Conquering Christmas

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David Blake examined his reflection in the bathroom mirror. His hair was neat and combed and cut in the latest style and his face was cleanly shaven. David smiled at himself as he stepped backward and away from his reflection. He did a half turn to admire how his suit fit and couldn't suppress a grin. He was looking good as always and knew it.

David exited the bathroom and strolled down the hallway of the hotel. The company had gone all-out this year, and the annual Christmas party was a spectacle to behold. David enjoyed the holiday season, but loved the company Christmas party most of all. In ten years with the company, he had never failed to score. David was a natural charmer and had used it to his advantage in both is professional as well as his personal life. He had bagged his fair share of secretaries and executives alike, and the Christmas party was the best time of year to increase his number of 'Conquests' as he liked to refer to the women he slept with.

This year's target was Penny Peel. She had only been with the company for a few months, and David almost salivated whenever she walked past his office. She was a vice president in the marketing department, with her office only a few doors down from his own. He chatted with her occasionally, but had made it a point in the past few weeks to see her as often as possible. He didn't talk much about himself, but instead turned the conversation toward her. He wanted her to feel that his interest in her was genuine. It was all part of his plan.

Now the company would never approve of such coupling between employees, and it worked to David's advantage. No woman ever wanted her reputation sullied, or thought of as a slut that slept around. This kept them quiet, and left all the other women oblivious to David's scheme. To be fair, David was not a selfish lover, and none of these women ever left the party less than satisfied. He just did not want a permanent relationship, and enjoyed the thrill of the chase.

The party had been jumping for over an hour, and many of the partygoers were already feeling tipsy. David had personally fetched Penny three drinks, and knew that she was well on her way to losing what inhibitions she may have. She had touched his arm and smiled as he excused himself to the washroom, and her smile hinted at what he knew she wanted. Yes, as usual, life was looking good for David Blake.

David took his time as he walked across the floor toward Penny. He drank in every curve of he body as if it were a fine wine. She was petite in stature, but with a figure shaped like an hourglass. Her had full hips and a plump ass, while her breasts were the size of large, ripe peaches. Her face was both childlike and experienced all at once, and her black hair fell around her shoulders in thick curls. Penny had told him how much she loved the holidays, and it was obvious by how she dressed for the party.

Penny wore a short red dress with a white trim that made her look like the wife of Santa Clause. The dress was short enough to show off her shapely legs, and the shimmering black stockings that encased them. David purred like a cat as he watched her. She was the belle of the ball. She smiled as she saw him coming, and David could see the warm flush that had crept onto her face. She didn't wait for him to finish coming to her, but met him halfway.

"I think I've had enough to drink, and getting drunk around the bosses isn't the smartest thing to do." She said, her speech sounding a bit slurred. It was just the opportunity that David needed.

"I always rent a room for the evening. That way I don't have to drive if I drink too much. Do you want to go up and sit for a while until your head clears?" He offered as if a concerned friend.

Penny swayed for a second before she focused on the question at hand. "Sure, we can chat and maybe have a few drinks from the minibar." She said finally with a wide smile. It was a smile that reflected on David's face, but for a different reason.

Penny chatted continuously as she and David headed to his room. She was not usually so verbose, and David took it as a good sign that she had become intoxicated. She giggled and leaned against David's arm as they walked, and he could feel the soft globes of her breasts press against him. He never failed to pick the right woman, and his streak was not about to end now. He couldn't hide a grin, knowing that within a few minutes, Penny would be on her hands and knees with his hard cock driving deep into her sweet cunt.

When they reached the room, David untangled himself from Penny to fish the room key from his pocket. He watched as she headed straight to the bed and flopped down on her back. He took a second to gaze at her. She lie with her back arched and her legs spread wide enough for him to see that her pantyhose were without the cotton crotch pad. It was also clear the liquor had affected more than her inhibitions, as he could see a thick stream of creamy girl-juice oozing from between her pink pussy lips. This was by far his easiest and possibly his hottest conquest.

