The Bet

My name is Callie, and I just lost a huge bet. I only made the bet because I was so sure I was going to win. A coworker I work with is an arrogant prick, and I was dying to put him in his place. How could I lose a sure thing? Well I will tell you.

I work for a large advertising company. I work with a large group of horny old men. I tend to dress to impress, and often get leered at. My tastes in clothes are professional, but can on occasion be fairly revealing. Often I wear medium length skirts, and semi revealing blouses. I occasionally go without panties and love to bend over at the waist periodically to get a rise out of my unsuspecting coworkers. I like be a bit fun and flirty, what can I say. However I have this one coworker that is a bigger flirt than me. He likes to take things a bit too far, and can get a bit rowdy.

I have been giving it a lot of thought, and I decided a bet would be just the ticket. It would stroke his ego and he wouldn't be able to refuse. I confronted him alone one day and pitched my idea. He was immediately on board, like I knew he would be. The bet was who could land the biggest deal of the week. I already had a client lined up and it was going to be a big one. The stakes were that the loser would be the winners slave for a full day. The winner could make the slave do anything they could think of. If I knew the outcome was going to be how it ended up, I might have done things differently.

I had so many visions of him on his hands and knees, cleaning my house. Waiting on me hand and foot, I may have also invited a few of my lady friends over and really embarrass him. I knew I had this bet in the bag. So my imagination ran wild. So you can imagine my surprise when I strolled into work Friday morning and hear my world come crashing down around me. I knew right away by the smug look on his face that the news wasn't good. Our boss confirmed the bad news a few minutes later. To say I was crushed was an understatement. How the hell did I lose? I just landed the company the biggest deal it has seen in years.

Turns out Eddie, had a big client of his own. I couldn't believe my bad luck. All said and done I lost by a measly two freaking dollars. Can you believe that shit? Two damn dollars! I spent the rest of my day hiding out in my office. I was in total disbelief, I thought about running away, but decided in the end that a bet was a bet and I would follow it through to the end. Besides, what's the worst that could happen? My fears multiplied when Eddie entered my office about closing time, big shit eating grin on his face. He closed my door and sat down in the visitor chair across from my desk. He just sat there for a bit with that big nasty grin. I couldn't even look at him, my plans were shot. I was devastated and he knew it.

Being in the bad mood I was in, I looked over at him finally and told him to just spit out what he had to say. He knew it was getting to me just sitting there and not speaking. He got up out of the chair and walked over to my desk. He took a blank sheet of paper, a pen and wrote down an address. "Be there tonight by 8pm so we can go over the details of your surrender." He said as he turned, and walked out of my office.

I feigned having a headache and told the boss I was going home early. He just grinned at me and said he would see me later. I didn't know what that was all about but wasn't going to stick around any longer and find out. I would just see him Monday when I returned back to work. I made it to my vehicle and just sat inside contemplating my doom. I was totally numb, and couldn't get my mind on the task of driving home. My husband was away on a business trip so the house would be empty. I was broken from the trance I was in from my phone ringing. I answered it not even looking to see the caller id to see who it was that was calling. Turned out it was a girlfriend of mine, wanting to know if I was free tonight to get some food. I declined her offer telling her I had other plans. She sensed I was distracted by something and asked me what was going on. I told her that I had done something stupid and was regretting it. She wanted to know more but I cut her off saying I would tell her all about it later.

I managed to get myself safely home without incident, my mind was all over this stupid bet I had lost. I still couldn't believe it had happened. I pulled into my driveway and thought to myself that I really didn't want to be home at that moment. So I pulled back out and just decided to drive around till I had to be at Eddie's house. The more I drove around the better I began to feel. The weather was nice and I had the windows rolled down letting the fresh air blow through my hair.

At 8pm sharp I pulled up to the address Eddie had given me. I sat parked for a few dreading going to the door. Eddie had seen me pull up and walked out his front door. He waved me in and turned and walked back inside leaving his door open. I plucked up all the courage I could muster and exited my vehicle with my head held low I proceeded to go inside and get this over with. I didn't see Eddie as I entered, so I called out for him. He came out from a back room a few seconds later holding a large box in his hands.

