Two Friends Make a Bet Ch. 02

The story continues, but Jacob is now the narrator!

--

"If you hadn't ended it, who do you think would have won?"

I looked at Alex, and like me, I could tell that he was reluctant to answer Ryan. Trying to have sex with my Mother had been a dismal failure, and it must have been the same for him with his.

"I think it would have been Jacob."

I was pleased that Ryan had picked me, but I didn't share his confidence. And I could see that Alex wasn't happy.

"Why do you say that?"

There was irritation in his voice.

"Because your Mother is a lady."

That calmed him down, but it raised my blood pressure. Yes, Alex's Mother was indeed a lady, but the implication of what Ryan had just said, was that mine wasn't. I stormed off, slamming the door on my way out.

Five minutes later, Ryan called me.

"Sorry. I should have kept my big mouth shut."

I sighed, and then I said, "And I guess I should have stayed."

"My Mother says you owe her for a new door."

Then he laughed, and I joined in. We then ended the call, and I headed back to Ryan's place.

That evening, while I was in my room, I thought about the bet. When I had made it, I was confident that I would win. She would give in without much resistance, but I hadn't liked Ryan implying that. She might not be a lady, but she was a good Mother.

The next day, I went to see Alex.

"You never said, but how far did you get?"

"What do you mean?"

"With your Mother. I guess it was the same as me, a big fat zero."

"Yes."

My question had taken him by surprise, and for a brief moment, before he had answered, he had looked worried, as if he was hiding something.

"Was it her tits?"

"I told you, we didn't do anything."

I could tell that I had hit a nerve, but badgering him wouldn't make him talk. However, a softer approach might.

"How long have we known each other?"

"Forever."

It did feel like that. We started school together, and within days we were best friends. Since then, we had told each other all our secrets. I was now waiting for him to tell me about his Mother.

Fifteen minutes later, he had finished. I couldn't believe it. For most of the time, I was either shaking my head in disbelief, or staring at him, open-mouthed.

"And that's all of it."

I muttered, "You lucky bastard."

That got a wry smile from him.

"You did all the things to her, that I wanted to do to my Mother," then I sighed, before adding, "But all I got from her was a fat lip."

When I left, his Mother was in the kitchen. I was thankful for that. I would have found it difficult looking at her, without imagining her being fucked by her Son. And worse, she might realise what I was thinking.

That evening, while I ate with Mother, I kept thinking about what Alex had told me. I was still finding it hard to believe. He hadn't just had her tits or pussy. He had fucked her, and he was still doing it. I was deeply envious.

At eight, Mother went out.

"I'm not going to be back until late."

"OK, but don't get drunk."

"Yes dear," then she laughed.

At times, we were like an old married couple. But without the sex.

My Father had died when I was fourteen. Hit and run. The driver was never caught. I would like to believe that it had been a Mafia hit, but it was just a tragic accident. Since then, it's been the two of us, apart from Mother's occasional boyfriends. The last one was nearly four months ago, so she must be ready for another one. When she finds him, he will be the love of her life. But it won't last!

I was woken up by Mother. I looked at my phone, and then I groaned. Five minutes past one. Coming in late wasn't a problem, but why did she always have to sing when she was drunk? I burrowed my head into the pillow, waiting for her to stop. Eventually she did, but I was now wide awake. Why couldn't she be more like Alex's Mother?

They were like chalk and cheese. His was always demure. Well dressed and polite. And she never flirted with me, or his other friends. Mine was loud, often saying inappropriate things. And some of her clothes left little to the imagination. They might have different personalities, but physically they were very similar. Both of them having bodies that attract men. However, Alex's Mother did her best to hide hers, while my Mother's was always on show. If you were to bet on which one of them would end up having sex with their Son, it would be mine. But you would lose!

On Tuesday, I went to the park with Alex and Ryan. I was itching to ask Alex something, but I wanted to wait until we were alone. When Ryan left us, I was hesitant, but I decided it was best to just jump in.

"Will you help me with my Mother?"

"What do you mean?"

Thinking about it had been easy, but having to say it, was more difficult than I thought it would be. I took a deep breath, and then I blurted it out.

"I want to sleep with her."

"That's easy. You just get into bed with her, and then you close your eyes."

"That's not what I meant. I want..."

