Win Win, When Losing a Bet

My pleading doing little to trigger Ali, who had just one goal and that was to have me cum on his big cock. My head tilted back, eyes rolling, not even feeling my legs any more, a wave of burning heat build-up where Ali and I connected. Like a rapid fire it went through my body...Causing a warm sensation to rush through me. Suddenly I was conscious of every nerve ending in me. My hands cupping my breasts and pinching my nipples, as the fire felt like it was erupting there. My pussy had clamped down so tight it had forced Ali out, who was holding me now, while I slowly came down from my climax.

"Are you OK dear," He asked, his hands around me softly caressing me.

I turned facing him. "More than OK."

Our lips met and our bodies were locked together in a long embrace. Ali rolled on his back and pulled me on top, his excitement pressed between us. I knew he wanted more, but I was not ready for his big cock to invade me again. I slowly slid down, kissing my way down his body. Rising up a little to let my breast hang below me and brush along his chest. His cock twitched under me, with my lips reaching his chest. Kissing his pecks and giving a little bite on each of his nipples. Further down, my breasts now closing in on his cock. I knew he was watching and enjoying my little tease. I leaned down to feel the throbbing of his hardness between my tits. Swaying side to side a little, to rub him some more. Ali moaning with content, my lips reaching the top of his six pack.

My breast now pressed down against his thigh, as my lips started kissing around his cock, deliberately avoiding any contact. It jumped up and down with each kiss, causing a streak of clear juice spilling from its tip onto his stomach. I looked up, smiling and moved further down. It was the first time I really got to take in his body up close and I was appreciating every inch. Making my way down one of his muscular thighs and lifting his calf. Completely tanned and very lean. Gently kissing the sole of his foot, looking at my lover who was melting in my hands. Relaxed and with content he watched me suck his big toe between my lips.

Back up, my breasts grazing his legs all the way. His legs now slightly parted, I could kiss between his legs and flick my tongue across the underside of his balls before moving back down his other leg and giving it the same treatment. Ali was thriving under my actions. His moans and breathing growing in intensity after I had given his other toe a little blow job and was close to reach his manhood again kissing up along his inner thigh. A pool of his juice had formed on his stomach, which I could not ignore, collecting a generous glob before finally engulfing his cock with my mouth.

His hips pushing of the bed almost by instinct forcing him straight back against my throat. I backed off and grabbed his cock, before straddling his lap and pushing him back down on the bed. Carefully I manoeuvred myself letting his cock brush along my moist pussy. Grinding back and forth, slowly increasing the pressure to allow his cock to par my lips. Back and forth, ever so gentle, grinding my pussy along his shaft. It was me who had to stifle a moan, feeling his cock head rub past my clit again. I was still tender from earlier, but his slick soft mushroom was feeling wonderful. A few more times, I enjoyed teasing both Ali and myself, before I could not hold back any more. I Lifted up to aim his cock at my opening. Effortlessly I eased him into my honeypot that was overflowing with my own nectar.

This time I controlled the pace and the depth of penetration. Moving my hips back and forth, squeezing my pussy tight as I lifted up and felt the rim of his bulbous head almost escaping my pussy lips. Back down just a few inches, leaning on his chest, the angle just perfect for his cockhead to brush my g-spot. My cream escaping from my lips that were sealed around his cock. Ali moaned with pleasure, his hands on my ass trying to guide me and increasing my pace.

Deeper and deeper I allowed him to penetrate me. The pace growing till he was back at screwing me with long deep strokes. Holding my ass cheeks steady in his hands as he pumped his hips off the bed rapidly. My tits bouncing in the rhythm of his thrust. His breath short and deep, the signs of his approaching orgasm. My pussy tender and not far away from reaching another climax myself. I was growing up in his excitement, knowing he was desperate for release. Doing my best to keep my pussy tight around his shaft, milking him.

