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Introduction:

Kelly Bundy bets her ass.

Richard Baker has lived in his house, on Jeopardy Lane, for 21 years.

He bought the house, in a suburb outside Chicago, when he took the job as a salesman for a major pharmaceutical company. At the time, Richard was a young man, only 24 years old.

His job has been a successful one, as he went from a salesman to manager of their research and development department, over the years of his employment.

Everything has worked out great for him, except for his house and property increasing in value; as he had expected it to.

The lack of increasing property values, in the neighborhood, has been because of the house adjacent to his. Richard Baker lives next door to Al and Peggy Bundy.

You see, Al has never taken very good care of his house and property. All the neighbors complain about it; but Al Bundy could really give a shit about what other people think.

Al wallows in self-pity about his failure life and his nagging wife, Peggy, complains about almost everything. Their two children, with no proper upbringing, rarely help out with anything.

Their son, Bud, is too busy trying to lose his virginity. Their 20 year old bimbo daughter Kelly, is too busy trying to fuck every good looking guy in the greater Chicago area.

Richard is sitting on his front porch, one fine Saturday spring morning. He is drinking coffee and reading his newspaper.

His faithful companion, Roxie, is lying down by his side. Roxie is a beautiful six year old female Boxer. Richard has owned her since she was a puppy. She is a loving dog and very well trained.

After a while the dog gets up and goes to lie on the lawn, soaking up the morning sun. A few minutes later, Kelly Bundy comes out of her front door.

She sees the dog, on the lawn, and calls out to her. “Come here Roxie, come here.”

The dog leaps up to attention. Kelly has played with the dog since it was a puppy. They like each other very much.

Roxie darts to the edge of her lawn when Richard yells out, “Roxie, stay in your own yard. You know better.” The dog halts and looks back at him.

“It’s OK, Mr. Baker,” says Kelly. “She was just coming to see me.”

Richard gets up from his chair and walk to the edge of his porch. “Roxie knows not to leave her property without me. I would prefer that you come over here; if you want to play with her.”

Kelly walks over and starts to wrestle with her, as boxers love to do. “You’re a good girl. Yes you are. You’re such a good girl,” Kelly says as she plays with the dog.

“This is such a sweet dog,” Kelly tells Richard. “I hope it’s OK if I come over and see her once in a while.”

He walks over closer to Kelly and the dog. “I don’t mind at all. Roxie really likes you. Say, Kelly, now that I think of it; I have a job offer for you.”

“What kind of a job?” Kelly says suspiciously.

“Here’s the deal,” Richard explains, “I am leaving early Monday morning for a business conference. I’ll be gone until Friday afternoon.

I was wondering if I could get you to come over and feed Roxie for those five days. I’ll even pay you $50.”

Kelly starts to back pedal on the offer. She was never too keen on work.

“I don’t know, Mr. Baker. I’m usually busy all the time,” she says.

“Oh, come on now Kelly. It will be real quick and simple. It will take you less than five minutes a day. Come on in the back yard, let me show you.”

He puts his hand on her back and gently persuades her to enter his back yard. Kelly is acting reluctant but not putting up a big fuss.

“Look, all you have to do is feed her,” he explains.

“Roxie has an automatic water bowl that keeps filled. I have a container on my enclosed back porch with her food. All you have to do is take out two scoops and put it in her dish. That’s it, simple as pie.”

Kelly is slightly shaking her head, in a negative manner. “I don’t know, Mr. Baker.”

Richard needs to charm her in to agreeing with this.

“Roxie loves you, Kelly. She needs you. If you don’t let her stay here, in her own yard; then I’m going to have to board her at the kennel. She really hates going there. You don’t want that to happen, do you?”

“Here she gets to play in her own yard and sleep in the enclosed porch at night. All you would have to do is make sure that you close the front gate. See how easy it all would be.”

“Come on, Kelly. You’ll make $50 for probably less than 30 minutes of work.”

Right then, Roxie runs toward the screened porch and bursts through the dog door, in one of the wall panels. “Hey that’s cool,” says Kelly. She runs over to the dog door, gets on her hands and knees, trying to crawl through it also.

Kelly begins squirming her way through the door in her very tight and low cut jeans and a blue halter top.

As she tries to crawl through the opening, she has to shift her shoulders to get through. Her shoulders clear the opening and her waist slips right through, but when she gets to her hips, the opening is too small.

She gives up the attempt and tries to back out, but now her shoulders are square and she can’t get through. Kelly struggles with her predicament and begins to panic.

“Help me! I can’t get out of here. I’m stuck,” she cries out.

Richard is standing behind her getting quite a show. Kelly’s ass is wiggling back and forth, in physical desperation. He momentarily just ponders the sight of her incredible back side.

“Let me help,” Richard comforts her. “Just bring one arm out at a time.”

