The Hotel Caribe was ablaze with light and laughter. The annual Halloween Masquerade Ball was going on in the big ballroom; and the smaller ballroom was hosting the yearly Bondage Bash and Fetish show.
The place was packed; all the rooms were full and the tourists were ripe for the picking. Jennifer crept along the balconies in the shadows. Her close fitting black clothing could pass for Catwoman in the Masqued ball, or many a Dominatrix for the bashers, but in reality she was a thief. She smiled as she felt the small roll of cash inside her blouse. One or two more rooms and she'd call it a night. She was pretty good at her job. She took a 50 here, a 20 there, never taking more that that unless she found one of those super thick bankrolls. Tonight had been a pretty good haul. She toyed with the idea of calling it a night but decided to finish the last few rooms on this wing before calling it a night.
Room 316 was pretty good. Her 'benefactors' left a thick roll of notes beneath the pillow. Her eyes widened as she realized there were several thousand dollars in there. She pulled off a battered 100-dollar bill. Older bills were harder to trace in the off chance that someone actually reported the pilferage. She found a more modest stash in a shoe in the wardrobe. A mere 20 dollars would suffice there. She let herself out of the sliding glass door and hopped over to the next balcony. Room 318 was a little smarter; they'd locked theirs. Room 320 was locked, sort of. The person had locked the door, but it wasn't closed all the way. So the latch hadn't caught. She gave it a practiced jiggle, smiling to herself as the door slid open. She let herself in and started her usual search.
She was just easing the bureau drawer shut when she heard the snick of a key in the door. She headed for the balcony, but heard the door open before she got there. Thinking fast, she hopped onto the bed and arranged herself like a playboy bunny. He walked through the outer door of the suite, then paused at the sight of the black clad woman on his bed posed on his bed.
"Well, hello there, Scott," she purred, then leapt to her feet, drawing on all of her college theater experience. She gave him a shocked look and yelped "You're not Scott!"
"No, I'm not," he said slowly, "but I could be. And who might you be?" He asked in accented English with a Spock-like raised eyebrow.
"That's not important! I thought I was meeting an old friend, but obviously I have the wrong room." She attempted to flounce past him, making for the door. He grabbed her by the wrist as she passed, yanking her to a halt.
"I think it's very important. How did you get in here?"
She jerked back, trying to free her arm. "Bribery will get you everywhere, I paid the bellhop. I’m sorry I invaded your space, but I thought this was someone else's room. If you'll excuse me, I'll go find him."
"Not so fast, let me call the desk. We'll get this straightened out. " He suppressed a grin as she turned pale. He could feel the pulse in her wrist speed up beneath his fingers.
"No, that's fine; I'd rather not embarrass myself further."
"Oh but I insist! Or, if you'd rather, I can just call the police."
"Um, no, that's okay."
"Then we'll just have a seat and talk this out like civilized people. Who are you and what are you doing in my rooms?"
"I'm really Jennifer, and I was really trying to surprise and old school friend and I really got the wrong room."
"Right." He yanked her closer, smiling into her frightened eyes. He leaned closer; she twisted in his grip, trying to peel away before he could kiss her. He leaned in and kissed her ear instead, whispering "Did you know you have a rather large bankroll between your lovely breasts? I wonder if you are capable of making change?"
Her face flamed as she realized he thought he was a prostitute. She started to struggle in earnest, kicking at his shins while he broke out laughing.
"You sleazy jerk! I'm not a callgirl!"
"Then what are you?" he was still laughing. "A thief?" She froze, her demeanor giving her game away. "I see. And a very good one, too, it seems."
"Look you got me; I'm a cat burglar. But I didn't take anything from you. What do you say we call it even and you let me go."
"I don't think so." He said, as he twisted her arm up behind her back and frog-marched her back to the bed.
"Please let me go." She begged. She tried to squeeze out a few tears and look sad and pathetic at him.
"No. You would have robbed me if I hadn't interrupted you and if I were fool enough to leave anything laying about." He shoved her onto the bed. She rolled as she landed, scrambling towards the far side of the bed. He simply grabbed and ankle and yanked her back. "I think we can avoid a visit with the police."
