Maid Service

Story Info
A maid with something extra and a mean streak.
2.3k words
4.26
17.7k
23
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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
TheeAdult
TheeAdult
45 Followers

I had recently moved to the Philippines on a retirement visa, being 50 with an early buyout meant I had to be more frugal but I felt retirement overseas could work. Little did I know how far the dollar would go.

After arriving I rented a condo and with utilities my monthly nut was under $700. At first the girls who came over would do light cleaning before we moved on to the bedroom. Some were better than others both at cleaning and at sex, but after talking with neighbors I felt a full time maid would be best. Since I had only a one bedroom condo she couldn't be a live-in maid so I contacted an agency who found me a maid.

I sat down with her and went over what was expected and her salary. Kyla agreed to everything, I think she liked me. She would work 6 days a week between 1pm-7pm not only cleaning but also cooking my lunch & dinner. She started in the afternoon because most days I didn't get out of bed until noon. Sometimes she would see my guests from the night before leaving and shared a word or two with them.

Occasionally I would find a girl I liked and we would stay together for a few weeks or months, no promises were ever made but sometimes the girls expected more.

The latest was an ugly breakup. Julie was yelling when Kyla walked in. Julie was mad because she gave me her ass cherry hoping that I would fall in love with her. As she left I said goodbye and thanks for her ass cherry.

Kyla got to work and I hopped in the shower. I came out of the bathroom and went into my closet, but my clothes weren't there. I hadn't noticed if Kyla picked up my laundry this afternoon because I was trying to get rid of Julie. Since I was already frustrated that day I stormed out of my bedroom yelling for Kyla and my clothes.

"Did you forget something?" I loudly asked Kyla. "Where are my clothes?" That's when the other shoe dropped. Kyla responded "Julie is my cousin and you hurt her. Maybe I should hurt you!"

"Okay, that's it, YOU'RE FIRED, GET OUT! You never did clean well and you always forget my laundry." The look on Kyla's face wasn't one of disappointment but rather excitement. She replied "Don't worry you won't need clothes today and we will see about my cleaning skills." As she rushed towards me, she pulled the towel away and grabbed me trapping my arms to my sides as she dragged me into the bedroom.

Her strength overwhelmed me as she threw me down on the bed. She straddled my naked body and told me that I need to be taught a lesson. She slapped my face and told me to stay on the bed.

She got up and went to the bottom drawer, I knew what was in there but I was surprised she knew. She must be going to through my drawers when I wasn't home. She took out some restraints and came back to the bed, she proceeded to tie me up and play with my body.

She started with my nipples and her other hand quickly went for my cock or so I thought. Her hand went right past my cock and balls and started playing with my asshole causing me to squirm. As she rubbed my asshole. I started to protest and struggle but she just laughed.

"Okay it is cleaning time" as she dragged me into the bathroom. She bent me over the tub and told me to stay, as if I was going anywhere with my feet and hands tied up. She returned with a large enema syringe and water.

"Please don't, I promise you can have your job back with a raise!" I begged as she began to fill the syringe.

"I want to show you my cleaning skills boss. I want to clean you inside and out. First we will start with the inside!" I winced as she inserted the enema tip into my asshole. She began to depress the syringe filling my ass with the enema.

When the syringe was empty she sat me on the toilet and left the bathroom. As my bowels emptied I could hear her opening my bottom drawer gathering, what I would soon find out, various sex toys and props.

When she came back into the bathroom she lifted me up and used the bum gun to wash my ass. "One more time to make sure you are clean, I wouldn't want you to get mad if I didn't clean good enough" she said as she bent me over the tub and filled up the syringe again.

While I was on the toilet she turned on the shower and left the bathroom. She must have gotten undressed in the other room. When she came back she was naked except for her panties where I could see a huge bulge in her panties. She saw me looking and laughed, "Yeah I know it's bigger than yours". She has a cock!

I started begging again "Please I will pay you anything, just let me go". She replied "Okay for one million US dollars" knowing I didn't have that much money.

She dragged me into the shower and pushed me face first against the wall of the shower. "Stay there" she said. After a moment I felt her climb into the shower behind me and I felt something hard and firm rub across my ass and thighs, I knew it was her cock but I pretended I didn't know.

She started to soap me up from my feet to my head spending a lot of time on my ass and dick. Even though I didn't want to be I was hard due to her playing with my body as she was cleaning me. "Oh, look your little dick is hard from me playing with your pussy. By the way I like ass cherries as much as you do"

"My dick is hard too" she whispered into my ear as she started to fuck me between my thighs pressing me against the wall. I could feel her hard cock rubbing my thighs and balls as she fucked my thighs using the soap as lube. I squirmed to try to get away but there was nowhere to go.

When she was done playing with me she rinsed me off. After stepping out of the shower she proceeded to dry me and then dragged me back into the bedroom. "Now that you are all clean it's time to get dirty!" she said as she sat on the bed and laid me across her lap.

I felt something small go into my ass and then I felt the lube squirt into my ass. I knew then she had found my lube syringes. She used a second syringe to make sure I was well lubricated.

"Time to teach you a lesson!" she said as she started spanking me. Occasionally she would stop spanking me and rub my asshole making me squirm. I pleaded with her to stop but she just laughed and said "I have been waiting for this forever. You do nothing around the house and expect me to clean it all up."

Wasn't that her job I wondered to myself as I laid over her lap getting spanked like a child.

