Masters of the Hotel Bentmoore: Chapter 1

“Michelle, I am Mr. Dean. I will be your host for your stay at the Hotel Bentmoore.”

“It’s nice to finally meet you, Mr. Dean.” Michelle Langley’s hand came up to shake Mr. Dean’s. Mr. Dean accepted the gesture of cordial introduction, but frowned. He was not used to women shaking his hand at the Hotel Bentmoore, at least not within the confines of the lower floor. Above, where guests mingled side by side, hotel staff brushed shoulders with wealthy patrons, and everything looked as proper and as elegant as a hotel should, women would sometimes nod his way, smile as they caught a glimpse of him walking past…if they didn’t know who he was, they would sometimes assume he was just another guest, and shake his hand to introduce themselves to a handsome, self-assured man.

But within the walls of the lower floor, it was a different story. Women stripped before him, knelt before him, spread themselves open when ordered…they regarded him with reverence, obedience, and most of the time, complete submission.

They did not shake his hand.

But Michelle was smiling at him as she took his hand, genuine, hopeful, innocent and—Mr. Dean thought—rather naive, given the place she was in. There was a tiny kernel of nervousness in her eyes, but that was to be expected. It was usually the anticipation and the fear of the unknown that made the women nervous, at least at first.

Eventually, with some strict training and consistent discipline, they all came to know what they could expect from his hand. But the nervousness never completely went away—it just turned into a better respect and understanding of him, the man, Mr. Dean. Their host.

In fact, Mr. Dean was expecting more fear behind the eyes, not this tiny shred of trepidation. Perhaps he was too used to his reputation preceding him, he thought.

Michelle gave his hand two small shakes, and when she was done, her smile grew wider. Her hand was small and warm inside his own, but slightly damp. She was more nervous than she looked, Mr. Dean realized. She was sweating. She hid it well.

“I understand you are a friend of Monique’s,” he said, trying to get the conversation going. Michelle’s eyes lit up.

“Oh yes, she and I are good friends. She’s told me how, um, how satisfied she’s been with the service at this hotel. I decided I would just have to visit and see for myself.” She ended the sentence with a small nervous giggle.

Mr. Dean grunted in response. Getting new guests through referrals was nothing new; many of their long-time clients had come to them through referrals. But it was important to discover exactly how much information had been shared, so that no secrets of their clients were revealed. And it was also important to go over exactly what it was the new guest was looking for during his or her own visit, to ensure complete satisfaction.

Monique Hooper was a regular guest of Mr. Dean; she had been visiting him exclusively for almost two years now. But she also came with an established list of expectations, and those expectations varied little from visit to visit. Mr. Dean had no idea if Michelle shared the same predilections of her friend. In fact, he’d been given very little information about Michelle at all, a fact he found most irritating. He had only heard about this new guest the day before, and from Mr. Bentmoore himself.

“I’ve got a new guest for you, Dean,” Mr. Bentmoore had told him, swiveling around to face him behind the ornate desk. All the hosts had their own offices, but they were small and scantily furnished. Mr. Bentmoore’s office was grand and elegant, with a large claw-foot desk taking up the center of the room.

“Young woman by the name of Michelle Langley,” Mr. Bentmoore had continued. He sat in his large leather chair, looking calm and matter-of-fact, but his eyes were buried in a pile of paperwork. “Twenty-three, straight, no husband, owns her own business. She heard about us from her friend, Ms. Hooper. Ms. Hooper’s been an exclusive guest of yours for a while now, I believe?”

“Yes,” Mr. Dean had answered absently, furrowing his brows. “She and I get along well together…but Monique told this woman about us?” His tone was one of surprise. He had always thought Monique kept her regular visits to the Hotel Bentmoore a secret. “Do we know what, exactly, she said to her friend about us?”

“No, and I couldn’t ask, of course. That would be prying. But whatever it was, it was enough that her friend has booked a stay with us this weekend, and has asked for you, personally, to be her host during her initial visit. I told Michelle with absolute confidence you will take care of all her desires, and make sure her stay with us is a happy one, from start to finish.”

Mr. Dean said nothing to this. He tilted his head, looking somewhat concerned.

“This woman, Michelle—did she give you any idea what she wants from the visit? What she specifically has in mind?”

“No, actually, she didn’t. Of course, she expects the full treatment, everything our reputation assures—complete fulfillment. But Michelle was somewhat vague on the specifics of what she’s looking for.”

Mr. Dean frowned. “So what you’re telling me is we know nothing?”

Mr. Bentmoore sighed. “Frankly, Dean, I got the impression this woman isn’t sure what she wants. She doesn’t sound all that experienced with sex, or men in general, to tell you the truth. I think she’s looking for someone to ‘show her the way,’ as it were.” Mr. Bentmoore began to straighten out his pile of papers, avoiding Mr. Dean’s incredulous stare, a fact Mr. Dean noted with alarm.

“But then…why is she being given to me? Why not Shern, or Cox? Or even Sinclaire? All of them know how to handle a woman like that better than I do.”

“True,” Mr. Bentmoore said, smiling down at his papers. “The others have much more experience dealing with the, ahem, inexperienced women. But Ms. Langley heard about you specifically from Ms. Hooper, and insists you be the one to…initiate her. Obviously, Ms. Hooper told her something that caught Michelle’s interest.” Mr. Bentmoore leaned back in his chair, looking up at the ceiling…still not looking Mr. Dean in the eye. “I told her that all our hosts are very adept and knowledgeable, fully able to satisfy her needs. You will, I am sure, figure out how to do that.”

Mr. Dean’s eyebrows went up. There was something going on here, he knew, but he couldn’t quite figure out what. One thing was for sure, he didn’t like feeling cornered.

“Mr. Bentmoore, I don’t know if I am the right host for this guest. Perhaps she should be given to someone else this first time, and once she figures out what she needs, if I am still the right person to give it—”

Now Mr. Bentmoore looked at Mr. Dean sternly, his expression implacable. “She has asked for you, and so she will get you. I know this might be difficult for you at first, Dean, going in blind, but you’ll just have to figure her out. Talk to her first. Get her to open up a little. I’m sure it will be fine.”

They stared at each other for a moment, Mr. Bentmoore looking at Mr. Dean expectantly, and Mr. Dean contemplating his options. At last, Mr. Dean gave a little shrug.

“Yes, Sir,” he replied. “I’ll do my best.”

“Of course you will,” Mr. Bentmoore agreed, in a tone that said he considered the matter closed. “I’m sure you’ll enjoy our new guest immensely.”

But now, standing in front of the new guest, Mr. Dean wondered again if, perhaps, the woman would have been better served with a different host. She certainly did not seem to be the kind of guest Mr. Dean usually attended to.

Michelle was a small woman, short and petite: she barely came up to Mr. Dean’s shoulder. Her skin was a dark crème, even and flawless. It looked very soft, and, to Mr. Dean’s practiced eye, very fragile. She wore a royal blue cashmere sweater over her lithe torso; it clung to her thin arms and softly rounded shoulders, before narrowing in at her flat, tiny waist.

Michelle had surprising ample breasts. They stretched across the material of her sweater, looking proud and evenly rounded. Mr. Dean wondered if she was wearing a padded bra. Probably; there was no way a woman that small could have such generous breasts.

The sweater curved around the top of her narrow hips, the ribbing clinging to the material of her pants. Her pants were black, the kind Mr. Dean thought of as women’s career-slacks, straight-legged and creased. While he knew they were very popular among the high-executive businesswomen, Mr. Dean hated them. They made women look like they were trying to dress like men, when they should be showing off their curves and highlighting their femininity.

Michelle’s hair, a rich luxurious brown, was done up in a soft twist, but a few wisps fell lightly across her delicate nape. Wide, almond-shaped eyes looked at him openly. Her soft lips, shiny with a thin layer of gloss, curved up a little, smiling again in nervous hope. Mr. Dean exhaled slowly. He felt like he was on unexplored territory, and would have to tread carefully. He didn’t much like it.

All the hosts (and hostesses) of the Hotel Bentmoore had reputations for what they were good at, what they could handle best, and what they preferred. One of the things Mr. Dean was known for was being the “ass man.” He trained women in all things anal, and had a vast collection of anal dildos, butt plugs, vibrators and toys kept inside the wardrobes of the activity rooms he frequented. But he was also known for being the serious host, the no-nonsense disciplinarian. He was not a Master Sadist, like Mr. Sinclaire, but he was a Dominant, and did very well with women who felt the need to submit to a strong, controlling, and unbending male figure. He was meticulous, persistent, and very, very strict.

This woman did not look like she wanted to experience the feel of a strict hand on her derriere. She did not look like she even knew what she wanted. In fact, she looked almost confused about what she was doing there at all. But she had come on the recommendation of Monique Hooper, a fact Mr. Dean kept in the forefront of his mind.

Monique Hooper was definitely not the shy or confused type. She had been clear with Mr. Dean from the very beginning about the kind of discipline she craved, and Mr. Dean had always been quite happy and adept at delivering it to her. Could it be that her friend, Michelle, was looking for the same treatment, and simply did not know how to say so?

“Let’s sit down and talk, Michelle,” he said. “I’d like to get a better idea what it is you want from your visit to the Hotel Bentmoore, what it is you’re looking for. I need to know how I can best please you.” The woman dutifully obeyed, planting herself in the chair; but Mr. Dean took note how she anxiously smoothed down her pants, and kept her eyes lowered to her lap. Perhaps she was more submissive than she looked?

“You are very nervous. Why?”

“I’ve never done anything like this before,” she said, her voice high.

“You’ve never come to place like the Hotel Bentmoore before? Most of our new guests have not.”

“No, I mean, I’ve never done this before,” she said, grazing his eyes quickly with her own before darting hers away. “I’ve never discussed with a man what I want, before we… you know… spent some time together… intimately.”

Mr. Dean sighed. That statement alone had just told him much about the woman: she had a hard time even talking about sex. She was obviously not very comfortable with her own sexuality. Maybe she was not a submissive, maybe she was just woefully ignorant, Mr. Dean thought.

“So let’s talk about what you have done before,” he said, trying to put her on comfortable ground. “I take it you are not a virgin?”

“Oh, no, I’m not that,” she laughed again, a nervous titter. “I’ve had sex.”

“Many partners?”

She twisted her hands in her lap. “I don’t know what you call many,” she said. “I mean, in your line of work….”

“I understand,” Mr. Dean said quickly, trying to stop her floundering. “So tell me, are there certain positions you prefer? Certain styles?”

Michelle looked down at the floor. “Oh, I like many positions,” she said vaguely, her face turning red. Mr. Dean knew immediately she was lying. She was being vague on purpose, but there was a secret looming behind her eyes, something specific she wanted, something she would not share with him. Why would she lie, especially about something like this? Why would she not just tell him? Did she expect him to read her mind? Thoroughly vexed now, he scowled. Michelle failed to notice his rising anger.

“Okay,” he said, trying to keep his voice even. He would try to use a more direct approach, keep the questions specific. “Is there anything in particular you had in mind to try this weekend with me? A position, or a toy you need a partner to use on you? A fantasy perhaps, or a scene you would like to play out—”

“No, nothing like that,” Michelle interrupted. “I just…I just…want to have a good time.”

Mr. Dean could feel his frustration grow. The woman was giving him nothing to go on, nothing to start with—and she was lying to him. There was obviously something she wanted: it was why she had come to the Hotel Bentmoore in the first place.

She had her own secret agenda for her visit, it seemed. But guests were not afforded the luxury of secrets at the Hotel Bentmoore, a fact she had yet to learn.

He decided to take a risk.

“May I ask, Michelle, what it was Monique told you that made you decide to visit the Hotel Bentmoore in the first place, and request me personally as your host?”