"How?" she asked mutinously; really getting nervous now. "What do you want from me?"
"I want," he said with a really evil grin. "To show you the error of your ways."
"How?" she demanded, with real tears this time, as she realized she was in over her head. He laughed heartlessly.
"Don’t start crying yet, m'dear. I've given you nothing to cry about yet." His voice, deeper and dreamier now, made her shiver. "One night, dear. One night of your time and you go free. Or I can call the authorities."
"What do I have to do?"
"Whatever I ask."
"And if I change my mind?"
"You won't. If you back out before I'm done; it's jail time for you." He reached out and traced her a tear track down her cheek with one gentle finger.
"I, I'll try."
"Very good, dear. Now, hand me the money."
"Hey! You said just one night. You didn't say anything about the money."
"Consider it a surety. You'll get it back when you're done."
"Alright." She sighed. She reached between her breasts and handed him the money. She pulled her right knee to her chest and pulled another out of her boot. She repeated the action on the other side.
"Wow! I'm in the wrong line of work! He joked. "Now go get me a drink. I prefer the red wine."
As she slipped out to the front room he pulled out a small suitcase she hadn't found. He rummaged about a bit, then pulled out a few things he thought he might need. In short order, a flogger, a cane, an old-fashioned hairbrush and a bottle of lube rested on the bedside table. She returned, handing him a glass of wine. Her wide eyes took in the objects on the table and she started to protest. He said nothing, just reached for the phone.
"Please don't." She said softly, giving him a panicked look.
He lounged back on the bed, looking her over. She shivered, blushing and paling in turns. He admired the way her soft black clothing molded to her curves. She ran a hand through her ruffled hair, fidgeting nervously.
"Get undressed. Slowly. Make it look good." His voice was soft and almost kind, but with a menacing bit of steel behind it.
She bit her lip and bowed her head, running her hands down her torso to the hem of her turtleneck. She raised it slowly, baring her torso and black bra, further mussing her hair as she pulled it off and let it drop behind her. She turned sideways to him, resting her foot on the chair. Her hair covered her hot cheeks as she unzipped her ankle length suede boot. She slowly peeled it off, taking the sock too. The other side was harder; the zipper was stuck. Soon it was abandoned too, lying forlornly next to its mate.
She faced him again, shaking her hair back from her eyes. Her shaking hands went to her zipper, working it down slowly. He stopped her as she started to peel the tight denim down.
"Turn around."
She turned her back to him, feeling like a mouse under the gimlet eye of an owl, knowing she was on the menu, so to speak. The denim slid down her legs as she bent over to pull him off. Her face flamed again as she realized her backside was raised to him. She kicked the jeans away as she turned to face him. He beckoned her closer, smiling as she tripped over a shadow on the rug.
He licked his lips and smiled as he reached up to release the front clasp on her bra. Slowly, he pulled it open, baring her small breasts. Reflexively, she reached up to cover them. He gave one nipple a pinch and she dropped her hands, muttering an apology. He gave her another pinch.
"That's 'I'm sorry, Sir.' "
"Okay" she whispered, earning a small slap across one breast. "Yes; Sir. I mean, I'm sorry Sir." She amended as a tear slipped down her cheek.
His large hands slid the straps off her shoulders, and tossed the garment away. He trailed his fingertips down her hips to her panties, pulling them off. He smiled at the wet spot on the crotch. It appeared she was as turned on just as much as she was frightened. He said nothing about it for now. He grinned her racing stripe. He gave the tuft a hair a tweak and smiled at her.
"Now then. First things first. Before the fun begins, we have to have the punishment. "
"Punishment?" Her voice was squeaky with nerves or arousal.
"Punishment.." He confirmed. "You did try to rob me, you know. Now, face down, on my knees." She hesitated. "I said, face down on my lap, NOW."
Reflexively, she backed away, her hands covering her backside. "I don't think this is such a good idea."
"Well, we could still call the cops. Of course, you would have a problem passing yourself off as 'only' a thief. I believe this is called pandering. Now come here."