"This is for you" he said to me while holding out the box. "Inside the box you will find an outfit that you will be wearing tomorrow. You will only wear what's in the box, nothing more, and nothing less. Do you understand?" I didn't know what was in the box, but I nodded my head in agreement anyways. He invited me to sit and take a look, but I didn't want to be there any longer than I had to and declined his offer. Made the excuse I had to get home to my husband. He walked me to the door, and as I opened the door to let myself out he smacked me right on the ass. I was still in a trance and was half way home before it dawned on me what he had done.

As I walked through the door of my house, I quickly undressed and jumped into bed. As I lay there in bed I looked over at the box just sitting at the chest I had at the foot of my bed. I wanted to ignore it and hope it was just a really bad dream. The longer I looked the more I knew it was all for real. Resigned to my fate I got up and opened the box. My heart sank, before my very eyes were a naughty French maid's outfit. Although the more I thought about naughty wasn't quite the right word for what I was seeing.

I took out the items and placed them on my bed. I was speechless. This thing was beyond revealing. My lady parts were going to be on total display. It looked really sexy, and I knew I was going to look spectacular in it. Along with the dress if you could call it that, was a pair of thigh high stockings, a little mop hat, a pair of four inch strappy high heels, and a little duster. Apparently he had thought of everything and this was an ongoing fantasy of his. I checked the sizes, hoping to find that it was too small for me. Turned out Eddie knew his sizes, every piece was just the right size.

I decided I needed to try it on. I just had to see myself in it. Once I got it all figured out and in place, I looked over at myself in the mirror and my jaw dropped. I looked amazing, and I devised a plan while looking at myself. I decided to make the best of it and that I would show Eddie what he got himself into. I was going to tease the hell out of him. I was going to lead the show and make him wish he hadn't taken things this far.

The thought of teasing poor little Eddie got to me and I could feel myself become wet. I was getting extremely turned on and had to have some solo fun. So I got out a few toys and proceeded to enjoy some alone time. It took no time at all to get my toys hammering my tight little holes. I was so turned on I needed an immediate release. It didn't take long to bring myself to several orgasms. I was leaking juices all over my sheets. After what felt like hours, I became too tired to continue. So I removed the outfit and jumped into bed ready for a good night's sleep. I was out the second my head hit my pillow.

I awoke the next morning feeling quite refreshed, but a bit nervous. I looked at the time and realized I had a few hours before I had to be at Eddie's, and I was going to spend that time making myself silky smooth. I shaved my legs, trimmed up my precious kitty, made sure other areas were hair free and started to get dressed. I figured I would just throw some clothes on and get to Eddie's a little early and change into the costume there. I really didn't want anyone seeing me leaving the house dressed in that naughty outfit. It would have raised too many questions and possibly gotten back to my husband.

I got to Eddie's about ten minutes early, he heard my car pull up outside. And greeted me at the door with that huge arrogant smile he always had. He noticed me carrying the box, and reminded me again that I wasn't to add anything to it, or take anything away. I just smiled and pushed my way through the doorway. I didn't want to be standing outside any longer than I had to. I walked through to his living room and noticed a poker table set up in the middle of the room. My worst fears hit me like a runaway freight train. He was planning on having an audience. I could see five chairs at the table. I was in a lot of trouble. I also noticed though that I was leaking juices down my leg, my kitty was betraying me. She was begging for this, while I was dreading it.

Eddie showed me to his bedroom and told me I could get changed in there. I sat on his king sized bed, hoping this was all just a bad nightmare I was having. I was awoken from my thoughts by the sound of the doorbell. I could hear two male voices, but couldn't hear what they were saying. I got up the courage I needed, and proceeded to get changed. I looked myself over in the mirror. I looked amazing. I couldn't wait to get my tease on. These guys were going to regret messing with me.