David moved toward the bed, but Penny sat up before he reached her. She looked as if she didn't recognize him, but then broke into a silly, alcohol-induced smile.

"I think I want another drink. Could you go and get some ice while I check what's in the minibar? When you get back, we can have another drink and get more comfortable." She asked again with slurred speech.

David agreed and grabbed the ice bucket. He hated paying the ridiculous prices of the minibar, but it was well worth it for everything else he was soon to get. He left the room with a spring in his step, but grew frustrated when he found the ice machines on his floor to be out-of-order. He finally went to the floor below and filled the bucket before hurriedly making his way back to his room.

Penny had kicked off her high-heeled shoes and prepared two drinks while waiting. She took a cube of ice and dropped one into each glass before handing one to David.

"You make me feel like a lush Dave. I can't remember how many drinks I've had tonight, and you've barely drank anything. A girl doesn't like to drink alone." She said with a waggle of a finger and her now constant smile.

David tipped his glass in her direction and down his drink in one gulp. It was tequila, and not his favorite liquor, but it did bring a pleasurable warm that spread from his face down to his groin.

Penny smiled as she downed her drink as well and then sat the glass on the bar. She fell back onto the bed, and balanced on her elbows. Her legs were once again spread wide, and her pussy looked even more inviting.

"I don't usually sleep with guys from work, but it's been a while since I've enjoyed a good romp. What would I have to do to convince you?" She asked David whose cock was rapidly rising in his pants. He moved toward the bed, but she stopped him with a shaky foot that she pressed against his growing member.

"I think may have already convinced me." David said with a shudder as Penny stroked his cock with her soft, warm foot.

"If that's the case, then how about giving my poor little pussy a kiss? Nothing gets me going like a man who can use his tongue. You can fuck me however you want after that." She said, and David was all too quick to comply.

David slipped down to floor and slid his hands up Penny's legs. He pushed her dress up to reveal the wettest pussy that he had ever seen. Penny must have been horny before she started drinking, because sticky cream coated her pussy and had soaked the thighs of her pantyhose. Her clit was stiff and crimson as he gave it a light flick with his tongue. The scent of her arousal filled his nostrils, and it was a heady, musky smell that made his cock scream to be free of its confinement.

David began to lap at her sticky slit, covering his face in her cream as her hips wiggled in appreciation. Penny lie back, and grabbed his head in her hands, and he let her run her fingers through his hair. He was feasting on her succulent flesh when he felt the first wave of dizziness. His face was hot, and his cock was throbbing and the feeling went unnoticed, but he first one was undeniable. He felt strange, and tried to pull away, but Penny's soft stroking hands hand become demanding and firm. She held him in place and thrust her hips up at him, dragging her creamy slit across his mouth.

The room as spinning, and David struggled to free himself, but his strength rapidly faded. He could not even move his tongue, but Penny used his unresponsive face to achieve her orgasm. David could hear her moans of ecstasy as she orgasmed, and the last thing he felt before he slipped into unconsciousness was the wet spurts of her climax cascading over his lips and into his open mouth

David awoke as if he had been sleeping for ages. His mouth felt like it was full of cotton, and his feet were cold. He instinctively tried to swallow, but found himself gagged with a cloth, which barely let him move his tongue. He instantly snapped back to reality when he realized that he could not move his hands. His eyes snapped open and he found himself lying face down on a bed that was not his own. He could see that his arms stretched above him, and that heavy ropes around his wrists bound him to the frame of the bed.

David became frantic as he tried to move his legs, and found that they were also firmly attached to the bed. He struggled for a few seconds and then realized that it was useless. He could not get away, so he set about piecing together what had happened. He had a dull ache in the back of his head, and it took him a few seconds to start thinking.

The last think that David could remember was inviting Penny to the room. He had been lustily devouring Penny's shaven cunt when he blacked out. David steadied himself. Someone must have been hiding in the room and knocked him out when he became preoccupied with Penny. They must have robbed him and tied him down before making their escape, but what about Penny? He tried turning his head, but from what limited view he had, could not see her anywhere.