He reaches in grabbing her one arm to lead it out while he tilts her shoulders. Very quickly she gets out of her predicament.

“Thanks for saving me, Mr. Baker. I thought I was a goner,” says Kelly.

Richard tries again to convince Kelly to take on the job. “I just helped you out, Kelly. Please help me out here. I need you to feed the dog. You’d be doing me and Roxie both a big favor,” he begs.

“Let me think about it,” Kelly answers.

“I’m pressed for time,” Richard explains. “I need to know before tomorrow morning. If you won’t do it then I’m going to have to make arrangements with the kennel.”

Kelly thinks for a minute. “OK, I’ll come by tonight before I go to the club with my friends. I’ll give you my answer then. I’ll come over about 8:00 tonight.”

Richard sighs in relief. “All right, I’ll expect you about 8:00.”

Richard jumps into the shower around 6:45pm. He is later standing in the bathroom, in his robe. He has brushed his teeth and is grooming his hair, when the doorbell rings.

He looks at his watch and sees that it is 7:20. He walks to the front door and looks out the peep hole, to see who it is.

He is surprised to see Kelly Bundy standing on his front porch. He slightly opens the front door and peers out. “I just got done with a shower, Kelly. Aren’t you a little early?”

Kelly fidgets, “Well, my friends called me and told me that some really cute guys are showing up at the club early. I want to get there before all the good ones are gone. Can we do this now?” she asks.

“Come on in. You’ll have to excuse the bathrobe,” Richard says. “No big deal,” Kelly tells him.

Kelly walks into his house and he directs her toward the den.

Kelly is all slutted up for a night on the town. She is wearing a short red stretch dress that caresses every curve of her body.

As she walks in front of Richard, he is given a show of her curvaceous ass being cradled by the thin dress material that tightly stretches across it. Kelly’s toned, naked white legs look incredibly long and her beautiful blonde hair flows around her shoulders, as she walks to the den. This girl’s body is a true vision of loveliness.

To accent the intention of her attire, she is even wearing ‘screw me’ pump heels.

Richard asks her to have a seat but she declines, saying that she is in a hurry. He sits himself in a chair, while she stands before him.

It is clear to Richard that Kelly is not wearing a bra. Between the early evening cool air and the tight dress, her nipples are quite prevailing.

This tight fitting dress envelops her breasts to show their perfect shape and form. Looking down to her waist and hips; she doesn’t even show a panty line. If she’s wearing a thong, there is no evidence of it.

Richard is quite pleased to be blessed with this vision.

“So, do we have a deal?” asks Richard.

Kelly stands there, in a sexy pose, a hand on one hip and with one leg stretching to the side.

“We can have a deal but not for just $50. I’ll take care of Roxie but it’s going to cost you $200.”

Richard tries not to raise his voice. “Two hundred dollars, are you crazy?”

Kelly grins at him. “I did a little research, Mr. Baker. I called the kennel and found out that they charge $60 a day. So I figure that I’m doing you a favor for only $200.”

“You’ll save $100 and Roxie gets to stay here. I put all the facts together and you’re running out of time. I’m betting that you will cave in and pay me the $200. I think it’s a good gamble to say that you’ll gladly pay me what I want.”

“I see that you’ve done your homework,” he says. Richard has a gamble of his own in mind.

“You seem to know all the odds. So you consider yourself to be quite the gambler, do you?”

Kelly smirks, “I may not be smart but I’m not stupid. I figure the odds are in my favor and it’s a good bet.”

Richard thinks for a moment. “You know Kelly, I could probably get Bud to do this job for $50 but I’ll play along with you on this.”

“So you like a good bet, do you? I’ve got one for you. I’ll make you a bet. If you win, I will pay you the $200 to care for Roxie plus I’ll give you an extra $500.”

“But if you lose the bet, you will have to take care of Roxie for the original $50 that I offered. So let’s see what kind of a gambler you really are, interested?”

“Now let me get this straight,” Kelly says.

“You’re going to pay me the $200 I want, plus another $500. There’s got to be a catch. So what’s the bet?”

Richard calmly looks at her. “The bet,” he says, “is that you can’t deep throat my cock.”

Kelly’s face flashes in amazement and then she begins to laugh hysterically. “Ha, Ha, Ha, Ha, Ha!! You old perverts are all alike. You think that you can flash a couple dollars in front of a young girl and get anything you want.”

“You’ve got to be kidding me. You must think that I’m a total idiot. That’s the dumbest bet I ever heard.”

“If you think that I’m going to let you put your old wrinkled weenie in my mouth, then you have another thing coming. You know, I can get just about any young stud to throw me some cash to experience the wonders of my talented mouth.”

“Is that so? Then tell me, when was the last time that you got $500 for a blowjob?” he asks.

