A Bet Gone Wrongbymikeaday©
Thanks to hkf999 for the edit.
Ryan and Joseph were walking back to Ryan's house when they noticed his mother sitting out on the porch. She wasn't a bad looking woman considering she was in her early forties. Ryan wasn't to bothered he just thought of her as mom. Some of his friends had other ideas though.
"Your mom is one hot MILF." Joseph said as he continued to stare at the woman on the porch.
"Shut up, my mom is a saint," replied Ryan knowing that Joseph was only joking.
Normally that would have been the end of the matter but Joseph was feeling bold so he continued.
"Seriously, I would fuck her if I had the chance, I mean who wouldn't?" He said.
"What's that supposed to mean?" Asked Ryan starting to get a little pissed off now.
"Well, she's only in her forties, her tits haven't started to sag yet and she has an ass to die for," replied Joseph.
"Just shut up ok, she my mom and she would never be with an ass hole like you anyway," said Ryan although he couldn't disagree with any of the facts that Joseph had presented. If it was any other woman he would probably have had those same thoughts.
"Care to make a wager so?" asked Joseph with a little smile.
"What are you on about?" asked Ryan as they reached the porch.
"I'll tell you inside," said Joseph as they stopped to talk to Ryan's mother for a few minutes.
Joseph kept trying to look down through the gap of the loose material of the t-shirt that Mrs Clemens was wearing. He would have only managed to make out a pink bra but little else. If she noticed his staring, she gave little indication.
Ryan, who had definitely noticed his friends staring, pulled him into the house. When they were safely behind the closed door of Ryan's room Joseph restarted the topic.
"So as I was saying your mom is hot," said Joseph.
"What will it take you to shut up about that?" asked Ryan knowing that once his friend got something into his head it was hard to get it out of him.
"Like I was saying outside a wager, I bet you 100 dollars that I can fuck your mom."
Ryan didn't know whether to be angry or exasperated. "Assuming I agreed. What makes you think you stand a chance anyway?" he asked unable to stop himself.
"Well, I'm young, handsome and I've got a secret weapon," he said, then added almost as an afterthought "Oh and your mom looks like she needs a good fuck anyway."
Ryan kept calm and starting thinking the wager through. There was a new pair of sneakers that he wanted and it would be an easy way to make a hundred quid. He looked over at his friend. He was six foot tall and had a six pack, he thought himself God's gift to women but so far as Ryan knew he had only slept with one. His mom would never be interested in someone like that would she? It had been a few years since his father had left, surely she wouldn't be that badly off that she would fuck the first 18 year old to hit on her.
As Ryan's resolve hardened that his mother would never do what Joseph asked he started nodding his head slightly. Joseph noticed the motion and said, "So the bet is on then."
"Under two conditions," said Ryan.
"Sure, what are they?" asked Joseph eager to start his courting.
"One, If in the unlikely event you do succeed in seducing my mom and having sex with her, you can't tell anyone else. It has to stay just between us agreed?"
Joseph took a couple of seconds to think this over. It would make for an excellent story if he managed to succeed but if he didn't agree to the terms he wouldn't be able to get a shot. Reluctantly he agreed to this first condition then asked for the second.
"I have to watch," said Ryan.
"What, you want to watch me fuck your mom, that's sick man," said Joseph slightly surprised at this request.
"Well, I can hardly take your word for it or ask my mom afterwards, can you imagine that conversation. "Hey mom, guess what Joseph said he just fucked you, is that true?" I'm sure she'd love that," said Ryan angry at the insinuation that he would enjoy seeing his mother being fucked.
"You're going to have to hide in the closet or something so, is there a place in your mother's room that you could hide in?" asked Joseph warming to the idea.
"Ya, there is a closet that has those slatted things and it should offer a good view of the bed," said Ryan.
"Fine I'll go out and start on your mother and you go hide in the closet," said Joseph.
"Ya you go try that, I'll probably be in the closet a long time." Replied Ryan being as glib as he could.
