The Bet

Everybody has a friend who is fit, fun to be with. Mark Hill and I (Bob Trip) have one Jason Smith. The three of have been friends for as far back as I can remember. All three of us turned 18 over the summer between our junior year and senior year of High School. Mark and I go to the same High School while Jason goes to the school across town.

Jason only lives four blocks from my house but the school district divides the two schools the next block over from my house. We normally hang out at my house because Mark and Jason think my mom is a MILF. They are always hoping to catch a glimpse of my mom and her three sexy friends.

Unfortunately, my mom (Kim Trip) and her friends are teachers at the same school that Mark and I attend. This year we will have all four of them as our teachers. Thank goodness only a few people know she is my mother. Mark and Jason are infatuated with my Mom and her friends. Mark and Jason are always trying to figure a way out to see my mom naked, they haven't found one yet, but they keep trying. I have to admit that she is gorgeous.

Guess I should describe the guys first. The girls at school all say Mark is a handsome dude and is very buff. He's a couple inches over six feet with a well-toned body from working out regularly. He has dark wavy hair, pronounce cheekbones, and green eyes that women seem to love looking at.

Jason is also over six feet tall with a rugged look that girls seem to like. He has jet black hair, piercing blue eyes, and a squared-off chin. He has great charisma and uses sheer aggression when he wants something. He seems to have the skill to be able to talk people into doing whatever he wants.

I'm a little nerdy but don't look like one. I am shorter than the other two only five feet and nine inches tall but I'm in pretty good shape. I have a six pack from working out with Mark. I have brown hair and brown eyes.

The guys were over at the house when Jason said, "Hey, you think your mom will finally make a bet with us over the two schools football game?"

"You know my mom won't make a bet with us. She even told us that before." I replied

"I know she that, but she said it was because we weren't adults yet. But now the three of us are 18. I'm going to ask her next time I see her."

"What are you planning on betting Jason?" Mark added.

"Guess I need to figure that out before I ask."

My mom and her friends are always betting someone on the game between the two high schools in town. My dad always tells her one day she will make a bet she will regret. Sometimes I think my mom has a gambling problem when it came to betting on the schools. You see the football game was a big deal in our town and betting on the outcome of the game is a regular thing in our town.

My mom and her friends always bet as a group and always find someone from the other school to bet with. Usually it's small stakes, a case of beer, a bottle of wine, do, something embarrassing that sort of thing. Every year Jason has tried to make a bet with them.

They kept telling him not until he was an adult. Well in Jason mind he's now 18 and legally he is an adult. Plus, he can barely keep his desire for my mom hidden. I know my mom knows that Jason has a big crush on her. I've seen her flirting with him and she has even prick teased him from time to time. Jason has told me she is just a big tease and one day he going to fuck her. I always laughed and told him in his dreams.

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A few days later Mark and I were up in my room playing on the x-box when I heard the doorbell ring. I didn't pay much attend to it as my mom and her friends were down stairs playing cards. I heard my mom loudly say, "Hey, Jason why don't you and your friend come on in. Bob and Mark are up in his room."

When Jason didn't come to the room right away I went to see what was taking him so long. As I got to the top of the stairs I see him with another guy whose name is Joe, he's a friend of from his school and hangs out with us from time to time. Joe seemed like a nice enough guy. They were over by the table where the women were playing cards talking with them in low voices. When Jason was done saying something the women all laughed.

"Jason we still can't make a bet with you guys. Bob and Mark are still in school plus we have them both in our classes this year. You and Joe may be 18 but you're still in school too." I heard my mom tell the two of them.

"That may all be true Mrs. Trip. But I can guarantee that none of us would tell a soul." Jason said with a smile.

"Hmm, let's say we took that bet. What would we be betting?" Mrs. Carr asked.

Jason got real quiet looked around to make sure no one else was around, leaned into the table and whispered something.

"OH, MY!!" shouted Mrs. Butler.

"Well guess you really do think of yourself as an adult now Jason." mom said.

"Ladies, I know you haven't found anyone to bet with you yet this year. This year the big game is our last game of the year and is scheduled for the first Saturday in November. So, think about my offer. I know your school in the past has always won, but not this year. I think you're too scared to bet with us because you know this year, you're going to lose, and I understand." Jason said with a smile and before they could say another word he was off and headed up to my room.

"Hey dude, what did you say to them?" I asked Jason as he got up the stairs.

He had a big smile on his face, "I told you I was going to make a bet with them and I gave them an option to bet us." Jason said with a smile.

"So, what was the bet asshole?" I asked

"I bet them that if my school beat your school that the four of them would have to take their clothes off and hang around in the nude for a few hours with us. And if we lose, we would do the same." Jason said with a smile.

"Really, our school always wins. So we're going to have to strip for them?" I said

"Not this year. Your team was mostly seniors last year and our team was mostly juniors. We almost beat you last year. This year we will win, I have a gut feeling." He said.

"Of course we'll add more to the bet when they make it." Joe added. Joe was about the same size as me and he seemed like a nice enough guy but he could be a real asshole from time to time, I've seen him bully people a few times.

Mark was listening in and he asked, "Do you think they will make the bet?"

"You know they have to make a bet every year on the game, and so far they don't have anyone who is willing to bet them. So I'm 90% sure they will take it because they have to bet on the game." Jason said with a smirk.

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Guess its time to tell you a about the women. All four of them teach at the same school that Mark and I attend. They have become very close friends over the years. About ten years ago my mom started making bets on the outcome of the football games between the two schools. It was about three years ago when the four women got together as a group to make the bets on the two schools.

They always find a group of teachers from the other school to make a bet with them. This year they seem to be finding it hard to fine a group willing to lose. Jason was hoping to make the bet with them because he knows for some reason, they need to make a bet just every year. He was hoping they wouldn't find anyone else.

Starting off with my mom Kim Trip, she is thirty-nine and she tries to go to the gym at least four days a week with her friends. She wasn't just Jason's fantasy; men are always glancing in her direction. A lot of the men when they think no one is around I have heard a few of them hitting on her.

Mom looked her age, but she was a hot MILF, if I don't say myself. She 5'5", 135 pounds, with black hair which hangs just past her shoulders, sexy hazel eyes. Her exercise has given her a very well-tone legs and a great narrow waist with just a little belly which adds to her sexiness. She would disagree with you as she always complained that, no matter how much she worked out, she just couldn't get her stomach flat.

Jason, Mark, and even Joe always talk about her great rack and what they would love to do to them. I know I like watching them bounce as she walks. Plus, her ass is round and firm, which sways as she walks I love to watching her walk coming or going.

I can see why my friends admire her. She has a frame that men love to admire. I knew other men want to be close to her, I'd seen them trying to cop a feel during our backyard parties. Mom does a great job at keeping them all at bay. Thank goodness my Dad not the jealous kind of guy or there would be a few fist fights at these parties.

Wendy Carr is nine years younger than my mom. She is also married and had two young kids. All of my friends think she is one hot MILF teacher. To top off her sex appeal, her long, wavy blond hair falls down her back, past her shoulder blades.

She stands about five foot and five inches with a very impressive figure. She is a full, beautiful woman; there is no fat on her that one could see. I would say she is built like a brick house. At school, she always wears a dress or skirt which shows off her long, fit muscular legs.

Particularly eye-catching is her cleavage. It's hard some days to pay attention in class because of her impressive breasts. In school I'm in one of her classes, and can't help but have fantasies about being with her.

Sarah Butler is about 12 years younger than my mom with two little kids. She still hadn't lost all the weight after having her last kid, even though she works out with my mom. She has a very cute face and I enjoy looking at her rack.

Jan Parks is also nine years younger than my mom. She is married with two young kids also. She has long red hair, normally tied up in a ponytail at school. She seems to also wear dresses or pencil skirts that showed off her hot figure, she is always friendly with me and my friends. I find myself going out of my way to talk with her and she seems to clearly enjoy our talks.

