Win Win, When Losing a Bet

I've never been much of a soccer fan, but betting with Ali always made it fun to watch a game. I had met him about 2 years ago on a night flight to Istanbul. He had treated his wife and daughter on a trip to Paris. Ali and his daughter were seated in my aisle of business class. She was so cute with her big mini mouse cuddly toy in her lap all the time, sitting in the single row window seat, while her mum and dad sat on the other side of the aisle in the centre. With his wife next to him I tried not to be too obvious of giving him a little added service and making sure he was well taken care of. He was mid 30's and extremely handsome with his dark curly hair and almond coloured skin. It was no wonder he had such a beautiful wife sitting next to him. Her dark straight hair looked like silk and the dress she wore showed off her tiny perfectly framed body. Yes, it got me a little jealous, I admit. It should not be a surprise I was quite worked up too, but even though I can be quite the little slut in the air, I have my standards too. No messing around with married men. Well, not when their wife is on board as well and especially not with their little offspring next to them. But that did not stop me from flirting a little. Or maybe a little too much.

After the dinner service, Ali had swapped seats with his daughter. She was now seated next to her mother and pretty soon they had both fully reclined their and were fast asleep. Ali on the other hand, was awake and ensured he got as much attention from me as possible.

"Are you this friendly to all the passengers?" He asked, with his eyes glooming up my thighs as I kneeled aside of his chair to put down his 3rd GT.

"Only to the kind ones," I smiled. "Just call if there is anything else you need."

He did call, several more times. Asking for some snacks or another drink. It was hard for him to hide his appreciation for my attendants in those khaki linen pants that he was wearing. Me loosening two buttons of my uniform and kneeling with my legs slightly parted next to him, did not help either.

While I served his 3rd GT, his hand was right on his bulge when he asked, "Do those lushes lips ever give anything else to a kind passenger, other than that lovely smile you have been serving me with each time?"

I was not going to lie, I would have loved to have taken care of him on that flight, but not with his wife and kid there too. He did kind a get to me though. Those are moments you end up thinking about, the ones that build up the excitement in your fantasies. What could have been? What would his cock feel like? He packed a pretty nice bulge. His hands looked strong and firm, I'm sure if he had cornered me in the galley, he could have made me. So, what was I to say to his question?

"Only if the setting is right and you earned a more in-depth lip service." I answered, feeling my loins burning.

I looked over to my side, seeing his daughter asleep next to his wife and I'm sure he understood. It was one of those flights where I needed to land a hand to myself to get me of this edge. If I hadn't, I might have ended up crossing some of my boundaries with Ali. Especially when shortly after he surprised me and walked past me in the galley to walk down the other aisle where his wife was seated. He gave me a little smirky grin as I looked up from the magazine I was reading. He sure was handsome, his muscular torso framed by a casual but stylish linen shirt. A few minutes past, when his wife appeared on the opposite side of the galley and went into the lavatory. She looked a bit nervous at me before she went in. Not much later Ali appeared again. With the same grin he looked at me and opened the lavatory his wife just got into. The grin that telling me what I was missing and at the same time he knew I was not going to stop him. Well, as long as they were discrete about it, I surely was not going to make a fuss of them joining the Mile-High club on my watch.

I could not concentrate on reading my magazine any more. They were in there for quite some time. First, I made a round down my aisle to see if everything was still OK. I even checked on their daughter, tugged in under a blanket, still with her cuddly Mini Mouse in her arms. Then down the other aisle, most of the passengers asleep as well. Back up front, I walked slowly past the lavatory and paused for a few seconds. Over the noise of the plane I could faintly hear her moans, which just made me horny again. By her soft cries, I could make out the steady rhythm of Ali driving his cock into her. I could only imagine her pleasure, the same I have experienced so often mid-air. Wondering if she would get hooked on the thrill of flying, like me. Hooked on this high for reaching an orgasm in the thin air from flying at high altitude. Or just the thrill of getting away with something you shouldn't be doing. Everything really.

