by Nicola Diaz
The cane whistled and struck her already tender ass and Jessica jumped. “Five!” She heard the cane arcing back and whistling down again, and she tensed for the strike. “Four!” Again, the cane lifted and fell, hitting her ass with a loud crack. “Three!” Her entire body was trembling in pain and the next strike came as a surprise, “Two!” Jessica was near to tears when she heard the whistle and swish of the final strike. She clenched her hands over her head to keep from reaching to block the hardest blow yet. “One!”
“Very good, Jessica,” now his voice was a tender purr. “Let’s get you cleaned up and fed properly before we speak.”
He pulled her to stand, then led her to a large bathroom where he turned on the shower and instructed her to get in. Jessica was in shock. She’d never been through anything like that in her life. When she came out of the shower, he toweled her off gently, then stood her in front of a large, three-way mirror. “Look at those magnificent marks, Jessica.” Her ass was covered in angry red welts. Despite her fears, she was not bleeding, but there were already bright red and purple bruises showing, crossed with angry red lines.
“This is one way I will punish you for misbehavior. Make no mistake, I enjoy causing you pain, but I take no real joy in punishing you. There is a difference. I hope you will learn to take joy in submitting to pain as well.”
He wrapped her in a soft robe and took her to a large room filled with bookshelves, deep, leather couches and a large desk. “This is my study. Here is where you and I will talk when it is pleasant, but serious business. This room is not for punishment or play or pleasure. It’s for what we are about to do now.”
A servant brought in a tray of food and put it on a table near one of the couches. “Sit, eat.” He pointed at the couch. Jessica was still in a fog, but surprisingly hungry. She ate while he spoke.
“I find I have very particular tastes when it comes to women,” he said. “While it’s very easy to find women to do what I want, they often come along with strings I don’t want. I’m perfectly willing to pay for what I desire, and I’m happy to give very generously. All of my staff are very well cared for. But I’m not willing to risk my fortune, nor my reputation on a woman who is more interested in my bank account than in me, so I avoid romantic entanglements. I prefer, instead, to rely on professionals. I usually have a regular pet, but my last has recently moved on. She finished college and has entered a career. I couldn’t be happier for her.” He smiled brightly.
“Since her absence, I’ve contented myself with other women who know my habits, but I prefer to have someone regular, someone who knows me well, and who is willing to eventually live in for a period. As I said, I pay generously and the benefits are second to none. It’s been a long time since I had to train a new girl. I may be a bit impatient. This is a one-week contract, a trial, if you will. After the week is up, we see where we’re at. I may offer a longer contract. It’s up to you whether or not you take it. It will be challenging, but also rewarding. One thing you need to know, there will be no sex. I will use you, abuse you, and I will touch you and violate your body with my fingers and toys, but my pants stay on and you will not touch my cock. Are you finished? Good, then it’s time for some fun. Come along.”
He led her through the house to another heavy black door, then down a flight of stairs to a large room outfitted like a dungeon. “Normally, I don’t allow my slaves safewords,” he explained. “The fact is, I know them well enough that they don’t need it. But since you’re new to this, and to me, I will allow you this. If something is too much for you, call out ‘red’, and I will pause so we can talk. I warn you, call out falsely, and I will ignore you the next time, or worse. This is not a way to get out of something you don’t like. It’s simply a way to communicate your physical or psychological limits until I learn where yours are.”
He laid her back on a padded table and fastened her wrists into leather cuffs over her head and he ankles into cuffs that kept her legs wide apart. He buckled a leather strap around her neck so she couldn’t lift or even shake her head, and another at her waist so she couldn’t move her body. He poured warm oil over her body and smoothed it into her skin, working it into the folds of her pussy.
“Carmine did a very good job on your waxing,” he purred softly as he stroked his fingers between her lips. Jessica felt her clit swelling and her pussy getting wet as his fingers teased and stroked. He slipped a finger into her pussy and Jessica moaned. This part she knew. The sex. She was good at the sex, and she knew it. His fingers stroked her g-spot until her breathing became ragged and rough. She tried to arch into his touch, but the straps held her in place.