My Dad's name is Randy and is a very successful businessman. Unfortunately, he has to go out of town on business from time to time. He is also in great shape as he tries to go to the gym as often as he can.

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Since Jason has challenged the ladies to a bet he has been talking with them every time he sees them; sometimes as a group and sometimes by themselves. The guys were over at the house and I notice Jason talking with my mom and when he finished I asked him, "Hey, I notice you working your charm; you think you're going to get them to bet?"

Jason looked at me with a smile, "I think I almost have them. Time will tell, but yes, I do think they will make the bet."

That's when Mark jumps in, "I think you need a little incentive I'll give you $20 dollars if you're successful."

"Me too" I added.

"Deal" Jason said.

A few days later I was coming down the stairs to get something from the kitchen when I heard the ladies talking. It sounded like someone said bet. So, I decide to stay out of sight and listen in.

I heard Wendy talking, "We don't have anyone other than the boys to bet with this year."

Sarah, "Betting with the guys, well could get us into trouble. They are students even if they are 18. With the losers having to strip. I don't know it sounds like jail time to me."

"Have you all gotten old on me, where is your sense of adventure. I think we should do it. We just need to find a location where we could pay off the bet and not get caught." Jan said.

"I don't know, one of the guys is my son to top it off with. I wouldn't mind seeing the other three stripping for us though. Damn they all are young studs for sure." mom said.

"Don't forget how sexy they are." Wendy added.

"We would have to tell our husbands that we made a bet with them. But, we don't have to tell them what the stakes are." Sarah injected into the conversation.

"I know we can get into big trouble doing this. But what the hell that's what makes it so exciting." Jan added.

"I'm still nervous about Bob, he is my son." said mom.

"Look Kim, so what if he's your son, I think we all would like to see him nude too. You don't have to watch him. I agree it's dangerous but it's exciting as hell." Jan said.

"What if we lose?" ask Wendy.

"We all know we'll win. Our team always win the game. It's been years since we last lost. But just in case we lose we have to be willing to pay off the bet. Just like we would expect the boys to pay off." mom said.

"Jason is very convincing. I think we need to think about it some more." Wendy said. All of the women murmured in agreement. I stop listening in and went back to my room.

About two weeks later my mom pulled me off to the side where dad couldn't hear her, "Bob, I have to ask, you don't mind stripping in front of your mom and her friends do you?" She asks me with a very serious look on her face.

"Since we don't know the outcome of the game it might be you stripping in front of me and my friends. I'll take my chances. If we lose yes I'll do it because as dad always says a bet is a bet and you better pay it off." was my answer to her.

"You know my friends and I always make a bet and so far, there is no one, other than you guys who want to bet with us. I'll have to think about it and talk over with the girls." With that she left. I smiled as I watched her walk away, her ass swaying and my cock rising.

I call Jason and told him what she said. He liked the fact that no one was willing to make a bet with them. He assured me that this year our school was going to lose. After that day Jason aggressively kept bugging the women. He was now even texting them daily using all of his charm.

It was about two weeks before game day when Jason said "they agreed to the bet. They want some rules though. Your mom wants to have a meet up with all of us guys and them tomorrow at your house."

"Guess I'm out $20 dollars." I laughed

The next day was Saturday and my dad was at the gym. We all sat around the table with the women on one side and us guys on the other. "No offense guys, but there is no way you are going to win. I just want to make sure you know that. If you want to back out now is the time." Mrs. Carr said. We all had to good laugh and got down to business of getting the rules made.

1st rule was easy - no one outside of our little group will know about this. We all agreed, we didn't need mom or any of the teachers getting into any kind of trouble.

2nd rule - no cameras or cell phones. Everyone nodded with that

3rd rule - stripping would be done one at a time. When the person was done stripping they would be told to move around, so each person on the winning team can get a good review their body. All discarded clothes will be put into a single laundry basket no one is allowed access until the bet is done.

4th rule - After all of the strippers are nude they will stay that way for three hours. During this time, the losers are not allowed to cover up or hide their assets. The losers have to move around the room so the non-strippers can review them during that time.

