Two Friends Make a Bet

chris99999©

"What should the last one be?"

"A virgin."

For some reason, that cracked both of them up.

"What's wrong with that?"

Looking at Jacob, Ryan said, "You tell him."

"Where we live, they don't exist."

That set them off again. I had to smile, they did have a point. It was OK them laughing, but did they have a better suggestion? Then I thought of something else, but would they find that funny as well? There was only one way to find out.

"How about our Mothers?"

That got their attention.

"Jacob, your Mother on my list, and mine on yours."

"Or it could be your own Mother."

I shook my head. As much as I would like to, what Ryan had said was never going to happen. Jacob's Mother, yes. But not my own.

Then Jacob said, "Why are you being a pussy?"

He was smirking, as he tried to stare me out. I held my gaze, and he was the first to look away. I thought it was over, but then he started making clucking noises. Ryan joined in.

That evening, while I was in my bedroom, I took the paper out of my pocket. I knew what was on it, but I read it again. I had made a bet with Jacob. The first to have sex with four women was the winner. Not just any women.

(1) Old. Must be at least fifty.

(2) In a public place.

(3) A natural blonde.

(4) Your Mother.

I was OK with the first three, but the last one was making me feel uncomfortable. I had been backed into a corner, and the only way to save face had been to say yes.

The next day, we met up again.

"Have you changed your mind?"

While Jacob had said it, he was smirking. And I could tell that he, and Ryan, were hoping that I would say yes. I smiled at them, and then I shook my head. They had started to annoy me. I now wasn't just going to do it. I was going to win!

Half an hour later, I went home. It hadn't taken us long to finalize the details. Ryan wasn't competing, but he was going to adjudicate on any disputes. To tick somebody off the list, you had to have full sex with them. Ryan summed it up perfectly.

"You have to come in their cunt."

However, you didn't need to make them climax. Also, you couldn't tell them about the bet, or pay for it.

When I got home, Mother was in the kitchen. I made myself a coffee, and then I sat at the table. As I drank it, I watched her working.

She was only forty two, but she dressed as if she was a lot older. Jacob's Mother would often wear a short skirt, and a revealing top. But she never did. She was always covered up.

"Did you see Jacob and Ryan today?"

"Yes, we went to the park."

"What did you decide?"

I was shocked. How on earth did she know about the bet? Then I realised that she was talking about the camping trip.

"We are going to do it."

"Good, but how are you going to pay for it?"

"I have some money saved, and I'm going to look for a job."

That was true, but I was hoping that Jacob would be paying for me. However, for that to happen, I would have to win the wager.

After our evening meal, I went to my room. As I lay on the bed, I thought about tomorrow. It was an important day. That's when we would start.

We were evenly matched. Jacob was better looking than me, but I had the gift of the gab. Both of us were reasonably successful at bedding women, but I would like to think that I had the edge on him. This contest would determine if that was true. I was desperate to win. Not just for the money, but for the bragging rights. However, if I was going to win, then I needed a plan.

Half an hour later, I had one. Mother was going to be difficult, and it wasn't something I could rush. I would need all my charm to persuade her, and it would take time. It was best to get to work on her as soon as possible. I could fit the others in while I was softening Mother up.

The next day, I was up early. I quickly showered, and then I went downstairs. Mother was in the kitchen.

"You're looking good today. Are those new clothes?"

She looked surprised, and then she laughed.

"You must want something. What is it?"

I wanted to fuck her, but coming straight out with it, was never going to work.

"Nothing. Can't a Son pay his Mother a compliment?"

She didn't reply, but she was now smiling. As she made my breakfast, I thought about her.

She had a nice figure, but it was always well hidden. She dressed as if she was trying to conceal it. Jacob's Mother would often show a lot of cleavage, but she never did. This was going to be difficult, perhaps even impossible.

After lunch, I went to Ryan's house. Jacob was there, and he was sporting a fat lip.

"His Mother slapped him."

I looked at Jacob, for confirmation. He nodded.

"I gave her a hug this morning, and while I was doing it, I grabbed her tits."

With a straight face, I said, "So did you manage to fuck her?"

He was about to answer me, but then he realised that I was teasing him, so he kept quiet.

It was late when I got home, and Mother was already in bed. I watched the game that I had recorded, but my mind kept wondering. When was the last time that Mother had dated? Two years ago, or even longer? That had been Andy, and it had lasted less than three months. After that, she seemed to lose interest in men. And now I was supposed to have sex with her.