Suddenly, his hand withdrew and Jessica pouted. She heard him laugh, then felt a trickle of something very hot on her chest. She opened her eyes and looked at him. He was holding a glass candle full of molten wax above her and dribbling wax over her tits.
He moved down, letting the wax stream over her belly. Jessica sucked in her breath when she realized where he was going, “Oh, no, no, no, no, no… please, no…”
The wax trickled over her freshly waxed pubic bone. Then along her inner thighs. She hissed and jumped when the wax hit high up along the bikini line. Then he poured the wax directly over her clit. Jessica squealed, the heat was intense. He continued pouring wax on her until her entire pussy was covered. Jessica was breathing in short gasps.
Then he put the candle down and slapped his hand hard against her wax-covered pussy. The impact was blunted with the layer of wax and Jessica moaned in pleasure as his fingers began massaging the still warm wax against her skin. He rubbed, then slapped again, and rubbed some more. He poured more oil onto his hands and massaged her through the still warm, malleable wax, his fingers pressing against her pussy, stroking her clit through the layers of wax. She was so close to orgasm, then he stopped again.
“Jessica,” his voice was a soft purr, “I know you’re very excited and you want to cum, but that is not allowed. You will only have an orgasm when I say you can. Until then, you will hold off. If you find you are getting too close, you will tell me so I can stop before you do. Is that clear?”
“Yes, sir,” she whispered, gritting her teeth as he continued to stroke his hands over her body. “Very good,” he whispered in her ear. “You had a very hard punishment this morning, but you’re not quite ready for service yet. No…” his hands dug into the wax, squeezing her muscles painfully. “Your mind isn’t yet mine.”
His hand flashed out and slapped her left cheek. Hard enough to sting and make her eyes water. Jessica let out a whimper. “Jessica,” he leaned close to her, “what are you?”
She didn’t know what to answer. She shook her head as much as the bonds would allow and started to tell him she didn’t know. His hand flashed again, leaving a red imprint on her right cheek. “What are you Jessica? You read the book. You know what I’m looking for.”
She struggled to recall the book, but her mind went completely blank. His hand struck her left cheek again, harder. She began to cry in earnest. “You have a job, Jessica. What is that?”
“I’m a call girl,” she choked out between sobs. He slapped her right cheek again. “Try again, Jessica. What are you?”
“I’m a whore,” she offered and he smiled. “Yes, you’re a dirty slut and a whore. Remember that. You are a slut, you’re a plaything. You’ve been bought and paid for and I can do with you whatever I want, whether you like it or not. And don’t think I don’t see that look on your face. You’re angry and you’re frightened. That’s fine. You’ll get over them both, but for now, I like it. It gives me something to break.”
He picked up a large knife and slowly began scraping the wax off her body. When he got to her pussy, he used his fingers to pull the wax off her lips and clit. When all the wax was removed, he led her to the shower again. “I’ll be out for the rest of the day, I won’t require you again until breakfast tomorrow. See that you’re on time. And I suggest you have some studying to do.” He walked out and left he
r clutching the robe.
Jessica spent the afternoon rereading the leather book, making mental notes about as much as she could. She seriously considered finding a phone and calling the agency, or even the police. This guy terrified her. But she was also curious. She’d never felt so alive as she had when he had been massaging the wax into her. He was good looking, there was no denying that. The control he exhibited was exciting. Jessica had never really been into the whole kink thing, but something about him, about the way he acted, made her hot. And oh god, the way his fingers moved in her pussy. She reached down and found she was wet. The book said she was not allowed to masturbate, but how would he know?
