Annie
Introduction:
From a whore to a maid… was there really a transition?
Yesterday I had driven down to the nearest mall and sat on a bench right outside of Macy’s and placed my purse on my lap and rammed my fingers down the front of my pants and went to town. It was a busy time of day and I figure the security guard who kept circling me like a hungry hawk knew what I was up to but I finished in record time and was off the bench and out the door before I was thrown out of the mall for lewd behavior and into the county jail. Fuck that.
I had to find a job. I couldn’t keep “renting” myself out on “dates.” If I had to lie one more time just to get a few extra bucks to a man whose dick I didn’t want anywhere near me, I was going to take on the ghastly role of Charlize Theron in Monster. Ok, that was an exaggeration. Still. Never hurts to plan ahead.
I need a drink.
I stopped off at a local hole-in-the-wall pub, called Last Call and figured I’d be there til just that..Last Call.
The night before I had met a guy named Frank who kept buying me drinks and I felt obliged to go home with him. He promised to buy me dinner and a cab fare home and a few “extra dollars” because he “liked me so much.”
That’s not prostitution. Is it? Hell, I didn’t care anymore. Money is all green and it spends the same, no matter if I fuck my boss or fuck a bar stool friend, right? Oh good god, I’m a whore.
“Annie, you’ll never be anything. You will just be like your whore mama and have 17 illegitimate children who will most likely end up on welfare or in prison, just like the rest of you kids who dropped out of school. Nobodies.”
Fuck you, Aunt Carol, I said in my head and most likely out loud. That bitch never knew when to shut her pie hole except to chew her food. At least she gave us that.
So here I sat on the same stool as last evening nursing my scotch, extra neat.
Extra neat. What the fuck does that even mean?
A man sat two stools down and looked like an executive of sorts but to be honest he looked a little out of place here in this hole. Wondered if he was wandering around for some stray. Renting myself crossed my mind again but figured I’d call it a night after my “extra neat” scotch.
Feeling a bit buzzed from the alcohol, I sauntered over to Bill….that’s what I had named him in my head…. and asked him why was a good looking rich man like him doing slumming with the best of us downtowners.
Bill, as it turns out, was the brother of the bartender, and his name was actually Stephen. With a “ph.” How fancy.
So, Stephen and I struck up a conversation about the weather while I thought about how big his hands were and wondered if his dick held that same statistic.
Before I knew it, I had my hand on Stephen with a ph’s leg and was moving in. He kind of backed up sideways and peered at me and asked me what was I doing out alone.
He was no rocket scientist, that I could tell. Bill could tell I was a worthless whore like my Aunt Carol liked to tell me and pray to Jesus to help me turn my life around. Stephen, Bill, all the same to me. Whatever. Fuck Aunt Carol.
Somehow he mentioned he had just moved to the city and needed a housekeeper. Well, why not? I’d been renting my fucking body out to men for so long I had not considered there might be a real job out there that paid decent money. Yet, here I saw talking to Stephen about his lack of servants. Stephen needed a maid because he had no wife or kids and didn’t want to be burdened with such tedious meaningless things.
He asked me what my career was. Pffft. Career. I about spit out my extra neat scotch. “Career,” I said. “well Stephen, I don’t have a career.
He took my number and I walked home thinking Stephen wouldn’t call. I bet if his name was Bill he would call. Stephen. Pfft.
“What the fuck is all of this nonsense??” The damn phone was ringing louder than I’d ever heard it ring. I answered. Stephen asked me to stop by for an interview. I got the address, got dressed, and hurried over. I’m sure my clunker of a car made a great impression as it backfired while I was parking in the circular drive. Fuck me now.
Where’s a extra neat scotch when you need it?
Stephen answered the door after the first knock. I then noticed there was a doorbell. God, he must think I am as uncouth as Aunt Carol.
“Annie?”
“Yes?”
“Do you have any experience in this line of work?”
“Well, I helped raise my brothers and sisters and helped a few family members out. I know the basics of cleaning a house.”
“This one is different…..,” Stephen trailed off.
Holy fucking balls. Guess I was “renting” again. Wouldn’t fucking Aunt Carol be proud?
“Let’s cut right to the chase, Annie. I am a different kind of man, one many wouldn’t work for so you need to know what the expectations are because they are different and I am not pressuring you to take this job, but if you do, I expect full cooperation.”
Doesn’t all bosses? God I was getting horny.
“This job isn’t like any other maid position. You will be paid weekly, above average for the reasons I will discuss later and you will have the option to be a live-in maid or you may come early and leave late. Duties will include laundry, vacuuming, tidying the house, dusting, basic inside work, no cooking.”
Were we not going to eat?
“Barbara is our full time cook and she is over everything in the kitchen and she doesn’t stay over night. If I entertain of the evening, you will be required to help her serve dinner but other than that, you are just the maid. Any questions?”
“Yeah. When do I start?” I needed a house, although he didn’t need to know that shit.
“First we talk about the other part that goes along with this job.”
“Ok,” I said.
