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The Wager
Dean Hot in B&W

Title: The Wager – Act 1
Author: Deancaged
Pairing: Dean/Zia Nova, Dean/Anna Dresden
Rating: NC17

Other Players: Eric Kripke, Mc G
Warning: het, anal, oral, rough sex, huge cock, cheating fiance, bathroom sex
Disclaimer: I don't own Dean Winchester or Supernatural.
Summary: While Dean is caged up in prison, his fantasy life is his only sexual release. One of his fave fantasy scenarios stars him as a hot young actor in Hollywood who nails sexy starlets. His latest sexy scene features three hot frisky women and one wild wager.

A/N: A huge thanks to my friend, Nicole, for the beta work and advice. You Rock, Baby!

The Wager

The Wager Dean sexy 434 h x 397 w

Dean Winchester and Katerina Kovia were both waiting inside the conference room at Wicked Flix for their new client to arrive. Dean was an actor and stunt coordinator who was a rising star in Hollywood. Katerina was his agent and career advisor. When the producer and his team arrived, they were led into the conference room by a production assistant. There Dean met the producer, Eric Kripke, the lead actress, Zia Nova, and a young blond guy who turned out to be the director of this horror epic, Mc G. After sending the PA to get drinks for everyone, they all sat around the conference table while Dean presented some ideas to help punch up the action scenes in the movie Kripke was producing. The film was a low-budget horror movie called Zombie Nights.

Kripke was your typical cliché Hollywood producer. He was a short pale balding mid-40's guy who drove an expensive sports car and wore a $20,000 watch. The story on him was that he had somehow gotten to be a very successful producer in LA by persistence and a love for the horror genre. He made his first fortune in popular B horror films and his second in big budget action thrillers with horror elements. He was returning to his horror roots with Zombie Nights.

After Dean made his pitch, Katerina put in Dean's promo DVD so Kripke and Mc G could see Dean in action. Dean took the opportunity to observe the leading lady of the film. The only part of this meeting that was enjoyable so far was watching Zia. Hollywood is full of sexy beautiful starlets, but Dean had to admit this one was special. Zia was a sexy actress from Georgia who seemed very eager and ambitious. She was to be the star of the gorefest of blood, who meets a bunch of hungry Zombies and after a lot of carnage and destruction, somehow manages to defeat them and survive. If he got the movie, Dean was going to be working very closely with her, and he was looking forward to that possibility. She was about 5'8" with long golden blond hair and bright green eyes. Zia looked to be about 23 or 24. She had a gorgeous golden tan that made her skin glow, She was dressed in a tight red mini dress that showed off her fabulous figure. Her breasts had to be at least 36C, and the way they shifted when she moved you could tell they were real and she wasn't wearing a bra. The dress was so tight across her beautiful ass you couldn't see a hint of a thong at all. Dean was sure that she had nothing on under that dress.

As the short film played Kripke seemed to dote on her. He kept whispering in her ear, touching her arm, and sharing comments with her that brought faint smiles to her beautiful face. Dean guessed that they might be a couple the way Kripke treated her, and also by the Texas-sized diamond ring which was on her left hand.
Dean could not keep from staring at her, she was so beautiful. In spite of how Zia was dressed there was a very classy, very sophisticated air about her. She seemed very confident and very sure of herself. She caught Dean looking at her (hell, he was staring) a couple of times and she gave him a sexy little smile. He was so obvious in his admiration for her, that Katerina kicked him under the table a couple of times to redirect his attention.

Finally, when the promo came to an end, Katerina switched on the lights and took over the meeting like the pro she was. She pitched Kripke on a potential schedule and fee structure, and then answered several questions from the director about how the stunts were to be designed. Then Zia, while looking directly at Dean, asked if he would be designing her stunts and if she would be able to do some of them. Kripke immediately jumped in and said that his “baby was not going to be doing stunts. Her future was too precious to risk on reckless acts." As Kripke said this, Zia smiled at Dean and winked as if to let him in a joke.

The meeting soon came to an end and Kripke promised to make a decision soon. Everyone was getting up and saying goodbye, when Zia took Dean's hand. As her expensive perfume enveloped him she said, "I hope that we have a chance to work together. I think we would make an amazing screen team."

