The Maid

The Maid

By Maid Jazz

05

Rita returned to her Masters chambers and stared in surprise. Sarah had put herself back into the bondage from before with a few changes.

Curious she moved forward and slowly circled her fellow maid. Instead of the cuffs she now wore a mono sleeve arm binder. It pressed her elbows together forcing her breasts to be displayed more prominently. She had a corset laced tight beneath her dress that seemed similar to the one she had trapped their master in. The hood was back in place with a gag locked in her mouth.

Rita slowly lifted her skirt and realized she now wore a chastity belt. It was locked in place and had the base of a plug in the front attachment point. Rita both winced and felt jealous as she finished checking over her outfit. With a sigh of both relief and disappointment, she turned away.

A note sitting on the bed caught her eye.

"Dear Rita,

I have discovered that Sarah has mailed a certain key, so I am unable to escape her prank. As punishment I have put her into the outfit you see before you. I have to attend an important meeting with my parents, so am unable to punish the little tease. Please do so in my absence. Do not do anything that could cause lasting damage.

Will"

Rita read the note over several times before she allowed a smile to grow on her face. Motion caught her eye as Sarah stirred. She had been asleep before and was now squirming in her bondage.

"So your games finally got you in trouble." Rita giggled rubbing her hand down Sarah's back "Don't worry. I will do all master bids while he is unavailable." She slowly circled her prey before lifting her skirt to expose her behind. The thong of the chastity belt left her ass completely bare.

"Oh this is going to be fun!" Rita laughed to herself as she pulled back her arm.

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Will woke to darkness. He instantly knew he was bound tightly. Some squirming confirmed that he was unable to move much at all. His arms seemed to be strapped together behind his back and a long gag was locked in his mouth. Running his tongue over it confirmed that it was shaped like a cock. His legs were strapped down to whatever he was forced to kneel on.

Unable to hear or see he was forced to rely on his other senses. Unfortunately they weren't telling him much. He jumped in surprise as a cool hand slid down his back.

A daft across his ass made him realize he must be wearing a skirt of some sort. The hated corset was still locked around his waist and he could feel his chest moving with every breath. The sensation was familiar and he realized she must have given him breasts once more.

"MMmmmmphhh!" he squealed into the gag as a blow landed on his ass. It was due more to surprise than pain but it still stung.

A pair of hands then massaged his ass, they were gentle, slowly calming him. They felt amazing and he found himself leaning into them.

The second blow made him jump but he held back to only a grunt. Now both his ass cheeks sported bright red imprints from her hands. They tingled and burned in a teasingly pleasant manner.

As his cock strained to grow he realized it was confined into something rather small that stopped all growth.

'Oh, I am really going to get her for this.' Will vowed as the next blow landed.

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Sarah watched the action from her hiding place under the bed, the bedskirt hiding her from view. She struggled to hold back her own sounds, as she enjoyed the show. Watching Rita spank her master while thinking it was her was ridiculously hot. She had one hand between her legs gently rubbing as the action heated up.

After several minutes she bit down on the hem of her dress as an orgasm rolled through her. She shook and gasped as the orgasm ran its course. She lay limply on the carpet just enjoying the moment.

Slowly she regained her strength and decided she better come clean. As she went to scoot forward the outer door burst open and guards rushed inside.

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Rita spun in shock as guards burst into the room. One pushed her back out of the way while the others surrounded Sarah. A moment later her previous superior and head maid, strolled into the room. She gave Rita a smirk as she crouched in front of Sarah and lifted her hooded face. "You have been naughty stealing pills from the supply cabinet." She tsked, "I now get to punish you for it."

"Take her to the main hall," she ordered and the guards scooped up the litter and carried her out the door. The spiteful maid laughed at Rita, "I may not be able to punish you just yet but know that it is coming." Her laugh faded as she left the room.

Rita stared after them with a worried look on her face. "This isn't good," she muttered.

"You don't know the half of it," Sarah declared, standing up from behind the bed.

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"You are going to be in so much trouble," Rita whispered.

Sarah cast her an annoyed look but nodded. "No shit. Will is not going to be happy." She had hidden her hair under a blonde wig. They were currently looking into the main hall where the disguised Will was being prepared for his punishment.

