Inside the Hotel Bentmoore: Training Ella

“WELL NOW, DID YOU HAVE a good morning?” Mr. Cox asked her, smiling wickedly.

“Yes, Sir, as a matter of fact I did,” Ella replied. “I took a short hike around the hotel with one of the tour guides, and took a long hot bath before lunch.” She met his eyes head on.

His brows creased.

They were back in the activity room they had used the night before, facing each other for the first time since Mr. Cox had left her wanting in her room.

He looked fresh and clean again, his features sharp, his eyes clear. He wore a different suit now, crisp, starched, with his fresh white shirt tucked into his pants above a thin black leather belt.

His arms were slack at his sides, and Ella noticed the cuffs of his shirt were fastened tightly around his wrists, accentuating his wide knuckled hands.

He studied her expression, pursing his lips. “So you’re nice and relaxed now, are you?”

“Yes, Sir.”

“Because of the hike, and the bath.”

“Yes, Sir.”

He crossed his arms. “Did you masturbate after I left your room this morning, Ella?”

Ella blushed at his use of the word, and turned her head away.

“Answer me,” he said. “Did you masturbate?”

“I…yes, Sir. I did.” She crossed her own arms now, facing him with obstinacy.

After he had left her room, Ella had been so angry, she’d pounded a crater into her pillow. The hike had taken her mind off her goading problem somewhat, but when she’d slipped her naked body into the hot bath, all she could think about was her unsatisfied arousal, and how unfair Mr. Cox had been to her.

She deliberated only a moment before slipping her hand between her legs under the hot soapy water and rubbing her pussy until she came. After that, she had let her body float, languid and limp.

She’d felt a certain measure of guilt, but not much. It hadn’t been fair, the trick Mr. Cox had pulled on her; and anyway, there wasn’t much he could do to punish her for it. He was still refusing to do anything to her ass and thighs until her bruises healed. The bruises were almost gone now, but Mr. Cox insisted her skin had to be completely flawless before he could mark her again.

Ella could feel the force of rebellion growing inside her once more. Her impulse to defy, to push her boundaries, test the confines of her limits, was rising in full force. Words of mutiny were whispering in the back of her head.

He wouldn’t know if she pleasured herself, would he? There was no way he could, not for sure. And if he figured it out, what would he do?

It was that bold voice which now made Ella give him an insolent, daring smile. But to her surprise, Mr. Cox didn’t meet her look of challenge with a firm stance of determination, the way he had before. His face fell, and his eyes looked sad.

“Ella,” he said, “I am so disappointed in you.”

His words hit her so hard, Ella felt like she’d been delivered a physical blow. Her mouth opened in shock as she took a step back to steady herself.

All her bravado evaporated by his six simple words. A second ago she had been feeling so smug and sure of herself; now she was sinking into shame like a stone in a puddle of quicksand.

“Sir, I….” Her voice died away. She didn’t know what to say; there was nothing she could say. “I’m sorry,” she managed.

Mr. Cox sighed and turned his head away, as if, Ella thought, he couldn’t even stand the sight of her. “Go stand in the corner,” he said.

Ella flinched at his tone. “Sir, please, I’m sorry,” she said again, trying to get him to turn his eyes back.

Look at me. Look at me, damn it.

“In the corner,” he repeated. “Now. Just—go.”

Her eyes brimmed with tears as she walked into the corner, dragging her feet along the way. As she stood facing the corner like an unruly child, shame and remorse made her tears fall thick and fast, until she had to breathe hard through her mouth to try and calm the choking sobs rising up her throat.

She didn’t know how, but Mr. Cox’s simple declaration of disappointment had managed to make her feel worse than any act of discipline ever could. No punishment could make her feel worse than this.

After a few minutes, Mr. Cox came to stand beside her. “Look at me,” he said.

Ella turned, trying to convey with her eyes all the guilt she felt, hoping she would see a spark of forgiveness in his.

“Ella, when we’re together, if you want to fight me, defy me, even provoke me enough to do a whole take-down scene with you, that’s fine. We’ll play however hard you want. Hell, I’m more than willing to rise to the challenge.”

He paused.

“But when you’re on your own, and I can’t see what you’re up to, you need to obey my rules. I need to know you’re not doing what you know you’re not supposed to. It’s how I can keep you safe when you’re not with me, but more importantly, it’s how we build trust. If you don’t respect me enough to follow my orders unless you know I’m right there watching you, how can I trust you? Do you understand what I’m trying to say?”

