Harry and the Stupid Bet

For a few seconds after I woke, I didn't know where I was. This wasn't our bedroom, and Anne wasn't next to me. Then I realized that I was in the spare room. Last night I'd come back late. I'd been drunk, but I'd still had the good sense to sleep here so as not to disturb her. But then I remembered that I hadn't needed to. I'd forgotten that she was staying with her Mother. Today was Saturday, and she wouldn't be home until tomorrow evening.

Surprisingly, considering the large quantity of alcohol that I'd consumed when I'd been out with my friends, I was feeling OK. But then I made the mistake of sitting up. My head was now pounding, and it was taking all of my self-control to stop myself from being sick. Then I groaned, and not because I was hung-over, but because of what had happened last night. It was all coming back to me now. Fuelled by the drink and my boastful nature, I'd talked about Liza, my Mother-in-law. I'd told my friends that she was attracted to me, and that if I wanted to, I could have her. And my language hadn't been subtle. I groaned again when I remembered the exact words that I'd used.

"All I'd have to do is put my hands on her big tits, and she'd then be begging me to fuck her."

If Simon hadn't laughed, then that would have been the end of it. But he had, and it had irritated me. Its meaning was obvious to all of us. He didn't believe me. So when he offered me the wager, I readily accepted it, confident that I would win. Now, in the cold light of day, I knew that it was a mistake. And I'd even made it worse later on, when after several more drinks, I'd insisted that we double the bet. Simon had grinned at me, and then he'd quickly accepted. As far as he was concerned, this was a way of making some easy money. And I was now beginning to think that he was right. Last night I'd been confident, but that was because of the alcohol. I have a good relationship with Liza, but she's never given me any indication that she wants it to become in anyway sexual. Now, if I didn't make good on my promise to bed my Mother-in-law, then I would have to pay him four thousand pounds. It would make a sizeable dent in our savings, and because it was Anne who looks after the household accounts, she would definitely notice.

As well as a throbbing headache, and the urge to vomit, I now had a sinking feeling in the pit of my stomach. I was definitely going to lose. I could kick myself. I was twenty five years old, but I'd acted like a teenager who couldn't handle the booze. Anne was only twenty two, but in a lot of ways she was more mature than me. I just wish that I was more like her. If I was, then I would never have made that stupid bet.

By midday I was feeling a lot better, but even though I was hungry I didn't dare eat, because I wasn't sure that I could keep it down. Instead I had some more coffee. As I drank it I thought again about the bet. I still couldn't believe how stupid I'd been. But there must be something that I could do about it. What if I waited for a few days, and then I told him that I'd been successful? He'd believe me, because he trusted me. But I wasn't prepared to sink as low as that. And just thinking about doing that was making me feel ashamed. Then I had another idea. I might be able to get out of it. I could ring Simon, and laugh it off as a joke. I'd have to do some serious grovelling, and I'd certainly lose face with him and my other friends, but it would save me a lot of money.

I got as far as selecting his number, but I was too proud to call him. In two weeks' time I'd have to admit defeat, and pay up. I'd make out that losing was no big deal. I'd tell him that I'd come close, but we hadn't actually fucked, so he was the winner. I'd even smile, and shake his hand, as I gave him the money. And I wouldn't wait for Anne to discover that it was missing, I'd tell her. Of course it would have to be a lie. I'd say that I'd been given a hot tip by one of my friends. It was certain to win, but it hadn't. I'd been unlucky because it was pipped at the post by another horse. I'd then tell her how sorry I was, and that I would never do it again. If I could manage to, I'd even cry. She'd be angry, and for a few days my life would be hell, but eventually she'd forgive me, because that's what married people do, even when the spouse does something stupid.

Anne called me at six o'clock in the evening, to check that I was still coping OK without her. I was, and I was now almost back to normal. I was even contemplating having a beer or two while I watched the football.

The next day she was back home in the evening, just after five, and surprisingly, her Mother was with her. And she was carrying a suitcase. What was going on? Before I could ask, Anne spoke.

"Walt is away on business tomorrow, so Mother has come to stay with us," then, as an afterthought, she added, "I hope you don't mind."