As Joseph went outside Ryan made his way to his mother's bedroom. The room was tidy with nothing left on display. Ryan went over to the closet and was about to open the door to have a look around when he heard voices coming down the hall. He opened the door and squeezed inside just in time. He had a good view of the room and was able to see Joseph practically dragging his mother into the room. Ryan was glad to see that she was reluctant and his faith in her increased as did his anticipation of those new sneakers.
They were talking so he held as still as he could and listened.
"Come on Mrs Clemens there is something I really need to show you." Joseph said practically dragging her into the room.
"Joseph I don't have time for this and I told you to call me May." May replied exasperated.
"It will just take a second and I promise you won't be disappointed" said Joseph as he finally let go of May's hands.
Ryan waited quietly in the closet and wondered what Joseph was up to. He stared through the slots and watched as Joseph reached around to open his jeans.
"Look Joseph this is all flattering but I don't see what...."
Josephs back was to him and he watched as Joseph lowered his jeans to the ground.
These were shortly followed by his boxers. Ryan was just thinking that his mother would hit him or something for his arrogance.
"Wow you don't see that everyday," May said as she struggled to contain her excitement.
"What you mean Ryan's isn't this big?" Joseph asked with a smirk in his voice.
"NO it's nowhere near that big. I mean I saw it there a month ago. I caught him wanking to a playboy or something," May replied
Ryan stiffened in the closet remembering that day. He had thought his mother would be at her friend's house for a while and had got out his porn stash. When she entered the room he was so surprised that it took a couple of seconds before he stopped wanking. He had thrown up his hands and his mother had gotten a good view of what he thought was a good size dick. Apparently he was mistaken, Josephs must be massive.
"I mean look I can fit both hands around it," she continued.
"Don't worry by the time were finished tonight it wont be just your hands around it," replied Joseph.
"That's good but your going to have to take it easy on me, it's been a while," said May
"I'll take it easy all night long don't worry."
Ryan watched as Joseph started to lift his mothers t-shirt up. He had it just above her navel when his hands stopped moving upwards. He wondered what was wrong and then heard Joseph say.
"You're going to have to let go of it for me to get you undressed."
"Sorry it's just so big and feels so nice," May replied, finally releasing Joseph's dick.
"It will feel nicer inside you don't worry."
"Maybe I should get a mould of it so I can have you inside me anytime I want," said May.
"The real thing will be available any time you need it," he replied.
He wasted no time removing the t-shirt and starting on her jeans. He had also moved to the side a small bit as he was doing this ensuring Ryan had a good view of everything that was going on.
Ryan debated whether to give up on the bet now when it was so obvious that Joseph had won. Something held him back though. He didn't know if it was seeing his mother standing there in her pink bra and white cotton panties or just the desire to see two people have sex in front of him. When Joseph popped the clasp on her bra her breasts burst free as if glad to be out of confinement.
Ryan could feel his dick starting to respond but he tried hard to control it remembering that it was his mother that he was watching. When Joseph pulled down her panties Ryan only just managed to keep his erection down although it was a lot harder. Her dark pubes were trimmed but it must have been a while since she had done it as they were starting to grow wild again. She must have been wet already as some of them were sticking to her fanny.
"You do need some attention don't you," Joseph said as he put two of his fingers into her fanny.
"Well, its not like I could get any around here," said May as she started to respond to Josephs probing fingers.
"What is Ryan not big enough to satisfy you?"
"No, I would hardly feel it if his went into me, I told you I could nearly hold it all in one hand if I tried I'm sure." Said May with something close to regret in her voice.
"Don't worry I'll make up for Ryan's small dick."
Ryan couldn't be sure if his friend was aiming these barbs directly at him or not. When he heard the first tentative moans coming from his mother he couldn't control himself any longer. He let his dick have free rein. He didn't touch it yet but let it stand.
Joseph apparently satisfied with the response his probing had produced, removed his fingers. He offered them to May to lick clean, which she did happily. He then took off the rest of his clothes turning his back to May as he did so. This was the first time that Ryan had seen his friend's dick at full attention and it was impressive. He extracted his own from his boxers dropping them and his jeans to the floor around his ankles. The closet was too dark to allow a visual inspection so he took it in his hand and felt a bit better.
