March Maddyness: Round 01

1. JC / 2. JM / 3. KM / 4. AJ / 5. JB / 6. NG / 7. JR / 8. RA

These were the notes I'd written on the margin of our Tuesday morning staff meeting agenda, and which I then carried back to my office, ready to add the bracket to my whiteboard. The hallway buzzed with talk of the NCAA Tournament, just as it had ever since March Madness hit.

"You sure you don't want into the pool, Maddy? Last chance!" As he often did, my co-worker Andy checked me out in a not-so-subtle way as he talked to me.

"I'm sure, Andy. I don't know much about basketball, and I'm not letting you guys take my money that easily! Actually," I said as I walked into my office, "I think maybe I'll set up a tournament of my own, and see if you guys want in!"

The men laughed, totally unaware of the true meaning of what I'd just said. I smiled to myself, found a ruler in my desk, picked up a whiteboard marker, and drew the lines of my eight-person tournament, assigning initials to each line once the bracket was drawn. Once it was done, I added a title - "March Maddyness" - at the top, and couldn't help but laughing.

The idea had hit me suddenly during our morning meeting. For the past week or so, my co-workers, who were normally capable of conversing about many different topics, could now talk of nothing but college basketball. I hate to reinforce a stereotype, but I am the one female employee in the office, and I'm also the one person not interested in the NCAA Tournament. The guys had tried to get me to participate in the pool, probably assuming they'd easily take my money, but I had turned them down every time they asked.

So at this morning's meeting, while listening to yet more conversations about brackets, and conferences, and rankings, I found my mind wandering. Hard to believe, I know. But where it wandered was the surprising part, even to me. As I watched my co-workers talk, I remembered how each and every one of them had hit on me at least once in the time I'd worked there - which was just over a month.

I'd started with the firm, as the youngest sales rep, in early February. When I came into the office on Valentine's Day, just my second week of work, my desk was covered with boxes of chocolate, flowers, and big heart-shaped cards. At first I thought it was just because I was new, or because I was the only woman in the group, but soon it became quite obvious that the men were actively competing for my attention.

It wasn't anything that made me feel uncomfortable, but let's just say I'd had more offers for dinner or drinks than I could count. I had let each of them down gently, explaining that I was flattered, but thought it would be best if I got a good start at the firm, without mixing business and pleasure. Everyone seemed to understand, and over the past month I'd settled into various levels of flirtatious but harmless banter with each of them.

And, after all, I was used to the attention, so it wasn't anything that really surprised me - especially in joining an office full of men. I'm a 24-year-old 5'3" redhead with big green eyes, a pretty face, and a stunning body - perky C-cup tits and a tight little ass. I'd had several years of experience with men drooling all over me, so I'd developed the skills to let them down easy.

So, back to my wandering mind, and the surprising daydream that arose from my co-workers' blabbering about sports. I started to imagine holding a tournament of my own, with these very men competing against each other. What was the competition, you ask? Well, after a few rounds, I would learn, once and for all, which of these guys was the best in bed.

Crazy, right? But it hit me in our meeting, because the boss - who I would not be including in the tournament, by the way - had reminded the group that this was the week when I would be job-shadowing each of them. I'd been through all of my basic orientation and training with the firm, and now it was time to learn from each of my more experienced colleagues. Starting today, Tuesday, and for the rest of the week, I'd spend my morning with one person, my afternoon with another - so that by Friday evening, I would have shadowed all eight.

And because of the nature of our business - with travel around town and meals out - I should have plenty of easy opportunity to proposition them over lunches, dinners, drinks. I squirmed a bit in my chair, the warmth growing between my legs as I undressed them with my eyes, fantasizing about potential encounters. It had been a while since I'd let myself think such dirty thoughts, especially at work. I feel the need to stress here, in spite of the naughty plan I've just shared with you, that I really do pride myself on my professionalism in the workplace.

I wouldn't tell them about the tournament, but I had a feeling that by the time the second round rolled around, they'd figure out what was up, and hopefully step up and bring their "A" games. As I looked at the bracket I'd drawn, I realized what I was in for over the next few days. The boss' schedule for my job-shadows dictated the daily match-ups, but it was remarkable how well those pairings played into the rankings I would have chosen anyway.

