Help Wanted Pt. 02

Brianna made her way down the hallway, struggling to get accustomed to her new attire. As she walked, she shuddered a bit as the ruffle on her dress brushed against her legs. Sure, Brianna had dressed up as a woman, but never in such a sexy outfit. She tried to imitate the sultry, feminine gait she had seen Allison perform earlier when she first arrived. Brianna was still uncomfortable with wearing heels, she had never worn them for a whole day, let alone every day. She wobbled a bit at times, hoping Mistress wasn't watching. After all, she didn't want to make a bad impression on her first day. As she approached the stairs, she saw herself in the mirror on the opposite wall, a stunning maid with long black hair. For a moment, she was unable to reconcile that the image in the mirror was her, and was made aware of the chastity device. Her penis, or clitty as Mistress insisted it was called, began to throb against its plastic prison. The realization that the sexy maid in the mirror was her only made it throb harder. Brianna winced at the discomfort and attempted to get those thoughts out of her mind. She desperately wanted to masturbate after seeing the image in the mirror, and wondered if she would ever get released and be allowed to do so. After admiring herself in the mirror, she walked down the stairs, hoping whatever training Allison had in store would keep her distracted.

Brianna made her way to the kitchen, and saw Allison over a stove stirring a large pot.

"You're late" Allison said, her gaze not moving from the pot. She put the spoon down and walked over to Brianna, still standing in the doorway.

"Well well, you do look cute. I almost can't recognize the shabby man I let in the door this morning, who couldn't seem to keep his eyes off my ass." Allison mockingly said, inspecting Brianna's appearance.

"So why were you late, were you staring at yourself? Hm? If I lift up your skirt, will I see your clitty all excited?" Allison said, reaching for Brianna's skirt. She lifted up the skirt and pulled down Brianna's panties, revealing her still throbbing clitty.

"Just as I thought." said Allison, letting go of the skirt. "Put yourself back together."

Brianna pulled up her panties, and smoothed out the skirt in front of her.

"By the way maid, you are to always respond to me if I ask you a question. Am I understood?' said Allison, staring sternly at Brianna.

"Yes." Brianna meekly replied.

"Yes Miss" Allison interrupted. "I am Mistress' head maid and until your training is complete, you will give me every courtesy you will give to Mistress. Since I am not your Mistress, you will call me Miss. Am I understood?"

"Yes Miss Allison" Brianna said, sheepishly looking down at her dress.

"Good girl. Maids should always keep meek and subservient body language around their superiors, keep that in mind and you'll do well." Allison stated, still eyeing her new charge. "We get dozens of new maids, most of them fulfill their fantasies and leave, they don't have the discipline required to live the lifestyle they crave. Are you one of them, maid Brianna?"

"...I don't know, but I plan to do this job as best I can, Miss." Brianna meekly replied.

"We'll see. I need some vegetables chopped for tonight's entree, they're in a bowl over there on the counter, they need to be diced." Allison stated, pointing to the counter opposite the stove. "Start chopping and call me when you're done to check your work. Don't forget to maintain proper posture and cleanliness."

Brianna turned to begin her task but was interrupted by the Allison loudly clearing her throat.

"Not so fast girl, when a superior in this house gives you a command, you must politely acknowledge the command and curtsey before leaving their presence." Allison stated, staring expectantly at Brianna.

Brianna had vaguely seen this done in old movies on TV, so she did her best to approximate.

"Yes Miss Allison" said Brianna. She then crossed her legs and bent down, but nearly lost her balance and had to catch herself grabbing the counter top to not fall.

Allison belted out laughing. "You call yourself a maid and you can't even do a proper curtsey? You're even more pathetic than I thought." she scolded. Brianna was surprised by how ashamed this made her feel.

Allison regained her composure. "OK maid, go do your task." she said. Brianna turned and got to work, she washed her hands and walked toward the counter to start cutting the vegetables. Allison interrupted her several times to correct her posture, pushing in her back or making her straighten out her legs. She slowly began trying to keep poised on her own, legs together and bending only at the waist as needed. She noticed that as she did this, the pose only served to force her breasts and butt out for a better view, but it made the work much more difficult. Brianna just assumed that was intentional. After each vegetable was diced and put into the bowl, Brianna called Allison over to check her work.