Two more deep thrusts was all it took. His warm seed flooding. At least as much as the first time, if not more, he kept pumping his cream into me. I could feel every twitch of his cock. Close on the edge, Ali grabbed my hips again and continued driving his cock back and forth. His goo now seeping from my pussy around his shaft. Silky wet and soft, his slowly deflating rod rubbing just the rights spots, I started to cum as well and I fell down into his arms.

For minutes we lay there, both content and in bliss. Not daring to move almost with his cock still nudged in my pussy. Our lips locked again and slowly our tender kisses turned more passionate. Ali had his hands on my bum and it surprised me he was maybe a bum man after all. Feeling his cock twitch as he kneaded my ass and one of his fingers pushed down between my legs all the way across my tight little hole and edge of my pussy. Moving back and forth, collecting the mix of his cream and my own juices from around his cock and smearing it back along my crack. His cock slowly growing hard again, filling my pussy.

His hands playing with my ass, pulling my bum cheeks apart, allowing his slick fingers to continue to tease my puckered hole. Slowly he pushed his index finger past my barrier and I was moaning in delight with his cock back to his full hardness moving back and forth in small circles as Ali discovered his new found target.

"Hmmmm you feel so good," I urged him. "I love feeling every inch of you rubbing my insides like that."

Wiggling my bum a little, pushing back at his fingers while he managed to slip a second finger past my tight sphincter.

There was no doubt what he had in mind, he had won fare and square and he was going to claim his price. The thought that his fat cock would soon be invading my ass caused a shiver to run through my spine.

"You are not thinking of what I think you are, are you?" I teased.

With that he twisted the two digits which he had fully buried in my back door. "What would that be my love?"

Feeling him stretching me like that had me moaning in his ear again and being filled completely on the other end by his cock had me squirming on top of him. Filled from both ends, every little movement rippled through the core of my body.

"You are not thinking of sticking that big cock of yours up there?" I responded, pushing my ass against his fingers.

"Only if you will allow it," he whispered in my ear. "But if you won't, you will forfeit our bet and I will have to think of another prize that I could claim from you."

Our game continued. My body warming up to the thought of giving myself completely. My young little ass soon to surrender to his desires. I kept teasing, while he kept preparing my tight butt.

"I thought your cock fits these much better," I said, lifting myself up from his body with my hands pushing my tits together.

The angle pushing his fingers even further up inside of me, pressing against his cock through the thin membrane separating my two most sensitive orifices. His hands had my bum cheeks spread apart, he started lifting me up and letting me fall down again impaled on his rod.

"They sure are magnificent," He smirked. "I'm sure I'll enjoy them again before the weekend is over."

With that he flipped me over onto the bed. His hands holding my ass up high and his fingers remained lodged inside while his cock plopped free. The last remnants of his seed seeping out from my pussy and running down my thighs. With one hand he collected some of the goo and smeared it over his cock. Then he pulled his fingers out, leaving my ass gaping open for e few seconds. Long enough to bring his other hand to my tight hole and pushing in three fingers that were still coated with his cum. The invasion caused me to burry my head into the pillow to cry out in a mix of pleasure and pain. I felt his knuckles sliding past the first ring, stretching me open.

"That's it love," Ali hissed with a husk tone in his voice. "I'm going to enjoy this ass of you so much."

A few strokes of his fingers had me squirming with delight again as my little butt got accustomed to the invasion.

"Are you ready for my cock love?" he asked. "You want to feel my cock deep inside of here?" His fingers pushed in up to the last knuckle.

All I could do was moan in agreement, "Hmmmmm yeah baby, fuck my tight little butt. Let me feel that cock."

Ali did not need any further encouragement. His fingers slipped out and were instantly replaced by his big cock head. Pressing passed my spinster. I tried to relax as he stretched me even more. It was too big.

"aaaahhhhh!" I screamed out. "Slowly babe."

He pulled back a little. I heard him spitting on his cock, lubricating his thick tool. Pushing back and forth a little, allowing my ass to adjust to his size. Deeper and deeper, I felt him invade my dark hole slowly. Eventually the pain shoots turning into waves of pleasure and I thought he was almost fully inside of me. I started to push back at him which was a sign for Ali to start fucking my wonderful ass. His hands grabbing both cheeks as he thrusted forward and at least 3 more inches of meat were shoved up inside of me before his balls slapped against my pussy.