She crept closer. He took her by the hand and guided her over his lap. She was short enough that her toes barely grazed the floor. She reached down on the other side to steady herself. She was already shaking as he rested his hand on the small over her back. She jumped as the other came down on her backside, not as a blow, but a gentle caress. She felt his member stirring beneath her belly as he ran his fingers over her curves. Shivers ran up her spine as his fingers trailed between her legs, making her squirm as he felt the wetness forming there. She was starting to relax, so the first blow came as a surprise.
He rained them down hard, spreading them more or less evenly around her cheeks. She wasn't screaming yet, merely starting to sob under her breath. She could feel her cheeks reddening and stinging. She tried to hold still, but as her cheeks reddened and throbbed she found herself moving under his hand. She wasn’t sure if she was trying to evade the blows, or raising her body to him.
Pretty soon her backside was glowing, and he began to strike harder. She was starting to whimper as he really got into it and she realized he was just warming up! Finally! He paused for a moment to admire his work. Jenn thought he was done and started to lift off his lap; he laughed and pressed her back down.
She felt something cool and hard running over her fiery cheeks; leaving goosebumps in its wake. It left her skin and she tried to turn to see what it was. He wouldn't let her up to see it, but she caught a glimpse of it in the mirror as he pressed her head back down. The sight of the wooden hairbrush in his upraised hand made her really wish she'd stopped at Room 316. It landed with a crack that made her yelp. She covered her mouth with her hands to muffle her cries as the welts rose across her cheeks. She was crying in earnest when he finally stopped and tossed the brush away. This time, she didn't make the mistake of trying to move. One hand was still caressing her bruised backside, teasing the welts as his erection pressed into her belly.
"On you knees, pet." He said softly guiding her to kneel between his spread legs. He ran a damp fingertip over her lips. She licked it gently, tasting herself. She huddled on the floor in front of him, still sniffling a bit as he stood to undress.. She wiped her eyes with the back of one hand, not looking at him. She didn't want to see him, didn't want to be attracted to his powerful build and big hands and dark eyes. He was large and uncut, fully aroused. He loomed over here, absently stroking himself.
"Do you like oral?" He asked softly. She nodded, not quite trusting her voice. "Show me." He said, again offering his fingers, now wet with his essence. Again she flickered her tongue over them, tasting him salty sweet against her tongue. She sucked one long finger inside, nibbling softly as it passed her lips. He smiled and pulled away.
He ran his left hand through her hair, using the other to guide his head to her lips. He ran the head over them as he cupped the back of her head in his hand. He chuckled as she tried to catch it in her mouth, pulling it away.
"Ask me nicely." He said softly, twisting his fingers in her hair.
"Please let me have it, Sir." She said softly.
"Have what, m'dear. Be specific."
"Please let me have your cock, Sir." She flushed at the coarse language.
He smiled down at her bowed head; placed the head at her lips and thrust inside. Jenn suckled frantically at it, swirling her tongue around the shaft as he moved. He had both hands in her hair now, holding her still as he fucked her slowly. She had never been with an uncircumcised guy, but she was pleasantly surprised by the texture of his foreskin, velvety soft against her lips and tongue. Gradually she relaxed and trailed her fingers between her legs. She sighed against him as she gently teased her soft folds, her throbbing clit. She moaned against his shaft as he pressed deeper, holding her down until she gasped for breath around his shaft. He’d back off for an instant, letting her breathe. She took him as deep as she could on the downstroke, desperately trying to bring him off. He knew exactly what she was trying to do and pulled out, leaving her kneeling in the middle of the floor, breathing hard as he walked away.
She waited, unsure of what he wanted from her. He stood beside the bed, playing with the cane. She shook her head and whimpered as he waved her closer. He smiled again, coldly, telling her silently that she really didn't want to make him come to her. It galled her to admit that her trembling legs wouldn't hold her as she crawled to him. She pulled herself to her feet in front of him, steadying herself against the mattress. He ran the tip of the cane from breastbone to hip, tickling her. Gooseflesh broke out on her arms and legs. He used the tip to tease her nipples, smiling again as she shivered.
"Get on the bed, on your hands and knees."
"Please Sir, don't do it."
"Get on the bed, on your hands and knees." Firmly this time, with an insistent prod of the tip between her legs.