I didn't, but it wouldn't matter if I did, because she was already here, and her large suitcase told me that it was for more than a couple of days.

Later on, while we ate together, I was told more. Walt was a Management Consultant, and he'd been asked, at short notice, by one of his clients to go to their Singapore office. Apparently, it was making a loss, and they needed him there to turn it around.

I asked, "So how long will he be away for?"

"At least for two weeks."

Now that was a coincidence, because the time limit on the bet was also two weeks. And considering how boastful I'd been, telling Simon how easy it would be, his suggestion of that duration had been generous. That got me thinking. I worked from home and my Mother-in-law was a lady of leisure. Walt, her partner for the last eight years, was wealthy, so she didn't need a job. During the day, while Anne was out, we would be spending a lot of time together. The perfect opportunity for something to happen between us. After giving it more thought, I made a decision. And now that I had, it was taking all of my self-control not to smile.

I was going to win the bet!

We'd been apart for a week, so both of us were eager to go to bed early. However, we had to stay up later than we wanted to, because Liza was here with us. It was almost ten o'clock before we got to our bedroom.

As soon as the door was closed, we were kissing, and my hands were on her tits. This was going to be a quick fuck. While she'd been away, I'd kept my hands off my cock, so my balls were full. And now I desperately wanted to empty them into her sweet pussy. And it was what she wanted as well, because before my fingers had even found her nipples, she stepped back, so that she could take her panties off.

She was now on all fours, and I was behind her, cock in hand, ready to position it at her opening. But first, I took the opportunity to admire the view. This was a pussy that never failed to excite me. I loved her large lips, they were a nice mouthful. And hidden under all those folds was a clit that was a nice size.

When I entered her, it was with a force and speed that took her breath away. And I didn't give her any time to recover. She was now being fucked hard, and I was using every bit of my big cock. On every stroke she was getting all of my eight inches.

"Fuck, I love your big cock. Make me come."

When I upped the pace, her moaning became louder, and I was now grunting. We'd become rutting animals.

The stroke that made her come was brutal, but it needed two more of the same before I reached it. Mine was a long satisfying one, and hers was equally impressive. When I'd finished spurting, she was coming down from her high. It hadn't taken us long, but it was what both of us had needed. After pulling out of her we cuddled, but only briefly. Within minutes we were both sound asleep.

I thought that I was the first one up, but I was wrong. Liza was already in the kitchen, and she was making breakfast.

"Coffee's made, help yourself."

After thanking her, I did.

"One egg or two?"

"Two please."

When it was ready she served me, and that's when I realized that she wasn't going to eat. She must have seen the surprise on my face, because I got an explanation for why she wasn't joining me.

"I've already had my breakfast. Just some toast. I need to watch my weight."

If it wasn't for the bet I wouldn't have said anything. But if I was eventually going to get to fuck her, I had to start somewhere. And now, because she had given me the opportunity to flatter her, this was the perfect time to start.

With a cheeky grin, I said, "You don't need to. You look OK to me."

"Don't be silly."

But her smile told me that she'd enjoyed the compliment. If I was careful, I could say more.

"I mean it. Walt is a lucky man."

To my surprise, and probably hers as well, she blushed.

After quickly putting her hands onto her cheeks, she said, "It's hot in here."

It wasn't, but I let it pass. I'd boasted to my friends that all I had to do was grab her tits and she would be mine, but that was never going to work. I'd said enough for now. I needed to play the long game.

Two days' later, I complimented her on the dress that she was wearing. It was an easy thing to do, because it was stylish and it fitted her well, showing off all her curves. This time she didn't blush. And the radiant smile that she gave me in response, made my heart skip a beat. It felt as if I was making progress.

The next day I was up early. As soon as I'd finished eating breakfast I went to my study. The article I was working on had to be completed by the end of the day. It was for our local newspaper. Three hours later I'd completed more than half of it, and I was pleased with myself. It was time to take a break. When Liza entered the room, I was leaning back in my chair, with my feet on the desk, and my hands behind my head.

"So is this what you do all day, hide in here pretending to work?"

