0 comments/ 151516 views/ 117 favorites A Bet with Big Bad John By: Thecsm 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. A Bet with Big Bad John "Wow" was all I could say. Then John again "Bitch now bounce them for us! No one is looking over here." "Yes Sir." Mary then did as told. She shook her chest and her tits bounced around a little. "Look slut you're pissing me off. I want my friends to see those sexy boobs bouncing. Now!" "Yes sir, I'm bouncing them." Mary softly replied. John looking pissed off with a voice a little louder than before and with a very commanding voice "Bounce them and don't stop until I tell you!" Mary looking around to make sure no one was looking started to really bounce her tits. She even jumped up and down once to let them bounce real good. I looked at her face and she was smiling, I think she was enjoying being humiliated by John. Chuckling John then said. "Okay bitch now fix yourself and get to work and be ready for lunch by 11." This time Mary didn't say a word and did as she was told. "Looks like you have her under your control." Mike said "You got that right she is coming along a lot faster then I had expected. I think she enjoys being told what to do. Friday be at my place around 7 and you're going to see some very good videos." John and Mary went to lunch but didn't come back before we all left for the day. Thursday and Friday Mary did her rounds and with a smile she would give us a show as long as no one else was watching. If someone was she would come back later but we still got our show. I couldn't wait for the night's entertainment at John's. When I arrived at John's I knocked at the door and Mike opened it. "I see someone is anxious to see the video! Grab a beer, we have been waiting on you. Your the last one to get here. Maybe now we can get on with the show." I grabbed a beer and saw some pizza so I picked up a slice and then jumped into the only seat that wasn't taken. "Before I start the show I want you all to know that I have cut a lot out of tonight's entertainment. I have the whole thing here on flash drives which I made for each of you to watch yourself. Now you can't show anyone else this because I'm in it and I'm not giving you my permission. Plus we do not want to ruin Mrs. Jay's reputation. Understand guys?" We all laughed and agreed with his request. John had a 50 inch screen TV and when the show started it was like being in the room with the two. John was first to speak "Mary have a seat. Since were here to bond I hope you will be 100% honest with me. I would like to report to my Dad that our lunch meeting was a success." "Yes I will be honest. As long as you are 100% honest also." "Good deal. First question, how old are you?" "I'm 38 and will be 39 in two months, and how old are you?" I'm 18 and will be 19 in five months. I understand you had lunch with Sue from department B and were asking questions about me." "Yes I did. Sue and I are friends and I wanted her opinion about you. She told me she thought you were a great guy once you got past your bossiness, and she has had lunch and dinner with you. " "Did she tell you how I got my nickname?" "Oh yes she did and I don't believe the big part, the bad part I see in you." "I've seen you looking at my crotch all day. Guess you're trying to figure out if it's true. Well I could put that to rest and let you see it if you want." "No, I'm a married women and that just wouldn't be right, plus I'm your boss at least for the next 3 weeks. What are you doing?" "I'm pulling down my pants, I don't care if you look. I'll even let you touch it, bitch. I don't give a shit if you're married or my boss." "First I don't like being called a bitch, and I will not cheat on my husband, especially with you." John wasn't listening to Mary and down came his pants and then his underwear and out popped his huge thing. Damn it was quite a cock, it looked more like a fat night stick. There he stood in front of Marry and neither one of them said a word. He moved closer to her until his dick was about six inches from her face. Then John in a rough controlling voice "Would you like to touch him? You've been imaging what it looks like all day, now you see it. Go on, touch it and you can help it grow to its full size." Mary couldn't keep her eyes from looking between his legs. She looked up at him and was smiling. Her hand made a move toward him, but she jerked it back. "No, I don't want to touch you, I'm married and you need to cover yourself." We could hear John laughing at her. He knew she was fascinated with the size of his monster manhood. Without saying a word he sat down on the sofa