“Yes. Yes, Sir,” Ella said, her voice cracking on a sob.

He opened his arms, and she flew into them.

“I’m sorry. I’m sorry. I’m sorry,” she repeated over and over.

“It’s okay,” he said. “I guess it was inevitable for you to try to get away with something when my back was turned. But now you know better, so you’re not going to do it again. Right?”

“Right,” Ella answered, offering him a weak smile. “From now on, when we’re not together, I follow your orders to the letter.”

“And when we are together?”

Ella gazed at him, confused.

“You should still follow my orders,” he finished.

Ella pouted her lips, feeling some of her previous impudence returning. “I wouldn’t expect too much, Sir,” she said.

Mr. Cox laughed and kissed her on the forehead. “Never change, princess.” He pulled away. “You still need to be punished for masturbating without permission, but—we’ll see. What I have planned for you today might be punishment enough.”

Trepidation crept up Ella’s spine, raising the hairs on the back of her neck. “Sir…?”

“Go ahead and get undressed, then lean over the spanking bench.”

“Yes, Sir.” With all her previous defiance quelled, Ella removed her clothes and bent over the spanking bench. She could hear Mr. Cox moving around and getting things out of the wardrobe, but she waited for him to return, unmoving, looking nervously down at the floor.

“I think your ass is healed enough for some light whipping,” he said from behind her. “Don’t you agree?”

“Yes, oh yes, Sir,” Ella concurred in a breathy voice.

“I had a feeling. You’ve never felt a cat o’nine tails whip, have you? Would you like to?”

“Yes, Sir. Please.”

“Then ask me, princess.”

“Sir, use your cat o’nine tails whip on me.”

“That’s not a question,” Mr. Cox said, amusement clear in his voice. “Ask me, don’t tell me.”

Ella took a breath. “Sir, will you please whip me with your cat o’nine tails?”

“Yes, princess. Don’t mind if I do.” He flung the whip against her tender ass, and Ella moaned.

The cat o’nine tails was thinner, stiffer, and less supple than most of the floggers Ella had felt up until now. She imagined it felt closer to what a real whip would feel like: stingy and sharp. This cat o’nine tails had at least half a dozen cords snaking out of the handle, and they all whapped against her skin with piercing, biting heat.

Mr. Cox started on her ass, but quickly moved up her back, hitting her sides and shoulder blades. Ella relaxed against the bench and enjoyed the whipping, moaning and gasping now and then with pleasure. She could feel herself sinking into subspace, and while before she would have tried to stop the scene before it went too far, now she let herself go, enjoying the ride.

After a few minutes of blissful torture, she heard Mr. Cox’s voice next to her ear.

“You like?”

“Oh, yes, Sir,” Ella whispered without opening her eyes. “It’s wonderful.”

“Good. Now get up.” He yanked her up by the hair, and Ella let out a tiny cry. The sudden assault on her hair had not been expected.

Mr. Cox, holding her by the back of the head, pulled her to the bed and threw her on. Ella turned over to gaze at him in flustered surprise, and watched him undress and climb onto the bed.

He lay down on his back. “Fuck me,” was all he said.

Smiling now, Ella climbed on, happy to comply. She straddled his hips and reached around to grab his cock, aiming it right into her pussy. As she slid down, she could feel his prick rub against her sensitive inner folds, filling up her hot wet cunt. She bit her lip and furrowed her brows, trying to accustom herself to the positioning.

Mr. Cox reached up his wide hands and pinched her nipples, making her eyes widen and refocus on him. “Fuck me,” he said again.

Ella braced her hands on his chest and began to slide up and down his cock, slowly, letting her natural oils ease his way. She let her body stretch and relax around his hard length; then, after a few careful thrusts, she began to add a slight rocking motion to her hips with each one.

Mr. Cox let her set her own speed and rhythm. He rested his hands on the mattress and didn’t touch her in any way, but after a few moments, when it was clear Ella had found a rhythm she enjoyed and was starting to work herself up nicely, he stopped her.

With one hand outstretched, he reached over and opened the bedside table drawer. He pulled out a bottle of lube, and….

“Do you know what this is?” He said, as he held up the hard shiny black thing in front of Ella’s eyes.

“No, Sir,” Ella replied, fear clouding her face.

