A New Playmate for Christmas - Part 5

Click here to read the previous parts of the story.

---

Sadie was naked and in the luxurious hotel bed when Dale emerged from the bathroom. He too was naked, though he felt decidedly less comfortable than she appeared to be.

"Did you do it twice?" she asked.

The 'it' she was referring to was an enema, which he'd done to prepare for the ass fucking he was going to take that night. An ass fucking that would be delivered by her client Ian, a man who'd quickly developed a deep affection for humiliating Dale.

"So you're nice and clean?"

"Yes, clean as a whistle."

She looked skeptical. "Did you check?"

"How would I do that?"

Sadie beckoned him closer to the bed and Dale approached. She signaled for him to spin around and he did so. He looked over his shoulder to see that she was sucking on two of her fingers. Those fingers then ended up in his asshole. She probed him without warning but the lube he'd used for the enemas made her entrance painless.

Sadie rooted around in his ass in the least sexy manner imaginable and pulled her fingers free after a handful of seconds. "Turn around and get on your knees," she said.

Dale turned and fell to his knees. He stared at her fingers, which were no more than a few inches from his face. They looked perfectly clean, which he suspected was the point of her probing.

"It seems like you did a good job," she said. "Your ass is nice and clean. I'll bet my fingers smell fairly fresh, in fact."

Dale had no intention of leaning forward to smell her fingers, but Sadie extended her arm and held them under his nose. He inhaled without thinking and the smell of soap tickled his olfactory senses. He was nice and clean.

"Go put your cock cage and panties on," she ordered.

There was no eroticism to her tone. She was a woman on a job and Dale was part of that job. She was ordering him around like he worked for her, though he wasn't being paid.

Dale did as he was told, though. He put on the cock cage and the panties they'd bought at her friend's sex shop. He thought of how the two women had teamed up to humiliate him in the process of giving him an orgasm. He closed off those thoughts, though, as they led to a bit of growth between his legs, which made fitting into the cage harder.

After taking a bit of time to clear his head Dale managed to fit his flaccid cock into the cage and lock it. He then stepped into the panties and pulled them up his legs before returning to Sadie to model for her.

"Spin around," she said with a smile.

Dale spun like the plaything she'd turned him into and Sadie looked positively delighted when he'd finished showing off his assets.

"On your knees."

He fell to his knees as Sadie got out of the bed and sauntered towards him.

"Kiss my feet," she instructed.

Dale bent over and kissed her beautiful feet. He let his lips linger against her skin and found particular pleasure - for reasons he couldn't discern - in kissing each of her lovely toes.

"Look up at me."

Dale sat back on his knees and looked up at the woman who'd introduced him to a whole new world of sexual pleasure since their chance meeting just a handful of weeks ago.

"Tonight is going to be hard for you, Dale," Sadie explained before taking a step closer and running her fingers through his hair. Dale leaned forward in an attempt to kiss her pussy, but Sadie grabbed a tight fistful of his hair and pulled back. "It's going to be humiliating because that's what Ian wants it to be. You're not going to enjoy getting fucked in the ass. I promise you that. It's going to hurt. He's going to make it hurt. He wants to take away your manhood and he wants to use his cock to do it. He will, to a certain degree, succeed at that. He won't take it away permanently, of course, but he will temporarily steal your sense of manhood from you as he uses your ass for his pleasure."

Dale knew she was right - that he wouldn't enjoy getting fucked - but there was something about being on his knees in front of her as she informed him that made his cock stir in the cage.

"When he's inside you, when he's got his hands on your hips and he's fucking your ass painfully, I want you to think about me and only me. I want you to think about the fact that you're getting fucked for my benefit. Ian is, after all, paying quite a bit of money to live out this fantasy."

"How much?" Dale asked.

Sadie smiled and released his hair. She pushed two fingers into his mouth and penetrated him as deeply as she could.

"Ten thousand dollars."

His eyes went wide.

"He's paying me ten thousand in cash to fuck you, Dale. To humiliate you. To take away your manhood. To shame you. He gets off on it to such a degree that he's willing to shell out a small fortune. Fucking you won't be the only thing he does tonight, but that's the main event, Dale."

Dale knew that Sadie made good money as a companion - as she called it - but he was astounded that she could make that much money from one night.