“I think that you just aren’t up to it. I think that you’re worried about losing. And you dare to call yourself a gambler.” Richard has now thrown down the gauntlet on this young tart.

The wheels start to turn in Kelly’s head. They sound similar to a hamster running on an old squeaky metal exercise wheel.

She thinks to herself, “$500 just to deep throat this old guy. I can do that. His cock can’t be that big. My old boyfriend, Jimmy, has a 10” cock. It took a little while but I got that one all the way down.”

“And this is my reputation that we’re talking about. Nobody sucks a cock better than Kelly Bundy.”

“What if the word got out that I passed up on this bet? I’d never live it down. I’d be more than stupid. That’s it; this old guy’s going down.”

Kelly indignantly looks over at Richard and says, “You’ve got a bet. And that’s $500 cash, tonight.”

“All right, let’s get started”, she says. ”I’ve got places to go. It’s going to be fun spending that money at the club later.”

“First we need to draw up a contract,” says Richard.

“I don’t need a contract. Let’s get this over with,” Kelly demands.

“A contract only protects both of us for the bet,” Richard explains.

“That way no one can back out of the deal. It won’t take but a minute for me to type one up on my computer. We both sign it and then we can begin.”

Kelly doesn’t like the wait but agrees on principle.

Richard gets it drawn up and prints two copies. Kelly signs both of them without reading a word. Richard then signs them, as well.

He offers a copy to Kelly but she doesn’t really care about the paperwork.

“Let’s get down to business,” she says.

“I’ve added one more clause to the contract,” he tells her. “You should have read it.”

“With the original bet, there was nothing to profit me; if I win the bet. So the deal now is that if I win, I also get to fuck you.”

“Nooooo way,” Kelly lashes out.

“You are such a freak. Why in the world would I ever let an old man like you fuck me? The deal is off.”

Richard picks up the papers like he is going to tear them. “I guess you would have lost anyway,” he says insultingly.

“Wait a minute,” Kelly challenges. “The deal is still on. I’m going to win this bet and then laugh in your sorry face.”

Richard stands up, from his computer and moves to the middle of the room. “You might want to take off your dress,” he suggests.

“God, don’t you ever give up? Now you want to see me naked. You really are an old pervert,” Kelly barks at him.

“Considering all the saliva and perhaps semen, I didn’t think that you wanted to stain your pretty dress,” Richard explains.

“Oh, you’re right. I’m sorry for being so bitchy at you,” apologizes Kelly. “That’s actually very considerate of you. Thanks.”

Kelly pulls down the zipper, at the back, and lets the dress drape down on her. She wiggles it off her hips, steps out of it; and puts it on a chair.

Richard was right. No bra and no panties.

Kelly stands there naked, still wearing her pump heels. She has an absolutely gorgeous body.

Scrumptious C-cup breasts, firm flat stomach, beautiful shapely hips and her delicious creamy white legs.

Completing the entire package is her firm apple bottom ass. It is a piece of nature’s art, that should be in a museum for everyone to see.

She has all of her dark blonde pubic hair removed; except for a heart shaped patch above her pussy.

Richard hasn’t seen such young nubile beauty for many years.

Kelly kneels down in front of Richard and looks up at him. “Let’s get this over with,” she says.

Richard unties the knot on his robe. He then shrugs it off his shoulders and lets it drop to the floor.

Kelly, kneeling on the carpet, looks at him and says, “Oh, damn it.”

Kelly is facing an 8” cock.

Normally this would be of no concern to her. Sucking down an 8” cock is like a walk in the park for her.

The problem is that this 8” of hanging meat is completely flaccid.

In shock for a moment, Kelly does not know what to do.

She then thinks to herself, “All I have to do is get this down my throat before it grows any bigger.”

Picking up the limp cock with her hand, Kelly begins stuffing it in her mouth.

The first 4” go in without any problem. From there on she really has to engage sucking power to draw the soft meat further down her throat.

Now is where the real problems begin.

Kelly has forgotten just how her exquisite oral talents can quickly stimulate any man. Suddenly, for every inch that she sucks down; another inch is growing.

As Richard’s cock gets semi-erect, Kelly is furiously playing a game of catch up.

“Mmmmph, Mmmmph, Mmmmph,” Kelly gasps, as she tries to engulf his extending rod.

Pulling off for a second to catch her breath, she whispers, “Oh fuck.”

Within minutes, Richard’s cock has now grown to a stiff 13”.

Kelly is now putting all her talents to work. 8” down, 9” down, she’s giving it everything that she has. Kelly is not giving up and she pushes herself to the limit.

10” of cock is now down her throat. Finally she pushes over the top and has 11” of his throbbing shaft in her mouth.

As hard as she tries after that, she realizes that she has reached her threshold. She’s got her arms wrapped around his hips and she’s driving as hard as she can.

But failure is in sight. Kelly realizes that she is going to lose the bet.

