Hilary Duff

A sleek black Mercedes E-Class wound its way through the Hollywood hills, making its way to the home of Mistress Zelda. The disciplinaian to the stars. Inside, the driver, a man in his mid-thirties with short, dark hair and an all -lack uniform that had been perfectly tailored to his muscular body, concentrated solely on the winding, narrow road. He paid no attention to his passenger in the back seat; his employer demanded strict professionalism from her staff at all times.

His passenger was former Disney Star, Hilary Duff. Unlike so many others of her generation of teen stars who had risen to fame in the early 2000s, Hilary had been one of the very few who hadn’t had problems with addictions or wild behavior, only the occasional controversial comment or Halloween photo. The reason for that had been simple: for nearly twenty years, she had been seeing Mistress Madeline, but she had retired and referred her to Mistress Zelda.

“This is going to work, this is going to work. Mistress Madeline would not have recommended this; Mistress Zelda otherwise,” Hilary thought as she nervously chewed on one of the earpieces of her stylish sunglasses. She gave herself another lookover. She was dressed in a snuggly fitting plain grey tank top, faded denim jeans, and a pair of dark brown leather ankle-high boots with a four-inch square heel. She felt the car slow and then turn before she heard and felt the slight rumble of the luxury car rolling slowly over cobblestones. She looked ahead out of the windshield, expecting to see an almost cookie-cutter mansion. What she saw, however, was a Gothic mansion.

The cobblestone structure towered over the well-maintained lawn in a way that was both beautiful and serene, and intensely intimidating. Everything looked to be perfectly in place. It looked like the grass had recently been mown, every dark green blade of grass cut to a uniform height, the trees and hedges were pruned neatly, and every flower in the flower gardens that lined the front of the mansion was in full bloom. She had been so distracted by studying the home, she barely realized that she was now looking at it through the rear passenger window, and the car had stopped.

The driver had exited the car, walked around the front, and opened the door. He now stood in front of her with a kind, but decidedly professional look on her face, with his left hand held out to her. “We’re here, Ms. Duff.”

“Thank you,” she replied as she took the man’s hand and slid from the back seat of the car.

“My pleasure, Ma’am,” the man said with the same smile as before. Hilary gave him a polite nod before heading up the cobblestone path to the set of large, darkly colored, wooden double doors that led into the mansion and knocked. In a matter of seconds, the right-side door opened, revealing a blonde woman who, oddly, reminded her of herself a little over a decade ago. The woman was dressed in an extremely short French Maid’s uniform.

“Welcome, Ms. Duff. Please follow me,” the woman said after Hilary stepped into the mansion’s entrance hall. The maid turned and began walking back through the entrance hall toward the long, gently curving stairs that led the the mansion’s second floor. As she followed the woman up the stairs, Hilary couldn’t help but notice how her short skirt offered a glimpse of her bare asscheeks and her white lace thong with every step she took. The rhythmic clicking of her heels called to Hilary as she followed her down the hall. The maid stopped in front of a door and knocked gently.

“Come in,” she heard another woman’s voice say from the other side of the door. The maid looked at Hilary and gave her a kind smile before opening the door. Instinctively, Hilary followed her in,

Hilary stopped behind the maid. The room they had entered was a large and ornate office dominated by a large antique desk directly in the center of the room. Behind the desk sat a brunette woman with long hair that had been styled into a tight bun. She was dressed professionally in a black suit jacket with a light blue button-down shirt beneath it. “Ms. Duff to see you, Mistress Zelda.”

“Thank you, Ava. Please go back to your duties.” Mistress Zelda said in a calm and authoritative tone.

“Yes, Mistress,” the maid said before leaving the room.

“Please, sit,” Mistress Zelda said as she motioned to the comfortable-looking black leather armchair across from her.

“Thank you for seeing me, Mistress Zelda. I’m a little surprised to see that you’re so young. No offense, but you’re quite a bit younger than I am.”

The strict dominatrix allowed herself a smile as she leaned forward slightly and placed her elbows on the desk. “No offense taken, Ms. Duff. Mistress Madeline always said I was something of a prodigy.”

“You know Mistress Madeline?” Hilary asked, her eyes widening slightly in shock.

“Of course, I had the distinct privilege of being her final apprentice.”

“Her apprentice? Really?”

“Oh yes. How do you think I learned to do what I do? Mistress Madeline taught me by having me submit to her, and by disciplining clients under her supervision for two years.”

“I… I guess I never thought about it,” Hilary said as she felt her cheeks warm with a blush of embarrassment.

“It probably isn’t something most people think of,” Mistress Zelda replied, silently enjoying the sudden flush on Hilary’s face. “I use a system much like Mistress Madeline’s, so I expect you to strip down, place your belongings in the provided bin, and present yourself for punishment. Provided you sign the contract, of course.”

“So you do the warm-up spanking, and the letter too, I assume?”

“I do. Now tell me, Hilary, what is it I can potentially help you with today?”

“Staying grounded and not giving in to pressure, I guess,” Hilary answered. “I’m still working, as you probably know, and I’m a mom of four now, which is still crazy for me to think about, and complete chaos, but I love it. I need someone to make sure I don’t step out of line.”