"Please don't do this to me; I can't bear it." She wrapped her arms defensively over her middle and looked at him miserably.
He raised the cane over her head, bringing it down with a whoosh. She cried out as it stopped less than an inch from her breast. She took a deep breath and looked at him with wide eyes. The cane fell unheeded to the floor as he yanked her closer, kissing her with punishing force. He bit her lip, making her throw her arms around him as her knees buckled. He pushed her back onto the bed, down on her hands and knees. Her reddened butt was high in the air as he pressed her legs further apart. His shaft was between her legs, the tip rubbing against her silken folds. She pressed back against him whispering "Please".
"Please what?" He teased, slipping a long finger in her tight sheath.
"Please just do it!" She moaned.
"Do what? Be specific, m'dear. Ask me to fuck you." He said as he yanked her head back by a fistful of hair, so he could see her blush. The idea that the language made her uncomfortable tickled him.
"Please fuck me, Sir." She gasped, predictably flushing.
He let her hair go, grabbed her hips and plunged inside, eliciting a yelp. He took her hard, making her fight to keep her balance beneath him. Her hands were fisted in the blankets, knees aching beneath the onslaught. Her flaming backside and aching pussy burned beneath him. He began slapping her abused cheeks as he pulled back, making her spasm around him. She hated this, hated him for making her feel so good as he punished her body. Her pussy started to spasm around him as her orgasm approached. He froze, making her cry with frustration. She looked back over her shoulder at him.
"Please don't stop, Sir." Hating the longing and the lust in her voice.
"Now you develop manners? Someone should have disciplined you long ago."
"I'm sorry, Sir, really very sorry."
"Sorry for being a thief? Or sorry you got caught being a thief."
She tried to calm the thoughts swirling about her brain but she couldn’t concentrate. "I don't know Sir.."
"Well, you're more honest now than you were an hour ago. I think I'll let you have a reward."
He turned gentle, almost tender as he moved. The contrast made her head spin. How could he be so hard, so cruel one moment and like this the next? One hand gently stroked her cheeks, the other slipped beneath her, teasing her aching bud. She sighed sweetly, not noticing his thumb stroking her rosebud. He licked his finger as she started to tighten on him, knowing she was about come. He pressed it inside making her gasp. He worked it deeper, opening her slowly. It was buried nearly to the knuckle but she was only peripherally aware of it. She was concentrating on trying to bring him off, too. She was bearing down on him, squeezing tightly as she started to come with a yell, tossing her head as she rode him. He grinned as she came, laughed as her body twisted on his cock. He waited calmly for her to settle down, using the hand below her to guide her trembling body to the bed. She winced she rolled over and her backside brushed the bed. She turned to her side, curled protectively into a ball and watched him warily. He was still erect and still wearing that dangerous little smile. He seated himself next to her, watching her catch her breath.
"Are you alright?" he asked in a voice of mock concern.
"Yes," she mumbled "but I need a drink please."
"There's bottled water in the fridge in the front room, or a tumbler in the bathroom."
She picked up his glass on the way out to the front room. She returned with a bottle of Evian and another glass of wine. She handed it to him silently, then took a sip of her water.
"Trying to get me drunk enough to escape, or trying to be sweet so I'll go easier you?"
"Neither one. I was trying to be nice. I'm not completely horrible, y'know."
"No, I don't know. But you can keep trying to prove it if you want to. Don't sit down." He added as she tried to take a seat, a healthy distance away from him. "Over to the sofa."
She went quietly with a downcast face and bowed head.. She placed her drink on the table and waited for instructions.
"Kneel on the sofa, facing the back, knees apart. I want your arms on the back of the couch and your head down on your arms."
She followed his instructions to the letter, gratefully hiding her face. He stood behind her for a moment admiring her bruised cheeks. She turned to see what he was doing when she heard the top pop off of the bottle he carried. He gave her a crack across the backside reminding her to keep her head down. She obeyed instantly, then flinched as the lube dribbled down the crack of her backside.
"Please don’t Sir, I’ve never done it that way before." She moaned.
"Hush, or I’m tossing the lube." She risked his anger to look back at him, eyes wide and panicked.
