Fulton Prison Dean Mug Shot

Dean Winchester Caged

Fulton Prison Blues

Previous Entry Share Next Entry
The Wager
Dean Leaning against Bed

Title: The Wager – Act 2
Author: Deancaged
Pairing: Dean/Zia Nova, Dean/Katerina Kovia
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 lastest sexy scene features two 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 Banner Sexy B&W

Dean arrived at Vago about 8:15 PM. The restaurant was very noisy and crowded for a Thursday night. There was a long bar on the left as you came into the popular eatery. The rest of the room was full of tables and wooden booths along the walls that were enclosed. Each booth could seat four people and had curtains that could be pulled together to make the booth extremely private. Dean saw Katerina seated at the bar drinking a glass of wine when she noticed him and rose to greet him. His eyes locked onto her as she moved toward him. Katerina was dressed in a simple off the shoulder black dress that ended about four inches below her crotch. Her beautiful long legs were shown off to magnificent effect. She wore high heeled open toes sandals that allowed her red toenails to gleam. The dress clung to her body, molding itself to her breasts and slim hips. Her long golden hair was wrapped in a tight chignon on the top of her head with two tendrils on either side of her face softening the look and framing her face. Her blue eyes flashed at him excitedly as she walked up to him and kissed him lightly on the cheek.

"Are you ready to play?" She asked in a low husky voice.

"Well, let's just say that you should not be planning on that Rodeo Drive shopping spree just yet."

"Well, get ready Tiger, because here comes the prey."

Dean turned to see Kripke holding the front door for Zia. She was stunning as she entered the eatery, a beautiful young woman in a short pale pink sheath that clung to her in all the right places. Her long blond hair was worn down, her full breasts bobbed rhythmically beneath the dress. Her golden skin seemed to glow in the dim restaurant light. The click-clack of her heels reached Dean's ears, and he looked down, taking in her long, lean legs that ended in a pair of sexy open-toed heels.

"It is so good to see you again," Zia said as she hugged Katerina. Her striking smile lighting up her beautifully face, her green eyes sparkling with life. She turned to Dean and took his hand in hers, "I'm so glad that we are going to be working together." She smiled at him with an enticing smile, her full lips covered with shiny lip gloss.

"I'm looking forward to it as well," Dean said as he smiled down at her.

They greeted Kripke and arranged for a booth along the wall. They were told there would be a short wait, so they gathered in a far corner of the bar that separated them from everyone else in the restaurant. Kripke ordered them a bottle of Shiraz as they waited for their table. After the bottle had been opened and poured, Katerina began to engage Kripke in conversation leaving Dean and Zia to themselves. As Katerina discussed the film with Kripke, she maneuvered him in such a way that his back was to Dean and Zia.

Dean and Zia were deep in the corner of the bar pushed tightly together. She seated herself on a bar stool facing Dean with her back to Kripke and Katerina. Dean could see both of them very clearly over her shoulder. As she seated herself and crossed her legs, her short pink dress rode up high on her golden thighs giving him a glimpse of her black panties. Dean and Zia touched glasses together as they toasted each other. Zia leaned in closer to Dean because of the loud music and conversation, and her low cut dress made it seem that her ample breasts would spill out into his lap.

"I am so glad that you are going to be in our movie. I am really excited to be working with you. Have you been doing acting and stunt work for a while?"

"I've been in the business about eight years."

"I bet you will be able to teach me all kinds of things about dangerous stunts and difficult positions." As Zia said this, she reached out and gently caressed the back of his hand. Her light touch sent a shiver of delight up his spine.

Since this was moving even faster then he thought it would, Dean decided to step up the sexual banter. "Well, the length and width of my experience may surprise you."

"Oh, I doubt that. You have a very "big" reputation as a man of action. I have heard a lot about you. That is why I pushed Eric so hard to get you."

'God, she is forward,' Dean thought to himself. 'This is going to be easier then I planned. Katerina is going to be extremely pissed off.' He smiled to himself.

"What kind of experience do you have acting wise?" He asked.

Well, I trained in New York doing stage and I have done modeling work all over Europe. Film seemed like the natural progression. I am taking some acting classes out here now. “

“What kind?” Dean asked with genuine curiosity.

“Improv, role playing, and game playing. It makes you more spontaneous. More free to try new things. I really enjoy that.” Zia said in a deep purr.


“Yes, I like to make up situations in public and play them out in front of everyone. It is fun and dangerous.” Zia said as she licked her glossy lips suggestively.

