A New Playmate for Christmas - Part 4

Click here to read the previous parts of the story.

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"Are you familiar with the concept of erotic humiliation?"

Dale was naked and on his knees in Sadie's living room. Her big toe was in his mouth and he was sucking on it as she'd instructed him to do so. He was familiar with the concept.

"Silly question, I suppose," she said with a smile. "Of course you're familiar with the concept. I've subjected you to quite a bit of erotic humiliation since we met, haven't I?"

He nodded. Dale hadn't really thought of it in that way, but of course that's what she'd done. He'd swallowed her spit and another man's cum. She'd pissed on him on multiple occasions. He'd been bound and watched as someone else fucked her. He'd been humiliated for her pleasure on numerous occasions.

"You also have a passing familiarity with someone who has desires that might be described as sadistic. I'm not sure I'd go so far as to describe myself as that, but it's true that I find pleasure in making you suffer - in small, humiliating ways - for me."

Dale sucked hard on her toe as he pulled back. The moment her flesh popped free of his mouth, he dropped down, extended his tongue, and licked from her heel all the way to the tip, doing so numerous times as she smiled at him while holding a glass of red wine, which he'd poured for her.

"It is, after all, humiliating to sit naked on my living room floor and lick and suck on my relatively dirty feet, isn't it?"

"Yes."

"And yet your cock is hard," she noted. "Is that because you're a masochist, Dale?"

He shook his head. "I don't think so."

"I don't think so either. I think you're a submissive. I think you get off on serving me, on doing what turns me on. That's why you stripped, poured me a glass of wine, and got on your knees without any hesitation. That's why you licked my sweaty, dirty feet when I told you to. That's why you sucked on my toes. That's why you cleaned Ian's cum off my tits and ass last weekend. That's why you put your tongue up my asshole and tasted my insides when I instructed you to. That's why you let me shove my fingers up your ass when I jerk you off. Because you know all of it turns me on."

"Yes. I do love making you happy, Sadie. I love being able to turn you on in that very specific kind of way."

She smiled down at him, pulled her left foot away, crossed her legs, and offered her right foot. Sadie wiggled her toes and Dale went to work licking the sole. He cleaned the sweat and dirtiness she'd picked up after a day in heels. He sucked on her toes. He found it thrilling to do so, in part because of the smile on her face and in part because the more time they'd spent with each other the more pleasure Dale found in the demeaning acts that Sadie demanded of him.

"If I were to piss in a glass, would you drink it?" she asked.

Dale had tasted her piss before, though only in the smallest quantities as some of it splashed into his mouth while she urinated on him in her shower. The taste was unpleasant, as one would expect, and he wasn't sure he could handle an entire mouthful or even a few sips. Dale suspected that was the point, though. He wasn't meant to enjoy drinking her piss. He was, in fact, meant to hate it and to do it despite the revolting nature of the act.

"Yes, I would," he answered after a few moments of contemplation. A wave of arousal passed through him as the words left his lips.

"It feels good to say yes to me, doesn't it?"

Dale nodded and took her big toe in his mouth. He sucked on it while holding eye contact with Sadie, who looked utterly delighted at his eagerness to be a good playmate for her.

"Ian made a special request," she said with a smile.

Dale knew better than to ask, though he couldn't help his curiosity. He'd watched Ian fuck Sadie, playing the part of her beta cuckold boyfriend because he wanted to make her happy. He'd enjoyed himself a great deal more than expected, though, and he felt more than a little excited at the idea of enjoying that experience once more.

"He wants something a little different than last time," she continued. "Something that will be more difficult for you. I think he wants to make you push your boundaries a great deal further than simply watching. To be honest, I think he was a little disappointed that you seemed to enjoy yourself. That's partly my fault, I suppose, as I underestimated just how much of a submissive you are."

"What does he want me to do?" Dale asked.

Sadie rubbed her foot over his face and shoved her toes in his mouth, stretching his lips wide. "I want it to be a surprise, so I'm not going to tell you. Not yet, at least. I want you to agree to do it without knowing what it is."

She pulled her toes from his mouth and rubbed the saliva across his forehead.

"I'll do it," Dale said. "Whatever it is, I'll do it. I'll do it for you, Sadie."

She smiled, inched her hips forward, and leaned closer until her lips hovered achingly close to his. "I thought you'd say that. You might live to regret having said that, but I can't tell you how wet I am right now, Dale. I think you deserve to worship my cunt. Would you like that?"

He nodded. "More than anything."

"Good. All you have to do is finish my wine and I'll let you take my panties off, crawl between my legs, and tend to my slippery cunt with that eager tongue of yours."

Dale reached for the glass of wine but Sadie pulled it away and stood up. She lifted her tight skirt up around her waist, pulled her panties aside, squatted just a little, and held the wine glass under her pussy.