"And before you ask, I won't be giving you any of that money," she added. "Not a dime. All of it's going into my bank account. Your participation is unpaid and voluntary. You're doing it for me. You're doing it because you want to be a good plaything and because you want to continue to be my plaything after tonight."

Dale nodded.

"Remember that when you experience the agony of getting fucked in the ass by a man," she said while wiping her fingers on his face. "Remember that you want to be a good playing for me. Remember that you volunteered for this. Remember that I'm capable of making you feel good in ways no woman ever has."

"I know you are and I'm so grateful for all the ways you've made me feel good, Sadie."

"Yeah? You like the way I treat you, Dale? You like being a plaything? You like sucking on my toes, eating my ass, drinking my piss, and offering up your body so another man can fuck you for his pleasure?"

He nodded. "Yes, I do."

Sadie probed his mouth once more, this time with three fingers. She probed deep enough to make him gag and Dale experienced the unpleasant sensation of his body rejecting the invading fingers. He struggled to stave off his desire to vomit and felt some of the acid in the back of his throat. It felt like a small price to pay to satisfy Sadie's desire to take ownership of his mouth in that moment.

"Ian will be here soon," she explained. "When he arrives you will take your place on your knees in the corner of the room. You will wait there without saying a word until you're called into action. Once you are, you will do as Ian desires. I expect he'll fuck your mouth before he fucks your ass and I imagine he won't be gentle about it."

"I'll do whatever he wants," Dale said. "I'll do it for you, Sadie."

She smiled sweetly and bent over to kiss him. "I know you will. That's why you're the perfect plaything for me."

Dale's body hummed with joy at her kiss, her comment, and the smile on her face. Making Sadie happy had become the most important thing in his life and he cherished being given the chance to please her.

"Now get in your corner."

Dale turned and crawled to the corner. He situated himself as close to the converging walls as he could and watched as Sadie changed into the elegant - and wildly expensive - lingerie set she'd bought for the occasion. The fit was so perfect it looked as though it had been made specifically for her body, from the way the panties hugged her hips to the way the bra enhanced her already perfect breasts to the way the garters seemed to frame the glorious space between her legs.

Dale remained silent as he watched and Sadie paid him little attention, making him feel like nothing more than an accessory, which was likely how she thought of him in that moment. She was working, after all, and she's brought him along as a component of doing a good job. That's all he was, which is why he'd been instructed to wait silently in the corner. There was something thrilling about being treated as an accessory and it led to a constant, low level of desire humming through Dale's body during the entirety of his time on his knees.

"Ian's on his way up," Sadie said after receiving a text. "You deserve a little something before the fun gets started. A little reward." She approached Dale, pulled down her panties to reveal her pubic hair, and said, "You may sniff my pubes."

He leaned in, pressed his nose against her scratchy pubic hair, and inhaled deeply. He did so over and over and was delighted at the arousal he felt upon breathing in her scent. Perhaps his body was already attuned to her pheromones and programmed for arousal. Perhaps he was simply smelling a bit of the pussy he craved so desperately. Perhaps it was just thrilling that she thought of smelling her pubic hair as a reward for him. Whatever the case, Dale was enthralled.

"Thank you," he said when she stepped away and adjusted her panties.

"You're welcome, plaything. Now remember your place tonight. You are to do as you're told, no matter how humiliating or painful it is. If you should fail to do so, our relationship will come to an end. Do you understand?"

Dale nodded vigorously. "I understand." The last thing he wanted was his relationship with Sadie to end, so he was determined to do whatever was required of him that night.

A knock on the door announced Ian's presence and Sadie smiled and left the hotel suite's bedroom. She greeted her client and Dale listened as they shared a drink, conversed, and fooled around. Nearly an hour passed before they made their way to the bedroom and Dale spent the entirety of that hour on his knees in the corner, just as he'd been instructed.

Ian was absent his clothes as he and Sadie entered. His cock was hard and Dale couldn't help but feel a touch of fear work its way through him as he imagined the impressively large phallus entering his body.

"I think he's staring at your cock," Sadie said. "Though I don't think it's desire he feels, not like when I stare at your cock, baby. I think it's fear he feels."

"He should be afraid. I'm not going to be gentle."