Meanwhile, Richard is ecstatic looking at her face, filled with panic. She is wide eyed with fear, and snorting air out through her nostrils like a bull.

After several minutes and many attempts, Kelly finally succumbs with an, “I can’t do it.”

“You win, Mr. Baker. You’ve got the biggest cock that I have ever seen. I bow to the master,” Kelly repents.

“Now, now, Kelly,” he composes her. “You gave it a valiant effort. And since we are this close now, you don’t have to call me Mr. Baker.”

“You can call me Richard. Better yet, all my friends call me Dick.”

Kelly flashes a very sexy smile at him, “You mean Mr. Dick, don’t you?”

“I want to thank you for the gambling lesson but now you get to claim your winnings.” Standing up, she grabs hold of his cock and walks toward the couch.

She kneels up on the couch and in her best sultry voice tells him, “I think that I still owe you a good fucking.”

Kelly guides the head of his cock toward her pussy and she turns around smiling seductively and says, “I bet I can take the whole thing now.”

Richard moves up close behind Kelly. He rubs his cock on her pussy and is surprised to feel that it is already moist.

Her exhilaration, and anticipation, during the blowjob obviously has got her juices flowing.

Pushing the head of his cock in, he is pleased at her tight firm grip. Kelly purrs as he penetrates her even deeper.

With 6” of cock pumping in and out of her, Kelly is in her realm.

“Oh fuck, yeah,” she moans. “Deeper, deeper, I want more,” she begs.

Richard doesn’t make her wait as he adds 4 more inches into her.

“How’s that baby? You doing OK?” he asks.

“Oh Dick,” she moans. “Don’t talk, just fuck. Oh God, just fuck me.”

He wastes no time in seeing how much Kelly can take.

The two of them become a fucking frenzy as Kelly is whipping her head around in total ecstasy and Richard is driving homeward bound.

He eventually is slapping his pelvis against her firm buttocks and pumping for all his might.

Kelly has totally lost it now. Her body is shaking violently and she’s screaming at the top of her lungs.

“Oh God, Oh God, Sweet Jesus in Heaven. Hold on Lord because I’m cumming home.”

Richard does everything that he can to hold on to her flaying body. Kelly grips the back of the couch and is rocking it on its legs, while climaxing.

Richard finally reaches his peak, as well, and blows huge spurts of cum up her pussy; as he continues to pound his cock in and out of her.

The two exhausted sex mates collapse on the couch. Richard is lying on top of Kelly’s tired body.

“I have never, and I mean never; been fucked like that,” whimpers Kelly.

“You give a whole new meaning to ‘how far can you go’. I have never met a guy with a cock like yours. I’d really like to stay longer but I’ve got people to meet tonight.”

”Let me catch my breath, and then I’ve got to go.”

Richard, also breathing hard, tells her, “You can’t leave yet. We’re not done. I’ve got one more hole to go.”

With that, Richard sticks his finger up Kelly’s ass.

“What the fuck are you talking about?” Kelly panics.

“I never agreed to that. There’s no way in hell that you’re sticking that log in my butt.”

Kelly tries to get out from underneath him but he has her trapped. She struggles, but is getting nowhere. Richard is forcefully holding her down.

“LET ME GO!!” she screams.

While she is thrashing around, Richard manages to open a jar on the adjacent table. He reaches inside and pulls out an inhalant capsule.

Holding her down even tighter on the couch, he gets his hands in front of her face and breaks the capsule right under her nose.

In seconds, Kelly collapses on the couch, unconscious.

Richard’s pharmaceutical company has his R & D department to thank for a new product that they have developed. It is especially geared toward mental institutions and prisons.

It is an inhalant capsule that will render a patient or prisoner unconscious for about ten minutes.

This allows them the time to restrain the person and move them to an area where they won’t be a danger to others and themselves.

Richard picks up Kelly’s limp and naked body from the couch. He carries her over to a low back leather chair.

He then places her backwards in the chair with her knees and lower legs on the chair seat and hangs her arms over the back; resting her chest and shoulders on the back.

He then takes cotton ropes and ties her legs, behind the knees, to the seat of the chair.

He also ties each of her ankles to the front legs of the chair. Finally, he ties her draped arms to the rear legs of the chair.

Richard then gets a turkey baster, fills it with lubricant, and inserts it up Kelly’s ass. Though unconscious, she lets out soft moans as it penetrates her.

Fully inserted, he slowly withdraws the baster while squeezing the bulb, to release all the lubricant inside her anal cavity.

A few minutes later, Kelly begins to regain consciousness.

“Ohhhh, what the hell? Where am I? What the fuck is this?” she mumbles.

She realizes her confinement and begins to struggle. She starts rocking the chair and looks up to see Richard.

“What the hell is going on here, Mr. Baker?” she yells.

“What happened to calling me Dick?” he questions.

