Brother and Sister Make a Bet

"What are you reading?"

"Nothing that you'd be interested in."

"I might be. Let me see it."

I shook my head. Then, with a quickness that took me by surprise, she snatched the phone from my hand. I could easily get it back, but it was already too late.

While smiling, she said, "So my little Brother likes to read naughty stories."

That was true, so I wasn't going to argue with her.

"And I thought that you were a good boy."

Then she read some more.

"VERY naughty stories."

Now she was sniggering, and I was embarrassed. It was time to defend myself, because as far as I was concerned, I hadn't done anything wrong.

"There's nothing that's underage. And I'm twenty, that's old enough for me to read them."

That made her smile, and I knew why. She was twenty six, so as far as she was concerned, I was still a child.

"What's the story called?"

That was rhetorical. I knew that she was going to get great pleasure from telling me what the title of it was.

"Adam and his Mother."

She was enjoying making me squirm. And she wasn't going to stop.

"While at a fancy dress party she mistakes him for her husband, so they fuck."

That was the short description of it, and it summed it up in a nutshell.

"That's ridiculous, it could never happen. She would know that it wasn't her husband, even before they started having sex."

"I disagree. You haven't read all of the story. It's well-written, and it's convincing."

That got a snort of derision from her. Then, after throwing me my very expensive phone, that I only just managed to catch, she left the room.

I wasn't worried that she would tell our parents what I had been reading. My Sister was many things, but a tell-tale wasn't one of them. Even from an early age, any secrets we had, always remained between us.

I thought that was the end of it, but two months later Alice wanted to talk about it again.

While we were alone, and without any preamble, she suddenly surprised me with, "Do you remember when I caught you reading that story?"

I did, but why bring it up again now after such a long time?

"Yes."

"Do you think that it could happen for real?"

I gave it some thought, and then I answered her.

"Given the right circumstances, yes I do."

"Good, now how about putting your money where your mouth is?"

That's when we made the bet!

We didn't wager much. It was more about being right rather than the money. The winner would be able to brag about it for a long time.

That evening, while I was alone in my room, I thought some more about what I had readily agreed to.

At the weekend there was a fancy dress party, with a stipulation that a mask must be worn. I wasn't invited to it, but my parents were. Alice was confident that she could persuade Father to let me take his place.

"I'll tell him that we are playing a joke on Mother. I'm sure that he'll agree to it."

For me to win the bet, I had to get to midnight without being found out. Then I would take my mask off and surprise her.

On the morning of the party we all had breakfast together.

"I'm really looking forward to tonight, it's been ages since we've been out."

That was from Father. He was playing his part well, because he sounded excited, even though he was really staying at home.

Looking at Mother, I asked, "What time are you leaving?"

"Eight. It will take us twenty minutes to get there."

I was hoping it would be later because that would increase my chances of winning the bet.

"Isn't that early?"

She just shook her head. I left it at that. If I was to push it then she'd get suspicious.

After eating I went to my room. It wasn't long before my Sister joined me.

"Nice try, but it didn't work. If you want we can call it off. It's going to be embarrassing when you are discovered after only ten minutes, or will it be five?"

That amused her, but it irritated me, and that's why I suggested we increase the bet. Now it was serious. The money had been replaced by something more important, our time. The loser had to do the others bidding for a week.

Until it was time to get ready for the party, I kept myself busy. Doing nothing would have given me time to think about it, and that might have made me nervous. To win, I had to stay confident. I was going to be an actor playing a part, and I needed to be convincing.

It was now time for the switch. I was in my bedroom, constantly looking at my watch, while I waited for Father to join me. And my confidence was slowly ebbing away. When he eventually opened the door, I was about to call it off, but Alice was with him, and the first words out of her mouth told me that it was too late to change my mind.

While smirking, she said, "I've already got a list of jobs for you to do. Would you like to see it?"

I just ignored her. If I was to get into a conversation with her, it might quickly become an argument. Now wasn't the time for that.

