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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.

David groaned, as what he could now tell was a butt plug filled his rectal canal. He felt full, and the weight of the plug pressed against his prostate, causing his cock to jerk and leak even more of its sticky syrup. Penny gave his cock a few soft strokes before pulling away from the bed.

“When I’m right, I’m right.” Penny said with a chuckle as she walked around to the side of the bed. She ran her hand down David’s exposed back, and came back damp from his perspiration.

“I knew you’d enjoy it, but don’t tire yourself out, the night is still young and there are plenty of things to do. I’m trusting that you will play nicely now, so I am going to remove your gag. Do we have an understanding?” Penny asked David, who was watching her from under a sweaty brow. He weakly nodded, and lie still as she unfastened the leather strap from behind his head, and pulled the piece of cloth from his mouth. David worked his stiff mouth and ran his tongue over his lips. He could still taste the remains of her orgasm.

“I’ll give you a drink before we continue. I took the liberty of having a bottle of champagne delivered. I’ll split the bill with you.” Penny said nonchalantly. David knew that she may have removed the gag, but also that she had no plan of releasing him yet. He waited as she left his view, and she quickly returned with a bottle of champagne. It was an expensive brand, and he wanted to yell at her for clearly charging it to his room, but quickly rethought the idea.

Penny climbed onto the bed and slid down in front David, positioning his head between her legs. She pulled her dress up and tucked it behind her, once again exposing her creamy, wet pussy.

“Now I’m not ready to untie you yet, so I can’t give you a glass. But today is your lucky day, and I’ll let you drink from something much better than a glass.” Penny explained to David as he gazed up at her.

Penny took the bottle of champagne and held it a few inches above her clit, and David instantly knew what she was planning. She tipped the bottle and drizzled the cool liquid down over her vaginal valley. She shivered as the chilly bubble cascaded over her stiff clit, and David quickly maneuvered his mouth to catch the bubbly waterfall. He lapped like a puppy at her pussy, the taste of her salty cream mixing with the tart champagne.

David scooped his tongue between her folds and sucked down the intoxicating elixir, but it ended far too soon for his liking. Penny let him finish cleaning her swollen pussy before sliding once again from the bed. She returned the bottle from where it came, and reappeared before him.

“I’m going to bathroom for a few seconds to get ready. Please remember that we are on the honor system. I would hate to have to replace your gag.” Penny said before turning and leaving the room.

David was a mass of conflicted emotions. He was still angry about Penny drugging and tying him up, but he could not deny that she had not done anything harmful. In fact, he had to admit that she was doing things to him that he would have never considered, and he was enjoying it. Here he was, tied to a bed on his hands and knees, with a butt plug deep in his ass, and a metal ring keeping his cock hard and throbbing. He didn’t know what to make of the situation, but his thoughts ceased when Penny emerged from the bathroom.

It wasn’t that she had removed her dress and now wore a festive red bra and stockings trimmed in white fur that left him speechless. It wasn’t that she was smiling at him from under a red Santa hat with the sexiest look that he had ever seen as she slowly crossed the room. What left him unable to speak was the crisscross of leather straps around her waist, and the realistically shaped red and white, candy cane patterned cock that stood out from her succulent pussy. It bobbed rhythmically as she walked, and as she came closer, she took it in one of her hands and began stroking it slowly.

“I know what you’re thinking. ‘There’s no way she’s going use that on me’.” Penny said as she stopped and gave him a view of her profile. David looked at her with a mixture of lust and dread. She was sexy in a perverted way that he had never imagined. He would have been all for the scene if she were planning to use her new appendage on another woman, but he was not happy that it was he that she wanted to fuck.

“You’ve been on the naughty list for some time now, but yet you have still been getting your Christmas presents. I think a little accounting is in order. My job as Ms. Claus will be to help you give a little back for your years as a bad boy, which will put you right at the top of the nice list.” Penny explained cheerily, doing her best impersonation of the wife of Santa Claus. Unfortunately, David did not find her acting or his position to be humorous.