With that, Zia leaned in and lightly kissed Dean on the cheek. Her breasts pressed against his arm as she kissed him and whispered, "Bye, Dean." in his ear. She turned and followed Kripke out the door. Caught in the cloud of her perfume, Dean watched the sway of her beautiful ass walk out the door.

Dean's dream state was broken as Katerina smacked his arm and barked at him, "What the fuck were you doing?"

"What do you mean?" Dean asked as he looked over at her.

"Look, I know that you think you are God's gift to women, but it is not good business practice to eyefuck the client's fiancé right in front of him. How about business before pleasure, for once?"

"I wasn't undressing her. She came on to me." Dean stated.

"Do you think that maybe there is some woman on the planet that doesn't want your dick?"

"Yeah, maybe, but it wasn't her." Dean stated with a smug grin.

"God, you are so full of yourself." Katerina declared with a shake of her head.

"What? It's plain to see that she wants to give it away. I know that I would nail her during the first week of shooting." Dean stated with complete confidence.

"You are that sure of yourself?"

With her? I guarantee it."

Okay, I will take that wager. "

"What wager? You want to bet me that I can't nail her?" Katerina nodded in agreement. "Okay, what do I win?" Dean asked.

Katerina looked Dean up and down for a couple of seconds, then stated "A blowjob."

"What?" Dylan exclaimed. He could not believe what he had heard.

"Yeah, if you fuck her, you get a blowjob from me, but if you lose, you take me on a Rodeo Drive shopping spree."

"Rodeo Drive? That would be an expensive blowjob."

"What your wallet can't back up your dick? Or you don't think I'm worth it?" Katerina challenged him with a hard stare.

"I am not even answering that one. So, I just have to fuck her?"

"No, I set the terms of the bet. I have to think of the right situation, one with a time limit and a high degree of failure. I have no doubt that you could nail her if given enough time. Okay?"

Dean thought for a couple of seconds, the possibility of Katerina giving him head or dropping a few grand on a shopping spree? This was more then just a simple wager. There were all kinds of subtle levels and dangerous consequences if this went wrong. Not only was she his agent, he thought of her as a partner. Even if he succeeded, it could go very bad. Dean decided the payoff was worth the risk.

"Fine. If I get the job and you think of the right situation, I will take the wager."

They shook hands and went back to work. Dean watched as Katerina walked down the hall to her office. She had long beautiful legs that led up a very tight ass that she was wiggling with extra effort for Dean's benefit. The thought of fucking her was very intriguing. He had known her for about 5 years and she had never shown the least interest in him. He wondered what was up. Dean was finished for the day so he got in his prized 67 Impala and headed toward home. As he drove through traffic the memory of Zia's ass as she walked out the door was burned into his brain plus the added possibility of getting head from his beautiful long legged partner made Dean so horny that by the time he got home he needed some relief badly. He decided to go over to a local club called Caliente and see who might be at the bar.

As he walked into the bar area of Caliente, only one word would describe Dean. Stud. He was the poster boy for that much over used word. He was a very handsome guy at 6' 1" and 180 pounds of hard muscle with dark blond hair and piercing green eyes. He moved with the grace and power of a tiger. His tight t-shirt showed off a well developed chest and ripped forearms and biceps.

Apart from his physical beauty was his personality. Everyone liked Dean. Women wanted to date him and guys liked to hang out with him. He was fun, charming, smart and sure of himself. Dean knew who he was and what he wanted from life and was not shy about asking for it. His strength of character and leadership made him the focus of any room that he was in, even when he was not trying to be.

Yet, what set Dean aside from most other men was his package. He had a very impressive dick that was 9 inches long and 5 inches around with a large mushroom-shaped head. He had lost his virginity at 14 and he had not slowed down since. Very few women could resist his charms when he focused his persuasive personality on them.

As he surveyed the room, Dean quickly found his companion for the evening. She was a very sexy red head with big tits by the name of Anna Dresden. After buying her a drink and seducing her with a conversation filled with sexual banter and innuendo, Anna was putty in his hands and they left for his place. Fueled by Anna's very talented mouth and pussy, Dean had a very enjoyable evening as he relentlessly drove his nine inch monster cock deep into Anna's gushing pussy and clutching ass. After Anna had screamed herself hoarse and fallen asleep exhausted from multiple orgasms, Dean drifted off to sleep with his prick still buried in her hot ass.

