation, which was a large overseas retail firm, our company would be making tens of millions of dollars over the next five years. Just securing the contract alone would ensure that everyone received a handsome bonus. If I won the bet, I would be receiving probably anywhere between $200,000 to $250,000, depending on what our board of directors decided the pay out would be.

Besides Ted, who is technically my boss (and who makes far more than the rest of us), the table was also occupied by Mark, Dennis, Robert, and Joe. They work in essentially the same role as I do, which is to design proposals for companies who are looking for someone to design and implement strategies for commercials and print ads to increase their business.

I was pretty new to the company. I also happened to be the only woman in our department. As such, the guys gave me a lot of flirtatious attention, which was nice. However, I also had to work twice as hard to prove myself as a competent professional to these misogynists. As creepy as these guys could occasionally be, I knew they would want to gamble with me. They couldn't resist a good challenge, especially if it came from a lady.

"You are saying that we can choose our prize at our discretion?" asked Mark, clearly interested. His icy blue eyes and short blond hair were lit like candles amidst the reflective light of the restaurant.

"Yeah," I said, half-drunk and not really knowing what I was saying. "You can decide, as long as you are not going to murder me or anything."

"Anything?" added Robert.

"Anything--or just about," I laughed.

"I'm in. What do the rest of you guys think?" asked Dennis, who was quite attractive, with his dark, lean looks. I think he had a secret crush on me, but I wasn't sure.

"Sounds good to me," said Ted. "You just better be ready if you lose. We might make you an offer you can't refuse."

I had no idea what he was talking about. The rest of the guys agreed to the wager as well. We all shook hands at the table. I was very confident that my proposal would go over well. I knew this presentation was going to be a true day of judgment, in more ways than one.

A few days later, I made my presentation for the Anderson Corporation. Let's just say that it didn't go well. They asked several questions for which I had no answers, and the whole meeting was excruciatingly awkward. They felt that the rates we charged were excessive, and that as a company we didn't have the experience to meet their long-term business needs. I tried my best to sell our services and expertise, but it was clear that we were not going to get their account.

The people from Anderson soon informed us that they were going to hire a different advertising firm. I had lost my wager with the guys. I felt bad about losing their business, as it was my first real opportunity to do something good for the company. Later that afternoon, I stopped by the office of my boss Ted.

"Well, you won the wager, fair and square," I said. "So what do I owe you guys?"

"Oh, Janice, don't worry about that right now. We know you are a little depressed about not securing that account. We are too. The guys and I will come up with something so that you can pay your debt to us. After all, you did put us at considerable financial risk with that wager. But we'll come up with something soon. We'll keep you posted."

I didn't hear anything from Ted regarding our wager for the next two weeks. Inwardly, I was beginning to think that they were letting me off the hook. One Friday afternoon, however, I received a call that changed everything.

"Janice," said Ted slyly, "please come to the conference room by my office after work. You have a debt to settle, remember?"

I answered affirmatively, not knowing what this was all about. The guys with whom I work are hard to read sometimes, and this was certainly no exception. Regardless, at 5:00 PM, I made my way to the conference room down the hall, wondering what the guys had in store for me. As I walked through the door, the sight in front of me was absolutely shocking: Mark, Dennis, Robert, Joe, and Ted were standing around the conference table, staring directly at me, with their trousers down and their cocks firmly gripped in their hands. I had never seen so many cocks in one place at one time. The guys were in various states of arousal; some cocks were half-erect and some were fully primed for fucking.

"We've decided that you are going to party with us, Janice," said Ted firmly. "After all, we won the bet fair and square, so it is time for you to indulge us a little. You'll enjoy it, don't worry. You said anything but murder, remember? And what is 'reasonable' is always a matter of perspective."

"You gotta be fucking kidding me," I replied. "I don't know what you guys have in mind, but you are all crazy if you think I'm going to let you do what I think you want to do."

