Mr. Monk on the Run, Part 2

This takes place in the episode "On the Run Part 2," at the end of the sixth season. Natalie Teeger has met up with Dale Biederbeck in his jail cell to try to catch him on camera admitting to his role in framing Monk.

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"Turn it off, please," said Dale Biederbeck from the confines of his wheelchair.

"Turn what off?" Monk's assistant, Natalie Teeger, had been sent to Dale's prison cell to try to extract some information.

"The video recorder in your purse, I won't be confessing to anything today, Natalie. We don't have to play games, I know Adrian Monk is alive! I never believed his oldest friend, Leland SCHtottlemyer would actually shoot him, did you?"

Biederbeck was no dummy, and was well aware of Monk's plans. He had, in fact, hoped this would happen...

"Aww... reeeallly... to tell the truth, I'm so relieved. I don't want Monk dead, ever since he put me here, my dream has been to trade places with the man. I want Monk... HERE. In this hellhole, rotting away, slowly slowly slowly..."

"What about Sheriff Rollins? We know he's on your payroll."

"Is he really?" Biederback was toying with the young blond, trying to lead her down the path he wanted and getting her to fall for his trap.

"He used to work here as a prison guard. Is that where you met him? And we know you hired Frank Nunn. You're planning something. Whatever it is, Mr. Biederback, you can forget about it, it's not going to happen."

Natalie was bold in her accusations, sure that her boss Adrian was correct and that Dale was behind this. But she couldn't bring him down for it, especially with her camera off.

"I'm afraid you're too late, Natalie. Wheels are in motion."

"It was nice meeting you."

"Wait wait wait wait, before you go... I suppose I could help you out. I'm quite confident that Adrian Monk won't be able to take down my plan to begin with, and I do quite enjoy a challenge. I could give you some information, if you'll help me."

The Whale's plan wasn't a strong one, but he had a knack for convincing people and twisting them to do what he wanted. And with the offer dangling before her, Natalie was quite willing to help out the oversized villain if it meant she could clear Monk's name.

"You so rudely interrupted my appointment with my pedicurist. My nails are highly in need of some treatment... but somehow I don't think you're qualified for that, yes?" he said as antagonistically as he could. He wanted Natalie to feel demeaned before he humiliated her.

"What do you want, Dale? I'm not in the mood for games, and I do have matters much more important than you to tend to."

"But in addition to my hands, that lovely lady took care of... let's say, my 'other' needs. With this in front of me," he said pointing to his stomach, "it becomes quite a chore to give myself pleasure, you see. If you take care of that, then your mister Monk will find himself in a much more pleasant situation himself."

Natalie gasped in disgust at the idea of prostituting herself for information that she wouldn't even need.

"I'm quite sure Monk can do just fine without your help, Dale. Good luck trying to play with yourself tonight," said Natalie as she turned and walked towards the jail cell.

"Then I suppose the Governor will find himself in a rather unenjoyable place tonight, and soon thereafter, Adrian will find himself where I am now... nice seeing you, Natalie. Shame we won't meet in the future, for our mutual acquaintance will be no more."

With the jail door open and Natalie ready to walk away, perhaps dooming her friend, she stopped to consider things. "Monk isn't infallible, Dale does know something... I'd do anything, but this? How could I have sex with... he's not a man, he's a thing."

"Attractive as it may be, letting me stare at your cute little bottom does nothing for either of us, Natalie. You can either continue walking out that door, or turn around and see whether or not we can put that ass to use."

Natalie dropped her head, becoming wrapped up in thought. After a few moments, she reached her hand out and pulled the door shut.

"What do I have to do?" she asked nervously.

"Everything that I want you to, Miss Teeger. You can start by putting down that purse on the desk. Wouldn't want your camcorder to come on and pick up any of the action, would we?"

Natalie walked towards his computer desk, and leaned over to place down her purse. Dale moved his wheelchair up behind her and stopped admiring and began touching. Natalie felt the large fingers on his hand tracing up the inside of her right thigh. She froze in place as his thumb hooked underneath her panties and rubbed them against her.