Tuesday would see the 4 vs. 5 match, with the aforementioned Andy, a 30-something who wore his flirtatious banter on his sleeve, up against John, a much more suave and mature 50-something. Wednesday was a no-brainer, with the dreamy Justin at #2, going up against shy, slightly awkward Jeff at #7. Thursday was a little difficult to predict, with two men I knew less well - Kyle and Nick, the always mysterious 3 vs. 6 pairing. And then there was Friday, with the hottest guy in the office, Jacob - my obvious number 1 seed - going up against the number 8 seed, Richard. Wasn't expecting much contest with that one.

Oh my god, this was hot. I would, of course, still do my job, observing, learning from my colleagues as I watched them work. But I'd also be looking for my opportunity with each of them - whether a quickie between meetings or a long, drawn-out fuck session at the firm's hotel suite downtown - to make my pick and move the winner on to the next round. The power I knew I had over each of these men was making me giddy with excitement over the naughty few days I had planned.

I hope you don't mind if I spare you the details of the job-shadowing experiences, and just get right to the sex? After all, who except for me needs to know more about how Andy balances his expense reports, or how Nick uses his powers of persuasion to sell a client more product that he thought he needed. Good, that's settled. So, on to the story of how I spent the rest of my Tuesday.

After spending the rest of the morning in Andy's office, he took me to the downtown restaurant we typically used for client meetings. Taking advantage of the fact that we had been seated in a booth, I made my move, wordlessly. I reached towards him under the table, and put my hand on his thigh, squeezing suggestively. He looked at me, his eyes big with surprise, but he didn't make any move to object.

I slowly slid my hand up to his crotch, finding his cock already hard enough to create a bulge in his slacks by the time I reached it. I began stroking him, slowly, first through his clothes, then gradually unzipping his slacks and pulling him free from his boxers. Even as the waitress visited the table to take our orders, I continued stroking, watching him struggle to remain calm as I toyed with his balls for a moment, then returned to stroking his shaft, which was now jutting straight up, hard and thick.

In the time between placing our order and our food finally arriving, I had him close to the brink of a climax. I leaned towards him, suggestively showing him my cleavage, and asked if he wanted to give me a mouthful of cum. He could only nod in response, my hand now stroking him at a furious pace. I handed him my napkin, instructing him to drop it on the floor when he was ready, so that I could pretend to duck under the table to get it.

After a few moments more, he followed my direction, throwing the napkin down, and I quickly climbed under the table, wrapped my lips around the tip of his shaft, and continued to stroke for a few seconds more until I felt him jerk and shoot his load deep into my throat. As soon as I had swallowed, I climbed back up to my seat, dabbed at the corners of my mouth as if I'd just sampled a great delicacy from the restaurant's menu, and waited to see how Andy would respond during the rest of our time together.

Much to my dismay, in spite of his strong points for stamina, willingness to participate in my naughty scheme right there in the restaurant, and a delicious load of cum, he lost out for his complete lack of initiative to pay me back with any pleasure of my own. We ate our food, the plates were cleared, the bill charged to our account, and we were back to the office, all without so much as a hint of attention to my needs. Hmm, we'd see what his competition brought to the table later that same day.

***

John, who I'd ranked as the number 5 seed below Andy, quickly proved himself to be more of a gentleman in our interactions, a quality which I hoped would carry over to more intimate activities. After a long afternoon of conference calls and face-to-face meetings with clients, we ended up at the same restaurant where I'd enjoyed lunch - and more - with Andy. As we enjoyed a drink, I studied John. He was, I guessed, early 50's, but still extremely handsome. As we chatted, he didn't really feel old enough to be my father, but his age was revealed in some obvious ways - his old-fashioned kind manners, the lines around his eyes when he smiled, and his graying hair.

As I made my flirting more and more obvious, touching his arm, then his thigh, with my hand, he finally surprised me by calling me on it and raising it to another level.

"Should we take this to the hotel suite, Maddy?"