“I can do that for you,” Mistress Zelda said as she pulled out a contract from the top center drawer of her desk. “Just read this, it is identical to the agreement you had with Mistress Madeline, and if you find it agreeable, sign here.”

Hilary read through the short document quickly, then read it two more times to ensure she understood the agreement before signing it. “When can we start, Mistress Zelda?”

“Right now, follow me, please,” Mistress Zelda replied as she stood and left her office with Hilary close behind. She led the former Disney star down to the waiting room outside of her dungeon. “Take a seat, I’ll head into the dungeon and get ready. When I am ready for you, that light above the door will change from red to green. When it does, you are to knock on the door and wait until I tell you to enter. Once you do, well, you know the rest from there, don’t you?”

“Yes, Mistress Zelda.”

“Good girl,” Mistress Zelda said with a smile before she turned and headed for the dungeon.

Hilary sat on one of the comfy armchairs with a sigh. Time seemed to slow to a crawl as she watched the light above the door, and she began to nervously tap the heel of her boot on the floor. Finally, the light above the door changed, and she made her way to the door and knocked. “Alright, let’s see how this goes.”

“Enter,” Mistress Zelda’s voice said over the intercom. Hilary entered the dungeon and took a moment to marvel at it. Just like Mistress Madeline’s, it was dimly lit with dark wood floors and deep red walls. Every piece of bondage furniture was made of darkly colored wood and leather. A head of her sat Mistress Zelda. The strict disciplinarian had changed from her professional attire to a black leather corset, a short, red leather skirt, and knee-high, wedge-heeled, black leather boots. She gave Hilary a cold glare from her throne as she watched the former Disney star.

Hilary quickly stripped naked and placed her belongings in the large bin just inside the door. She swallowed nervously as she made her way across the dungeon, her bare feet padding against the dark, hardwood floor. She stopped in front of Mistress Zelda and lowered herself to her knees. “I’m here for my punishment, Mistress Zelda,” she said as she knelt on the floor with her legs slightly spread.

“Very good, you will have your pussy clean-shaven, just as it is now, whenever you come for discipline. I’m glad to see that Mistress Madeline taught you so well.”

“Yes, she did, Mistress Zelda,” Hilary said before taking in and slowly letting out a deep breath. “Mistress Zelda, may I please be put across your lap for my warm-up spanking?” Mistress Zelda smiled at Hilary before patting her lap. At her new disciplinarian’s unspoken command, Hilary crawled to Mistress Zelda’s right side and lay across the other woman’s lap. Her heart pounded in her chest, and she felt more nervous than she had in quite some time, placed in such a position over a much younger woman’s lap.

Mistress Zelda smirked slightly as she felt Hilary’s ass quiver ever so slightly in nervous anticipation. “Mistress Madeline forwarded your file in case you followed up on her referral,” she said as she gently rubbed Hilary’s upturned ass. “She noted that you have almost always been very well behaved and seem to respond particularly well to hard spankings and strict bondage. Is that right?”

“Yes, Mistress Zelda,” she replied, keeping her tone even.

“Then, for your first session, not only will you get a warm-up spanking, you’ll also get three of my favorite implements: the hairbrush, the leather strap, and the cane. We will finish with strict bondage before you go to write your letter. I believe you are well acquainted with all three of those implements?”

“Yes, Mistress Zelda.”

“You’ll be getting each one in a different position. After your warm-up spanking, you will get two dozen swats from the hairbrush in the legs up position, or as Mistress Madeline often called it, ‘the diaper position.’ After that, it will be the strap while you are lying on the bondage table, face down, with your hips raised. Finally, you will take the can in the lunge position. Are you ready?”

“Yes, Mistress Zelda,” she replied. Just a fraction of a second after she finished speaking, she felt Mistress Zelda’s hand raise from her tender flesh, then she felt the sting of the other woman’s palm as a resounding smack filled the air. The second swat of the dominatrix’s hand came soon after on the opposite cheek, causing Hilary to gasp and her legs to stiffen. Hilary's heart pounded in her chest as she lay across Mistress Zelda's lap, her bare bottom exposed and ****. The first two slaps stung her cheeks, and she gasped in surprise, her legs stiffening involuntarily. She closed her eyes and took a deep breath, willing herself to relax as much as possible. Mistainess Madeline's voice echoed in her head, 'The more you tense up, the more it will hurt.' Hilary took another deep breath and exhaled slowly, focusing on the cool air against her flushed skin.

"That's better," Mistress Zelda purred, her voice dripping with satisfaction. "I do like a submissive who learns quickly." She continued spanking Hilary's ass, alternating between cheeks with precise, rhythmic smacks. The sting intensified with each impact, and tears welled up in Hilary's eyes. "Just a few more, princess, and then we'll move on to the next phase."

Hilary bit her lower lip, fighting back tears as the last few spanks landed on her burning bottom. As Mistress Zelda's hand left her reddened skin, she remained still, breathing heavily. Her cheeks stung like they were on fire, but beneath the discomfort, she felt a growing sense of anticipation.

