The Maid

The Maid

By Maid Jazz

01

William Conrad Queston the 3rd stared out his window at the storm raging beyond. Vicious wind and lancing rain assailed his parents beautifully maintained garden. He found himself grinning as he imagined his mothers rage at the damage being wrought. She cared for the garden more than anything else and it gave Will great pleasure to watch it get destroyed. Not that he could see much through the sheet of water cascading down the glass but the occasional glimpse was enough.

A gentle knock sounded from behind.

"Enter!" He called without looking away from the storm. Light flooded into the room as his outer door opened. It faded a moment later as soft footfalls approached.

"Master Will. I have returned," a familiar voice announced.

Will turned to his maid with a grin, "Just in time Sarah," he glanced at the bag she was carrying. "Did you get it?"

Sarah was his closest friend and personal maid. She had been assigned to him once he started school and she was never far from him. She was a dainty brunette with long hair that she kept pulled back into a ponytail. As was normal, she wore her maid dress. Mostly black with white lace trim it looked both classy and sexy. The skirt was pushed out by the crinolines beneath it and fell to mid thigh. An apron was built into the dress with its strings tied in a large bow behind her back. Sheer stockings encased her legs while six inch strappy black heels made her stand taller than Will. Matching bands of black and white lace encircled her wrists and a small cap was pinned into her hair.

Sarah nodded and hefted the duffle bag. "I found most of what you wanted, but had to adapt others to work."

Will nodded, "I am sure you have done well. Let's see what you got."

XXX

Will stepped over to the sink in his room and filled a glass with water. He glanced at the small pill in his hand for a moment before popping it into his mouth and washing it down with some water. He knew it would act quickly so he proceeded with his plan. He had undressed earlier so it was a simple matter to remove his robe and hang it on its hook. From there he turned to the stack of clothes on his bed. They were what Sarah had brought him earlier.

They were simple clothes that Sarah had taken from the staff supplies. Will's parents always wanted their servants to look respectable so they spared no expense on their uniforms. The servants were required to wear fancy outfits as if they were serving at a formal function at all times.

Because Sarah had to pilfer the items they weren't a matching set. Will knew they wouldn't stand up under close scrutiny but figured they would be good enough for his purpose. He grabbed the underwear first and slid them up his legs. He gasped as it settled into place and the thong sunk between his cheeks. Though silky the thong had a pouch on the front to support his boys. It took some adjusting but everything eventually fit. He spent a couple minutes cursing his mom for making male servants only wear thongs. It was so they had no unsightly lines in their uniforms she had explained multiple times.

Next he slid on thin black socks. They were quite short and barely covered his ankles. Will pushed aside the feeling that they were women's and continued to get dressed. No one would be seeing his socks anyway. He grabbed the pants and immediately noticed that they weren't the right ones. The typical male servant pants were black dress pants with the family crest done in silver on the right leg. These pants were black and stretchy and the crest was on the left leg.

A quick check revealed no other options so he pulled them on reckoning he would take them off if they were noticeable out of place. They proved to be skin tight and fit like a glove. Other than compressing his boys even more they were quite comfortable. Ignoring the discomfort for the moment he pressed ahead. He quickly pulled on the shirt and buttoned it up. A silver tie followed before he stepped into the shoes. A black jacket completed the outfit.

Will moved over to the mirror and glanced over his reflection. As expected the pants did not work and made him stand out. He sighed in exasperation and disappointment. He had been looking forward to escaping from his room for a bit. For the last year he had been closely followed and guarded by a minimum of a dozen guards at all times. His parents had even put tracking devices into all of his clothing so they would know his every move. All of this had started after his younger brother had been killed during an attempted kidnapping. Ever since, his parents had become extremely over protective and paranoid. He just wanted to get out on his own and relax for a bit.

With a glum expression he looked at his changed appearance. Thanks to the pill he had taken earlier his hair was growing before his eyes. Where it had been a buzz cut before it was now nearly to his shoulders. The pill was intended for those who wished to change their hair style quickly. Though expensive there was a huge supply of them in storage. He would have to get Sarah to cut it for him so no one would notice.

A soft knock in a particular pattern told him Sarah had returned.