"Ohhhh fuck babe... you're so deep ahmmmm," I moaned and pushed my face back down into the pillow as he started to drive in and out.

First slow, long strokes. Slowly building up speed he picked up his pace. Hammering my ass. His hands let go of my hips and with his full weight he pushed me onto the bed. His cock driving in and out like a piston. One hand reached under me and started working my pussy. Two fingers driving between my soaking lips. My clit pushed down on the palm of his hand each time he rammed his cock home from behind. Pinning me onto the bed. His other hand found my breast and was pinching my nipple. I was screaming from pleasure, my cries muffled by the pillow. I could hardly breath, and was gasping for air each time he pulled back.

The onslaught too much. My ass never had been penetrated so deep, his fingers curled up in my pussy, rubbing my g-spot, my clit brushing over the rough skin of his hand, my nipple being pinched and pulled, my flesh mauled in his hand, lack of oxygen with my smothered heavy breathing through the pillow, it was all too much.

"Ohhhh fuck..! Ohhh my God...! I'mm gonnnaaaahhhh.." My body exploded in a shattering orgasm, first making my muscles to clench tight, then starting to tremble underneath Ali before it went all limb.

For a maybe half a minute I must have been out. When I regained consciousness, I was on my back with Ali next to me.

"Wow, you scared me there girl," he said. "Maybe you should do the driving again?"

His cock still standing proud, slick, wet and bright red from taking my ass.

I climbed on top, squatting above his meat. My ass still stretched, it almost appeared easy to slide his fat cock back in. But I did not take him all the way, just started to hump up and down over the first couple of inches. Still plenty enough to fill me out, I could not believe he had shoved all of that up inside me before. I leaned down to rest my hands on his chest, giving Ali access to my breasts that were bouncing up and down with my movement. Still so sensitive, I was already feeling another orgasm building up inside. The warm sensation just spreading from where I was joined with Ali, all through my body, from head to my toes. His hands massaging my tits and playing with my nipples, was like firework exploding inside. I started to bounce faster, my legs tired from squatting up and down, but I could not stop. Too close, to desperate to climax again.

"Hmmm play with my pussy," I pleaded. "Make me cum again on that big cock of yours."

Ali did not argue and reached with one hand between my legs and started rubbing his thumb in circles around my clit.

"Ahhhh fuck... Stop teasing me you bastard!" I moaned, now bouncing up and down his cock and grinding my hips side to side, desperate to feel his touch on my clit.

He teased me some more, but soon his thumb had homed in on it's target. The sensation was incredible. My legs gave in and I collapsed back on top of him. Trembling uncontrollably, as an other orgasm washed over me. Not as big as before, but it had me exhausted. In contrary to Ali, who just seemed to have gotten more excited. Flexing his hips he started to take over again and was driving his cock back and forth again.

"Ohhhh fuck Ali... you gonnnaaa ruin me forever... hmmmm..." I moaned loudly with my head next to his ear. "Ahhhhh fuck... cum in my ass you bastard... claim your prize and give me mine...ahhhh"

I bit my teeth in his neck, holding on for my dear life as jack started to fuck my tight hole in a blur. His balls slapping against me, rapid strokes, in and out."

"Ahhhhh yesssss..." He yelled. "I'm going to fill that ass of you... yeaahh"

One, two, three more times he repeated his claim, before his body stiffened up and I felt his cock swell up inside me and fill my bowls with his warm seed. He was spend, we both were. I rolled off completely exhausted, so was he. Getting his breath back.

I looked at him and said, "I think we both got a win out of this game."

"I think you are right," Ali agreed. "Can't wait for the next one."

This was just the start of a fun and sex filled weekend. Not even 12 hours had past since I lost my bet and after a little rest the following 36 hours turned out even better. Maybe I'll continue it in another story, but this was definitely a Win Win already.