It was almost one in the morning before I went to bed, and I was soon asleep. In the morning I was woken by Mother knocking on the door.

I mumbled, "Come in."

"I'm doing the washing, so I need your sheets."

I ignored her, and she moved towards the bed.

"If you don't get up, I'm going to pull them off."

"No, I'm naked!"

I was, and I had woken up with a stiffy.

"OK, but if you are not out of bed in five minutes, then you are in trouble."

Then she left, and I cursed myself. Why hadn't I let her do it? She would have seen my cock standing to attention, and it might have kindled some desire in her. It's not a monster, but it's seven inches of thick meat. And, at twenty two, I was confident enough to believe that it would be able to satisfy her. She had taken me by surprise, but the next time I would be ready.

I did get up, but I waited until Mother shouted me. I had stayed in bed, hoping that she would come into my room, and rip the sheets off. She would then see my erect cock. But instead, she had stayed downstairs.

"What are you doing today?"

"Nothing."

"Good, then you can do some shopping for me. I've made a list."

I didn't bother looking at it, until I had eaten my breakfast. It was three full pages. Mostly food, but some cleaning stuff. After lunch I went out to do the shopping.

I had finished, and was loading the car, when she approached me.

"Are you Alex Smith?"

"Guilty."

That made her giggle.

"Do I know you?"

"I was at the same school as you."

She had a padded coat on, with the hood up. All I could see of her was her face, and I didn't recognize it. I had no idea who she was.

"I'm Sarah West. You probably didn't notice me. I was a few classes below you."

Then she giggled again. The first time it had been amusing, but now it was embarrassing.

As I gave her a big smile, I said, "It's been nice meeting you. But I need to go."

I was turning to leave, when she pulled her hood down. I was now interested in her.

"I hope you don't mind me asking. I'm trying out a new bar tonight. Would you like to come with me?"

Her face lit up, and then she nodded. Five minutes later, I was driving off. I was picking her up at eight. She was only eighteen. I prefer my women older, at least in their twenties. However, she was beautiful, but more important, she was blonde. And unless I was mistaken, it was natural.

When I got home, Mother was pleased. I had managed to get everything on the list.

At seven thirty, as I was about to leave, Ryan called.

"Have you scored yet?"

"No, but I'm working on it."

"Then it's one-nil to Jacob."

"His Mother?"

That made him laugh.

"No, the woman that owns that little bookshop that he likes to go to."

I knew who she was. I had been to the shop with him. She was in her fifties, and he always flirted with her. This time he had taken it further. Apparently, she had closed the shop, and then bent over the desk for him.

Sarah was waiting at the door for me, and it made me feel guilty. But I was still determined to do it.

It was eleven when we left the bar. And to my surprise, it had been enjoyable. She was good company. We went back to her place. That's where we kissed for the first time. It wasn't long before my hands were on her small breasts, and she didn't stop me. When I found her nipples, she groaned.

"We can do it, but we need to be quiet. I don't want my parents coming downstairs and finding us screwing."

Then she giggled, and I stifled it, by kissing her again. When I tried to unbutton her top, she stopped me.

"No, but you can take my knickers off."

As soon as they were off, she lay down on the sofa, and opened her legs. I lifted her skirt up, to give me access to her pussy, but also so that I could see her pubic hair. I was pleased to see that she was a natural blonde, but it wouldn't have mattered if she wasn't. This wasn't just to help me win a bet, this was because I wanted to.

Two fingers slid into her easily. I then fucked her with them. As I moved them, I looked at her face. I could see how much she was enjoying it. But she was enjoying it too much, because she suddenly climaxed.

"Oh no!"

Her body went rigid, only relaxing when her orgasm had ended. I was so surprised, that I still had my fingers inside her. When she pulled on my hand, I removed them.

"Sorry, I get too excited. I should have warned you."

I mumbled, "Yes you should have."

For some reason she laughed, but I didn't think it was funny.

"Don't worry. You can still fuck me," then she giggled, before adding, "And if you are any good, I'll come again."

When my cock was out, it got an appreciative nod from her. She then got onto all fours, and I was quickly behind her, and even quicker pushing into her. She grunted when it was fully in. She had set me the challenge of giving her a second climax, and I was determined to achieve it.

Five minutes later, I wasn't sure that I could. Yes, she was enjoying it. And yes, she was highly excited, but her climax seemed a long way off. I upped the pace. That moved her on, but it moved me on even more. I could feel the sap rising. I wasn't going to be able to last much longer. If I wanted her to reach it with me, then I would have to do more to her.

I hoped it would work, and it did. I had reached under her, so that I could rub her clit. As soon as my fingers were on it, her moaning went to a different level. I was now frantically fucking her, as I also serviced her clit.

When she climaxed, I wasn't far behind. As I poured into her, she collapsed onto the floor, taking me with her. We lay there together for some time, her whimpering, and me breathing heavily.

We parted with a kiss, and a promise from me, that I would call her. And I would. I liked her, and the sex had been good. She was more than just a tick on my list.

The next day I called her, wanting to see her again soon, but she said no.

"I need to study. I have an important exam on Friday."

I wasn't happy, I would have to wait until the weekend. And that was three days from now.

On Thursday, I met up with my friends. As expected, the first topic of conversation was the bet.

"So Alex, is it still a big fat zero?"

"No."

That took the smile off Jacob's face.

"What about you?"

"My Mother fell asleep on me last night, while we were watching television. I had a quick feel of her tits."

He was expecting us to be impressed, but we weren't. He wasn't happy when we laughed. So we were now even, at one each. I then told them about Sarah, but only enough so that they would believe that I had done it. I hadn't mentioned her name. If our relationship continued, then it was likely that she would eventually meet them, and I didn't want them to know that she was the blonde from my list.

On my way home, I kept thinking about what Jacob had said, and it made me smile. But it also made me realise, that having sex with your Mother, was not an easy thing to do. He wasn't having any success, but at least he was trying.

As soon as I got in, an opportunity arose. And I took it.

"I don't know what I have done, but my back is killing me."

She then placed a hand on her lower spine, to show me where the pain was.

"I can sort that out."

I then gave her a big smile, before saying, "I'll massage it."

My suggestion had surprised her, but she hadn't instantly dismissed it. She was thinking about it, and if I acted quickly, it might tip the balance.

"You do a lot for me. It's my turn to help you."

I then held my breath, as I waited for her answer.

We were now in her bedroom, and I still couldn't believe that she had agreed to it. However, there was still another hurdle to get over. She was face down on the bed, ready for me to start, but she was fully clothed.

"I'm going to use oil on you."

"You can't, it will ruin my clothes."

I sighed, and then I said, "Yes, that's my point. You need to take your skirt and top off."

"Do you think this massage will help me?"

"Absolutely."

"Then I guess I had better do it. Turn your back while I get undressed."

I did, and I then heard her groan a couple of times while she was doing it.

"I'm ready."

When I saw her, I almost dropped the oil. She had removed her bra as well. It was what I wanted, and during the massage, I would have suggested it. However, I had thought that I would have to convince her, but she had surprised me, by doing it without me having to ask.

My first touch made her wince.

"Sorry."

My next was gentler. As I massaged her, it was easy to tell where the problem area was, because of the response I was getting from her, and because if felt tight. She had strained a muscle in her lower back.

"That's enough."

She had let me work on it for ten minutes, longer than I thought she would.

"How does it feel?"

"Sore, but I think it's done some good."

"I've just thought of something else that might help."

"What's that?"

"Back problems can be caused by tightness in the buttocks. I can massage you there as well."

"OK."

She had surprised me again. I had got permission from her to put my hands on her bottom, without a fight. It's a good job that she couldn't see my face, because I was now smiling. It wasn't something I had suddenly thought of, it was part of my master plan to seduce her.

I started high up, but my hands were soon on her cheeks. The oil was soaking into her knickers, and I was waiting for her to notice, and then ask me to stop. When that happened, I was going to suggest that I lower them, to stop them being ruined. But she wasn't saying anything.

Her ass was firm, and having my hands on it, had given me an erection. I was now feeling her, rather than massaging her. And she was responding. She had sighed several times, and there had even been a low moan, when I had pressed down hard.

"There's some oil on your knickers. I'll move them out of the way."

She mumbled something. I didn't catch what it was, but it didn't sound like no, so I did it. Just a few inches, to test the water. My hands were now on her, and I was slowly moving them down, taking her knickers with me. Her bottom was now exposed. If she was to open her legs, even slightly, I would get to see her pussy.

I stopped, so that I could dribble some oil onto her, it went between her cheeks. I then placed a finger on the oil, tracing its path. I was now close to her first opening. When the tip of my finger touched it, she tensed, but then she relaxed. Should I push my finger in, or move down and go for the greater prize?

"We need to stop."

I had gone for her pussy, and I was almost there. I thought I had her, that she was willing to let me continue. But I was wrong. After pulling her knickers back up, I left the bedroom. Half an hour later, after showering, she joined me in the kitchen. I could tell, that like me, she didn't know what to say. There was now an awkward silence, that needed to be broken.

"Is your back any better?"

"A bit."

"Good, I'll do it again in a couple of days."

"I would like that."

She had smiled as she had said it, so I knew that she meant it.

The next day, when I woke, my cock was already hard. And it was throbbing. It wasn't going to go down, until I gave it some attention. As I played with it, I thought about Mother, and how close I had been to fingering her. Then my phone rang, but I ignored it. I had just got back into a nice rhythm, when it rang again. This time I answered it. It was Jacob.

"Hi, Alex. Doing anything special?"

"No, just stroking my cock."

"Very funny, but what are you really doing?"

"I'm still in bed."

"If you snooze, you lose."

Then he laughed. I waited until he had finished, before saying, "It's early, so you must have a good reason for calling me."

"Do you know Jan, my Mother's friend? Last night I fucked her."

I did. I had met her twice. She was dog rough, and would have sex with anybody. Fucking her wasn't something to boast about, so he must be telling me because she was another one off the list. She wasn't blonde, therefore they must have done it in a public place.

"So where did you do it?"

"In that alley next to the pizza shop."

I knew it well. A year ago, a girlfriend had sucked me off there. She was good, and the experience had been heightened, because of the risk of being caught. It was definitely a public place. When the call ended, I was deflated, and so was my cock. I didn't bother trying to revive it.

At breakfast, Mother noticed that I was sullen.

"Is anything bothering you?"

"No, I'm just a bit tired."

I could tell that she didn't believe me.

"If there is anything I can do to help, then let me know."

I gave her a big smile, and then I shook my head. But there was something she could do. She could open her legs, and let me fuck her.

In the afternoon, I was in a better mood. That was after Sarah had called me. I was going to be seeing her tomorrow after lunch. Her parents were away for the weekend, and I was determined to make the most of it. It was going to be a fuck fest. But it wasn't going to help me to win. Was there anything I could do today? It was too soon for Mother's next massage, but there was no harm in asking. I went downstairs to find her. She was in the kitchen, sitting at the table.

"Did my massage help?"

She stood up, and then she did some stretching. When she had finished, she was smiling.

"It's a lot better. If I had done that yesterday, then the pain would have been almost unbearable."

"Good, but it's best if I massage you again. I can do it now."

She shook her head, and then she said, "I don't think I need it."

Damn, I had done too good a job. An hour later, I tried again, but I got a firm no. That's when I gave up.

After our evening meal, we watched television together. It was an interesting programme, but my mind kept wandering. I was either thinking about Sarah, and what we would be doing tomorrow, or trying to plan my next conquest. The woman at the bookshop, who had let Jacob fuck her, was a possibility. Next week, I would visit her shop. It felt like a long shot, but sometimes they pay off.

When the film ended, I was ready for bed. And it looked as if Mother was as well. Then she surprised me.

"Does your offer still stand?"

"The massage?"

"Yes, it's hurting now, probably because I have been sitting down for a while."

We went to her bedroom. And this time, I didn't have to ask her to take her clothes off. She was face down on the bed, and I was staring at her bottom. It was covered by a towel, and underneath it she was naked. I knew that, because I could see her knickers on the floor, next to her other clothes.

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.

"Fuck, I'm going to come."

I grunted, "Me too," and then I gave her my best stroke. It did the trick.

"I'm in it."

She definitely was, and it looked to be a big one. But I was more concerned about mine, and whether I would get one or not. I did, but it took me another thirty seconds. She had waited patiently for me to finish, and I was grateful for that.

As I walked home, I thought about the bet. We were now even. Then I laughed. No, I was one up. I had fucked her outside, in a public place. She counted as two. I then rang Jacob, so that I could gloat. Before I could tell him about my success, he told me about his.

I asked, "Are you sure that she was a true blond?"

"Yes, I took a picture of her pussy. Do you want to see it?"

I said no, and then I told him my news. I was expecting him to argue with me, to say that you couldn't count it as two. But to my surprise, he accepted it. And he was even impressed.

"Nice one Alex."

He then surprised me again.

"Do you think we should call it off?"

I thought about it. We were level, at three each. So we could.

I answered with, "Yes. It was a stupid idea."

He quickly agreed with me. The bet was now officially dead.

When I got back home, Mother was out. I went up to my room to read. I was part way through a book, that wasn't very good, but I was determined to finish it. Then I thought about the bet. Jacob's reason for wanting to end it, was obvious. His Mother was proving to be a lot more difficult than he had expected. But what was my reason? If we had continued, then I would almost certainly have won. I desperately wanted to fuck my Mother, but doing it to win some money, didn't feel right. But was I still going to do it?

Of course I was!

It was late when Mother got back, and she went straight to her room. I stayed up for another hour, watching television, and then I went to bed. I was drifting off to sleep, when the door opened.

"Move over, so that I can get in."

She was standing there, with a big smile on her face. And she was naked.

"Or I could go back to my room."

That got a quick shake of my head, and a loud, "No."

It made her laugh.

She was now in bed with me.

Turning her head towards me, she said, "You do know that this is a bad idea."

I nodded.

"And that one day we will regret it."

I nodded again.

Then I kissed her, because I wanted to, but also to stop her talking. She might think that it was a bad idea, but it wasn't stopping her from kissing me back, and with an eagerness that matched mine.

I now had my fingers on both her nipples, pulling and pinching them.

"That's nice, but my pussy needs some attention."

I gave her two fingers, up to the knuckles. It took her breath away. I then fucked her with them.

"Stroke my cock."

She did, but way too fast.

"Slow down."

"Sorry, I'm a bit rusty. It's been a long time since I've done this."

Jokingly, I said, "Just be careful, you nearly ripped it off."

That made her laugh.

She was now giving me long slow strokes, while I fingered her. We were enjoying it, and if we just continued doing this, then it would end with both of us climaxing. But I wanted her pussy, rather than her hand.

"Can I put it in?"

"Yes, that's why I came to your room."

I didn't know what to say. A few days ago, she had just been my Mother, but now she was my lover. And, for the first time, we were going to fuck.

Without asking, she got onto all fours. I was quickly behind her. I took a moment to admire the view. I liked her plump bottom, and narrow waist, but it was her cunt that my eyes were drawn to.

I was now in position. The head of my cock was as big as it had ever been. It looked as if it was going to burst. When I pushed into her, she moaned. And when I was fully in, she grunted.

"I'd almost forgotten how good it feels having a cock inside me."

She was about to say something else, but she stopped when I started fucking her.

It was slow at first, but then I got carried away. I just couldn't help it. I was overcome with lust. I was giving her long hard strokes, sometimes so hard that I was nearly pushing her down onto the bed. Fortunately, she wasn't just taking it, she was enjoying it as much as me. Perhaps even more. If she was any louder, then the neighbours would complain. I didn't care. I had only one thing on my mind, to spurt into her juicy cunt.

"I'm on the edge. Do something."

She sounded desperate. But what would tip her over? I was going to reach forward so that I could grab her tits, but I decided that it would be better to go for her clit.

"Yes!"

Good, it had been the right thing to do. I was now frantically rubbing it, while I continued to fuck her. Seconds later, she climaxed. To call it a big one, wouldn't do it justice. It was epic. I was impressed, but it had put me off my stroke. It ended with her flopping down onto the bed, taking me with her. When I pulled out of her, I was still hard, because I hadn't climaxed.

When she eventually turned over, the first thing she saw was my erect cock.

"You didn't come?"

I nodded.

"Do you want to put it in my mouth?"

I sighed, and then I mumbled, "OK."

"Or you can fuck me again."

Then she laughed. She had been teasing me.

She was now on her back, with her legs high and wide, and I was fucking her hard. I was getting the occasional moan from her, but it was obvious that she wasn't going to come again. This was all about me.

When I did eventually climax, it was a good one. It would have been better if we had reached it together, but I wasn't complaining. I was lucky. Every Son wants to have his Mother, but I had actually done it.

We were now snuggled up to each other, basking in the afterglow of good sex.

"You do know that what we did was wrong?"

I nodded.

"And that it has to stop."

I nodded again.

But it was too much for me. I laughed, and she joined in. It might be wrong, but we both knew that we were never going to stop!