I stopped, because he was grinning. Then I waited, hoping that he would now give me a sensible answer. He took his time thinking about it, before he spoke.

"It will be difficult. What you mustn't do is just go for it. You have to take it nice and slow. Don't just grab her tits."

I winced. I had tried that, and it had got me a slap across my face.

"The problem with you Jacob, is that you are too good looking. You don't have to work hard to get a woman. But this time it's different. You are going to need more than just your pretty face if you want to fuck her."

He had made it sound as if all I had going for me, was my appearance. However, he did have a point. I was vain enough to know that I was handsome. And most of the time, that was enough to get me what I wanted.

"OK, but what do you suggest?"

"Where is she now?"

"At home. Probably in the garden sunbathing."

It was hot, and she did like to maintain her tan. And, if she was doing that, then I would bet big money, that she was wearing a very small bikini.

"Why don't you join her? You can offer to put sun cream on her. That will give you the opportunity to touch her body."

Just thinking about it, was getting me hard.

"But remember. This is a slow process. Don't expect it to end with her on her back, with you on top of her."

Half an hour later, I was making my way home.

As soon as I opened the door, I heard Mother calling me.

"I'm in the kitchen. Do you want anything to eat?"

I shouted back, "No."

When I saw her, my heart sank. She was fully clothed. I sat down at the table. What should I do now? Or better still, what would Alex do? That was easy, he would persuade her to go into the garden.

"I thought you would be outside, enjoying the good weather."

"That would be nice, but I have things to do."

"Tomorrow it's going to rain."

"I didn't know that."

Neither did I. I had made it up, hoping that it would convince her to sunbathe. I could tell that she was thinking about it, but I needed to say more. Something that would tip the balance.

"If you go into the garden, I'll come with you."

It had worked. I was now outside, waiting for her to join me. When she did, I would casually ask if she wanted me to apply the sun cream. But why was she taking so long? Then I groaned, she must be doing it now, while she was getting changed. When she did eventually appear, I had convinced myself that it wasn't going to work.

"It took me ages to decide what to wear. What do you think?"

Her hands were now on her hips, and she was looking at me. Waiting for my verdict on the bikini. It was a new one. I was certain of that, because I would have remembered it. On a woman in her twenties, it would have been daring. On her, at forty three, it was outrageous. I loved it, but it wasn't something you wear in front of your Son. But what should I say? I wanted to tell her that her breasts looked magnificent in it, and that her bottom was a thing of beauty. Then I remembered Alex's warning, about not rushing in.

"I like it. It looks good on you."

That got a nice smile from her, and then she said, "Do you think it's too revealing?"

That gave me the opportunity to look at her again. The top was small, only just covering her nipples. And it was straining to keep her breasts in. The bottom part was covering her, but only just. Yes, it was too revealing. And my cock, that was now struggling to get out, was agreeing with me.

"It does show your body off. But you know what they say?"

"No, tell me."

"If you've got it, then flaunt it. And you have definitely got it."

"Don't be silly."

She was dismissing my compliment, but I could tell that she had liked what I had said. She then sat on the recliner, adjusting it so that it was flat. I was to the side of her, sitting on a chair.

I waited ten minutes before making my move.

"It's very hot. Have you got enough sun cream on?"

"Yes."

"Are you sure? I don't want you to get burnt."

"You're right. I'll put some more on. It's better to be safe than sorry."

"Would you like me to do it?"

I held my breath. Was I going to get a yes, or another slap? She was thinking about it, so that was a good sign. Then she smiled.

"My back does need some cream on. And I can't do it myself."

She was now face down, and I had my hands on her. I started on her shoulders, and then I did her back. When I had finished there, I moved onto her legs. I was expecting her to ask me to stop, but she didn't, so I continued.

My hands were now high up, inches away from her bottom. I kept staring at it, desperate to squeeze it. My cock was throbbing, and I was starting to lose control.

"I'm going to get up."

I mumbled, "OK," and then I removed my hands.

She was now sitting up. I would have liked it to continue for longer, but if it had, I would probably have ruined it, by doing something rash.

"You did a good job. Would you like to do my front?"

I was about to say yes, but I stopped, mouth half open. She must be teasing me. I scrutinised her face. There was no hint of a smile. To my amazement, I realised that she was being serious. I was now so excited, that if I was to speak, she might hear it in my voice, so I just nodded. She then lay down on her back.

