The Evolution of a Bet

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This story is quite a long one, and it takes a while to get to the sex, but when you do there is quite a lot of it. It covers a lot of different acts, but does not get any more ‘wild’ than anal sex. The story could fit into many categories, but this is probably the best fit for it. The setting is Australia, and there are some references to the local ‘Australian Rules’ football code. If there is any of this that you find confusing please make a public comment and I will try to explain it for everyone. Please let me know if you enjoy the story. BB1212


I have two rules that I consider to be my ‘unbreakable’ ones. The first is, never bet with your customers, and the second is never bet when the odds are strongly against you.

“You’re on,” I said with only a moment’s hesitation, breaking both of my rules at once.

Julie always pushes my buttons. She is definitely the most attractive and desirable woman that I have ever met. She is witty and intelligent and she always pays on time. She is perfect in every way but one, and that is her total and blind dedication to the Collingwood Magpies. Just about every football league has a team that totally polarises the supporters, and in the AFL (Australian Football League) it is the Magpies. The people who love them do so passionately, and the rest of us hate them just as fiercely.

I was about half way through a major project for Julie. I had to pave the area around her swimming pool, which was pretty heavy work, and I also had to put up a privacy screen to stop people who were passing by from seeing in. Julie wanted the privacy screen so that she could relax by the pool in the nude. The first time she said this I had an instant hard on that didn’t go down for at least thirty minutes.

Julie has a body that is perfect, she’s just a bit shorter than average, with tits that always look like they are going to burst out of whatever it is that she is wearing. Her waist is tiny and her hips flare out from it just enough to show that she is a woman, not a girl. Her delicate features are framed by a jet black shoulder length pageboy haircut. I see her on the TV most weekends during the football season because the cameramen at the football are really perverts at heart, and a pretty girl in a team jumper at least three sizes too small for her always gets found. That will happen even if the jumper has what used to be vertical black and white stripes before they were stretched so drastically out of shape. The fact that Julie always sits next to a girl similarly dressed but with blonde hair doubles the chances too.

Julie is also way too young for me. She’s late twenties and I’m early forties, so as much as I like to look at her I have never tried to take it any further. But she’s not an airhead or a bimbo, and she is earning enough money to get the new super privacy screens that I was selling as a side line. These things are spectacular, and they allow the people inside to easily see out, and totally block the people outside from seeing in, regardless of whether it’s lighter inside and darker outside, or if it is the other way around. I’m not sure exactly how it’s done, there are layers of finely polarised material and some one way reflective sheets involved, but they work and that’s what counts. Like I said, from the inside you can see out, but from the outside all you see is the pattern or colour that I print on a special machine in my workshop.

Our main argument on this job was about the patterns for Julie’s screens. She wanted vertical black and white stripes, with the Collingwood logo on them, and I wanted just about anything else. But Julie is the customer. We were discussing it yet again.

“I’ll do it,” I said reluctantly, “but if it destroys my machinery I’ll charge you for it.” Julie grinned. She is the sort of Collingwood supporter who at least acknowledges that there is another point of view, even if she is absolutely sure they are wrong.

“For the money I’m going to pay you’d better,” she said bluntly, and I nodded. The screens aren’t cheap.

“I still don’t like it,” I grumbled, and then she smiled one those smiles that tells any man with half a brain to turn and run. I mustn’t have even a quarter of a brain, because I didn’t even turn.

“I’ll make a bet,” Julie said slyly, “if you win this weekend you can choose the decoration. Anything you want.” I must have looked interested, because she then continued very quickly. “If we win I get a twenty per cent discount off the whole job.”

Twenty per cent on that job was substantial, but that didn’t really bother me. Eight years earlier I had won first division in Tattslotto. People think that when you win the lottery you are set up for life, but that isn’t always the case. There were a number of winners that week and I had ended up with a bit less than seven hundred thousand dollars. It was enough to let me make a total change to my life, but not enough for me to give up work all together. Anyway, I quit my job İstanbul Escort as a supply co-ordinator in a large garden supplies chain, and took up landscaping instead. Working for myself I could choose the projects I wanted to take on, and not being short of money I could allow enough time to do them right. As a result I got a good reputation very quickly, and the screen suppliers from Finland actually sought me out and asked me to represent them. By the time I was doing Julie’s project I was earning almost twice as much as I had been before I ‘retired’.