David tried to make sense of what was happening. Had the robbers kidnapped Penny, or worse? If that were case, then why leave him alive? A cold dread crept through David as he began to imagine all sorts of possibilities. Maybe they had already killed Penny and were disposing of her body, planning to kill him next. What if they had killed Penny and left him to be the fall guy? David's heart was pounding in his chest as he frantically searched for an answer.

The sound of the door lock pierced his panicked mind, and David screamed as loud as he could, hoping that someone outside the room would hear him. The effort proved useless, as the gag in his mouth prevented the full force of his voice from escaping. His nostrils expelled air like a racehorse as he looked towards the door. Whoever had entered the room, took their time, and David could hear the sound of running water in the bathroom.

The running water quickly stopped, and David felt relief when Penny stepped into sight. She must have escaped the robbers, but why had she stopped in the bathroom? David grunted and shook his head, trying to let Penny know that he was all right and that she could release him. He kept doing so for a few seconds until he saw the smile on Penny's face. It wasn't the sloppy smile of a drunken partygoer, nor the relieved smile of an escaped captive. No, Penny wore the satisfied, smug smile of someone who had just executed a well-laid plan. She moved to stand by the bed, and David had to strain his neck to continue to look at her.

"I'm so glad you've finally awoken Dave. I was beginning to get a little impatient." She said, in which David responded by straining against his bonds and yelling as loud as he could.

David's eyes closed as he raged against his captivity, and did not feel or see Penny as she dropped to the floor next to the bed. Penny caught him off-guard as she seized a handful of his hair. She jerked his head back brutally, and smacked him hard across the cheek. His body jerked at the strike, and stars filled his eyes.

"Shut up Dave." Penny growled. "The rooms adjoining this one this one are empty, which means that not only is it secluded, but there won't be anyone even passing by the door. I hope you're as smart as you think you are. I'm looking forward to an exciting evening, and you need to understand before we start, that you can either fight, or enjoy what's going to happen. It's as simple as that."

Penny released David's hair and stood. She began slowly walking around the room, coming and leaving his field of vision. She talked as she moved, and a lump grew in David's throat as she explained what was going on.

"You see Dave, I am not helpless little lady who can't hold her liquor. I'm not a big drinker, and in fact I only drank one of the glasses you brought me tonight, but I can hold my own. I am also not one of your conquests. Yes, I do know that is what you call the women you seduce at the annual party." She explained slowly.

"I also know that you are not the kind of guy who is looking for a deep relationship. Hell, I even know from the other ladies that you are one hell of a screw. But, what I am the most certain about, is that you do not play fair." She said. She stopped walking and stood where David could not see her.

"I caught on to your game early, and it didn't take too much asking to find out about you. I was able to find that you have tallied up an impressive list of conquests over that past few years. I'm not vain, but it was obvious that you intended me to be your latest little fling, so I spoke with some of the ladies around the office, and I came up with a plan. I think it's about time for a little payback." She said, and then returned to walking around the room.

"Now before you start panicking, I want you to know that I won't do anything to harm your position in the company. After all, I would have as much to lose as you if word of any 'activity' leaked out. But, as good of a fuck you may have been to the other ladies, it has always been a one-sided affair. I like variety in all aspects of my life, especially during sex, and I plan to make this year's party memorable for everyone involved." She explained.

Penny moved around the bed and began adjusting the ropes. David was sure that she was going to let him loose, and then he could make his escape. She was right in that word of this would ruin both of them at the company, but he would find a way to get back at her. He prepared himself to move as soon as he was free, but the opportunity never came. Penny pulled the rope, and a coil around one of his knees pulled his leg underneath him. She secured the rope and then repeated the on the other side of the bed. David now found himself on his knees with his ass poised like a target in the air. Penny pulled on another set of ropes, and his ass lowered, but at the cost of his legs spreading like a biology lab frog.