“You’re the dick, that’s what. Let me loose from here; and I mean NOW,” Kelly demands.

“I would like to Kelly but it seems that you don’t want to pay off on your bet,” he tells her.

Still struggling Kelly yells, “I paid off on my bet. I let you fuck me. What else do you want?”

Richard calmly tells her, “Fucking your ass, that’s what you still own me.”

Kelly yells again, “I never said I would do that. Now untie these ropes. If you don’t, I will call the cops on you. This is kidnapping and rape. You’ll go to jail for this.”

“No one is going to jail,” he calmly tells her.

“You should always read the contract before you signed it. Our contract clearly states that should you lose the bet then the winner, that’s me, shall be awarded the following.”

“The loser, that’s you, shall submit herself to vaginal AND anal intercourse by the winner, that’s me.”

“Should the loser, that’s you, refuse to honor the contract; then the following shall apply.”

“The winner, that’s me, shall have the right to collect the winnings through any means possible; including bondage and by force. Look here, your signature is right at the bottom.”

“The contract also states that if the loser, that’s you, attempted to file any charges, then the winner, that’s me, shall have the right to sue for breach of contract. And that also includes any discussions about the bet to anyone.”

Kelly is now at a loss for words.

She then observes Richard opening up a jar, of what appears to be cream. He scoops a decent amount into his hand and begins to rub it all over his limp cock.

“Oh great, now I have to watch you jerk off too,” complains Kelly.

“No my dear,” he tells her. “This is another wonderful product that my company has developed. It’s an erection cream. It’s guaranteed to keep a man’s cock rock hard for twenty minutes.”

Kelly looks up in despair and says, “I’ll never learn to shut my mouth.”

Within about five minutes, Richard cock has gone from limp to a glowing 13” rod of steel.

Kelly now tries desperately to get on his good side.

“Look Mr. Baker, I mean Mr. Dick, I mean Dick darling. We can work something else out. How about this? I’ll try and deep throat you again. Even better yet, I’ll stay here all night and you can fuck my pussy until dawn.”

”Please, just not up my Yiiiiiiikes!!”

It’s too late for begging. Richard has already come up behind her and popped through her tight little anus.

The lube in her ass allows him to slowly insert his cock without stopping. He slides a fraction at a time, all the way in.

Kelly lets out high pitched shrills that seem to go up an octave, for every inch that he pushes in. Eventually you can only hear a very high tone, “ooooooooooooooooooooohhhh.”

With his balls resting against her firm ass cheeks, Richard whispers in her ear, “It’s all the way in Kelly.”

She regains her composure and speaks, “All the way, really? I took the whole thing. I can’t believe it. I can hardly breathe but I did it.”

Richard still at her ear, says, “Now I will teach you never to bet your ass again.”

He withdraws his dick about one inch and immediately shoves it right back in.

“OOOH,” comes out of Kelly’s mouth.

Another withdraw of now two inches and then slammed back in brings more from her, “OOOOH, OOOOH.”

This continues inch after inch until Richard is pulling his cock almost completely out of her ass and then driving it back in. He keeps this up as he is increasing in speed.

Kelly becomes a choir of resounding, “OOOH, OOH, AAAH, AAAAH, OOOOOO, OH MY GOD, SWEET LORD HARRY. PLEASE STOP, I GIVE UP.”

Kelly’s ass is on fire as this brutal ass fucking goes on, but suddenly she begins to find pleasure amidst the pain. Her body starts finding a new ecstasy that she has never known before. “OH, OH, OH, AH, AH, AAAAAAAH, FUCK ME YOU BASTARD. FUCK ME, FUCK ME, FUCK MEEEEEEEEE.”

Richard keeps pounding away for over 15 minutes then finally climaxes, as his legs almost crumble below him.

Kelly is close to passing out again. Her climax is way over the top and definitely one that she has never experienced; or that she will ever forget.

Once they both regain physical strength, Richard unties Kelly’s ropes to set her free.

With her new sexual experience completed, she is no longer angry at Richard.

Strangely, Kelly has new respect that an old guy like him has taken her to new sexual heights; that she never imagined existed.

Richard helps her get dressed. He escorts Kelly to the front door and opens it.

“I’m sorry that I spoiled your evening with your friends. Maybe you can still catch up with them,” he says tenderly.

“Fuck them,” says Kelly. “Who needs little boys when I’ve got a real man next door?”

Kelly starts to walk back to her house. She’s a bit dazed, and walking a little funny; but she’s safely headed for home.

Richard phones Kelly late on Sunday to remind her about caring for his dog. He leaves town the next morning and catches his flight to the business conference.

On Friday, he returns to find his home and dog in fine condition. Kelly had evidently not only kept Roxie fed, but she also came over every day to play with the dog.

Richard is very happy that the arrangement worked out so well.

