Two Friends Make a Bet

This time, I started with her shoulders.

"I'll do you upper back first, before working on the problem area."

Last time, I hadn't been patient enough, but I had learnt my lesson. This was going to be nice and slow. At the end, she would be begging me to give her more than just a massage.

When I moved away from her shoulders, I reduced the pressure. I was now massaging her back, but as I did, I was gradually moving my hands away from the centre. Her breasts were squashed against the bed, but I could see part of them bulging out at the side. That was my destination.

I took my time getting there, and my first touch was gentle. But it was enough to make her utter a low moan. That sent a surge of excitement down my spine, and the blood rushing to my cock. The next one was firmer, and there was now no mistaking what I was doing. This time, she didn't moan, but to my surprise, and delight, she lifted her body up. Enough for me to get my hands underneath her. I hesitated, but only briefly.

I now had my hands on her tits, and I could feel her nipples under my palms. Two big lumps, that were getting bigger, as my hands moved over them. She then lifted herself higher, to make it easier for me. My fingers could now get to her nipples, and they did. In record time. When I pulled on them, she gasped.

"Turn over."

She didn't move, so I said it again. I was desperate to see them, and to get them into my mouth. Again, she still didn't move, but she did speak, and it wasn't what I wanted to hear.

"No."

Then she suddenly lowered herself, trapping my hands.

"You need to do my back."

This time, when she raised herself, it wasn't so that I could continue playing with her tits, it was so that I could get my hands out.

I was now giving her a proper massage, concentrating on the muscle that was giving her a problem. As I did so, I kept cursing myself. I had her plump nipples between my fingers, and I had ruined it. I had tried to force it, to get her to turn over. I should have waited. When she was ready, she would have done it without me having to ask.

"Finished."

"What about my bottom?"

Was she serious? She had stopped me playing with her tits, so I hadn't bothered trying to lower the towel.

"Are you sure?"

As soon as I had said it, I wished I hadn't. This wasn't one of my better days. I was such an idiot. I should have just taken her at her word, rather than questioning her about it.

"Yes. Last time when you did it, it helped," then she paused, before adding, "And I liked it."

Her last sentence had given me confidence. I decided to be bold. I didn't just lower the towel, I took it off. I was now admiring her bottom, and as I did so, I was smiling. Her legs were closed, but I knew that it wouldn't be long before they were open wide.

I started with my hands on her cheeks, pushing down hard. I then moved them in a circular motion. That got appreciative moans from her. Asking her to turn over, had been a step too far for her. That would have meant exposing her breasts, and making it obvious what we were doing. By staying face down, she could keep up the pretence that this was just a massage.

My hands were now lower, just above her knees. They were there so that I could push her legs apart. This was the test. If she didn't stop me, then she was mine. At first, she wouldn't move them, but when I pushed harder, she gave in. Her legs were now wide open. I put some more oil on my hands, and then I placed them on her thighs.

I was now slowly moving them up her legs. I stopped when I got close to her pussy. I then massaged her groin. As I did, I kept moving nearer, but never touching her sacred place.

I was amazed that I was holding back. My fingers had been there for such a long time, and I still hadn't fingered her. I was going to, but that was when I had got her so excited, that there would be no chance of her saying no.

It was now time to cross the line. She was squirming, as my fingers kept moving. And she was moaning, almost continuously. She was desperate to have my fingers inside her.

When I ran one of them along her slit, she gasped. Then she pushed back against it. The tip of it entered her. For a few seconds, I didn't move it, then I slowly pushed it into her. When it was fully in, she sighed.

I then started fucking her with it. From the noise she was now making, you would think that she had a big cock inside her, rather than just a single finger. I was seeing her in a new light. I had thought that she had lost interest in sex, but she hadn't. The passion had been there, but she had suppressed it. It was now all coming out.

To my surprise, after a minute at the most, she was close to reaching it. I had expected her to climax quickly, but not so soon. I was hoping that my cock would eventually take the place of the finger that I had inside her, but that wasn't going to happen now. If I stopped, to take it out, it would probably spoil it for her. It was best to just give her what she needed, a climax.

