tagTransgender & CrossdressersMy Father, The Maid Ch. 03

My Father, The Maid Ch. 03

bySissyOona©

A Case Of The Mondays

By Sissy Oona.

Sleep came easy that night, I was frankly a bit worn out from the amazing sex we'd had. I was awoken by the door to the room opening and the click of heels on the wood floor. I cleared my weary eyes to see my father entering the room carrying the breakfast tray I had become accustomed to seeing in the morning. Noticing I was awake my father curtsied to me, he then set the tray of food on the chest of drawers sitting near the bed and approached his wife who was still asleep next to me. He stood there for a moment looking at her, I believe he was examining her breathing and her eyes to try to figure out her sleep state. After a moment he kneeled beside the bed and said "good morning Mistress, it will be my pleasure to serve you today." Upon hearing this Claire woke up and adjusted her position to be more upright, less lying down and more sitting up. As she did this my father, who was wearing a blue satin maid dress which was supported underneath by a sea of petticoats as usual, white floral patterned tights, and blue heels that matched his dress, stood back up and retrieved the tray from where he had left it and placed it on his wife's lap so she could eat. Once she was properly situated my father turned to me and said, "if you will excuse me I have also prepared breakfast for you Mister Oliver, would you like me to bring it in?"

"Sure, sounds great." I said with a smile. My father curtsied in response and left the room.

After taking a few bites of her customary egg white omelette Claire said "last night was excellent, you are much better in bed than your father" as my father entered the room with my breakfast.

After serving me my breakfast my father stood at the foot of the bed and meekly said, "may I make a request Mistress?"

"You may." Claire said in a stern, almost annoyed voice.

"Thank you Miss." He said with a curtsy. "May I be allowed to get out of uniform a bit early today so I may go to the office earlier than usual to get Mister Oliver's employment paperwork in order?"

Claire slowly chewed her food as she stared at him. Her gaze was so intense I swore it would burn a hole straight through him. She set down her fork and calmly but pointedly said, "no, you may not. The men from the furniture store will be here at noon, you need to make sure Mister Oliver's room is spotless as not to embarrass me. Once they have finished and any mess resulting is tidied then you may go to work."

"Yes Miss" he said disappointedly with a curtsy.

"Good, now you may go, we will ring when we are ready for you to collect our dishes." Claire said with a small wave to dismiss her subservient husband.

Breakfast was consumed in relative silence. As I sat there in eating my breakfast in bed, naked, and next to this gorgeous woman I felt amazing, like this was the life I wanted to live until I died. Eventually Claire and I finished our meals, noticing I was done too Claire picked up the little bell that was always near her and rang it. A few moments later, heralded by the click of his heels down the hallway, my father entered the room. He gathered up our trays and dishes and promptly left the room.

At this point I decided it was about time to get up and get dressed. As I rose from bed, naked as the day I was born, I looked around for the clothes I had been wearing last night but they were nowhere to be found. "Where are my clothes?" I asked as I stretched.

"Oh the maid must have taken them to keep the room tidy. Don't worry about it, you have a nice physique and are well endowed, you have nothing to be ashamed of." Claire said with a coy smile.

This compliment brought a smile to my face and bolstered my confidence a bit, it's not every day someone as gorgeous as Claire paid me a compliment. As I strode for the door with an admitted bit of swagger in my step I was interrupted by my father entering the room once again. I could tell he was about to say something, but was stopped by the sudden surprise of his naked son standing before him. I couldn't help but notice as he looked me up and down, stopping for a moment at my morning wood erected penis.

"Doesn't Mister Oliver look good naked sissy? Who knows where he got such a manly physique from. Certainly not from you." Claire said with a laugh.

With eyes cast to the floor with shame my emasculated father said, "thank you for allowing me to behold your manliness Mister Oliver. It is an honor for me to be in the presence of a real man."

This caused Claire to laugh once again. I didn't know what to say, on one hand it was awkward to be seen naked by my father, especially in this state, and on the other hand I have to admit I liked the power I felt over him in that moment. All I could muster was a smirk as I walked past him and out the door.

