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.