“Monique told me that you are, um, very strong-willed, and don’t have a problem with, um, how did she put it? ‘Pushing boundaries’ a little.”

That was certainly true. Mr. Dean enjoyed testing Monique’s boundaries, as he did with most of his guests. Sometimes it went well; sometimes it did not, and Mr. Dean would have to pull back. For instance, he had only tried to insert his finger into Monique’s ass once, and her protests had been loud and immediate. Mr. Dean had never tried again. Knowing when to press an issue, and when to stop, was a skill every host at the Hotel Bentmoore had to learn.

“And is this what you are looking for at the Hotel Bentmoore? Someone strong-willed to ‘push your boundaries’ a little?”

“No, not exactly, I, um….” Her voice trailed away, and Mr. Dean’s expression grew stern.

“You what, Michelle? What is it you want?”

“I….” She would not look at him.

“Michelle, look at me.” Slowly, she looked up at him. “I cannot help you if you don’t give me some idea what you want. So what do you want, Michelle?”

Michelle stared at him, her eyes flooded with hidden knowledge, but said nothing. Mr. Dean tamped down the growl in his throat, then gave it a moment of thought. Maybe this was exactly the boundary she refused to talk about? Maybe she just needed someone to overcome her shyness, get over her reluctance, and take the upper hand? Maybe she wanted to be dominated after all, and was waiting for him to make the first move?

He took her by the arm and pulled her up roughly from the chair. Michelle gasped.

“Tell me what you want, Michelle,” he said, peering into her face. Mr. Dean’s voice was coarse and stern. Michelle looked away; Mr. Dean pulled her gaze back with a steady hand on her chin.

“Look at me. Tell me what you want.”

“Don’t do that, I—”

Mr. Dean began to back her up against the wall, locking her arm behind her back.

Michelle’s face paled. “What are you doing?”

“Tell me what you want.”

“Let go of me, I told you—”

“You heard I am strong-willed, and you asked for me anyway. Is this what you’re looking for?” He turned her around in his arms and slapped her ass, hard. Even through the slacks she was wearing, his hand stung from the impact.

“No, wait! That’s not—”

“Then tell me.” Mr. Dean’s control snapped. He twisted her back to face him with a jerk of his arm, and cupped her breast through her bra, taking ownership of her body. His other hand pressed brazenly into her ass. “Tell me what you want, Michelle.”

Michelle’s eyes grew wide with fear. Then, she raised her hand, and slapped Mr. Dean across the face.

Mr. Dean stepped back, putting a hand to his cheek, staring at her in surprise.

“I think there’s been a mistake,” Michelle said tearfully. “I’ve changed my mind—I don’t want to do this anymore. I would like to go.”

Taken aback, Mr. Dean reached a hand out to her. “Wait, Michelle. I must have misunderstood—”

“Yes. Yes, you did. I would like to leave now.” She began to pull desperately on the door. It was, of course, locked. Mr. Dean quickly pressed the button to summon the liaison, but continued to try to placate her. He had made a mess of things, and needed to fix it fast.

“Michelle, I didn’t mean to scare you, I just assumed—”

“I want to go,” Michelle choked out. The door opened, and she stumbled out, bumping into the surprised liaison before pushing past him. The liaison retreated against the wall to give her space to pass, then looked at Mr. Dean in surprised shock.

Mr. Dean watched Michelle sprint down the hallway, calling out in desperation.

“Michelle, please, come back inside—”

“No.” She only took a second to stop and answer him, then made a mad dash toward the elevator. For a moment, the liaison looked at Mr. Dean, baffled and at a loss what to do; then he, too, ran down the hallway to catch up with their frantic guest.

Mr. Dean leaned his forehead against the door frame and closed his eyes. He had just made a horrible mistake.

~ * * * ~

“What do you mean, you ASSUMED?” Mr. Bentmoore roared from behind his desk. “We are not in the business of assuming, Dean. You should have made things quite clear between the two of you before you even laid a hand on her! For you to coral the woman like that, twist her arm, spank her—she told me exactly what you did, you scared the woman badly—”

“I know, I know, I’m sorry.” Mr. Dean put a hand up in a gesture of surrender to stop the tirade, feeling shamed enough. “I thought it was what she wanted. She wasn’t giving me anything else to go on—”

“In what, the first ten minutes of your meeting? You should have spent more time talking to her! Figured out what she wanted, what would please her! You don’t pin her against the wall and start spanking her ass after a brief conversation that isn’t going to your liking!” Mr. Bentmoore’s face was flushed with anger. He glared at Mr. Dean from across the desk. “Really, Dean, I am shocked at how badly you handled things with this woman. It’s not like you at all.”

“I know, I’m sorry,” Mr. Dean repeated, rubbing his hand across his forehead and sighing loudly. “I don’t know what came over me. There is just something about this woman—she didn’t just hold back—she lied to me.”

“Lied to you? About what?”

“There is definitely something she wants, something she’s had a taste of before and has a mind to explore further. I don’t know if it’s a certain position, or a fantasy scene, or what. She won’t tell me, and I have no idea why not.” He crossed his arms in front of his chest, looking solemn. “It’s there, in her eyes, but she won’t tell me what it is….I guess I need more time to get it out of her.”

“Well, time is precisely the one thing you don’t have. She’s packing up—she’s planning on checking out. She could be on her way to leave the hotel right now.”

“Oh, no.”

“Oh, yes.” Mr. Bentmoore pointed a finger at Mr. Dean. “You are going to make sure she does not. I don’t care if you have to get on your hands and knees and give her cunnilingus at the front desk until she agrees, you are not going to let that woman leave this hotel without a smile on her face. We survive on our reputation, Dean. I will not have your stupid mistake blemish it.”

“How am I supposed to talk to her? I doubt she will agree to be taken back to the meeting room, even with the liaison as an escort, to meet me again.” He remembered her frantic dash down the hallway, and frowned.

Mr. Bentmoore looked grave. “That is why I am giving you permission to go up to her room to talk to her.” Mr. Dean leaned back in surprise. It was strict hotel policy that no host was allowed to visit guests in their private rooms on the upper floors. The fact that Mr. Bentmoore would order Mr. Dean to do so showed him exactly how serious Mr. Bentmoore took the matter.

“Do not leave her room until she agrees to stay,” Mr. Bentmoore continued. “Tell her whatever she needs to hear, do whatever you need to do—but get it done.” When Mr. Dean didn’t move, Mr. Bentmoore motioned him toward the door. “What are you waiting for? Go! Before she’s done packing!”

Doing a very good imitation of Michelle from the night before, Mr. Dean got up and sprinted from the room.

~ * * * ~

When Michelle heard the knock on her door, she assumed it was the bellhop coming to take her suitcases. She gasped in surprise when she found Mr. Dean standing there instead. Her first instinct was to shut the door in his face.

“Michelle, I need to talk to you,” Mr. Dean said quickly, sensing her initial reaction. Michelle still swung the door closed, but not enough to shut it, only enough to leave a narrow crack open. She peered at Mr. Dean from around the door, using it as a shield between her and the man on the other side.

She looked wary. Mr. Dean felt even more embarrassed. Mr. Bentmoore had told him the truth: he had really scared the woman badly.

“Why do you want to talk to me?” She asked, facing him through the tiny crack. “I’m checking out today, as soon as possible. As a matter of fact, someone should have arrived by now to take my luggage.”

“Please don’t leave, Michelle, not until I’ve had a chance to make things right. Look, can I just come in and talk to you? I don’t want anyone to see me—I’m not supposed to visit a guest’s room.” He twisted his head from side to side, as if checking for witnesses in the hallway.

Michelle narrowed her eyes, looking suspicious. “If you’re not supposed to be here, then why are you here?”

“Because I feel bad about what happened. I want to make it up to you.”

Michelle’s brows furrowed as she thought for a minute. Then she sighed and opened the door. The man would hardly accost her in her private hotel room, where other guests were sure to hear her scream. And he really did seem sincere. And handsome. And appealing. And there was what Monique had told her….

“Very well, come inside,” she said. “But only to talk. Don’t—don’t touch me.”

“I won’t, I promise,” Mr. Dean said, relieved she had at least agreed to let him in. She motioned him to the chair next to the bed. She remained standing.

“What is it you want?” She asked. Mr. Dean smiled in chagrin. Here she was, asking him the exact same question that was circling inside his own head about her. Fortunately, he, at least, could come clean with an answer.

“I want to make you happy,” he said. “I treated you very badly before, and I want to make it up to you.” When she sighed and shook her head, he put his hand up to stop her from refusing outright. “Hear me out. Believe it or not, I am quite good at what I do. Monique must have convinced you of that, or you never would have asked for me. I just… started off on the wrong foot with you. I’m sorry. It was my fault—I should have been more careful.” Her large almond eyes widened at his generous apology. Her breath quickened a bit, but she said nothing.

Mr. Dean decided to turn on the charm, just a little, just enough to sway her. But he would have to move carefully so as not to scare her. Slowly, he rose from the chair and stood before her, keeping his hands safely inside his pockets. He peered down into her face.

“Please, Michelle, let me make it up to you,” he said again, lowering his voice into a husky appeal. “I promise I can make you one hundred percent satisfied, if you just give me the chance.” He looked into her eyes, and when she looked down to the floor, nervous, he bent down and caught her stare again, an imploring look on his face. She smiled, then turned away, flustered.

As she turned a step away from him, trying to collect herself, Mr. Dean caught a glimpse of her bathroom. The door was open, the light on, and he couldn’t help but get a clear view of the counter by the sink. He raised his eyebrows in surprise. A well-sized, tubular yellow vibrator sat next to the sink, drying after having been clearly used and washed.

Now Mr. Dean felt truly ashamed. Not only had he frightened the poor woman, he had reduced her to returning to her room to pleasure herself. She was no prude, she could obviously come—she just couldn’t manage to bring herself to tell him how, so he could bring her to greater heights, or at least share in her pleasure.

Mr. Dean straightened his back, ready to meet the challenge. He would bring Michelle back downstairs, lock her in one of his activity rooms, one way or the other—he would heft her over his shoulder and carry her down kicking and screaming if he had to—and then he would make her come so thoroughly and so often she would be walking bow-legged out the door.

He walked silently up behind her and whispered in her ear.

“One night,” he said. Her head turned. He could see the goose bumps spring up on her sensitive skin. “Give me just one night, and if I can’t please you, I will call in one of the other hosts myself to satisfy your needs.”

“And you won’t… you won’t get rough with me, like you did before?”

“I will not do anything you don’t want me to do,” he said. It wasn’t exactly the same thing as what she had asked of him, but for the moment, it was what she needed to hear.

“Very well,” she said, turning around to face him. He was standing so close behind her, she almost bumped into his broad chest. She gasped and stepped back in surprise. “I’ll give you one night.” She looked up into his eyes, and her breath caught at the heat she saw there.

“Thank you,” he said in a soft voice, lowering his head until his cheek was almost touching hers. “You won’t regret it,” he whispered. She shivered.

Pleased, Mr. Dean strode out of the room, leaving her flustered and, he recognized, highly aroused. But he had work to do. He had to prepare for the night ahead, and to do that, he was going to need some help.

~ * * * ~

Mr. Dean went looking for Mr. Shern. Mr. Shern was a fellow host at the Hotel Bentmoore, but he worked with different types of cases than Mr. Dean.

Shern specialized in the innocent female: women both young and old whose lack of experience kept them from reaching their full sexual power and appeal. He had a flare for taking young rich aristocratic brats, barely out of the school room, and turning them into full-fledged beauties, poised, refined, and fully aware of their sexual prowess. He also sometimes worked with women who had faced a sexual trauma and needed help to overcome. Many women used him almost like a sexual therapist.