I walked out into the living room, and as I turned the corner going into the living area I could see the guys had arrived and had their cell phones out quickly snapping pictures before I knew what was going on. It was then I realized I was in trouble. With those pictures they would be able to control and blackmail me to do their bidding. My plans came crashing down to earth in a huge fiery blaze. To my greater horror, I found one of the guests was my very own boss. Eddie looked over at our boss and said. "I told you if you helped me doctor the clients payments you wouldn't regret it." That little worm he bribed our boss so he could win the bet. I was pissed, but in no position to do anything about it.

I would work on my revenge another day, right now I just had to get through this nightmare. Eddie then made matters worse by telling everyone I would be the day's entertainment that I was here to do anything and everything anyone asked. I would follow through happily or find those pictures they took distributed around work and possibly family members. I lowered my head in defeat, so much for an easy night. Eddie walked up to me and whispered in my ear, telling me not to worry too much, he was the only one going to get to fuck me tonight, I was however going to be doing other things to his grateful guests. Eddie looked at his guests and said "Gentlemen this is your luck day. Callie here will be today's entertainment. "The rules are as follows. One, she is here to serve as we please. Two, you may touch her in any which way you please. Three, the winner of each hand will get to choose something naughty for her to do. Final and most important is that no one will be fucking her. She is mine and I won't be sharing her tonight. I have been waiting for this day since I first started and want our first time to be just the two of us." Several of the guys grumbled in their sadness, having their hopes crushed.

I was actually surprised that I was getting very horny from what he had said. With the neglect I was getting at home, I found I wanted this more than I was dreading it. I was going to finally have the fun I so desired. I could feel my juices running down my leg. I knew the others could see it as well. Eddie took his seat among his friends and started to deal out the cards. He looked over at me and said I would find the snacks in the kitchen, and the beer in the fridge. I hesitated a moment, my mouth still hanging open. Not believing I was in the predicament in the first place. I then walked to the kitchen and found indeed the snacks all out on the counter. I grabbed a bowl of chips and a few dips; I then got a few beers from the fridge. I made my way back out to the living room.

I couldn't carry enough beers for everyone, and planned to make another trip to get the rest when I was informed that there had been a winner while I was gone. Eddie pointed over to a guy he called Mike. Mike was medium sized, and seemed a bit embarrassed. Eddie asked him what he wanted from our lady of the day. He stumbled through a few words before he managed to say he wanted me to come over and bend over in front of him. I quickly did as I was told.

I stood next to Mike, my back to him, and slowly bent at the waist. I could feel the skirt of my costume rise up as I bent over. I knew the view he was getting was sure to be a good one. I wasn't allowed to wear panties, so I knew I was on full display. I didn't know how long I was supposed to hold that pose so I stayed in the position. I could hear the guys mumble words of their appreciation. I then heard the cards being shuffled and took that as my cue to get back to work serving.

I went back into the kitchen and got the remaining beers I hadn't been able to get the first time. I came back out and passed them out. I stood next to the table watching them all bet their chips. I was sure they did not want to fold any hands in hopes of being the next winner. Eddie had bluffed his way through buying the pot with a huge bet. I knew he was bluffing, but no one wanted to lose all their chips and be out of the game so soon, so they let him take the win.

He raised his hand and gave me the come here finger. I walked right over and he motioned for me to sit on his lap. His hand immediately went between my legs. He began to finger me in front of his guests. It felt amazing. I was totally wet so his finger slid right in, soon he had two fingers inside me. I couldn't help but moan. He was doing a fantastic job. Then out of nowhere he stopped and pulled his fingers out, raised them to my mouth and told me to lick them clean. I was so close to an orgasm, I felt frustrated when he stopped. He pushed me from his lap and proceeded to shuffle and deal the cards once again. The next hand got rather heated, two of the guys thought they had what it took to win and loaded the pot with every chip they had. I later found out the two guys were Ben and Jon. Ben called Jon and we all watched in awe as Jon flipped his cards to reveal a small straight. Huge grin on his face, he went to reach for the pot and was dumbfounded when Ben flipped his cards to reveal a four of a kind. He had four fives, and knew he was the true winner. Jon got pissed and stormed out the front door in a barrage of curse words. I was happy though the group of five was now a group of four. If they kept this up it would turn out to be a fast night.

