Kelly Bundy Bets Her Ass

byInishfree©

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."

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, "oooooooooooooooooooooooooooh."

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 but 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 lolipop, 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. It's 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 website. 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 website."

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; 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 website 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 70-30 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 they thoroughly enjoy getting their pussies screwed.

All of them are refusing a butt fucking and getting the same treatment that Kelly went through.

The membership is constantly rising for the website. 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 bet; and 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 website, 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 websites, 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 website is still growing.

Richard is an intelligent business man 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 lovemaking sessions.

"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 without reading it. Even if she did, Richard has taken great care to create 'the fine print' in his new contract papers.

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 Jiggly Room."

Richard obliges her and quickly removes his clothes.

As his shorts are lowered, Peggy is 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 over six months," she says. "Come to momma."

Peggy turns around, getting on all fours and 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 cheer. "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."

Report Story

byInishfree© 12 comments/ 76553 views/ 40 favorites

Share the love

Report a Bug

PreviousNext
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel