A Bet with Big Bad John

I want to give thanks to gildedbutterflies for editing this story.

My name is Bob. I turned 18 a few months ago and will be graduating from High School in a month, and I have been accepted into college this fall. Dad and Mom have been on me to get a summer job so that I would have some spending money at school. This is why, when the local factory came to the High School looking for five 18 year old seniors to work this summer in their round robin job program, I was all in for it.

There were about 25 of us who put in an application for the program. They had all of us in a room as they explained the program to us. We would work in each department for about two weeks and after we were finished we would then work the rest of the summer in whichever department we did best in. Since there were so many of us interested in the program they were going to take several days to look over our applications and then let us know which five of us would get the opportunity to be part of the program.

My best friend Jake's Mom Mary was a floor manager at the shop, so I figured I would ask her if she could pull some strings to get my application through. So that evening I went over to see Jake. When his Mom got home and Jake informed her I wanted to talk with her, she came into the TV room where I was waiting.

"Hi Bob! Been a while since I have seen you. You've normally gone home before I get home from work. What is it you needed to talk to me about?"

"It's about the summer program at the company... I really want to get the position. I was hoping you might be able to help me out?"

"Well, I'm sure that you know we had 25 applicants for the program. I can talk to some of my supervisors, but I can't guarantee you will get the job. I'm a manager in Department A so we have high priority in the company. I'll see if I can help you out."

I thanked her and stayed for a while playing with Jake on the PS3. As I was getting ready to leave Jake's dad Jack came in from work.

"Hey Bob! I hear you're trying to get a job at Mary's workplace. Good luck!"

"Thank you, sir!" I said, packing up my things and going home.

About two weeks later I received a phone call informing me that I got the job and to report to the HR department at 7 AM the Monday after graduation. I called Mary that night and thanked her for putting a good word in for me.

I reported to the factory at 6:45 and was escorted into a room with a few large round tables, with four other guys sitting around one of the tables.

I knew all four of them. There was Dave Hill, Mike Valley, Jim Hay, and Big Bad John Smith. Dave, Jim and Mike were like me. We were not jocks but we were all in shape and around six feet tall, expect for Jim, he was about 5 feet 8 inches. Now Big Bad John was a big football and basketball jock and seemed to always have girls around him. According to rumor he has even dated some of the married women in our town.

He was a large guy about six feet five inches tall. He got his nickname from one of the girls he dated freshman year. She told everyone that he had a big cock and treated her badly, and after she broke up with him the girls that came after her had the same story. Personally, I thought that he was an overbearing ass hole.

They gave us each a bunch of paperwork to fill out. While filling out all the paperwork we sat there and made small talk, trying to get comfortable with the idea we were going to spend all summer working together. This is when I found out that we all got selected because we each knew someone who worked there.

Big Bad John started to brag that his father was one of the lead managers at the factory. Then Big Bad John boasted of his sexual conquests, attributing his success rate to the fact that he had a big cock and that's what all the women wanted. He went on to talk about how great he was and that he could fuck any woman that he had his eye on. He was going to see how many of the factory women he could add to his stable, as he called it, this summer.

I was getting annoyed with his talk and sat up a little straighter, "John I don't think you can get just any woman, maybe the easy lays but that's about it."

He just looked at me and started to laugh "Tell you what, if you think there is a woman in this factory I can't get you just let me know and I will prove you wrong."

I just sat there looking at him.

"I see you can't think of anyone, can you?" asked Big Bad John, smiling.

Then I spoke up "Okay. I know someone. Her name is Mary Jay and she is a manager in Department A and I know for a fact that she is happily married."

"So would you like to make a bet on this, shit head?"

"Sure would!! How about Two hundred dollars?"

Big Bad John looked at the other guys and asked "You guys want in also?"

They all shook their heads yes.

Then Mike spoke up "You're going to have to prove it with pictures or something. Plus you were saying that they will keep coming back for more and will do whatever you want them to do. So after you prove it, she then has to fuck all of us for you to win the bet. Then we will all know your not just photo shopping the pictures."