I started on her face.

"Close your eyes."

She did, and she kept them closed when I moved down to her shoulders. That gave me the opportunity to look at her breasts. When I was a teenager, I had found it difficult not to stare at them. To admire their shape and size. I had often masturbated while thinking about them. And now, I had my hands on her, only inches away from them.

"That's nice, but you need to do the rest of me."

I mumbled, "OK,"

As my hands moved lower, my cock started to grow. When I got to the outline of her bikini, it was ready to burst. I was actually touching her tits, massaging the cream into them. And she was enjoying it. Her response was subtle. An occasional low moan, or a slight movement. I might only be twenty two, but I knew the signs. If she was my girlfriend, then my next move would be to push her top down, and go for her nipples. But she wasn't, she was my Mother. So I needed to proceed with caution.

I was now doing her stomach, but sometimes going higher, pushing her tits up.

"I think you should do my legs."

I looked up at her face. Her eyes flickered for a moment, but they remained closed. I had thought that what I had been doing, was exciting her, but now I wasn't so sure. Her face was expressionless, and she had asked me to move away from her tits. Was I reading it wrong?

My hands were now on her feet. There was still blood in my cock, but not as much as before. It would soon be limp.

Then I applied cream to her calves. I was now concentrating on just protecting her from the sun. I had no expectation of it turning into anything else.

Then I almost dropped the bottle.

When my hand had touched her knee, she had opened her legs. And she had opened them wide. A lot more than was necessary for me to put sun cream on them.

I was now staring at her plump pussy. The thin material of her bikini was stretched across it, showing off all her contours. I could see the outline of her lips, and the bulge that was her clit. But my eyes were drawn to her opening. It was easy to find, because of the large damp spot. So she was excited, and a lot more that I had realised.

My hands were quickly on her thighs. But what should I do? She was inviting me to finger her. Or was she? I was confused, but my cock wasn't. It was urging me to go for it.

The first touch was gentle, just the tip of my finger brushing over her pussy. It got no reaction. That surprised me, because she must have felt it. I did it again, but this time harder. That got the response that I was hoping for. She moaned, and to confirm that it was what she had wanted, she also moved her bottom so that her pussy pushed against it.

I was now grinning like the Cheshire Cat. I was rubbing her clit, but I wanted to take her bikini bottom off, and push my fingers into her wet cunt. But I held back. Alex's voice was in my head, telling me not to spoil it. To stick with what I had. That made sense. If I was to make her climax, then surely there would be a next time. And then we would do more, perhaps even fuck.

As I serviced her clit, she was starting to make more noise. She was well on the way to climaxing. I rubbed harder, and that moved her on even more. It wasn't going to be long before she boiled over.

A minute later, she did. And what a climax it was. She was so animated, that at one point, I thought she was going to roll over and fall onto the grass. There was also a lot of noise. I was impressed, and, when her orgasm was over, I thought about telling her that. But I decided that it was probably a bad idea.

As I sat back on my chair, she started to come round. After closing her legs, she opened her eyes, but she didn't look at me. Then she sat up.

"I'll get us both a cold drink."

She just nodded. I then went into the kitchen. I waited a few minutes before returning, to give her time to compose herself.

When I handed it to her, she took a large swig of it.

"Thanks, I needed that."

When she had said it, she was looking at me, and she was smiling. I was now smiling as well, thankful that the awkwardness between us had now gone.

I stayed with her for another ten minutes, and then I went to my room. As soon as I got there, I took my cock out.

I was now slowly stroking it, reliving what had happened. I couldn't believe how far I had got. Alex was a genius, and, after I had climaxed, I was going to call him and tell him that.

I managed to make it last for almost fifteen minutes, and then when I spurted, it nearly hit the ceiling. That was an exaggeration, but it had been impressive.

"Hi Alex, you are a genius."

"Thanks, but I already know that. Did you call me just to tell me that?"

"No, I want to tell you what happened between me and Mother."

"Let me guess. She gave you a black eye."

"No, and not even a fat lip."

It took me ten minutes to tell the whole story. He listened, without commenting, until I got to the end.

"You did well."

"Yes, but that's because I took your advice."