“You’re on,” I said with only a moment’s hesitation, breaking both of my rules at once. I knew that the chances of the Kangaroos beating the Magpies on the weekend were minimal at best, but I had this mental picture of Julie’s privacy screen being blue and white vertical stripes with the North Melbourne logo on them and I had to take the chance. Julie lifted an eyebrow.

“Really?” she asked.

“Yep.” Julie looked dubious.

“Can you afford that?” she asked suspiciously. I could see that she was now wondering if I was overcharging her.

“Not really,” I replied, “but the chance of having the Kangaroos colours and logo is just too good to refuse.” She looked shocked.

“You wouldn’t…”

“You said anything I want,” I replied smugly, and I put my hand out. “So shake or chicken out?” Julie stared at me for some time, and then shook my hand.

“We’ve got a bet,” she said, “I’ve just got to work out what do with the extra money I budgeted for the job.”

“Don’t count your chickens,” I suggested, trying to sound more confident than I felt.

The next day Julie gave me the chance to change my mind, and I thought that was really sporting of her. She knew as well as I did that the odds were firmly stacked on her side. Collingwood were the reigning premiers, and they had been almost unbeatable all year while the ‘roos were sitting in the bottom half of the ladder and had only shown a few flashes of their former glory all season. I knew I was throwing my money away, but as I said, I didn’t really care, and even the slightest of chances was worth it. We kept the bet.

By Friday afternoon I had the screens up on three sides. It was quite a job, because their strength was mostly achieved by interlocking them precisely together, and the foundations I had set into concrete had to be exact. Fortunately I was pretty well practiced, and the job was going well.

“I’m not looking forward to Monday,” I said, wiping my brow as Julie brought me a cold drink.

“Why’s that?” she asked, falling into the trap.

“Have to take them all down again to change the covers,” I said grinning, and she took a good natured swipe at me.

“Then the result will suit us both,” she teased, putting her hands on her hips and leaning toward me. I groaned silently as her chest stretched her already challenged polo shirt totally out of proportion. I swear that she must use wire to sew her buttons on; they should have been flying in all directions after that amount of force was applied. That incredible cleavage was just so distracting. I turned away and heard her giggle quietly. I had long ago realised that she was deliberately teasing me, but I didn’t care, the view was well worth it.

I was still single, and I had been since the week before my lottery win. At that time my wife of six years had finally decided she wanted to be young and free again, and in the ultimate irony I had left the court room much poorer and single, and had immediately bought the ticket that fixed everything my wife hated. She hadn’t liked that I was fat, but then again so was she. She hadn’t liked the amount I drank, but she drank too, and she hadn’t liked my job that kept me away from home so regularly. Our sex life had almost dried up entirely, and I think she was too nervous about being caught to have an affair. I had decided I could quite happily live without it, so I hadn’t gone looking elsewhere while we were married either.

Since the divorce my hard physical work had toughened and toned me up better than any gym could, and I can honestly say that I am now fitter and more ripped than most men who are half my age. I have cut down on the grog too, and I now sometimes drink wines instead of my previously preferred Carlton Draught beer. I don’t drink a lot either, because when your bank account has something in it that is worth stealing, you become much more careful about getting into situations where you don’t have full control. My new job is flexible too, and even though I can come home physically tired, I am always mentally refreshed. I tend to go out most Friday and Saturday nights, and now I get much more sex than I did back when I was married, and from a lot more different women too. I might find one to settle down with one day, but as they say ‘once bitten…’

I didn’t pick up that Friday night, but I was looking for a Julie amongst the crowd made up of some real and some temporary Escort Bayan singles at one of the over 28’s nightclubs. I found mutton, but no lamb, and I decided to go home early. I wasn’t nervous about the game, I expected us to lose, but I really hoped it wouldn’t be by too much.