Thankfully, when I was wearing the costume, most of my confidence returned. We were the same height, and almost the same build, so it was a good fit. The mask was full faced, only my eyes and mouth were exposed. There was a good chance that I'd be able to fool my Mother.

When I looked in the mirror I smiled. I was now Homer Simpson!

My strategy for winning was simple. To say as little as possible to my Mother, and to spend as much time as I could away from her. My voice and Father's were very similar, but not identical, so talking too much might give me away. The most difficult time was going to be while we were in the car, because we would be close together.

When I went to their bedroom she was still getting ready. She was just in her underwear. To give her some privacy, I was about to turn my back towards her, but I stopped. That would have been a mistake because my Father wouldn't have done that.

While giving me a nice smile, she said, "Two minutes and I'll be ready."

That was enough time for me to admire her body, and I took the opportunity to do that, starting at her top, and then working my way down.

Her breasts were covered by a bra that looked to be too small for her, so there was a lot of cleavage on display. They were nice tits, something to be proud of. And as for her panties, that were covering her most sacred place, they could only be described as skimpy. I didn't look at them for long, because to do so would have got me excited, and that would have been wrong.

My Father was a good-looking man, but even so, he was definitely punching above his weight. He'd managed to marry somebody who should have been out of his league. It was a given that she was beautiful, and she had the body to go with it. Her breasts were large, but not excessive. As were her hips. And to complete the picture of near perfection, she has a narrow waist, and a bottom that men can't take their eyes off.

She was forty five years old, but most men, even those a lot younger than her, would still want her in their bed!

When we got into the car my heart started to race. I was convinced that any second now, I would be found out, and that would make my Sister's day. However, she was content to stay silent, so eventually I calmed down. She didn't speak until we were almost there.

"Take a left here, and then a right when you get to the end of the road."

When I saw the house I had to smile. I say house, but it was more like a mansion. In it there would be plenty of places for me to hide. I should start to compile my own list of jobs, because I was now confident that I was going to win the bet.

I'd just parked the car when she did something that startled me. She put her hand on my leg, high up on my thigh. I gulped. Was it going to move onto my cock, and if it did, then what was I going to do?

"I'm going to enjoy this. I'll have a few drinks. That will put me in the mood for sex when we get home."

That was something that I didn't want to hear, and worryingly, I had no idea how my Father would have responded to it, but I needed to say something.

"That will be nice."

After briefly laughing, she said, "It needs to be better than nice."

When we got inside, and we were greeted by the host, I was relieved. So far so good. Just a few more hours and I'd be the winner.

"Darling, get me a drink, and make it a large one."

I did, and I made it strong. If I could get her tipsy then she would be less likely to realise that I was really her Son.

Later, after making her a second drink, I managed to slip away while she was talking to one of the other guests. And I found a good hiding place. One of the small bedrooms on the third floor. I was planning to stay for thirty minutes, but when it got to twenty, I changed my mind. I should go back to her. I was almost at the door when it was suddenly flung open. I nearly jumped out of my skin.

"There you are. I've been looking everywhere for you."

Then her arms were tightly around me. Her words had been slightly slurred and I could smell the alcohol on her breath. I was a fool, I should have stayed with her so that I could have watched what she was drinking. She must have had some more while I was away from her.

She wasn't just tipsy, she was drunk!

Her holding me wasn't a problem, neither was her trying to squeeze the life out of me, but trying to kiss me on the mouth, was. She was my Mother, so that was wrong.

"What's a matter, don't you love me?"

I did, but not in the way that she meant. However, I was going to have to let her kiss me before she got suspicious, but it would have to be brief.

Homer and Marge were now kissing, but it was difficult because of the masks. Then she suddenly found a way of making it better, by sticking her tongue into my mouth. I should have resisted, and I wanted to, but I couldn't help myself. I was greedily sucking on it. Then it was her turn, and now my tongue was in her mouth.

She was my Mother, but my cock had forgotten that. It had reacted as if she was my lover. There was now a lot of blood in it. And it wasn't just hard, it was poking into her. We needed to stop before she noticed. But it was too late.