"A thong, Natalie, really? Seems quite odd of you to use this as your casual dress. Were you perhaps planning something for today? Pull it off... slowly."

Dale's hand retreated as Natalie's found her way to her pants. She pulled them down slightly, giving The Whale a perfect view of her ass. She grabbed the waist of her thong on both sides of her waist, and slid it downwards. When it dangled around her knees, Dale grabbed her hands and pulled them away. Natalie placed them on the desk to steady herself. It turned out to be a good move, as Dale's fingers immediately found their way towards her slit. She leaped at the feeling of his fat digits rubbing against her body. His index and middle fingers pried her lips apart and then plunged in.

"Ahhh... quite tight, dear. Guess you've been preserving yourself since Mitch died. Perhaps hoping that one day you would find yourself taking Trudy's place in Monk's heart?"

Biederbeck's thumb rubbed against her clit as he worked his fingers inside of her. Natalie was squeezing her eyes shut and clenching her teeth, not used to the girth inside of her and at the same time feeling like she should vomit because of whose hand it was. She gained some relief when he withdrew moments later.

"Turn around, Natalie. It's time to begin your work..."

When she turned to face Dale, she saw him licking and sucking on his now wet fingers.

"Quite delicious, my dear. But there's plenty more to go. You look quite sexy with your bush hanging out and your thong wrapped around your knees. You look just like a good little whore I knew... good little whores spend a lot of time on their knees, I understand. Get down."

Dale was unmistakably a pig, and Natalie would have done anything to avoid ever touching him. Yet without doing it, Monk would likely be discovered and returned to prison. Perhaps even killed.

She pushed aside his robe, revealing a multi-colored striped gown beneath. Dale pulled it up slightly, but forced Natalie to do the rest of the work. She quickly yanked at it, pulling it up over his stomach and revealing a monster.

"Never thought I'd be big all over, did you, Miss Teeger? Biggest you've ever had, I'm sure... you had to know there was a reason that I could get beautiful women as often as I did."

The thick head of his cock poked out just past his foreskin, and it rested on top of an even larger pair of balls. Even with how huge his body was, Dale's meat looked oversized.

Natalie wrapped both of her hands around it, but could barely encompass the entire thing. She gave it a few short strokes, and then held it up while she leaned her face in. Her tongue ran up the shaft while she tugged gently on the head. Freeing one hand, she reached down and began to massage his testicles. Dale placed his hand gently on the back of her head and ran his fingers through her hair as she started to work.

She brought her lips to the tip and gave it a light kiss, flicking her tongue at it at the same time. Natalie opened her mouth wide and inserted Dale's thick cockhead. It made for a tight fit, as both of them were well aware. Natalie preferred to work slowly, moving her way further down his cock while jerking the base of it. Dale was growing impatient, and got a tighter grip on the back of her head. While going at her own pace, Natalie left herself open for Dale to take control. He pulled back with his hand and Natalie found herself impaled on the immense length of The Whale's organ. She gagged as the tip pushed itself as deep down her throat as it could and started to smack him on the thighs. But Dale didn't give in, now moving Natalie's mouth over himself as he pleased. But he was too fat to go all that fast, instead opting for cramming as much in on a single thrust as he could.

For several minutes this went on, until tears were running out of the cute blond's eyes and she was gagging even more. Dale pulled his hand away and she leaped away, falling on her back while she coughed up a mixture of saliva and precum.

"Quite the promising mouth you have there. Is the rest of you... up to par? Get up, and make it snappy."

Natalie leaned up on her elbows, and pulled herself to her feet as quickly as she could. She was facing Dale, her eyes firmly fixed on his manhood which was dripping wet.

"Turn around and back up. I don't want to see your face when I'm fucking you... I'll imagine it's someone more attractive. Maybe I'll even picture you as Trudy - don't you wish Monk would do that?"

Natalie did as she was told, putting her ass right next to Dale's lap. He gripped his dick and rubbed it at her entrance, taunting her even further. The tip slid in quite smoothly, though the rest proved a struggle. The more he tried to force his way in, the tougher it proved.