next to her, and casually took the hand with her wedding band into his. Then he moved her hand over his crotch and lowered it onto his dick. His cock was growing! It started to stick straight up, it must have been 10 or 12 inches long. He removed his hand as Mary starting to move her hand around his cock, and over it. Then she started to move her hand up and down his shaft. Here I was watching my best friend's mom rub a guy's cock, and damn, this was one hell of a big turn on for me. "Use your other hand also, see how much bigger it can get." Mary started to move both hands up and down on his staff. After a few minutes of Mary giving him a hand job he reached over and put his hand on the back of her head and slowly started to push her head toward his monster dick! She didn't resist him at all her lips were now touching the head! Weakly Mary whimpered "We need to stop I don't even do this for my husband." John just kept his hand on the back of her head pressing her mouth down against his dick. She struggled a little, but in the end she just opened her mouth, and slowly put his cock into it. Her mouth was stretched wide, as the head went inside, his hand was still on the back of her head and now moving her up and down faster on his rod. She gagged at one point but he just kept moving her head, fucking her mouth. After a few minutes you could see him spurting gobs of cum into her mouth and throat. She tried to swallow, but gagged. She couldn't' swallow enough, and it ran out of her mouth and down her chin onto Johns lap, she moved her hands to catch what was dripping from her mouth. She then moved her hands to her mouth and licked all the cum from them. Then John spoke "Was that the first time you ever ate cum?" "No, I just don't do it often" was all Mary said. "Now Mary I know you are curious, and will never be satisfied until you know the answer." "The answer to what?" "Can you handle my cock?" Mary just looked at him with humiliation. John then order her to remove her clothes and Mary obeyed. I couldn't believe that she had become so submissive so fast. Damn, she looked even better with out her clothes on. Her tits sagged a little but not much. Her pussy was trimmed neatly. Then I heard John shout "Get up slut." Mary stood up, he turned her around, grabbed her hands, pulled them behind her, and doubled her over the back of the sofa. Then he commanded "Beg for it whore." "Please fuck me, You're right I want it! Damn you fuck me, fuck me now!" I could hardly believe it, but her words were not missed by any of us watching the video Then John took his cock and pushed it roughly into her pussy. You could tell there was no love or tenderness here, just a man fucking this submissive woman as hard as he could. You could hear her moaning in sheer pleasure. "You like a good fucking, don't you cunt?" All she did was moan louder. "That's a good little whore. Tell me how you like it." She was quivering and replied, "You feel soooo good please don't stop." He started pushing into her faster and harder. "Beg for it bitch!" She instantly replied, "Give it to me! Give it to your boss, I'm cumming!" He then grabbed her hair and grunted roughly as he continued pounding with no mercy. When John was almost finished he pulled his cock out and shot his load all over her back. "Not bad for the first time slut. You'll get better, won't you? If you want more of this cock, make sure tomorrow you wear a blouse and skirt to work. You do want to get fucked again, don't you slut?" "I'll do anything you want if you'll fuck me again!" "Good tomorrow you will make a doctors appointment and get on the pill if you are not already on it. I don't want to get you pregnant. Don't forget how I want you to dress tomorrow. Make sure a few of the buttons on that blouse are undone. Make sure your pussy is shaved next time bitch. You are now my personal fuck slut aren't you?" "Yes." was all Mary said. "Whore, you are going to start calling me sir from now on do you understand?" "Yes sir." "Good, I'll let Dad know we had a very successful lunch. He will be happy to hear that. Now go fix us something to eat, bitch." That's where the video ended. I just couldn't believe that I just watched my best friend's Mom being used as a sex toy by this kid. "If you guys still want to fuck her tomorrow you all be here around 10 AM and don't come early. Mary will already be here waiting for you and don't forget my money." As we departed from John's apartment Jim spoke up "Wow, do you believe that?" Mike chuckling "I can't wait until tomorrow. She sure wasn't acting like a goody two shoes today and now we're all going to fuck the