I didn't get a second chance to let another word slip from my trembling lips before both Robert and Joe grabbed me firmly, forced me to the ground, and gagged and blindfolded me. I tried to free myself from their clutches, but it was to no avail. They lifted me from the ground and placed me on my back on the table. Although I was scared about what they were doing, inwardly I knew that everything would be okay.

"Oh, it is okay, Janice," said Ted. "Just relax and enjoy the payoff--our style."

I began to wriggle in an effort to escape, but again, it was no use. I could not overpower them. Blindfolded and gagged, I could only feel several arms and sets of hands grabbing and tugging at my small, wiry, supple frame.

"Don't fight it," said Joe. "Just relax and be a good girl."

Once they had me firmly held down on the table, with my arms pinned outward and my legs spread open, they began to unclothe me. For a brief second, I thought about how undainty I must have looked in my disheveled white blouse, black mini-skirt, and thigh-high stockings, with my legs fully splayed for the crowd. The more I resisted their attempts at control, the harder they pinned me down.

At a certain point, the reality of what was going to transpire started to sink in: I was going to get fucked--by all of them.

"Oh, look at that nice skirt," said Dennis, whose fingers began to probe my inner thighs. "Mmmm, boys, we're gonna have a goood time."

"Yes, indeed," said Mark sardonically. "Now let's take it off so we can get a better look at her. I've always thought that she looked delicious."

Immediately, I felt my entire body being engulfed by several hands: they were unbuttoning my blouse, groping underneath my skirt, and fingering my pussy through my panties. I was being sexually mobbed. I was consumed by fear, yet I could tell that they weren't entirely malevolent. We were actually good friends, even if they were crossing a very personal line with their actions. As rough as they were being, I could sense a modicum of underlying, residual respect. Rather than fight it, I decided to just get it over with and submit. Granted, this was easier to think about than to do, as every impulse in my body told me to fight them. But yes, gradually I resigned myself to the notion that they could gangbang me. It wasn't like I had a choice. Submitting to them would probably be the safest thing to do.

I lifted my ass off the table to help them in removing my skirt. I relaxed my posture the best I could, and shortly thereafter I could feel them loosen their grip on my arms and legs. I whimpered softly though the gag, in an effort to convince them to take it off. My eyes were flooding tears, which dampened the blindfold that helped to oppress me. My blouse was now completely off, so I was lying there in my bra, panties, thigh-high stockings, and red high-heels. Happily, I could hear the guys soon start to deliberate about whether they should remove my blindfold and gag.

"She's alright," said Robert. "Maybe we should keep the blindfold on, but just take off the gag."

"No, let's keep the gag on," said Dennis. "We don't want her calling attention to herself."

"I agree, but let's take off the blindfold. She at least deserves to see us work her over," replied Ted.

With that small kernel of so-called kindness, one of the men took off my blindfold. I soon discovered it was Joe. I could see most of my clothes crumpled on the ground, as well as the maniacal gazes of my crazy coworkers. Unable to scream or plead for leniency, I stayed put.

I knew the party was about to begin.

Robert, whom I did not know very well, looped his fingers around my panties and methodically lowered them down my thighs, over my kneecaps, and off my legs. Simultaneously Joe unfastened my bra and tossed it to the ground. I was fully exposed, with the exception of my red shoes and white, thigh-high stockings, both of which everyone seemed content to leave on me. It must have been a collective fetish or something.

"Oh, look at that pussy," said Robert gleefully, before peering deeply into my eyes. "You are smoothly shaved, Janice. How kinky! Oh, that is lovely, girl."

The guys were casually stroking their cocks, clearly viewing me as a dessert. A part of me knew that this was really horrible, yet a part of me knew that I was going to be okay. It was even a tad thrilling, in truth. They were going to gang fuck me, but I was pretty sure they were not going to hurt me physically. Knowing everyone in the room made it slightly more tolerable than if I were about to be gang fucked by strangers. I would make it through the ordeal. But still, I couldn't help but wonder why they would want to do this to me. And most of the guys had wives and children. How could they do this? As Robert fingered my pussy, the dominant thought running through my head was that I would never understand the male mind for as long as I lived.

