Win Win, When Losing a Bet

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I stood, pulling my arms close to my chest protecting myself. The men surrounding us. Ali was there. Right in front, pulling me close and starting to dance with me.

"Relax," he whispered close in my ear. "You are amazing, I will not let anything happen that you don't like."

He held my hands and pulled them gently free. I trusted him, I was his prize and even though I was very conscious of all the men nearby, I knew I could trust him. Six of his guards were there to take us away if I wanted to. My hands lowered and the dancing continued. The girl tossed her top as well and she was surrounded by an entourage of fans as well. More sangria, hands around my waist, bodies pushing into me. Numerous of hard cocks, only blocked by a thin layer of their football shorts, brushed against my ass and thigh. Some sangria spilled onto my bare flesh with the men bumping against us. Ali lowered his head and covered one of my nipples with his mouth to clean up the juicy wine. The crowd going crazy and I was in full in ecstasy. The sensation of his warm lips sucked around my hard nipple drove me crazy. Suddenly I flinched when I felt a hand slide into my shorts.

"It's me," Ali whispered in my ears to reassuring me. "I want to get a taste of my treasure."

His fingers eased under my panties and slid effortlessly in between my moist lips. I quivered as the palm of his hand pressed against my exposed clit. Leaning into him, I bit down in his shoulder, preventing me from gasping out loud from the climax that suddenly struck me. Leaving me weak on my feet as he withdrew his hand and lifted me up. One of his guards covered me with his blazer while Ali carried me away from the crowd. His drivers were waiting maybe not even a hundred meters away and soon I was alone with Ali in the back of the car driving to the hotel.

My head was spinning, all those men rooting for me. Grinding against me. How many different cocks had been poking against my bum? I was not even sure what had gotten over me, but I was save with my lover. His hands caressing my naked flesh under the blazer, reminding me that it wasn't just a dream. The thought just exciting me again and I could not wait till we were back at the hotel.

"You are truly amazing my dear. The only true winner tonight" he whispered with his hands cupping the underside of my breasts. "Not even the entire soccer team of Pamplona can be a match against these."

"Are you trying to make another bet?" I asked, feeling very naughty. "These two against 11 men, now how would we declare a winner?"

That naughty smile showed on his face again, "Would you like to? I don't think I could afford the stakes, but I'm sure you are more than capable to defeat any men."

I was lying in his arms, my own hand resting on his thigh. His excitement evident under the thin nylon fabric of his football shorts. I could not resist tracing my finger upwards along its length. I knew what it looked like from the pictures that he had send me, I had felt its thickness squeezing it through these same shorts earlier and right that moment I got a pretty indication of how well he was equipped. The bulge protruding about 8"down his left leg, the tip almost clearing under the edge of his shorts, where a dark spot had developed.

Without anything being said, my fingers hooked under his shorts and pulled them back slightly to reveal his bulbous head. Slick with his juicy fluid, which continued to spill out from its tip. Taking hold of it just below the purple mushroom, I could not close my fingers around his thick shaft. His chauffeur might have gotten a good view in his rear-view mirror, but I did not care. Neither did my intensions seem to bother Ali, who was clearly enjoying my actions. Stretched back against the leather seat with his eyes closed and head tilted back. Even though I had lost the bet, here I was unwrapping my own prize. And what a magnificent gift it was. I lowered my head, hungry for him. The soft moan from Ali, evident he approving my next move as my lips pressed against the tip and slowly stretched around his thickness to take him in. I probably had only access to a third of his length before his shorts got in the way and my mouth was filled to the hilt. His goo running straight down my throat. Pulling back for some air, I let my tongue run along the back of his cockhead, causing another loud moan from him and a strand of clear juice to run down from my tongue onto my lips.

His eyes open now and looking straight at me as I looked back up at him, licking my lips. His hand moved from my breast to the nape of my neck. I was expecting him to guide my head back onto his cock, but instead he pulled me back up. Kissing my lips, spoiled with his juice. He was more aggressive than before, wild, passionate. \

"You better put this on, we are almost there," he said with a deep tone in his voice. "It won't be long before you will be able to finish this." Pulling back his shorts to cover up his manhood.