He started chuckling, making eye contact with all of us. "I'll do better than pictures, I'll have a video of me fucking her. As I told you they all will do what I want them to do just to keep getting this fine piece of meat. She will fuck you guys, I guarantee it. So I accept your terms to the bet. You each will pay me two hundred dollars after you have your turn with her."

Then looking at me "you can't warn her, got it?!"

"Got it" I answered.

"Now tell me what you know about her."

All the guys were now looking at me "Well I go over to her house a lot, Jake her son is my best friend. In my opinion she is gorgeous. She is an educated woman with a master's degree. I would say she is about 20 years older than me which makes her about 38 or 39 years old, 5'5", weighs about 135 pounds, and 36 C or D cup which must be the most incredible breasts. I have never seen them bare but I have seen her in a swim suit. She is coming up on her 20 year anniversary and is happily married. She has three children. Jake is 18 and her daughters are 16 and 13. As far as I know she has never cheated on her husband. She works out six days a week, and she is in good shape. She has great abs. In the summer she always lays out in the sun and I love to look at her sexy tan legs that lead up to a great ass. She has a very friendly personality always brings smiles and laughter to those around her. I know she's used to men noticing her and from time to time, but she always cuts them down or brushes them away. She is one of those people who would give you her last dollar and not ask for you to pay it back. Her reputation is being a straight shooter. Are there any other questions?"

"Wow, you seem to know her well. Guess you have spent a lot of time over at her house. No more questions, but I will tell you this - she won't brush me off." said Big Bad John laughing.

Just then a nice looking young woman walked into the room and gathered all of our paper work up. She then explained to us what we would be doing during our time with the company. She explained to us our schedule and which departments we would work in first. Then she gave us a tour of the plant. Big Bad John was being as obnoxious as he could be with her.

I looked at him, annoyed "Hey stop being rude man."

He smiled at me "They have to put up with me. My old man told them to let me be and they know if they piss me off they might lose their job. So you just be a good kid and leave me alone."

As we went though department A I was waiting for Mary to come around so I could point her out to the guys. When she came out of her office everyone took a good long look at her.

She walked over to us and said "Hi, I'm Mrs. Jay and I'm in charge of this department. I hope I get to know all of you very well."

Big Bad snickered. "I'm sure we will get to know each other very well."

Looking at John, Mary smiled "Oh you must be Mr. Smith's son, glad to meet you." She didn't wait for him to reply and just walked away.

"She's going to hear about being rude to me. Dad will have a little talk with her later today I'm sure of it." John said with a snarl on his face.

After the tour we took lunch in the company café, John didn't hang around with us and took off. I assumed he was going to eat lunch with his Dad.

Mike looked at me "So Bob who do you think will win the bet?"

"I think we will win, come on he's an ass hole and she is a good woman. No way would she cheat on Jack. I don't think he will be able to come through"

"Wait a minute you two. I've seen him with older women before, I wouldn't count my money before the end of summer." said Dave."

"We should have given him a time limit on this bet. I tell you this though Bob, she is gorgeous." Jim putting his two cents in.

"I'm telling you guys I don't think he will have a chance in hell with her."

Just then John rejoined us. "Hope you guys don't mind but I told my Dad about the bet and he just laughed. He don't think I will be able to get her either and joined in the bet also. Then I told him how he could help.

He was all in for helping but he said he won't sleep with her because she works for him, but would love to see the video. I told my Dad about her being rude. I don't think he believed me but he is going to have a talk with her this afternoon."

"We don't mind your Dad helping but if he doesn't think you can you better make sure you have our money ready by the end of summer." Mike butted in.

Laughing John continued. "You're all going to be paying me and before summer is up."

After lunch our afternoon was filled with safety classes.

Just about time for us to head for home I saw Mary walk into the classroom and went right up to the instructor. I heard her ask to speak with John Smith.