5th rule - The nude individuals will have to dance four dances with each of the winners.

6th rule - NO SEX. Some groping is ok and the person being groped can stop it at any time.

These were the rules we agreed to. Mrs. Parks typed them up and we all sign the agreement.

Then we discussed where this bet would be paid off. The women didn't want their husbands know about the bet. Even if they knew they didn't think their husbands would like four 18-year old young men stripping for their wives in their home. "We can do it at my place!" Jason said loudly

"What would you mom say Jason" Mrs. Carr said

"That's right you all don't know. When I turned 18 my parents had a room added above our garage. I have a good size gaming room, a little bed room and a small bathroom. It even has its own entrance from the back. It would be perfect." Jason said.

"What about your mom? Doesn't she come up to your room? You all know that she does not like me at all." My mom injected.

"Don't worry about my mom. She never comes up there when I have friends over. As I see it, it's the only place we have." Jason replied.

"Well I don't know, if she dislikes Kim so much, I'd hate to think what she would do if she saw us all entering your place." Mrs. Parks said.

"To me it sounds like the only place we pay off the bet no matter who wins." Mrs. Butler added.

"You ladies need to decide and let me know. I will need to clean the place up." Jason said.

"We'll talk about it and let you know soon." My mom said.

As our meeting was breaking up Jason said with a smirk on his face, "You ladies know you're going to lose and are just looking for a reason why not to strip for us."

Laughing Mrs. Parks said, "Don't you guys worry about that; since it's you four who will be doing the stripping." And with that the meeting was over.

A few days later my mom stopped me as I was coming into the house, "Bob the girls all agreed to let you guys strip for us at Jason's."

I laugh as I answer her, "I'll let Jason know you ladies have agreed to strip for us at his place." Mom giggled as she walked away from me.

I sent a text to Jason and I was very surprise at his replied. "I need you to set up some cameras ASAP."

I called him right away, when he answered. "You know we can't have cameras."

"I know, but if you can hide some cameras that only you and I know about, then we can have a recorded memory of the day." Jason said.

"I'll do it but I need to get into your place by myself. I don't want you to know where the cameras are. That way you won't be looking into them and smiling. Otherwise it's a no go" I demanded.

"Ok, how much time you need?"

"About three hours to make sure they are hidden well enough so nobody can find them."

"OK, how about this Saturday at Noon."

It was now a week from the big game and I was at Jason's hiding cameras and making sure they will send the video to my laptop. The game room area or the living room area (depends on what you what to call It.) was not as small as I thought. They had a two-car garage and most of the place was the game room area. I rearranged Jason's place to give the ladies a place to strip and where we could do our dancing.

As I was doing this I text Jason to make sure he knew what I was doing. I pushed his couch over to where we could sit and watch the women. I push his computer chair next to the couch. One of us will have to sit on it. I had more than enough cameras to make this work. Each camera had a battery which will last a year and was motion activated. As I placed each camera I made sure it sent a signal to my computer and recorded the area that I wanted it to record.

When I was done I said to myself why not put some cameras into Jason sleeping area. You never know what might happen, I wanted to cover all the bases. It took me the whole three hours to set everything up. I made sure I was the only one who could turn the cameras on with my computer. I made sure there was no lights coming from the cameras when they were on. Next big mission was to make sure that the cameras will transmit to my bedroom. I will have to check that when I got home.

When I got home I did a transmission check and everything working perfectly. I could see and record every inch of Jason place. I text Jason telling him it was go. Hopefully there will be no problems on bet pay off day.

As game day got closer the ladies would pick on us and we picked on them. The ladies were over at our house and Mrs. Carr yelled out to me, "We're gonna beat, you so bad! Can't wait to see you strip."

I laughed and cockily replied, "In your dreams lady, it will be you ladies who will be doing the stripping."

"Oh yeah right. I hear you're a dreamer." Mrs. Parks yelled back

Damn where were the guys for backup but I just smiled and answered, "you're just hoping your team will show."