"You didn't think you'd get to enjoy a glass of wine, did you?"

Dale shook his head as Sadie filled the half empty glass with her piss. She cut off the flow right before the liquid threatened to spill over the top of the glass and handed it to Dale.

"Drink up and you can worship my pussy. I'll even let you give me multiple orgasms. Then we're going shopping."

Dale brought the glass to his lips. He made the mistake of inhaling through his nose, though, and the pungent scent of piss nearly made him gag. He pulled his head away and came remarkably close to spilling the wine and urine concoction as Sadie laughed.

Dale tried again, this time without breathing. He took a massive swig of the liquid - which was unpleasantly warm on his tongue - and swallowed. It was awful, of course. Truly, nauseatingly awful.

"Fuck," Sadie said softly as she sat, reached between her legs, and played with her pussy. "You have no idea - truly no idea - how hot it is to watch you drink my piss, Dale. To watch you consume my waste, to know that you're tasting it, that you're taking it into your body, that my piss is going to rest in your stomach. Fuck...you better hurry up and drink it all or I'm going to give myself my first orgasm."

Dale hurried. It was exceptionally difficult, but he drank all of the piss and wine and set the glass on the coffee table. Sadie then grabbed a handful of his hair and roughly pulled his face between her legs.

She came quickly. No more than a handful of seconds. She pushed Dale away as she climaxed and he kissed her inner thighs while running his fingers over her legs.

"Get on your back," she said. "I'm going to sit on your face for a while. You can start by eating my ass and then I'll let you tend to my pussy for another orgasm. I'm going to soak your face in my cunt juices and you're going to wear them while we go shopping."

Dale's body hummed with erotic energy as he got on his back. Sadie stood, straddled his face, and slowly squatted until her asshole hovered right over his mouth. Then she sat down, smothering him with her beautiful ass cheeks. He put his tongue to work immediately and sank into a place of submissive bliss as she moaned softly and fed him her beautiful ass.

Dale wasn't sure where they were going shopping, but in the moment he loved the idea of doing so while covered in a thin layer of her dried pussy juices. He even loved the idea of people knowing that she'd just ridden his face and coated him in her liquids. It would be humiliating, yes, but Sadie had made it perfectly clear that she got off on his willingness to suffer humiliation for her, and thus Dale was more eager than ever to surrender his dignity for her delight.

---

Had the store not been filled with lingerie, kink outfits, sex toys, and other items designed for the pursuit of pleasure, Dale would not have guessed it was a sex shop. From the outside, the building looked more like a cottage that he would have guessed housed a small bed and breakfast. The inside was just as lovely - with cozy design touches all over - and yet the walls were lined with all manner of kinky delights.

"Do you shop here often?" he asked as Sadie ran her fingers over a red latex catsuit.

"I do. This place is an invaluable resource for anyone that caters to carnal desires. I abhor ordering online. So often you end up with something cheap and ill-fitting. Here I can try on the outfits. I can get my hands on the toys my clients want to play with." She turned to Dale and smiled. "I can make sure that everything we need for your upcoming humiliation will fit exactly as it needs to fit."

Dale was equal parts nervous and excited, and if it weren't for Sadie's obvious delight the nerves likely would have won out.

"Sadie, darling, welcome back."

Sadie stepped into the embrace of a slim, elegant brunette woman in a pair of jeans and a white satin blouse. She looked to be in her late 40s and there was nothing about her that indicated that she was the sort of woman that would work in a sex shop, though Dale imagined that was precisely why the shop was so vastly different from what he'd expected.

"Maria, it's so good to see you," Sadie said before the women exchanged quick kisses on the cheek.

"And who is this?" Maria asked as she turned her attention to Dale.

"This is Dale, my new playmate."

Maria's face lit up. She clearly knew of the sorts of fun that Sadie had with her playmates. "It's a pleasure to meet you, Dale. I'm so happy that our Sadie has found someone new to have fun with. Is it safe to assume that you had a little fun with her before coming here?"

Dale had forgotten of the dried pussy juices on his face and he felt a little shy as Maria smiled at him. "Yes, it's safe to assume that."

"And are we here shopping for some fun you intend on having with your playmate, Sadie, or are we looking for something else?"

Sadie stepped closer to Dale, took his hand in hers, and kissed him on the cheek. "Dale's going to help me with a client and we need a few things to enhance the experience."

"How delightful," Maria replied. "What is it you're looking for?"

"Let's start with a chastity device. As small as possible."

Dale tensed up. He'd never seen or worn a chastity device, but he knew what Sadie was talking about.

"Very good," Maria said. "Follow me."

They followed the elegant brunette through her store and stopped in front of a wall of devices, all of which were designed to imprison a man's cock. Dale was genuinely speechless as he studied the stunning variety of options.

"Could he handle a flat device?" she asked.