My finger was now moving faster, and she was panting. When I started rubbing her clit, with a finger from my other hand, it took her over the edge.

As I watched her, I smiled. I had done a good job. It was a big one. Her body had gone rigid, and then her arms and legs had thrashed about. It was a while before she relaxed.

As soon as she had finished, I went to my room. I had a throbbing cock to deal with.

I was now frantically stroking it, as I relived what had happened. I had only had a quick feel of her tits, and a single finger inside her, but remembering it, was enough to make me spurt.

I slept well, and I woke relaxed. Then I started getting tense, when I thought about Mother, and what I had done to her. I was OK with it, but was she?

As I approached the kitchen, I was apprehensive. Then I smiled, she was singing to herself. She only did that when she was in a good mood. We had breakfast together, and there was no awkwardness between us. After lunch I went to see Sarah.

She greeted me with a big hug, and then we kissed. I didn't bother with her tits, I went straight for her pussy. As I rubbed it through her knickers, she moaned. I then pushed them to the side, to give me access to her clit. When I found it, she gasped.

"Make me come, and then we can fuck."

I did, in record time. As soon as she had recovered, I was taking her knickers off.

"Let's go upstairs."

While we undressed, I looked around. Her bedroom was big, with a lot of artwork on the walls. I pointed to one of the pictures.

"I like that."

"It's my Father's favourite."

He had good taste. Then it hit me.

"Is this your parent's room?"

"Yes, I've always wanted to do it in their bed."

I was OK with that. I didn't mind where we did it.

We were now under the sheets, just cuddling. Her parents were away until tomorrow night, so there was no need to rush. I was casually brushing her nipples with my fingers. As I was doing it, I was trying to make sense of what she had done before getting into bed. On the bedside table was a framed picture of her Father. He was holding up a trophy. It had been at an angle, and she had moved it. I thought that she was just putting it back to its proper place, but I now realised that she had done it so that she could look at it while we were in bed together.

It was another hour before she got her second climax. The build-up had been slow, but the ending was frantic. We finished with her on her back, and me on top of her, pushing her legs up high. Her head had been to one side, and as she climaxed, she was staring at something. The picture of her Father. While her orgasm had surged through her body, I knew that it was him that she was thinking of.

It wasn't me that had just fucked her, it was her Father!

I left Sunday evening, before her parents returned. When I got home, I went straight to bed. I was exhausted. Over the weekend, we had fucked five times, and the last one had been too much for me. As I closed my eyes, desperate to sleep, I vowed never to have sex again.

It was after nine when I woke. That was late for me. Mother was up, and she had already had breakfast. I sat at the table, sipping my coffee, watching her as she made mine. As she moved, her bottom wobbled slightly, and to my amazement, it got me hard. All thoughts about giving up sex had now gone.

I had only just finished my breakfast, when the doorbell rang. It was Jacob, and from the look on his face, he was bursting to tell me something. I took him up to my room.

"I hope you've got the money ready."

I was disappointed, but I tried not to let it show.

He then declared, "All done, except for my Mother."

So he hadn't won yet, but he had managed to cross the blonde off his list. He had come to see me so that he could gloat about it. He had just started telling me how it had happened, when the doorbell rang again. Mother answered it.

She shouted, "It's Ryan."

When he got to my room, he was surprised to see Jacob.

"I thought you'd still be in bed. You were smashed last night."

"I was, but I still managed to get it up."

"Who with? When you left me, you were on your own."

On my way home, I saw that girl who had been in the bar earlier. The tall blonde one. I stopped to talk to her. I then managed to persuade her to have a quick one in the bushes.

"Yes, she was tall, very tall. And she was blonde. But not a natural."

I looked at Ryan. Was he trying to wind Jacob up?

"I chatted to her when you were away having a piss. She dropped something, and then when she bent down to pick it up, I saw her dark roots."

Jacob was now looking embarrassed.

He muttered, "I should have looked at her pussy."

I wanted to laugh, but I held it in. You don't kick somebody when they are down, especially when they are a friend.

They left after two hours. After seeing them out, I joined Mother in the living room.