“Do you have a favorite?” Dean asked as he glanced at her cleavage.

Zia leaned in very close to Dean's ear and whispered, "I like the one where the handsome young stud tries to pick up the pretty young girlfriend in front of her date, and fucks her silly. That is the game I really enjoy." As she pulled away from him, she uncrossed her legs leaving her crotch completely exposed to him. Dean looked from her lap up to her face. She smiled at him. "Do you want to play?"

Dean looked over her shoulder at Katerina and Kripke. They were both engrossed in conversation. There were other people milling about in the bar waiting to be escorted into the dining room although he suspected that they were too far away to notice. He put his hand on Zia's upper thigh and slid his hand up under her dress. She parted her legs a little wider. His finger tips brushed the silk of her underwear. He hooked his finger in the leg band of her panties and slid the back of his finger down over the very moist lips of her sex.

"That's it, handsome," she replied coyly as she crossed her legs trapping his hand between them. "I guess you do want to play."

Dean smiled at her and nodded his head. She uncrossed her legs and spread them just enough to allow him to remove his hand. His hand stayed and he continued to play with her clit rubbing it back and forth with the knuckle of his finger. A small moan escaped Zia's lips and her stiffening nipples pressed through the thin material of her dress. She pressed herself against his palm subtly.

"Uhh," another moan escaped her lips as Dean slide two fingers into the liquid warmth of her wet hot box. Zia grabbed her wine glass and took a big gulp. Her thighs parted a couple of inches more to allow him greater access.

"Mmmm," Zia moaned again as he began to rub her hot little clit with his thumb. She closed her eyes. All she could focus on were the fingers thrusting in and out of her. She began to rock her hips with the rhythm of his fingers. He continued to press hard against her rigid clit, driving her insane. Zia felt like she was going to cum. She felt it building in her stomach and spreading down through her burning thighs. It was going to happen! She was going to cum right in front of her fiancé!

Suddenly, the motion of Dean's fingers stopped and Zia opened her glazed eyes and looked up at him. Dean leaned into her and whispered seductively, "Go to the rest room and remove your panties. I want you seated next to me at the table waiting for my touch." As he said that, he withdrew his fingers from her wet slick pussy. Zia gasped at the sudden emptiness. He took his fingers and brought them to his mouth and licked them. She nodded and excused herself to go to the ladies room.

Katerina glanced at him as Zia left, he simply shrugged his shoulders. Kripke turned and began to talk to him about some ideas that he had for stunts for the film. Zia returned a few minutes later and took her seat, but Kripke was now talking to both Katerina and Dean. Soon their table was ready and they moved out into the main dining room. As Zia passed Dean, she furtively pressed into his palm a piece of soft material. He looked down to see it was a black silk thong. He balled it up in his hand and brought it to his nose to sniff her exotic and musky scent before he slipped the thong into his coat pocket.

The host showed them to an enclosed booth along the back wall. Their booth had curtains along its front that could be closed to create a very private and intimate enclosure. Kripke was seated on the aisle on the same side with Katerina, and Zia sat on the inside next to Dean. Kripke ordered hors d'oeuvres for the table and a bottle of Cristal. The conversation was light as they chatted about the movie and people that they knew in common. Zia's knee kept rubbing up and down Dean's thigh every few moments.

After the champagne had arrived and they had ordered, Kripke requested from the waiter that the curtains be closed. When this was done the only light in the booth came from a small candle on the table. Dean thought to himself that this set up could not be any more advantageous to him and his mission. Kripke proposed a toast to their movie and partnership, and they all touched glasses. Dean felt a hand creep into his lap and search for the hard bulge in his pants. The hand squeezed his hard cock and moved down his leg searching for the end. The hand squeezed two more times before the end of his swollen rod was located. Zia glanced at him with a look of surprise in her eyes, and Dean just smiled at her. She quickly reached for her champagne flute and took a long drink.

"Honey, don't drink so fast. This is an excellent champagne. It should be savored." Kripke instructed Zia.

"Sorry, Baby," Zia demurely answered.

While this exchange was happening, Katerina looked at Dean and nodded her head in Zia's direction. Dean smiled and nodded affirmatively. Katerina's eyes darkened for a second, then she turned in her seat toward Kripke and grabbed his arm. "Eric, I have always wanted to know how you got started in producing. How did you decide to do this for a living?"