hell out of her." "Guess she is just a slut. I'm going to make sure I have some fun tomorrow." Dave said. "I'm with you guys, tomorrow will be a fun day." all I could come up with. It was rough trying to get any sleep that night, so I got up and watch the disk drive that John gave us. It had about 8 hours of her and him fucking and sucking. Whenever she didn't do what he told her he would smack her hard, but she seemed to love the abuse. Through the film I saw her go from a woman in control to a very submissive woman. When it was time to return to John's, I was early just like everyone else. We waited outside until 10 and then as a group we went to his door and knocked. Big John opened the door and didn't say anything as we walked in. John eyed us sarcastically. "Glad to see all four of you guys show up. I wasn't sure if you would be here or not." Dave laughed. "We wouldn't miss today for anything." Then we saw Mary standing there wearing a blouse with jeans and pumps on her feet. She said "Good morning boys. I see that I have four young men to entertain today. John has guaranteed me that my husband and son will never find out about this." You could see the humiliation of having to submit to us in her eyes. We all said "Good morning." Then I add "We all promise not to tell Mr. Jay or Jake anything about what happens here." Everyone shook their heads in agreement. "Okay guys here is how it going to work. I'm going to take off for a few hours and when I come back time is up. The four of you can decide who is first and who is last. Just leave your money on the table there before you take off. Make sure you have fun, and she will do whatever you guys want. Stay the fuck out of my room." None of us said a word until after John left. I caught Mary giving me the evil eye, wondering why I was here. Jim taking charge said "I think she needs to I strip standing on the coffee table." "I have a name!" Mary said. Dave nearly shouted, "well were not going to call you Mrs. Jay today, so why don't you just do as you're told, no matter what we call you." Mary looked over to me for help but I didn't give it to her. She knew she was defeated and stepped up onto table. She took off her pumps first and tossed them to the side. She took a deep breath as she started to pull down her jeans and stepped out of them. Next she undid the buttons on her blouse from bottom to top, and her blouse soon joined her jeans and pumps on the floor. We all knew it was going to be either her bra or panties next. When she arched forward and reached behind her we knew for sure the bra was next. She began pulling apart the hooks on the bra. She let her bra fall forward and off her shoulders, her tits bounced as she toss it over with the rest of her garments. All eyes were on Mary and her boobs looked great. Now she hooked her thumbs in the waist band of her panties and pulled them down and off, balled them up and tossed them. Her pussy was now completely shaved and you could tell she had some large cunt lips. I held my hand up and helped her off the table. There was some awkwardness at that point among us. As Mary stood there fully nude, her nipples starting to stand out to their full length. No one seemed to quite know how we were to proceed from here. Finally Mike said "So, who goes first?" Jim taking charge said "I want to go last." Then Dave said "I would love to go first. I need to be somewhere." No one seem to mind. Mike jumped in "I'm 2nd." Which left me 3rd. I didn't mind because I was planning on staying until everyone was finished. Dave took all his clothes off then walked over to Mary, looking her up and down and said, "get on your knees. I want a blow job." Without question Mary got to her knees and took Dave's short fat penis into her mouth. Dave had a look of surprise on his face when she complied. He was amazed that a woman at least 20 years older than him dropped to her knees and was giving him a blow job without question. After maybe five or seven minutes Dave seemed to be ready to shoot his load. He suddenly twisted his fingers tightly into her hair. He held her head motionless as he rammed his cock in and out of her mouth. He stopped and held the head of his cock just inside of her mouth then he groaned has he shot his semen in to the back of her throat and she gagged as he filled up her mouth. She was swallowing but some dribbled out and down to the floor. Dave's grip on her hair was gone as he withdrew. Without warning he moved his hand under her chin, turning her face up to his, he was laughing at her upturned face and said, " you're one hell of a little cock sucker, boss," You could see in