"Enter," he called still looking at his reflection.

The door opened and he heard a wolf whistle from her. Spinning in place he cast a glare her way.

"What?" she demanded with a grin, "You totally have the ass for those pants." she glided over to him and wrapped her arms around him to cup his ass. She lifted him forward into her as her hands squeezed. "Its such a shame you hide this away all the time," she breathed into his ear.

Will swallowed hard and tried to reign in his arousal as she stepped back. He tried to think pure thoughts as the thong wouldn't contain him if he got too aroused. He noticed Sarah hiding a smirk as she stepped back. 'The little minx is doing this on purpose,' he realized.

"So what do you think?" she asked of the outfit, "It was the best I could find on short notice."

He shook his head, "Everything but the pants are good. But they will get me caught for sure."

Sarah nodded, "True enough but I have a solution to that."

"Oh?"

She turned to a bag she had set aside upon entering the room. From it she pulled two shiny black garments and held them up triumphantly. "Rain gear."

XXX

Will followed his maid through the house with his eyes downcast. He was afraid of being recognized so he stayed tight behind her and avoided looking at anyone. The rain coat he now wore covered him to the knees and mostly hid the pants he wore. While the calf section was much tighter than normal he figured no one would think anything of it. At least he hoped they wouldn't.

Sarah grinned as her master meekly followed her through the mansion. She got a thrill out of teasing him. The current situation had her highly wound up. Her nipples were so rock hard that she could feel her shirt rubbing against them with every step. Her panties were damp and she knew her cheeks were flushed. Thinking of how she had tricked will into wearing woman's pants by pretending that was all they had was just icing on the cake.

They were heading for the garage to make their escape from the estate. Unfortunately it was on the far side of the mansion so they had a long way to go. Knowing Will was distracted Sarah purposefully took them on a round about route to extend his embarrassment.

XXX

"You are purposefully take the long route aren't you?" Will growled from behind a half hour later.

Sarah continued walking and shrugged. "I'm just trying to avoid the busy areas. Feel free to lead if you like," She offered.

A heavy sigh was her only response.

Less than a minute later they turned a corner and could see the entrance to the garage. "See we made it here without any issue," Sarah boasted.

"You two!" A voice shouted from behind.

Both froze in shock before slowly spinning towards the authoritative voice. A lead butler strode towards them. The crimson patch on his shoulder signified his rank. "Come with me," he ordered, "You are late and will be punished after we are done."

Will glanced at Sarah in worry and gaped as she curtseyed and gave an affirmative. As she rose she caught Will's eye and gave him a wink. Without waiting she turned and followed the butler.

Will glanced at the garage before sighing and following his maid with his head bowed.

XXX

"This is crazy!" Will yelled as he pulled on the rope. Even with his full body weight he was being dragged back and forth by the howling wind. He was thoroughly soaked and had forgotten completely about his outfit.

Sarah didn't respond and Will doubted she could even hear him. She was only a couple feet away but the strength of the storm was such that talking was impossible.

Wills loose hair was whipping around freely and constantly blinding him. It amazed him how much of an issue it was turning out to be. With his hands full and no way to pin it back he just grit his teeth and toughed it out. Dozens of other slaves were working to fasten down ornaments and trees in his mothers garden. He didn't find the storm funny any more.

XXX

Will stumbled into warmth as Sarah dragged him through a doorway and into the building. He was shaking from the cold and was oblivious to his surroundings. Shortly he was guided into a room and she peeled his clothes off. Moments later he was guided into a shower. The warm water felt amazing and slowly brought him back. He started and gaped when he realized Sarah had hopped into the shower with him. She was as naked as him and her breasts were pressed into his back as she supported him.

Will just relaxed into her embrace as they both warmed up. The feel of her soft breasts against his back had his cock rising to attention. He ignored it and just enjoyed the moment.

Sarah grinned as she spotted his arousal but made no move. Her grin slowly faded as she realized how much trouble she had caused. Her master had never been anything but fair to her and she had put him into harms way. While he appeared to be OK that didn't change the fact that she had pushed him too far. She caught herself right before she let out a big sigh and instead tightened her arms around him.

