My Father, The Maid

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Oliver learns about his Father and his new wife's relation.
4.8k words
4.27
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Part 1 of the 3 part series

Updated 06/09/2023
Created 10/12/2018
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SissyOona
SissyOona
35 Followers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowadays I rarely if ever saw him, once a year for Christmas at most, and maybe a text on my birthday. All that being considered it was really weird when Claire, my step mother, texted me inviting me over. As bizarre as it seemed I had nothing better going on, so I decided to make the hour and a half trip to see them.

On the drive to their house I thought about my dad a lot, about growing up with him, how he treated me, how he treated my mom, how when he was in a good mood he could be a great guy and a wonderful father, and how much more often when he was in a bad mood he was a complete and utter asshole. My father was an ambitious man even though he came from a difficult background. When he was in high school his parents pressured him to drop out to help his father with his carpentry business, but he refused to give up on his education. Instead he found time for both, school during the day, carpentry at night. He eventually graduated high school and started taking classes at the local community college. That was when his mother took ill, the medical bills became too much and he couldn't continue on to a university. He started working full time with his father, soon he started growing the business from a small father son operation to a moderate sized construction company. At about that time he married my mother, they had both met in college and thought they were madly in love with each other, I was conceived on their wedding night. As I was growing up the company continued to grow, slowly my father was able to go from doing actual construction to being more of a manager and boss, work that he was admittedly not great at. The work was hard on him and he would often come home in a bad mood, he yelled at my mother a lot, he ignored me just as much. Things got worse before they got better, he came home drunk often, he beat my mother on several occasions, he even hit me a few times. I am thankful that my mother was able to leave him and get both of us out of there. I was 8 when they separated, I'm 24 now. It has taken a long time, but I have forgiven him, he has apologized for his actions, and I'm not one to hold a grudge.

Then there's his new wife, Claire, they married 5 years after my parents divorced. I never had any reason to dislike her, she always tried her hardest to be a good host to me whenever I came over to visit my father. She was an attractive woman, a few years younger than my father. They met while my father's company was building a large office complex for Claire's husband at the time, an older man who was moderately rich. They started having an affair behind the old man's back until he died suddenly later that year of cancer. Upon the man's death she was expecting to get all of his money, however he had made up a will when he was diagnosed leaving everything to their daughter Aimee. As far as I could tell my father was happy with Claire and a better father to Aimee than he had ever been to me.

Soon enough I pulled into the driveway. I was somewhat confused because my father's car was there, it was Friday at 2:30, he was usually never home before 6pm. I thought little else of it and figured maybe he had bought a new car or something. I walked up the path to the door and rang the bell, it took longer than I thought it would for someone to come to the door, but I thought nothing else of it. As the door opened standing before me was my stepmother Claire, she was beautiful, about 5'8", slim, with large round breasts held in place by a white lace bra which was clearly visible through her thin white button down blouse. Her gorgeous long legs were encased in somewhat transparent black stockings, which you could see the lace tops of peeking out of the bottom of her tight black pencil skirt which ended just above her knees. Her face was perfectly made up, not that she needed it, and she had a full head of long black hair that was fixed into a long ponytail. If someone were to tell you she was a model in her youth I doubt anyone would have any reason to not believe that statement. She very kindly invited me in saying we could sit in the kitchen for a late lunch if I was hungry, having not eaten anything since that morning I gladly obliged.

As we sat in the kitchen I asked if my father had bought a new car, seeing as he usually isn't home at this hour, Claire replied "No, he's here, he's just a bit busy at the moment, he'll be along shortly. That reminds me, I am sorry it took so long to answer the door, your father was supposed to answer it, but he was unwilling to separate himself from what he was doing."

"Oh, is he working from home now?" I asked.

"In a manner of speaking I suppose you could say that." She said with a bit of a smirk. "You will see soon enough."