"You should have asked them to stay for lunch."

"I did, but they said you were a lousy cook."

I was smiling when I had said it, so she knew that I was only joking.

What she had prepared, was delicious. And, as I ate the last mouthful, I was feeling guilty. I hadn't thought to ask my friends if they wanted lunch with us. Then I noticed that there was a lot left over, so I had seconds. When I had finished, I went to my room.

Thankfully, it was still just two-one to Jacob. However, if I didn't move up a gear, then he was going to win. But what should I do? Concentrate on Mother, or try somebody else? I decided to go to the bookshop. The owner had fallen for Jacob's good looks, and, with a bit of luck, my sparkling personality would win her over.

I was at the front door, ready to leave, when Mother shouted me.

"Alex, come here."

I went to her.

"I was just wondering," then she hesitated, as if she was searching for the right words, before saying, "Would you like to give me a massage?"

I nodded. I had been going out, looking forward to seeing the woman in the bookshop. But now, all I could think about was Mother. And what I was going to do to her.

I waited outside her bedroom, until she called me in.

"I read somewhere, that it helps you to relax while you are being massaged. I thought I would try it."

"OK."

It was the only thing I could think of saying, and I had struggled to say it. She was wearing a small black mask over her eyes. The sort of thing that you wear when you are in an aeroplane, to help you to sleep by blocking out the light. This time, she was lying on her back, and she was naked.

My hands were now on her shoulders, but my eyes were on her breasts. Her large nipples were pointing up at me, begging to be played with. And as I stared at them, they seemed to be getting even bigger.

When I touched them, I knew that she wouldn't stop me. Covering her eyes, was so that I could do what I wanted to her, and she could pretend that it wasn't happening. That was ridiculous, but I wasn't going to point it out to her.

My mouth was now on her, and when I sucked hard, taking in not just her nipple, but as much of her breast as I could, she moaned loudly. I kept on doing it, only stopping so that I could switch to the other one.

Her tits were nice, but I knew that what she had between her legs, was even better. My hand was now on her thigh. When I pushed against it, she responded as I knew she would, by opening her legs wide. I stopped sucking on her tits, and then I moved so that I could see her pussy. I had fingered her before, but only from behind. This was my first opportunity to see it properly. And I was now taking it all in. I liked what I saw.

It wasn't a pussy, it was a juicy cunt!

I then surprised her. She was expecting a finger, but instead she got my tongue. When I had licked her clit, her body had gone rigid, but it had soon relaxed. All the women that I have gone down on, have enjoyed it. I take my time, and I know that I am skilled at it. But Mother's enjoyment was on a different level. After only a couple of minutes, I had to stop. Any longer and she would climax.

My cock was now out, and it was rock hard. I couldn't believe that I was finally going to fuck her. But as soon as my cock was at her opening, the wheels came off. She had quickly clamped her legs together, trapping my swollen member between her thighs.

"No."

Using both hands, I tried to push them apart. If I could open them, then no might become yes. But I couldn't. I was a lot stronger than her, but she had managed to keep them closed. I gave a deep sigh, and then I gave in. She then opened her legs, but only wide enough so that I could remove my cock. I thought that was it, that it would end in dismal failure, but then she spoke.

"Put it in my mouth."

I was so surprised, even shocked, that I didn't move.

"But only if you want to."

I almost laughed. Of course I wanted to. I would have preferred her cunt, but that wasn't on offer. However, her mouth was a lot better than nothing.

At first, she just licked the head, running her tongue around it. Then she took it into her mouth. Just a few inches, but enough to excite me. It must have been a long time since she had done this, but you wouldn't know. She was an expert.

She was now taking me towards a climax, and I was doing the same to her. I had two fingers on her clit, and they were working their magic. It wouldn't be long before we both reached it, but who would be first?

It was me, but only just. As I spurted into her mouth, she boiled over. She was swallowing my semen, as her orgasm surged through her body. When my balls were drained, she was still going.

I only removed my cock when it started going limp. Then I stepped back from the bed. When I looked down at her, I had to smile. It was a strange sight, and if I was to tell anybody about it, they wouldn't believe me.