The next morning, Dean cruised into the office about 10AM. He was starting to work out the stunts with the director of a new action themed credit card commercial that Dean had just gotten the contract for. As he headed back to the conference room, Katerina called him into her office.

His agent was a very pretty woman and she looked especially good this morning. Katerina was wearing a thin summer dress that clung to her tight athletic body. Her long blond hair was pulled back into a French twist and her smile lit up the room as he walked into her office. He had often wondered what she would be like in bed with her long legs, great ass, small perky breasts and not an ounce of fat on her body. Plus she was extremely smart with a film degree from USC and an MBA from Harvard. Katerina a killer business sense that had served him very well.

She was the kind of intelligent and confident woman that Dean found impossible to resist. He had been very lucky that she had taken him on as a client and he knew it. That was why Dean had never made any kind of pass at her. Katerina had been off-limits to him in his mind, but Dean had often wondered what she would be like in bed.

"Kripke's office just called and we have the contract. He is very excited to work with you. We have a few details to work out, but nothing that will stop the contract. I suggested that we have dinner tonight to celebrate our new enterprise, and he agreed. Are you ready to go ahead with the wager?"

"Sure, what did you have in mind?"

"Kripke agreed to bring Zia along. We are to meet at 8:30 at Vago. The terms of the bet are this, you must seduce Zia while we are having dinner with Kripke. You must seduce her right in front of him and convince her to fuck you. Kripke is not to have a clue what is going on. You don't have to fuck her there, but you must have proof that she is giving it up to you. Clear?"

"What kind of proof?" Dean asked.

"Her panties will do."

"So I am suppose to seduce Zia in front of Kripke, convince her to give me her panties, and show them to you for verification. If I do this, I get a blowjob from you. Is that the gist of it?"

"Yes, that's it. However, if you lose, I get a Rodeo Drive shopping spree on you. Agreed?" Katerina said as she looked into his deep green eyes.

"I just have a couple of questions. Why are you doing this? Why are you risking a contract with a producer by embarrassing him or us?" Dean wanted to satisfy his curiosity.

"You don't have to worry about that. There is no fallout for you. If this wager goes south, I will take full responsibility, okay?"

"And that is it? You're not going to tell me any more then that?"

"I have my reasons. If you get her, then maybe I will tell you. Do we have a bet?"

Dean looked at Katerina for a moment, at her blond hair, her blue eyes, her white teeth, smiling mouth and full sensual lips. The thought of those lips wrapped tightly around his thrusting cock as he came in her mouth was like heroin. Dean was hooked. Of course, he was going to agree to this. Dean knew that he could have Zia anytime. She had broadcast very clearly that she was available, but to do her in front of her man at dinner. Now that was a challenge that any player would rise to. His cock stirred in his jeans as thoughts of Katerina's mouth and Zia's pussy passed thru his mind.

"You have a deal." Dean stated with a smug smile.

"Good, I will see you at Vago tonight. Don't be late, Dean."

"I'll be there." Dean saluted her jauntily as he walked out of her office. This was crazy, but it was also going to be very interesting.

The Wager Act 2

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You bet your sweet ass I want more! UNF! Dean is a stone cold Stud!

I'd bet your sweet ass that there will be more Stud Dean!

I'm gonna go with Dean on this Wager! He's too hot to be stopped!

You're a smart lady to side with Dean on the Wager!

I definitely want more of your sexy player Dean!

I'll give you more, Baby!

I'm enjoying Dean's hot fantasy! He's a tiger! *roar* I want More!

Dean is a hot taut Tiger! I'll give you More!

You've got my interest! I really want to see how this goes for Dean!

I think Stud Dean has every ladies interest! Look for the update soon!

I have a strong feeling that Dean is gonna win that Wager!

I have a strong feeling Dean would like to meet you in the backseat of the Impala!

Your Dean is quite the playboy! Course with those looks who could resist his charms!

With that face and his impressive package no woman can resist!

I can't wait for more of this ultra hot fic! Love it!

Thanks for your comment Babe! There will be more!

Mmm...I just want to lick Dean all over! He is so YUM!

Dean wants you to lick him all over like now!

Dean is a very naughty boy! I like it! I want more!

He is a naughty guy and women love him!

There has got to be more of this! I hope you'll update soon!

I love that you're greedy for the verse! There will be more!

I really like how you write confident sexy Dean! MORE!

Thanks for that, Babe! There will be more!

  • 1

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