CrossdressingChapter 3 of 6Ongoing

The Maid

The Maid - 03

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The Maid - 03

The Maid

By Maid Jazz

03

Still thinking about possible solutions, Will wandered into his closet to pick an outfit. A noise made him look back at Sarah.

She was grinning in a mischievous way. "Let me get your outfit for you," she offered.

Suddenly worried he shook his head, "I am already up. You can chose tomorrow." He turned back and moved over to the closest hangers.

Slim arms wrapped around him from behind startling him. "Please master," she whispered. "I will make it worth your while." One of her hands stroked him through his pants while the other slid slowly across his chest.

Though suspicious, Will felt his resistance fading. "What are you up to?"

She gave a small laugh and continued her ministrations. "You will see soon enough. But you have to wear what I chose. Any complaints will earn you punishments."

"What sort of punishments?" He asked with a husky voice. His eyes were now closed and he was leaning into her.

"Mmmmm," she purred. "A nice spanking perhaps?"

Will moaned as her hand deftly glided up and down his erection.

"Do we have a deal?"

Will gave in and nodded.

"Perfect," she declared pushing him towards the exit. "I'll bring your clothes right out."

Will stumbled and glanced at her in shock but her teasing grin made him flash her one of his own before leaving.

He moved back over to his chair and sat down to read some more.

Off to the side Rita slept peacefully on his bed, the cream hard at work. Exhausted after a sleepless night she was down for the count. The covers had been pulled over her providing a safe haven as she healed.

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"I'm ready," Sarah called. "Close your eyes and let me surprise you."

Feeling generous, he did as bid. Her hands pulled him to his feet and led him over by the bed. She then slowly and sensually stripped off his clothes. She took her time constantly stroking her hands all over his body. She loved the feel of his hairless body and wished she had made him do that years ago. By the time he was naked, he was panting and leaning into every caress.

"Has someone been a good boy?" She asked in a whisper.

He nodded and licked his lips. Trembling beneath her touch.

"Are you going to wear everything I picked out, with no complaints?"

Again he nodded wondering why she was going so far. Nothing in his closet was extreme enough to warrant her actions.

"Good boy," she whispered. "Lift your feet one at a time," she ordered.

He did so and felt her feed his legs into a pair of underwear. She held them by the waist band on either side and pulled them all the way up in one smooth motion. The material was soft and smooth and settled into place easily. His throbbing erection poked out the top of it but that was fairly standard. They were some sort of brief which limited the options as he usually wore boxer briefs.

"Good boy," she whispered. "Now sit down and skooch back a bit."

He did as directed and felt her lift one of his feet. Something tight was guided over his foot then up his leg. He quickly realized it was a pair of tights or some such. He amended that to stay up stockings when she stopped mid thigh and it stayed in place. "What are you up to?" He asked.

"I just figured we could have some fun," she replied while sliding the second stocking up his other leg. "I find this a huge turn on," she admitted. "Besides you promised."

He sighed but nodded "Alright. But I will get you back for this."

Sarah grinned at his words and grabbed the last item. "Just one more thing."

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Will walked through the devastated garden with Sarah following slightly behind. He tried to act casual but every step reminded him of what he wore underneath his clothes. The panties futily tried to keep his erection under control while the stockings slid again his pants with every step. The feeling was electric and sent shivers down his spine. Lastly the silk slip he wore felt divine against his hairless skin. It seemed to stroke him constantly when he moved.

Sarah had convinced him to spend the morning outside his room. At first he figured she wanted to embarrass him but the longer he was out and about, the more he realized he was enjoying the thrill. The hovering sense of danger also added to his arousal.

All around him workers rushed to repair the garden. It looked like absolute chaos, but he knew it would be restored in short order.

"William!" He heard a voice call out and he was tempted to pretend he hadn't heard. Stifling a sigh he turned to see his mother beckoning him over. Pasting a fake smile in place he strode over to her, enjoying the sensation of stocking covered legs sliding against his pants.