Sadie stroked Ian's cock and kissed his neck. "Good. He doesn't deserve it. In fact, he deserves the opposite. He's a pathetic worm of a man. He deserves to be bent over and fucked hard. He deserves to suffer the pain of being taken anally by a superior man. He deserves to have a sore ass for days after this."

"What about a sore throat?" Ian asked.

Sadie looked at Dale and smiled as she stroked her client's cock. "Are you planning on fucking his face?"

"I am."

"Well, there's no time like the present."

Ian walked to the corner of the room, grasped his cock at the base, and slapped Dale's face with it. The sudden burst of pain was shocking and the humiliation that followed felt like salt in the wound. Ian repeated the procedure a handful of times, leaving Dale in a state of mild agony before the cock pushed past his lips and into his mouth.

Ian was not gentle. Not even close. He used Dale like a toy. Like an object. Like there was no need to be even the slightest bit concerned about his enjoyment.

There was no enjoyment to be had. There was only the effort to survive the onslaught of a thick cock moving in and out of his mouth, of that cock pushing deeper and deeper with each thrust, of his jaw aching, of his gag reflex triggering over and over, of his eyes watering, of saliva dripping down his chin and onto the floor beneath him.

Dale felt like a mess when Ian finally pulled out. A handful of aggressive cock slaps across his face only enhanced that feeling as he was soon covered in the thick mucus the cock had pulled from the back of his throat.

"Pathetic," Ian said. "You pathetic fucking faggot."

Dale didn't want to look up at him, but Ian forced him with a swift yank on his hair. A moment later he spit on Dale and laughed. He dick slapped a few more times and then stepped away.

Dale saw Sadie in the bed. She was still in her flawless lingerie and her legs were spread. Her fingers were in her panties and the look on her face made it seem like she was genuinely turned on by what she'd just watched. Either that or she was doing a great job of faking it.

"Come here, baby," Sadie said to Ian.

He turned and crawled into the bed. She welcomed him between her legs and they kissed with surprising passion and vigor. Sadie reached down to stroke his cock while their tongues danced and she moaned in a manner that once again indicated great arousal.

"It makes me so wet to see you treat him like that," she said. "To see you humiliate him like that. To see you treat him like the pathetic little toy that he is."

"You ain't seen nothing yet," he replied.

Sadie moaned and lured his tongue into her mouth once more. It was either the most convincing performance Dale had ever seen or she was massively aroused at having witnessed his humiliation. He decided it was the latter and he found an even greater sense of motivation to submit to Ian's upcoming anal assault.

"Will you fuck him?" Sadie asked. "Will you fuck his pathetic ass? Will you fuck him like the worthless faggot he is?"

"Fuck yes."

Sadie turned to the nightstand and grabbed a condom. She tore it open and quickly rolled it down Ian's cock. They kissed as she stroked him in the rubber and again she seemed overwhelmingly excited for what was about to unfold.

"Get in the bed. On your hands and knees," Ian instructed.

Dale hopped to his feet and hurried into the bed. He crawled forward until he was on his hands and knees between Sadie's legs and he felt such joy at seeing the bright smile on her face.

"You'll never forget this night," she said. "You'll never be the same after he's done with you."

Dale was about to say something when Ian smacked his ass so hard he nearly fell onto the bed. His legs and arms shook for a moment but he held himself up. More pain followed, but this time it was from the head of Ian's cock pressing against his asshole and moving inside him.

"Does it hurt?" Sadie asked.

"Yes. It hurts so bad."

Ian kept pushing and Dale closed his eyes and tried to breathe deeply and slowly. It felt like his asshole was on fire, though, as it stretched wider than it had even stretched before.

The pain receded a little when the head of Ian's cock moved past his anal ring. The shaft was still thick, though, and there was no give. It was a rigid pole of flesh in his asshole and there was no changing that.

Sadie's fingers slipped into her panties and she masturbated with a look of intense pleasure on her face. More intense than Dale had seen before and again he wondered if she was either the finest actor he'd ever seen or if she was massively aroused at his utter humiliation.

It was not like when Dale had eaten Ian's cum. That had turned out to be strangely arousing. Getting fucked in the ass wasn't that. It was purely unpleasant. It hurt. It felt like he had to go to the bathroom. It was humiliating to be used like a man's fuck toy, to have his sexuality upended as a man fucked him.