"Is that a gun in your pocket, or are you happy to see me?"

Then she giggled. I tried to push her away, but she was surprisingly strong. And she was eager to do more than just kiss. I gasped when her hand was suddenly on my cock. And now she was squeezing it through my trousers. What was I going to do? It wasn't even ten o'clock. To win the bet I was supposed to get to midnight without my secret identity being revealed. What was happening was embarrassing, but it was going to get worse if I didn't end it now. She was going to be surprised, and then angry, when I took my mask off. However, I was going to have to take it on the chin. Hopefully, after some time, she might even find it funny.

"Would you like to play with my big tits? Of course you do."

Before I could say no, she'd grabbed my hand, and then she placed it on her right breast. Despite knowing that it was wrong, the urge to keep it there was too much for me. Homer was now groping Marge's impressive tit.

As I moved my hand over her breast, and she continued to move her hand over my manhood, I told myself that I was going to stop. Just a few more seconds and I would. And now, because of what we were doing, I'd realized that there was no way that she could ever know who I really was. I was going to have to tell her that I was feeling sick, and so we would have to go home. All thoughts of winning the bet had gone, it was now about damage limitation.

But when those few seconds became a minute, and then two, I knew that I'd lost control. It was as if my hands had a mind of their own. When I started to unbutton her top, I stopped thinking of her as my Mother. She was now just a desirable woman. A woman that I wanted to have.

I wasn't able to stop, but surprisingly, she could, because she was going towards the door. I had mixed emotions, relief and disappointment. And disappointment was the stronger of the two. However, it was probably for the best. We'd already done more than a Mother and Son should ever do together.

But when she got to it, she stopped.

"I'm locking it. I don't want somebody coming in when my tits are hanging out, or worse, when my pussy is on display."

As soon as she was back with me, my hand was quickly going inside her top, and then under her bra. I was desperate to get to her nipple.

"Somebody is eager, but it will be better if you take my clothes off."

It was good advice, and I took it. Having to wait while I slowly removed her top, and then her bra, heightened the experience. She was now topless, and there were butterflies in my stomach, in anticipation of what was going to happen next.

Over the years, I've seen her in just a swimsuit, lots of times. With some of the more revealing ones, I've even been able to see the outline of her nipples, so I already knew that they were big. But now that she was naked from the waist up, so that they weren't being squashed, I was still surprised by how big they actually were. I couldn't take my eyes off them.

"Why are you staring at them? It's as if you've never seen me topless before."

That was careless of me. She was drunk, but not so drunk that she wasn't observant. I needed to be careful.

After shrugging my shoulders, in the way that my Father often did, I said, "I was just reminding myself of how beautiful they are."

That made her smile, and she was still smiling when my hands got to her tits.

I should be feeling guilty for taking advantage of her, but I wasn't. While my fingers explored every part of her large mounds, before concentrating on her plump nipples, my only emotion was pleasure. I was driven on by lust, and the need to be sexually satisfied. In the back of my mind I knew that this was probably not going to end well, that eventually she would discover who I was. However, that was a problem for later, now was all about enjoying myself.

And it wasn't just me that was getting pleasure from what I was doing, she was as well. I was rolling one of her nipples between a finger and thumb, and it was making her moan. The other one was being stretched, and when that happened, she would gasp.

"Suck them."

She didn't need to ask me twice.

"It will be better if you take that silly mask off."

Yes it would, but that could never happen. When she realised that I wasn't going to remove it, she tried to pull it off. I had to restrain her by holding her hands. She struggled to get free, but when I started to eagerly suck on one of her ripe nipples, she stopped resisting. When I let go of her hands she cradled my head with them. I was her baby, suckling on her breast!

It had been good before, but now it was even better. After having my fill of one nipple, I switched to the other. I kept on doing that, and all the time that my mouth was on her, her hands were on my head.

"It's time to finger me."

Those were just words, but hearing her say them sent a surge of excitement through my body.

