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A Prostitute Discovers her Standing - Day 1

Ellen encounters Jack.

Spankmasters
May 19, 2024
17 min read
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A Whore Finds her Place - Day 01
A Whore Finds her Place - Day 01

A Prostitute Discovers her Standing - Day 1

"ding You've found a match with Jack," Ellen's phone blared to life. Ellen felt a mix of anticipation and nerves as this was the 15th match she'd received in the last few days without any luck. She quickly typed out a message and soon found herself at Jack's doorstep.

Ellen Jackson, a 37-year-old woman with an impressive resume that included undergraduate studies, law school, passing the bar, earning a PhD, an MD, and becoming a neurosurgeon, was on a mission. She had less than a week to get married and have a baby before her graduate medical education began. It was February, and she calculated that she only had six days to conceive in order to give birth and resume her education on time.

Ellen's appearance was plain and practical, with a narrow frame, short stature, and minimal interest in personal grooming. Her CV was impressive yet her interview skills were not, as she was a strict observer of abstinence until marriage. As a deeply religious Christian, Ellen made a promise to herself and God to wait until marriage before engaging in sexual acts. She managed to keep that promise for over 30 years.

Jack Florence, on the other hand, was a frat boy during his college years, majoring in economics and landing a job on Wall Street after graduation. Despite never working out, he somehow maintained a six-pack. This date was going to be a piece of cake for Jack.

Jack and his colleagues had a competition going to see who could corruptions the most innocent woman. They set up fake dating profiles on Christian Mingle and Onlyfish, presenting themselves as devout, wholesome men.

Bob was leading the competition, having pursued and manipulated an 18-year-old youth group leader with long blonde hair and large breasts for seven months before convincing her that their age difference was divine, and that giving oral sex wasn't a sin. And that since anal sex wasn't mentioned in the Bible, it wasn't a sin either. By the time Bob was done with her, she was a stripper who gave handjobs for $10 in the champagne room.

When Jack saw Ellen's profile, he thought it was his chance to have the ultimate triumph. He showed his friends her profile and the comments began immediately. "What the hell, she's a 37-year-old virgin?" and "Damn, look at all those degrees, and she's got a cross in her profile photo?" and "Holy shit, give me all your money."

Day 1

Jack made all the necessary preparations, putting Bibles and religious books and magazines around his apartment, hanging crosses on the walls, and even hanging a cross on the outside of his door. He finished off the look by adding some decorative pillows with scripture verses stitched onto them that he'd picked up from a thrift store.

As Ellen rang the doorbell, Jack was putting the finishing touches on the pillows.

Ellen stood outside his apartment, dressed conservatively in a button-up shirt with a brooch, a knit sweater, and a long skirt with a floral pattern. She wore thick tights with a floral pattern sewn in, and although she didn't show much skin, she had applied some blush to her cheeks and nose, mascara to her lashes, and too much pink eyeshadow.

Ellen had only worn lipstick a few times in her life, but it was hard to tell based on her appearance that night. She had worn make-up before, but you'd never know it from her severe application of pink eyeshadow.

Jack's smile was warm when he opened the door and saw her. He offered her a single daisy and welcomed her inside.

As Ellen entered, she noticed the worship music playing on the stereo. She placed the daisy on the table and removed her shoes. Jack moved her closer to the sofa and sat near her, their knees pointed in toward each other. Jack asked her some basic questions, pretending to be genuinely interested.

"Were you always Christian, or did you convert?" Ellen inquired, wanting to test Jack's devotion.

"I was born into it, you?" Jack countered, keeping the conversation flowing.

"I have never missed a Sunday."

"How wonderful" Jack beamed, pleased by her answer. Jack then excused himself to get them some water and to adjust the thermostat to 85.

"I was baptized at the Holy Sacrament, wasn't I?" Ellen grinned a little as she proudly reminded herself, then quickly focused on her hands.

"Darn it," she thought inwardly, "why do I have to be so arrogant now? Ellen, calm down and stop bragging." She felt bad for her outburst.

Jack, sensing the change, began using it to his advantage.

"You were really showing off, Ellen. Now you're going to have to pray for forgiveness." Jack led her to the apartment's entrance and helped her kneel on the stone floor of the foyer.

Jack turned the music off and prepared dinner. When he was done, he went back to where Ellen was kneeling to check on her.

"Your eyes are so pretty, Ellen," Jack commented as he helped her stand and held her back.