"This is what you're good for, Dale," Sadie said as she pulled her fingers from her panties and shoved them in his mouth. "For getting fucked for someone else's pleasure. In this case, you're getting fucked for Ian's pleasure and mine. You're getting fucked for the benefit of my bank account, too, if we're both being honest. The best part is, all you're getting out of it is a fat cock ruining your asshole."

That last part wasn't true for Dale. It wasn’t anywhere near the best part. Dale wasn't enjoying the anal sex. Not even remotely. He was, however, enjoying Sadie's pleasure and she knew that. She probably wasn't going to say it, but he was absolutely getting off on her pleasure. He could feel the sense of satisfaction coming from that even while his asshole felt like it was burning, like it would never recover from the anal pounding he was taking. There was even a sense of pleasure in sacrificing himself so that Sadie's bank account could grow by five figures without much effort on her part.

Sadie's fingers departed his mouth and Ian grabbed a handful of Dale's hair and pulled hard. His neck snapped back and suddenly he was getting fucked even harder. He gritted his teeth and groaned from the pain, which felt like it was on the verge of being too much to handle.

Then Dale heard the sounds of Sadie's wet pussy. Of her masturbating with great vigor. Of her getting off on his misery. It was those sounds that kept him going. He fought through the pain because she was turned on.

"How does it feel to rob someone of their manhood?" Sadie asked.

"It's even better than I thought it would be."

Sadie laughed. "You can fuck him more than once, you know. You can ruin him as many times as you want tonight. You paid for the whole night, after all."

Ian brought his hand down on Dale's ass and he cried out in pain. He did it again, and again, and again. Dale's ass throbbed and his asshole was still on fire. Ian was somehow fucking him harder and faster and the pain had only deepened, as had the humiliation.

Then, finally, it was over. Ian pulled out and tossed Dale aside, moving him from between Sadie's legs. She yanked the condom off and quickly put on another. Before long Ian was inside her. They kissed furiously as he fucked her with incredible speed and power as Dale laid on his stomach and waited for the burning pain in his ass to subside. All the while he watched as Ian enjoyed Sadie's pussy, which Dale knew he'd never get to enjoy. He was her plaything, after all, and her playthings didn't get to fuck her. She had plenty of men for that.

Ian came loudly, as did Sadie. She wrapped her arms and legs around him in a manner that struck Dale as warm and loving and he felt a remarkable sense of jealousy as he witness that simple act.

They kissed slowly in the aftermath of their climaxes and Dale marveled at Sadie's ability to deliver the intense pleasure her client had paid for and for her to enjoy every minute of it.

"Let me feed him your load," she said.

Ian smiled and pulled out. He laid next to Sadie as she removed the condom and turned towards Dale.

"On your back, faggot."

He rolled onto his back and a moment later the condom dangled over his mouth. Sadie upended it, placed the open end on his tongue, and ran her fingers down the rubber, pushing every bit of hot cum into Dale's mouth.

"Hold it until I give you permission to swallow, plaything," she said.

Dale laid there with a load of cum in his mouth - and a condom across his face - as Sadie crawled over to Ian and cuddled up with him. She ran her fingers down his chest and stomach and cupped his balls while her lips danced over his neck and cheeks.

"I haven't cum that hard in a long time," she said. "As it turns out, your fantasy really turned me on."

"Me too. And I will fuck him again tonight. I will ruin him while you watch. I'll take away every shred of manhood he has. I'll break him."

"Good. Toys like him are meant to be broken."

Dale was gripped with a sudden sense of fear. Ian meant what he said and Sadie might have meant what she said. If so, Dale was in for a miserable night. He knew he couldn't be broken, though. He knew that serving Sadie would keep him whole, that he'd find pleasure even in the misery. That put a smile on his face even as the taste of the cum in his mouth threatened to overwhelm his senses.

Dale was a plaything for Sadie, but he liked being a plaything. He liked his place in her life. He liked serving her. He wanted more. Much more. He wanted to keep going down the path she'd set out and discover even more about himself and his submissive desires.

He wouldn't be destroyed. He wouldn't be broken. He'd just become a better plaything, which was all he wanted to be.

The End.