"Okay" I said, obviously confused. After a pause I finally remember to ask, "so what was that text all about, I know I'm not around often, but it seemed kinda out of the blue."

"You will see soon enough, let's just say it has to do with the 'work from home' your father has been doing."

There was a moment of silence while I tried to figure out what she could mean by that, but the quiet was broken when she suddenly said, "you wanted lunch didn't you? To be honest I could use a bite myself. Shall I have the maid serve us?"

"Sure, I could definitely use some something to eat." As I said this she rang a little bell she had. "Wow, I didn't know you guys had a maid, dad's business must be doing we--." My sentence was instantly stopped as the kitchen door opened and my father entered.

There he stood eyes cast to the floor, I almost didn't recognize him and honestly probably wouldn't have if he wasn't my own father. He was wearing a stereotypical french maid dress that was shorter than any dress I had ever seen a woman wear, the hem resting high on his thighs. His hairless legs were covered by black fishnet stockings, on the top of which you could see shiny silver clips hiding under his skirt. On his feet were a pair of high heels, I'd say 5 or 6 inches at least, which had little padlocks holding them on around the ankles. Sitting atop his head was a crop of long blonde hair, which I could only assume was a wig as my father had always had short black hair. His face had makeup applied to it making him look all the more feminine, it wasn't extreme like a drag queen or something like that, you can tell whoever did him up like this wanted him to look like a woman and not some exaggeration, which was not suggested by his clothing. And the final symbol of his new found femininity were two large round breasts pushing forth the frills on the front of his dress.

I stared in awe and confusion as my father, dressed as a maid walked into the room and curtsied before my step mother and then me and asked if we needed anything. My stepmother said "yes, your son and I would like some lunch."

"Yes Miss, what would you like?" He asked meekly.

"A ham sandwich should suffice, I will expect you to start dinner soon." she said.

"And you Oliver?" He said turning toward me.

Before I could answer my stepmother said, "excuse me sissy, is that any way to address someone superior to you?"

"No Miss, sorry Miss" he said while giving her a deep curtsy. " My apologies Mister Oliver. What can I make you for lunch?"

Still in shock to everything I have just seen I somehow stammer out, "yeah... ham sandwich." To which my father curtsied and got to work.

There was a silence as my father got to work making lunch that seemed to go on forever, but in my shocked state I had no concept of time. Finally Claire broke it by saying, "I can see you are confused, and I understand that. You see your father is now what is called a sissy maid, he dresses in frilly girly dresses and does what he is told. He is dressed in this way at all times he is at home and on occasion outside as well. He has a strict set of rules he must follow at all times, which I can go into later. If he fails to follow any of these rules he will face punishment, this you will see later as he has already earned punishment twice today, once for not addressing you properly, and once for not greeting you at the door as I told him to. Any questions?"

As she said all this my head was reeling, I could barely comprehend what she was saying. I couldn't believe that my father was going through with all this. I was snapped back to reality by her question. "Yeah... I have tons... but I can't think straight right now." I babbled out in response.

"You must be hungry, once the maid has finished our lunch we can retire to the living room to eat in private." She said paying my father no mind, as if he wasn't even in the room.

At that time my feminized father set two plates on the table, each with a simple sandwiches on it. As he set them down I noticed his nails were painted a pale girly pink. This caused me to remember an incident that happened when I was 6 or 7 years old. One day I had been playing at our neighbor's house, my parents were having a particularly bad fight so they sent me over there to get away from it. I wasn't thrilled about having to play with a girl, but I couldn't do anything about it. If I remember correctly her name was Emily, and she was about two years older than me, a fact she regularly brought up when we played. On this particular day she decided it would be fun to paint my nails, she picked a light pink similar to the color my father was wearing now. When I got home that day with my nails still painted I remember him going into a rage, screaming about how boys don't wear nail polish and stuff like that. When I think about it that may have been the first time he hit me. How times have changed.