Mr. Dean found him in the workout room, doing arm reps. Thankfully, there was no one else in the room, and Mr. Dean shut the door behind him. Mr. Shern turned at the noise, looking at him in surprise.

“I need your advice, Shern,” Mr. Dean said.

“That’s a new one,” Mr. Shern replied, putting the dumbbells down on the bench.

“Yeah, well, I’ve got a unique case here.” He laid out everything that had happened between him and Michelle, leaving out nothing about his impressions, his concerns, or the way he had mistreated her. By the time he was done, Mr. Shern was shaking his head and chuckling.

“An obviously classy lady, not a sub, who’s here on her own volition, and you turn her around and spank her—in the meeting room? When discipline wasn’t specified, or even discussed?” He asked, his expression incredulous. “Well, you took a risk…and it certainly backfired on you.”

“Yes, and now I have to make things right. The problem is, this woman is so closed-mouthed, she can barely articulate herself. She couldn’t even bring herself to say the word ‘sex.’”

“I can see how you would find that frustrating,” Mr. Shern said, laughing harder. “You’re not one to handle the shy types.”

“No, I’m not,” Mr. Dean growled in response to his friend’s ill-placed humor. “And not only that, she lied to me.”

“Oh? Now that’s interesting. What did she lie about?”

“Just some basic information. I asked her straight out if there’s anything specific she enjoys, and she said no, but it was obvious she was lying—she had something on her mind, but just didn’t want to tell me. Now why would she do that? Why wouldn’t she want to just tell me if there’s something she enjoys, so I can help please her?”

“Well, that’s an easy one to answer. She’s ashamed.”

“Ashamed?” Mr. Dean sat down on the bench, surprised. “Why?”

“There are many reasons why women get ashamed of these things. Sometimes they think what they want is wrong, or dirty… sometimes they’re ashamed of their own fantasies. It depends on their upbringing and their hang-ups. But in these cases, you really have to delve into the mindset of the woman, figure out what’s stopping her from exploring, and enjoying, her sexuality completely.” He laughed in the face of Mr. Dean’s stricken expression. “You’ve really never had to deal with a woman like this before, have you? I’m guessing she’s probably pretty innocent, unaware of her own sexual appeal, and for whatever reason, feels guilty of her own passion. Maybe even afraid of it. You need to overcome all that.”

“And how am I supposed to do that?” Mr. Dean looked overwhelmed. Mr. Shern laughed again; he was not used to seeing his associate and friend in such a predicament. Mr. Dean looked like he was drowning. Mr. Shern smacked him on the back.

“Dean, it’s not as hard as it sounds. Here’s what you do….”

~ * * * ~

That night, Mr. Trowlege brought Michelle straight to one of Mr. Dean’s activity rooms, and as per instruction, closed the door behind her immediately as she walked through. Michelle was startled by the sudden noise of her main escape route being sealed off. She stared at the door for a moment. There was no backing out now, she realized. She turned around and scanned the room.

Four lamps sat in each corner, and where their light did not reach, ceiling bulbs did the job. A wardrobe sat against one wall, large and stately; stained almost black and polished to a high shine, it looked more befitting a King’s royal chamber than an activity room of the Hotel Bentmoore. Across from it was the bed, large and inviting, made up in crimson sheets and matching pillows—but there were no blankets.

Next to the bed were side tables that matched the wardrobe, and a strange metal wheeling-tray, which at the moment, lay covered with a small towel. Next to the tray, leaning sideways against the wall with his arms crossed, was Mr. Dean.

She was not ready to acknowledge her host just yet, and so kept looking around the room. It was then she noticed the two poles, stretching from floor to ceiling, set about three or four feet apart from each other. She looked them both up and down. They didn’t seem to be support columns, and they weren’t there for aesthetics. In fact, they looked like stripper poles.

“They’ve been screwed in tight,” Mr. Dean said, “And can take a lot of weight on them. I’ve tried them out myself, many times.”

Michelle would not look at him as he came forward. She was too nervous.

“Why would someone put them in the middle of the room like this?” She asked. Was he going to conduct some sort of strip show for her? Did he expect her to do it for him?

“Why indeed?” Mr. Dean replied, a slight smile curving his lips. “I think you’ll understand soon enough. Are you ready to begin, Michelle?”

Michelle finally turned to look at him, her expression filled with unmasked trepidation. Mr. Dean was wearing a pair of dark suit pants, creased and belted at the waist. But he wore no shirt, and with his arms crossed in front of his chest the way they were, he looked very wide, and very strong. The heat in his eyes directed her way was potent and overpowering, and made her draw back.

“What are you going to do to me?” She asked in a throaty whisper. Mr. Dean took a calming breath. He was not used to his guests asking such questions; he was used to taking control, letting his guests know only as much as he wanted. But he would have to make allowances for this one. He would go slow and easy—at first. Once he discovered what her secret was, what she was hiding from him, he planned on using that information to his full advantage.

“Nothing that will hurt you,” he said. “Here, let me show you.” He motioned her over to the two poles. Michelle stood between them, looking at her host curiously; and then, getting the idea, she grabbed onto the poles, one in each hand. The stretch wasn’t bad. She could grab both tightly and still bend her elbows.

“There are going to a few very simple rules tonight,” Mr. Dean said, moving behind her and talking gently into her ear. She could feel his warm breath against her skin. Her hands tightened around the poles. “All I’m going to ask you to do tonight is one thing: hang on. Don’t let go of the poles—don’t take your hands off. Just keep grabbing them, and we’ll do fine.”

“You—you want me to just hold on to the poles? That’s it?”

“Yes. I’m not even going to restrain you in any way. If you can’t help it, if you have to let go, there will be no repercussions. But I’m asking you to try not to.”

“But what will you be doing?”

“I am going to touch you.” Michelle took a sharp intake of breath, and Mr. Dean moved to face her. “I will be gentle, Michelle, and move slowly. If at any point, I am doing something that makes you feel uncomfortable, tell me, and I’ll stop. Do you understand?”

“Yes,” she said. Her voice was ragged and afraid. But she had agreed, and Mr. Dean took a breath of relief. He was awarding this guest more control than he ever had to any other woman. But if this is what she needed to remain here, where he could get his hands on her and help her reach satisfaction, than he would oblige her wholeheartedly.

“One more thing,” he said. Mr. Dean moved back behind her, taking a long strip of soft black leather out of his pocket. “You will be blindfolded.”

“What? Why—” Her question was cut off as she felt the blindfold come over her eyes and tie around her head. She touched the soft leather on her face. It wasn’t tight or uncomfortable, but it hadn’t been expected, either.

“Hands on the poles, Michelle,” Mr. Dean reminded her. Michelle brought her hand away from her face and gripped the poles. “I want you to focus on what I’m doing to you, what you’re feeling,” Mr. Dean explained. “Remember, if I do anything you don’t like, you can tell me, and I’ll stop. There’s nothing to be afraid of. Do you understand?”

“Yes,” Michelle whispered. But it was clear she was afraid, despite the power Mr. Dean was offering her. He would have to tread carefully.

“Good. Let’s begin,” he said.

He pressed his weight into her back, not a lot, but enough that Michelle had to hold on tight to the poles so she wouldn’t stumble forward. She was such a tiny woman, he thought; Mr. Dean shadowed her entire form. He could hear her heavy breathing, feel her back heaving against his chest.

He dipped his head into her hair and took a deep breath: she smelled of lavender, sweet and feminine. Carefully, he unclasped the pin from her hair, and felt her thick tresses fall into his hand. Her hair was long, it turned out. It fell past her waist.

“You should wear your hair down more often,” he murmured. Michelle didn’t answer.

Spanning out his hands, he spread his fingers over her tightly sealed fists gripping the poles, then began to trace his fingertips up her arms, over her shoulders, and down her midsection. Michelle jumped a bit, tickled; but then she quieted back down. Mr. Dean smiled.

Through her shirt, Mr. Dean ran his hands up and down her wiry arms, around her soft sloping shoulders, and across her lightly muscled back. He massaged her neck a bit, kneading his hands into her flesh. Michelle relaxed and let her head lop to the side.

He moved down her spine, rubbing his thumbs against her skin in deep, circular motions, then pushed his hands back up and stroked her arms again, but harder this time. He could feel Michelle’s tension slip away as he massaged her, lulling her into a sense of comfort.

His hands came up to graze her collarbone; and then, slowly, they began to descend into the V of her shirt. Michelle’s head snapped back up. She stood up straight, holding her breath in anticipation.

Mr. Dean’s warm hands disappeared into her shirt, pushing underneath her bra. They lightly grazed against the soft skin of her breasts, then squeezed them ever so lightly. Michelle gasped. Mr. Dean stopped, but when Michelle didn’t immediately protest, he squeezed them again.

To his surprise, her large breasts were real, and just as full as they had looked through her clothes. Michelle didn’t wear a padded bra after all. Her tits felt warm and heavenly in his hands, and he kneaded them inside the confines of her bra cups. When he felt her nipples pressing into his palms, he grazed them with his thumbs, then pinched them softly between his fingers.

“Oh!” Michelle cried. Mr. Dean let go a bit, but when it was clear Michelle would say nothing to stop him, he grazed her nipples again, then pinched them harder for a brief second before letting go to knead her soft flesh. Michelle arched her back, pushing her tits into his hands, tensing at the teasing assault on her nipples.

Now Mr. Dean alternated his movements, kneading, stroking, grazing and pinching. Michelle’s head swung from side to side as her breath became hoarse and raspy. She had very sensitive nipples, he discovered, and was clearly enjoying all the attention he was paying them.

He gave her a moment to collect herself, then, with nimble fingers, began the process of unbuttoning her shirt. It was obvious Michelle could feel his hands moving against her skin; goose bumps rose across her flesh.

Mr. Dean was afraid he would have to help her remove her bra to get better access to her breasts, which would mean allowing her freedom from the poles, if only for a moment. But he was in luck: the tight stretching material had a front clasp, nestled between her snugly-fitted tits. He undid the clasp now, and had the satisfaction of watching her heavy tits spring free.

He moved in front of her now, and spread the opening of her shirt and bra wide, getting a good look at her sleek torso and orbicular breasts. They sagged a little from their heavy weight, the dark ovoid aureoles crinkling around the brown dusky nipples. Her nipples were hard and swollen now, and he grazed one again with the pad of his thumb. Then, he circled the breast in his hand, testing its considerable weight. He lowered his head and took the nipple in his mouth.

Michelle moaned. Mr. Dean worked the nipple, stabbing it with his tongue, circling and sucking it until it distended prominently, plump and proud. He bit it softly between his teeth, and heard Michelle take a hissing breath. Then he moved onto the other breast, and gave it the same treatment. Michelle made a series of “oooh” sounds, tilting her head back, clutching at the poles.

Mr. Dean knelt down on his knees and found the zipper of her skirt. As he lowered it, he kissed the satiny skin of her stomach, dipping his tongue into the hollow of her belly button. Then, in one single pull, he lowered her skirt down to the floor.

Under her skirt, Michelle was wearing thong panties, coral pink and translucent. The shimmering material was sopping wet at the crotch; it clung to her pussy lips, barely covering the soft skin. Mr. Dean hooked two fingers into the narrow waistband circling both of Michelle’s compact hips and traced them down her legs, taking the flimsy thong with them.

Michelle’s thighs squeezed together in alarm. She couldn’t see, but she knew her host was kneeling at her feet, getting a good look at her exposed pussy lips. But Mr. Dean lifted one of her legs at the knee, pulling off her shoe, and then did the other. He spread her feet wide across the floor, moving them apart until she could feel the cold metal of the poles pressing against the sides of her feet. Michelle was now in an X pose.

