Ariana's new life begins

Jessica closed the gate that separated the private estate from the resort. As she did, she looked at the building that had appeared next to the play building, thanks to the wish she had just made.

"Keeping Arianna there is going to be so much fun," she said to herself. With a beaming smile on her face, she turned and power walked to the hotel.

As soon as Jessica entered the lobby, she noticed nearly everyone there looking at the front desk. As she turned her head to see what was so fascinating she heard Ariana Grande's voice.

"Let me go! You know that card has no limit!"

Jessica's smile broadened at what she saw. Ariana, dressed in denim shorts, a red tee, and black heels was on the ground tightly tied in black ropes. Standing over her dressed in a tight-fitting green sports bra, equally tight-fitting green pants, and brown boots that left her perfectly pedicured toes visible, was Ino Yamanaka.

"Not according to my computer, Miss Grande," Josephine replied in an even and cool tone.

"Ever the diplomat," Jessica thought. "What's going on here?"

All eyes were suddenly on her. Into stepped forward before kneeling in front of Jessica. "Mistress Jessica, this one cannot pay. When she ran I pursued and captured her."

"Very well done Ino," Jessica said in praise of the submissive ninja. "Since we will be slow through the week until Friday, you may have your pick of the whores to have some fun with in the play building as a reward."

"Thank you, Mistress Jessica, you are too kind."

"Guards, take Miss Grande to the new building."

"As you command, Mistress Jessica," one of the guards said before pulling her disrobing knife from its sheath. She cut away the ropes while three other guards held Ariana down. After the ropes, Ariana's clothes were cut away leaving her completely naked. Next, two more guards entered carrying a long sturdy wooden pole on their shoulders. Four leather cuffs sat on top of the pole attached to it with only a couple of chain links each.

"You can't do this to me!" Ariana screamed before one of the guards shoved a pink ball gag in her mouth.

"Actually I can. It's in the contract you agreed to when you checked in," Jess said with a slight shrug.

Jessica watched as the guards placed Ariana's wrists and ankles in the cuffs and then lifted the pole onto their shoulders. She followed behind the four guards as Ariana continued to scream into her gag and squirm against the cuffs.

When they entered the new building, the strong scent of hay hit Jessica's nose. Once inside she was not at all surprised to see that the building was just as she had pictured it. Along the left wall were several stalls closed off by half doors that stood roughly three feet high. In each stall, the floor was covered in soft bedding with scented blankets, along with a toilet, and a feeder that would dispense water and a nutrient-dense but largely tasteless paste. Along with the back wall, several small carts and sulkies sat side by side waiting for use. On the right wall were several open shower stalls very similar to those in the harem room bathroom. On the wall behind Jessica, there were two doors. The one leading back outside and the other to a large storage room filled with gear for ponygirls.

Lastly, the center of the building consisted of a dirt floor. At the very center of the dirt floor was a large wooden post with a long arm coming out of it about five feet up. A long lead was attached to the end of the arm. When activated by a switch near where Jessica stood, the arm would begin swinging around the post at a moderate pace allowing any ponygirl attached to the lead to exercise. On the far side of the dirt floor was a whipping post.

Ariana stopped struggling when she became momentarily distracted by her new surroundings. Jessica simply pointed to the whipping post and the guards carried Ariana over to it, and freed her from the pole, only to secure her to the whipping post.

As Jessica walked over to where Ariana waited she looked down at her left hand. “I wish I had a collar,” she said with a smirk. Instantly, a black leather collar appeared in her hand. She then looked at her right hand. “I wish I had a whip.” A whip appeared in her right hand and she circled Ariana until she stood in front of her. “Remove her gag,”

“As you command one of the guards said before removing the starlet’s gag.

“You don’t remember me, do you, Ariana?”

“No, now let me fucking go you crazy bitch!”

“A little hint, sweetie,” Jessica said in a mockingly sweet tone. “But of course, you wouldn’t remember someone who gave you a cup of coffee that you were too important to wait for.”

A confused look washed over Adriana’s face. “What?”

“A year ago, you came into a Starbucks in L.A. We were slammed and short-staffed. You, Miss Pop Star, Miss Actress, Miss Queen of the world were a total bitch to me because you had to wait just like everyone else.” Ariana tried to think back, but she had no recollection of the event. Though she didn’t doubt it, there were times when she knew she had been short with the staff at restaurants and shops when she was pressed for time. “Let’s cut to the chase, shall we?” Jess asked before holding up the collar for Ariana to see. “Ask for this now, and save me time and you a world of pain, or I use this on you until you beg me to put the collar around your neck.”

Ariana look back and forth between the collar, and the whip.” Fuck you,” she said defiantly.

“Have it your way,” Jessica said as she shoved the collar into her back pocket. She circled back behind Ariana and carefully measured out the whip.”Let’s see how many times I can whip you before you beg me for your collar,” Jessica said as she swung the whip over her head, building momentum for the first lash she would deliver. She focused her aim on Ariana’s ass.CRACK! The sound of the whip striking Ariana’s ass mixed with the sound of the singer and actress’ scream of pain as they echoed through the arena.

Jessica continued her relentless onslaught, cracking the whip against Ariana's exposed skin with an almost hypnotic rhythm. The pain from each strike was unmistakable, yet Ariana's defiance seemed to grow stronger with every passing moment. The guards, standing by the whipping post, exchanged glances as they watched Jessica in action, their eyes reflecting admiration for Jessica’s skillful use of the whip.