"No. Not yet, at least. He has a lovely cock, actually, so we'll need something a bit bigger. I want it to be a touch uncomfortable when he wears it, though, as it's not intended for long term use. It's more of a one night thing."

Maria pointed to a small plastic device. "These are good for short term use. Plus, they come in a variety of colors."

"Do you have pink?"

"I do," Maria said with a smile. "In back. I do like a feminine color on a submissive's cock. It's just a bit more humiliating, isn't it?"

"It is," Sadie agreed.

Dale stared at the small plastic chastity device and imagined his cock being imprisoned in it. He wasn't sure how it would fit, as he wasn't all that small even when flaccid. Sadie seemed confident, though, and he'd agreed to do whatever it was she had in mind for him, so he remained silent.

"Is there anything else you need before I go in back to find your playmate's chastity device?"

Sadie smiled. "Yes. We need a pair of panties. Specifically, though, we need a pair that allows for access to his ass."

Dale desperately wanted to ask why he needed a combination of a chastity device and a pair of panties that allowed for access to his ass. He remained silent, though.

"You're really going to have some fun with him, aren't you?"

"Dale's helping me make a client's fantasy come true. He's a better playmate than most."

Maria led them to the lingerie section of the store, which was impressively large and featured a breathtaking variety of styles. They made their way to the panty section and she pointed out a small selection of options that offered access to the ass.

"You could go with pink to match the chastity device," Maria suggested. "Or a complimentary color like this delicate light yellow or perhaps a baby blue. I'd recommend lace, of course, as there's nothing quite as delightfully feminine as a pair of lace panties."

Sadie picked up a pair of pink lace boyshort panties - with an opening on the backside, of course - and held them up to Dale's crotch. He looked down and imagined wearing them along with a small chastity device. The mere thought of it was humiliating, aided by the fact that he'd already agreed to do whatever Sadie wanted.

"These are perfect," she said.

"Should we have him try everything on?" Maria asked.

"Of course."

"I'll go get the chastity device."

Maria walked away as Sadie placed the pink panties in Dale's hand. The fabric felt impossibly soft and a small part of him actually looked forward to wearing them, if for no other reason than they were likely to be quite comfortable.

"I'm surprised you haven't asked what Ian wants from you," Sadie said as she moved behind Dale. Her lips found the back of his neck and she kissed him softly, sending shivers of pleasure down his spine.

"I want to know," he replied. "But I already agreed to it and I guess I figured that you'd tell me when I needed to know."

Sadie put her arms around him. One hand moved up his chest and the other between his legs. He stroked his cock and whispered, "To be honest, I was waiting to see how long you could hold out before asking. I'm sure you have some idea of what's going to happen, though."

"I think I do."

"Your ass is involved," she said. "Your ass is going to get fucked, in fact. Fucked hard, I would imagine."

Dale was nervous, but Sadie's caresses had left his cock hard and his body flooded with desire.

"It won't be my fingers in your ass, though," she added.

Sadie turned Dale's head and kissed him. Her tongue gently danced with his as his cock reached a state of full rigidity.

"Ian's going to fuck you, Dale," she whispered. "He's going to humiliate you. He's going to take away your manhood by fucking you while you're dressed in panties and your cock is locked in a little cage. He's going to show you that you're not a man, at least not compared to him. He's going to fuck you after having fucked me to a thunderous orgasm while you watch like a little bitch. You're going to fluff him before he fucks me, too."

Dale felt genuine fear. He hadn't even imagined the possibility of Ian fucking him. He should have, perhaps, but it hadn't entered his mind and yet he'd agreed to it. He'd agreed to let a man fuck him. He hadn't know that's what he was agreeing to, of course, and he was sure he could back out, but he wanted so desperately to make Sadie happy that Dale knew there was no chance he'd surrender to his fear.

"Having a little fun, are we?" Maria asked.

Dale turned to see her holding the pieces of a small pink chastity device in her hand.

"Let's get you to the fitting room."

Sadie took his hand and they followed Maria through the store and behind a soft pink curtain. She gestured for him to step into one of the four fitting rooms and handed him the chastity device as he did so. Sadie gave him the panties and Dale moved to shut the door.

"There's no need for that," Sadie said. "You can change in front of us, Dale. You're going to model your cute little outfit for us, after all."

Dale stripped in front of Sadie and Maria. His cock was still hard, though, so it was impossible to even attempt putting on the chastity device.

"Perhaps I shouldn't have gotten him turned on," Sadie said with a smile. "I couldn't help myself, though. I wanted Dale to know the details of his work for my client. I wanted him to know that he's going to get fucked by a man for the first time in his life, that he's going to be humiliated in those panties and that chastity device, that he's going to suffer that humiliation - and let's be honest, the pain of anal sex - for another man's pleasure."

"And for your pleasure, of course," Maria added.

"But of course."