Jack led her to the dining table to eat. Ellen was bewildered. Was she supposed to serve him? She hesitated a bit before beginning to serve the food. Jack smiled slightly and gently placed his hand on the small of her back.

His hand was on the back of her thigh and his firm grasp pressed down on her skin. A deep breath escaped Ellen as she sank back into her chair.

Ellen felt warmth in her abdomen. She realized Jack was a good Christian man and a potential husband. Fast forward: she had six days to get him to propose, marry, and impregnate her, in that order.

As she thought about it, Ellen stared at Jack's hand on her leg. It was strong and powerful; his fingers were halfway around her leg, and his thumb almost reached his fingertips. Ellen had never been touched like this before.

The sensation was both exciting and uncomfortable to her. However, she also felt a sense of comfort and security in his strong grasp. She decided she could get used to it. His hand wasn't hurting her enough to cause pain or leave a mark.

Jack heaved, breathing heavily through his nose, his teeth clenched tightly. "Please, Ellen. Let me touch you." He let go and recited a short prayer. He then served both plates. He waited for Ellen to grab her fork, then gripped her wrist firmly.

"Greed won't be tolerated, Ellen. Rise." Jack tightened his grip but guided her by the wrist back to the foyer. He held her wrist as she knelt and released it when Ellen folded her hands in her lap and lowered her chin to her chest.

After completing his dinner, Jack returned and gently pulled Ellen up by the wrist. He guided her back to the table as he did before. "Shall we clean up, or should I just end this?"

Ellen spiraled into panic. She desperately didn't want to let Jack go; she had a plan. In the following weeks, she would conceive, give birth, and breastfeed before continuing her studies. She wasn't about to return to online dating and the rejection.

"I'll clean up, please sit on the couch and relax. After I'm finished, we'll carry on our conversation."

Jack paused before responding.

"You will call me sir."

"Yes, sir, please sit while I clean up the mess." Jack nodded, and Ellen admired how his knowledge of scripture had impressed her.

Ellen, herself, had abstained from alcohol her entire life. But she'd never encountered that verse in that context before. Her eyes widened as she supposedly realized the verse's meaning.

Once she'd finished cleaning up, she re-joined Jack on the couch, spotting a glass of scotch on the table in front of her.

"Is that... is that alcohol?"

"Sir?" Jack repeated.

"Um... is that alcohol, sir?"

Jack sneered at her insolence. "It is. Ecclesiastes 9:7, one should enjoy alcohol with a cheerful heart. Finish it."

"Yes, sir." Ellen felt surprised by his scriptural knowledge, but she was even more shocked by his drinking.

Ellen had been teetotal her whole life up until this point, but the newfound warming sensation in her body enchanted her.

After her first sip, Ellen's emotions mixed with the warm liquid, bringing both astonishment and determination. She was overwhelmed by the taste of the amber liquid, but she drank it all the same.

"What do you think, Ellen?"

"Interesting, sir," she stammered, trying to recover from her shock.

"Sir!" Jack reminded her firmly.

Ellen's face flushed. She was insulting him with her impoliteness. She lowered her eyes in remorse, unable to meet his gaze.

"It's interesting, sir," she repeated with greater respect.

"Excellent, Ellen. You're learning."

Ellen watched as Jack took her wrist softly in his hand. It was evident that he could have held both her wrists with ease, but he chose not to. This pleased her. Her gaze traced from his hand to his face, where he was smiling. He wasn't angry.

She vowed to herself that she would make amends. The plan was still in motion.

"Ellen, I find you attractive. I think we could make a good pair together." Jack's hold on her wrist tightened a little. "As long as you are willing to adhere to God's plan."

Ellen lowered her head once more. She understood that her plan was insignificant compared to the greater goal. She apologized and went to the entrance to kneel down.

"Stop! Ellen, this won't work. It's evident that you're not learning fast enough." Jack looked down his nose at Ellen. "Your tights are too bulky, they're weakening you. Remove them, now."

Ellen stared at Jack, unsure of what to do. She could not imagine removing her tights while he was watching her.

"Sir, my privacy."

"My focus is on your piety, Ellen. Your irreverence could jeopardize this partnership more than anything else."

Ellen focused on the word "relationship." She desired a relationship. For the pregnancy, to have time to bond with her child before resuming her studies. She recognized Jack as a man who could guide her to a righteous path.

She opened her skirt to reach the waist of her tights. She wanted to maintain her modesty and pull down her tights and skirt at the same time. She reached up, grabbed onto the hem of her tights, and started pulling them down quickly.