Joseph had manoeuvred May over to the bed and seemed to be deciding on the best position that would allow his access and also give Ryan a good view. He settled at about a diagonal line from Ryan. This would give Ryan the best view of most of her body.
When Joseph had her lie on the bed he started heading back towards his jeans. Ryan thought that he must have had enough fun and was going home now. May must have though the same thing because she called out to him.
"Where are you going you haven't fucked me yet?"
"I'm just getting a condom, I don't want to go giving Ryan a little half brother or sister," said Joseph as he continued towards his discarded jeans.
"Don't worry about that, I told you I want to feel you inside me," said May.
"Well, if you're sure?" replied Joseph still sounding a little reluctant.
"Of course I'm sure and besides it would be such a shame to constrain that thing in any way."
Joseph turned back, his balls swinging under his erect 10 inch dick. "So what position do you like?" he asked her
"Anything as long as you get inside me fast." She said as she moved her own fingers in and out of her pussy.
As soon as Joseph got on the bed beside her she held her pussy lips open to allow his dick to slide into her. He entered slowly making her groan all the way. When she couldn't fit any more in she told him to stop. They had decided to try the missionary position first. As Joseph went in and out slowly, May's moans got louder.
It wasn't a bad position but after a few minutes May said. "I want to be on top is that ok with you?"
"I don't care as long as my dick is in your pussy," Joseph replied.
Ryan watched as they switched positions. He saw that his mother was going to be faced away from him but then Joseph had manoeuvred her so that Ryan had a good view of her breasts. They were now covered in sweat and her deep breathing pushed them up and down rapidly in little arcs.
Joseph's dick looked like a flagpole standing in the middle of his body. Ryan didn't know whether to feel sickened or excited that that had been in his mother and was about to be again.
May lowered herself gently onto Joseph's dick biting her lower lip as she did so. Even from this position she couldn't take it all inside her and had to hold herself off slightly off Joseph. Joseph helped as best he could grabbing a firm hold on her ass. He seemed more interested in her tits though as his hands kept reaching up to play with her nipples.
They must be so hard though Ryan as he watched on from the closet. The panting and moaning coming from Joseph and his mother had made him start rubbing his cock.
"This feels so good." panted May as she rode Joseph's dick as fast as she could. Joseph sometimes lifted his ass off the bed causing his dick to go even further inside her, this produced an exceptionally sharp moan.
Ryan wondered where Joseph got the stamina out of. He could already feel his climax building. He reached behind him for something to catch it in case he did cum. His hand closed around something soft and he decided that this would do. If the material felt this soft in his hands he thought, he wondered what it would feel like on his dick. He wrapped the material around his dick and continued wanking with it. He was trying to figure out what it was when he heard a scream of pleasure coming from his mother.
He saw a shudder pass through her body and wondered if both of them had climaxed. This must have not been the case as she continued to ride Joseph. Joseph must have been bored of this position as he lifted her off him and stood up at the bottom of the bed.
"Don't stop now," May begged.
"I won't I'm just trying to figure out my next position," replied Joseph.
"I know lets try doggy style, Get in position."
"Yes sir," said May clearly enjoying this authoritative change.
May got into position, her ass in the air and her tits visible to the side. Ryan could see her fanny and her ass hole clearly. Joseph approached May and held her pussy lips open giving Ryan a clear view. He winked at Ryan before going to say something to May. Ryan saw a tremble pass through his mother body at whatever Joseph told her. It must have been good.
Joseph bent over May running his dick up the outside of her slit while playing with her tit. Their inverted position making them look even bigger. This time when he entered her it wasn't gently and it took May a second to recover from the surprise. It didn't take her long to adjust though.
"That's it fuck me hard, its so much better having a big dick like yours inside me than a small one like Ryan's." May said between the pounding she was getting. Ryan thought he saw her glance at the closet as she said this but he couldn't be sure as his gaze was fixed on Joseph's dick where it entered her pussy. The heavy breathing and moans coming from his mother were causing his hand to stroke his dick faster and faster. He concentrated and managed to slow down a bit. He wanted to last a bit longer in case they did something else.