“Look, I think you’ve made your point. You can let me go, and we can forget any of this ever happened. I’m sorry.” David blurted out, finally finding his voice.

“So, you’re sorry that you tried to have sex with me? Are you saying that I was some sort of a mistake?” Penny asked, her voice rising as she spoke. She stood with her hands on her hips and glared down into David’s face.

“No, I’m not saying that. I’m just saying that I was wrong to treat you in such a way. My only concern was myself, and I’m sorry.” David said in a rush to clarify hiss earlier statement. Beads of sweat were poring down his face as he tried to come up with anything that might get him free.

“I’ll even find out a way to make it up to the other woman who I’ve wronged. I promise, I’ll change. I really will.” He pleaded.

Penny’s face softened as she considered what David had said. Everything would be fine if he were truly going to change his ways. She finally gave him a nod and began twisting the knots of the ropes that bound him to the bed. David allowed himself a sigh of relief as he felt the ropes keeping his arms stretched begin to loosen. He found his relief short lived as Penny quickly retied the ropes.

“But I thought…” David began to speak.

“You thought I bought all of that shit you were selling? No way. I just needed to adjust your arms so I can really pull you back once I get going.” Penny said with a chuckle. “Don’t worry Dave, you’re going to enjoy it. When I’m done, you’ll be ready to service a whole team of Ms. Clauses.”

David struggled again with all of his might, hoping that her lengthening of his bonds had weakened the knots. He found that despite his extra few inches of freedom, he could still not break free. Heavy bolts secure the bed frame to the floor, and the ropes were as secure as when he first awoke.

Penny let him work out all of his frustration before she continued. She started by gripping the base of the butt plug, and David immediately fell still.

“There you go, now let’s get rid of this.” Penny said as she began slowly pulling the plug from David’s ass. He clenched his hands into tight fists as the plug began to move. The tight walls of his anal canal grudgingly let go, and he shook as the smooth orb began to expand his anal ring. The tight opening expelled the plug with greater ease than it had accepted it, and David gasped from the sudden feeling of emptiness.

“You are a natural Dave. This little hole of yours is so hungry that its gaping open and ready to for more.” Penny said as she gripped the cheeks of his ass, spreading him so she could get a better view of his still open hole.

“Please Penny…” David began, trying to reason with her once more.

“See Dave, I knew you’d be asking for it.” Penny said with a laugh.

David tried to plead again, but before the words came out, he felt Penny’s full weight settle onto the edge of the bed behind him. He felt the head of her rubber cock press between his cheeks, and the tip pressed firmly against his once tight ring. Penny grabbed his hips firmly in both of her hands and began slowly rocking against him.

“Just relax. We’re going to take it nice and slow. I don’t expect you to take the whole thing at once, but I’m confident that you’ll be riding like a champ before I’m done.” Penny said. She watched as the red tip of her cock began to force David’s ass open even further. The rim of the wet hole expanded with every increasingly deep thrust, and David moaned, as she slowly speared him open.

David gasped as the head of the cock finally slipped past his expanding sphincter. He expected Penny to push further, but she pulled back just enough for the head to pop free and then quickly pushed it back in. His hands gripped the sheets and he shook violently as Penny repeatedly slid his tight hole over the ridge of her cock.

“I call this ‘Popping’ Dave. The ring of your anus is full of nerve endings, and this gets it hot and sensitive. I want to make sure you get the full effect when I’m pounding this baby home.” Penny chuckled. Penny continued rocking the head of her cock in and out of David’s ass for a few minutes longer. Just as she had explained, the ring of his ass became so sensitive that a stream of continual moans escaped his mouth unchecked. Whether by pleasure or because of the ring, his cock remained rock-hard and continued to leak heavily onto the bed.

“Are you ready for more?” Penny asked, but did not receive a reply. David’s mind was so clouded that her words registered, but the came slowly and fragmented.

“Dave?” She teased, drawing his name out like coaxing sex kitten.