She wouldn't let anything happen to her master.

XXX

Will woke slowly from a wonderful dream. He could still feel a warm mouth sliding up and down his.... He jolted fully awake as he realized the sensations were real. A glance down revealed Sarah looking up into his eyes as her head slowly bobbed up and down.

She gave him a wink and continued. Her motions were slow and steady as she sucked. Her tongue continually licked along his length with each bob. Her mouth and technique felt amazing and had him moaning and clenching his fists. He closed his eyes and savoured the moment. She was going slow enough to amp him right up without pushing him over the edge.

Sarah loved the desperate look on her masters face as she teased him. She was enjoying herself immensely and found herself incredibly turned on. Ignoring her own pleasure she focused on his. Soon enough he was crying out for release.

She pulled off and gently stroked him with one hand. "Would my prince like to cum?" she asked mischievously.

He nodded and gasped.

"I'm sorry?" She asked stopping the motion, "I couldn't hear you."

"Yes!" He gasped out thrusting his hips upward but she moved her hand with the motion to deny him.

"Yes what?" She teased.

Will looked down at her with a tortured expression. "Please make me cum," he gasped.

Sarah clamped her legs together, as she almost came from having him under her control. "Would you do me a favor if I do?" She asked coyly.

"Yes of course!" He screamed out without hesitation.

Again Sarah had to stave off an orgasm. She couldn't believe how much this was working for her. "Then ask me nicely," she ordered running one finger gently down his throbbing member.

He bucked beneath her and gasped before taking a deep breath. "Please let me cum. I will do whatever you want!"

Sarah watched his eyes as he pleaded and felt another thrill run through her. He was totally at her mercy. When he focused on her she arched an eyebrow.

"Please let me cum mistress!" he cried out.

That pushed her over the edge. Her pussy clamped down as a small orgasm rocked her body. Stifling a cry she dropped onto his cock and worked it for all she was worth. Her motions were rather sporadic as she quaked and shook under the effects of her own orgasm.

Will gave a cry and erupted in her mouth. Even distracted, Sarah kept going. She eased off on the suction and swallowed all he had to offer. When he was done she rolled to the side and tried to calm down. She quickly got her breath back and glanced over at her master.

Will lay on his back with his eyes closed and a content look on his face. His breathing was deep and even. He looked so cute with his tussled long hair that she nearly attacked him again.

"Master," she whispered

"Mmmmm?" he grunted

"We need to get going," she replied, "Before anyone notices you are gone."

Will didn't reply for a minute before his eyes flew open and he glanced around. A minute later he sat up and sighed. "I didn't even realize this wasn't my room," he gave his maid a mischievous grin, "Someone had me slightly distracted."

Sarah rose with a grin, "Only slightly?"

XXX

They quickly realized another problem. Neither of them had anything to wear. Sarah was still in her bra and panties but Will was completely nude. In her desperation to help her master Sarah had dumped their wet clothes down the laundry chute.

They were in one of the guest buildings across the yard from the main house. It had been the closest so Sarah had brought him there. A quick search found a few outfits but the place was otherwise empty. Sarah brought the different outfits out and laid them on the bed. Who ever the last guest was, they were obvious female as their were no male clothes to be seen. She quickly vetoed over half the outfits right away. The fancy gowns and bikinis were not reasonable options.

Left were four outfits. A pale pink maid outfit, a grey skirt suit, a short yellow sun dress and lastly a one piece swimsuit and fluffy white robe. Will paled when he spotted the outfits but they were running out of time. His guards always checked on him at breakfast. He had just over an hour to get back to his room.

"I have an idea," Sarah admitted, "But you probably won't like it."

XXX

A half hour later Sarah knelt before Will giving him another blow job. This time she was pressed for time so she didn't hold back in the slightest. As he got closer Will grabbed the back of her head and took over control. Sarah only fought his grip for a moment before relaxing and just going with it. His ass and hips thrust back and forth faster and faster.

Sarah kept up her suction and tongue action urging him on. His thrusts lost rhythm as he blew his load with a strangled cry. She quickly sucked him dry and cleaned him with her tongue before looking up at him. Will glanced down and gave a nod after hesitating briefly.