My Mother was naked, except for the mask covering her eyes. Her legs were still open, and there was something dribbling down her chin. If my phone had been with me, then I would have taken a picture. But it would be one that I would never be able to show anybody.

It was almost another hour, before we were together again. She had showered first, and then she had gone downstairs. After my shower, I had gone back to my room. I only left it when she called me. As I went downstairs, I tried to think of something to say to her. It was going to be awkward.

But it wasn't. As soon as I entered the kitchen, she hugged me. Then she whispered in my ear, "Don't say anything."

After releasing me, she made us both a coffee. We than sat together at the table, talking. It was as if nothing had happened.

That night in bed, there was no need for me to play with my cock, because Mother had already drained my balls. But in the morning, I was ready for sex again, and it was time to tick another one off my list.

"Where are you going?"

It was an innocent question, but it made me feel guilty.

"Just to Ryan's."

I wasn't really. I was going to the bookshop. Yesterday, we had almost fucked, and it had ended with me fingering her to a climax, while she swallowed my semen. And now I was lying to her. I didn't feel good about it, but my desire to win the bet, was driving me on.

As I approached the shop, I took a deep breath. I was now ready. I knew what I was going to say to her, and I had convinced myself that it would work. The door was stuck, so I pushed hard on it, but it refused to open. Then I noticed the sign.

'Sorry we are closed. Open again on Monday'

I cursed under my breath. All that way for nothing. I would just have to go home, and come back next week, when the shop was open again. I felt deflated. Then I had an idea. But I quickly dismissed it. However, as I walked away, I thought about it again. I then turned around, and headed back towards the bookshop. But that wasn't my destination. I was heading towards the bar at the end of the street. I had never been to it before, because it had a reputation for being rough. The sort of place where fights break out at the drop of a hat.

I was now inside, drinking a beer. I was trying to blend in, to go unnoticed. But it wasn't working. I was beginning to think that this was a mistake. Then I saw her, and I changed my mind. I had heard that this was a good place to score with women, as long as you weren't fussy, and you liked them old. It was why I was here, and the woman in the corner was giving me the eye. I was about to go to her, but she came to me.

"Would you like to buy a lady a drink?"

I wanted to say, "You go and find a lady, while I order it."

That would have been funny, and she might have laughed. But it was more likely that I would end up on the floor, seeing stars.

Instead I said, "Yes, what would you like?"

We were now drinking together. As she sipped her cocktail, I appraised her. She was mid-fifties, possibly older. She was what I had come in for. Now I needed to seduce her.

She was good company, and we laughed a lot. An hour later, we were best mates. When she suggested that we go to her place, I was eager. And not just because I was trying to win a bet.

We went out through the back of the bar, into the parking lot. She then suddenly kissed me. I kissed her back, with genuine passion.

When we surfaced for air, she said, "Have you ever done it outside?"

I hadn't. A blowjob, yes, but not full sex.

"No."

That made her smile, and it was a wicked one. She then walked away from me, and I followed her. We were now between two cars. It was a more private place, but there was still a good chance that we would be caught.

I kissed her again, but this time I groped her big tits.

"No. Finger me, and then we can fuck."

My hand was now between her open legs, and I was pushing my fingers into the side of her loose knickers. Then I had two of them deep up her cunt. There was room for more, so I added another. That made her groan. When I started fucking her with them, she reached down to unzip me. When it was out, she stepped back so that she could see it.

"That's a big cock. Would you like to put it into my little pussy?"

I nodded several times, and it made her laugh

She was now on all fours. Her knickers were off, and my cock was at her opening. When I pushed into her, she groaned. My cock is only seven inches, so it might not be regarded as big. However, her referring to her pussy as little, was a blatant lie. My cock is quite thick, but it was barely touching the sides.

I was now fucking her hard, and from the noise she was making, she was obviously enjoying it. I was getting some pleasure from it, but it would be a lot better if she was tighter. Then her moaning increased, and I knew that she was close. I needed to concentrate. If it ended without me reaching it, then it wouldn't count.

She was now getting my best effort, and both of us were benefiting from it.