“Should I keep popping this hot little hole or do you want more?” She asked, leaving him trapped. The ring of his ass was sending explosions to his head, but he didn’t know if he could take any more, especially if this was an indication of her skill at fucking. He tried to analyze the situation, but quickly surmised that she would eventually fuck him, and other than acceptance on his part would only prolong his ordeal.

“More.” He said softly, resigning himself to what would come next.

“I couldn’t hear you Davie. What did you say?” Penny said with a flick of her hips that popped the head once again past his burning ring.

“More please.” David said with a little more volume in his voice.

“Okay, so you want more. But what do you want more of?” Penny said as she popped the head out.

“More of you.” He said, not wanting to say what he knew she wanted to hear. His response prompted her to jerk again, slipping the head back inside again.

“More of me? Come on Davie. It’s true that I’m doing the driving, but tell me what you really want. Tell me where you want it.” Penny said, and he could hear the sneer that twisted her lips.

“Please give me your cock. Please put it deep in my ass.” He said, the last vestige of will leaving him as he spoke.

“I knew you would be unable resist long. You are going to so love it when I get going.” Penny said. She popped the head out once more, and pulled away enough for David to catch a cool rush of air across his backside. He could feel the cool air as it flowed into his open ass like it was blowing through a canyon. It was odd yet soothing, but he barely had time to enjoy the relief. He felt Penny’s fingers and a cold ointment touch his twitching ring, and shuddered as she spread the soothing gel.

“This will make sure that you can enjoy everything without now becoming too sensitive. It has a mild anesthetic quality, so this little snapper of yours will stay relaxed. David could only relax as she spread the ointment around the outside and then inside his pulsing portal. He waited as she pulled away again, and when she returned he felt another cylinder sliding into his ass. This one was much thinner than the plug or the head of the dildo, and he could not tell what it was until he felt a cool rush of liquid filling his hot, anal cavity. Penny removed the tube, and then returned to fill him with the liquid for a second and then a third and final time.

“Now, I want you push like you’re going to the bathroom, but only a little. The smallest push you can make.” Penny directed him. David complied and bore down with as little force as he could. A slight numb sensation had spread over his slack anal opening, and he found it difficult to gauge just how much he was pushing. He pushed, and felt a small dollop of the liquid bubble from his ass.

“That’s perfect Davie. Good boy. Now your all ready for the ride of your life.” Penny said as she gripped his hips, which she began squeezing firmly.

David braced himself for what was coming and soon felt the round tip of her cock pressing against the now-primed opening of his ass. He felt more pressure than anything now, but could feel the head opening him once again. He didn’t wince when the head popped in, but he groaned like a banshee as Penny kept pushing forward. He could feel the head leading the charge, pushing his rectal walls apart, making way for the thick shaft. The pressure and fullness built, and he could feel every inch as the cock filled his anal tunnel. He felt the excess lubricant leak from around the thick shaft and shook uncontrollably.

“Come on Davie, there’s just a little more. I know you can take it.” Penny cooed. She slowed reached under him, and after a bit, gripped his cock in her hand. She gave him long, firm strokes, and as he gasped in torturous please, she slid the final inches home.

David let out a moan that would have woke the neighbors if there had been any. His body instinctively jerked upward, and though not far, it drove him further back onto the invading cock.

“That’s it baby.” Penny growled. She ignored his jerking and thrashing. She could feel his ass as it convulsed, sending ripples down the rubber cock. She pulled out a few niches and then slid back in, causing him to jerk even harder. She pulled back further the second time and even further the third. She continued until she was stroking all of her cock into his ass, almost clearing the head on each withdrawal.

David’s legs had grown weak, but the ropes kept him from sliding down. His muscles were all but useless as Penny rocked him back and forth like a rag doll. He could hear the slight squelching noises flowing from his ass as Penny pounded into him. He felt as if he would black out at any moment, but clung to consciousness. She rode him for what felt like hours before he felt her hand on his cock once again.

