My Father, The Maid

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
SissyOona
SissyOona
36 Followers

I was stunned by this and as such was not able to muster any words. I just sat there staring at this little key.

My awed stare was broken by my step mother saying, "you may return to the position." Upon hearing that my father pulled his panties back up, put his skirt back down, and returned to his knees. Tonight you will be punished on three accounts, first for not answering the door for your son as I ordered, second for not referring to your son in a the proper way to denote his position as your superior, and third for not giving your son his gift when you were told to do so."

"Yes Miss, thank you Miss." He replied.

"For the first account your punishment will be to clean all the windows inside and out in one of your frilly pink sissy dresses, you are receiving this punishment because you did not want someone, namely your son, to see you as the sissy you are, this will make sure lots of people get to see you. For the second account your punishment will be to apologize to your son for not addressing him properly, you will do this by writing 'I'm sorry for being a bad sissy Mister Oliver' 150 times during your free time tomorrow. And for the third account, not giving your son his gift, I will be giving you a gift, 50 spankings with the paddle. Plus you were given one hour to clean up after our dinner and eat yours, it took you one hour and twelve minutes to report to this room for punishment, as you know this cannot go unpunished, so for every minute you were late I will add one spank to your previous punishment, bringing the grand total to 62."

"Yes Miss, thank you Miss." My father replied with his eyes cast to the floor.

"Good girl, now go get the paddle." She said sternly.

My father then left the room and quickly returned with a solid wooden paddle. He presented it to his wife and walked to the center of the room where he lifted up the back of his skirt, pulled down his panties, and bent over, grabbing his ankles in anticipation of the punishment to come.

My step mother slowly rose from her seat, she walked into her position behind him, and suddenly hit his bare bottom with her paddle producing a loud slap. She hit him, spank after spank after spank. After about 40 slaps she turned to me, "want a go?" she said holding out the paddle to me.

I must have had a horrified look on my face when she said that, but after a moment I remembered every time he spanked me for no reason as a child. I stood up much to my step mother's delight, took the paddle, and slapped my father's ass as hard as I could. The sound produced was so loud I could swear it could be heard from the street, followed by a little yelp from my father.

I finished the remaining 21 spanks with more pleasure than I thought I would experience from such an odd occurrence. My father's ass was as red as a tomato, I couldn't imagine how bad it must hurt, nonetheless he stood up, pulled up his lacy panties, put his skirt back in place, turned to both of us, and with a curtsy to each said, "Thank you Miss. Thank you Mister Oliver."

"Good girl" Claire said giving her maid a little pat on the butt. "Now Oliver, unless you require anything more of the sissy I think it is time for me to adjourn for the evening, it is one of her duties to prepare me for bed, and she will be off duty for the for the night after I retire."

"No, I think I'm all good. I'm actually pretty tired too, I think I'll also be off to bed." I said with a slight yawn.

"You have an excellent night, if you need anything the sissy sleeps in the second room on the right, you can't miss it there's a big pink heart on the door, just knock and it will be her pleasure to serve you." Said Claire after wrapping me in a hug and kissing me on the cheek.

"Good night Mister Oliver." My father said as he curtsied to me one last time for the night.

"Goodnight dad."

After all these pleasantries were exchanged Claire led her sissy maid down the hall and into the master bedroom. I wandered to the guest room. When I got into the room I pretty much fell into bed, it had been a long and mentally trying day. As I settled into bed I remember the last thing I saw as I drifted off to sleep, a framed picture of my dad and I when I was younger, both with big forced fake smiles on our faces.

END OF PART 1

Hello all, this is my first story ever, I hope you enjoyed it. If you did please leave a review so I know you want more. If you didn't like it also leave a review so I know what to fix.

If you don't feel like leaving a review here feel free to send it as an email.

Thanks XOXO

Sissy Oona.

SissyOona
SissyOona
36 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymousover 2 years ago

Your work isn't done yet. There where a few wording issues. But over all i enjoyed it very much you managed to put a wet spot in my panties Thank you. Tom/Tammy

RegretsRegretsover 3 years ago
Rather overdone on the oppression

I did not like several references..grabbed our food, grabbed the key. Very crude that was. And the fact that the maid is in permanent chastity. How often will the son visit? If the son takes up residence is he supposed to supervise the maids release from chastity. It was most unpleasant, outright slavery. Getting the prenup changed so that he would be destitute if she dismissed him. This was quite repellent behaviour.

This story should be abandoned here and future attempts should have a lot more humanity in the story.

There was one point that I did like. This was that the maid found it almost impossible to hesitate to carry out an instruction. When a couple set forth on a chastity lifestyle or a cuckold relationship the very last thing that is wanted is for the slave to baulk when mistress leads into new territory. For instance, when ordered to give a BJ to her lover. This sort of behaviour would greatly damage credibility. Slaves should not be exhibited until mistress is confident that there will not be a “Stop” when she gives an order.

In short time, this particular couple will face public ridicule and legal scrutiny. Hopefully the property and his monies will be restored into him. This relationship has crossed the bounds and it is not Lit(erotica).

AnonymousAnonymousover 4 years ago
...

He should have been aken a claw hammer to her face the moment she told him about the prenup, then gone and set the lawyer on fire in his car.

AnonymousAnonymousover 5 years ago
Great Start

Realy good so far and interested to see how it develops with further humiliation.......perhaps the son picking a sexy outfit for the maid to wear?

VickieTernVickieTernover 5 years ago
Humiliating

as punishment, not reward, isn't my thing (it's too corrupting of the victim and of the person doing it, each in different ways). But if Dad begins to show signs that he's seeking his subservient feminization and is secretly if wistfully grateful for it, maybe even blissfully enjoying it, this can be a fine story even by my lights! Though others feel other ways, I grant you. A chacun son gout!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Harmless Favor A young wife assists her young husband to become a sissy.in Transgender & Crossdressers
Cream Puff Ch. 01 Sissy finds becomes a strong man's bitch.in Transgender & Crossdressers
From Son to Sissy A young boy's journey to understanding his true sexuality.in Transgender & Crossdressers
Neighbourhood Terror to Sissy Pt. 01 A story about a neighbour who wants some payback.in NonConsent/Reluctance
Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
More Stories