“Stay like this,” Mr. Dean said. “Don’t move.”

When Michelle had opened her legs, so had her pussy lips. Mr. Dean reached down now, and, placing his thumbs on the soft flesh of her lips, he opened them wide, drinking in the sight of her wet, swollen inner folds.

“Wait—” Michelle’s voice rang out, sharp and alarmed.

“Am I hurting you?” Mr. Dean didn’t move further, but he didn’t take his thumbs away, either. To her credit, Michelle gave the question a moment of thought.

“N-no, but….”

“Then there is no reason for me to stop. Let me touch you, Michelle.” His voice was a soft plea. He lowered his face between her legs as he spoke. Michelle could feel his warm breath against her crotch. A moment later, she felt his lips nuzzling against the swollen folds of her cunt.

Michelle cried out. Mr. Dean widened his tongue and ran it up inside her folds, moving it slowly, grazing her with soft, wet licks. He lapped at her thickening moist flesh, hot inside his mouth; then he rested his tongue right on her throbbing clitoris, pulsing his tongue against it.

Michelle’s breath came out in thick gasps. Her hands moved up and down the poles, slick and wet from her sweaty palms. Mr. Dean kept up his wet homage to her cunt, lapping and sucking greedily.

Then he stood up. “Don’t move,” he ordered again, this time moving away from her. Michelle tilted her head this way and that, trying to listen to the sounds of his movements, resisting the urge to let go of the pole for the second it would take to peel down the blindfold.

A moment later she sensed Mr. Dean return. What she didn’t know was that he had wheeled over the small metal tray and was now uncovering a long smooth vibrator, one that strongly resembled the toy he had glimpsed in Michelle’s bathroom. It did not match hers exactly, but it was close enough, or so he hoped. In his other hand, he held a tube of water-based lubricant.

Michelle’s pussy was sopping wet, glistening from her own inner juices and Mr. Dean’s talented mouth. But even so, he lubed up the vibrator and rubbed it in his hand, warming it to the touch. He didn’t want to shock Michelle too badly by pressing something dry and cold against her skin.

He turned the vibrator on, and watched Michelle’s reaction to the sound of the toy humming merrily in his hand. She jerked her head up, realizing at once what the sound was.

Mr. Dean touched the vibrator to Michelle’s inner thigh, and Michelle instinctively jerked her leg away.

“Hold the position, Michelle,” Mr. Dean said, his voice stern. She dutifully put her leg down, pressing the outside of her foot against the pole.

Mr. Dean continued to slide the vibrator up the inside of her leg, letting her get a good feel of the quick, steady vibrations, watching the way her muscles tensed and rippled beneath her supple skin. Then he moved the length of the vibrator to the crease separating her pussy lips, slid it back and forth a couple times against the soft, wet slit, and pressed in.

Michelle bent forward, lowering her head all the way down, until the tips of her hair were brushing the floor; but she held the position, keeping her sweaty palms hugging the poles and gripping them hard so she would not fall to her knees. She groaned.

Mr. Dean took note of her tense movements. But he said nothing—so long as her hands and feet kept in contact with the poles, she was free to move all she wanted. The point of this exercise was not to keep her completely immobile. It was to discover what excited her, and what it was she was hiding from him.

She was gyrating her body now, undulating her torso and reedy arms between the poles like a snake dancer. Mr. Dean held the vibrator deep inside the wet crease between her legs, sliding up and down her velvety layers of flesh, watching the way her skin flushed and the reedy muscles of her waist undulated. He kept her hips steady with his other hand, holding her pressed against the persistent vibrator nestled between her pussy lips.

Michelle’s face slackened, and her fingers relaxed around the poles. A dreamy smile played across her mouth; she hummed in delight, swaying in time to her own private, sensual rhythm. Mr. Dean took note how she relaxed her body into the vibrator, how she tilted her head back in warm abandon…and furrowed his brows.

It was not enough. Michelle was obviously enjoying what he was doing, true; but there was no tension in her muscles, no sense of urgency to her movements. She was easing herself into the steady humming of the snuggled vibrator, not straining against it.

He wasn’t sure if Michelle understood the difference, but he did. She would not come this way. There was something else she needed him to do, and he needed to figure out what, or she would not come at all.

He let go of her hips and reached his hand up to pinch her nipples, one at a time. Michelle gasped, but continued to sway her body, twisting and rocking her tiny frame as before. He flicked her nipples, hard; Michelle cried out and swung her head back, but once he was done, her features slackened again.

Trying a different route, Mr. Dean tilted the tip of the vibrator inward, and lunged it inside Michelle’s tight cunt, burying it deep. He waved it around with his hand, making circular motions inside Michelle’s clinging pussy. Michelle released a long, plaintive “ahhh,” but otherwise, did not react with any rise in tension or need.

Feeling his frustration rise, Mr. Dean stood up and moved around her, sliding the vibrator in and out of her cunt from behind. Michelle danced for him, leaning her weight against his wide chest and then jerking herself forward; but even after a few moments of this blissful pleasure, she did not look any closer to coming.

He rubbed her clit as he pumped the vibrator, but not gently, oh no. His own rising vexation made his fingers press hard against her skin. Michelle leaned her head back against his chest again and sighed in delight, then continued to sway.

With a jerk of his hand, Mr. Dean pulled the blindfold off her face, and dropped it to the floor. He thought maybe having her see him touch her body would arouse her enough to send her over the edge. But Michelle kept her eyes closed, lost in her own carnal pleasure. Mr. Dean lightly pinched her clit, pulsing his fingers against her throbbing button, and got only a series of short squeals in response.

She was aroused, that much was clear. She was skimming across the edge of desire from his ministrations—she was just not showing him a single sign of how to get her up and over.

He wanted to yell in frustration. Michelle could come, he knew that. She had obviously used the vibrator in her bathroom to her own satisfaction. He was not dealing with a woman who was completely non-sexual, or physically unable to climax, or maimed in some way. But how did she pleasure herself? What did she do with the toy, alone in the dark, when it was only her own hands doing the work? Maybe she had to be lying down? On her back? On her stomach? Maybe he would have to maneuver her to the bed and try something new?

Growling at his own ineptitude, Mr. Dean lowered his eyes and watched the way Michelle’s narrow hips and high-set, compact bottom bobbed and danced under his gaze, forming tight figure-eights between the poles. Her butt was smooth and small; beneath the hem of the open shirt, the crease separating the twin domes of her buttocks dipped low, making her ass cheeks look widely sloped and, to Mr. Dean’s opinion, absolutely adorable.

Without thinking, he ran his hand down the length of her back, then grabbed a butt cheek and gave it a good squeeze. The entire mound of flesh fit perfectly into his wide, calloused hand. He smiled.

Michelle gasped. For a moment, her dancing halted, and when her hips began to circle again, they seemed to push against Mr. Dean’s hand still holding firm against her ass. Mr. Dean noticed, and a tiny kernel of an idea began to take shape in his head.

With an intent look on his face, he turned his wrist, and ran the back of his hand up Michelle’s crack, grazing the crinkling ring of her anus.

Michelle stopped her rhythmical dancing and held still.

Inspired, Mr. Dean diddled his middle finger inside Michelle’s wet pussy; then, sliding it back against her the skin of her crack, he slowly pressed his finger pad against the small opening of Michelle’s asshole.

A shudder ran through her; her eyes squeezed shut, and she let out a short, breathy moan.

But she said nothing in protest. In fact, she held her ass stock-still, as if waiting for him to continue.

“I think…finally…I’m beginning to understand,” Mr. Dean said under his breath. Michelle did not respond; she held her body motionless, tense and waiting.

Mr. Dean pressed his finger in, pushing the fingertip past the clenching ring of muscle of Michelle’s ass. But he pushed slowly, not wanting to hurt her if he was wrong. To his surprise, Michelle thrust her hips back, pushing his finger all the way in, impaling herself until he could cup her ass-cheek against his palm. The knuckles of her hands turned white around the poles as she gripped them tightly, her body tense and waiting.

And finally, Mr. Dean understood.

Michelle didn’t ask for him because of his strict brand of discipline, he realized. She had asked for him because her friend Monique must have mentioned in passing how he had tried to enter her ass. And while Monique was vehemently against the notion of anything entering her rear-gate, her friend Michelle, clearly, was not.

Mr. Dean could have roared in triumph. But he kept quiet, intent on the task at hand. Now, in complete control over the waiting, whimpering woman, he knew what to do.

He began to slide his finger in and out of Michelle’s asshole, increasing his tempo as Michelle began to groan. When her hips started to rock back against his palm, he dropped the needless vibrator back onto the metal tray and circled her ribs with his arm, holding her steady and trapping her against his chest as his finger plunged in and out of her needy hole. When that wasn’t enough for her, his one finger became two, and then three. Michelle’s tight anus stretched under the assault of his fingers; it gripped them like a tight sleeve.

“Don’t move,” he ordered gruffly. Then he let go of her completely and pulled his fingers out.

Shocked by the retreat of his talented fingers, Michelle whined and thrust her butt back, searching for his hand. But Mr. Dean stepped back; he needed to assess the situation. He looked at the tray: the vibrator lay there, motionless.

Instead of reaching for it, he grabbed the tube of lubricant sitting close by, quickly lowered his pants, and greased his stiff cock. Stepping forward once more, he set the bulbous tip of his prick inside the shadowy crease of Michelle’s bottom. Grabbing her by the hips with both hands, he pulled her back until she was slightly bent over. Then, finding his target, he fitted his cock against her pulsing, cringing asshole, and pressed in.

“Aah!” Michelle cried out, arching her back in a perfect bow-curve. Mr. Dean continued in with his assault, pushing his hips forward while he pulled Michelle’s back, impaling her ass on his cock. In a single, smooth push, he was all the way in. He could feel the smooth skin of Michelle’s ass cheeks grinding against his thighs.

“Oh God,” Michelle whispered, bending her body down until her torso was parallel to the floor. Mr. Dean could make out the deep crevasse between her shoulder blades under her shirt as she held the pose. Her arms strained back to hold the poles.

Mr. Dean closed his eyes and held himself still. Her asshole was warm, and tight, and pulsed around him in sweet agony. He held her hips against his pelvis, reveling in the feeling of her incredibly tight hole squeezing his cock.

Then, he slowly began to pull his cock out, letting it slide in the hot grip of her rectum. It seemed to try to pull him back in, milking his cock like a hungry mouth. When only the helmeted tip of his prick was still inside, he lunged, slapping the bent-over woman with his thighs and getting a shriek in response.

Then he was fucking her asshole brutally, pounding into her with hard thrusts of his hips and burying himself in as far he could. Michelle grunted and yelped, holding onto the poles for dear life. She spread her feet as far as the poles would allow, bending forward so her rear cheeks would open even more, trying to make it easier for him to ram her from behind.

As he ravaged her asshole, Mr. Dean looked down at the bent, shuddering woman, and felt all of his usual authority return in full force.

“You should have told me,” he said between thrusts, his voice grating.

“Yes,” she whimpered.

“Yes, Sir,” he corrected.

“Yes, Sir,” she groaned. The highly charged woman was jerking her body back against him, rocking on her heels and thrusting her hips back and forth, grinding her ass against his groin as he held onto her and pulled at her body. Mr. Dean used her asshole like a wet cunt, pumping in and out, feeling the stabbing thrills of her rear-gate pulling on the entire length of his cock.

As he fell into a rhythm, Michelle began matching his thrusts, caught up in the effects of her own heady thrills and trying to bring herself off.

“Oh, yes, please, yes, Sir, please,” she entreated.