Rita frowned. "What are they doing to him?"

Sarah watched for a minute before responding "Its a fairly standard punishment for big time offenders," she replied. "His outfit will be changed and he will be chained on display for everyone to see. Staff are encouraged to spank or paddle as they pass." She took a deep breath. "It's the duration that's the problem. Usually the punishments are at least a week and the party is in 4 days."

"So, what do we do?"

Sarah shook her head "I'm not sure. They won't be able to remove his belt, hood or corset as they don't have the keys. So his identity is safe. We just need to get him back before the party."

Rita scowled, "At least Will got his mother to stop the morning check ins. His absence would be really hard to cover up."

Sarah nodded absentmindedly, "He is always planning ahead. Though I doubt he expected it to be needed quite so soon."

The pair let out nervous giggles as they frantically tried to think of a solution.

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Will knew something had gone wrong as soon as his litter had been picked up. He could tell that he was moved quite some distance before being lowered to the floor. Massive hands lifted him into the air as he was freed from the base. They held him up as his shoes were exchanged for knee high boots of some sort.

When they lowered him onto his feet he realized he must be wearing ballet heels as his toes were now pointed straight down. Luckily the guards held him steady as he tried to adjust to the boots.

They pulled the dildo from his mouth but slid another in before he could even lick his lips. The new one was much larger in both length and diameter. It slid into his throat and he began to choke. After a moment his throat relaxed and he realized the fake cock had been coated with a drug to stop his gag reflex.

He felt someone fiddle with his arm binder for a second before the tip began to lift. He was forced to bend over as it rose leaving his ass completely exposed. His legs were spread and cuffed in place leaving him bent over with his feet shoulder width apart.

He sighed into his gag half in annoyance and half in relief. While this would probably be painful in time it could have been a lot worse.

Then he felt a flap on the back of his chastity belt flip open.

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"Please!" Rita implored.

Rick leaned back in his chair with his arms crossed. "What's in it for me? I would be risking the Mistress's anger after all."

Rita gave him a seductive look. "I will make it up to you I promise."

Rick laughed. "No offense but your services are not worth that much."

Rita scowled but nodded, she knew that, likely it wouldn't have been enough. But she had promised Sarah she would try.

"However," Rick spoke as she turned away. "I'll do it for eight hours with yourself, Sarah and another maid."

Rita froze in place as she thought it over. While Rick as quite attractive he wasn't really her type. Though, this was to rescue her new master.

"You have a deal," she whispered before leaving.

Rick beamed for a moment before picking up his radio. "Call in all the guards not currently on escort duty."

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Rick replaced one of the guards standing watch over Sarah and winced at her exposed ass. Several people had obviously worked her over before moving on. In addition to a scarlet ass dozens of nasty lacerations and bruises were visible.

'Rita was on to something,' he mused. 'Someone really has it out for her.'

He could hear quiet gasps coming from the bound maid. To hear them through the gag meant she must be in a lot of pain. Seeing the area was clear he leaned towards his partner. "Check the upper level and make sure no one is around."

"Yes sir!" The man snapped him a salute and bounded up the curving staircase.

Rick waited till he got the all clear signal before pulling a small jar from his pocket. Unscrewing the lid he scooped out some of the ointment and gently began to smear it on Sarah's ass.

She flinched at his touch and stayed stiff as he worked. She was obviously afraid it was a trick. He shook his head. The poor girl was terrified. He kept his motions light as he worked the ointment into her wounds. Slowly her leg muscles relaxed and she began to make soft noises into her gag.

He kept his touch business like, as he quickly worked to cover everything. He knew he was short on time.

"What the hell do you think you are doing?" A woman's voice made him jump.

He quickly finished the last couple spots before turning to face the approaching trouble. "Kelly." He greeted his mistresses head maid. "A beautiful day isn't it?" He flashed his brightest smile.

"Don't give me that crap!" She snapped. "No one is allowed to help this maid."

"Oh?" He feigned ignorance.

She gave him a glower, not falling for it. "She is being punished for stealing. You know as well as I the punishment for that."