"I’m serious! No-ones’s ever done that to me before. Please don’t."
He gave her a steely look. "I gave in on the cane. I can get it again. Your choice, m’dear."
"Neither one, please. Is there anything else I can do?"
"I fuck it or I cane it. Make up your mind, quickly." She bit her lip, tears streaming again.
"Please call the police."
"No. You’ve gone too far. This is the last thing I’ll ask of you. Now choose." She shook her head. "I can draw blood either way, m’dear."
"This then." She muttered, nodding at the lube.
"That’s not how you ask."
"Please fuck me, Sir." She muttered, hating the words, hating the begging.
"Where?" He was relentless, enjoying her tears and discomfort.
"Please fuck my ass, Sir." She whispered.
"Turn around."
She resumed her position, crying softly with fear as he oiled himself. She shuddered as he parted her cheeks and pressed his head against her rosebud. He spoke softly, telling her to relax as he pressed inside.
"I’m trying!" She gasped.
"Not hard enough!"
He reached beneath her, toying with her clit. She hissed in frustration, as the pain and the pleasure made her head swirl. She relaxed slightly as he slipped inside. He paused for a moment then pushed deeper, enjoying her cries. She cried harder as he opened her back passage, more from embarrassment than pain. His fucking hurt a bit, but felt great, too. It galled her that she was enjoying this, and angry with the man who was making her feel so good. She’d never felt so full, even when the same man was taking her normally. He withdrew a bit then pressed deeper, working all the way in. She raised her head and was pushing back against him, earning another slap as he drew back. The pain made her spasm around him, so he did it again, enjoying her response.
"I. Said. Keep. Your. Head. Down. " He punctuated each word with a slap, sliding the other hand up her spine to the back of her neck and pushing her down.
"Yes Sir." she wept as she came again, hating him for the orgasm.
He sensed she was pretty much at the end of her rope.. He took advantage of her orgasm, plunging deeply inside. He still had one hand on her neck; the other was pulling her hips back to meet him. She was burning, inside and out. She closed her eyes tight against the pain as he took his pleasure. Her cheeks felt scalded from her tears. He came with a shout, overfilling her backside. He withdrew slowly, his benediction stinging her chafed cheeks. He pulled her head up by the hair, giving her a hard kiss before striding into the bathroom.
She took a long slow drink. He was moving around the bath, taking a shower from the sound of it. The a/c chilled her aching body. She gave the throw a pull off the back of the sofa, covering herself. She wanted desperately to leave; but she wasn’t sure if he was done with her yet. She tried to think back to see if she’d le enough personal info slip so that he could track her down. She rubbed her tender backside as she waited.
She’d nearly dozed off by the time the shower stopped. She woke with a jerk at the sudden silence. The water started again, and she relaxed slightly. A few minutes later he stood over her, in a black terry robe. She warily opened her eyes.
"I’ve run you a bath if you want it. You can leave now if you want, or go wash up."
"Thank you. I’d like the bath, if I can go alone."
"No problem, I’ve had my fun for the night."
She stumbled into the bathroom, sinking gratefully into the sparkling bubbles. The scent of sandalwood and cinnamon engulfed her. She had a short soak, then a quick scrub. She peaked out into the main room; he was stretched out on the bed, watching CNN. She crept out to retrieve her clothes. He clicked off the television as he reached for a bottle of lotion. She backed away as he walked up to her.
"Turn around."
"You said you were done with me." She protested softly, retreating ‘til she was against the wall.
"I am. This is for you. It’s vitamin D and E lotion, with aloe. It’s to bring down the bruises and soothe the skin. You can take it with you when you go."
His hands were gentle, smoothing the thick cream over her bruised and welted flesh. He helped her dress and get herself together, chuckling at the look on her face as he used the same brush to smooth her curls. He walked her to the door, handing her the money. She took it with flaming cheeks and sudden sense of shame at how she earned her living.
A week later, she surveyed the fading bruises in the mirror and contemplated the note she’d found in the roll of bills.
"Thank you for a lovely evening. Hopefully, I’ve made an honest woman out of you. If you need further need of correction, please feel free to look me up around Christmas time. I always stay at the Hotel Caribe."