Mr. Dean kept up his steady rhythm, pounding into her with powerful strokes. He was about to reach around for Michelle’s clit to rub it and help her come, when he felt a convulsive shudder run through the tiny woman. Michelle flung her head up in wild abandon, whipping him with her hair, and let out a high-pitched cry.

Mr. Dean widened his eyes in surprise. He realized, to his amazement and delight, that Michelle was already reaching her own climax, without any clitoral stimulation at all.

Little Michelle was, apparently, an anal slut.

“Oh God yes!” She screamed, pushing her ass back and doing a very good job of fucking herself on his cock. Her innards squeezed him almost painfully as she came, her asshole spasming around his thick staff like nothing he had ever felt before. The sudden stabs of ecstasy were too much for him, and Mr. Dean came himself, erupting inside her clenching sleeve, slapping against her butt cheeks until he had collapsed on top of her in shuddering release.

As the breathing of the two sweating, ragged people returned to normal, Mr. Dean pulled his softening cock out of Michelle’s shrinking hole and stepped back. Michelle stood up, leaned her weight against one of the poles, and smoothed the hair out of her face.

Standing behind her, Mr. Dean could not see her face. But after a moment, he could hear the unmistakable sounds of her crying. He came around to face her, afraid.

“Why are you crying?” He demanded. “I know I didn’t hurt you.”

“No, you didn’t hurt me,” she said, looking down and covering her eyes in shame. “But—what’s wrong with me?”

“Wrong with you?” Mr. Dean asked after a moment. “What do you mean, what’s wrong with you? There’s nothing wrong with you.”

“Look at me!” She cried. “I can’t have sex—not the right way, not the way normal people do it. I’ve never been able to come with a man the way I’m supposed to.”

“The way you’re supposed to?”

“You know, with him in my…my….”

“Your pussy?”

“Yes! But it’s never worked for me! Never! I can only come with a man’s dick in my ass!” She stretched her arms up, as if begging the heavens for help. “There must be something wrong with me! I’m a—a sexual deviant! A freak! I was hoping I could come here and learn to enjoy sex the normal way, but I can’t, I just can’t,” she sobbed. “Tell me—what man wants to have sex with a woman who will only enjoy it if he comes in her ass?”

For a second, Mr. Dean stared at her, surprised.

“You—you really think there’s something wrong with you for liking it up the ass?” He asked incredulously.

“Yes! There must be!” When she caught his look of shock, she stopped and stared at him, confused. “No?”

Mr. Dean smiled; then, in a rare moment of abandon, he tilted his head back and laughed.

“Michelle,” he said, “you and I really need to talk.”

~ * * * ~

The next night, Mr. Trowlege brought Michelle down to Mr. Dean’s favorite activity room: the large wardrobe contained much of his standard equipment and toys, primarily anal toys. Even so, he had borrowed some other choice items from the wardrobes of other rooms. He wanted a fully stocked collection at his fingertips by the time Michelle arrived.

He chose the furniture with great care, picking a piece that would not scare her straight off and have her running in the opposite direction. Once he had her immobilized, situated the way he wanted her, it would be easier to work past any lingering resistance; but he had to get her in place first, and locked in the proper positioning.

When Michelle entered the room, she was greeted with the sight of Mr. Dean looking at his furniture masterpiece, smiling in anticipation. He was looking forward to an interesting, and hopefully highly entertaining, night.

“Hello,” she said, taking him in. Like yesterday, he wore dress slacks, but no shirt; and while his imposing form still scared her a bit, she now she felt her body react in a purely wanton way. She sucked in her breath as he looked at her, his dark eyes probing. She looked down, uncertain.

“Hello, Sir,” he corrected her once again. Michelle’s eyes snapped up; for a brief second, she looked at him in defiance. But then the moment passed, and she lowered her eyes to the floor once more.

“Hello, Sir,” she repeated with a sigh. Mr. Dean knew it grated her to address him like this, but he would keep insisting until it became second nature to her. She was no submissive, he knew that now, and he would not try to dominate her the way he did most of his other guests. But at the Hotel Bentmoore, there were protocols that had to be followed. And, he had to admit, he derived a certain wicked pleasure in forcing her to bend to his authority, even in this seemingly small way.

Mr. Dean took in the sight of her: she was wearing her hair in a loose ponytail today, gathered in a red stretch-band at the nape of her neck. The long tresses weren’t completely free, but the ponytail was a vast improvement to the tight bun she had worn before.

“You look very nice,” he said, walking up to her. Michelle was wearing a black cotton sweater, thin and clingy, and a short, snug, matching skirt. Except for her high-heeled shoes, her legs were bare. The skirt was also a great improvement to the pants she worn before. Mr. Dean wondered if anything else was bare under that skirt. Probably not. That, too, would require some training.

“Thank you…Sir,” she replied to his compliment. Mr. Dean nodded.

“Are you ready to begin, Michelle?”

“I don’t know. I’m a little afraid,” she admitted. She shifted her feet nervously.

He took on a look of surprise. “Why?”

“Because you’re going to do things to me, and I don’t know if…if…”

Mr. Dean held her by her upper arms, looking down into her frightened face. His chest grazed the tips of her breasts through her sweater. He did it casually, making it look like an innocent mistake instead of the calculated move it was.

“Don’t be afraid,” he said softly, holding her by the arms. “I won’t do anything to hurt you. I didn’t hurt last night, did I?” His tone was low and soothing, but as he spoke, he began to back her into the bed, forcing her to take tiny steps in time with his as they did a tight dance across the floor.

“No, you didn’t hurt me….” Michelle’s voice was hesitant and nervous. Her feet continued to step back as her host forced her into retreat.

“And I won’t now, either,” Mr. Dean continued. “Let me prove to you there is nothing wrong with you, Michelle. You are a very beautiful, very sensual woman, and lots of men would jump at the chance to…make love to you the way you like it,” he finished, quickly amending his choice of words. He was about to say, “fuck you in the ass,” but he knew Michelle would not appreciate the vulgarity, and it would ruin the moment. She was clearly responding to his gentle, caressing tone; she wasn’t putting up any kind of fight. Yet.

Michelle’s legs hit the back of the bed. The impact jarred her, bringing her back a little. Her eyes filled with trepidation.

“What do I have to do?” She asked.

“Well, first thing is to get you undressed,” Mr. Dean answered, trying to keep his voice casual, as if he were asking her to do nothing more than share a drink with him. “Would you like to do it, or would you like me to….?”

“I can do it,” she replied.

She crossed her hands, grabbed the bottom hem of her sweater, and in one fluid movement, lifted it over her head. Then she stood up and stepped out of her shoes. But when she slipped her fingers beneath the waistline of her skirt, ready to shimmy it down her pelvis, Mr. Dean stopped her.

“Slow down,” he said, reaching around her waist and covering her small hands with his own. “Relax. We have time. Better yet—lie down on the bed. I’ll do it.” With both hands on her arms, he lowered her backward onto the bed, slowly so as not to scare her, and grabbed her skirt by the waistband to pull it down her hips. Peeling it down past her thighs, he got his first look of Michelle’s white, thin, thong panties.

They barely stretched over the mound of her pussy, cinching between her legs in a straight line and disappearing inside the tight crease of her ass, before rising up her back to the circling waistband.

His eyes suddenly mischievous, Mr. Dean dug his fingers into the thin wisp of material ensconced up Michelle’s bottom, and gave it a sharp pull.

“Hey!” Michelle squealed.

“That was rude of me,” Mr. Dean said, not at all contrite. Michelle gave him an accusatory look, but Mr. Dean was already pulling down her panties and flinging them aside.

“That’s better,” he murmured. Her pussy was smooth and shaved, and looked delicious.

At the moment, it was closed up tight, thick lips caressing up against each other; but that would change soon. Mr. Dean would not be ignoring that area completely, despite Michelle’s predilections. It would simply not be the area he would be giving his full attention to tonight. The idea of getting his hands on Michelle’s choice rump again made his balls tighten and his cock twitch.

The only thing left was Michelle’s bra, and Mr. Dean made quick work of it by pulling her up, unhooking the front clasp, and peeling it off her shoulders. He decided: one of the best inventions in the history of modern man was the front-clasping bra.

Michelle’s heavy breasts swayed a little as they were freed. Her nipples puckered from exposure to the room air.

“Now, let’s get you comfortable,” he said, trying to sound matter-of-fact. “Turn onto your belly.”

Nervously, Michelle complied. She was wound up tight, tense and stiff. But taking a lesson from what had worked the night before, Mr. Dean began to massage her, running his hands up and down the backs of her legs and thighs with gentle pressure, trying to put her at ease. When Michelle closed her eyes and relaxed, Mr. Dean moved his hands up, and began to massage her butt.

“Mmmm,” she hummed, cradling her head in her crossed arms, her eyes closed. Mr. Dean kept up his gentle kneading until Michelle had entered a state of languid contentment, completely at ease. It was time to move on.

“Let’s prop you up,” he said. Michelle didn’t respond; she looked like she was half asleep. “Move your butt up a little,” he repeated.

“What?”

“Kneel up on all fours for a minute,” he said.

Slowly, Michelle complied, raising her body onto hands and knees. Then she looked behind her to see what her host was up to.

Reaching under the bed, Mr. Dean had pulled out what seemed to be a pillow—only it was unlike any pillow Michelle had ever seen. It was large, well stuffed, and in the solid shape of a mound. “Lie down on this,” Mr. Dean instructed. “Put it under your hips.”

When Michelle continued to look at him, confused, Mr. Dean took matters into his own hands. He slipped the pillow under her, centered her across it, and pushed her back down. Michelle grunted. With her hips resting over the pillow, her ass was stuck up in the air. She felt very exposed, and tried to shimmy down the pillow a little.

But her host would not let any sense of propriety get the better of her. He held down her ass, but began to massage it again before she could protest. Michelle stopped her wiggling.

“That’s better,” Mr. Dean said. Michelle quickly decided it was good. The angle of her bottom was much better this way for his hands to knead her soft flesh. She folded her arms again and rested her cheek on the soft sheets, her ass fully supported, high in the air.

And then, with one naughty finger, Mr. Dean poked into the crevasse of her bottom and tickled her asshole. Michelle shrieked in surprise and lifted her weight off the pillow.

“Now, now,” Mr. Dean said. “I didn’t hurt you, did I?”

“No, but you goosed me,” Michelle said, lowering herself down slowly, her eyes now cleared and filled with apprehension.

“Well, see, this is a problem,” Mr. Dean said. “I’m not going to hurt you, Michelle, but I can’t have you wiggling and jumping all over the bed every time I surprise you the slightest bit. Then I really might hurt you.” He seemed to think for a minute, then walked briskly to the wardrobe and returned with a blindfold. “Let’s get this on you,” he said.

“Why?”

Mr. Dean sighed.

“Because, Michelle, I want to move you around a little and make sure you’re not going to hurt yourself. But I’ve got to use, some, uh, things, to keep you from twisting around too much, and I don’t want you to get scared. I don’t want your fear to stop us from having some fun,” Mr. Dean said, trying to choose his words carefully. He was not used to talking things out and explaining things to his guests, especially once they were inside the activity room; he was used to giving orders. Michelle had no idea she was one of only a few women who could dare ask Mr. Dean for an explanation to his actions and not get a stern spanking in response.

But Michelle was still stalling. “If you’re so sure what you’re going to do is going to scare me, why do you think I’ll like it?”

“Because I’ve had quite a bit of experience in these matters,” Mr. Dean said dryly. “But if you don’t like what I’m doing, I’ll stop. Same as before. I promise.” He didn’t move. Now was the time he had to let her think she was in control and making all the decisions. She had to agree to do this on her own free-will. Of course, if she continued to balk, he would resort to other methods. But things would go much better later on if she thought she had agreed to this little lesson of his on her own volition.