They both looked at Dale's erect cock and he felt both self-conscious and a little bit delighted at being naked in front of two beautiful women.

"We could milk him," Maria suggested. "His cock will be a great deal more compliant if he cums."

"What a delightful idea," Sadie replied.

Both women stared at him for a few moments longer before Maria said. "I'll be right back."

She walked away and Sadie stepped into the fitting room. She caressed Dale's stiff cock and kissed him with such passion that it caught him off guard.

"It's not just Ian you're going to make happy," she said softly. "I'm going to be quite happy too. Plus, you'll be eating my pussy as he takes your dignity by fucking you."

Dale wasn't sure why, but something in her wording thrilled him.

"With any luck, you'll get to make me cum multiple times with your tongue as Ian has his way with your tight, virginal asshole."

They kissed again and Dale closed his eyes and sank into it. He enjoyed the warmth of her lips against his and the way her tongue moved expertly in his mouth to maximize his arousal.

Dale would have happily made out with Sadie for the rest of the day, but she pulled away as Maria returned holding a dildo.

"He's going to be sucking cock, right?" she asked.

Sadie nodded.

Maria held up the toy and revealed the suction cup at the base. "Stick your tongue out, Dale."

He did as ordered and Maria rubbed the bottom of the suction cup over his tongue and used the moisture to deftly affix the toy to the wall in front of him. He stared at the lifelike cock that was now just a few inches from his mouth.

"Maria, I love the way you think," Sadie said. "Dale, take the cock in your mouth. Suck it like a good little slut while Maria and I milk you."

Dale offered no resistance to her command. He wrapped his lips around the lifelike dildo - remarkably lifelike, in fact - and sucked cock.

"Mmm, that's a good little cocksucker," Sadie whispered as her lips brushed against his neck. "I can't wait to see you sucking Ian's dick. I can't wait to watch him grab your head and shove his dick down your throat until you gag."

As she said it, Sadie pushed on the back of Dale's head, pushing the rubber cock into his throat. He gagged hard and his stomach nearly emptied itself before he fought off the reflex. Sadie smacked his ass while he pulled back, took a deep breath, and resumed sucking cock.

"Would you like to stroke him, Maria?" Sadie asked.

"It would be my pleasure."

The older woman stepped closer and Dale felt the softness of her satin blouse against his skin as her fingers encircled his cock.

"Are you looking forward to getting fucked, Dale?" she asked while stroking him slowly.

He shook his head with the dildo in his mouth.

"No, I suppose you wouldn't be. Most men - straight men, at least - have little interest in being fucked by another man. That's the thrill of it for Sadie's client though, isn't it? He gets to take your manhood from you with his cock. He gets to pound your asshole while you moan from the pain. He gets to make you take his dick. He gets to make you give him pleasure while you're caged and pantied like a good little faggot."

Sadie spit and a moment later Dale felt her hand move between his ass cheeks. She spread her saliva over his hole and a moment later her fingers entered him. He groaned around the dildo. He was being stroked and anally fingered while sucking cock. His mind was awash in thoughts of Ian violating his asshole in an attempt to humiliate him.

"Ian's going to make you a faggot, Dale," Sadie said before kissing the back of his neck. "He's going to make you a faggot while I watch. He's going to do it because it gets him off to do so. He's going to do it because he knows I like you, Dale. He knows I care for you. He's going to do it because he wants to humiliate you in front of me."

Dale moaned around the dildo and took it as deep as he could. His balls tightened and his loins tingled. He was moments away from cumming.

He climaxed with the dildo in his mouth and Sadie's fingers fucking his ass. He climaxed while thinking about another man fucking him. He climaxed and spurted his cum all over the wall of the fitting room. Maria milked his cock expertly, working the head with her fingers and ensuring a long, thoroughly pleasurable orgasm that had his legs trembling.

"Clean up your mess," she said after releasing his cock. "Lick up your load before it reaches the floor, Dale."

Sadie pulled her fingers from his ass and Dale dropped to his knees. He leaned forward and licked the streaks of his cum from the wall. He licked over and over, cleaning up his salty, awful-tasting load and swallowing it while the women watched.

"We're going to get cleaned up, Dale," Sadie informed him. "We'll be right back and then we'll get you in that chastity cage and panties to make sure everything fits."

They walked away as Dale continued to lick up his cum. His body had been emptied of every bit of arousal, and yet he still felt a desire to do as Sadie said, to obey her, to submit to her.

He felt no desire to get fucked by Ian, though Dale knew that he'd likely be turned on by the time that event unfolded and it wouldn't be nearly as awful as he was imagining in that moment.

Getting fucked wouldn't be good, though. It wouldn't be close to good. Dale was willing to suffer through unpleasantness for Sadie, though. He was willing to do damn near anything for her, in fact, so getting fucked by a man seemed like a fairly simple task if it would give her pleasure.