"Very good," Mistress Zelda praised. "Now, let's proceed with the hairbrush, but first, kneel." Hilary slowly slid from Mistress Zelda’s lap and knelt on the floor. She kept her gaze turned downward as the dominatrix went to one of the dark wooden cabinets on the wall and selected a simple black leather collar, and then placed it around Hilary’s neck. “Now I want you to crawl to the bondage table and lie on your back.

Hilary crawled over to the bondage table as instructed, her sore bottom throbbing with each movement. Mistress Zelda guided her into the "diaper position" and secured her wrists and ankles to the table. The cool leather of the restraints sent a chill down Hilary's spine, intensifying her arousal.

As she lay there, helpless and exposed with her legs lifted high in the air until she had folded over the cuffs that secured her ankles anchored to the bondage table above her head, she couldn't help but wonder how Mistress Madeline had found such a perfect replacement. The anticipation was excruciating as she waited for the first strike of the hairbrush.

The swat of the hairbrush came on her right ass cheek and echoed loudly in the duneon, mixing with her own cry of pain as hot tears finally began to flow down her cheeks. The feeling of her tears was therapeutic, and the harsh sting of the second swat on her left ass cheek was an almost welcome feeling. Not wanting to overwhelm her new client, Mistress Zelda kept a slow, steady pace, waiting nearly a minute before each swat. By the time the twenty-fourth and last prescribed seat landed, Hilary’s ass was a deep, dark red, and she sobbed from the painful burn in her tender backside. She knew she still had the leather strap and cane to go. As much as she was dreading them, especially with her shapely ass already so sore, she knew she needed the pain and humiliation they would give her.

Without a word, Mistress Zelda freed Hilary from her bondage and allowed her a few minutes’ rest to calm down. “Get up,” Mistress Zelda said in her typical stern yet caring tone. Hilary sat up and winced as her weight pressed down on her sore ass. She watched as Mistress Zelda placed a rounded leather cushion that was flat on one side, flat side down, across the bondage table. “Hips across the pad,” she instructed as she put the hairbrush back in its place and selected a thick and wide black leather strap with a polished wooden handle.

“Yes, Mistress Zelda,” Hilary said as she wiped a stray tear from her eye and crawled up onto the table before lying as instructed.

“One dozen lashes, are you ready?”

“Yes, Mistress Zelda,” Hilary replied as she pressed her forehead against the backs of her forearms. “OOOOWWWW!” she cried seconds later as the supple leather met her sore flesh with a loud and almost wet-sounding whap that seemed to echo through the dungeon forever. She kicked her legs as fresh tears fell from her eyes.

“Settle,” Mistress Zelda said in a firm tone as she gently pressed her free hand on Hilary’s lower back. Almost instantly, Hilary stopped kicking her legs and settled back over the pad. “That’s a good girl,” Mistress Zelda said before she delivered the second lash.

“AAAHH!” Hilary cried out again. As she did, she felt Mistress Zelda’s hand on her back once more, its presence both intimidating and comforting. Again, the dominatrix used a slow pace, not wanting to push too far. Just like with the hairbrush when the last lash had been given, Mistress Zelda gave Hilary several minutes to relax and calm down.

“Lunge position, right here,” Mistress Zelda instructed as she pointed to a spot on the floor with the cane she had chosen while letting Hilary rest.

“Yes, Mistress Zelda,” she replied as she slowly got off the table, then balanced herself on the palms of her hands and the balls of her feet.

“A proper lunge position,” Mistress Zelda said as she circled Hilary, admiring the way she held the stressful position despite the burning pain she felt. “I guess I shouldn’t be surprised. Only four storkes, Hilary, but they will be hard.

“Yes, Mistress Zelda,” Hilary said as she felt the dominatrix press the smooth, thin wooden cane against the spot where her thighs and ass met. She willed herself to stay still as Mistress Zelda slowly pulled the cane away, preparing to give Hilary the first of the four strokes.

It came quickly, along with the shrill whistle of the cane as it cut through the air and landed just where Mistress Zelda had indicated it would, where her thigh and ass met. This time, Mistress Zelda didn’t wait. The next three strokes came fast and hard, another landing where her ass and thighs meet, the final two higher up on her ass, among the bruises.

“Very good, Hilary. I’m very, very proud of you,” Mistress Zelda said soothingly. “Now, lie down and put your hands behind your back and bend your knees. Hilary didn’t reply through her sobs, but she nevertheless obeyed. Using a button on the wall, Mistress Zelda lowered a bondage rig from the ceiling. She placed two of the leather cuffs on the right around Hilary’s wrists, and the other two around her ankles. She then pressed the button again, causing the rig to retract and lift Hilary two feet into the air. “See you in twenty minutes,” Mistress Zelda said before leaving the dungeon.

For twenty minutes, Hilary hung from the ceiling like a side of beef, in strict and uncomfortable suspension bondage. By the five-minute mark, her arms and legs were burning just as badly as her ass. She began to focus on the lyrics of some of her old songs as she waited for the dominatrix to return. When she finally did, she was lowered to the ground and released from her bondage.

“Come with me, time to write your letter,” Mistress Zelda said as she clipped a leash to Hilary’s collar.