Friday evening his doorbell rings. He opens the door to see a smiling Kelly. He invites her in and promptly pays her the $50 that she earned.

“Kelly,” he says, “you did a wonderful job taking care of Roxie. I really appreciate it and want to let you know that if I can ever be of assistance to you, please don’t hesitate to ask.”

“Well, there is a favor I would like to ask,” Kelly says with a naughty little girl look on her face.

“Anything, what can I do for you?” Richard tells her.

“Mr. Baker, I mean Dick, I have a reputation in this town and you have cast a cloud over it. Until I met you, there wasn’t a cock that I couldn’t swallow. I need to get my reputation back.”

“I was wondering if you would let me come over, once in a while, and see if I could win it back. I’d even let you fuck me too. That was really terrific.”

“Just no more fucking in the butt. I couldn’t fart for days after the last time. All that came out was a ‘poof’ when I tried. So what do you say? Can you do me this favor? Pleeease,” she sweetly asks with her little girl charm.

“I don’t see a problem with that Kelly,” he gladly tells her, “you can come over anytime. It would be my pleasure to help you out. I mean, a reputation is sometimes all that a girl has.”

Kelly immediately drops to her knees and pulls down the zipper on his pants.

“I’m here now,” she grins, “so I might as well put the time to good use.”

Kelly gives him another great blowjob but she still can’t get it all down. Kelly does get him to cum this time and gleefully swallows it all down.

She starts coming by every day, sometimes twice a day. The two of them are usually fucking, at least every other day.

Richard is in paradise and Kelly is very enthusiastic about getting her rep back. His big cock, fucking her several times a week, is also a real bonus to her.

Kelly is keeping Richard so busy that he has to bring a few more jars of that erection cream home from the office.

Four weeks go by and Kelly has yet to deep throat him, but she is getting close.

Kelly and Richard have also been experimenting with role playing. Kelly is sometimes a little girl in pigtails with a large lollipop, or a school girl who has been bad, or a candy stripper nurse. They’ve also played the babysitter role and the exchange student role. It’s all been quite a lot of sexual fun for both of them.

One afternoon Kelly shows up at his house again. “Dick, I think we have a problem.”

“Yesterday my girlfriend just showed me a porn site on that new computer internet web thing. The porn site is called ‘Kelly’s Playhouse’ (oddly enough),” she tells him.

“She said that the girl in the pictures and videos looks just like me. I told her that she was crazy. I told her that no way that was me.”

“But I’ve got to be honest with you. It was me and you on that porn site. Who could have taken those pictures and videos? I’m really worried.”

Richard pats her on the head and tries to calm her.

“I have to confess, Kelly,” he says, “I’m the one who took the pictures and videos. I’m the one who runs the porn site.”

Kelly begins to tear up. “How could you do that?” she cries. “I thought that we were friends. I thought that we had something really special together. How could you?”

Richard apologizes, “I’m sorry Kelly. I did it for the money. Besides, there was an images and video rights clause in our contract. It’s all perfectly legal for me to do it.”

”And I’ve made close to $1000 so far from that website. It’s a booming business with membership fees, and all.”

“You sold me out,” she cries. “I can’t believe it. Then I should get half the money. That’s only fair.”

Richard quickly comes up with a solution.

“Listen here Kelly,” he explains, “I’ve got a business proposition for you. If you can convince any girls you know to try and win that $500 bet from me; then we stand to make a ton of money.”

“I’ll con each of them to sign a contract, and well; you know what happens from there.”

“I’ll buy some more video equipment and teach you how to use it. Everything will be hidden so the girls don’t see you or the cameras.”

”We’ll put all the pictures and videos up on the porn site and then sit back and watch the money flow in.”

“So do you think that you could convince any girls to try that? Just tell them that I’m an old man with a bunch of money. Tell them that it’s just a silly game I play to get blowjobs.”

Kelly’s eyes begin to brighten up. “What a great idea,” she says. “Dick, you are a genius. Hell, I can think of at least a dozen girls right now. When do we get started? I’m going to be rich. I mean, we’re going to be rich.”

Richard quickly responds, “Since I’m supplying all the equipment and doing most of the work; I must insist on a 30-70 split, after expenses of course.”

Kelly jumps right back, “OK, but only if it’s 30 for me and 70 for you. I may be blonde but I’m not stupid. Oh, and one other thing, Dick; I hope that this won’t interfere with our quality time together. Will it?”

Shaking his head, Richard tells her, “Don’t worry sweetie, you’ll always be my number one girl.”

Kelly is grinning ear to ear. She’s not only flattered by his compliment, but she’s also thinking about all the money.

Everything goes better than planned. Kelly is recruiting girl after girl after girl.

Every single one of them is failing to deep throat Richard’s monster cock. None of them have even come close to Kelly’s first time. But all of them thoroughly enjoy getting their pussies screwed.