"A bitch as tight as you doesn't deserve to get something as sweet as this. I'll put more work into just getting inside of you than I will into ruining you for every man you'll fuck after me..."

Dale found himself halfway inside of her, but with plenty of room to go. Natalie was positioning herself to get fucked standing up, but Dale's hand shot around her waist and pulled her back. She was stuck in his embrace, and further stuck on the pole crammed inside of her tight cunt. Dale used his free hand to pull up her top, and tore away her bra, snapping the straps clean off and letting her small breasts hang free.

"If only you were a C-cup instead of a B, you might be my perfect woman, Natalie. But you're flawed... do you know what I do to flawed things?"

He angrily groped at her chest, squeezing her flesh tightly. Natalie winced in protest, at which time Dale thrust himself upward as best he could. His dick hit her so hard that she nearly flew off his lap. He began to work himself into a rhythm, pounding into her snatch as quickly as he could, but his own fat was working against him.

"It seems you might have to do most of the work here, honey. Your body is too... tender... for me to properly use."

Natalie took the hint and began to grind herself on his dick. She reached back and placed her hands on his chest, trying to give herself some leverage to bounce. His left hand was still playing with her tits, now having moved on to pinching her nipples and pulling at them. Natalie was grunting with each thrust, but Dale couldn't tell if it was because it hurt so much or because she was starting to enjoy herself. Every time she pushed herself up, her ass sat right in front of Dale's face. He was getting a bit eager to wreck her in both holes, but knew that he would never fit. Instead, he slipped his thumb inside of his mouth and began to suck on it to lube it up. Natalie stopped humping away to reposition herself, and Dale struck. He planted his hand firmly on her ass, spanking her, and then spread her cheek to the side. He positioned his thumb at her hole, and shoved it in as deeply as he could.

"AHHHH!!! What are you doing?!"

"Whatever the hell I want. You're nothing more than a set of holes to me right now."

Natalie was breathing heavily now that both holes were getting plugged, but she continued to move herself on top of The Whale's prick. Though it was a tight fit, Biederbeck still managed to maneuver his thumb inside of her rectum. It only pushed a small ways in, but it was more than enough for his tastes. And judging on the sounds coming out of Natalie's mouth, it was plenty for her too.

"Oh god... mmm...it's not right... but... uunnn.... yesss..."

"Starting to like it, sweetheart? Everyone eventually falls for me... but unless you'd like to walk away from here with a dripping cunt and sticky thighs, I'd suggest you get off of me and get on your knees."

Natalie hadn't cum yet, but she definitely didn't want to feel Dale's cream inside of her for the rest of the day. Quickly dropping to her knees, she grabbed hold of Dale's meat. She sucked on it while jerking him off with both hands, tasting herself on him in the process. Natalie felt his body tense up, and he let out a series of groans. She pulled away as quickly as she could, but the first shot of his semen went into her mouth. She coughed and it flew out on to his cell floor, but in the process, she was hit by several more air strikes. Natalie continued tugging at his dick as he let his jizz fly, and his aim was dead accurate, hitting her in the forehead, on her cheeks, and right on her lips. She sputtered as the thick load flew through the air and on to her face, trying to spit away all of it that entered her mouth. It took a full minute before Dale was fully milked, and Natalie's face was completely white with spunk.

"Oh me oh my, what a mess I've made with you, Eager Teeger. You surely can't walk out of here looking like that... perhaps you should clean yourself up. Maybe even have a bit of a meal before you go? My treat, of course."

The no-longer perky blond understood his meaning, and began using her fingers to clean the thick coating on her face. She slid her hand along her cheeks, dragging the sperm with her and pushing it into her mouth. Each time she swallowed loudly and then licked her hand clean of the leftovers, until her face was as clean as ever, and her stomach full of a tremendous load.

"You did well, Natalie, and your end of the bargain has come true. So... what can I tell you to help out detective Monk?"

Natalie sat on the floor with her tits hanging out and her pants pulled down, her abused cunt being cooled by the cold air of the cell. She started to recompose herself and redress, as she prepared for a long talk with Dale "The Whale" Biederbeck.