Mary's face she was feeling humiliated. Dave was still hard and pushed her on the couch pulling up her legs and slamming his short fat cock into her sweet pussy. He fucked her hard for about 15 minutes before he exploded inside of her. , He jumped right up and said "Sorry but I have to run, I will remember today for a long time." with that he got dressed, put his money on the table, and out the door he went. Mary smiled "Four little boys and now only three left." I had a feeling Mary was really enjoying being fucked in front of us all. Mike already had his clothes off and as he walked over to Mary he was putting on a condom. He jumped on the sofa, rolling over to his back. His cock was slightly longer then Dave's, but just as fat and pointing up at the ceiling. Without saying a word Mary just went over and straddled his hips, taking his cock in her hand and guiding it into her dripping pussy. "That feels great," he said with a smile on his face. She began to rock slowly back and forth on his dick, Mike's hands were happily kneading her breasts. He then grabbed one of her breasts and started sucking it, biting it hard. Mary didn't seemed to mind the rough treatment on her boobs. After he shot his load he was finished with her, he got up and dressed quickly. Mary smiled "Four little boys and now only two left." She quickly got up for a bathroom break as Mike put his money on the table and left. As Mary was walking out of the bathroom I said, "Looks like it's my turn now. I've always fantasized about this now get over here." "Bob you know you don't have to do this. I'm your best friend's Mother..." "I know I don't have to do this but like I said I've always fantasized about this, therefore I'm going to have some fun with you." With that said Mary came to me. I pushed her down to her knees and I roughly grabbed her head and as I took out my cock I instantly shoved into her mouth. She reached out and grabbed me by the back of my thighs and began to bob her head up and down on my cock. She was giving me a great blow job. I then shoved my cock all the way down her throat causing her to choke. I held it there, gently gyrating my hips for a moment, and fucked her mouth hard. After a few minutes I shot my load into her mouth. She gagged a little and swallowed as much as she could. I just couldn't get over my friend's Mom giving me a blow job and I was in heaven from watching her eat most of my cum. Looking at her I commanded "Now move over to the couch, bitch!" Mary looked at me "Don't call me a bitch Bob, please, not you." "I'll think about it," I said, a smile on my face. She then slowly moved to the sofa and I grabbed her legs, pushing them up into the air. In one sudden movement I rammed my hard, wet cock into her sweet cunt. "Damn you feel good!" I cried, beginning to pound her relentlessly. I loved seeing this strong woman being so submissive, and I was fucking her as hard as I could, our bodies making slapping noises as we rammed together, my balls slapping against her bare ass as my fingers crept between her legs, finding the swollen button of her clit and beginning to rub in swift circles, "I'm cumming!!" the sexy mother beneath me cried out, her body twitching as her sexy pussy began to spasm and clench around me. Jim was smiling as he egged us on. "That's it Bob. Fuck her! she's cumming all over your cock. Do it to the slut, fuck her!" Grinning I yelled out, "It's so damn good. This cunt is so fucking wet! This is so fucking hot!" I continue my pounding with no mercy, fucking Mary almost to another orgasm. Then I stopped, leaving her gasping in frustration, teasing her, bring her to the point of climax without letting her go over, my skilled fingers swirling figure eights and pressing circles onto her hard clit as my cock gently edged itself back in to the hilt, then out again, a gentle fucking, a rocking motion, sending her into convulsions. "Please let me cum Bob!!" "Beg for it, Mary." "Please." "Please what?" "Please Bob, I need to cum. I need to cum all over your sexy young cock, I need to cum for you!" I smiled and slammed into her with everything I had, pounding her sexy pussy with my cock. I bent low over her, twisting my fingers into her hair and pulling her head to the side, whispering in her ear. "Cum for me, my sexy little cum slut. I want to hear you scream my name." In that instant she was trembling and started moaning, nearly screaming. Her legs tightened around me, her fingers clawing at my back as I continued punishing her pussy, my name coming from her delicate, parted lips in an orgasmic chant. I thrust in one more before I felt the orgasm building in my balls, and I pulled out of her sweet pussy just in time to cum all over her bouncing, soft tits. "Please Bob don't let Jake find out about this." Mary begged as her cunt spasm one last time from the pleasure of all the fucking. "I'll keep my mouth shut if I can have a blow job or a fuck from time to time.." I whispered, leaning forward to kiss her hard on the lips, something I had fantasized about for years, my tongue tangling with hers for a moment before we broke apart. Mary didn't answer and I picked up my clothes, ready to get dressed. "Guess you're staying to watch the last of the show?" Jim asked Chuckling I replied "Yep, that's the plan. You watched me and I have nowhere to be." Mary looked at Jim and smiled sexily, "Four little boys and now only one left." Jim has never been a really big guy, so when he undressed it was shock to find out he had a very large cock. Not as big as John's but not that much shorter. He ordered Mary to get on her knees in front of him. He was much more demanding the rest of us, he was more like John in the way he was talking to Mary. He grabbed a handful of hair then pulled hard and pushed his staff into her mouth with great force. Then started to face fuck her hard, she was gagging a little on his cock. He didn't last too long before his semen gushed from his cock and into her mouth, she swallowed as quickly and as much as she could. After a while he pulled her head off his cock and got up. A Bet with Big Bad John Mary was standing in front of him again, he told her to turn around and bend over. Mary turned around and backed up to him, and his cock pressed against her, stretching her as it went inside her. She started pushing back slipping inch after inch into her pussy with relative ease, until all of his cock was in her. Then he pulled her close to him and sat down on the couch with her sitting on top of him. Her legs were splayed wide, I was able to see his cock stuffed into her pussy. He began to bounce her on his cock with his hips, each bounce making her boobs jiggle. His hands reached around her and squeezed her nipples hard. He crudely played with her tits by pulling and twisting her nipples, he even slapping her tits roughly. I watched her beautiful face as she writhed in pleasure, her cunt stretching to accommodate him as he pounded into her wetness, her breath coming in short gasps before she shuddered with another intense orgasm, proving that Mary really did love being treated like a little fuck toy. Jim pulled her up, off his cock, and pushed her onto her knees in front of him, jacking his cock for a moment before throwing his head back in intense pleasure and shooting his hot load all over her sexy face, her tongue catching whatever fell into her mouth, her makeup smeared from her eyes. She smiled, "Four little boys and now I'm all done." Jim got up to dress himself, and I noticed John coming through the door at the same time. Smiling John said "Guess I timed that about right." Jim smiled, dropping his hundreds on the couch, and I said "Here is your money. I will talk with you Monday." With that Jim and I both left. On Monday, Mary was in one of her dresses. When she saw me she just gave me a smile and moved on to her office. I walked over to the area where the guys were gathered. Looking right at John I said "I sure didn't think I would of lost that bet, but I'm seriously glad that I did." "Don't ever doubt me when it comes to women! My Dad couldn't believe I got the sexy goody two shoes Mary either, until he saw the pictures." Just then Mary walked over to us and bent down showing us her full tits and giving us our daily show. "Hope you boys had a good weekend." Mike answered "I think I can say this for all of us, "Hell YES WE DID!!" "Keep your voice down, we don't need everyone to see what is going on here." We all just smiled, even Big Bad John. Mary smiled and walked off. For the next two weeks Mary would come to where we were and bend over to give us a great view of her boobs and if no one was looking, a show. She and John continued to go to lunch together. When we moved to the next department John stopped having lunch with Mary and she went back to wearing her pant suits. John was now working on his next conquest. I continued to go over to Jake's and never told him anything about what was happening between his Mom and me. Mary would reward me for keeping my mouth shut with a blow job or a delicious fuck, depending on how much time we had alone. That fall, after I went to school, I always had a home with the family of my best friend, but my favorite moments were the ones that his mom and I could find together.