"Miss Allison, I'm finished and ready for you to check my work" Brianna said. As she turned around, Allison made her way over to check Brianna's work. Allison took a spoon and stirred the bowl, examining it with each turn.

"Well it's not as bad as I expected. You may be trainable after all. Pour these into that large casserole next to the stove and I'll give you more tasks." Allison said, turning back toward the stove.

Brianna helped Allison make the rest of the meal, caesar salads to start and a main course of beef roast with potatoes and a corn casserole. They loaded the first course onto a cart, and Brianna followed Allison to the dining room.

"Now Brianna, once the food is on the table, you and I will stand by the door and wait for the guests to enter the dining room." Allison said, motioning Brianna to the other side of the door. "Keep your eyes down, no one wants to be stared at by the help. When guests are seated, you and I will serve each starting with Mistress' seat at the head of the table, and then working down the table to the other end. I will serve the food and you will offer each guest a glass of wine starting with Mistress. Is that understood?"

"Yes Miss Allison" Brianna said.

Allison turned toward Brianna "Now, when you serve each person, you must curtsey and offer them food or drink like this."

Allison lightly pinched each side of her skirt with her fingertips, crossed her feet behind her and slowly dipped her head, pointing her eyes at the floor the whole time. She then said politely "May I serve you a glass of wine Miss?"

"Obviously you must refer to Mistress by her title, the rest are Sir or Miss. Now you try, offer me a glass of wine. Try and do a better curtsey than hat horrid thing you did earlier in the kitchen." Allison commanded, regaining her composure.

Brianna pinched each side of her skirt as Allison had, and crossed her legs. This was much more coordination than she was used to, and she nearly tripped herself. She dipped her legs and said "May I serve you a glass of wine Miss?"

Allison stared emotionlessly for a moment, and finally said "That was not very good, you better practice and make sure you don't fall down. Maids who fail to curtsey properly get punished." She smirked a bit at the mention of punishment.

Brianna winced at this, she had already been told she would receive a punishment from Mistress earlier, and she couldn't help but wonder what that might be. Surely as a legitimate employee it couldn't be too harsh right? There are laws for this after all. Rather than dwell on it, she turned back to push the cart to the table. There were only three seats to be set, two guests on either side of Mistress. Allison showed Brianna how to place the tableware, and Brianna placed a salad at each seat. They then both assumed their positions next to the door.

After what felt like an eternity, Mistress and her guests entered the room, accompanied by a man and a woman. Brianna quickly peeked at the doorway for a look and quickly averted her eyes to the floor, hoping she wasn't seen. Allison walked toward the table and motioned for her to follow. Once Mistress and her guests were seated, Allison discretely motioned for Brianna to begin serving. Brianna stood in front of Mistress, once again pinching the hem of her skirt and bowing her legs. She was relieved to not stumble this time, and offered Mistress her wine.

"Would you like a glass of wine Mistress?" Brianna meekly asked, remembering to bow her head.

"Good girl! You pick up quickly. Yes please, I would love one." Mistress excitedly replied.

Brianna poured Mistress a glass, and placed it in the proper position on the table. She then did the same with each guest. The man to Mistress' right was a very attractive younger man, he had a chiseled jaw, dark hair and a moderately muscular build. He eyed Brianna over in a way she wasn't used to, staring at her ample fake cleavage. Being unaccustomed to this kind of attention, Brianna blushed and quickly served him his wine. As she did so, the thought of being desired as such made her clitty struggle within its bounds. Brianna was confused by how this attention from a man made her feel, as she had always considered herself straight. She longed to touch it somehow, if only she could release it from its plastic prison.

Next she served the woman to Mistress' left, a similarly attractive younger lady with an athletic build and voluptuous features. Her long red hair flowed down into a drape over her shoulders and cleavage. It took all of her restraint to perform her curtsey while her clit continued to struggle. She could feel the front area of her panties begin to get wet, the only release allowed to her. She accomplished her task, and followed Allison to wait for orders.

"So Anne, I see you have a new girl." said the lady

"Any chance I'll be seeing her soon?" She coyly asked. Brianna became filled with dread at what other demeaning acts might be awaiting her. She heard Mistress reply

"Perhaps, I do owe her a punishment" Mistress said playfully. Brianne panicked. This was only supposed to be a simple job, and now they want to do possibly horrible things to her? Brianne's thoughts were burst when she heard a little bell.