As I passed I heard him ask "Mistress may I dress you now?" To which Claire responded in the affirmative.

After all this I finished my morning routine and got dressed. Once I was ready for the day I realized I really didn't have anything to do, so I went into the living room to watch some tv. Shortly thereafter I was joined by Claire, she was wearing a blue flowy skirt that stopped just above her ankles and a simple white top. As she joined me on the couch she said, "the maid should be busy until lunch time. Do you remember what time your furniture is to be delivered?"

"Between noon and one I think." I said.

Things were quiet for a while, we sat watching whatever nonsense was on that early in the day, in the distance were the occasional sounds of vacuuming and other such cleaning tasks. At about noon my father entered the room with a curtsy, "Are you ready for me to begin lunch Mistress?"

Claire turned slightly to me as if asking if I were hungry, I gave a nod. "Yes we are." She said to her domestic servant. "How does a chicken caesar salad sound?" She asked me, to which I agreed. With that the maid was off to the kitchen to prepare lunch.

About five minutes later the doorbell chimed, I could see out the window that the truck from the furniture store was sitting in the driveway. After I brief moment, hearing the sounds of active cooking from the kitchen I rose from the couch to answer the door. Claire told me not to worry about it and that the maid would take care of it, but I said I would let him keep cooking, and since it was my stuff I may as well let them in. I opened the door to find two rather burly men, both wearing lifting belts and one holding a clipboard.

"Is this the home of Oliver Milton. I got a delivery for that name at this address." Said the man with the clipboard, named Sal as indicated by the name tag sewn into his work shirt.

"Yeah, that's me, you're in the right place." I replied. I signed a bit of paperwork and the men went to work loading the boxes off the truck, first the desk, then the office chair, and finally the armchair. All of this was taken into my room where the men said they would gladly assemble it all free of charge, all I had to do was show them where I wanted everything. After I showed them where I wanted everything I excused myself to the kitchen where I found my lunch waiting for me.

As I sat and ate my father was busy cleaning up the dishes he had used to make the meal, as he finished Claire paused from her mostly finished meal and said to the maid. "Those workers must be parched, go offer them a drink like a good little girl."

My father turned red at this, but meekly curtsied and obeyed. I heard his heels click ever further down the hallway, before long I knew he was outside my room. Claire and I both listened intently. "Would you gentlemen like anything to drink?" I could faintly hear my father ask in his undoubtedly male voice.

"No thank you sir-" I heard Barry, the second workman say, but from the way his sentence cut off I can imagine what happened. I am certain when my father first addressed the men he was still standing in the doorway, not noticed by the workmen until he spoke. Barry began his sentence before turning to see who had just spoken. I guess this to be the case because just after his sentence was cut off there was a bout of laughter from the two burly men at the pathetic site of my feminized father before him. Once the laughter had subsided I heard Barry correct himself, "no thank you 'miss'" I heard him say, emphasizing the last word with a chuckle. Another bout of laughter soon followed, I suspect brought on by a curtsy from my father as he left them to their work.

Soon after Claire and I finished our lunches and adjourned to the living room. About a half hour later Sal walked in and said "We've got everything put together and it should all be in the right spot. Come on in and check out work real quick, and if everything looks good we will gather up all the trash and be on our way." I got up and headed down the hall to see my newly put together room.

"Everything looks great." I said after giving everything at once over.

"Excellent." Sal said. "We'll just clean up our mess and get out of your hair."

"No need, I'll have the maid take care of it." Claire said as she grabbed her little bell, summoning my father. "These nice men are finished setting up your son's room sissy, get my purse so I may tip them."

"On, no ma'am, we don't accept tips." Sal said before my father had a chance to leave the room.

"That's a shame." Claire replied. After a brief moment a devilish smile crossed her face. "Well if you can't accept a monetary tip I can at least offer you use of my maid. She is quite skilled at oral, and is always willing to give up her asshole to nice cocks." Upon his Mistress saying this my father sunk to his knees before the two men, knowing if he didn't he would be punished.