Rick nodded. "Public spankings and humiliation," he motioned towards Sarah. "Which she is receiving."

Kelly snorted. "No affection or help is to be rendered during this time. Violators will be punished." She clicked a button on her bracelet and Rick knew she had summoned her mistress.

'Well this just got complicated,' he mused, pretending he hadn't noticed. She continued to harass him as they waited.

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"So why have you disobeyed a house rule?" Lady Vivian asked in a dangerous tone.

Rick stood up straight before her. "I acted to save one of your staff from permanent damage."

Vivian's eye brows rose, "Oh?"

Rick motioned to Sarah's bound form. "See for yourself."

The lady of the house lifted the maids skirt and hissed upon seeing the wounds. "Who did this?" she demanded in a quiet voice.

"We don't know," Kelly replied, cutting him off. "But I will find out."

Rick pressed on his ear piece as he got a report from one of his men. "I may be able to shed some light on this." He pulled out his tablet as they both turned to him. Clicking on a new message he handed it to his boss.

She watched the video and her expression darkened as it played. Beside her Kelly paled and began to back away.

"Don't move another inch!" Vivian hissed.

The senior maid froze, looking like she would fall over.

Rick kept an eye on her as his mistress finished watching the security footage. It took several minutes even with the extras removed.

When done, she handed the tablet back to Rick with a murmured thank you. She turned to her trembling head maid and glowered at her.

"I though it was what you..." Her words cut off as Vivian held up a hand. She gasped as her mistress ripped the senior badge off of her uniform.

"You will pay greatly for breaking our rules," Vivian pronounced. "Process her as a new pony."

Kelly gasped and tried to run but the two guards assigned to the mistress caught and stripped her. In short order she was naked and hog tied on the floor. A red ball gag muffled her cries.

"Thank you Rick," Vivian announced. "I will leave the rest to you. Ensure Sarah joins her in the stables. They can work together and maybe put this crap behind them."

"Yes Mistress," Rick replied, motioning for a pair of his guards to grab Kelly. He himself freed Sarah and slung her over his shoulder. They then moved off for the stables.

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"I'm not sure this is an improvement," Rita whispered, watching her master being carried off.

Sarah just grunted and chewed on a nail. "At least he isn't being hurt any more."

Rita turned to her with a surprised look, "Being a pony girl isn't much better."

Sarah shrugged, "we need to find a way to free him."

Rita looked at her speculatively, "you willing to trade places with him?"

"In a heart beat," Sarah declared.

"Good," Rita replied. "Then we need to find matching gear to his and wait for an opening."

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Will slowly trotted in a circle. He was hooked up to a walking machine and had been for several hours. Mild shocks were applied to his nipples and butt plug if he slowed or failed to lift his feet high enough. His poor ass was feeling much better after multiple applications of balm over the last couple days. The tails also had special lube applied that made their bodies more pliable and sensitive. He had come to enjoy the full stretched feeling and knew he would miss it later.

He had spent a fair amount of time clipped to a small cart beside another pony. They only ever worked together so he gathered he should know who she was. With his blinders in place he only ever caught brief glimpses of her, which didn't help him narrow down her identity.

He slowed to a stop as gentle tension pulled back on his reins. A groom came and unclipped him. A gentle tug on his reins led him into a nearby stable. He was led over to a strange sawhorse and bent over it, a couple of straps holding him firmly in place.

He waited with a racing heart as he could sense movement behind him. He jumped as someone grabbed his tail and slowly worked it free. Will gasped as the massive plug popped out. His relief was only temporary as something warm slid into his gaping ass. His eyes flew wide as the cock easily slid in to the hilt. He let out a moan, its warm length much nicer than the cold plug. It also reached deeper and pressed against that perfect spot.

Hips slammed into his ass in a steady rhythm as the cock was pumped into him. He only half noticed the groom coming around to gentle rub his head.

"Good pony's deserve rewards."

Will was so surprised by the fucking that he just stared in shock. The man moved away.

"Enjoy yourselves," he called over his shoulder.