She was in a quiet room, all alone, studying. No one was around. Jessica stroked herself slowly, remembering the feel of his fingers inside her, stroking her g-spot and her clit. Even the feel of the hot wax as it poured over her clit. The feel of his hands slapping against her pussy, the hot wax pressing into her skin. It was pleasure and pain all rolled into one, it was an exciting combination. Her fingers sped up, pinching her clit until she came fast and hard, clamping her mouth shut to make no sound.
The next morning, she was ready, in a light dress as instructed and kneeling next to his chair before he entered the breakfast room. She rose as he commanded and took his plates from the server, arranged the dishes and food in front of him, poured his juice and coffee and did everything exactly as described in the book. When it was all done, he didn’t even look down, he caught her eye and smiled, “Well done, you’ve been studying. Please, sit,” he gestured to the chair next to him. A servant brought a plate of food for her. They ate and discussed the morning news. Jessica found he was intelligent, articulate, and a very pleasant conversationalist.
As the dishes were being cleared away, he startled her with a question. “Did you masturbate yesterday, Jessica?” She looked at him sharply. Did someone see her? Were there cameras in the house? She considered lying, but decided the punishment would be worse if she lied and then he found out. Instead she nodded, “Just once, yes, sir.”
“Mmhmm,” he murmured. He grabbed her wrist and pulled her out of the chair and over his lap. He pulled her arm behind her back, and captured her other wrist as well, holding both hands firmly just above her waist. Then he pushed her skirt up over her hips, exposing her ass. “No panties, at least you are following some of the rules,” he chuckled.
His hand stroked her ass cheeks slowly, then without warning, he slapped her left cheek, then her right. The sounds were like gunshots and Jessica jumped at the surprising sting. He delivered two more swats, harder than the last. Then he struck lower, right where her ass met her thighs, several stinging slaps in a row. He kept going, alternating between smacking the round globes of her ass and the little crease just under her ass. The slaps were hard, stinging and deep.
Jessica’s ass was on fire. She wriggled in his lap, trying to get free, but his grip was like a vice. The more she struggled, the harder he slapped. “Jessica, the rules are very clear,” he spoke as he continued slapping her ass rhythmically. “You are not to orgasm without my permission. And I did not give you permission yesterday. Not at all.” He punctuated each word of the last with a hard smack. “You’ve been a naughty girl, so I’m going to treat you as a naughty girl should be treated.”
He continued slapping her ass, moving his hand around until her entire ass was bright red and glowing. Jessica felt tears stinging her eyes, but she also felt her pussy getting warm and wet. He was slapping the inside of her ass cheeks, right where the thighs met, aiming for dead center every time. Jessica could feel the impact all the way to her clit. Each strike made her tremble a little.
He slipped his hand between her legs and his fingers slid into her wet pussy. “Naughty girl,” he laughed and flicked her clit hard with his fingers. He shoved until he had three fingers, then four in her pussy and Jessica felt stuffed full. When she tried to push back against him, he suddenly withdrew and smacked her ass again. The tears spilled over and Jessica started to cry. Still he didn’t stop. He kept slapping her ass, harder and harder, until she was actually sobbing. Then he stopped.
He turned her in his lap and wrapped his arms around her and held her until she stopped crying. He took her face in his hands and kissed her nose, then slowly laid her back on the dining table. The wood was cold against her hot ass. He spread her legs and placed her feet on the arms of his chair. His fingers stroked her pussy, “Jessica, you got so wet while I was doing that. You liked getting spanked, didn’t you?”
She mumbled something, she wasn’t even sure what and he just chuckled. His fingers stroked outside her pussy, coming right up to but not quite touching her clit. He kept going until she was trembling. His thumb flicked her clit lightly.
“Do not cum without permission.” He growled at her. His fingers reached inside for her g-spot. Jessica jumped and bit her lips to keep from crying out. His fingers were expert, stroking, pushing, curling into her, touching her most sensitive spots. His thumb continued to circle her clit and he reminded her not to cum. When she got close, he would pull his thumb off her clit, or slow down the thrusts. When he thrust all four fingers into her and ground his thumb into her clit, it was almost too much.