Putting on the blazer, I arched my back to slide my arm down one sleeve, giving him and the driver one last view of my firm mounts. My nipples still hard like razors sticking out form the puffy areolas. His lips found one of them, before I could slip in my other arm. The soft bite of his teeth on the bright pink sensitive flesh made me squeal, but it also put more fuel on the fire burning inside of me. Ail pulled his mouth back sucking down hard one last time, making my nipple plop free.

"I'm going to wear you out," I warned him, slipping my other arm into the blazer and closing it up half loose at the front.

Ali smiled in agreement as the car had stopped at the front of the Hotel and one of the valet boys opened the door. The young lad tried to be professional, but as I got out with the blazer doing not much of a job covering me, he could not hide the look on his face with his eyes staring down at me. No tip needed; his effort was paid off plenty in kind. It was late, so the lobby was petty empty, though we did get some more looks from the two girls at the counter. We were too far away for them to get as clear a view as the valet boy, but I'm sure he was going to fill them in on one of their breaks that night.

The elevator ride to our suite was too short, but Ali pulled me in for another passionate kiss. The bell reminding us we had reached our floor and the doors opened. Just a few meters down the hall and we were at the entrance of the suite. My hands tugging on Ali's shorts as he tried to find the key card.

"I don't have the key," he declared as I was squatting down before him. "I left the in the pocket of the trousers I was wearing earlier."

With my fingers already hooked in the waistband of his shorts, I did not even listen to what he said. I pulled them down in one go, freeing his cock, which jumped up straight in front of my face. It looked even bigger than I had thought. His veins swollen along the side of his shaft, the head deep purple, aching for my touch. I heard Ali talk but was not paying attention. My lips had already found their target again, enjoying his taste. His thick head pressing at the back of my throat as I tried to take as much as I could. Pulling back, I looked up and noticed he was on the phone. A new challenge, could I get him to moan, before he would hang up. I tried, sucking him back deep again, but there was just no way that I could take him completely. So I released his cock and grabbed hold of it at the base. Pointing it up I licked the underside and flicked my tongue across the rim of his cock head a few times. I felt it jerk and twitch and licked and kissed my way down his shaft before reaching his testicles. They were tugged tight under his shaft. Full and ready to cum. I had to suck hard to get one all the way in my mouth. Bathing it and lapping my tongue at the end of where it attached to his body.

"God ahhhh..." He moaned "You are one devil woman driving me crazy like that."

He had already hung up the phone. I sucked in the other, enjoying how Ali bucked his hips with one of my hands gripped tight on his cock.

"Ding," I heard the bell of the elevator and was ready to jump up, but Ali had his hand on my shoulder to keep me squatted down.

"Don't you dare to stop what you started," he commanded

After what had happened so far, I could not really care anymore. A few seconds later the young guy that had helped me out of the car was standing inches away from me, while my mouth worked on Ali's cock. I could feel his eyes staring at me.

"Thank you for the key Carlos," I heard Ali say. "Do you want your tip now, or some other time?"

"Now would be good as ever," he said with a strong Spanish accent.

My heart started racing like mad, when he started to unzip his black slacks and pulled them down in one go along with his boxers. His young prick already erect. Compared to Ali, it looked small, but must have been still 6" inches long, but he did not have much girth. I knew what was expected and wrapped one hand around his shaft and aimed it at my mouth. I looked up at him, slowly parting my lips and sticking out my tongue. The young lad desperate for me to take him in. I licked his bright pink cock head a few times to make it wet and soon had him bucking his hips while I held him tight, squeezing his clear pre-cum onto my lips. He was breathing and moaning heavily even before I had started to suck him and I knew the young inexperience boy was no match for me.