But Michelle only gave it a moment’s thought. She was worried…but she also wanted his hands back on, and in, her ass.

“Okay,” she said, burying her face in the cradle of her arms and squeezing her eyes shut. “Go ahead.”

Mr. Dean grinned; he had won. He placed the blindfold over Michelle’s eyes, brought the two strings together behind her head, and tied it tight.

Working fast while she lay still, he began to pull his supplies from under the bed where he’d hidden them. Hiding his supplies was also a new experience for him: he typically kept his tools out in the open, sometimes scattered around the room, ready to collect when and where he needed them. But he rather enjoyed this game of subterfuge with Michelle. It made the conquest that much more fun and satisfying.

The bed Michelle was resting on looked like a normal, antique, four-poster bed. But wooden slats going across the top connected the posts at both head and feet, and the short headrest had wooden slats going across it, too. What Michelle had failed to notice, resting on the large bed, were the many hooks and eye-bolts screwed into the frame: perfect for attaching lengths of chain, snap-hooks, rope…for all its innocent, elegant look, Michelle was resting on a fully functional dungeon bed.

Careful not to make too many rattling noises, Mr. Dean now set about attaching lengths of chain to different points of the bed.

“I’m going to move you down a bit,” he said. “Ready?” Without waiting for an answer, he grabbed Michelle by the ankles and pulled her down the bed, the pillow wedged beneath her pelvis dragging along with her. Michelle squealed.

When the end of the pillow met the edge of the bed, Mr. Dean stopped his tugging and let Michelle’s ankles go. Her legs now dangled down to the floor, but with her hips and ass propped up as they were, her feet could not touch bottom. She could not even graze the floor with her toes.

Quickly, Mr. Dean attached cuffs to Michelle’s ankles and snapped them into the lengths of chain. Michelle’s sharp intake of breath told him she had finally figured out what he was doing. She jerked her feet, and found them well and properly restrained to the bed.

Moving quickly now, Mr. Dean moved up the bed, took her hands, and slipped a pair of cuffs over each wrist—and then he pulled. But he had attached each cuff to a length of chain that was snapped into the opposing edge of the bed. Michelle’s arms were crossed into an X; she could not uncross them. The chains were long enough that she could bend her elbows and grip her forearms, or cradle her head in the hollow of her arms, but she could not straighten them, and she certainly couldn’t raise them.

When Michelle tested her wrist restraints and realized how quickly her host had rendered her harnessed and chained to the bed, bent over and exposed, she began to protest.

“Now wait just a second—”

His work just about done, Mr. Dean folded his arms across his chest and gazed down at her chained body, giving himself a moment to admire the view. A triumphant look covered his face. Michelle couldn’t see it, of course; she was stuck looking straight ahead at the bed post. He could take a few moments to alleviate some of her fears, he decided.

“Are you being hurt?”

“No, but—”

“So you’re not in any kind of pain?”

“It feels uncomfortable—”

“What does? The cuffs? Is it too tight somewhere?”

“No—” She rattled the chains, testing her bonds—“But I don’t like it.”

“Why not?”

“Because I can’t move!”

“That’s true,” Mr. Dean agreed. “But that’s where the trust needs to start. You need to trust me, Michelle, if I am to pleasure you. So here’s what I want: I want you to tell me if something starts to hurt. If I do something that causes you pain, then you say ‘hot,’ and I’ll stop, immediately, no questions asked. But you have to promise me you’ll only use that safeword if you’re in pain, Michelle—not if you’re just feeling uncomfortable or scared for a moment.”

Michelle opened her mouth to protest, but Mr. Dean stopped her. “I’m not saying you have to stay completely quiet. You can still tell me if you’re scared or uncomfortable about something I’m doing. If I’m pushing your boundaries, you tell me, and we’ll talk about it. I’ll help you get through it. But the safeword—the safeword is for pain only. Do you understand?”

Michelle swallowed hard.

“Yes,” she said.

“Yes, what?”

“Yes, Sir.”

“Good.” His triumph came clear through his voice. “And what’s your safeword?”

“Hot.”

“Very good. But there’s still one more thing.”

From behind her, Mr. Dean bound thick leather cuffs around Michelle’s thighs, then took his last item out from under the bed: a spreader-bar. He fit the bar between Michelle’s thighs, and fastened it into place with the help of the special cuffs. Michelle’s legs were now locked apart, spread wide and bent over the edge of the bed. She had never felt more vulnerable in her life. She whimpered.

“I know you’re new to this, and it feels strange,” Mr. Dean said soothingly. He smoothed down her hair across her head. “But you’ll enjoy it, I promise.” Michelle didn’t answer. Her chest was rising and falling fast; she was breathing hard.

“Let’s get you a little more at ease,” Mr. Dean said, having pity on her now that he had her the way he wanted. He went to the side table next to the bed and reached into the drawer to get a bottle of lube. Coating two fingers with it, he returned to stand behind Michelle’s compact and trussed up behind.

Spread as she was, he got a good inside her thin, shadowy crack: the deep division between her twin domes lay slightly open, revealing the puckering ring of her spasming anus. Beneath that was the gently sloping mound of her pussy; her cunt lips were closed and dry, but her asshole winked at him coyly.

With his dry hand, Mr. Dean splayed her ass crack even more, opening it wide. Then, with his lubed up fingers, he began to gently feel her up, running his fingers up and down her crack, tickling her asshole. Michelle groaned.

Mr. Dean set the pad of his index finger against her clenching ring. Applying gentle but steady pressure, he pressed in, testing her resistance, and quickly had his finger in all the way to the knuckle. He was amazed at her control: while the rest of her body seemed tense and stiff, her asshole allowed him easy access. A low, breathy moan escaped from Michelle’s lips as he took ownership of her rear-gate.

Mr. Dean pushed his finger in further, watching as it smoothly disappeared up her ass. He was soon cradling one of her small cheeks in his palm. His finger was pressed up tight, and he gave it a tiny wiggle. Michelle jerked. Slowly, he pulled it out; but when he pushed his way back in, it was with two fingers this time, not just one.

Thrusting fast now, Mr. Dean began to finger-fuck her ass, listening as Michelle sighed in delight at the head of the bed. Her asshole hugged his fingers, and her cries of pleasure were like music to his ears. His cock swelled and twitched, jumping for the chance to replace his fingers.

For a second, he debated whether he should slow things down, make Michelle wait to come. But then he thought: Why? It might be fun to see how many times Michelle could come tonight by ass-play alone. And her coming now would certainly do them both good, and set the tone for the rest of the evening.

But in the end, it was his cock that decided for him, straining against his pants.

As his fingers continued to dip in and out of Michelle’s asshole, Mr. Dean quickly shimmied out of his pants and flung them away. He pulled out his fingers from her warm, pulling sleeve for the few brief seconds it took to grab the lube and grease up his cock. Michelle whimpered again, this time in need.

Holding his cock in his hand, Mr. Dean opened Michelle’s plaint cheeks once more, centered his straining prick against his small target, and pushed in. He wasn’t slow, and he wasn’t gentle. He thrust fast and deep, ramming into her, all the way up to his balls in one fell swoop. Michelle snapped her head up, and a gurgled cry came from her throat; she tried to raise up her body, as much as the chains would allow. But she did not use her safeword. Her host grunted in approval.

Then Mr. Dean stood still, savoring the feel of Michelle’s clenching asshole squeezing around him, her delicate tissues hugging him tight across his long length. He grinded his hips against her butt, rubbing himself within her and pushing himself in that last little bit, pressing into her soft derriere hard with his stomach. Michelle lowered herself down and hugged the pillow at the head of the bed, squeezing hard—both the pillow, and Mr. Dean’s cock.

He pulled out, slowly, until only his helmeted tip was still inside. Then he lunged in again, pounding hard, pushing Michelle up from the impact. She let out a short shriek and grabbed onto the sheet this time.

And then he was fucking her ass furiously, grabbing her by the hips and pulling her to meet his thrusts, closing his eyes in delight and trying desperately to hang on. Michelle’s asshole was just as tight and hot as he remembered from yesterday, and it squeezed him like a vise. It swallowed up his rock-hard prick with each push of his hips.

Michelle struggled against the sheets and pulled the chains, trying to prop herself up more and meet his thrusts; but bound as she was, it was up to Mr. Dean to set the pace and force. That was, of course, what he had planned from the beginning.

But even so, Michelle was soon crying out in ecstasy, building up to her own orgasm and straining with the need for release. She whipped her head from side to side, moaning out to her god and her host, as her asshole throbbed and spasmed around Mr. Dean’s prick. Then she went up and over, coming in a clenching, locking squeeze of her muscles around his stiff length.

Her tight grip and cries of delight were her host’s undoing, and Mr. Dean came himself in blinding eruption, shooting his load up Michelle’s warm rectum that seemed to milk him to his last thrust.

As he slowly pulled his withering cock out from her, Michelle shuddered in response, getting tiny aftershocks from his depleted cock caressing her sensitive inner skin.

Mr. Dean recovered first.

“Feel better?” He asked, his voice ragged.

“Oh, God,” she answered into the sheet. Mr. Dean smiled.

“Good. I’ll give you a few minutes to rest before we continue.”

She said nothing to his statement, but rested her head on the bed as her breathing evened out. Her legs lay limp over the edge of the bed; she looked utterly spent. But the pillow and spreader-bar kept her in the wanton pose, a fact Mr. Dean found most endearing.

As she rested, Mr. Dean walked over to the wardrobe and began to pull things out, barely looking them over before loading them up onto the metal tray nearby. They were sex toys, all of them anal toys, but he wasn’t being too picky with shape or size. Tonight, strangely enough, he didn’t feel the need to pick his tools with his usual care. Tonight, he hoped to try them all, and make thorough use of Michelle’s adorable little ass before their evening came to a close.

He wheeled the tray over to the bed, placed the bottle of lube on the edge of the tray, and admired the neat line of toys.

“Let’s start with some beads,” he said by way of introduction, letting Michelle know he was about to begin.

“Beads?” Her voice was still hoarse, and barely above a whisper.

“Anal beads. Here, let me show you.” He took a few steps around the bed, pulled off her blindfold with a yank, and held the beads up in front of Michelle’s face. Michelle squinted for a minute to regain her focus before staring at the beads.

They looked like glass balls, hanging from a length of thin thread. It was like a strange bracelet, she thought, only there was no clasp. A short piece of the thread hung down from the last ball. As her eyes traveled down, Michelle realized that each ball grew a little bit fatter than its sister above.

“What are…what are…”

“What am I going to do with them? Why, stuff them in your ass, of course.”

“But—”

“Don’t worry. You have your safeword if you start to feel any pain. Otherwise, it’s just the fear talking, right? I haven’t hurt you so far, have I?”

She didn’t say anything, but shook her head no.

“You should learn how to enjoy your ass to the fullest, Michelle—there’s nothing to be ashamed of. So let’s do this. It’ll be fun, I promise you.”

He returned to his spot behind her and carefully greased up each ball on the string. Then, with a look of happy anticipation on his face, he held apart her ass cheeks.

“Bead number one.”

He pressed it against her asshole, still spasming from her orgasm minutes before. The crinkled ring glistened with lube, and puckered in reaction to the sudden poking. But the tiny ball popped in fast, and soon disappeared. Michelle gasped.

“Bead number two.”

Mr. Dean had to poke this one in a bit, but like its sister, it, too, went in happily enough.

“Bead number three.”

This one needed slightly more effort, as the ring of muscle stretched around the widest rim of the ball. Mr. Dean had to push it in with his finger, sliding it deep inside Michelle’s tight rectal sleeve next to the other two. She groaned.