“You’ve earned your release.” Penny said as she gingerly unfastened the ring that was binding his cock. He winced as his circulation returned to normal, but his confusion overshadowed his relief. She was going to release him, yet he still had not come. He could feel her cock buried deep in his ass, he had taken more than he had ever given, and yet she was releasing him without an orgasm. He felt as if he would burst.

“What about me?” He asked. His voice came out tired and weak, but held an undeniable edge of need.

“I haven’t come. I need to, so badly.” He said, his words coming out in a croak.

“I know, and you will, very soon.” Penny said. He could feel her move, but was too tired to move. He didn’t feel her release one of the ropes, giving his arms even more freedom. It was far too late to escape, as he didn’t have the energy, and his arms felt like lead. David’s body was limp, but bending over and placing her hands under his chest, Penny had the strength to hall him upward. Once he reached a certain point, his own weight took over and tilted backward, his weight driving the cock as deep as it would go. He gasped at the sudden fullness and pressure on his prostate.

“Do you want to come?” Penny asked.

“Yes. Please may I come?” David responded, his voice eager and pleading.

Penny chuckled and gripped his cock once again. She slid his hand smoothly down his shaft, coating it with his own slippery syrup. She stroked slowly at first, while she matched each stroke with a thrust of her hips. David threw his head back in a soundless moan as she primed his prostate. His whole body shook as he felt his cock throbbing, and his stomach tightening. He had never experienced such an orgasm, and it was almost frightening.

David shook, as his body began to betray him. The muscles in his legs found a last burst of energy, and they tightened and released in violent pulses. His stomach muscles cramped as his arms became rigid. Penny timed her thrusts and strokes with his body’s rhythm. His cock was oozing like a volcano, coating her fingers in creamy semen.

David finally reached his peak, and exploded as if it were his last orgasm. His cock was painfully hard, and he felt every stroke of Penny’s fingers along the straining veins. While his stretched ass felt every detailed vein along her hard shaft. He felt as if he was pouring out the essence of his being, but his body would not stop. His breath came in short snorts like a crying child and his cock continued to jerk even after Penny stopped moving.

David began to swoon, and was barely aware when Penny pushed him forward and back down on the bed. He had already slipped into unconsciousness when she pulled the slippery cock from his well-worn ass. Much to Penny’s amusement, the plug she had used before would no longer stay in place, so she improvised by removing her harness and placing it on David. She slipped the cock back into his ass and secured the straps, making everything would stay in place.

David awoke again to find himself on his back. He tried to move, but found himself still tied down. Even more, he could feel the thick weight of Penny’s cock still buried deep in his ass. He cleared his eyes and found Penny standing next to the bed, still dressed in her Mrs. Claus outfit.

“I thought you were going to release me.” He said weakly, his throat dry.

Penny smiled at him, and he didn’t like it. “You can see from the clock the night is still young.” She said, pointing to a clock on the television that until now David was unable to see. It surprised David to see that it was still a few minutes before midnight. All that he had endured had only taken a couple of hours.

“I haven’t been totally up front with you Dave. I came to the company for a fresh start. You see, I like you, enjoy a little Christmas fun. But, I ran out of conquests at my last position. A good ass is hard to find. I planned on keeping to the usual setup of getting some horny idiot drunk and then plowing his ass, but then you came along. I did find out about you from some of the other ladies, and then I decided to change the game. Why should I have all the fun?” Penny explained, watching his face as her tale unfolded.

“Wait, wait, what do you mean?” David asked frantically. She had beaten him at his own game, but it was obvious that she had more planned.

“I feel that everyone, every woman and every man should have a juicy holiday fuck. We just need to get the roles right. Now, I will do better next year, but I couldn’t set everything up this year, so you’ll just have to take one for the team.” Penny explained as a knock came to the door.

David struggled as she went to answer the door, and soon heard a chorus of voices. He looked on in dread as Penny returned to the room, followed by six of his previous conquests. The women just smiled at him, and one by one, they removed their coats, revealing an outfit just like Penny’s…candy cane cock included.

It was going to be a long night.

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