Each of the girls is refusing a butt fucking and, in turn; each of them are getting the same treatment that Kelly went through.

The membership is constantly rising for the porn site. With all these girls, there are pictures and videos galore.

Kelly, in the meantime, has regained her reputation.

One evening her throat finally opened up enough; and down Dick’s dick went.

She couldn’t have been happier. To her, it was her greatest accomplishment in life. Richard congratulated her with dinner at one of Chicago’s finest restaurants; and later a fancy hotel.

Ironically, it was while they were in a 69 position that Kelly swallowed him down. I guess it was the perfect angle for her throat, and with Richard chowing down on her pussy, that finally got her there.

Richard has been regularly feasting on Kelly’s pussy, in the meanwhile. He’d be a happy, happy man even if it wasn’t for all the cash that he is pulling in. He’s actually exceeding his monthly paycheck at work.

As the months go by, the word is finally spreading around about the size of his cock. It’s getting harder to find girls who want to give it a try.

Richard and Kelly eventually increase the prize amount to $750, trying to recruit more girls. They even end up raising the bet as high as $1000.

The problem, after a while, is that they only seem to attract the hooker crowd now.

The patrons, of the porn site, were delighted when they only saw fresh young girls. It appears that very few want to see a skanky prostitute on film.

One day, Richard comes up with another brilliant idea.

The only thing viewers want to see on porn sites, more than fresh young girls; is a MILF.

They raise the prize money to $1500 and Kelly starts canvassing the local shopping malls.

This time, in order to compete, the women must fill out an application form. Richard arranges to have their backgrounds checked to be sure that they are indeed suburban housewives.

Once again, business is booming. The number of women coming in is by no means at the volume that it was before, but the porn site is still growing.

Richard is an intelligent businessman though. He knows that they have reached their peak. He just hopes that they can continue to make money, as long as possible.

One day Richard gets a phone call from a woman who identifies herself as Mrs. Smith.

She says that her friend told her about the opportunity that is being offered. She also says that for reasons she can’t discuss, she won’t be able to fill out an application form.

At first, Richard refuses but then relents later on; because there hasn’t been that much new business lately. He tells her to come by at 8pm that evening.

He calls Kelly and lets her know that another client is coming by. Richard tells her to be sure and get there before 7:30, so they can get all the equipment set up properly.

Kelly shows up right on time. They have everything ready to go. Kelly gets in the adjoining room to observe the monitors and work the cameras. She closes the door and hides out.

At 8pm the doorbell rings. Richard opens the door but is surprised to see his next door neighbor, Peggy Bundy. His immediate thoughts are that he and Kelly are busted for their sexual escapades.

“Oh hi, Peg,” his voice cracks. “I haven’t seen you in a long time. What can I do for you?”

Peggy is standing there in her tight spandex pants and high heels. She’s doing her little wiggly dance with her feet while her tush bounces around. “Well,” she says, “today I’m actually Peggy Smith.”

She then proceeds to just barge through the front door. “I’m here to claim my $1500 prize. Now what do I have to do?”

Richard is momentarily frozen. He’s not quite sure what to do. He finally figures ‘what the hell’.

“To win the money,” he flatly tells her, “you have to deep throat my cock.”

Peggy gives him a sly grin. “Oh my goodness,” she says, “is that all? Then drop those pants, baby. I’m in a hurry. Oprah’s coming on soon.”

During this whole time, Kelly is unaware of what is happening. Her mother and Richard are standing in the foyer and she can only see the den, on the monitors. She waits patiently to start the cameras.

Richard, in the meantime, is explaining to Peggy about the contract. He also explains about her getting fucked if she loses. Peggy figures that she’s got nothing to lose and everything to gain.

She is indeed Kelly’s mother because she just signs the contract, without reading it. Even if she did, Richard has made sure to create ‘the fine print’ in his new contract.

As Peggy enters the den, she is already removing her clothes. She learned about cum stains, a long time ago, in the back seat of Al’s old Dodge. Peggy has a little junk in the truck, but still has a fine body. Best of all are her large E-cup breasts. It is clear that Kelly didn’t inherit her mother’s chest.

As Richard enters the den, there is a loud noise from the next room.

Upon seeing her naked mother on the video monitor, Kelly fell over in her chair.

“What was that?” Peggy nervously says. “God, I hope it’s not Al. He’d kill both of us. Besides, the money is all for me; not that sexless shoe man.”

Richard thinks quickly. “It’s just my dog,” he says. “There’s nothing to worry about.”

He gives a long glaring stare, to where he knows a camera is. Kelly gets back in her chair and quiets herself.

“Let’s hurry up,” Peggy says. “You never know when Al might get home from the nudie bar.”

Richard obliges her and quickly removes his clothes.