"Thanks, but do you want to hear what I have to say?"

I said yes, but when he had finished, I wished I hadn't. While I was in the garden, he had been in bed with his Mother. He had made her climax twice. The first one with his tongue, and then with his cock, as he fucked her from behind. Now, what I had managed to do with my Mother, didn't seem that impressive.

Later on, my Mother went out with some friends. And she returned when I was already in bed. This time, she didn't wake me up. But what did, was the heavy rain on the window. So by chance, my prediction about the weather, had been correct!

It was six o'clock, too early to get up. I put the covers over my head, and then I tried to get back to sleep. Surprisingly, it worked. When I opened my eyes again, it was eight. I showered, and then I went downstairs. Mother was in the kitchen.

"You are just in time for breakfast. I was about to call you."

I made us both a coffee, and then I sat down at the table. While she worked, I watched her. Yesterday, we had crossed a line. But you wouldn't know it. It was as if it hadn't happened. It had, but how was I going to make it happen again? Today, sunbathing wasn't an option, and the forecast was for rain until the end of the week. I thought about it while I was eating. When I had finished, I still hadn't come up with a plan, and it felt as if I never would. But I knew somebody who might be able to help. It was Alex. I went to my room, and then I called him. It didn't take me long to explain it to him.

"Let me think about it."

It was over an hour before he rang me back.

"I can think of two ways that you can touch her. A massage, or helping her to work out. Does she have any muscle problems, or a bad back?"

"No."

"What about exercising? Does she do any fitness work at home?"

"We have some Gym equipment in the basement, but she hasn't used it for a while."

"That looks promising. Encourage her to start doing it again, and say that you will join her. You can hold her while she stretches. It might lead to something."

"Thanks Alex."

It was a long shot, but I couldn't think of anything better, so it was worth a try.

I waited until we were having our evening meal, before talking to her about it. But she wasn't interested. And it soon became obvious, that nothing I could say, would make her change her mind. I stopped trying to convince her. I, or Alex, would have to think of something else.

The next day, I went to see Alex. His Mother let me in.

"He's in his room. Just go up."

"OK."

Then I gave her a nice smile. I got an even better one back. Was she coming onto me? I thought about that while I was going up the stairs. That was silly. She didn't need me, because she now had Alex.

He was watching an episode of the old Kung Fu series.

"This is like you and me."

"What do you mean?"

"You are Kwai Chang Caine, and I am the Master."

Then he laughed. I didn't think it was funny, but he did have a point. I was now his pupil, coming to him for advice. I then told him about my failed attempt.

"Patience Grasshopper."

He laughed again, but I kept my face straight. I didn't want to encourage him. I found it amusing when the shaolin monk said that to his pupil, but I didn't like him saying it to me.

I didn't stay long. He was calling himself the Master, but I didn't get anything new from him. I was disappointed. I had expected him to come up with a brilliant idea, but he hadn't.

When I got home, Mother was out. It was three in the afternoon when she got back, and she had been drinking. She wasn't drunk, but she was a bit unsteady on her feet.

"Be a darling, and make me a black coffee."

I went to the kitchen. While the kettle was boiling, I heard her shout, "I want it strong."

When she tasted it, she winced.

"That is strong!"

"It's what you asked for."

After a couple of sips, she put it down. Then she took her shoes off.

"My feet are killing me. These new shoes are too tight."

She then started rubbing her feet.

"I'll do that for you."

We were now on the sofa. And she had her legs on my lap.

I was pleased with myself. I had been quick-witted enough to see the opportunity, and go for it. However, her letting me touch her feet, didn't necessarily mean that she would let me do more than that. But I was going to try.

"That feels good."

"You look tired. Why don't you close your eyes? You might fall asleep."

She didn't answer me, but she did close them.

I was now slowly moving my hand up her leg. When I got to her knee, it was decision time. That was where the hem of her skirt was. If I was to continue, then I would have to go under it. And there would then be no mistaking what my intention was. I hesitated, but then I thought about what had happened in the garden. She had been willing then, so surely she would be willing now. There was only one way to find out. When my hand touched her thigh, she moved, and it startled me. I thought she was going to get up, but she didn't. Instead, she spread her legs. And when I pushed her skirt up, her pussy was exposed. And this time, it was only covered by a thong.