Conquering Christmas

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.