“Bead number four.”

He applied steady, unrelenting pressure, mesmerized as Michelle’s asshole swallowed up the thick ball. It sat right on the other side of her gate; her anus flared and constricted, as if trying to push the ball out. But it was about to accommodate something even larger.

“Bead number five—last one. Try to relax.”

Mr. Dean pushed the ball hard against her tight ring. At first, it would not give. Then, slowly, her hole stretched and dilated, widening around the huge orb. Michelle whimpered and squeezed her eyes shut. Her asshole throbbed around the stubborn ball that was filling her up to the hilt.

Even after the widest part was through, Mr. Dean had to keep pushing it in the rest of the way, making space inside Michelle’s stuffed, tight channel. But by the time he was done and had let Michelle’s ass cheeks snap shut, the only thing he could see was the bottom length of the string, hanging down from Michelle’s bottom like an obscene tail.

Michelle twisted her hips above the pillow, struggling against the chains and spreader bar. Her ass felt stretched wide, pulled taunt, and packed full. It throbbed, and ached a bit from the fullness…but it didn’t exactly hurt, she realized. In fact, the fullness was beginning to feel rather good.

“I’m going to pull them out now. Ready?”

Before she had time to respond, Mr. Dean grabbed hold of the bottom string hanging out of her ass, and pulled the balls out of Michelle with a steady yank. The thrilling sensation of the balls being pulled out of her clenching asshole sent a shocking jolt of pleasure up Michelle’s spine, hitting all the right nerve endings. She let out a high-pitched, stuttered yell, feeling her asshole pull, stretch, and close…pull, stretch, and close…Five times over. And then it was done.

“How was that?” Mr. Dean asked politely.

“Again, please, Sir,” Michelle said.

Smiling broadly now, Mr. Dean did as she asked, stuffing her with an ass full of beads, and then pulling them out in rapid speed. By the time he had pulled out the last bead on the third round, Michelle had felt very close to coming again.

“Let’s move on to something else,” Mr. Dean said, placing the string of anal beads on the metal tray. He kept it away from the clean toys, so as not to get any cross-contamination. “I’m going to try an anal dildo on you. This one happens to be made out of glass. You should learn this, Michelle—anal dildos are different from regular dildos. Regular dildos are typically tubular in shape. Anal dildos, the good ones, have a wide handle at the top, and a slightly narrowing notch beneath it, where your asshole can close in, to keep you from swallowing the whole thing up inside. If you’re with a partner, and your partner is holding onto the toy, you don’t have to be so careful about what the end—the flange—looks like, you can just ask him to make sure it doesn’t get sucked up your ass. But if you’re playing with yourself, you should always have a wide handle to grip. Here, let me show you.”

He moved around to show her, but when Michelle caught sight of the huge, obscene-looking dildo, she cringed and closed her eyes.

“Don’t turn away from it, Michelle. Look at it. It’s nothing to be afraid or ashamed of.” She opened her eyes, her face clouded with reluctance, and barely grazed over the naughty dildo.

“It’s going to fit?” She asked before she could stop herself.

“Let’s find out,” Mr. Dean said, his voice merry.

He stepped up behind her. Greasing the monstrous toy quickly, he pointed the tapered tip against her tiny bud, and pushed.

It slid in halfway before meeting any difficulty; but then Michelle grunted and pulled at the sheet, squeezing her ass closed.

“Now, now,” Mr. Dean said. “Just relax.” He waited until Michelle was in the middle of a deep breath, then pushed the dildo in with his palm against the base, oozing it up her tight channel. Michelle tried to kick her legs up and press herself into the pillow, but it was no use. Mr. Dean caressed her butt with his other hand and made calming noises to soothe her, but kept going.

Soon the toy had reached its widest diameter inside her tight ring, and Michelle’s asshole was dilated thin around the anal dildo, hugging it tight. But she could not stretch wide enough. The rim of her anus began to ache and burn, but Mr. Dean kept pushing, forcing the thing into her like a battering ram from behind. Michelle opened her mouth to cry out her safeword.

“Ho—”

“It’s in.”

As he spoke, the toy slipped the last way through. Her anus sucked the rest of it in all the way to the handle and clutched it around the base with a tight squeeze. The wide handle rested against Michelle’s soft buttocks, but the large toy had disappeared inside.

If Michelle had felt stuffed by the anal beads, it was nothing compared to what she felt now. She could feel her rectum throbbing around the glass dildo. The sensation was overwhelming. She took a few deep breaths.

“What now?” She asked.

“Now, just get used to it.” Mr. Dean stepped away from her a bit, watching her reactions as she got used to her packed ass. She was breathing hard again, squeezing her eyes shut and clenching her hands into tight fists.

If Michelle had been able to turn her head around and see the way her host was watching her, she would have been left with the sneaky suspicion he was waiting for something.

He was. He was waiting for Michelle’s natural sensuality and highly charged rectal nerve endings to take over, sending her to a place where the pain and fullness would turn into full-blown arousal, an aching need to come again.

After a few moments, when the discomfort had dissipated somewhat and the throbbing had turned into a maddening sort of wanton itch, Mr. Dean began to notice different kinds of movements coming from Michelle’s bottom. She began to shift her thighs a little inside the restraints. The cuffs and spreader bar kept her from moving too much, but it was enough for her to feel the thrilling jolts titillating her ass every time the dildo pressed or shifted a certain way inside her. Her legs trembled, and her hips began to wriggle against the pillow.

She began to make some tiny but obvious thrusting movements with her pelvis. But bound and trussed up as she was, could not move the way she wanted. The maddening tickle from the anal dildo filled her with an agitating need to do something.

“Mr. Dean, um, Sir….”

“Yes?”

“Could you, um….”

“Could I what, Michelle?”

“Um…Jesus. Could you….?”

“What? You’ll have to do a better job than that, telling me what you want.”

Michelle turned her head over her shoulder as much as she could to try and find her host with her eyes, but he was standing too far behind her. If she had been able to see him, she would have noticed his obvious look of smug satisfaction.

From the beginning, Mr. Dean had wanted her in a position where she would have to tell him exactly what she wanted him to do. He would make no more assumptions. She would have to learn how to ask to be fucked in the ass, loud and proud. No: he would get her to beg for it. Only then could she begin to get over her obvious, and misplaced, feelings of shame surrounding her sexual needs.

“Please, Sir, I….” She halted.

“Come on, Michelle. I know you have the necessary vocabulary. Finish the sentence. What would you like me to do?”

“I want you to, um…oh god…I want you to move the dildo?”

“You want me to take it out?”

“No, no. I want you to just move it around a bit.”

Reaching a hand out, Mr. Dean took hold of the flange pressing against her smooth buttocks, and screwed it in even further against Michelle’s quaking twin domes, twisting it hard as he pushed. Michelle twitched and moaned.

“Like that?” He asked, taking his hand away. He would not give her any more relief than what she explicitly asked for.

“No… yes…could you um….” Taking a ragged breath, she said in a rush, “could you pull it in and out?”

Feeling truly wicked now, Mr. Dean pulled the dildo out just enough to get the widest part through the squeezing circle of muscle, then poked it back in. He did this a couple times. Her asshole was looser now, but even so, the wide toy popped in and out through the circular gate.

“Like that?” He asked, his voice light. Michelle’s eyes flared. She twisted her head around again, trying desperately to find her host. There could be no doubt now he was toying with her, and enjoying it, too. She groaned.

“Sir, please,” she implored. Why had she agreed to this? She was an idiot, she decided.

“You will just have to pick your words better, Michelle. Remember, I’m here to help you, but I think you need a lesson in how to say what you need. Just tell me exactly what you want—and how much you want it. There’s nothing embarrassing about telling a man exactly how to please you.”

She pushed her face into the mattress and groaned again. But he would do nothing to alleviate her suffering unless she asked, and now she needed his help, badly.

“I want you to thrust the dildo in and out of me,” she said in a muffled voice.

“What was that?”

“I want you to thrust the dildo in an out of me!”

“So…you want me to fuck you with the dildo?”

“Yes.”

“In the ass?”

“Yes,” she said, her voice cracking.

“So say so—or better yet, ask. Ask to be fucked in the ass with the anal dildo.”

“Sir, please fuck me in the ass with the anal dildo,” she whispered.

“Much better,” Mr. Dean said in approval.

He began to pull the large toy in and out of her, all the way, watching as her asshole stretched and closed around the tapered toy. He thrusted fast, pushing hard, ramming the toy through her clenching hole…and very quickly, Michelle’s whole body began to tremble. She jerked inside her restraints. She thrusted her pelvis between the pillow beneath her hips and the dildo impaling her from behind, moving her body back and forth as much as she could and trying to set her own pace. But very quickly, Mr. Dean realized what she was trying to do, and wouldn’t let her get away with it. When she pushed back, trying to stuff herself with more of the toy, he pulled away.

He would not let her come so easily, she realized. His “lesson” was not over yet. She would have to give him even clearer instructions on how she wanted him to violate her ass, however humiliated she felt about it.

“Slower, please,” she said. Mr. Dean slowed down, but also made his thrusts more shallow.

“Deeper.” Her voice was soft and throaty. Mr. Dean pushed harder with each poke, the way he had before.

“God, yes,” Michelle whispered. “Now…circle it a bit?”

With the dildo still up her hole, Mr. Dean circled it wide around her rectal rim, watching as her muscles relaxed even further.

“Oh god, that feels so good…now pound me, hard.”

Mr. Dean stopped his hand. “Ask nicely, Michelle.”

“Please Sir…please pound my ass.” She flung her head up, ready to submit completely and say whatever he needed her to, so long as in the end, he would finally let her come. “Please, fuck my ass with the anal dildo, hard, pound my asshole hard and fast until I come, Sir!”

“Very nice,” Mr. Dean said, impressed. In reward, he did as she asked, moving his hand and the dildo with blurring speed, jerking the huge toy in and out of her. Michelle could feel the orgasm building, the sensations spreading across her pelvis, until they came to a crescendo…and, with a strangled cry, Michelle came. For one second, her whole body became rigid and frozen, pulling tight against her bonds; then she relaxed completely, letting out a breathy moan.

Mr. Dean continued to ream her ass until he was sure she was done with any aftershocks, and then smoothly pulled the dildo out of her. Her asshole closed shut as the well-used toy exited her body. Michelle barely responded; she was too depleted.

“I think you’re finally beginning to get it, Michelle,” Mr. Dean said, gazing down at her heaving back and flushed face. “You’re doing great, by the way. But I think there’s more we can accomplish tonight.”

As Michelle recovered from her second orgasm of the night, Mr. Dean looked to the metal tray, and picked his next toy.

“Let’s move on to something that vibrates,” he said. “You’re used to having a vibrating toy in your ass, no?” He didn’t mention he’d seen her vibrator that day he’d come into her room and spied into in her bathroom. Michelle’s eyes narrowed, wondering how he’d known. “I’m guessing, though, you didn’t know about anal vibrators,” he continued. “Again, they are made differently from vibrators that go inside your pussy.”

He rubbed his hand lightly inside the gaping lips of her cunt; Michelle gasped. Her pussy felt swollen, wet, and very, very sensitive. She was not used to feeling like this after she came. Then again, she was not used to coming twice in one night, either.

“The anal vibrators have the wide handles, same as the non-vibrating kind. But they come in all lengths, shapes, and sizes…even textures. Here, I’ll show you one.”

He came around again to show her, and this time, Michelle looked at the toy with some interest. It wasn’t tapered like the last one. It had a round, smooth head, and kept its basic tubular shape until the narrowing orbit around the base. But it was studded with tiny bumps down its long length, hard knobs that would rub against her inner skin.