When the ‘roos are playing, and I’m watching at home, I allow myself four beers, one for each quarter, so on Saturday evening I cracked the first one as the siren sounded to start the game. Within thirty seconds our long bomb at goal was touched on the line and we had a point. We were ahead, but then it all fell apart. Collingwood got five goals three (a goal is worth six points) and we got nothing for the rest of the quarter, so the scores were thirty three to a dismal one point at quarter time. I got a text from Julie asking if was watching the game, and I just replied ‘yes’. At least she wasn’t directly gloating. The second quarter was really scrappy, and we got a goal and a couple of points, but they got three goals and two points. The score at half time was to fifty three to nine and my misery wasn’t helped by seeing Julie and her friend in the crowd shots. I swear Julie’s smile was wider than her face. But I didn’t get a text this time.

I cracked my third beer as the ball was bounced and watched a rejuvenated Kangaroos team claw back some ground. They suddenly looked like contenders, but a goal to Collingwood after the siren (the mark was taken before the siren) sent us to the huddle on a bad note. We were still a long way back at seventy seven to forty, but there was a glimmer of hope. I was sorely tempted to turn on the radio to hear the final result, because the TV coverage was on delay, but I wanted to cling to some element of hope for as long as I could.

The start of the fourth quarter was awful. A very doubtful free kick and a fifty metre penalty gave Collingwood the early running, and I thought it was all over when our captain was knocked unconscious in a tackle that had the Collingwood player reported. Sadly the reported player could keep playing and we were down by one on the interchange bench as a result of the clash. Our hopes were raised as an angry team of Kangaroos started tackling like there was no tomorrow, and we got three quick goals, before conceding a point. Eighty three to fifty eight. Fifteen minutes of sensational football later and I was wondering if we had enough time to actually do it, they were ninety five and we were eighty five. Just two straight kicks would put us in front, but we were well into time on already, so the siren could call the end of the match at any time. We got a goal almost immediately, but they replied with another. I was on the edge of my seat as we ran the ball back down the centre and were rewarded with an easy goal from a free kick as one of their back men held on to our full forward. Just one more goal needed.

My voice was hoarse from shouting at the television as we hit the front a minute later with a sensational banana kick from the boundary line. We were ahead one hundred and three to one hundred and one. I was begging the final siren to sound as Collingwood got the break from the bounce, but the Kangaroo defenders looked totally exhausted and I watched in horror as Collingwood ran the ball down the centre and then on of their best players kicked the ball from just inside the fifty. The siren sounded just moments after the kick and the game hung on the ball that was heading toward the goals. It was too high to touch, so our only hope was inaccuracy as it faded to the right. Pandemonium broke out as the goal umpire patted the post, signalling that it had touched. We had won the game by a point.

For a moment I wondered what to do. Should I just forget the bet and continue the job? But that was just for a moment. I knew that I would have insisted that Julie get the discount had it gone the other way, and I really couldn’t let the chance pass. I’d had four beers that evening, but I still felt fine so I went to the workshop in my garage and started up the machinery to print the panels. I knew it would take up most of my Sunday, but it would be well worth it.

I didn’t see Julie on Monday, which was a bit strange. Usually she manages to get home before I’m finished on work days. I did get all of the panels changed over and I grinned as I left. She would be furious, but she had made the bet. Julie’s home is on a corner block. It is a small cream 1960’s brick veneer house, and the pool is beside it rather than behind it, so the privacy screens are essential. From the street I could see two sides of the screen and the Kangaroos colours and logos looked great. I took some pictures for my reference book.

“What will it take to change them back?” Julie asked. She was obviously not happy with the new look.

“I think they look fine as they are,” I replied casually.

“I didn’t think you’d actually do it,” she said indignantly.

“Would you have taken the discount if the ‘Pies Eskort had won?”

“Yeah,” she admitted her eyes down. “Look Darren, I can’t afford to pay you any more, I just don’t have the money,” then she looked up at me earnestly. “What can I do for you to convince you to change them back?” she asked again, and this time she thrust her chest toward me.