"Yes."

She laughed, and I joined in. I then took my feet off the desk, and she handed me the coffee.

"Thanks," then after taking a sip of it, I declared, "Perfect. Just like you."

"Stop it. I'm not used to receiving compliments."

She'd said stop, but I got the impression that if I continued she would like it.

"Why don't you make yourself a drink and then come back. We can spend some time together."

"I will, that would be nice."

While she was gone, my imagination ran wild. I was working out the best position for fucking her. It was an easy decision. It would have to be with her bent over the desk and me behind her, pounding her pussy. But that was wishful thinking. We were only at the stage of mild flirting. There was still a long way to go!

We spent almost an hour together, and I really enjoyed it. The conversation was interesting, and at times, even funny. And while we talked, I realized something. My pursuit of her had started because I wanted to win that stupid bet, but now I was motivated as much by lust, as I was for the money. My Mother-in-law was an attractive woman, and I would definitely enjoy fucking her.

She's forty three, but she doesn't look it. Being well off has enabled her to pamper herself. Her hair and nails are always immaculate, and she never wears anything that isn't tailored or stylish. Elegant, is a good word to describe her. But if she was to remove those expensive clothes for me, so that I could gaze on her naked body, would I be disappointed? No way! Her breasts are a nice size, not ridiculously large, but big enough for me to get a lot of pleasure from. And after seeing her lots of times in a bikini, I know that her nipples are impressive. They might even be her best feature, but I'd want a good look at her pussy before making that judgement.

So is she perfect? No, twenty years ago she might have been, but she has aged well. She has a few extra pounds around her waist and on her bottom, but I don't mind that because I like my women curvy.

That evening I got a call, and it was one that I had been expecting. The only surprise was that he hadn't called earlier. It was Simon, and I knew that he was going to taunt me.

"Hi Harry, have you managed to have your wicked way with your Mother-in-law, or did you crash and burn?"

Then he laughed. I could feel my blood pressure going up. I needed to stay calm.

Through gritted teeth, I gave him a curt, "No."

"I didn't think so. You do know that you're going to lose?"

In as calm a voice as I could manage, I said, "There's still plenty of time left. When I win it will be me that is laughing."

"You sound confident. Would you like to increase the stake to five thousand pounds?"

When the call was ended, I put my head in my hands. I'd taken stupidity to a new level. Perhaps even a world record. I hadn't just agreed to five thousand, I'd insisted on it being six, and Simon had quickly accepted it. And why wouldn't he? The odds were in his favour. I was in a hole, and I'd foolishly kept digging, because I had let him get under my skin. I should have kept my cool, and said no to increasing the bet. I was now going to have to win, if I didn't, then Anne was going to kill me, and she would make sure that it was a slow painful death!

That night I had a dreamless sleep, and I woke refreshed. It felt good to be alive, and then, when I remembered my conversation with Simon, my mood changed, and not in a good way. I swore under my breath.

While I showered, I thought about Liza. If there was any chance of success, then I needed to up my game. Words would have to be replaced by action. I needed some excuse to touch her body. Somewhere that wouldn't make her feel uncomfortable. Then, if I was careful, I might be able to make it more intimate.

At ten o'clock, when she brought me a coffee, I noticed her newly painted nails. This was an opportunity too good to ignore.

"I like the colour of your nails."

Before she could respond, I reached out so that I could hold her hand. She looked concerned, but when she saw me taking a closer look at her nails, she relaxed.

Smiling, she said, "Midnight Blue."

Was that really a colour? As nice as her nails were, that wasn't why I was holding her hand. And if I was going to get some success, then I needed to keep the conversation going.

"Have you done your toenails as well?"

"Yes, would you like to see them?"

I nodded. She then took her sandal off. Like her fingernails, they were the same colour, but a lighter shade. Before I could ask, she told me.

"Subtle Blue."

I muttered under my breath, "Another silly name," and then I shook my head. She giggled. It was nice to hear, and it made my heart beat faster.

"But you missed a bit."

She looked concerned. My Mother-in-law was a perfectionist. When she did something it had to be done properly.

"Where?"