"Um, well, yes, that sounds wonderful!"

"Let's go."

He casually dropped a 50 dollar bill onto the table and led me out, and it was when we walked out onto the street that I realized the hotel where our firm had a suite was just down the block from the restaurant we frequented with clients. Made sense, I guess! He didn't so much as touch me in the lobby, the elevator, or as we opened the door, but as soon as we were inside the room, he pulled me into a tight embrace, kissing me passionately.

He then led me gently over to the bed, encouraged me to lie back with my legs dangling over the edge, and then knelt in front of me, spreading my legs with his strong hands, and gradually pushing up my skirt until he had full access to begin pleasuring me with his hands and mouth. After such a long day of work, and especially after the few drinks we'd enjoyed at the restaurant, I let my tired body relax into the bed as he touched me, licked me, probed me.

This was clearly a man with confidence, a man with experience, a man who had pleasured more than a few women in his day. I began writhing beneath him as his tongue probed my pussy, his thumb simultaneously rubbing back and forth across my clit. Just as I started to let myself go, preparing for my approaching climax, he slowed and pulled back, quickly removed his slacks and boxers, and joined me on the bed.

I moved towards him as if to take his already-hard cock in my hands, but it was clear he wasn't interested in any more foreplay. He gently pushed me back down against the bed, climbed on top of me, and slowly pressed his long, hard cock deep inside my dripping wet pussy. Moving very slowly at first, he gradually picked up the pace, bringing his lips to mine for another strong kiss as he fucked me.

After a few more minutes in this position, he rolled us over, so that I was on top, and I sat up to ride him. He unbuttoned my blouse and grabbed my tits, squeezing them gently as I bounced up and down on him, and it wasn't long before I climaxed, covering his cock with my juices. I rode him for a few moments longer after coming down from my climax, before he pushed me up, climbing out from under me to stand up on the bed. I knelt beneath him as he stroked himself furiously for a few moments more, then shot his load into my waiting, eager mouth.

Hmm, not as tasty as Andy, but overall, he obviously won the round. Guess I was off on my initial rankings!

***

When I walked into the office on Wednesday morning, I was confident that the tournament was still a mystery to the group. John probably had the class not to say anything to anyone, and while Andy didn't, he was likely just patting himself on the back for the conquest, and had no idea everyone else in the office would also be getting lucky with me that week! I added John's initials to the next round on the bracket on my whiteboard, and then went off to find Justin.

My number 2 seed was one of the more attractive men in the office, a tall, athletic 30-something with short-cropped brown hair and deep brown eyes. The only obvious strike against him since we'd met was that, as the one guy in the office who had actually played basketball in college, he was the most annoying of the whole March Madness bunch, constantly talking with authority even though his team never got anywhere near an invite to any tournament.

Whether Andy had said something to him about our encounter yesterday, or whether he was just responding to my own flirting, Justin was quick to reciprocate my advances, making the morning of work and meetings powerfully charged with sexual energy. As he showed me some spreadsheets on his computer, I leaned over his desk, blatantly giving him a full-on view of my tits. As we talked with a client over the phone, I kicked off my heels and ran my foot up his leg, briefly teasing him with quick touches to his crotch, where I felt his cock already hardening.

By the time we made it to the car, where our driver, Bob, was waiting to take us to a meeting across town, we could hardly keep our hands off each other. As Bob started the car and began driving, Justin pushed the button to raise the opaque glass between the front and back seats. As soon as the glass blocked Bob's view, Justin's hands were on my body, with one hand squeezing my right breast firmly, the other hand quickly moving down towards the hem of my skirt.

I reciprocated by finding his firm bulge, and began stroking it as he forced my skirt up and began rubbing my clit and pussy lips through my panties. I couldn't help but begin panting and sighing under his touch, and he responded by pulling his hand quickly away from my crotch and bringing it to his face, putting a finger to his lips to remind me that even though Bob couldn't see us, he could still hear us.