As Kripke turned his entire attention to Katerina and began to prattle away about his career, Dean cautiously slipped his hand into Zia's lap, and between her legs up to her dripping slit. His middle finger parted her lips, and he felt her wetness. He began to caress the hot wet folds of her over heated pussy as Zia licked her lips and leaned forward in apparent fascination at Kripke's description of his career. The look of intense concentration on her face was betrayed by her pert nipples that were straining against the sheer material of her dress. Dean swirled his finger over her very slick little clit which made Zia tremble with delight. The fear of discovery and the risk they were taking was an intense turn on for both of them. The thought of him feeling her up right in front of Eric was driving her wild. Her control over herself was slipping as Dean continued to gently rub her rock hard clit.

"So I sold my first production company to Lionsgate Entertainment for about five million dollars. And I used that money to produce my first big budget action flick, Rapid Fire. It made about twenty million dollars in the theaters, but fifty million in DVD sales. I used that money to set up my own studio, " Kripke explained to Katerina who was trying to look interested. Dean slowly pushed his middle finger into the slick tunnel of Zia's steaming pussy. He repeated this movement ever so slowly. In and out and in, then circle her throbbing clit every few times and start all over again. Zia's eyes were dark with desire and her breath came in shallow gasps. She was holding on to the table white knuckled to keep from screaming with pleasure. Her pussy was leaking like a faucet as she felt a huge cum building inside her.

Zia needed release desperately and was almost becoming frantic in order to get it. She reached into Dean's lap and began jacking his hard cock through his pants under the table. Suddenly, Dean plunged two fingers up to the third knuckle into Zia's dripping velvet box and felt her molten walls clamp down onto his invading fingers. Her orgasm hit her like a ton of bricks. She slumped back against the booth and threw her leg over Dean's knee. Her hips began to thrust upward trying to drive his fingers deeper into her burning hole. If the table cloth had not hidden her movement from view, Kripke would have been able to look right into his fiancé's wide spread pussy cumming all over Dean's thrusting fingers. Zia brought her napkin up to her mouth and pretended to cough to cover her moans of release. Dean felt her climaxing pussy muscles ripple up and down his fingers as they tried to pull him in deeper. The suction was so great that he had a bit of struggle trying to pull his fingers out without drawing attention to the movement. As his fingers left her fiery cunt, she gasped and leaned forward. She clamped her thighs together tightly so she could squeeze one more little climax out of her over heated pussy.

"Are you okay, darling?" A concerned Kripke asked.

"I'm okay, Baby," Zia coughed. "I just feel really hot all of a sudden. I'm going to the ladies room. Please excuse me."

Dean stood and pulled the curtain aside. Zia got up hurriedly and fled toward the bathroom. He looked after her retreating figure and knew that he had won the bet. He had her panties in his pocket and her cum on his fingers. He could stop right now and get his blowjob from Katerina, but the throbbing nine-inch monster that was half way down his thigh was telling him to do something different. He looked at Katerina and winked suggestively at her.

"Please excuse me Eric, but I have to make a call. I'll be back soon." He put the curtain back in place and moved quickly toward the restrooms with a smile on his face.

The Wager Act 3

  • 1
The way you write Dean here makes him so sexual and incredibly hot! Zia is a lucky girl to have all that directed at her!

Dean enjoys being a player with the ladies! Zia is just the next in line to be consumed by his hotness.

I would love to meet Dean and play with him like this! Ultra Hot!

I think Dean would be on board for that!

OMG! I can hardly breathe! That took my breath away it was so dirty bad wrong and hot! Dean is a lady killer! No doubt about it!

I am very pleased that Dean took your breath away! He tends to have that effect on women!

I would do Dean anytime and anywhere even in public!

Bring it on Baby! Dean's ready for you!

UNF! Hot! Dean is a total player and on fire!

Dean does tend to set the ladies on fire!

OMFG! All I can say is MORE!

I've heard of private booth restaurants but I've never been to one! That was incredibly naughty and hot!

I haven't been either. Maybe we should try it together.

Very Hot! I want more!

Have you ever done anything like that in a restaurant? Just curious. You wrote this very well!

It wasn't in a restaurant, it was at a movie theater that was a sold out crowd!

Dean is definitely winning the Wager! I'd say he's gonna win more than Katerina first bet!

You were backing Dean right from the starting line, smart girl!

Dean sure isn't shy course neither is Zia! They are both shameless and totally hot for each other!

You're right Dean isn't shy but he is shameless! You'll find out just how shameless next post!

I can't wait for more stud Dean!

There will be more stud Dean very soon!

Whew! This just gets hotter and hotter! I'm looking forward to part 3!

Dean is going to burn up the screen in part 3!

  • 1

Log in