I listened some more, standing to the side into the galley, out of sight from the cabin. She was approaching her climax, I could tell. Surprisingly I could not make out any sound from Ali. It went silent, but the door remained shut as I made my way back to take the jump seat and pretend to be reading my magazine. For ten more minutes I sat there, imagining what they were doing. I knew darn well. He was getting his lip service. When the door finally opened, his wife appeared, rushing back down the aisle. Ali opened the door after she had gone, while he was still pulling his pants back up. Smiling at me again. He walked out towards me, removed a card from his pocket and handed it to me.

"I hope we can find the right setting some time so you can tell me the terms for earning more than a smile." He said and walked back to his seat. Pretty soon after my colleague was back from his break and it was time to prepare for landing and I was too busy making sure the cabin was secure to get further distracted. After we had landed, they walked off the plane like a happy beautiful family. Seeing him with his daughter and wife next to him, I knew I was probably not going to take him up on his offer.

I didn't, but after I got back home in France, I did send him an e-mail to excuse myself for not being able to get in contact. Seeing him with his family, I could not interfere. It was just a short message, but I almost instantly got a reply from him. He understood, but still was disappointed he did not get to see anything more than my smile and cleavage. I told him that I was not sure he would be able to control himself if I had shown him more. Pointing out how he had woken his wife for attending his needs in the lavatory during the flight. We started a regular exchange and I told him as much about myself as he did about him and his family. His marriage was more an arrangement of convenience. Two powerful and wealthy Turkish families, securing their legacy. At this moment all expectations are set on their daughter, but from both sides it's expected they would have a son in the near future as well. He admitted he was lucky to have such a young and beautiful wife, but there never had been any love and sex was not a commodity at all. In fact, they both had more extramarital sex than what they did in their own marriage.

Both of them had PI's contracted to spy on each other. Mistakes or behaviour that could damage the reputation of one's family was being used as bribe to get what they want from the other. The visit to Paris was one of her demands, which he had easily obliged to, knowing his daughter would love the side trip to Disneyland. During the flight back he had pulled one of his own trump cards and made well use of it after I had gotten him all worked up but was not willing to play. In fact, he was convinced I owed him big time. At first, I was feeling a bit sorry for them using each other like that. Then I grew a bit sceptical about it, because what can you believe these days on what others say. But for some reason we kept communicating and our conversations became the least but boring.

"How could he earn his prize?" came his question in one of his messages.

"So you think you can win me?" I teased. "Maybe you should put your money where your mouth and see if you can beat me in a game."

"How about a bet?" he replied.

That is how it all started. An innocent bet on a soccer match. He lost and it was my joy to collect my prize instead of him.

"Show me as much of yourself as you would like to see of me." Was all I had sent him in my message to collect his dept for loosing.

The next e-mail I got I was looking at a series of pictures of him slowly undressing. He had made little remarks at each one of them, telling me how it would be me next time. He was handsome and he seemed to enjoy showing his body. He was not really buff, but was fit and his upper body and stomach showed some lovely muscle tone.

"Are you getting warm yet?" was his remark under his picture where he flexed his abs.

Not that I admitted it to him, but I was enjoying looking at his pictures. Scrolling down to see more. He was wearing similar linen pants and just like I had observed on the flight, a prominent bulge was showing down his left leg. This was getting interesting. The next one his hands was tugging open the linen waist band.

"If I lower my pants you will have to do the same when you lose your next bet," it had written underneath.

As if I would lose next time, I scrolled down. Down his pants were as well. His plain red boxers tenting outwards by his hardon. I had not expected this after winning the bet, the fact he was so confident showing himself like this. Cocky almost, that same smirky smile I had seen during the flight when he took his wife to the lavatory. On the next pic, his fingers were tugged into the waistband of his boxers.

"Are you ready to go this far?"

I was already scrolling down, my instincts and desires had already taken over and I was feeling extremely horny. Unexpected indeed. I'm used to these feelings when I have to fly. The teasing, flirting, physical contact. The unexpected lingering of a hand, or the guy staring your down. But this was just an email from a guy across the Méditerranée. A very handsome guy and one I enjoyed flirting with for a little bit on that flight, but still. These were just pictures. It must be unfinished business. Somewhere my desires were not fulfilled yet from that moment we met.