"Did you forget your promise?" She demanded once he arrived.

Will frantically thought back over their past conversations but couldn't remember anything. "Which promise are you referring to?"

She turned a stern gaze on him, "Why the one where you volunteered to help at my function this afternoon."

Will tried not to frown as he knew he had never been asked. But he also knew his mother, so there was no sense fighting it. "Where and when do you need me?" He asked.

"Right away of course," Came the sharp reply.

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An hour later Will was bored out of his mind. He had been assigned to escort the guests to the sitting room for tea. Once he had done that he was forced to stay beside his mothers seat and answer any questions the women had. Slowly realization dawned as to what she was up to.

She was showing him off to her rich friends in the hopes of finding a match for him. He was pretty sure each of them had a daughter around his age. Irritated he forced a smile onto his face as he tried to remember which daughter each one had.

In the end a party was planned for a week later. Everyone guaranteed they would be there with their families.

Will was only released once he promised his mother that he would attend. She made it quite clear that life would suck for him if he stood her up or refused. With a sigh he staggered down the hall to his room. Halfway there he stumbled to a stop before retracing his steps.

"Come in." His mother called after he knocked.

He sat down across from her and took a moment to gather his thoughts.

His mother watched him rather impressed. He clearly was on a mission and was being rather mature about it. She hid a grin as she decided he was starting to grow up.

"I have a request," He declared

"Go on," she murmured sipping her tea. 'What could he possibly want?'

"If you meet my conditions I will not only attend the party but cooperate fully in all you have planned."

She nearly choked on her tea. She set the cup aside and looked at him closer. She needed him to cooperate and had planned on tricking him into it later but this could be the opening she needed. "State your conditions."

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He stepped back into his room and froze in shock. Rita lay face down on the floor before him while Sarah finished hog tying her. Two pairs of hand cuffs had been used. The interconnecting chains hooked around each other.

Rita for her part was fighting to get free for all she was worth. She was also yelling but her cries were silenced by a stocking that Sarah stuffed in her mouth. A second stocking had been used to hold it in place.

Will purposefully let the door slam behind him.

They both jumped and looked at him. Rita's eyes were wide, while Sarah actually looked guilty for a moment before her face returned to normal. She adopted a standard waiting stance with her hands clasped before her.

"Welcome back master." She greeted him warmly.

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Will settled down into his favorite chair watching the two maids closely. Rita stared at him wide eyed from her position on the floor. She almost seemed scared to move. Sarah however was the complete opposite. She met his gaze smiling brightly the whole time.

Will took a sip of the iced drink beside his chair and just watched them. Both resisted initially before Rita started to crack. She started pulling against her cuffs but achieving nothing. She also could no longer meet his gaze.

Sarah's smile slowly faded. "Is there a problem master?"

Will held in a laugh and motioned towards the trussed up maid. "Care to explain?"

Sarah's grin came back and she nodded. "She was trying to leave."

"Oh?" Will inquired. "Was she not allowed?"

"Normally yes. But she was trying to sneak out without you knowing. She wanted to avoid causing any more trouble or get in trouble herself."

Rita grunted a couple times into her gag and closed her eyes. Her body relaxed as she seemed to give up.

"That true?" Will asked.

Rita avoided his eyes but nodded.

"Release her." Will declared motioning towards the bound maid.

To her credit Sarah didn't even hesitate. In seconds both sets of cuffs were removed and Rita was able to stretch out. She slowly rose to her feet rubbing her wrists. "May I go sir?"

Will shook his head. "No. Your quarters have been given to another."

"What?" She stared at him wide eyed, "I was fired?"

Will laughed before noticing her panicked expression. "Hardly," he explained. "You are now one of my personal maids. You report to me and me alone." He saw Sarah start from beside him. Glancing at her he continued, "You now have another to help you in your duties."

Sarah nodded thoughtfully. "What did you do to get this out of your mother?"

