March Maddyness: Round 01

Freeing my hands from his embrace, I reached down and unzipped his slacks, freeing his cock, which although very hard and erect, was a little disappointing in its length, only about 5 inches. He reached down, took his cock into his own hands, rubbed it against my pussy lips to wet the tip, and then plunged into me, quickly kissing me to stifle my gasp. Once inside of me, he took my hands in his and held them over my head, pressing them against the door, as he forced my body upward with his fast thrusts into me.

On one of these thrusts, I took a chance which made my position even more vulnerable, letting my feet leave the floor, my heels falling off and dropping to the floor in the process, and wrapped my legs around his waist. The sensation was incredible as I felt completely weightless, supported only by his hands wrapped around mine, and the constant quick thrusts of his cock. I came hard and fast, and Kyle wasn't far behind, helping me back down to the floor beneath him just in time to kneel, taste my own juices on his cock, and then swallow his load. The entire encounter probably lasted no more than 5 minutes, and we were back to work.

***

The encounter with Nick was even shorter, and although it had its moments of excitement, I'm afraid he took himself out of the competition by cumming too soon and not bringing me to climax before we had to escape the supply closet, the only room we'd managed to find for our little tryst. I'll spare him the embarrassment of sharing any more details of his quick exit from the contest, and instead credit him with being the first to figure out what I was up to.

"So, Maddy, you got sick of all the 'March Madness' talk and decided to have a little fun of your own, at our expense?"

"Ah, so you figured it out, huh?"

"Well, a few of the guys are talking, and it didn't take long to understand what you were up to once I saw the whiteboard in your office."

"Ah. Well, so I guess it's out in the open. I do have to argue with the idea that I'm having fun at your expense, though. I'm pretty sure we're all getting something out of this little competition."

He laughed. "Good point, Maddy, I doubt any of the guys will mind being treated as sex objects by a hottie such as yourself!"

***

By the time Friday rolled around, I have to admit, I was tired. There was actually work to be done as part of my job-shadowing, and I was making every effort to keep up with it, along with, of course, my extra-curricular activities. My morning was to be spent with Richard, and then - the time I was most looking forward to - the afternoon and evening with Jacob, my top-ranked guy.

From the very beginning of my time with Richard, he reinforced the low ranking I had given him, and not in the way you might think. He was very attractive physically - mid-20's, athletic, 6'2" with wavy blonde hair and big blue eyes, and the kind of features that always appealed to me: strong hands, a chiseled jaw. But as I learned that morning, he was the classic example of a person who might be beautiful on the outside, but certainly wasn't on the inside.

For the entire morning, whether we were looking over spreadsheets or talking to a client on the phone, he managed to fit nasty comments about all our co-workers into the conversation. Yes, that's right - even on the phone with a client. While all of my other job-shadow experiences had taught me valuable lessons for my future professional development, the only thing this guy was teaching me was how NOT to act. He was proving himself to be bitter, angry, and unprofessional.

Of course, I told myself, I still had to suck it up and proposition him, if I was truly going to make an informed decision about who made it through to the next round of March Maddyness. This meant, of course, that it was the first time that week that I truly felt like the dirty little office slut. All of the other guys, even awkward Jeff, had held some genuine appeal as men, making my tournament a fun journey. But this one - well, I would definitely be the one taking one for the team this time around.

And so it was hardly a surprise that when Richard took me up on my proposition, he was only interested in getting a little something for himself, and in a way that was the least fun for me: on my knees on the hard, dirty supply room floor as he roughly banged away at my mouth, without even the decency to reach down and pinch a nipple, or pull my hair out of my face. It really was all about him, whether it was in an interaction with a colleague, or when presented with the opportunity for sex with a hot young woman. What a loser. And so, he became the second guy to pull himself out of the tournament, regardless of what happened with his opponent!

***

I was so frustrated by the time I met up with Jacob to start our afternoon of job-shadowing that I must have been wearing my emotions on my sleeve, as I learned when he greeted me with concern.

"Are you OK, Maddy? You look upset."

"Oh, yeah, Jacob, I'm fine. Just didn't have the greatest morning, that's all. But I'm excited to work with you this afternoon!"