Ben, being the winner, called me over and slid away from the table. He remained in his chair and unzipped his pants. I quickly looked over at Eddie to save me. He knew what I feared, and told Ben he made it clear there would be no fucking. Ben just looked over and smiled. "Yes, I know you said no fucking, but last I checked a blow job wasn't fucking." Eddie looked at me and said Ben had a point. I didn't say anything about oral. Defeated, I walked over to Ben and got to my knees. Ben had pulled out his tool and I was impressed, it was fairly long and thick. Larger than what I was used to getting at home. I pride myself on my oral skills, and quickly got to work. I took his member into my mouth and proceeded to give him the ride of his life.

I was done being shy, between being paraded around in next to nothing and the fingering Eddie gave me I was beyond horny. I took Ben in as far as his body would allow. I gave him long slow strokes. And I would stick my tongue out to lick his balls every time I got his tool all the way in my salivating mouth. I felt his hand grab the back of my head, I knew how good I was and I wasn't holding anything back. I began to quicken the pace. I wanted to make him blow his load deep in my mouth. I was rewarded a few seconds later when I felt the first rope hit the back of my throat. I lowered my mouth as far as I could down his shaft and sucked for all I was worth. He released several more ropes before falling from my mouth totally limp and spent, with a popping noise. He looked on the verge of passing out. He obviously had never had a blow job like I just gave him in his life.

He lay back in his seat panting, trying to take in what just happened. The other three guys began to clap their hands, whooping and hollering for what they just witnessed. I stood back up and asked if anyone needed anything. A few asked for more beers and more chips. I sauntered away swinging my hips, shaking my ass. Proud of what I had just done. I came back out a few minutes later with the beer and chips. Ben was still lost in la la land, and had to sit out the next hand. It was Eddie, Mike, Ben and my boss still fighting it out for who got my next pleasures. I was actually dreading having to do anything with my boss. Everyone else was just another guy, but my boss, I had to see every day. I really hopped he would be the next one out. The next hand ended up being another duel, this time between Mike and my boss. I crossed my fingers and prayed, but my prayers went unanswered and my boss took the win. His win was so big it left Mike with one chip. Which didn't help him out any so he tossed the chip to me, got up leaned in a planted a small peck on my cheek, thanked me for a wonderful time and walked out the door.

To say my boss was happy was an understatement; he sat there ogling me trying to decide what his prize would be. He decided and called me over after scooting back from the table just as Ben had done. I thought he was going to want the same so I relented and started to drop to my knees. He stopped me however and said he had always wanted to see my tits. That we had worked together for five long years and every day they were all he could think of, and nothing else. So he grabbed my wrist and pulled me into his lap. I sat facing him and he spent no time reaching for my top and revealing my beautiful breasts. He took a good long look before leaning in and devouring my nipples. He was like a kid in a candy store. He quickly moved his mouth back and forth between my two exposed breasts. He would softly suckle a nipple for a few short seconds before moving over to the other. He had my nipples hard as a rock in no time. He moved from suckling to lightly nibbling.

His hands then moved up and he began to grope. He would tweak the nipple that he didn't have in his mouth and change when he moved his head over to the other. He spent several minutes doing this getting rougher as time went on. He was soon biting my nipples to the point that I felt little jolts of pain shoot through me. I began to moan with each bite, it hurt but also felt good. I found myself slowly grinding on his lap. I could feel his hard on lumped in his pants, it felt good rubbing against my swollen clit. If he didn't stop soon I would be having my first orgasm of the night. Just as I was about to cum all over his pants, Eddie called for time; once again I was saddened to be so close only to lose it again. I was gagging for an orgasm and didn't see one in sight. My boss reluctantly let go, he pulled the top of my outfit back up and allowed me to vacate his lap. He seemed as depressed as I was. I did notice though that all the grinding I had been doing had left quite the wet spot on his pants. I giggled as I walked away. My boss straightened out his erect bulge and scooted himself back to the table.