"So who gets to go first?" asked Mark, who was prepping his eight-inch, uncircumcised cock with his right hand.

"I think Ted should go first," said Robert. "He's the boss, and he came up with the plan, so he should have her first."

Ted looked at me carefully before responding to the rest of the guys. For a brief moment he looked concerned, and I wondered if he was going to call off the party. However, the look of compassion that adorned his face quickly faded. He began to smile wryly and stepped closer to me, positioning himself between my open thighs.

"Yes, I'd love to go first," he said. "Let me get her ready, though."

He bent down and lightly ran his tongue from the bottom slit of my kitty up towards my clit, never pushing it in too far. His action caused waves of shock--a bizarre combination of pleasure and pure repulsion--to ripple though my body. I fought the urge to be aroused. I didn't want to give them that pleasure. Little by little, his tongue probed me further, which involuntarily caused my juices to start flowing. Fuck, fuck, fuck, I thought. My pussy juices were starting to flow, completely against my will.

"How does she taste?" inquired Dennis.

"She is delicious, my friend," Ted replied, as he resumed feasting upon my dripping slit.

After a minute or two of giving me oral, by which time I was a creamy mess, he stood up and pulled my hips to the edge of the table. He then spat in his hand and began to rub his raging erection. His cock was pretty average in size: six inches with moderate girth. I watched in shock as he positioned his cock to the opening of my pussy and teased me with it, rubbing it repeatedly on the outer slit of my pussy slowly, up and down, up and down . . .

"You're gonna get some girl," he whispered. "Oh yes, you're gonna take it from me. And you're gonna take it from all of us." He really seemed to be getting off on talking dirty to me, as he rubbed his cock on the outside of my pussy. "I'm gonna fuck you, honey. I'm gonna make you take it sooo goood," he gloated.

Then, inch by inch, he slowly pushed his cock in, and began rocking his hips against me rhythmically. I could not believe what was happening. I was being fucked by my boss against my will. I couldn't believe it, yet it was happening. Still, to survive the ordeal, I had to block this event out of my mind and force myself not to believe it. Yes, I had to block this out of my mind. . .

"Yeah, baby!" said Mark in encouragement. "Let the party begin! Rock that pussy, Theodore."

Ted's eyes were closed as he fucked me ever so slowly. He was clearly savoring the sensation of my tight, dripping snatch. Despite the inevitable pleasure of feeling a cock inside me, I was completely horrified as he fucked me in a steady, even tempo. The other guys in the room were quite pleased by the sight, and were cheering him on with each and every thrust.

"You know she likes it. Oh, give that girl some fuck cream, " said Joe, as he stroked his penis to the sight in front of him. I could tell that he very much wanted to be next in line.

Ted wasn't even much of a fuck, to be honest. Within about six minutes, I could feel his muscles begin to tighten and his cock expand. The son of a bitch was about to pop. This was not ideal, as I had recently stopped taking my birth control pills. As he increased his pace, I tried to yell for him to pull out, but with the gag over my mouth, my words didn't come out clearly. No, this fucker was going to cum in me. It was only a few seconds thereafter that I felt his body increase in tension, shortly after which his balls emptied deeply inside of me, in strong, pulsating squirts. The bastard.

"Oh, fuck, ohhh, yessss," he groaned, as he pushed his seeds deeply into my womb. "Oh, fuck, take it like a good girl. Oh, fuck yes."

The whole room erupted in cheers as he blew his load deeply into me, driving his creamy cum as far up into my pussy as his six-inch dick could push it. With the sounds of the cheering around me, I suddenly felt like I was an unwilling whore at a wild frat party. Once Ted had expended himself into me completely, he pulled out slowly, looking dazed and satisfied. Immediately I could feel his cum dripping from my pussy, down the crack of my ass, and onto the table below. It looked like there wasn't going to be much down time to the proceedings, as Joe quickly moved into Ted's place.

"Thanks for warming her up," said Joe. "I don't mind getting sloppy seconds with a pussy that looks this good."