"Now for the big challenge," said Joseph as he pulled his dick out of her pussy.
His mother waited in the same position and he wondered what Joseph was up to. Joseph had started to rub his dick against the outside of her slit again. He started near the front of her pussy and stopped with the tip of his dick just above her asshole. Ryan watched him do this a few times and wondered what his friend was up to.
This time when Josephs dick came up it stopped with its tip pressed against her asshole. Ryan could see him pressing his dick gently against it, not hard enough to press it in but enough that he could see the effect the pressure was having on it.
He couldn't stand by and let his friend stick his dick in his mother's ass. He jumped out of the closet and shouted "Stop, don't stick it in there."
His mother turned towards him and just said, "Hi Ryan," in as normal a voice as her heavy breathing allowed.
He was confused for a minute wondering why his mother wasn't surprised to see him bursting out of her closet. All he could come out with was a little "Hi," of his own.
"I see you've been enjoying the show," she said smiling.
"No I haven't, it's not what you think," he stammered back.
"Then why are you using my panties to wank with?" She asked teasing him.
It was only then that he looked down at the soft material that he had been rubbing along his dick. They were a fancy pair of cotton panties with a bit of silk on the front. He noticed that even in the shock of finding out his mother knew he was spying on her, his dick had still remained hard. It was throbbing for release. He wanted to stroke it badly and release the tension but his mother and Joseph were both looking at him.
His mother reached out as if to help him. He couldn't accept that help although he wondered what it would feel like. He was about to run from the room and just finish up in the bathroom when Joseph called him.
He looked up to see Joseph increase the pressure on his mother's ass hole and enter her. The moan of pleasure or pain that came from her mouth did what another one or two strokes would have done. He shot his load into the panties. He felt relief that that particular urge was satisfied but embarrassed that he had been caught and that his mother had seen him.
Even as Joseph continued to fuck her in the ass his mother watched his dick deflate. After that she dismissed him by turning her head away. He had never felt so humiliated but he also felt sad that he had failed his mother in so many ways. He dropped the panties on the floor and pulled up his boxers and jeans on the way out.
He turned back once to see if his mother would watch him go but she had her eyes closed. Joseph did face him though and just gave him a wink. Ryan ran from the room not even bothering to shut the door behind him.
When he got outside he just started walking. He was thoroughly confused, watching two people have sex while you spy on them had been exciting and fun. Then when he remembered that one of those people was his mom he felt sick.
His feet had carried him to a house he recognised. It was his supposed friend Joseph's house. On seeing this he planned to go inside and break something of Josephs hoping it would make him feel at least a little better. He let himself in the back door. They had been friends for so long that they didn't bother knocking when they visited each others houses.
As he was walking along the hall to Joseph's bedroom he heard a moan. It had come from Heathers room, Joseph's mother's room. He went over to the door for a closer listen and sure enough there it was again. She must be doing it herself as Joseph's father's car wasn't in the driveway.
Ryan could feel his dick start to respond again and wondered could he risk having a wank outside the door. He looked up and down the hall just to make sure and then took his dick out. He hadn't anything soft to help him this time but he was content just using his hand.
The moaning seemed to have stopped so he pushed his ear against the door to try to hear better. As soon as he did this the door flew open leaving him sprawled on the ground. He turned around so his dick wasn't touching the floor. He noticed a pair of legs first and he followed those up. They ended in a shaved pussy with only a few stray blonde hairs sticking out. His eyes continued up to her breasts, there weren't as large as his mothers but respectable nonetheless.
When he finally looked at her face, he saw that she was pissed. He couldn't help moving his eyes over her body taking in as much detail as he could in case this was the last time he saw Joseph's mom naked. This would go some way towards making them even but there would still be a ways to go.
"Ryan, what were you doing outside my door with your pants down, as if I can't guess," Heather asked crossly.
"I'm really really sorry Heather it just kind of happened, I heard you moaning and I couldn't help myself," he managed to stammer back.