As his shorts are lowered, Peggy is shocked and startled. “Oh my Lord!!” she exclaims. “Is that thing for real? Boy, have I got my work cut out for me.”

She wastes no time and drops to her knees.

As good as Peggy may have been in her youth, she has lost her touch. As hard as she tries, there is no way that she is going to win.

With barley 7” going down her throat, she finally throws in the towel.

Knowing what she has to pay now, Peggy doesn’t miss a beat. “I haven’t had a cock in me for months,” she says. “Come to momma.”

Peggy turns around, gets on her hands and knees, then spanks the cheek of her ass. Richard wastes no time and mounts her pussy from behind.

Kelly, watching from the next room, doesn’t know whether to be excited by all this or to close her eyes. Her own mother is acting like a wild animal. Kelly has never seen anyone so crazy and vocal about sex.

Peggy has no problem taking all of Richard inside her. She is whipping her head around and red hair is going everywhere. Richard, in the meantime, is grabbing her huge swinging tits and squeezing them with all his might.

“That’s it, baby,” Peggy growls. “Mama likes it rough. Fuck me hard. Come on now, HARDER.” Peggy Bundy is having the ride of her life and she is really enjoying it.

Once she’s had five orgasms, all in less than 15 minutes; Richard decides to stop.

He hasn’t shot his load yet and wants to get on with things; so he can get Peggy out of here.

When he explains his next intention and pokes his finger up Peggy’s rear end, she lets out a squeal. “Oh goody, there’s a bonus prize. This IS my lucky day. Well let’s go, big boy.”

Without hesitation, Richard grabs some lube and greases up his tool.

Peggy’s ass is fairly loose and he has no problem getting it in. As he drives more inside her, there is no resistance from this woman.

“Yee Haw,” she screams. “Ride ‘em cowboy. My ass hasn’t been fucked this good since I was in Wanker County. I once made the mistake of bending over in front of my Uncle Zeb’s mule.”

”Come on stud, give Peggy what she needs.”

It doesn’t take but a moment before Richard has all 13” going in and out of Peggy’s ass. He keeps pounding away for the better part of 10 minutes before his nuts start to swell.

He begins filling her up with cum; as she screams out in orgasmic pleasure.

Shortly after they are done, Peggy is up off the floor, getting dressed and heading for the door.

“Oprah’s on in five minutes,” she says. “Got to go, but maybe I’ll come by some other day to ‘borrow a cup of sugar’; or something like that.” Peggy gives Richard a peck on the cheek and heads back to her house, wiggling her ass the whole way.

After her mother has gone, Kelly comes out from the next room. She appears to be in shock.

Richard immediately tells her, “I’m really sorry that you had to see that, Kelly. It must have been very traumatic for you.”

”After all, it was your own mother. If I had known, I never would have called you over here. You never should have experienced that.”

”Once again, I am really sorry.”

Kelly shakes her head. “I can’t believe it,” she says with a baffling look. “Do you know what this means? Do you know what I’ve got to do now?”

Richard tries to comfort her. “I don’t know,” he says, “throw up?”

Kelly spins around and looks at him. “NOOO. You don’t get it. You don’t get it at all.”

”She took your whole cock right up her butt without as much as a whimper. In fact, she was screaming for joy.”

“How can I live with this? I won’t be able to show my face anywhere.”

“She’ll probably be blabbing about it tomorrow, at the beauty shop.”

”Then the word will spread all over town. Then all my friends will be talking about it.”

“I’m in deep trouble here. I’m not talking about what people will think of my mom. I’m talking about what people will think of me.”

”I’m talking about my reputation here. I’m talking about what I have to do now. I have to learn to take all of you up my ass, without being tied to a chair.”

”Where’s that jar of erection cream? We’ve got a whole lot of work ahead of us.”

Kelly grabs the jar, turns, and walks out of the den.

She looks around, with a very sexy smile, and crooks her index finger at Richard; indicating for him to follow her.

Kelly heads for his bedroom, shedding her clothes as she goes.

Richard follows her to see her climb up on his bed, naked, and get on all fours.

“I think we should get started right now,” she tells him. She wiggles her cute little ass at him.

“I don’t care how long it takes,” she says. “I’ll come over here and do this a hundred times until I get it right.”

”Just do me a favor and start off slow. Only a little bit at a time; please darling.”

Richard gladly tells her, “Don’t worry Kelly. I’ve got your back. I’m right behind you, all the way. Hell, it might take two hundred times, but I’m here for you.”

Richard then grabs a handful of cream and gets his cock hard again. He also lubes up Kelly.

He takes the head of his pulsating cock and gently pushes it through Kelly’s little pink rosebud.

Very slowly and very lovingly, he moves it in only about four inches and starts a tender methodic pumping.

Kelly lowers her face on to the bed and mews softly, “Oooooooooh, my big sweet Dick.”

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