"Maid Brianna, please serve Kayla here some more wine." Mistress called out. Brianne did as she was told, trying as hard as she could to focus on the task.

The rest of lunch proceeded quietly, with Brianna and Allison periodically serving more drinks and food. After they had served desert, the crowd lingered for a bit chatting. Brianne tried to eavesdrop but concentrating was difficult as her feet began to hurt the longer she stood. It felt like it had been hours and she was wearing heels that were quite a bit taller than she was accustomed to wearing. To Brianna's relief, the group finally stood up and began to leave the room. Brianna saw Allison curtsy so she did as well.

"Brianna, once you're finished helping Allison with the dishes, please meet me in the parlor." Mistress ordered, as she walked out of the room. Her racing thoughts were once again interrupted, this time by Allison's stern voice.

"Wake up girl, you're here to do a job. Fetch the serving cart so we can collect the plates." Allison scolded. Brianna pulled up the plates and began assisting Allison with clearing the table. Allison continued to attempt to correct her posture, and Brianna tried her best to follow as she was told. When the two maids had cleared and cleaned the table, they retreated to the kitchen to do the dishes.

"Now, Brianna, you don't want to get that pretty uniform all dirty, do to the closet and grab a thicker apron." Allison stated, pointing at a cabinet in the corner.

Brianna once again did a curtsey, this time picking up each side of her dress, and bobbing down with her knees without falling, meekly saying "Yes Miss Allison."

As she looked up, Allison had a smirk on her face.

"I'm glad to see you learning girl, there may be hope for you yet." She said sweetly, a noticeable deviation from her usual demeanor. Brianna walked to the closet and grabbed one of the aprons hanging to the side. It was just as frilly as the one for her uniform, but made of a thicker material and covering more of her dress. It featured large ruffles on the shoulder straps and wide ties which she carefully tied into a bow. Brianna smirked a bit, amused that just yesterday she would have never worn such a thing around other people. She returned to the sink, Allison had her scrub while she dried the dishes and put them away.

"Mistress prefers us to do this by hand, her dish-ware is very fine would be ruined in a machine." Allison stated. "She also likes to have menial tasks for us to do, Mistress believes that menial labor helps build discipline."

Allison then turned to Brianna and smiled, playfully stating "But she also does it to put us on better display for the guests."

Brianna winced at this, she was still not comfortable being seen in this very feminine attire.

"Not to worry, you'll get used to it." Allison said, almost sounding affectionate.

"I am hard on you because I want you to succeed, but I really do believe Mistress did the right thing, I knew when I opened the door and saw you that you belonged here." Allison said. Brianna blushed slightly.

"How did you know?" She replied.

Allison paused for a bit. "Did Mistress tell you... about me?" she asked.

"She said you used to be a man when you came to her" Brianna blurted out.

Allison let out another loud laugh. "I suppose back then I was, technically. But I was never good at it." She said. "Tell me, have you ever felt like you were incapable of living up to society's expectations of you, like you were expected to play a game you didn't have the rulebook for?

Brianna thought for a bit. She HAD felt that before, for much of her life she was ridiculed and called names. She had been picked on in class and called a girl or a faggot for things she seemingly had no control over.

Allison interrupted her introspection. "I can tell by the look on your face that the answer is yes, I see it in your eyes now just as I saw it then. Tell me girl, were you wearing panties under your male clothes when you arrived at the house?" she asked.

Brianna, surprised, stuttered out "actually... yeah. Did Mistress tell you that?"

Allison chuckled. "Oh no dear, I could tell just by looking at you that you were one of us." she said.

Brianna blushed a bit. "Us? How many formerly male maids does Mistress employ?" she replied

Allison paused for a moment. "Including you, I suppose we have 4 now. I believe you met Stephanie earlier, she's just finished her training period and become a full maid." Allison said.

"Stephanie and I started around the same time with another girl named Lilly. You will likely not meet Lilly for a while, she was quite rude to Mistress in front of her guests and is being punished."

Brianna was shocked at this, but Allison seemed to sense her unease.