“Let’s get this in you, see what happens,” Mr. Dean said.

Michelle’s eyes furrowed. She was not afraid of any pain; she was beyond that. But she felt drained. She wasn’t sure she would be able to come again.

Mr. Dean took his place behind her, coated the novel vibrator with lube, and pressed it against Michelle’s slick asshole. Her anus squeezed in protest. She had tightened up considerably after her last orgasm. She would need some inducement.

So he used his fingers first, pushing them in and spreading her open from the inside. Michelle groaned softly.

“Relax,” Michelle,” Mr. Dean instructed. “You’re all tight back here.”

“I’m not sure I can come again, Sir,” she said, voicing her fear.

“It’s okay if you can’t. Just learn what feels good. Relax and enjoy what I’m doing to you,” he replied, dilating her asshole with his fingers as he spoke. Michelle took some deep breaths and relaxed, enjoying the manual stretching.

When he felt she was stretched enough, Mr. Dean set the head of the toy against her hole and pressed in. He had to go slow; every time a bump went through the ring of muscle, Michelle’s sphincter would contract around the vibrator. But at last it was in, and Mr. Dean twisted the knob at the base to turn it on.

Vibrations shot up her back, making Michelle stiffen and squeal. But Mr. Dean let the toy be, watching as his guest started to accustom herself to the strange sensations.

“I’ll be right back,” he said. Then, mischievously: “Don’t go anywhere.”

“Wait, where are you going?” Michelle asked in alarm.

“Just to wash off a bit,” Mr. Dean replied. “I’ll be back in a minute.”

“But what about the vibrator?”

“It’s not going anywhere, either,” he chuckled. Then he walked across the room and disappeared through a door that had been well hidden by both the wood paneling and the angle of the large wardrobe. Michelle realized there must be an adjoining bathroom back there, and he was going in. To wash, he had said. Why did he need to wash? What the hell did her host have planned now?

In Mr. Dean’s absence, Michelle could do nothing but try to relax and get comfortable with the deep-rooted rumbling in her ass. She was accustomed to having a vibrating toy inside her, but not one this large, and certainly not one textured. And she was used to having control over its use.

After a couple moments, the feel of the sharp bumps churning inside her narrow channel became a maddening tickle, a titillating buzz, and she felt herself grow wet between her legs. Sweat, and a heavy dose of her own inner cunt juices, coated her thighs; she knew she was slick with it. Her pussy felt flushed and swollen. She would have scissored her legs if she could have, but the spreader-bar prevented her from even that small relief. She could nothing to help herself and alleviate this rising, aching need.

Where the hell was her host?

After a maddening amount of time, Mr. Dean finally appeared from around the wardrobe. He looked slightly damp, relaxed, and completely at ease in his nudity. Michelle’s eyes immediately went to his prick, and noticed it was soft, but thick. He was looking down at her plugged, humming bottom, but when he caught her looking at him, he met her stare head on. Then he gave her a smug smile.

He knew exactly what she was going through, she realized. He had been in control of everything that had happened between them since the moment she had entered this room. He knew what he was doing when he had left her alone with the toy ensconced up her ass; he knew that, without even working for it, he could reduced her to a state of mindless need. She was being primed to submit to whatever he instructed, and she didn’t even have the will to protest. She was certainly in no position to fight back. All she could do was capitulate. The only question was when.

Dignity and principles were done with. All she wanted now was to come again, without having to torture herself for it. But if she asked for his help nicely enough, asked quickly and got it over with, he would have to help her, right? Wasn’t that the deal?

“Sir, could you please play with the toy in my ass, could you please—”

“Not yet.”

“What?”

“I have a few questions for you first. Answer them for me, and then I’ll play.”

“But—”

“It should only take a minute.” He knelt down on one knee by her face, resting an arm on the bed as he looked into her eyes. The toy hummed in the background.

“So you play with yourself with a toy in your ass, yes?”

Michelle turned her head away and buried her reddening face in the cradle of her arms. She wanted to ignore the question. No, what she wanted to do was get the hell away from this man who had no mercy. But her growing need could not be denied, he would not release her, and he would not help her unless she answered his questions. Were all the hosts of the Hotel Bentmoore this evil? Or just this one? How could someone so merciless know how to make her come so thoroughly and so often?

“Yes, I use a toy in my ass.”

“Do you touch yourself in any other way?”

“Yes,” she admitted, her voice hoarse. “Well, sometimes, when I need to.” It was hard to think when the vibrator was pushing all thoughts away except the need to come.

“How do you touch yourself?”

“What do you want me to do, show you?” She snapped. She flailed her hips and flung up her feet as much as the chains would allow, struggling hard within the restraints.

“I want you to tell me,” Mr. Dean said patiently, ignoring her vain attempt to lash out her frustration. “Describe to me what you do.”

“Oh, God.” Her mortification complete, Michelle covered her head with her arms. Her host would not stop until he had broken through her last shred of modesty, decency, and defiance. He would bring all her secrets to light, play with her as he wanted, and in the end, break her completely.

So be it. She was done trying to fight him. All she wanted now was to come.

“I…I tap myself.”

“You tap your clit?”

“Yes.”

“Say it.”

Michelle’s voice quivered. “I tap my clit, Sir.”

“Okay. How hard?” He walked around her and stood behind her spread legs. With his hand, he reached under, spread her pussy lips wide, and with one finger, lightly began to tap her clit. Michelle groaned.

“Like this, Michelle?”

“No, ah, a little harder, Sir.”

Mr. Dean tapped harder. “Like this?”

“Oh. Oh god. Yes, but harder. Sir.”

With his entire hand, Mr. Dean began to lightly slap her clit.

“Like this?”

“Yes, like that, oh god, yes, that’s good, don’t stop.”

“That’s not a tap, Michelle. That’s a slap. Now say, “I like to have my clit slapped while I have an anal toy vibrating in my ass.”

When she didn’t answer fast enough, Mr. Dean stopped his hand and waited. Michelle could have shrieked in frustration.

“I like to have my clit slapped while I have an anal toy vibrating in my ass. Sir!”

From the tone of his voice, she knew her host was smiling. “There you go. It’s not so hard to say what you want—you just needed some training. But let’s try something else with it.”

As he slapped her clit, Mr. Dean positioned his erect cock at the entrance to her pussy and began to push in. With the toy being stuffed up her asshole as it was, Mr. Dean had to ease in slowly; but once he was all the way in, having made a place for himself inside her snug and wet cunt, he began to pump in and out, thrusting his hips with even strokes. He could feel the reverberations of the novel toy coming through her thin membranes. He pumped harder.

“How is this, Michelle?” He asked her between thrusts.

“It’s, oh, it’s good, it’s very good, Sir,” she said breathlessly. Michelle felt utterly packed, stuffed both fore and aft, and could focus on nothing but the pleasurable thrills coming from her entire pelvic area: the toy humming in her ass, her host’s thrusting prick inside her sopping pussy, and his hand slapping against her clit.

“Oh, oh, oh!” The shocking jolts of pure erotic pleasure grew in intensity until she couldn’t hold back any longer. She came in blinding light, craning her head back and screaming like a wild animal.

A minute later, her host joined her over the edge, pumping into her pussy with hard thrusts, and groaning loudly as he came.

This time, it took Mr. Dean a couple minutes to recover. After he pulled out, he sat on the edge of the bed, breathing hard. Then he turned off the droning toy still going in Michelle’s shuddering ass and carefully pulled it out of her.

As she felt him pull the toy out, she groaned. “I’m done,” she declared. The toy rubbed against her sensitive inner flesh as it left her, each bump jolting her ragged senses.

“Are you sure?” Mr. Dean asked, disappointed. “We have time, you know. I can give you a break. I have more toys I think you should try.”

Michelle gave it a moment of thought, then smiled at Mr. Dean. After the amazing orgasm he had just given her, she felt much more generous toward her host. “Well, maybe just one or two,” she agreed. “But I really don’t think I can come again.”

“That’s what you thought last time,” Mr. Dean said with a smile.

In the end, Michelle did come again, twice more that night, and Mr. Dean had her yell “I AM AN ANAL SLUT” each time she came. He also released her from her bonds at some point, sure now she would not try to struggle or fight him. This first lesson was done, and he considered it a resounding success.

Mr. Dean tried to get yet another orgasm out of her, but by that time, Michelle was practically unconscious, and no longer responding to any stimuli on either ass or pussy. But Mr. Dean felt far from defeated. He felt invigorated, and immensely proud of the work they had done together.

As he helped Michelle get dressed, he smiled at her languid movements. She was half asleep on her feet. The liaison would have to physically help her get back to her room.

And now he would have to utter the words he had been dreading to say all night. But it had to be done. Hosts of the Hotel Bentmoore had their own rules and regulations to follow.

“I would love to be your host again on your next visit,” he said. “But there are other hosts here, all very qualified to help you and each with their own strengths. If you want to try someone else, I can give you names and suggestions—”

“No, that’s okay,” she answered in a dreamy voice. “Maybe at some point I’ll want to try one of the others, but for now, I want to stay with you. You…you give me what I need, even when I don’t know I need it.”

Mr. Dean gave a sigh of relief. “Thank you, Michelle,” he said. “You’ll be visiting the hotel again soon?”

“Oh, yes. Very soon. As soon as I can get away.” She smiled. “I am so happy I didn’t leave before.”

“Me, too,” Mr. Dean replied.

Mr. Trowlege arrived. He had to hook an arm around Michelle’s waist and support her over his shoulder to help her out the door—nothing he wasn’t used to. Michelle made her way drunkenly down the hallway, hanging on tight to her escort, who was trying very hard to make sure she didn’t fall.

Mr. Dean watched them go until the elevator closed. The grin never left his face.

~ * * * ~

The next morning, Mr. Dean made his way back to Mr. Bentmoore’s office and knocked on the door softly. He was not expected, but Mr. Bentmoore allowed him entrance anyway.

Once seated, Mr. Dean gave his boss an accusatory look across the desk. Mr. Bentmoore was grinning, and obviously trying not to laugh outright. Mr. Dean sighed, then shook his head.

“You knew, didn’t you?” he asked, chagrined.

“I have no idea what you’re talking about,” Mr. Bentmoore replied.

“You knew Michelle is an anal slut.” The label came out like a term of endearment.

“I didn’t know, no. But I had a suspicion, based on some of the things she said over the phone. She mentioned how you’d tried to make use of her friend Monique’s ass, you see. I thought it was a strange thing to mention—unless she was looking for some of the same.”

“Why didn’t you tell me?”

“Because you deserved a bit of a challenge. You’ve become too used to having it easy, Dean. Women telling you exactly what they want, and tripping over their feet to please you—that’s not how you keep your skills up as a host of the Hotel Bentmoore. You need to get into a woman’s head once in a while. And you see? You clearly did need a brush up on your skills. You almost lost her.”

Mr. Dean breathed in heavily, moving his eyes away and focusing somewhere on the far wall. He thought about Mr. Bentmoore’s words.

Mr. Bentmoore was right, he had almost blown it with Michelle. But in the end, it had worked out. Better than worked out: he was already looking forward to Michelle’s next visit, when he could introduce her to more types of anal stimulation. There were enemas, probes, speculums, ginger…different positions, different tools, hell, they could try different furniture: chairs, tables, desks…the possibilities were endless. And he planned on being the first one to try them all out on Michelle’s delectable ass.

“Thanks for giving her to me,” Mr. Dean said. For him, a moment of rare sincerity.

“No problem,” Mr. Bentmoore replied. He looked down at his papers. “Now, I have another new guest visiting us next week, and it sounds like someone right up your alley….”