This need to stifle my expressions of pleasure only heightened the excitement for me, as Justin returned his hand to my crotch, this time pushing my panties to the side and touching my skin directly. I arched my back in immediate response as one of his fingers easily slipped into my wet pussy, and focused my hands on freeing his cock from his slacks. After fumbling for a few moments with his belt, buttons, hooks and zippers, I finally was rewarded with his big, hard cock in my hands. He was longer and thicker than either of the men I was with the day prior, and I couldn't wait to feel him inside of me.

After focusing all of my attention on his cock for several moments, I looked up into his eyes, trying to silently communicate my desire for him to fuck me, right there in the car. Whether he understood, or just had the same desire, he immediately responded, plunging into me with one hard stroke. Perhaps knowing that I'd have trouble keeping quiet, he brought the hand that had been playing with my tits up to my mouth, gently covering it while he began fucking me, hard, pressing me back into the hard leather car seat.

As he pounded me relentlessly, the movements of the car through traffic continually changed our position, shifting us around in the seat as we turned left, then right, sped up, and slowed down. The unexpected motions, together with the pressing need to remain quiet, were enough to bring me to a climax, and the pulsing pleasure in my pussy was especially powerful given that I could still remember the sensations of my encounter the evening before.

As I writhed beneath him, covering his cock with my juices, Justin slowed, then pulled me back with him as he sat back down on the seat, so that I was sitting on his lap, his cock still buried inside, and could begin riding him. It took a few moments before I could handle his full length again, but before long I was riding him with abandon, the movements of the car once again creating amazing sensations.

After just a few moments more, Justin pushed me up, and I climbed down to the floor of the car, kneeling between his legs. I eagerly took his cock and balls into my hands and mouth, stroking furiously until I was rewarded with a huge load of delicious cum. It was all I could do to swallow every drop, as some of his cum threatened to spill out of the corners of my mouth. We also had to quickly straighten ourselves up, furiously buttoning, zipping, straightening, as Bob drew the car up to the curb at our destination.

***

I was giddy for the rest of the afternoon after my sensational fuck-session in the car with Justin that morning. Thankfully, that attitude, and the lingering sensations between my legs, were enough to carry me through a very disappointing showing from my 7 seed, Jeff. He was a shy, somewhat awkward guy, so much so that I struggled to figure out how he ended up in sales. Jeff and I had a productive and professional afternoon together, but let's just say he was incredibly dense when it came to responding to the advances of a hot young woman.

In spite of all of my efforts - batting of eyelashes, putting cleavage on display, touching him on the arm, the thigh, etc. - all I got out of Jeff was an awkward embrace and peck on the cheek at the end of our time together. I'm not the type to take it personally, but it did make me wonder what was up - after the other guys had all taken easy advantage of the invitation I'd given them. Was he involved with someone and didn't want to cheat? Was he worried about mixing business and pleasure? Was he really that shy and awkward? Oh well, time to move on, giving Justin the easy win in this bracket.

***

By the time Thursday rolled around, I was in the groove. Any concern I might have had about my slutty behavior at work had long since been replaced by my pleasure at the whole scenario - the sex itself, the fun game of putting my male co-workers through the competition, the anticipation of what might happen after they all realized what I was up to - I was thoroughly enjoying myself.

Thursday turned out to be the battle of two quickies. There were no out-of-office opportunities in the schedule with either Kyle or Nick, my 3 vs. 6 match-up, so I was forced to find ways to test their skills within the confines of our office suite. It was an interesting pairing - nerdy but attractive 30-something Kyle going up against the oldest of the group, Nick. Nick was at least 60, but from what I could tell, still quite active, fit, and frankly, the most likely of the group to insert a risque joke or story into a meeting - so, in spite of his age, I was intrigued to see what he'd bring to the big dance.

My morning encounter with Kyle turned out to be in the copy room. Our bodies pressed against the door as a convenient way to keep others out, his erection quickly growing against me, we kissed hard as he moved his hands roughly over my body, unbuttoning my blouse and forcing my skirt up to my waist. I gasped as I realized the vulnerability of my position - even though we'd likely hear someone coming towards the door in time, Kyle had me half naked as he squeezed a round of foreplay into just a few hurried moments.