The instructor pointed over to where we were all sitting. Mary walked over and said " Sorry if I seemed rude when you were going through my department."

Mike answer "We didn't think you were rude Mrs. Jay."

"Maybe she wasn't rude to you guys but she sure was to me!" shouted John.

Mary looked at John. "I would like to apologize to you for being rude to you."

John looking Mary up and down like a lion sizes up a piece of meat. Mary said " Now I think you're being rude by looking at me that way."

John smiled "Guess I need to talk with my Dad again."

Mary then said "Just come over here and talk to me about this. We don't need them all listening in."

"Sure, lets move over there."

They moved a few feet away but from where we were sitting we could still hear everything they were saying.

"I want to apologize for my actions and will go out of my way to be nice to you. I just would like for you to know that I do not like being looked at like that."

"Damn right you're sorry, and you better be nice or I will report you again to my Dad. I was just looking at you and I will look at you from time to time as long as I work here. Now I guess you can tell my Dad that you don't like how I look at you, but until he says something to me I will look at you any way I please."

"I still want to make sure you understand that I'm sorry for being rude to you earlier. With that I hope you enjoy working here." and she walked away.

John walked back over to us and said "She is going to be fun to mess with. I'm sorry you guys are going to lose your bet, but you will get to fuck her at least."

The next week we started working in department B and before the week was out Big Bad John had a date with one of the women who worked there. He had to brag to us about it. We really didn't take too much stock into it as he never showed any pictures or shared her with any of us. Then we found out that we would be moving a week early into department A, and instead of the two weeks we were to be spending on that shift it will now be three weeks. We all knew John's Dad was going to give his son an extra week to work on Mary.

That weekend I went over to see Jake. I wanted to see if Mary would say anything about John. Jake was glad to see me, he was bored and wanted someone to hang out with.

"Let's play on the PS3!"

"Sure, but I can't stay long.. have to help my Dad around the house." I told Jake.

About an hour later Mary walked in. "Bob can I talk with you for a moment?"

"Sure, Jake, you take this round."

Mary and I walked to the other side of the room "What do you think of John Smith?"

"I think he is an ass hole and he uses his Dad's name to get away with things."

"I agree, I got my ass handed to me the other day by Mr. Smith for being rude to his son. Then I got it again the next day. Guess I need to be careful of what I say around him for the next three weeks when you guys are in my department."

"Well he does like to talk about himself a lot."

"I heard some stories about him from some of the women in department B. They all seem to like him and say nothing but good things about him. A few of them even hung out with him after work. Maybe John and I just got off on the wrong foot, guess we will see next week. The girls were also talking about how he got his nick name."

"I heard the stories, not sure if they are true or not if you're asking."

"No I'm not asking, just talking and I don't want to find out either. I'm sure someone will confirm it."

"Well I need to run, Dad needs help with something in the back yard. See you at work next week." With that I left.

Monday I couldn't wait to get to work, I thought it would just be great working in Mary's department. At last Monday came and we all reported to the HR office to be transferred to department A. When we got their we were shown what we needed to do for the day. I saw Mary in her office looking at her computer, she was wearing one of her normal pant suits, but to me she still looked as hot as hell.

Mr. Smith walked into the department and walked towards Mary's office. He looked at his son and gave him an evil smile. As he entered Mary's office you could tell from his face he was not being nice to her. She just kept shaking her head yes. Then he departed. Shortly after he left Mary walked out of her office. Instead of heading straight over to us, she walked around talking with everyone. John leaned over to me and whispered, "stay quiet and just listen when she gets to us."

As she walked around checking on everyone she finally made it over to John and me. "Hope everyone had a good weekend. Is everything going okay this morning?"

"I had a great weekend, all I could do was to think about working with you this week. Hope we will be able to work close this week," John answered.

"Well I hope I have the time to work with you also John. I think you and I got off on the wrong foot two weeks ago."

"I think you're right about that. How about you letting me take you to lunch to show you that I'm really not a bad guy?"