The two burly men were obviously taken aback, this was certainly becoming the weirdest delivery they had ever done. After a moment Sal spoke up, "um that is very kind ma'am, but uh, we have other deliveries today, so we really should get back to the store."

"Very well, I understand. Show these nice men out sissy." Claire said with a kind smile.

My father led the two men to the front door where he gave them a nice curtsy and thanked them for their services. He then returned to my room and cleaned up all the mess from my new furniture. Once this was complete he found Claire and I once more in the living room where he curtsied and asked. Miss I have finished cleaning up the mess. May I go change so I may go to the office to take care of Mister Oliver's paperwork?"

"You may, but remember, those earrings cannot come out. Also, I have told Nancy you would be coming in today, she wants a latte, you know what she likes." Claire said sweetly. The maid curtsied and left the room. About 15 minutes later he returned looking like the man I had known most of my life, jeans, suit jacket, he looked like what the rest of the world knew him as, a man.

After he left things were quiet for a while, Claire and I sat on the couch for a while watching tv, but I eventually grew bored of this and headed into my room to do some light gaming. A few hours passed and I decided to get up to get a drink, I also realized that my father had been gone longer than expected. I went out to the living room to ask Claire what was up, she was paying most of her attention to her phone. After I walked in she looked up and said, "I was just about to come talk to you, we unfortunately will not be served dinner tonight. It seems the maid will be detained a bit."

"Oh, okay. I'll figure something out. Probably get delivery." I said and turned to leave the room.

"If you don't mind waiting a little bit the maid can pick something up on her way home. " Claire said with that devilish grin I knew well, before I could leave the room. "How does Thai sound?"

"Works for me." I said.

We sat for the next thirty or so minutes talking and watching tv, when suddenly Claire started laughing after looking at her phone. "What's so funny?" I asked.

"Do you remember last night on the way home from the mall I mentioned someone named Mark? Well he is one of my boyfriends, he was supposed to come over last night to have sex with me, but wasn't able to. Well a little while ago he texted me saying how horny he was and how much he wished he could have come over yesterday. Well, I couldn't let him stay that way, so on her way home from the office I sent the maid over to help him out, she just sent me this picture." She then handed me her phone which was illuminated with a picture of my father dressed only in a white lacy bra and panty set with a man's penis in his mouth. I almost dropped the phone I was so surprised by what I saw. In retrospect I shouldn't have been as shocked as I was to see this after everything I had seen here the past few days, but something about seeing my father with a real penis in his mouth was truly shocking to me. I handed the phone back to Claire as she continued with whatever normal conversation we had been having. Not long after she asked for my order and said the food would be here soon.

About forty five minutes later we heard a car pull into the driveway, and the maid entering with our dinners. As he walked in the door something looked odd about him, like there was something on his face. Not able to figure out what it was I had to ask, "hey, what's all over your face?"

"It's Mister Mark's cum Mister Oliver, he said I was not allowed to clean it until I returned home." My father said with great shame in his voice. This of course elicited a laugh from Claire.

Claire and I continued our conversation in the dining room over dinner while my father went to get into uniform. After Claire and I finished eating we returned to the living room where we found my father, back in uniform on his knees in the middle of the room.

"Good sissy, early for punishment time. Overall you have been pretty good today, there is only one incident you need to be punished for. Do you know what that is?" She said in a tone both playful and commanding.

"I asked to be allowed to change for work when there were things I was needed for Mistress." He replied.

"That is correct. And since you want to go to work so badly tomorrow you will do just that. I have talked to Nancy, tomorrow you will meet her at the office extra early, before anyone else arrives for the day. You will be in full maid attire and you will attend to some tasks for Nancy, hopefully you will be done before anyone gets in. Oh, and bring doughnuts" Claire said with a chuckle.

"Yes Mistress," he said eyes cast to the floor.

"Very well then. We need nothing more if you until bedtime sissy, you may go enjoy some free time." Claire said, dismissing her domestic servant.

There was an awkward silence for a moment as my father did not move, but instead eventually said. "May I ask a question of Mister Oliver Mistress?"