"Sorry to hear that, but yes, I'm excited to work with you as well! I'm afraid we've got some boring paperwork to take care of for much of the afternoon, but then I was thinking of taking you out for a drink to celebrate the end of the week. Sounds like it's been a busy one for you!"

I instantly blushed, realizing from the twinkle in his eye that he'd obviously heard the rumors of what I'd been up to that week. I don't know if he understood about the tournament, or whether he just thought I'd spontaneously decided to be the office slut, but either way, he already knew I was a sure thing.

"Um, yeah, busy."

I smiled awkwardly, realizing that it was the first time all week that I wasn't the one in the driver's seat. Jacob knew what I was up to, and he was clearly planning to tease me about it all afternoon, and then take advantage of it that evening. I couldn't wait.

I was actually able to relax a bit that afternoon, and focus on work, knowing that I wouldn't have to spend the hours engaged in blatant flirting to get my point across. That said, we still had our moments - Jacob checking out my tits as I leaned over his desk, my hand grazing his as we looked over paperwork together. And when we left the office together, he didn't bother with the pretense of taking me to the restaurant where our firm had an account. We went directly to the bar at the hotel.

I pulled up close to him in a booth, resting my body against his as the waitress delivered our drinks and happy-hour appetizers. Teasing me once again, as he had been doing all afternoon, he said, "Excuse me, Maddy, have you ever heard of personal space? A little professionalism, please!"

I pulled away, returning the devilish smile he was giving me, and settled for letting my skirt ride up dangerously high on my leg. Time seemed to crawl by as every inch of my skin burned with desire, and yet Jacob remained completely calm and in control, slowly finishing his drink before finally suggesting that we move things upstairs.

My fatigue from the week, combined with the fact that I'd nervously had one more drink than I normally would, left me a bit light-headed, and I found myself eager to let Jacob take the lead. It was also a role that he seemed particularly comfortable with. I studied him as we walked through the lobby, rode the elevator, and then walked down the hall to the door of the suite.

Jacob was in his mid-40's, and combined a youthful handsomeness with a mature confidence that was incredibly appealing. About 6'1" with an athletic build, his dark blonde hair was cut short, and his deep blue eyes seemed to express volumes every time he looked into my own. I'd always found him attractive, even in the days before I'd dreamed up this little tournament, and could hardly believe that we were now about to be alone in a hotel room.

"Strip for me," he said softly and calmly as soon as we walked into the room. He tossed his jacket down over the arm of a chair, kicked off his shoes, loosened his tie, and removed his belt, then sat down on the bed to watch me. I smiled shyly, then dug down to find some confidence, and began obeying his command.

I slowly unbuttoned my blouse, my eyes never leaving his as I moved ever closer to him, one step at a time. Once the buttons were free, I let the blouse slide from my shoulders and cascade to the floor. I reached up to my hair and freed it from its work up-do, tossing the hair clip to the floor as my long red hair tumbled down over my shoulders.

I moved a few steps closer to the bed, and then stopped to unzip my short, fitted suit skirt and let it tumble to the floor, stepping out of it once it did. I was now left standing in my matching red bra and panties, and my black heels. I kicked the shoes off, then moved to begin taking off my bra, but Jacob nodded his head back and forth, stopping me in my tracks.

He then motioned with his finger for me to join him on the bed, so I took the last few steps, then sat down next to him. He reached around and unhooked my bra himself, removing it gently and tossing it aside, and then pushed me down so that I was lying on my back next to him, while he began rubbing my clit through my panties, gently at first, then more vigorously. With his free hand, he began toying with my nipples, pinching hard, then just barely grazing, constantly changing up his touch so I wasn't sure what to expect.

I grabbed a pillow and pulled it under my head so that I could watch as he continued to move his hands over my body. He now shifted my panties to the side so that he had direct access to my skin, and continued his furious, relentless rubbing, occasionally dipping his fingers down into my pussy to wet them, then bringing them back to my clit. He brought his mouth to my breasts now as well, so that while one nipple was being tweaked by his strong fingers, the other would be in his mouth, the occasional nibble alternating with wonderful strokes of his tongue.