“I think you do.” His lips curved up in a devious smile. “It’s a butt plug.” He turned it over in his hand, admiring the shape. “It’s one of the smallest we have. Despite your transgression this morning, I decided I should still go easy on you, and start you out small.” He stopped gazing at the butt plug and looked at her shrewdly. “Lean forward.”

Ella sat up straight across his thighs, feeling his hard erection pushing against her cunt wall. “Please, Sir, I’ve never—it looks so big—please, can we—”

In one fluid movement, Mr. Cox sat up, grabbed her by the back of the head, and pulled her down to his chest. “There,” he growled by her ear. “Now don’t fucking move, not until I tell you to.”

“Sir, please, please….” Ella’s pleading voice died away as Mr. Cox lubed up the thick black butt plug. As soon as he deemed it wet enough, he flung the bottle of lube back on the side table, and got down to work.

Holding the butt plug by the handle, he reached around Ella’s body, felt up and down her narrow ass crease, and stopped when he found what he was looking for: the puckering, cringing grommet of Ella’s asshole. As soon as he found it, he nestled the tip of the butt plug against it, and pressed in.

“Sir, please, Sir please!” Ella began to chorus as Mr. Cox pushed the tip of the butt plug further and further into Ella’s resisting ass. Her cringing muscles tried to close up and block him entrance, but the smooth wet butt plug slid through her clenching gate with ease.

Mr. Cox pressed his free arm across her back to keep her locked against his chest as his other hand continued to press the handle of the butt plug against her puckering, stinging asshole.

He pumped it gently in and out now, getting her delicate portal nice and lubricated before pushing the hard silicone further up her passageway. Ella squeezed her eyes shut and let out little cries of agony in his ear.

“While I enjoy listening to this, it would help if you relaxed,” Mr. Cox said. He slid the butt plug in, then out…then in, further up her butt.

“I can’t, it hurts,” Ella cried, grabbing pieces of the sheet in her fists as she felt him press the butt plug further still. Her asshole felt like it was on fire.

“It won’t hurt so much if you relax.” He pushed the butt plug another half inch into her ass, pressing his palm against the flat handle, sundering her opening wide. Ella let out a loud cry.

He held the butt plug still, but pushed Ella back up into a sitting position. She was double penetrated now, feeling stuffed and sore.

“Fuck me,” Mr. Cox ordered, his voice a low growl. “C’mon, move.”

“I can’t,” Ella breathed. “I can’t!”

“Do it,” Mr. Cox snapped. “Or I’ll push this thing in the rest of the way right now.”

Ella let out a terrified squeak and rocked her hips the tiniest bit. When she rocked forward, Mr. Cox’s prick tickled and grazed her cunt in the most delicious way; but when she rocked back, she could feel the butt plug stretching her ass, widening the breach.

“Please Sir, I can’t,” she repeated, bracing her hands on his chest.

“Yes, you can,” Mr. Cox replied. “You’ll fuck yourself on the butt plug until it’s buried all the way up there, and then you’ll come. Now rock.”

“Please!”

“Rock.” He pushed and pulled her hip with his hand, forcing the butt plug further up her ass.

Ella forced herself to rock. At least when she rocked, the feel of his prick grinding her cunt distracted her somewhat from the butt plug assaulting her ass. But every time she moved back, her own body pushed her down on the hard silicone, and it slid in a little bit more.

Wincing and straining, she rocked.

Her tissues stretched, and her asshole burned. It was like she could feel nothing except the flaming, piercing agony of her afflicted ass. At one point, Ella pulled her body up onto her knees, trying to get away from the pressure and pain, but Mr. Cox slammed her back down, driving up the butt plug. She howled.

“It’s almost all the way in, Ella,” he said. “Keep going.”

“Oh, please….”

“Keep going.”

Ella succumbed. She rocked against both Mr. Cox’s hard cock and the smooth butt plug, letting go of the last shreds of her resistance, and feeling the monstrous plug plunge into her body without hindrance.

She continued to rock, knowing she had no choice, that she would rock until Mr. Cox told her otherwise, because he could make her do whatever he wanted, he had that power over her….and as she continued to rock, the burning, aching feeling bloomed into rising pleasure. Her clit throbbed, and her cunt drenched with juices as it squeezed around Mr. Cox’s prick. Ella moaned as she began to rock harder, faster, unable to stop the growing need to come.

“That’s it, Ella. Let it in.” He pushed the butt plug, and Ella pushed back, letting the thick presence of stiff silicone fill her up with pain and ecstasy.