As the blows rained down on her back and ass leaving painful welts in their wake. Ariana's cries of pain, their pitch and intensity rising and falling like a symphony of anguish. The spectacle was both horrifying and captivating, drawing the attention of anyone within earshot including the dark-haired pony trainer. She was dressed in a black polo shirt, tight-fitting khaki pants, and knee-high dark brown leather riding boots.

“I can’t wait to begin training Mistress Jessica’s first pony. She is quite the beautiful mare,” she thought as she watched Jessica deliver lash after lash.

Jessica stopped whipping Ariana, who now hung as limply as the whipping post would allow, sobbing and breathing heavily. Jessica coiled the whip as she closed the distance between herself and Ariana. She grabbed Ariana’s long brown hair and pulled back hard as she held the coiled whip in front of Ariana’s face.

“Do you submit, or should I keep whipping you?” Jessica asked her voice low and authoritative.

Ariana's eyes welled up with tears, and her voice trembled as she managed to respond, "Please, I’ll take the collar. Please don’t whip me anymore,” she said weakly through her sobs.

"Good," Jessica said with a satisfied smirk. "Now, you will call me Mistress Jessica. Your other Mistress’ names are Emily, Eden, and Alura. You will meet them soon enough.

Ariana nodded, clearly defeated. "Yes, Mistress Jessica," she whispered, her voice barely audible.

Jessica let go of Ariana's hair, and she slumped forward, still bound to the whipping post. She pulled the collar out of her pocket and buckled it around Arian’s neck. Jessica looked at the guards and smiled. “Let’s get this pretty pony properly outfitted.”

“P-p-pony!” Ariana said in shock.

“That’s right, Ariana, you are going to be a ponygirl. Our first ponygirl. You will live here in this arena, and when I or your other mistresses want to go for a ride in that sulky over there,” she said as she pointed to the sulky pushed up against the wall. Ariana’s looked to where her new Mistress had pointed. There it was, the sulky she now knew she would sooner or later be **** to pull her new mistress around in. The sulky was made of dark, polished wood, with intricate patterns and carvings etched along its sides. The wheels were tall and slim, almost unnaturally so, and they seemed to gleam in the dim light of the arena.”You will be hitched to it and you will take us around the arena as many times as we want while maintaining perfect pony form.” A look of horror washed over Ariana’s face. “Get her dressed,” Jessica said to the guards as she hung the whip on a hook on the wall.

The guards and pony trainer worked quickly to place her in a bondage harness made of intersecting black and red leather straps. The straps framed and accentuated her breasts and kept her puss and ass available for use.

Next, they **** a rubber bit gag into her mouth that was part of a black leather harness that they wrapped around her head. When it was fully in place, two plastic blinders blocked her peripheral vision, a tall red plume rose from the center of her forehead, and at the sides of the top of her head were two leather horse ears.

Next, her feet were placed in a pair of thigh-high black latex boots that were shaped like horse hooves. As she moved as much as the whipping post allowed Ariana was horrified that the boots, made a pronounced clip-clop with every step she took. With Adriana now mostly dressed she was released from the whipping post, only for the guards to keep a tight grip on her. Jessica looked at the pony trainer and gave a nod, The trainer stepped in front of Ariana and began to speak.

“Ariana, I am your trainer. When you are not gagged you may call me ‘Ma’am,” calling me anything else will result in a visit to the whipping post. Nod if you understand.” Ariana slowly nodded her head.

“Good, now we will be walking to the far wall. Every time you step you are to lift your knees high, give a flicking kick, and take an elongated step, this is how a pony properly prances.” One of the guards gave a gentle shove forcing Ariana to carefully walk as she had been instructed. For the starlet, each clip-clop her boots made was like a dagger to her heart.

It seemed like it took forever to reach the far wall, but when they did, Ariana breathed a sigh of relief. “Bend over and stick your ass out hands flat against the wall,” her trainer said. Fearing being whipped again Ariana quickly obeyed. “I’ll be back, I’m going to find your tail.”

“‘My tail?’” Ariana thought as she heard the other woman walking away.

A short time later she returned with a selection of thick black anal plugs. At the base of each plug was faux hair made to look like a horse’s tail. The trainer then held up the faux hair to Ariana’s until she found a close match. Happy with one of the options, the trainer began to coat the plug with lube.

“Relax and push out like you’re taking a shit, it will make this much easier on you,” she said Ariana looked over her shoulder and her eyes went wide with fright as her trainer began to push the tip of the anal plug against her asshole. Ariana’s heart began to race a million miles a minute, and her breathing became quick and ragged. She grunted into her gag and bit down on it hard as the thick plug began to **** her tight hole open. Ariana screamed into her gag and her hips involuntarily shot forward as the thickest part of the anal plug went in.

“Oh God, did they do this to the celebrities that work as whores here? I never should have come to this damn island,” Ariana thought as she took slow deep breaths.

Her tail now in place the guards stood her up, pulled her arms behind her back, and **** them into a leather single glove. They cinched it tight forcing her elbows together painfully, and her chest out.

“How long do you need to have her ready?” Jessica asked looking at the trainer.

“Only three days at most, Mistress.”

“Well Ariana, I guess I’ll be seeing you in three days,” Jessica said trapping Ariana’s nipples between her thumbs and index fingers and giving them a painful twist. Tears began to flow from Ariana’s eyes once more as she realized her life as a pop star was well and truly over, and her life as a lesbian sex **** and ponygirl was just beginning.

What happens next? Answer in comments

A) Milena auctioned off

B) The three days pass

C) Alura has fun with Katie

D) Something else. What?