My lips sealed around his shaft and I sank my mouth down onto his cock. Looking up at him, I started to bob slowly back and forth. Purposely letting his cockhead hit my throat each time. The pressure stimulating his sensitive head, had him on the edge within minutes. His cock jerking and growing even harder. I released my grip and looked up at him. This time pushing my mouth fully down over his cock. Letting his cock head slide down my throat. He started to jerk and came immediately. Warm streams of his seed shooting down my throat. Withdrawing a little, I grabbed his slowly deflating cock to squeeze the last drops in my mouth,

Like earlier in the street, it all just happened. Carlos was already pulling back up his pants and Ali had opened up our suite with the key had gotten from him. He lifted back up on my feet and guided me inside. His shorts remained in the corridor with the door closing behind him. My little display with Carlos seemed to have gotten him even harder and it was clear he longed for some similar satisfaction. His tongue darting between my lips with his lips pressed on mine while he pulled me close. His hands caressing my bum, while his cock was pressed between us. The head spilling more of his juice onto my bare belly. It was just e few seconds, before his hands moved up my back to grab my hair and pull me back.

"You sure have one hell of a mouth," he sighed. "I'm dying to find out all of its talents."

There was no need for his hand on my shoulder, I was already sinking to my knees to give him his long-awaited prize. Just holding it at its base was causing a thrill to run down my spine. For the third time I got my lips around his crown. Still amazing me how wide I had to open my jaw to allow him to enter. I bobbed back and forth for a bit, taking him a little deeper each time. The blazer was just too hot for me, and I let my hand go of his shaft so shed the jacket from my shoulders. With free reign, Ali held my head and started pumping his cock back and forth... A few times causing a little gag reflex and as he pulled out, his cock was slick with my saliva. Mixed together with his precum, it ran from my lips to the tip of his shaft, till it broke loose and trailed from my chin down between the valley of my breasts. Again, he slid back between my lips. His cockhead stretching the back of my throat, rubbing my tonsils as I managed to almost swallow two thirds of his rod.

Each time he pulled back to allow me to get some air. My breasts getting more and more slick with his juice and my saliva. Ali getting wilder and wilder. He paused and reached down to cup my breasts. Kneading them in his hands, with his cock twitching right in front of me. I looked up and saw the desire in his face as I stuck out my tongue to flick across the underside of his helmet while he continued his play. He eased me back up and turned me around to push me onto the large king size bed. Following me with that big cock of his swaying side to side. I could not get enough of it and I was ready for him to take me. Ready to have him stretch my horny cunt, ravish me and fill me with that fat monster of him.

But Ali had different ideas, pushing my legs together again and straddling me above my waist. His weight pinning me down on the bed, with his hands reaching for my soft melons again. Finding my hard nipples, he pinched them, making me squeal and thrift under him. His big strong hands squeezing and massaging them harder than before. He scooted a bit higher putting his big cock right between them. Pressing them tight together, moulding my soft flesh around it.

"I'm going to ravish every sexy little piece of your body, starting with these wonderful puppies," he said with a hoarse voice and started to buck his hips back and forth.

His slick cock sliding effortlessly between my tits. The shiny head and part of his rod appearing above them as he forced himself all the way upwards. His movements were getting jerky and wild, with deep moans of pleasure escaping his mouth. His breathing short and erratic. All the build-up excitement of this evening started to claim its toll, his desire taking over. I lifted my head and parted my lips to welcome his cock head with each upward stroke. My tongue bathing the underside of his cock and flicking across his frenulum. This was too much for him.

The first few globs of cum started to seep out from his cock head, dripping down on my chin. Then on the next upward stroke his cock exploded with a large volley of cum that soared over my face and landed on my forehead and in my hair. I sealed my lips around it just in time to receive a second blast that shot against the back of my throat. Ali pulled back and before he could aim his fire hose down at my breasts a third jet of cum painted my face, followed by two more blasts to cover my tits.

The image of him cuming on a picture of me that he had shared by email a few months before, did not do any justice to the way he came just then. I savoured his taste as I let my head fell back onto the bed. Ali falling next to me, exhausted from his climax. He leaned and surprised me with a warm kiss. Not backing away with his sticky goo stuck to my face and lips.

"Let's get cleaned up in the shower and see if we can get this one ready for round two," I said, pulling away and grabbing his deflated cock.