Joe was virtually drooling at having his chance to fuck me. He was stroking his cock and his eyes looked wild like a hyena's. It was a look of rabid masculinity. It was pure primal testosterone and completely irrational. His cock was a little thicker than Ted's, though it was about the same length. It was ready for fucking, as its tip was swollen in a dark, purple hue. He was highly aroused. He pulled my hips toward the edge of the table and positioned himself between my legs. The thick, bulbous head of his penis slowly parted my cum-drenched pussy and--in a fraction of a second--he buried himself into my pussy to the hilt.

"Oh, God, yes," he groaned, with his eyes at half-mast, clearly in ecstasy. "Oh, you feel so fucking good, honey."

My senses were totally jolted; my eyes became as wide as saucers as started fucking me like an animal. I gasped and held on for what felt like dear life. I felt like a piece of fuck meat. Oh, this was going to be difficult. His thrusting was highly unpleasant, and I couldn't push him away, because my arms were pinned down firmly by Dennis and Mark, both of whom were on each side of me. I quickly decided to accept it and just hope that it would be over soon. Happily, the process didn't take too long. Joe was so aroused that he came within three minutes.

"Yes," he whispered, as beads of sweat ran down his anxious face as he emptied himself into my pussy. "Fucking take it . . . yes . . . ."

Upon pulling out, the room once again erupted in cheers. Joe's face relaxed into a wicked smile. He clearly had enjoyed himself--and me.

"Nice show, Joe," said Dennis, who now appeared anxious to have his turn with me.

After he pulled out, Joe stood there to watch (proudly, I might add) his seed drip from my well-worked pussy. He reached down, scooped up some of the jizz, and massaged it into my breasts "Oh, you look so good covered in cum, baby. Don't worry--a little protein is good for the skin--and the pussy."

Robert was next. He was the least attractive of the bunch, with slightly crooked teeth and a moderately musty odor about him. He also had greasy hair and a bad comb-over. Like the others before him, he soon pulled my hips to the edge of the table, and began stroking his cock in preparation of the fuck of his life. After all, I probably had the nicest pussy he ever had the opportunity to fuck. I had seen pictures of his wife, and let's just say that she is not a real looker. Robert pulled open a condom, which I was very glad to see. Evidently he was afraid of catching a STD from either me or from one of the other guys. He struggled a little in fitting the condom over the shaft of his penis, but soon he was ready for action.

With a moderate push, Robert's cock was soon fully into me. Of the men who had fucked me to this point, Robert was clearly the lamest. His cock was average in length and very thin. Granted, I didn't mind so much, because I didn't want him fucking me anyway. He pumped into me lamely, grunting with nervous sexual energy. His eyes were focused solely on the sight of his cock thrusting into my tight pussy--he did not even make eye contact with me once.

I think he didn't really want me; he just wanted my pussy. Oh yes, I thought, he wanted to fuck a pussy that was as pretty as those in the girly magazines to which he probably masturbated as a kid (or as an adult). Yes, he was the nerd who never had the chance to fuck as pussy as nice as mine, and now he was getting his opportunity. I thought to myself, I hope you enjoy it, you fucking piece of shit.

After ten long minutes, Robert shuddered to a weak orgasm, thankfully. This left only two more guys: Dennis and Mark. From the look on their faces, they clearly had a different plan for me.

"Hey Dennis," said Mark. "Let's share her."

"You mean a DP?"

"Yeah, I'll take her ass while you take her cunt," said Mark.

Dennis agreed, and got down on the floor while the other guys lifted me off the table and placed me on top of him. Dennis carefully slid his cock, which was enormous (eight inches and as thick as a brick), into my pussy, which was now sore from taking repeated poundings. Mark, who was behind me, pushed me forward ever so slightly to gain access to my virgin ass. I had never tried anal sex before, and in fear I tightened my sphincter in resistance. But Mark had placed copious amounts of lubricant on his cock, and he was going to enter me, whether I wanted him to or not.

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