"That's perfect." Penny said as she stood back to survey her work. David's limp cock and balls swayed between his legs, and she reached out to stroke him. He jerked as her hand circled the base of his cock, but couldn't move. His body was tense as she began slowly stroking his shaft, and to his amazement, as his cock began to harden.

Penny stroked his prick until he was hard and throbbing, and his body was shaking with excitement. She felt his shaft throb, and quickly pulled away, causing him to moan in frustration. She moved back to watch his hips jerk, and his swollen cock bob in frustration in the empty air. A thin string of clear syrup hung from the tip, but he had not found his release.

"No, no we don't want you coming just yet. I want to make sure you are good and ready for what's to come." Penny explained.

David groaned, but sighed when he felt her hand moved back to his aching cock. He thought that she had changed her mind and would finish him off, but instead her felt something hard pressing against his shaft and around the base of his balls. The pressure increased until her hands moved away, and David could feel a heavy ring wrapped tightly around the base of his cock and balls. His shaft now felt even thicker, and he could feel it throb with every beat of his pulse.

"Now we can begin with the prep work." Penny said in a voice that was all too chipper for David's liking. He heard her moving around behind him, and then heard the faint clicks of a bottlecap unscrewing for the first time. He was so intent on trying to listen that she startled him by touching his leg. She ran her hand up his thigh, and then began slowly rubbing the cheeks of his ass. Woman had grabbed his ass plenty of times while fucking, but never in such a slow and caressing way.

David had just grown accustomed to Penny's touch when her second hand entered the scene. She slid her thumb between the cheeks of his ass and slowly moved downward. Her digit was slippery, and David could feel a trail of cool gel left in the wake of the traveling appendage. He tried to move away, but again had no success. He struggled and tried to kick, but Penny ignored him. Her thumb pressed firmly into the center of his ass, and David tensed his muscles in an attempt to stop her.

"I told you that you could either fight or simply relax and enjoy yourself. I'm still going to get what I want, and it's up to you if you are comfortable or...uncomfortable." Penny explained. She punctuated the last words of her sentence by firmly pushing her thumb against David's ass. He yelped into the gag as the tip of her digit forced the resisting iris of his ass open.

"Now, I hope you can see how right I am. No matter how hard you fight me, I am still going to get what I want." Penny said as she pulled the tip of her thumb from between his cheeks.

David knew that she had not given up, and did not jerk when her thumb returned with a fresh coating of slippery gel. He tried to relax as she rubbed her thumb against the tight opening of his ass. He concentrated on breathing and tried to take his mind off what she was doing, but could not ignore the warm touch of her finger as she drew soft circles on his relaxing hole. He had never let anyone play in that area before, and could not deny how pleasurable the sensations were.

Penny continued to work on David for the next few minutes, and he did not even flinch when the pressure of her thumb increased, and she began dipping the digit into his now relaxed hole. David gasped more from surprise than anything else when she slipped her full thumb in his ass, and shivered when she continued the same spiraling massage along the walls of his virgin anal chute.

"There we go. I bet that feels good, doesn't it?" Penny asked rhetorically as she continued to finger David's ass. She moved her other hand to join the one pressed between his cheeks. She slid her second thumb along the first and slowly began slipping into his ass. David was soon feeling full and stretched, but his relaxed sphincter easily accommodated the second digit. Penny began rotating both thumbs in opposite directions, and David began to shake from the sensations. His cock was oozing a steady stream of clear liquid that was creating a small puddle on the bed.

Penny continued for a few more minutes before she slid one, and then the other free from David's relaxed hole. His hips bucked at the sudden emptiness and he groaned loudly into the gag. He was so overcome that he did not notice that Penny had not moved from her position, and quickly silenced when he felt the rounded tip of something pressing against his now willing nether-hole. The object felt well lubricated, and the tip easily glided past the compliant muscle. The object became wider as it went, and just when it threatened to become uncomfortable, it became thin and the object popped into his anal passage.