Claire and I grabbed our plates and adjourned to the living room, we ate in silence with the exception of my father in the kitchen performing some of the preliminary steps for dinner. When I had finished my sandwich I rose to take it back to the kitchen, but before I could take a step Claire stopped me and said, "you don't have to do that, that's what we have a maid for." At which point she rang a little bell, the sound of which immediately summoned my father, who walked in the room and curtsied both of us. When he saw the empty plates he took them without a word and returned to the kitchen.

After a moment I turned to my step mother on the other end of the sofa and said, "What's going on here? Why is my dad dressed up like a woman?"

"Finally he speaks" she said with a little smile. "You more than anyone should know how much of an ass your father can be, how bossy and mean he can be. Well I will not stand for this like your mother would. So, after we were married when he started to show his true colors I knew I had to do something to curb his behavior. I read about sissy maids online and knew that was the best way to get him to behave himself. I started simply enough, withholding sex unless he wore panties, he continued to act up, so I went further. I slowly replaced all his boxers with panties, adding bras, stockings, heels, the whole nine yards a little more each time he acted up. When that wasn't working I decided drastic measures were called for so I took a few incriminating pictures and videos just in case. The final nail in the coffin was when I had my lawyer go and rewrite our prenup so I would get everything if he left me. Now I'm sure you're thinking that all that is cruel to your father and that he doesn't deserve all that, but you can go ask him yourself, he likes dressing in girl clothes, sure it took a little convincing at first but he loves it now."

"Does he still work?" I asked.

"Yes, but he isn't in the office as often as he used to be, the company runs itself now and he can do a lot of it from home. Before you ask, no he does not go into the office like that, with the exception of his panties and bras. His secretary knows and checks for me to make sure he doesn't change into boxers or take them off on his way to the office."

"Why are you telling me all this? Why did you invite me over today?"

"Your father told me about how terrible he was to you when you were young, I know you to be a kind young man who does not deserve anything like what you had to go through at his hand. I figured this was a good way for you to get back at him and for me to punish him for his past transgressions. Imagine how embarrassed he must be to be serving his own son as a maid. What I am offering is to bring you in, you can live here and help me train your father, he can be your sissy maid too, this is how you can get him back for every time he hit you or yelled at you for no reason. I understand how weird this all is, and I would understand if you walked out the door and never came back, but I ask that you at least think about it. The maid prepared the guest room for you to stay in tonight, sleep on it and tell me what you are going to do in the morning. Deal?"

I thought about it for a minute, considered everything I had seen and heard since I got here, every moment from my childhood in which he hurt me, I thought about it all and finally said, "I still don't know what to think, but I agree, I will stay tonight and make a decision in the morning."

"Wonderful" she said as she started ringing her bell.

At the sound of the bell ringing my father appeared, curtsied and asked "yes Miss? What do you need of me?"

"Your son will be staying with us tonight, make sure to set a place at the table for him." She then turned to me and said, "since you will be staying is there anything you need out of your car?"

"Yeah, I have a change of clothes out there, I'll go fetch them in a little while."

"Nonsense, that is what we have a maid for. Sissy, go get your son's things out of his car."

"Yes Miss" he said with a bit of defeat in his voice. I watched in amazement as my father perched on his high heeled shoes and in his frilly maid dress walked down the driveway onto the street where I was parked in full view of all his neighbors and any passersby. He gathered the few items of clothing from my car and dutifully walked back up the driveway, as he was about halfway up a car drove by a bit slowly, the man driving opened his window and wolf whistled my sissified father, he turned and gave the man a curtsy as if to thank him. The man started to laugh as he drove off. My father returned to the house with my few items of clothing and very politely asked me "where would you like me to put your things Mister Oliver?"

"Um you can just put them wherever I'll be sleeping I guess." I said.

"Yes Mister Oliver." He said before he minced off down the hall to the guest room.