Will hid his smile. She always was sharp. "I promised to show up and behave at the party she is throwing to find me a wife."

Sarah's smile faded at that before she recovered. "A wife huh?" She fell silent thinking about that.

Rita just looked stunned. She kept going between ecstatic and worried. Will watched the emotions flash across her face. After a couple minutes she got it under control. "Where do I stay sir?"

"Master!" Sarah interjected.

They both looked at her. "Call him master, not sir. He now controls your fate."

Rita nodded, "I'm sorry master. Please forgive my rudeness."

"Of course." Will waved it off. "You will have new quarters connected to my closet next to Sarah's. The construction should start shortly. They are repurposing the spare room next to mine"

Sarah glanced at him surprised, "But that room is huge."

Will grinned "That it is. I am making several changes and upgrades to my room."

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Rita gave a squeal of half terror half joy as the car drifted through the turn. She was sitting on Sarah's lap in the passenger seat as Will drove. Sarah just laughed wrapping her arms around her fellow maid. She tightened her grip so they wouldn't shift around as much. She flashed Will a grin which he returned.

As the corner ended he opened up the throttle exhilarating at the feel of 1200 HP leaping to his command. Rita gave a scream of shock as the acceleration pressed her back hard. Sarah let out a woof as the air was forced out of her. But her grin and the twinkle in her eye didn't fade.

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"That was crazy!" Rita declared as the girls flanked Will through the mall.

They had driven that quickly to lose their tail. Will's assigned body guards had not been able to keep pace. With some time to themselves they wanted to make the most of it.

They drew plenty of attention from those they passed. Looks of jealousy, disgust and admiration were just some of them. It wasn't everyday you got to see two beautiful women dressed as sexy maids walking through the mall.

"Hey babe!" A man declared blocking their way and looking at Sarah. "Want a real man to show you a good time?"

Sarah didn't miss a beat. "That's what my master does all the time. I'm afraid you just don't measure up to my standards."

That took the guy by surprise and he just stared after them in shock as they moved on. Rita looked horrified while Sarah was trying to contain her laughter. "What if he gets angry?" Rita whispered.

"Then I kick his ass!" Sarah replied with a grin, completely unfazed.

Will shook his head and followed her subtle directions on his arm. She guided them to a fancy lingerie shop. Will shrugged and strode inside.

"Can I help you..." The store clerks voice faded as she noticed the maids. "I'm sorry but we don't serve prostitutes here." The woman's nose rose as she spoke till she was sneering down at them. "You will have to leave or I will call security"

Will just chuckled predicting what was about to happen. He could see a half dozen other women in the store watching avidly as this played out.

"Are you sure?" Sarah purred closing in on the woman. "This is Will Queston after all."

The young woman bristled at her approach "I don't care what your pimp is called. Now get out, before I have you thrown out" She reached for the phone.

Will noticed a middle aged woman pushing through the store towards them looking rather frantic. "Trish!" She half yelled.

The clerk smirked upon hearing and spotting her boss. "No worries Vivian." She declared, "I have the matter well in hand."

Vivian sighed as she reached them. She was obviously pregnant and the speed at which she had moved had clearly tasked her.

Will motioned and his maids sprang into action. Rita stepped up beside her and offered her an arm while Sarah dragged a nearby chair over. They both helped her down into it as the clerk watched with a faltering expression. This obviously wasn't going how she expected it to. With a shake of her head she reached for the phone.

"Put down the phone!" Vivian snapped. "You have already caused enough damage."

The clerk gaped at her but set the phone down. "I was just getting rid of these disreputable people." she defended herself. "Since they wouldn't leave I was calling security."

Vivian just sighed and sank her head into her hands. After several deep breathes she looked back up, "Security can't throw out the owner Trish."

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Trish was extremely pale as she pleaded her case with Vivian in the back room. "I didn't know he was the owner!" She nearly shouted. "He just showed up, with those two bimbos!"

Vivian snorted a laugh. "Those bimbos, as you call them, make more money than you ever will."