“Please, oh please! May I cum, sir? Please!” It was almost a scream. Jessica was begging. She couldn’t take any more without cumming. He pulled his hands away. “No, not yet. Go get cleaned up. I’ve got meetings today and you’ll accompany me to lunch. An outfit has already been chosen for you.”
Jessica’s body was screaming in desire, but she didn’t dare masturbate in the shower. Somehow, he’d know. All through lunch, he teased her, stroking her ear, whispering dirty things to her, even sliding his hand up her skirt at the table. In the cab ride back to his office, he slid his hand up until his fingers brushed her wet pussy. “Do not cum, Jessica,” he whispered in her ear as he fingered her clit. He spread her legs wide apart and finger fucked her pussy until she was shaking in desire, then he stopped and pulled her skirt back down over her thighs and shot her a wicked grin. “No cumming without permission.”
He kept it up for two more days, teasing her, keeping her on the edge of arousal. He would stop and play with her nipples, or stroke her ass until she started wiggling against him, then he would stop. She tried not responding, but he just got more aggressive. Instead of tweaking her nipple, he would finger her clit, and no matter how hard she tried, she couldn’t sit still when he did that.
For two days, Jessica did everything right. He didn’t have to punish her, but still there was the hot wax, which she actually enjoyed. She loved the heat, and the feel of the oil on her skin. But she really loved the sensation of the knife scraping the wax from her oiled body. Sometimes he spanked her for fun, that was very different than the punishment spankings. Punishment spankings were stingy and hard. The spankings for fun were sensual, they still hurt, but he stroked her ass and her pussy between smacks.
She usually had to hold back to keep from cumming when he did that.
On the third day of teasing, he led her to the dungeon room after breakfast as usual. This time, he striped her naked and took her to a sturdy X-shaped cross and cuffed her hands and feet to the beams. “Jessica,” he spoke softly, “what I’m about to do is going to cause you pain. It’s not a punishment, you’ve been very good. And if you take this well, you will be rewarded after. I enjoy doing this, and because it’s not punishment, I’ll start slowly and work my way up. You may cry, or scream, or be as loud as you’d like. If you make it through everything I do without asking me to stop, I will lay you on that table over there and make you cum over and over again. If you need me to stop, that’s OK, but there will be no orgasms then. Understood?”
She nodded at him, wondering what he had in mind. He slipped a blindfold over her eyes, then was gone for a few minutes. Jessica strained to hear, but could only tell that he was moving around the room. Then she heard a soft swishing sound, then the brush of something against her back. It wa
s soft and gentle at first, then got a little harder. When it whisked off her skin and the room was filled with a loud crack, Jessica knew what it was. He had a whip.
The tail laid across her back again, each time a little harder. Her skin was turning pink, but there were no welts. Jessica marveled at his obvious skill and control and soon relaxed into the sensations. Then the first hard strike hit, leaving a welt across her shoulders. Then another just above her ass. Jessica jumped, but he went back to the soft brushing. He alternated between soft strokes and hard strikes, criss-crossing Jessica’s back and ass with red, raised welts from the whip.
He let the whip wrap around one thigh, the end striking dangerously close to her pussy. Then he laid a deep welt along the bottom of her ass cheek. Another between her shoulder blades and another on the other ass cheek. Jessica was squealing in pain each time the whip cracked on her skin, but she gritted her teeth and dealt with it. She wanted to cum, though she wasn’t sure she’d be able to with all the pain.
He kept going until her entire back and ass were covered in red welts. He cracked the whip loudly a few times, making her jump. Then the whip lashed out and hit her right shoulder hard enough to draw blood in a tiny spot. Jessica let out a short scream and braced herself for more, but it didn’t come. Instead, his arm wrapped around her body and he unhooked her cuffs. He scooped her into his arms and carried her to the table.