However, once she pulled her tights down to her knees, she realized she also pulled down her underwear. She noticed that her skirt had remained in place, hanging around her waist.

"Stop!" Jack ordered. "Stand up."

"Sir, I'm..."

"Stand straight and face forward." Jack ordered.

Ellen defied every impulse in her body and slowly rose to a standing position. She was exposed from her waist to her knees. Jack could see her naked legs. Ellen felt horrified.

She had only a few days left to make this "relationship" work. He would see her, wouldn't he? And if this was a sin, it would be a temporary one. He would eventually become her husband. But there was an order in which this needed to occur.

Jack knelt behind Ellen and placed his hand on her calf. He observed the redness and bruising on her knees from her earlier prayer sessions.

He saw the underwear Ellen was wearing. Whether you called them bloomers, granny panties, or something else, they were not visually appealing. They were perfect for Ellen, consistent with the expectations he had for her.

"Kneel." Jack instructed.

"Yes, sir."

"Fix your skirt."

"Yes, sir."

Ellen adjusted her skirt, bringing it back to its original position. She caught a glimpse of Jack moving behind her. She felt his presence behind her.

Jack knelt behind Ellen, grasping her tights and her underwear together in his fist before yanking them backward. Ellen reacted by thrusting her hips forward. The undergarments were whipped from her legs, her feet settling onto the cold stone next to her knees. Jack tucked the clothes between the sofa's cushions before standing and pouring another drink.

He fantasized about Ellen sucking his cock, drinking his cum. He imagined fucking her pussy and her ass, defiling her in every way possible. His penis responded to these thoughts. He wanted her to see it.

Jack returned to the sofa, tucking Ellen's undergarments behind the cushions, and finished his drink. He then walked back to Ellen.

He extended his hand to her. She grasped it and gave a grateful smile. Ellen followed Jack to the sofa.

"Ellen, this evening is drawing to a close, but I don't want us to leave with negative feelings." Jack switched on some soothing jazz and offered her his hand. "May I dance with you?"

"Of course, sir."

He held her close, close enough for her to feel his penis, especially now that her tights were removed. He ensured she felt its stiffness as they danced.

Ellen felt the pressure of Jack's penis. Her body succumbed to impure thoughts, an opposing force to the ones she had fought so hard to keep away. The alcohol was flowing through her veins, making her quest to keep her mind pure even more challenging. She closed her eyes and submit to Jack's guidance. She found herself inexplicably fascinated by her clitoris as Jack's anatomy applied pressure to that area while they danced.

Jack stepped closer and guided Ellen into a dip. Onlookers would have been amazed at their dancing and thought nothing more of it. However, Ellen felt a heightened sensation of pressure on her clitoris. She stopped breath as Jack pressed his erection against her button.

Jack marveled at how the situation was evolving. He had her panties hidden in the couch, he was pressing all the right buttons, and she might be on the verge of her first orgasm. The repercussions would be severe.

Jack lifted Ellen back up and turned occasionally. His hard penis teased her clitoris as they moved around the living room.

Ellen's breath became shallow, quicker with each thrust. She wanted him to stop, yet didn't want the pleasure to end. She knew what she was doing was a sin, but her inhibitions were broken, and Jack was unaware of the impact his actions were having on her.

Ellen bent her knees slightly, hoping to further stimulate her clitoris. She began pressing into his groin, making sure the access remained unobstructed.

The pleasure intensified, which caused shock waves to surge throughout her brain. She couldn't remember where she was, she didn't care who she was with, only the torturous feelings coursing through her body. Every time Jack pulled her back and spun her, the fabric of her skirt rubbing against her swollen clit was exquisite. With each turn, his tough member crashed into her clitoris, rubbing it back and forth.

Ellen's breathing was sensual, heavy, and she began to murmur as the sensation consumed her body. Before she knew it, Jack was pulling her to him, allowing her to hump his pulsating erection. She had never been closer to an orgasm. Just a few more rotations, another spin, and one more stroke would be needed.

"Stop!" Jack shouted, pushing Ellen away from him. He switched off the music and tossed the remote to the ground. He snarled, staring intently into her eyes.

"Prostitute! Jezebel! Slut!"

The words burned. They continued to circle in her mind.

"Sir, I,"

"Shut up, Slut!" Jack bellowed.

He internally laughed at the predicament but had to maintain the act. He was caught up in the moment, adjusting his force before forcefully striking her face. He was aware of his strength, but unintentionally reduced the power of the blow.