She had, the edge of her little toe, but rather than just tell her, I knelt down, then I cradled her foot. I pointed it out to her.

After shaking her head, as if she couldn't believe it, she said, "And I thought I'd done it perfectly."

"Next time, you should let me do it for you. I'll make sure that I do a good job."

It was unlikely that she would say yes, but it was worth a try.

However, while smiling, she said, "I might take you up on that, but it would have to be our little secret."

I was hoping for a yes, but her answer was full of promise. Her not wanting Anne to know about it, told me that she regarded it as an intimate act. And it was something that she was considering letting me do.

Because of her encouraging words, I was feeling bold. Now I wasn't just holding her foot, I was gently massaging it.

"That's nice."

"Sit on the chair and I'll do your other foot as well."

She hesitated, but only briefly, and then she said, "OK."

Before she sat down I moved the chair away from the desk, to give us more room.

Initially, my hands were just on her feet, but now I was slowly moving them up, and she was letting me do that. That was a good sign. When I got to her calves I stopped, but when I looked up at her face, and I saw that her eyes were closed, I decided to continue. When I got to her knees my touch was gentler. Now I wasn't massaging her, I was caressing her. She must have noticed the change, but she still wasn't complaining.

To go higher, I would have to part her legs, and then go under her skirt. It was what I wanted to do, and my stiff cock was in agreement with me, but was it what she wanted? It must be. She wasn't a shy young virgin who didn't know about men, she was a mature woman. She was experienced. When my hands had moved away from her feet, she would have known where they were heading. Towards her pussy. And she hadn't stopped me. That would have been easy for her to do, with a few words, or a simple gesture, and it could be done without it being embarrassing for either of us.

Before moving her skirt up, I checked that she still had her eyes closed. They were. When it was out of the way, I put my hands on her thighs, and then I pushed against them. There was no resistance from her.

When I saw it I had to smile. Close to my face was her most sacred place, and covering it were white panties that were at least a size too small. They were stretched so tight that I could see all her contours. Just looking at her covered pussy was making my mouth water and my cock throb. I wanted to quickly pull her panties to one side, and then thrust my fingers deep into her, but I had the good sense to hold back, because that might startle her. It was better to take my time, to move my hands slowly up her thighs. But would I have the self-control to be able to do that? I hoped so.

As my hands moved higher, one on each leg, I could feel my heart pounding in my chest. It had been a long time since I'd been as excited as this. When I got to the edge of her panties I stopped, and then, with the lightest of touch, I ran a single finger along her opening. It made her gasp. It was barely audible, but it was confirmation that she was excited, and that she wanted me to continue. When I did it again, my touch was firmer, and this time I got a loud moan from her. And it was something that I'd heard countless times before, because it was identical to the sound that her Daughter makes when I'm exciting her. It was now time to go inside her panties. And if she was to let me do that, then we would end up fucking, and I would win the bet.

When I heard it, it made me jump, even though it wasn't very loud. And it must have startled Liza as well, because her eyes were now wide open, and she was quickly closing her legs. My hand was now trapped, and I had to pull hard to get it out. I then stood up. As I answered my phone, she was straightening her skirt. That gesture said it all. We had finished. To say that I was disappointed, was the understatement of the year.

"It's Anne, she wants to speak to you."

When I'd said her Daughter's name, her face changed, and the expression was easy to read. It was guilt, because she had almost betrayed Anne. When I handed the phone to her she averted her eyes, and that made me realize that this wasn't going to happen again. I was bitterly disappointed. If only Anne hadn't called, we'd have fucked.

Their conversation didn't last long, and as soon as it had finished she left my study without saying another word. I had a pile of work to do, but I wasn't in the mood to do anything. I just wanted to sulk. And I was good at that.

Until we ate our evening meal together, we didn't see each other again. There was no mid-afternoon coffee and biscuits from Liza. And that told me a lot. Would our relationship ever get back to normal? Probably, but there would be no more shared intimacy.

At first, I felt tense, and from Liza's body language, it was the same for her as well. But by the time we'd finished eating both of us were more relaxed, and at one point she'd even laughed at my silly joke.