I moaned in protest as he pulled his mouth away, sitting up once again, but soon my moans were coming from pleasure, as he began furiously finger-fucking me, bringing both hands down now, so that he could insert three or even four fingers of one hand deep inside of me as the other hand played with my clit. I grabbed my own breasts now, longing for the touch he had applied to my nipples, but not quite able to duplicate it myself.

"That's it, Maddy, pinch those nipples, harder!"

I followed his direction, pinching myself harder than I thought possible, and was amazed at the sensation. As he continued to pound me with his fingers, more furiously than anyone ever had, I pinched my nipples as hard as I could, fascinated by the connection of sensation between these two pleasure points on my body.

"Let it happen, Maddy, you can't stop it. Cum for me, baby!"

His words were enough to push me over the edge, and I cried out as the climax hit me, my hands falling away from my breasts but his hands still working me furiously. From the combination of his intensity and all of my encounters that week, I was left raw and tingling after I came down from the peak of my orgasm, and hoped that he might give my pussy some rest while I repaid the favor.

He climbed off the bed for a moment, undressing and tossing his clothes to the floor, and then rejoined me on the bed, where I eagerly positioned myself between his legs to give his cock some attention. He was already hard and erect, although he grew even bigger under my touch, and I was thoroughly impressed with his perfect size and shape.

I spent several minutes giving his cock my thorough attention - licking his balls, stroking his shaft, then deep-throating him as he scooped my hair into a ponytail and used it to control my pace. I could sense that he was in complete control, and although I'm sure I could have made him cum purely with my mouth, he was holding back, more interested in reaching his climax after fucking my tight little pussy. Just as these thoughts were still forming in my mind, he let go of my hair and gently pushed me up off of his cock.

He turned me over so that I was face-down on the bed, taking the pillow I had previously put under my head, and positioning it under my stomach, so that my ass was up in the air, then forced my legs apart slightly, leaving my pussy completely exposed for the taking. Climbing on top of me so that his body completely covered mine, he slowly pressed into me, taking a few moments for every inch of his at least 7-inch cock, until I sighed with pleasure when he finally bottomed out, filling me completely.

Jacob then began moving slowly in and out, complete strokes each time, so that his tip popped out of my wet pussy, no doubt glistening with my juices, and then plunged all the way inside again. I began begging him to fuck me harder, but he didn't oblige, maintaining his slow, deliberate, deliriously pleasurable motions.

"Oh, my god, Jacob, please, please, fuck me faster!"

"A little patience, Maddy, please. Give me this for a few moments more, then I'll let you ride me until we both cum."

I liked that idea enough to stop begging, and managed to hold on through Jacob's enjoyment of pressing into me from behind at his excruciatingly slow tempo. After what seemed like another five minutes at least, I felt him pulling up from behind me and pulling us both into the sensational new position he had described.

When he was resting on his back, his head against the pillows at the head of the bed, and his cock jutting straight up, covered in my juices, I eagerly climbed on top of him, facing him, and lowered myself - slowly, believe it or not - down. Once he was completely buried inside, I then began riding him faster and faster, eagerly taking control of the pace, while he took advantage of having his hands free to once again torture my nipples.

Although they'd never felt such an intense combination of pleasure and pain, my nipples once again responded immediately and powerfully under this new touch, and it wasn't long before I was riding him with complete abandon, pushing us both ever closer to an inevitable climax. I cried out when my orgasm hit, fast and hard, and could sense that he still had more distance to go, even as I relaxed.

He shifted our position once again, pushing me up and then onto all fours, as he climbed on top behind me, slamming into me hard and fast for a few moments more. I reached between my legs and fondled his balls as best as I could with each stroke, which he seemed to greatly appreciate, judging by the intensity of his moans of pleasure.

Just when I thought my raw, tired pussy couldn't take any more, he pulled out, and I felt the warmth on my skin as he covered my back with cum.

"Well, Maddy," he said after we'd both recovered and gotten ourselves cleaned up, "I'm looking forward to the next round!"

"Me too, Jacob, me too!"