Her skirt was long, so I had to pull it up so that I could put my hand between her legs. That wasn't a problem, but she, at the same time, unzipping my trousers, was. Of course I wanted her hand on my cock, but what if I was bigger than my Father, or even worse, smaller than him? I knew that eventually it was going to have to come out, but I would have liked to delay it for as long as possible.

When I got to her panties, her hand was in my underwear. As she roughly yanked my cock out, my fingers were rubbing her pussy through the thin material that was covering it. Then she started to eagerly stroke my manhood. I offered up a silent prayer to any deity that was listening. Please let me be the same size as my Father!

I was tense, but as the seconds passed, and she hadn't freaked out, I relaxed. I could now enjoy her pussy while she was pleasuring my cock.

When I'd reached the limit of what I could do to her pussy with her panties on, I took them off. I didn't ask her, I just did it, and as quickly as I could.

If I could freeze time, so that it would last forever, then this was as good a time as any. She was lying on the bed with her legs wide open, and I had two fingers deep up her hot wet pussy. And while I was fucking her with them, she was stroking my cock, with just the right amount of pressure, and at the right speed.

When, between moans, she suddenly said, "You're not doing it," I was worried. I had no idea what I should be doing, and she would find it strange if I was to ask her what it was. However, I needed to stay calm, panicking wouldn't help. I was supposed to be smart, the clever one in the family, perhaps I could work it out.

"Don't spoil it, I'm still waiting."

Unless my Mother had some fetish, like having her toes sucked, then logically, there was only one thing that was the prime candidate. I was going to try it, and hope for the best.

"Yes, that's perfect!"

Thankfully, I was right. She'd wanted me to rub her clit.

She was now coming to the boil, and that was understandable. Fingering her was keeping her excited, but it was the attention that her little pebble was getting, that was going to make her reach it. But what about me? Her hand was still stroking my cock, and I was enjoying it, but it would need a lot more effort from her if she was going to make me come. But I didn't mind. I wanted to empty my balls, but I was happy to wait until my cock was deep up her sweet pussy.

When I heard it I almost jumped out of my skin. Somebody had suddenly knocked on the door.

"Open up, we want to come in."

I had no idea who they were, but them joining us was never going to happen. And I was going to tell them that.

"Please go away."

There was another knock, and this time even louder than before. I'd been polite, and it hadn't worked. It was time to be assertive.

As loud as I could, I shouted out, "Fuck off, and don't come back."

That worked. There was some muttering from the other side of the door, but after that, there was silence.

"James, I've been waiting more than twenty years for you to say fuck."

Then she laughed.

I used it all the time, but my Father never did. That was another slip-up that I'd got away with!

That interruption could have spoiled the mood, perhaps even ended our intimate time together, but thankfully it didn't. Within seconds we were back to where we were before.

She was now almost there. I was frantically rubbing her clit so that she would come. It had become all about her needs. My cock was still rock-hard, but her hand wasn't on it.

When she did eventually climax, it was with a bang rather than a whimper, because it was intense and it lasted a long time. And when it ended, she just lay there with her eyes closed, as if she was sleeping, for at least a couple of minutes.

While I was waiting for her to recover, I was looking at her and smiling. Then, when her eyes opened, my smile got even bigger, because very soon we would be fucking!

"Put your cock deep up my little pussy."

Good, she was as eager as I was to start.

The head of my cock was now at her opening. It was a time for second thoughts, to think about the consequences of what I was about to do. A time for feeling guilty because, I, her Son, was about to fuck her without her realizing who I really was.

But none of those thoughts were mine. All I was thinking about was her pussy, and how good it would feel when my cock was deep up it!

As I pushed into her, she purred, and when I was fully in, she gasped. I didn't make a sound, but I was grinning like an idiot. This was as good as I'd hoped it would be. Her pussy was hot and wet, and it was gloriously tight. It was everything that you want a pussy to be.

"Fuck me."

I did, and the first stroke was gentle. The next one was the same.

"What are you doing? You know I don't like that."