Trish gaped at her "Your kidding?"

"No. I have heard their salaries are seven figures."

Trish was at a total loss at that. "Then why dress like that?"

Vivian laughed "Really? You wouldn't wear something like that for a million dollars a year?" She paused thoughtfully, "Though I'm sure some do it for the lifestyle and others for the thrill" She focused back on her young employee. "Now you are going to do what ever you have to, to get back in their good graces or you will never work in this town again."

"You can't threaten me!" Trish snapped

Vivian shook her head "I'm not. It's a warning not to anger them."

"So he owns this shop. That doesn't mean I cant work elsewhere."

Vivian held up a hand to stop her "I think you misunderstood something."

"Oh?"

Vivian nodded "He doesn't just own this store but the entire mall and everything in it." Trish gaped at her and opened her mouth. Vivian continued, "His family owns this city. If you anger them you will have to move and hope they don't pursue you beyond here."

Trish slumped down into one of the chairs looking beaten and exhausted.

Vivian levered herself to her feet and moved over to lay a hand on her shoulder. "Just go out there and serve them like they are royalty and ask for forgiveness." She paused, "That is a very nice young man and I imagine his maids are of similar disposition. Who knows you may even get a job offer."

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"I would like to apologize for my earlier behavior." Trish stated trying to keep her voice even "I judged you based on appearance and I shouldn't have." She kept her head bowed waiting for a response.

"His clothes probably cost more than you make in a year." One customer muttered rather loudly.

Will ignored the spectators and gently lifted her chin "I accept your apology." He motioned to the girls "But they are the ones you have to appease."

Trish's eyes grew wide as she spotted Sarah's sly grin.

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"Come on out!" Sarah called, "We are waiting."

'That's the problem.' Trish grumbled to herself. Taking a deep breath she steeled herself before stepping out of the change room. All the chairs in the store had been gathered into a semi circle that faced the change room exit. When she came out everyone was waiting. To her humiliation, that included all the customers that had been in the store.

They cheered and cat called when she stepped into view. Her blush grew as she stumbled to a stop. She was dressed in nothing but a set of the stores best lingerie. Stockings, thong and corset in a deep magenta were paired with lacy matching gloves. She had never displayed her body like this before. While in good shape she didn't like being on display. Remembering Vivian's warning, she swallowed her fear and strode forward.

When she reached the center Sarah gave a twirl motion. Pinning a smile in place she did as indicated. She checked for approval and found Sarah motioning again but slower this time. Hiding her irritation she did as indicated once more.

"Well, what does everyone think?" Sarah asked.

The responses were all yelled out simultaneously but the overall theme seemed to be disappointment. Not in the clothes but in the presentation. The other maid came gliding back into the shop as the discussion continued. She had a shoe box tucked under her arm.

"Help her out girls," Will ordered, reclining with a smile.

The maids both leapt to obey. They quickly guided Trish back out of sight as they all got ready. Before anyone had time to be bored they were back. All three glided out in nothing but lingerie. The maids wore very similar outfits to Trish's varying only in color and cut of their panties. Sarah wore white and pale pink while Rita had a pale teal. The three of them moved together, stopped and spun in sync. They had obviously practised out of sight.

Trish now wore towering heels that matched the maids. She moved only slightly less gracefully than them and seemed quite comfortable in them. Now that she wasn't alone she slowly began to enjoy herself. The three of them slowly performed a fashion show for everyone.

The crowd began to cheer and clap with each new outfit. The crowd grew quickly as others were attracted by the noise. Vivian soon found herself frantically trying to fill orders. Men liked what they saw and bought gifts for their partners, while women wanted to surprise their partners.

When they had displayed the last outfit the three strode out to help Vivian. She was swamped and was grateful for the help. Will slowly moved through the shop helping out where he could but generally just keeping an eye on things.

Trish had gotten over her embarrassment and was flying around the store in her lingerie filling orders. The two maids assisted her, laughing and smiling as they did so.

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