Ellen missed stepping away, but she regained her equilibrium. She realized that it wasn't a full-throttle blow, and she was grateful for it. The guilt weighing heavily on her heart was enough. She would not only punish herself, but she welcomed his discipline.

Jack placed his hand under her chin, lifting her face to scrutinize the alteration. There was no mark, no sign that the blow made an impact. He noticed the tears arising in Ellen's eyes but didn't acknowledge them.

He gently led Ellen back to the entrance, then forcefully ripped her skirt off her body. Ellen's nakedness was now on display. Jack noted Ellen's extensive pubic hair, slick with her secretions in the vicinity of her clitoris, indicating how she had been straining against his full-grown cock.

Jack ventured into his office and retrieved a pen.

"Sit!" he ordered.

She obeyed, shifting her legs to her left. Glass shards drew blood on her legs. Ellen steadied her breath, imagining the pain as a small sacrifice for her family. Ellen's quivers echoed as the broken glass pierced her flesh. Ellen postured quietly, wedging her hands in her lap, and waited.

"I did not willingly accept your lewd gyrations, Ellen. You are a rapist! You raped me. Was this your goal? Were you trying to attract me?"

Ellen knew Jack's accusations were accurate. Her ultimate goal was to seduce him, to fall in love with him, and to have his seed planted within her. The guilt wracked her heart.

Jack extended his arm to touch her ankles, gripping them firmly and opening her legs to face her. Preparing his marker, he sat down between her legs. He marked the initial 'W' on her thigh while being so close that the pen's casing brushed against her clitoris.

Ellen uttered a slight moan, barely noticed by anyone. Extremely furious, Jack dug the marker into her skin while inscribing the 'H'. He drew her leg closer to his crotch, using the marker to create the 'O'. As he crafted the 'R', he extended her foot over his erection. He could identify her arousal by the scent alone. With 'E', he completed the word on her left leg.

Carefully, he got a hold of her right thigh, bending it and allowing her foot to rest back on top of his hard-on.

It demanded tremendous willpower for Ellen to not act on her urges, trying not to stimulate his dick with her toes. Intrigued by the idea, she fantasized about inserting her foot into his trousers, running her toes over him, and pressing certain buttons to reveal hidden sex toys.

Her body was aching for his touch, but she resisted the urge to gratify him. She considered herself a slut, having fought against her temptations, always wanting to satisfy him.

The broken glass played an essential role in her salvation, hostile to her but a refuge for her as well. The pain provided a comfort, keeping her focused.

Jack stopped to examine the S he'd drawn and rubbed his marker along her pulsating clitoris. He moved to construct the L following the 'S'. His fingers rubbed her lower body, spreading her legs apart.

"Get up, you filthy whore, on your knees!" alerting her to change positions, Jack helped her stand up.

"Yes, Sir." she responded obediently, sweat accumulating on her body.

Jack removed his shoes, causing some crunching noises, before removing her sweater. He smoothed it out on the debris and abandoned it on the floor.

Moving around her, Jack shed her shirt, demanding her full attention. Her neck felt like a desperate territory begging for his touch. To Jack, seeing Ellen now was thrilling; her body showed the epitome of temptation. To enact ultimate control, he began to unbutton her shirt.

Each button he loosened caused Ellen to stifle her breath as he gradually enacted his domination over her. Once her shirt was removed, he examined her camisole clothes and desired to push them aside to fully see her bare skin.

Ellen was warmed by the sight of his phallus, eager for any actions he performed, and asked him straight-out to remove her camisole. With self-loathing and with the words "whore" and "slut" engrained on her legs, she was convinced she deserved it.

Having been Methodical, she never realized how much she wanted him to touch her. Her clit was desperate, her mind overwhelmed by the guilt. The temperature rose, making the room seem unbearably warm.

He had posed a question to her, "Up, cum slut, on your knees." Taking his place behind her, he undressed her camisole, leaving her naked in front of him.

"Yes, sir." she responded enthusiastically. With a merciless stance, he grasped her sweater and threw it away; his shoes crunched against the scattered glass as they combined into a crazy dance of willpower and pleasure.

Jack's legs were strong as he walked towards the kitchen and grabbed a large carving knife. "You committed a sin, Ellen!" Jack shouted from the next room. "You sinned against me and against God. Your sin won't go unpunished. Do you understand me, Ellen?"

Ellen's voice was barely audible, "Yes sir."

"Ellen, do you understand me?"