"You may." She replied.

"It has been an honor to serve you the past few days Mister Oliver. I hope I have met all your expectations of me. I know I have no right to ask this, and I assume you will say no, but may I please unlock my chastity cage and touch myself?" he said with eyes cast to the floor.

This made Claire laugh quite a bit, she turned to me through a chortle and said, "well do you want to let her play with that pathetic little thing?"

I thought about it for a moment. "How long since she was last unlocked?" I asked Claire, much to her surprise I think.

"God, it's been at least three months." She replied.

I considered this for a moment the slowly and without a word stood from the couch. I walked out of the living room still saying nothing, went to my room, and retrieved the key from my computer bag where I had stashed it the other day. I silently walked back into my room, my father had just stood up when I entered. He quickly fell back to his knees and started begging forgiveness for asking such a question. As he continued to grovel on his knees before me I dropped the key so it was on the floor right in front of him. When he finally saw it he immediately changed his tune from one begging forgiveness to one full of thanks. He grabbed the key and quickly stood up and started leaving the room.

"Where do you think you're going?" I said as sternly as possible.

"T-To my room to play with myself Mister Oliver." He said nervously.

"No, do it right here, I want to see how pathetic you are when you play with that part of your anatomy you gladly did not pass on to me." I said, after which Claire gave me a surprised but happy look. I'll admit saying all this was weird to me, but after seeing my father sucking a cock earlier that day I knew his life was irrevocably changed and now that I was a part of it mine would have to too.

Claire pretty much squealed with delight at this, seeing the utter humiliation and shame in my father's face. After a few moments of our maid standing there dumbfounded she said, "hurry up, unlock yourself sissy."

"Yeah, be quick about it. In fact, if you aren't unlocked before I count to five I am taking those keys back." I said and immediately started counting. The look of fear on the maid's face was something to behold, and to watch him fumble with the keys was quite humorous, but by the time I got to four the pink plastic cage fell to the ground, and his shriveled genitals were in full view.

He started stroking what little he had to grab onto down there, even though it was slowly becoming erect it wasn't growing very much. This whole ordeal was taking a while. Quickly becoming annoyed Claire said, "I know, she has forgotten. She needs to see how to play with one of those." She then started stroking my cock through my pants, I was a bit hard from the power I had been feeling over my father, this confused me, but I didn't think much of it. Before long my pants were down and my cock was fully engorged and in full view as Claire was stroking it. I could see my father's eyes fixed on it, it looked as though he was going to cry, but nonetheless he was stroking himself.

I then saw a small drop of precum start to develop on the tip of his tiny member, thinking in the moment of another devilish plan I reached for the glass of wine I had been sipping, drank what little was left, and handed it to him saying, "blow your load in that sissy so it will be easier to drink."

"Yes Mister Oliver" I heard him say with a quiver in his voice. Not long after this I could tell he was ready to orgasm. I watched intensely as a few small short spurts were fired into the wine glass. Claire and I both laughed at this, Claire all the while still stroking me.

"Drink your cum sissy, but don't swallow. You don't get to swallow until your wife makes me cum." I said looking him straight in the eyes. Claire laughed at this and started stroking slower as he sipped up his cum. Claire motioned to him with her other hand to return to a kneeling position.

This went on for what felt to me like at least a half hour and for what I'm sure felt like an eternity to my father. Eventually I could feel myself getting close to cumming. Claire could too and motioned to the maid to come closer saying, "I want you to not only see, but feel how a real man of your family cums." She placed him so that when I came it would be all over his face.

She began stroking more and more vigorously all the while flinging an insult or two at my father. In all this commotion and as I felt myself getting closer and closer to orgasm none of us noticed the sound of a car door slamming in the driveway. It was just as I blew my load all over my father's face, Claire's hand still wrapped around my cock that the front door opened and a gorgeous girl in her early twenties walked in. "Well, well, well, what do we have here." She said looking at the spectacle before here. It was only then that I knew who it was, Aimee had come back home.

Report Story

bySissyOona© 3 comments/ 7211 views/ 5 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel