Sissy Maid Son Pt. 03

Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18.

*****

Peter stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mother would have them. Rachel noticed her maid was taken-aback by this, she loved making Peter uncomfortable. It's why she always wears low-cut tops around the house. Watching him try not to stare at her was intently gratifying.

"Put those on now, maid. I know you can walk in them. I have evidence," Rachel said with a wink.

"Yes...mother."

Peter walked into the living room and sat on the couch. Rachel pinched his butt as he walked past her but he tried to ignore it. He put both stilettos on and to his surprise they fit him perfectly, but they've obviously been used extensively. Rachel walked into the room to watch her maid walk in high-heels. She's seen Peter walk in heels before in her videos of him masturbating in her lingerie, but nothing as tall as these shoes.

"Oh my, you naughty girl. Did you forget your headband? Go back upstairs. It should be in the box."

"Yes...mother," Peter said meekly. He shuddered being called a girl but he heard the aggressive tone in her voice and didn't want to incur any punishment.

Peter stood up, his balance off considerably. She saw him wobble with his first few steps, savoring his humiliation until he got accustomed to wearing them. Peter was focused on his steps when he passed his mother, his stocking-clad feet carefully choosing their steps.

"Wait," Rachel ordered.

Peter stops in his tracks about six feet from his mother. She reached up under her dress and pulled her blue lacy panties down to heels and stepped out of them. She threw them at Peter whose eyes widen witnessing the event.

"Get me new panties. Those are wet."

"Yes, mother," Peter nodded.

Peter turned back around and proceeded to the stairs. His hands delicately carrying the wet panties. He knew why her panties were wet but tried not to think about it as he avoided touching the wet spots.

He approached the stairs and ascended slowly while Rachel stood at the bottom, eager to view under his maid's dress. Peter was careful to take one step at a time, he felt her staring at him as he climbed up but his hands were busy maintaining his balance to stop someone from gazing up his dress.

He slowly made his way to his mother's room and threw the panties into the laundry hamper and picked out a new pair of panties from the drawer.

It took him some digging through the box of lingerie, but he found the headband. It was a typical French maid headband with a white, lace trim. He adjusted his headband in the mirror and took a moment to look at his reflection. He still couldn't believe that his mother would force him to serve as a maid. Just yesterday their relationship was of a normal mother and son, but now he was wearing a short French maid dress, stockings, his brother's old high heels, and a headband.

He made a final adjustment to his new headband and stared at himself in the mirror. His dress was short, especially with the petticoat, and ended at his freshly shaved thighs. His garter straps were clearly visible and matched his stockings.

"Maid!" Peter heard his mother yell.

He wobbled back downstairs and saw his mother sitting impatiently in the living room. He made his way to Rachel, who had her legs and arms crossed.

"Yes, mother."

"Curtsy. My maid will curtsy when she is called," she demanded.

Peter resented being called "she" again but didn't feel he had the strength to fight back. He attempted to curtsy but Rachel was visibly disappointed by his performance but she said it was good enough for now. She also warned him that there will be consequences if he disobeyed his maid protocol or uniform requirements again.

"I want you to start preparing the table and dinner for my guests. They'll be here in a little over an hour. And I want you to answer the door to greet them inside."

Peter didn't realize he would be in front of other people. He stood there with his hands fiddling with his skirt, staring at his heels thinking of what he could say. He didn't want to humiliate himself further by being seen by other people while dressed as a sissy maid.

"Do you have something for me?"

Peter realized he was still holding the fresh pair of panties for his mother. He handed them to her, staring at the ground.

"Thank you, my maid." She stood up and slid her panties up her dress knowing Peter was watching.

"Now," she slapped Peter's ass, "go to the kitchen and prepare for my dinner."

Peter rushed past the dining room and into the kitchen. He's gotten used to the high heels fairly quickly and didn't want to anger his mother. Rachel watched her maid mince to the kitchen and saw his dress bounce as he rushed to the kitchen and it filled her with perverted delight.

Peter's heels clicked with the kitchen's tiles as he walked to the center counter. He felt his chest compress with anguish as he held back his tears. He knew that if his mother heard him cry again she would make him regret it further. As he stood over the counter, he saw the only thing on the marble counter-top was a handwritten note by his mother. It outlined his maid protocol for the evening as well as the recipe for dinner and dessert.

Peter got to work preparing the meal with the recipe laid out for him. His heels clicked on the tiles as he would move around the kitchen, all-the-while being cautious not to make a mistake cooking. Rachel would occasionally check on him, one time she saw him open a lower draw and she saw his panties as he bent over. She saw that Peter had an erection under his panties which pleased her immensely. She was pleased that her new maid would take his servitude seriously on some level, and she knew she had him in her palms.

Before the guests were due to arrive she checked in on Peter again, she enjoyed instilling discipline into him. And she found it intensely gratifying watching her son in a short, daint maid dress work as a maid.

"My guests will be here soon. If you break any of the rules I laid out for you. You will be punished," she said sternly.

"Yes, mother," Peter said meekly.

Rachel perked up an eyebrow, "Are you forgetting something?"

Peter fumbled and curtsied in a panicked fashion hoping not to incur punishment. She lifted his chin.

"Hmm, if you don't want all your friends and the rest of the world to see you jacking off like a little sissy bitch I suggest you remember your place," she said, finishing off with a kiss on his lips.