"Thank you for the offer but I really can't go to lunch with the people who work for me."

"Come on now you don't want me to tell good old Dad you're being rude on my first day in your department now do you?"

"Okay, guess we can make it a working lunch and your father won't have to worry about it."

"Good I have a great place where we can eat and maybe bond. Then I can tell Dad we are working out our personal issues, see you at lunch."

Mary just smiled at me as she walked back to her office.

John laughing "Might be a long lunch. Don't worry Bob, if anything happens it will be on video. I'm going to take her to my apartment for lunch. Dad got me a small apartment close to here so that I can practice being on my own without really being on my own."

"You lucky dog you, well I hope nothing happens because I want to win the bet. But if it does, guess I win either way."

It was lunch time and I watch Mary and John depart for lunch. I went to the company café and had lunch with Dave, Jim and Mike.

"Where is John today?" Asked Mike.

"He got Mrs. Jay to have lunch with him." I responded.

"Looks like we will see if he is full of shit soon" added Jim.

Dave smiled "Well to be honest I hope he is telling the truth. I would love to fuck Mrs. Jay and so would all you guys."

I went back to work after lunch but John and Mary didn't show until a couple of hours later. John rejoined me and smiled. He didn't say a word about lunch.

The next day Mary showed up for work wearing a white blouse with the top two buttons undone and a black skirt. She also had nylons on, and three inch heels.

She walked right over to John. "Thanks for the great lunch yesterday sir"

"No problem, we can do lunch again today."

"That would be great sir, but I do have to catch up on my work from yesterday."

John a little demanding said " Listen, you should have stayed late yesterday and caught up with your work. Guess you need to call your hubby and let him know you will be working late the rest of this week because of the work load. Don't want Dad to find out you're falling behind on work. Plus you're going to be working this Saturday you understand?"

Mary just nodded her head "Yes sir I understand about working this weekend, I'll make sure my husband knows." then headed off to her office. There I sat with my mouth wide open. Then I spoke up "Things have sure have changed between you two!"

John Chuckling " You're right about that. Friday night you guys come to my place. I have a video for you guys to watch."

"No way, already?"

"Yes way, hopefully by this weekend I will have her under my total control where she will fuck you guys and I win my bet'"

"How did you do it?"

"Friday I will show you the tape, but you will only know part of the story. Can't tell you everything."

It was lunch time again and John left with Mary. About an hour later Mary finally returned from lunch, she looked like she was thinking hard about something. I ask John "what happen?"

"I wanted her to show you guys some cleavage and she didn't want to do it, specially with you around, Bob. So I slapped her on each cheek and I told her if she wanted more of me she is going to have to do as she is told, even with you around. She is starting to understand that I'm in control and won't take no for an answer. You'll see Friday."

"I'm still a little lost here, why is she starting to do everything you want?"

"You will understand after you watch the video."

That night I went over to see Jake. We were in the rec-room watching a baseball game. I heard Mary and Jack having an argument, but I couldn't hear much of it. Then suddenly Mary was shouting at Jack " Look I know I can quit but we need the money to make sure Jake can go to college. So if Mr. Smith wants me to be nice to his bully little ass of a son, which is going to make me work extra to stay on time with my work then I guess I will. It's only for the three weeks he is in my department, then everything will get back to normal."

That was all I heard from the two. After that I left. The next day was Wednesday, and at work the five of us were working together and I told John what I heard. He got a big smile on his face.

Then I saw Mary and again she had on another skirt and blouse with a few buttons undone.and was looking really good. She walked over to the five of us. With her back to the rest of the department she bent over and gave us a great view of her cleavage. "Hope you guys are enjoying working here and are learning a lot."

John looked at her and spoke in a low demanding voice "Look bitch we're happy about seeing your bra but we want to see some tit. So reach up and pull your bra off your tits so we can get a good look."

Mary looked at him and was about to say something but instead look around to see if anyone was looking. When see saw everyone else was busy she reached up and unbuttoned another button and pulled her bra off her boobs.