“I… uh…” I was lost for words, was she really suggesting a sexual deal?

“I’ve seen you looking at me, how would you like to do more?” she finally asked, making the offer clear.

“It would want to be a lot,” I croaked, my voice letting me down. I wanted her desperately, but this was not the way it should happen. It should be because she wanted to, and this felt too much like blackmail. My attitude toward this sort of situation is to make the stakes way too high, rather than just saying no, because a blunt refusal often escalated the situation and was seen as an insult. So I thought quickly, trying to think of the most outlandish demands possible.

“What?” she demanded, looking at least a bit happier because we were talking about it.

“Four sides means four times,” I said, before I had even thought out my reply properly, “and in four different ways.”

“What ways?”

“One tit fuck with a facial, one blow job and you swallow, one normal fuck to completion and one ass fuck to completion.” Julie looked stunned. “No condoms either,” I added. Julie’s face had drained of colour. That should put the sexual solution out of contention, I thought.

“I’ve never…” she started, “I can’t…”

“No worries,” I reassured her, “I can just leave it as it is.” She shook her head slowly.

“Tomorrow,” she muttered, “I’ll talk to you tomorrow.” Julie turned and went into her house without saying anything else. She looked like she had been punched, and I felt guilty, but at least now she could be the one to refuse the deal, and that would keep her pride intact. I continued working on her paving for another hour, wondering if I had actually pushed her too far, but at least now nobody, including Julie, could see my embarrassing erection, because the screens were all in place. I managed to smile as I looked back when I left. It looked like the Kangaroos screens would stay up for some time.

I got a late night phone call from Finland that night asking me why an Australian customer was asking them if there were any other installers for their product. ‘Well done Julie’, I thought, at least she was looking for every possible answer. I told them that she was just trying to beat down my price to print new screens for her, and that they shouldn’t worry, I had already sold the gear. They sounded doubtful, but accepted that it was my sales territory and I had the right to handle it as I wanted.


But I didn’t sleep well. Half the time I had the most vivid erotic dreams of Julie’s various parts wrapping tightly around my cock, and the other half I was having nightmares about how my rather immature joke could ruin her life. I knew I had to decide which way to go, but the little head was winning the argument as dawn broke. It was telling me to stick to my guns and at least get a good fuck out of it, but after all the dreams my cock and balls felt like they were going to explode so I finally decided I had to take care of myself.

In what was one of the fastest wanks of my life I grabbed the shaft of my cock, replayed one of my erotic dreams in my head and about two and a half strokes later I shot a huge load of cum into the sheet. I never even had time to try and prevent wearing it, and the sheet and I were both soaked. Grinning ruefully, and thanking goodness that I wasn’t still married, I wiped up on a dry part, rolled the soiled bed sheets up and dropped them straight into the washing machine. Then I had a shower, and while the little head was dozing the big head decided that I was going to let Julie off. I would make her keep the Kangaroos covers for a month and then put her Collingwood ones back on. I was tired as I drove to Julie’s place, but I felt a lot less guilty. Deep down I also wished I was a bit less driven by my morals, because Julie was one hot chick, and knocking back a chance to do her was one of the hardest decisions I have ever had to make.

She wasn’t there when I arrived, so I just went to work. Her paving was made up of solid marble tiles, and it was heavy and painstaking work to get them perfectly level and aligned. I was cementing them as I went, which meant frequent mixes, and the day slipped by with me barely noticing. That’s what I like about landscaping, the time passes quickly and you can see a tangible result when you are finished for the day. I was so engrossed that I never heard Julie come home or come out to the pool area.

“Darren,” she said from behind me, startling me, “I’ve been thinking about your suggestion…”

“Me too,” I said, hating myself for what I was about to say.

“No, let me go first,” she insisted, and I turned to her. “There are some things you want that I’ve never done before, and they are things that I am very scared of trying, but you said four parts for four walls, so if we start with one thing we can then see where we go from there. Is that OK?”

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