She glided her hand down his dress and to his crotch. She then reached under it and felt his lace panties and his hard penis. She could feel that the top half of his penis was sticking out of his panties. She knew he would still be excited wearing panties around the house. Peter just stood there letting his mother grope him at her pleasure.

Peter managed to set the table and almost finished preparing dinner, so Rachel figured there was time for her to enjoy her new maid for a few minutes.

"Oh. That must be the guests arriving. Sissy, welcome them in," Rachel said as she sat on the couch.

"Yes, ma'am," Peter said with a curtsy.

Peter walked to the door, trying to remember his mother's instructions for welcoming guests. He dare not disappoint her in fear of punishment, or his mother releasing the blackmail she has on him. But all that would be far from his mind.

Peter made minor adjustments to his short dress and hair before opening the door, seeing three familiar ladies standing there each with wide smiles on their faces. The lady on the left was Peter's English teacher Ms. Smith, the one in the middle was his neighbor, Samantha Kingston, and the one on the right was his mother's sister, Aunt Mary.

He was taken aback by them and felt humiliated standing in front of them wearing such a revealing costume with stocking and lingerie. The ladies giggled their hellos to him.

"Welcome to Madam Rachel's home, please make your self at home," Peter said with his head tilted in shame and with a curtsy. He was deeply uncomfortable wearing such a lewd costume while playing the role of his own mother's maid in front of women he knew.

The ladies giggled at the sight and they all thanked the maid. Aunt Mary even kissed Peter on the cheek and said he looked like a pretty maid.

Peter then followed what he remembered from the instructions and escorted them to the dining room, taking their coats and bags, and curtsied when appropriate. They all giggled and chatted amongst themselves, saying what a good maid he is and how sexy he looked.

His neighbor, Samantha, took note of how well-trained he seemed and was impressed by how fast Rachel broke him into an obedient servant.

Peter led them to the dining room where Rachel was already seated. They all exchanged pleasantries and Rachel excused Peter back to the kitchen to finish preparing dinner. Their conversation largely stayed on Peter and how surprised they are on his progress. Rachel even welcomed to ladies to grope her new maid as much they liked, which they all, of course, accepted the invitation.

The time came for dinner to be served, and Rachel rang a bell that cued for Peter to roll out a cart with all the guest's plates ready to be served. He tried not to react to the ladies pinching and grazing his legs as he served their food and wine. Aunt Mary pinched him so hard that he feared he had to adjust his stockings, whereas Ms. Smith simply grazed his upper leg gently just under his panties. He wanted to pull away from their advances, but his mother's note clearly laid out that he wasn't allowed to refuse anyone touching him.

When dinner was served, Peter was thanked by the guests and his mother ordered him to stand in the corner with a tray of fresh wine glasses. The evening carried on with Peter occasionally trading the ladies' glasses and each time he was subjected to a pinch or rub. Both Aunt Mary and Samantha grabbed his penis over his panties, and they both noticed he was hard. And both times Peter had a surprised look that his mother caught. She was glad that the ladies were enjoying her new maid almost as much as she was.

Peter was ordered to collect empty plates and glasses while the ladies retired to the living room while he finished washing up. The ladies continued discussing Peter, and Ms. Smith tells anecdotes about how she would catch Peter looking at her skirt in class and Samantha mentions how she would like to see Peter clean her own house. Aunt Mary confesses that she was surprised that Peter was just as hard as he was in Rachel's videos.

"Well he is a sissy, like his brother," Rachel admitted.

"How is little Bella anyway," Aunt Mary asked.

"Still working at the restaurant. But his wife will be taking over soon so he can focus on domestic service."

After more chatting and more drinks served obediently by Peter, Mary wanted a particular request fulfilled from the maid. She entered the kitchen where Peter was still cleaning up.

"Come here, Peter," she ordered softly.

He approached her obediently with his hands folded over the dress's apron and head tilted down. Remembering his mother's instructions, he addressed her accordingly.

"Yes, ma'am?"

"I brought some old clothes that you can have. Be a dear and fetch the bags from my car."

His face turned red. Going outside in his maid uniform was the most humiliating thing he heard all day. His mother said to not be such a pansy and just go out. It was dark after all and she reasoned who would be out at this hour?

He collected the bags and placed them in the laundry for him to wash later. There was a breeze outside so keeping his skirt down was the challenge but luckily he thought no one saw him out. The night carried on with Peter cleaning and serving the ladies. Soon the guests decided to leave, but not without each one thanking the "very attentive" maid. Each guest insisted on hugging Peter with all of them giving him a kiss on the cheek and a pinch on the butt. Peter didn't care, his feet were killing him and his panties were not giving him any room. He just wanted to go to bed and not think about any of this.

After he was finished cleaning up after the party, his mother gave his permission to change into the silk nightie and matching panties in the box. He knew the one, it was black and lacy, he remembered that it's comfortable so it should be fine to sleep in.

"You did we tonight, I'm glad I'm not the one who has to clean up," she giggled.

Peter was going to reply but his mother cut him with how he had to shower and head to bed. The nightie felt nice on his drying skin and his bed soothed his ankles and he fell asleep almost immediately. Rachel found him deeply in sleep, kissed him on the lips, shoving her tongue into his mouth. And looked forward to playing with him for as long as he could take.