The picture comes in view and Ali is standing away from his camera. Showing me his butt cheeks. They are only slightly lighter than the rest of his darkened skin, the faint tan line makes me wonder if he sunbaths naked. Just a thought and a fantasy blossoms in my head. Naked together on a beach, I'm tending to him, rubbing lotion on his skin. His back, his legs, his thighs and butt. He turns around. By now I'm scrolling down with one hand while my other hand has found its way in my shorts.

"Is this really happening?" I wonder, continuing to masturbate and think of us on that beach.

But there is no other picture. Just a phrase at the bottom. "If you are ready to show me yours, I'll show you mine."

It's almost like being back in high school. But the craving inside me is definitely not the same. I want him, I want to see all. Was this a dare? Do I have to pay-up, even though he lost his bet? My other hand still busy in my shorts, playing with my wetness. Rubbing my fingers between my slick vulva. Finding my clit, fully engorged and free from its hood. I moan, closing my eyes and just imagine Ali on his back. How wonderful his cock must be. The way he pleasured his wife, I want to feel his pleasure rod inside me. Stretching me and his length rubbing along my clit as he slides in and out. My fingers go crazy at this time. Driving into me and back out to moisten my clit. My breathe heavy... Moaning in pleasure as I desperately seek a quick relief. I keep rubbing myself in a frenzy under my shorts and feel my legs stiffen first. Then my back arched and my head fell back over the back of the chair. Moaning out loud as my body starts to tremble on the chair.

"Fuck... damn you Ali," I was thinking to myself as my orgasm subsides. "I'll make sure I'm going to win again."

With one hand I hit the reply button and write, "In case you will ever win a bet, that's all you get to see as well."

Our exchanges continued. He travelled to some nice places and showed me some other pictures. Then at one point I get this message from him. His team Galatasaray is playing against my home team Bordeaux in a group match of the Champions League. Ali was so excited and made it sound they already had won the match. He was so sure that he upped the stakes. Not only would the winner get to make one request from the loser, but they could make an extra demand for each goal they scored during the match as well. Off course I had to accept, though I didn't know anything about soccer. The days up to the match I was reading about the teams and the odds and it got me excited even before the match was played. The day of the match was a disappointment for both of us, ending in 0-0.

The next day, I got an email from Ali, telling me there was going to be a return match in Bordeaux and the bet was still on. It was two months later when I was with a friend at Stade Chaban-Delmas, cheering for Bordeaux. The first goal was made and I felt my excitement rise. It stayed 1-0 till the end of the first half, but in the second half they made two more and my panties were getting wet. Towards the end Galatasaray managed to get a goal in, but with the winning team and three goals in the pocket I was ready to make my demands.

Maybe I was mean, or just over excited. But my demands were tough and very naughty. First one was a request for him to Edge himself. On the hour for twelve hours and not allowed to cum. I made him write every detail of what he did and what he was thinking. He made me wait, but got a very long reply, with all the saucy details of his secret fantasies. It was so hot reading them, I enjoyed myself multiple times. The next request was to pick his favorite one and tell me more about it in detail as I allowed him to jerk off and cum this time. Again, a long reply and I was sure he was enjoying losing this bet as much as I did. His fetish to cum on my face and breasts was very clear by this time and I owed him at least a little reward.

He got a first picture of me. My third demand to him was only to show me how much he liked to cum for me again. The result was a blast... Well quite a few blasts that were displayed all over my picture that he had send in return. Two more to go and I wanted to tease him a little more. All this time I was still yearning to see his cock... But just getting a picture would be too easy of a challenge by this time. I got him to get hard and tie his cock and balls in a thin rope. He should stay hard all the time, but not cum, until I would approve of the pictures.

The result was more than I could have hoped for. His lovely thick rod tied in knots. His cockhead deep purple and swollen. I wanted to have him there and then, but I had to do with the next best thing, my favourite Fun Factory Tiger. By the looks of things equal in size and girth to Ali's meat. After my third orgasm I wrote him back. Sending a picture of myself sunbathing in the nude. Not allowing to remove the restraints on his cock, I asked him to get off too. He did... covering me again.