Sarah gently lifted his dick out of the way and slowly pushed his balls up into his body. She was gentle but Will still winced each time. The pain was just a faint ache but it was far from comfortable. With that done she grabbed the material around his knees and worked it upwards. As the crotch came up she tucked his cock back between his legs and pulled it up tight. She quickly worked the rest of the garment up and guided his arms into the sleeves.

Hiding a grin she rose to her feet and stepped back to have a look. The plain black swimsuit fit him like a glove. Though lacking breasts, he definitely looked the part. With his cock hidden and crushed by the too small suit there was no sign of his true gender. As her master blushed and looked at the floor she circled him slowly. The leg openings of the suit were cut quite high exposing his hip bones. In the back the suit narrowed to a thong that disappeared into the cleft of his ass. Sarah grinned and resisted the temptation to pull on the thong.

"Not bad," she admitted, "with shoes and the robe this might just work. You actually look a lot like your sister."

"Thanks," Will muttered sarcastically, "Just what every guy wants to hear." He patted his chest, "Though she has a lot more up top than I do."

Sarah nodded, "I found something for that. But again you won't like it." At his questioning look she continued, "I found two bust enhancer pills. They are the short duration ones for small increases."

Will's eyes flew wide. He had heard of the pills but obviously never used them before "How do they work?" He asked genuinely curious.

"Then are premade to add a certain size to someones bust for a set amount of time," she explained, "Women use them before those all import big dates to lure in their prey." She glanced down at the bottle, "These are for the smallest increase with a two hour duration," she lied covering up the 24 hr tag on the bottle with one finger.

Will hesitated, "Is that really necessary?"

Sarah shrugged, "It wont hurt any. Plus the robe isn't thick enough to hide the fact you are flat. They won't last long so what harm will it do?"

Will frowned but nodded and held out his hand. Sarah hid her grin and dropped two pills into his hand.

"Two?"

She nodded, "They are for small growth after all."

Once he took the pills, she passed him the robe and pointed to a pair of fluffy pink slippers. They had a blocky two inch heel but were the only pair of shoes that went with his outfit at all. "Slip those on and lets go."

She was already dressed in the pink maid outfit and though it was slightly too large she was able to make it work.

XXX

Sarah followed Will across the yard and enjoyed the show. The storm had let up a bit and the rain had stopped. The wind however still howled and her masters robe was constantly being blown open. Watching his cute little ass cheeks glide back and forth over the thong of the suit made her day. He tried futilely to hold his robe closed as they moved. The wind hid his unsteadiness in the heels and stopped him from noticing his maids joy at his predicament.

As they moved his bust began to grow. By the time they were halfway across he was sporting b cups and they were still growing. Sarah hoped they didn't grow too much more as she had meant it as a harmless prank. They were at least c cup by the time they reached the main building. The suit was supporting them nicely and Will didn't seem too troubled by them.

Once inside they smoothed their clothes before setting off for Wills room. Now that the wind was gone he became very aware of his new breasts. They bounced and jiggled with every step. He finally resorted to crossing his arms under them for support. His expression had darkened and he fairly stomped through the halls.

Sarah watched in awe as several servants caught sight of them but quickly vanished upon spotting his expression. No one wanted to suffer a masters wrath. To her amazement no one impeded their progress and they made it to his room with time to spare.

Or so she thought. Will had just removed the robe and slippers when their was a knock on the door.

"Breakfast," called out the maid delivering it.

Sarah scooped up the robe and slippers and headed into the bathroom. "Just a minute!" She replied opening up the first aid kit and grabbing what she needed.

Will ran to his closet and quickly pulled on some clothes. His parents had several morning rules that had to be followed. You were to be up and dressed to eat at the table when breakfast arrived. He knew he couldn't just hide as the maids would report his status right after delivering the food.

Will jumped as Sarah came up behind him and pulled up his shirt. Moving quickly she started wrapping a long tensor bandage around his bust. She pulled it as tight as she could ignoring his winces. In less than a minute she had the bandage clipped into place and let his shirt fall. He quickly stuffed his hair up on top of his head and crammed a cap on over it. Will quickly finished dressing as Sarah moved for the door.