Things were quiet for a while after that, Claire and I sat in the living room and caught up a bit, she asked what I was up to, I asked about her, it was all in all a pleasant conversation. It reminded me of the last time I had come to visit, my father was at work late, as always, so I was left with Claire to have a rather strained conversation. It was as if I had forgotten my father's predicament for a moment. This was instantly broken by the sound of high heels clicking into the room and my father the maid politely saying, "Miss, dinner is ready if you and Mister Oliver would like to eat." A few hours had passed since lunch, so we happily made our way to the dining room.

Upon walking into the dining room my eye was immediately drawn to the table. There were two places so well set at the table I almost felt like I had just walked in to Downton Abbey. My father, still in full uniform of course was standing in the corner, ready to serve. As we both settled into our seats my father briefly disappears, quickly returning with two salads, which were served to us without a word. As we ate we continued having conversation as if no one was there, we even started talking about my father, oddly enough I found myself speaking about him in the past tense. Salads were eventually cleared and the main course was served, some kind of pasta dish with shrimp and a spicy red sauce. I was surprised by how good it was, in all of my life I had never known my father to be able to cook anything. Being a little bit comfortable with the situation, and quite a bit drunk at this point, I decided to make a comment. "This food is amazing, you have him trained really well" I said with a chuckle.

"Yes, he does well most of the time. He has taken to cooking quite well. You see he has a bit of free time most days, but the activities he may undertake during that time are limited to researching food and recipes, working on his makeup skills by watching youtube tutorials, reading fashion magazines, and learning to sew and make clothes."

"Wow, not how I would expect any man to spend his time." I said between bites.

"Your father is no longer a man darling, he is a sissy maid. In fact it had been paining me all day to refer to her using the male pronouns which I'm sure you will agree no longer fit her. Since all this is new to you I figured I could let it slide for a little while. If you don't mind I will no longer be referring to her as anything except."

"Sure, whatever you say." I said not as uncomfortably as I would have thought.

"I understand if you continue to call her by those words, but if you stay here long I will have to ask that you eventually do refer to her as such." She said sternly.

I didn't reply to that for whatever reason, I just continued eating.

As we finished dinner my stepmother rose from her place and said without looking at my father, "sissy, you may clear the table and have your meal in the kitchen, I will give you one hour to complete this. Once you are finished you will join us in the living room for your evening punishment."

"Yes Miss." He replied and got to work clearing the table.

The next hour was quiet, Claire and I sat in the living room once again watching some random movie on the television. Eventually my father walked into the room and stood in the corner. I watched as Claire looked at her watch and turned off the television. As she did my father walked to the center of the room, kneeled before us, and said "Mistress I have been a bad sissy please punish me for my mistakes" as if reading from a script.

"Good girl, before we get to your punishment tonight there is something else you need to do first. I think it is time you gave your son his gift," she said with a sly smirk.

A look of panic washed over my father's face. Stammering he said, "please Miss, don't make me. Please it is too embarrassing."

She gave him a look that could kill. There was a long silence. Finally she said, "you can either give him his gift, or I can throw it away forever."

The look of panic in my father's eyes grew even more intense as he said, "yes Miss, right away Miss." He then shuffled over on his knees until he was right in front of me. He removed a chain from around his neck and held it out in front of me as he said, "Mister Oliver please accept this gift as an apology for all the years I was bad to you."

At the end of the chain he held out to me was a small silver key. I reached out to grab it with a great deal of confusion. "What does this go to?" I asked.

"Why don't you show him sissy." My step mother said to my father with that grin I had seen so many times today.

My father looked like he was about to cry at this point as he stood up, lifted his skirt, pulled down his white frilly panties, and revealed a small pink cage like device locked onto his genitals.

"That is what they call a chastity device, it is there so she has no access to her little thing. The key you hold in your hand is the only one in existence. From now on he is not allowed to be unlocked without asking for your permission first."

SissyOona
SissyOona
35 Followers
12