Madelyn: The First Time?

PROLOGUE

A few weeks had passed, since I had witnessed my housemate Madelyn masturbating behind her partially closed bedroom door. Having just been dumped that day by my girlfriend, I had come home unexpectedly, while Madelyn was in the act, and had watched her, completely undetected. The scene played in my mind frequently, and I made the most of those memories frequently.

The thought of Madelyn's large breasts wobbling and bouncing as she pinched and twisted her nipples; the grind of her hips as she rode her buzzing vibe in her ass; the sound of her voice moaning and groaning her pleasure in the wanton act just lit me up. I could barely interact with her in our house, without thinking about her touching and playing with herself. Having witnessed her pleasure, it was only natural to begin to fantasize about her in other sex acts. Especially with me.

Madelyn-The First Seduction Attempt

Madelyn was a bit short, standing just under five feet tall. She was a bit heavier, with a set of full hips and bust, she was soft and shapely. Twinkly blue eyes, light freckles across her nose and cheeks, framed by strawberry blonde hair, and a nice smile finished her appearance as cute and bubbly. She could hold her liquor well, always seeming to be one of the last standing at the end of a night of partying.

One evening while I was at the pub, playing pinball amongst friends, she popped in for a cocktail herself. Spying me in the crowd, she gathered up her cocktail and purse, crossed the room, and settled herself into my booth. After introductions were made amongst the folks that didn't know her, we settled on some teams for a dart tournament. Most of the men were better skilled than the ladies, so naturally, we paired up into couples. I of course ended up paired with Madelyn. Madelyn was no novice to the game of darts, and quickly proved herself to be equal amongst us men, giving us a huge advantage over the rest of the couples in the tournament.

As the liquor flowed, the decorum between all of us got bawdy, with innuendo and suggestion ruling our comments about each other's play. Madelyn took to spanking my ass in passing as I left the table to shoot my rounds. A few of these smacks, coupled with my heavy consumption of ale, led me to think of a retaliatory measure, so I took to spanking hers when she left the table to shoot her own round. After a few rounds of this, she began to make a show of enticing my hand; jutting her ass out for me to smack as she left the table, while smirking over her shoulder at me. This, coupled with the innuendo, and then the recollection of those hips grinding down on her vibrator had me hard as a post, and a bit uncomfortable.

This state began to take its toll on my concentration, and my dart game began to falter. I was distracted in my mind, imagining myself pounding my dick into her from behind, while she smirked over her shoulder, moaning and reaching in between us to finger her pussy. With my concentration totally shot, I was unable to play darts well, and we lost our first match of the night. Madelyn laughed it off, thinking the ale was taking effect of my game. I was drunk alright, but with fantasy and desire for my house mate.

After a bit of a rest, and a smoke break, we resumed our tournament. Coming out of the loser's bracket, we had to beat the leader of the winner's bracket twice, to claim the tournament championship. We were playing one of the best players in the pub, and only my best game would compete with the likes of him. We won the first of the brace, with a narrow edge brought on by Madelyn playing exceptionally well. The pub was nearing closing time, so the ale was gone and done. We rushed the last game, and ended up in a close match. Madelyn leaned over just before my turn, and said "Reggie, I will give you a blow job if you win this right here." I laughed, thinking I heard that in my fantasy riddled mind. She giggled, leaned in close again, and repeated "I will give you a blow job if you win this right here. No kidding."

Looking at the scoreboard, I needed a hat-trick to go out, and win. I hadn't hit one in over an hour at this point, but knowing I was capable, I felt my dick begin to get hard. As I got up to toe the line, she smacked my ass in passing. I whirled around to make a saucy quip, but she was carefully biting down on her luscious lower lip, and I was thoroughly transfixed. Her blue eyes twinkled and she began to grin. I was so turned on. I wanted nothing more than to feel her mouth on me, her hands working my shaft while her tongue massaged and slathered the head of my dick. I wanted to come in her mouth while staring into those blue eyes. I wanted to feel her moan on my dick as more come jetted down her throat. I had to win this damn tournament, right the fuck now.

I carefully toed the line. Sizing up my aim, I didn't like my position, so I re-toed the line, and sized up again. A practice wave to the board. Another. Letting it loose on the third wave, the dart sailed dead center into the bulls-eye. Without moving anything other than my throwing arm, I grabbed the second dart. A practice wave to the board. Another. Letting it loose again, on the third wave, the second dart clicked right into place just above the first, scoring another bulls-eye. I could hear the room drop silent, as everything was on the line, now.

As I reached for the last dart, I could hardly maintain my composure, as I knew I was going to be enjoying Madelyn's oral skills in a short while. A practice wave to the board. Another. Letting it loose on the third wave, the dart sailed toward the bulls-eye on a perfect trajectory. I could feel every eye in the pub follow the trajectory of my dart in slow motion. It clicked into the two darts already in the target, then fell uselessly to the floor. No score!

I stood incredulous at the line as the combined breath of every patron in the pub was let out in disbelief. As I slowly turned back to our table, I caught a glimpse of Madelyn. She had a bit of a smirk on her face. Then she blew me a kiss, winked, and turned away. By the time I got back to the table, she had gone to pay our tab. Our opponent needed to stroke 80 points to go out, and he did so with two darts in the double twenty, a classic dart out. As the celebration began and the payouts were distributed, Madelyn returned to our table, and clapped me on the back. "I have some ale stashed at home, shall we drown our sorrows?" I asked, hoping for another chance.

"I just phoned home! Jim and Phil brought home some more ale, and there's talk of an after-hours starting up! I am so excited that Phil is there, I have a need, if you catch my drift!" Then she winked and smirked. My defeat was complete at this point. Phil was the on-again off-again fellow she had high hopes for, yet he only seemed to seek her out when he was hard up. My chance of enjoying her ministrations was dashed by misfortune at every turn. Keeping my composure as best I could, I feigned enthusiasm, "great! Let's get home to Jim and Phil, and see who else will come and party!"

Oh well, I thought. At least I have more fuel to feed my fantasies of Madelyn while I stroked myself into a soaking climax, later.