"Not to worry." said Allison "Lilly is very naughty, you need to do a lot of things on purpose to warrant the kind of punishment she's getting."

"What is her punishment? And can she not just leave?" Brianna asked.

"Oh yes, we aren't slaves here. Well, we kind of are but not in the 'you can never leave' way " Allison said, smirking a bit.

"Lilly was given one last chance, and it meant being set off for special training from one of Mistress' very strict friends. Her name is Miss Grace, and don't you ever forget the 'Miss' with her, as Mistress allows her to punish us." Allison explained.

"Okay hold up" Brianna exclaimed. "What did you mean about kind of being slaves?"

Allison giggled. She quickly pulled up Brianna's skirt and grabbed her caged package. Brianna jumped at the touch.

"Slaves in this way silly. If you told Mistress you want to leave, she would stop all of this and send you on your way." Allison said.

"And-" Allison licked her fingers, "mmm"

"Judging by this, I think you like being this kind of slave." Allison said, licking her lips.

Brianna blushed. She had never been very intimate with anyone, and now this woman was now being so forward with her? Or was she still a man? For that matter, was Brianna still a man? This was becoming a lot to take in, she had long since stopped washing dishes. She was snapped back to reality when Allison gave her a big hug.

"Aww I'm sorry, I shouldn't have been so forward." she softly said into Brianna's shoulder.

"It's been a while since we had a new girl to play with, particularly one as well suited to this lifestyle as you are." Allison said.

Brianna blushed. "It's okay Allison, this is just a lot to get used to. Just yesterday I was a normal man, and now here I am becoming, um, whatever we are." she said.

"And, I've never been touched by a beautiful girl before." Brianna said softly.

A huge grin appeared on Allison's face. "Aww, you're cute. Come on, let's finish those dishes. Maybe if we have free time we can hang out later." she said.

Brianna and Allison finished the dishes without event. Brianna removed the apron and put it back in the closet, and Allison led her down the hall to the parlor. She stopped before opening the door.

"Now Brianna, when presenting yourself to Mistress or any of her guests upon being summoned, be sure to curtsey like I showed you and politely announce yourself. Do not say anything else unless spoken to. Understand?"

Brianna playfully did a curtsey and said "Yes Miss Allison"

Allison smiled with glee. "Oh yess you will do fine. One more thing, before presenting yourself to Mistress, you must make certain you look over your dress to check that everything is laying flat with no folds or creases." Allison said. She then demonstrated to Brianna how to smooth her dress. Brianna quite liked this exercise, the feeling of her hands running down the soft satin, feeling the "poof" of the petticoat flaring her skirt away from her admittedly meager hips. Allison giggled watching this, fully aware at the pleasure Brianna took from her new clothes.

"Okay prissy girl, I think that's enough. Now, I believe Mistress is waiting." Allison said.

Brianna walked up to the glass french doors to the parlor, making sure to close them quietly after entering. She curtseyed as best she could, and said "Hello Mistress, I am here as you requested."

Mistress Anne was seated in the same chair from when they first met, she put down the book she was reading.

"Hello Brianna, I see Allison has been teaching you to curtsey, that was very good." said Mistress.

"Had you ever done a curtsey before today?" She asked.

"No Mistress, but I had seen one done on TV." Brianna meekly replied.

Mistress stood up and approached Brianna. She began eying her new creation, seemingly searching for flaws.

"Brianna I must admit, you did a wonderful job at dinner for someone who had never waited tables, not to mention how quickly you have taken to your new attire" Mistress said.

Brianna blushed. Unsure of what to do, she curtseyed again and said "Thank you Mistress"

"Before we start, there is one thing we must get out of the way" Mistress said, walking to the door and closing a curtain over the glass.

"Please follow me." Mistress commanded, walking to an armed diningchair and placing it in the center of the room. She then went to the desk in the corner, pulling out what Brianna recognized as a pink rubber ball gag. Mistress strapped the gag around Brianna's head and sat down on the chair.

"Now, Brianna, I want you to bend over my knee face first." Mistress commanded. Brianna had a sinking notion of what Mistress was planning to do to her. She complied, and bent over with her hands on the arm of the chair, butt in the air topped with her fluffy petticoats. Mistress pulled back the skirts and pulled her panties down to her knees. Between her legs dangled her plastic encased clit.