I was surprised as how far I had taken this, what it did to me and just how I shared a nude picture of myself so easily. In the air, I'm always so careful. Never write anything on paper, don't get caught on camera and don't leave your details. Rules I stuck by so long and here I was breaking them. Hell, this story on its own is evident enough of how caught up I got.

Our interchanges were a lot milder after this, less demanding and more sharing. Thoughts, fantasies and kind. More pictures of his latest travels, some of the beautiful surroundings and buildings. I know he was missing our interaction, but after beating him twice Ali was not quick to make a new bet. His fantasies were still pretty wild and I enjoyed reading them when I was alone. It was still the beginning of my career as attendant and I had my fun as much as I could.

That changed at the beginning of the following year. Bordeaux were in an UEFA Cup match against a small team from Spain. I learned about this of course from Ali. He told me that he thought Bordeaux was the better team, but that he would be a gentleman and let me pick who I thought was going to win.

"Bordeaux of course," I replied with full conviction.

Same terms as before. One open request for picking the winning team and a bonus request for each goal they score. It was Valentine's day and I was flying during the match. At the crew briefing and on board I had put on my best game seducing the co-pilot to allow me to sneak into the cockpit every now and again and ask them to get a message down to the base for an updated score. Both him and the pilot were amazed by my excitement for soccer, which did pay-off in a very pleasant way after the final score became clear. All the build-up excitement with the end result becoming 0-0. It was not till the next day when I left the co-pilots hotel room for some rest, that I read Ali's e-mail.

"The return is in one week on the 22nd in Pamplona, can you be there?"

Still tired from the flight and sexcapade with the co-pilot as pay-off for providing me live updates on the match, I checked my agenda and send a quick reply.

"I'm off till Sunday, so yes. Are you...?"

In my head I started to wonder if you actually would fly over for this. Too tired to think anything else I fell asleep. It wasn't till late in the afternoon and I read my new messages. The first one, full of excitement, telling it was a date. The next one, two VIP tickets for the match... And the fact I was going to meet him in a weeks' time started to sink in. The next was his flight ticket, arriving the day of the match, I leaped from the bed. Excited and a little worried. It was just a game before, exciting but with a safe distance. What did I know about him after all?

"This is not part of our bet, but we need to have a place to stay," read his next message with a link to a reservation for a two-bedroom suite at the Alma Pamplona. "To make you feel at ease, it has separate bedrooms"

Suddenly thoughts ran through my head of the fantasies he had shared with me. What if I would lose the game this time? Would he be claiming his prize to live out some of those fantasies with me. To distract me a bit I went to the gym for a workout and afterwards a dip in the pool and visit to the Hammam. There I bumped into Stuart the co-pilot again. If you made your bed, you have to sleep in it, and so I did. We had dinner together and visited a bar for some drinks before heading back to his room again. It was wild. I was so charged up about this whole thing, I could not get enough. Stuart probably thought he was the greatest stud driving a girl crazy like that. If only he knew, my sex drive was driven by thoughts that were not about him at all.

I made it back home the following day without any embarrassing moments. Three days later I had a back to back to NY and with the short layover and time difference I was too tired to even think about what was about to happen. Bordeaux was the better team anyway, so I would probably end up on top. Wednesday morning, I was back home, just enough to get a good rest. Thursday morning a visit to my local beauty salon and then I was off to Pamplona. Just over 3 hours drive from where I lived, so I was there well in time. Valet parking at the hotel and the porter knew my name and led me to the suite. He advised that my guest would arrive in two hours.

The trip had gotten me a little sweaty, so I showered, making sure not to wet my hair. The stylist had worked miracles to make it straight. From my first and only soccer match before, I had brought a jersey of Bordeaux to wear, together with some cut of shorts and sneakers. Maybe a bit too casual... even though I was wearing a sexy lace string and bra underneath. When Ali entered, his face and reaction told me different though.