It still felt pretty big and my words and touch seem to bring back new life to it already. Lathering up our bodies with a body wash of lavender oil, he was indeed back up to full mast with not much effort. My breast got plenty of attention. Now there are men that like bums, others like legs, some are crazy about feet, but Ali for sure was a tit man. Just playing with them under the shower got him all excited again. Turning to face the wall and shower head, with his cock sliding up and down my ass crack, he still had his arms around me to cup my soft mounts and play with them. Not that I minded, I was having fun with my own big toy. My hand reaching between my legs to position his hard rod between my legs and allowing me to grind my swollen pussy lips back and forth along his shaft. Just a little pressure, to part them and feel his veins rub across my exposed clit. I was desperate for him, my pussy moist and slick from my own excitement. It had been that way since the second half of the soccer match. The orgasm his playful hands had set off in the middle of the street, had not merely taken the edge off.

I moved back and forth, but he was just standing too tall for me to get the right angle so I could mount his wonderful toy. Finally, he got the hint and bucked his knees a little to position himself. He had to let go of me to steady himself against the wall, but with one thrust he drove home, leaving me gasping for air as he pinned me against the wall. His cock stretching my inner walls, I could sense every inch of him entering me deep. A shoot of pain when his cock head pressed against my cervix. He felt it too and pulled back, only to drive back in a second later.

"Ahhhh fuck you are too big.. ouucchhh..." I squealed with his cock driving in almost all the way.

Again and again, the pain turning to immense pleasure as I got accustomed to his size and he started to pound me with all he got. Deep long strokes, my breasts against the wall, arms held up above my head. Ali finally found my bum, holding them as he guided me back and forth on his dick. My squeals had turned to loud moans, heavy breathing and my legs started trembling... A first orgasm washing over me.

But Ali just had started... After he had spoiled his seed all over me not even 10 minutes before, he was going to last quite some time. My knees gave way and Ali held me up. He turned me around and lifted me up to allow me to wrap my legs around his waist and he drove back into me with my back now against the wall. His lips found one of my nipples, sucking away on it while his hands lifted me up from his cock a little bit each time and letting me fall back down. With my legs wrapped around, my ass was free game for his hands and his index finger had found my butthole. At first he just rubbed and fooled around it for a bit, but then he suddenly pressed in.

"Hmmmm naughty...", I moaned in his ear. "You trying to find out how dirty you can get me..?"

I clenched my bum as he moved back and forth... Fucking his big rod and finger at the same time. Ali was loving it, moving from one tit to the other with his succulent lips. In between kissing me passionately and telling me how wonderful my pussy felt on his dick.

"Ohhh its your cock that makes it so good," I moaned. "You are splitting me, ahhhh"

It almost felt like that, and I was loving it. But the position was getting too tyring for Ali and he put me back down. We dried off quickly and jumped back in the bed. This time my open invitation was welcomed with Ali climbing between my legs. Kneeled below me, he lifted my legs over his thigs so he could guid his cock back to my pussy. But instead of entering me, he started to tease my pussy with his cock head. Spreading my pink puffy lips and running it back and forth. At the top he would tap my clit a few times, causing more moans from me, and all the way down, his slick cock head was rubbing my own juices over my tight little butt hole... Back and forth, I was writhing underneath him, trying to force his entry... Begging him to fuck me again. Ali loving every minute.

He lifted up a bit and grabbed my ancles, pushing them up towards my head, bending me in half like a pretzel. Resting on his arms he lowered his pelvis and let his cock head rub across my pussy lips again.. My hips bucked as he found my entrance. I watched him look at me. Seeing how his cock stretched me open as he lowered further...

"hmmmm yess please fuck me Ali, fuck me all night long..." I pleaded.

"Ahmmmffff...ooohhhh fuck.. yeahhh ... ahhh.. yeaahh.. ohhh fuck.. Was all that followed when he drove in and started hammering me like his life depended on it.

Another orgasm was approaching rapidly. My body stiffened and I gasped for air each time Ali pushed down deep into me. My pussy clinging to his shaft like a seal. Milking him and driving him on towards release as well... But I was too far already...

"You going to make me cum again... hmmmm cum with me babe..?" I hissed with the air pushed from my lungs. "ahhhh... hmmmmmpffff"