Her clit tingled, her skin flushed, and her anal sphincter clenched in a fiery ring of white-hot agony. Ella rocked hard and fast now, with violent movements of her hips and thighs, trying to bring herself off on cock and plug.

The pain was stirring her on. Ella reached around, put her hand over Mr. Cox’s fingers holding still the plug, and pushed them hard, reaming herself on the rigid stopper. She could hear Mr. Cox’s chuckle.

His hand was pressing into her ass now, the handle of the plug buried between her buttcheeks, the plug sunk all the way up inside her. Ella bounded on top of him like a happy rabbit, bouncing and jiggling, enjoying the thrilling pleasure and searing pain, trying to make herself come. After a few moments, her churning orgasm broke free, and she bucked her ass and hips against him with loud slaps of her body.

Each spasm milked his prick, but Mr. Cox held on until his balls felt like they were about to explode. In the last minute, he reached around and pressed the butt plug hard against Ella’s writhing body, making her stiffen and cry out. He could feel the tight sinews of her thighs across his legs, the shivering throes of her pleasure, and above all else, the incredible squeeze of her cunt around his prick.

He came himself, erupting right up her tight pussy. His body strained up as he came, pushing himself deeper inside her, as deep as he could go. Ella shoved herself back down, grinding her clit against his groin, and came again.

Tiny aftershocks shook them both as Ella fell forward onto his chest. They stayed like that for a few moments, breathing hard, shivering now and then in the cool room air.

Then Mr. Cox pulled her off by the hips, and Ella slid over.

She lay on her back, regaining her senses. But as she recovered, the butt plug lodged inside her ass began to make its presence felt with greater urgency.

“Uh, Sir,” she said. “The, um…the, you-know?”

Mr. Cox turned his head. “The butt plug?”

“Yes.”

“Say it right, then.”

“The butt plug. It’s still inside me.”

“I know.” He pulled himself out of bed, went to the wardrobe, rummaged around, and got out what looked like a mess of black rubber strips and buckles. “Get on your hands and knees.”

“Sir, what—”

He grabbed her ankle and twisted. Ella turned over with a short cry, realizing her ordeal with the butt plug was not yet over.

“Head down, ass up.”

“What are you doing?”

“You’ll see.”

Mr. Cox began to encircle the strips of black rubber around her waist and thighs, cinching them, fastening them with the tiny black buckles…and then he slipped a rubbery strip right between her ass cheeks.

He pulled.

The stretchy rubber plunged between her creamy cheeks, nestling itself right against the handle of the butt plug, nice and tight.

“Ow! God, it’s pushing in!”

“I know.” He buckled the naughty strip of rubber into place. “It’s a training belt,” he finally explained. The straps felt tight everywhere, but especially inside her ass crease, where the resilient rubber held still the fiendish butt plug.

At least that strap split into two and diverged on either side of her cunt lips, instead of digging between them and pressing against her clit. Ella was thankful for that, since she had a feeling she would be wearing this diabolical contraption for a long while. She didn’t have to wonder what kind of “training” Mr. Cox had in mind.

The rubber belt would keep the butt plug from slipping out for as long as her sadistic trainer wanted to keep it in there. It would stretch her ass, and make it ready to take something even bigger.

This was the smallest plug they had, he’d said. How big did they go?

“How long do I have to wear this thing?” She asked, looking over her shoulder.

“Until you see me again,” he said, looking at her bent form and smiling.

With the black straps hemming her supple thighs, accentuating her smooth rear cheeks, and forming a perfect dividing line disappearing straight up the middle, Ella’s ass looked like it was just begging for a spanking…or something far worse.

His vague answer made her uneasy. “When will that be?”

“In a few hours.”

“What if I have to, you know….”

“Answer nature’s call? I suggest you hold it in until you see me again, princess. If you can’t, you can remove the plug, but then you’ll have to put it back in yourself. Think you can do that?”

“I’ll hold it in, Sir,” Ella said, scowling.

Mr. Cox laughed. “Get dressed. I’ll see you in a few hours.”

Ella stood up, very, very carefully. Her eyes grew wide in shock every time the plug shifted inside her.

Mr. Cox laughed harder. “You’ll get used to it,” he said.

“I don’t know about that, Sir.”

“You’d better. You’ll be taking something much bigger up there by the time we’re done.”