Ellen tried to yell, "Sir, yes sir," but it still only came out as a whisper. Her throat was dry, her lips were beginning to crack, but the room was so hot.

"Ellen, can you hear me?" Jack was getting angrier and his steps were getting faster as he made his way back to her.

"Yes sir!" Ellen could barely squeak out the words. Her hair was sticking to her head, but she didn't dare move her arms to adjust it. Sweat was dripping from her chin onto the floor in front of her. She couldn't move any part of her body past her chin.

She could see the glint of the knife in Jack's hand. She knew her sins of the evening weren't worthy of the death penalty.

Jack carefully positioned the knife on Ellen's shoulder. He watched as the tip of the knife made an indent on her skin as he slid the sharp blade down over her collarbone. The strap of the camisole shifted as the knife went over it, and Jack moved the knife in such a way that it didn't cut through the fabric.

Ellen felt the cold steel against her skin, which felt nice in the heat. She could feel the power of the blade just inches from her face. It took everything in her power not to jump when the strap of her camisole popped up.

It only took a slight twist of Jack's wrist for the knife to slice through the strap. The front of her camisole fell forward slightly but got caught between her hardened nipple and the strap from her other shoulder.

Jack switched hands and slid the cool backside of the knife along Ellen's shoulder blades. He cut through the other strap by pulling the knife away from Ellen's body, and he could see the sweat forming around her shoulders. It was so damn hot in there.

Jack stepped back into the kitchen to put the knife away and returned with a washcloth holding something.

"Your penance for your sins will take many forms, whore. You teased me, tempted me," Jack yelled, "you'll now be tempted. You'll now be teased. You'll now be presented as you deserve."

"Yes sir." Ellen managed to stand up gracefully, each foot replacing the previous foot's position on the ground. She could feel the burn from the glass her feet were on, but she ignored any other pain that didn't remind her of her situation with Jack.

Her camisole had fallen to the floor as she stood, her hips were too narrow to keep it in place. Her nipples weren't big enough to prevent gravity from taking its course in her penance.

Jack held out the washcloth to show an ice cube. He traced each of her eyebrows with the ice, watching as the water mixed with her sweat and dried in the heat. He traced her nose, wet her lips, and used just the right amount of force to spread her bottom lip out with the ice, which quickly popped back into place.

Ellen fought to hold in her laugh at the sound, assisted by the sensation of the ice being moved behind her ear lobe, then dragged down her cheek, under her cheek bone, along her jaw, over her collarbone, on the edge of her breast, around her shoulder.

Her skin remained wet from the melting ice, along with sweat and goose bumps. The same process was repeated on the other side, and the ice cube was placed on her forehead, down her nose, over her lips, her chin, down her throat, her breastbone, her stomach. Jack's hand was pointed downward, where he could have explored if he had been with any other of his lovers. But Ellen was his conquest. He reached for a marker and began writing on her stomach, her breasts, and her cheeks. She couldn't see the writing, but she knew the words were meant as punishment.

Jack scribbled on Ellen's back, hips, and behind. He sketched arrows front and back, labeling them "Insert penis here" and scribbled one on her cheek for added measure. Other notes muttered to keep Ellen in check like "Bitch," "Cock Hungry," and "Slut" for contrast.

Jack was meticulous in avoiding her nipples during this task. He steered clear of her clit for the rest of the night. After he capped his marker, he took some time to admire his creations. Then, he slipped out to his room, returning with a ratty old DSLR camera.

Blessedly, there was enough battery and memory storage available for a few shots of his handmade art. Ellen was puzzled by the pictures but remained silent. Jack obviously intended to use them to help her find redemption.

"Prostitute, put on your skirt and shirt. It's time for you to go."

"Yes, master." Ellen lowered her gaze, grabbing her clothes.

The brooch vanished along with her underwear, tights, and sweater. Even with clothes on, the markings on her face and shins were evident. As she started to sweat in her white shirt, the black writing on her skin became obvious. "Will I see you again, master?"

Jack stole a glance at her, his countenance kind. He cupped her chin between his thumb and forefinger and brushed his lips against hers. "Of course," he beamed. "I think I'm beginning to like you."

Ellen sobbed tears of happiness as she packed up her purse and shoes. She shuffled out of the apartment without asking, leaving bloody footprints behind. The cold tile of the hallway felt refreshing. How could that apartment be so warm?

Tears welled up in Ellen's eyes as she raced towards her house at lightning speed. Could Jack ever pardon her?

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