Will moaned and closed his eyes as the thrusts continued. When he opened his eyes he noticed a mirror set into the far wall. The image it showed took his breath away. A beautiful ponygirl, bearing a striking resemblance to his personal maid, was bent over and strapped into place with a well hung ponyboy slamming his cock into her.

To his surprise his arousal spiked as he watched. Watching his helpless maid get ravished by the stud had his cock straining against its cage. His nipples pressed into his corset as he rocked with each impact. His enjoyment spiked as he watched, panting in time with the thrusts..

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Rita slowly approached her master trying to stay calm. He was still strapped down and appeared to be asleep. The ponyboy had already been taken away so she knew that time was short. She quickly undid the straps holding him down and lifted him upright.

He had spotted her in the mirror and quickly followed her as she opened a nearby stall.

Sarah waited within dressed identical to him. She quickly headed to the bench he had been in and was strapped into place by her fellow maid. She settled in to wait knowing she would be trapped for a while.

Will waited impatiently for his maids to finish standing inside the stall. He was still fully bound and couldn't do anything to get away.

Rita stepped in beside him and closed the door. "We need to get you to your room," she explained. "Unfortunately we only found one way across the yard." She motioned to the back of the stall.

Will glanced over and felt his eyes go wide. A small carriage sat there waiting before the exterior door. All it was missing was the ponygirl before it. With a sigh he nodded allowing himself to be strapped into place. When the outer door opened he squinted till his eyes adjusted. A gentle snap of the reins urged him forward. With a pounding heart he left the seclusion of the stall and stepped out into the light.

Even though he had spent the last couple days pulling carts around the property, this time it felt much different. Part of it was instead of a disinterested groom he was now pulling his own maid around.

He found himself trotting with perfect form, his training having instilled that need in him. His hooves clopped out a steady beat as they slowly worked their way across the yard. No path lead directly to the main house so they had to make multiple course corrections along the way.

He kept his gaze straight ahead whenever they passed a cart heading the other way. Their own ponies not reacting either. Ponies were meant to keep their eyes on the road at all times. Blinders assured they weren't distracted by their surroundings.

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Will heard the approaching cart well before it caught them. Many hooves clopped along together as it over took them from behind. He stayed to the right side of the path as pairs of ponies trotted past him on the left. Two sets were past him before their driver gave a soft order and their speed slowed to match him own.

"Good Evening Rita," His mother's voice called out. "Such a lovely afternoon for a ride."

Will nearly stumbled as he realised he was in plain view of his mom dressed as a ponygirl and pulling his own maid around. The humiliation had his cock throbbing within its confines.

"Good Evening Lady Vivian," Rita replied politely. "That it is. The fresh air is so refreshing."

"Quite. Where did you ride to?" came the reply.

"I went to check on Sarah," Rita admitted. "She seems to be doing much better now."

His mother laughed, "Yes, I have heard Storm has that effect on most good ponies."

Will stifled a moan, he knew Storm's cum was still within him, sealed in place by his tail. His cock throbbed as he remembered being taken by the well hung stallion. He shook off that train of thought. He needed to stay focused and not draw extra attention to himself.

"Which pony is that?" Vivian asked, making his blood run cold. "I don't recognize her, though she has a passing resemblance to Sarah."

"I'm not sure," Rita replied smoothly as the carts rounded a gentle curve together. "Maybe a distant relative?"

"Maybe," She replied. "Look at that ass though, not many are that tight."

Will gaped as his mom complimented his ass. He kept on trotting, knees pumping as he imagined their gazes riveted on it. It was both mortifying and arousing.

"Enjoy your ride," Vivian called before giving a crack of her whip. Her team surged forward, breaking into a run. They glided past before taking a gentle turn to the left.

Their own course took them right and he nearly sagged in relief.

Rita sagged back on the bench, her heart racing, 'That was entirely too close.' She quickly guided them towards the stables attached to the main house.

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Will plopped down onto his bed in relief. He was still trapped in the ponygirl outfit with his hands bound behind him in the arm sleeve. He was positively shaking from nerves as he tried to get his breath back. After pulling the cart across his parents expansive estate he had had to run to the safety of his room. The danger was high as pony girls were not allowed in the house. Hoping he had made it unnoticed, he now tried to calm his racing heart.