“If things aren’t clean to my desire and expectation, I will spank you. You do not have to wear a traditional maid’s uniform but you must dress nice. If you have no nice clothes, I will take you shopping to get the clothes you will need. There are other, more harsh punishments, but suffice to say there will be spankings.”
Spankings? What the fuck?
“I’ll take the job.”
Stephen decided that evening he would take me shopping to get the necessary items for me to dress up to be a maid. We shopped for hours getting the right dresses. Not too long, not too short, show just enough cleavage but not spill out. The man knew what he wanted. He sprang for a new haircut and style and we were loaded down with shoes and dresses and skirts and jewelry by the time we were finished. I never felt more like “Pretty Woman” in my entire life.
Aunt Carol was right. I’m a whore.
Damn good one though.
He showed me to my “quarters” and gave me a detailed list of what must be done each day before he came home.
That night I took a long bath with scented soaps and felt pampered. I was relaxing in a huge white porcelain tub when he just waltzed in like the door wasn’t locked.
I just laid there looking at him in shock. He smiled and got down on one knee and told me he had laid out what I was to wear the next day. Apparently this was going to happen every single day.
The bed was huge and wonderful. I sank down inside it and snuggled down deep and slept like a baby. I didn’t hear an alarm. Probably because I didn’t set it. Getting up was hard because that bed was divine. I had chores.
I put on my new attire and I felt like I owned the house. But I was just the maid. I got the list out and started working on dusting the entire house. This fucking house was huge and it took three hours to complete. My feet were sore from walking in the high heels he insisted I wear while cleaning.
Upon his arrival, I met him at the door, as noted in my instructions, and we exchanged pleasantries. Stephen immediately put on a white glove.
REALLY??
He went through the house rubbing everything while I stood with my hands clasped waiting on a verdict of a job well done.
He turned to me and said “may I see you in the bedroom, please?”
Sure.
We entered the master bedroom and he showed me his gloves weren’t spotless. He explained this is where I would get disciplined.
I felt like a child. I couldn’t believe he was serious. How humiliating. I was 31 years old for CHRISSAKE.
Stephen bent me over the bed and pulled my dress up and pulled my panties down below my ass and placed one hand on my back to keep me still, or at least give the illusion he was “making” me be still. His hand could barely be felt.
He first spanked one cheek and then the next, back and forth, until I was getting very uncomfortable. He narrated how many licks he had given me and how many more I deserved and asked me if I knew why I was getting spanked.
I said, “I didn’t dust good enough? It was phrased more like a question than a statement.
I was correct.
But then…. I felt his fingers tug my cheeks apart and slip his finger inside the crevice of my ass. This was thrilling to say the least but we had no prior discussions about this. I was aroused so I didn’t say anything. This prompted him to go deeper. He pulled my panties all the way down and they fell around my ankles. He tapped my shoes making me spread my legs wider. He put his hand beneath my ass and rubbed the top of my pussy. My clit started to swell. I was getting wet and I was a little embarrassed about this because I didn’t know how far this was going to go and I needed this job and didn’t want him to think I was a common whore, even though I guess I was…. Should I stop him? I’m going with… No.
He petted my pussy lips and spread them with one finger and dipped one inside me. He could feel my warmth and wetness and he was teasing me. My ass was still stinging from the spanking but nothing major. Humiliating to someone who never had that done to them but this was overtaking the focus.
His pants unzipped, I heard it happen. Was he going to fuck me?
Yes. He was.
He had his dick aimed right at my asshole and he started slowly putting the head of his dick inside my ass. My ass was resistant and tight but he kept pushing.. I felt his breath in my ear… “You want this cock inside your ass, Annie?”
Breathless, I answered, “yes.”
“Say please.”
“Please.”
“Please what?”
“Please give me that big fat dick in my ass!”
“Yeah! Say it again.”
“I want to feel your dick in my ass.”
And I did.
He was pounding my ass. The spanking was nothing compared to the beating my ass was taking from this man’s dick. He had me bent over the bed, my ass in the air, he ripped the dress right off my body and before I knew it he had me turned over and we were sitting up with my legs wrapped around his chiseled body, still connected by his dick in my ass. He bounced me up and down and he said, “you want daddy’s dick in that little wet pussy?”
I did want that.
“Say you want daddy’s big dick.”
“I want your big dick in my pussy, daddy, give it to me.”
Out of my ass and into my pussy, not missing a beat. “Daddy loves his pussy.”
I agreed, I loved Daddy’s dick in my pussy, too. We rolled around and I ended up on bottom with my legs spread and he took my right tit in his mouth and swirled his tongue around the nipple. He licked me from my chin down to my throat, around my tits, down my stomach and kissed the small mound of hairless cunt, all wet from being fucked and now he was kissing me there, licking me there, telling me daddy loved his little pussy.
I loved daddy at this very moment even though I knew it was the sex and later I would not love daddy so much.
Daddy spread my legs open wide and over my head and put his dick back in my pussy and I could tell by his breathing he was about to cum all over me. He pulled out and let it squirt all over my cunt, belly, tits, and neck. I looked up and he was still wearing his tie.
I’m gonna like this job.