She stopped for a minute and I felt something larger than her finger pressing on my asshole. I groaned as it found its way into my ass. I realized it must have been one of my sex toys. When the felt the second bead I knew it was my anal beads.

She turned on the vibration and I started moaning. "Yes baby keep moaning for me, I like that." She laughed as she continued to fuck me with the anal beads.

After a bit she pulled them out and replaced them with a butt plug. It hurt going in but she didn't care. She pushed me off her lap and had me kneel on a pillow on the floor. She told me it was time to scrub my insides with her cleaning stick. I didn't know what she met until I saw her holding her huge cock.

"First let's start with your mouth, I will clean your throat." She told me as she dragged my head to her cock. "Open wide bitch, it's time to scrub hard."

I was taken by surprise so I just opened my mouth and took her cock in. She kept giving me directions; lick here, suck harder, deeper, etc. As she gagged me with her cock. She had me lick her balls and her ass also.

She started telling me to work faster for the special cleaning solution. She told me that I better swallow it all. I knew what she was talking about; part of me dreaded swallowing her cum but the other part of me was relieved that she only wanted a blowjob.

When she reached climax she held my head and told me "You better swallow it all bitch, here it comes." As I felt her cock erupting in my mouth I swallowed as fast as I could. I felt some drip out of my mouth and she got mad. "You better clean up after yourself!" So I licked up the remaining drops I missed.

After she was finished she got up and pulled me up to my feet. "You are always complaining about my cleaning. Let's see how good you can clean" she told me as she untied my hands and handed me a rag. "Start dusting bitch!"

With my feet still tied I couldn't escape, besides where could I escape to being naked, I couldn't just run outside. As I started cleaning she sat down and watched me. She would critique my cleaning, telling me to bend over more when I cleaned the bottom of the furniture. Finally she stood up and said something is missing. She grabbed her uniform and panties and told me to put them on.

"Now you look like a maid even if you can't clean like one. Now get back to cleaning!" She said as she smacked my ass under the skirt.

I was humiliated and started to sob a bit. "Well if you are going to cry like a girl I might as well make you look like one! Sit down in the chair!" she commanded and I took a seat. She pulled out her makeup and started making me up. She told me to stop crying or she would give me something to cry about as she grabbed her cock which started getting hard again. I was nervous about my ass so I sat there and obeyed her.

When she was done she stood me up and had me twirl around as the skirt lifted up.

"Now you have to clean the windows. The furniture is too heavy to move so the best way is to kneel on the couch and lean over the back to clean the windows." As I did so she came to the side of the couch and grabbed my wrist. "No you have to bend over very far" she said as she pulled my wrist down. I felt something silky go over my wrists and I realized she had tied me to the back leg of the couch.

She laughed as she stood up and went around to my backside. "That's a nice position, sexy bitch. Is this how you fuck girls in the ass?" I didn't answer her as I felt her lift up my skirt and pull down my panties.

I felt her grab the butt plug and pull it out. I felt relief but also emptiness. She picked up the lube syringe and shot another load into my ass. Then I heard her stroking her cock, she came around to my side so I could see her lubing up her cock as she smiled down on me.

"Ready to lose your cherry bitch?" I am not sure even if I said no that she would have stopped.

"Time to scrub the inside of your ass. I will make sure I get really deep." She said as I felt her cock head at my ass pressing into me. I yelped as her head popped into my asshole, she laughed and slapped my ass. She slowly kept pressing until I felt her hips on my ass, I was so full. I begged her to stop but she told me that it will just hurt for a little while.

She started fucking me slowly in and out, as I moaned like a girl. "You sure sound like a bitch." She said. "But don't worry I doubt the girls you fuck in the ass have as much pain with your little cock. Actually it is more like a clit so that makes your ass your pussy! So now it's time to fuck your pussy." She said as she started fucking me faster.

I tried getting away but I couldn't go anywhere. I think she liked me squirming as she fucked me faster and faster. Finally I felt her get bigger and she yelled out "Here it comes!" as she shot more of her special cleaning solution into the condom. When she was done she pulled out and took off the condom and poured her cum onto my face.

She untied me and brought me to the shower. She had me to clean her thoroughly. Then she left and told me to wash up. I felt my asshole in the shower and it was raw and sore. I cleaned as best as I could.

When I walked out of the bathroom she was dressed and getting ready to leave. "I will be here tomorrow at 1pm, you better be naked and on your knees ready to serve me bitch!" she said as she walked out the door.

I knew my life had changed forever.

TheeAdult
TheeAdult
45 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
4Leather4Leather9 months ago

Wish I could find a true T-girl to take full control. That would be so HOT. Chapter two please, want to see if he is kneeling waiting for her arrival.

AnonymousAnonymous10 months ago

Will there be a follow up? I'd love to see like.. a week down the road and see Julie get some payback too. Nothing hotter than a broken man under the thumb of someone with a bigger cock.

AnonymousAnonymous12 months ago

Loved it,,, the tables are turned and now he is the maid and the bitch , hope she forces him to suck many other friends cocks and beat him daily and forced to go and clean her ladyboy friends apartments , true bliss

juliemay808juliemay808over 1 year ago

Loved it the idea of being a bitch for T girl mistress so hot

Share this Story

Similar Stories

The Bet Hung girl wagers that Billy will love her cock in his ass.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
Locked Out of Apartment The sexy neighbor girls have a surprise.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
Jake's New Mommy Ch. 01 18-year-old runaway Jake is 'rescued' by a mysterious woman.in Transgender & Crossdressers
More Stories