Two Friends Make a Bet

"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.