My Assistant, My Slut Pt. 05

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Mary Ann is broken.
5.5k words
4.31
56.5k
20

Part 5 of the 6 part series

Updated 06/08/2023
Created 05/18/2016
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I had a nice dinner with my wife that night, but I have to admit my focus was elsewhere. It was on my slut Mary Ann. My wife told me on the way home that her sister had called and asked her to join her shopping at the outlet mall upstate. They were thinking of making a day of it and then having dinner, spending the night and coming back on Sunday after more shopping. I told my wife she deserved it and that she should go with her sister. It was settled, my wife would be gone until Sunday.

I kissed my wife good bye Saturday morning as her sister picked her up for their shopping trip. I quickly called Mary Ann's cell phone.

"Morning Mary Ann. Ready to be my slut again?" I asked her.

"I'm sore Dave." She told me.

"Where?" I teased her by asking.

"You know damn well where I'm sore." She told me.

"Diane left with her sister for an overnight shopping trip. Joe's gone until tomorrow that leaves you available for my use slut." I told Mary Ann. "Get showered and get ready to go."

"Where are you taking me?" she asked.

"You'll see Mary Ann, just get ready." I said.

When I arrived at her place she was wearing a pair of jeans and a rather conservative, typical Mary Ann shirt. Well dressed, but not much sex appeal to her outfit.

"I was thinking that you would wear some of the outfits that I bought for you yesterday." I said as I handed her a corset and some stockings.

"There are no panties or bottom to this outfit Dave. I can't wear this out." She lamented.

"You can and you will if I desire it." I told the slut. "Now change right here. I want to watch."

Mary Ann pulled her shirt out of her pants and unbuttoned it letting it slip to the ground. She unhooked her bra exposing her pretty little tits. Mary Ann then pulled off her jeans and panties and stood before me completely naked and vulnerable. She is truly my slut and I intended to test her limits.

"Be honest with me Mary Ann, you are enjoying my abuse, aren't you?" I inquired.

"I didn't like it when you clamped my body or made me masturbate in front of the homeless, but something inside me kept me from stopping to play with myself in front of the salesgirl. I was upset and couldn't believe what I was doing in front of her, but something inside me felt great and I couldn't stop." She admitted. "It scared me. All I could think about was making myself cum."

While she was talking she was rolling the black fishnet stockings up her legs to within a fingers reach of her pussy. She then put on the black corset with the violet colored trim including an outline around the tits. She fastened it up with the bottom of the corset ending just below the Mary Ann's belt line. The black color of the corset and stockings made her fair skinned pussy stand out. Mary Ann looked beautiful.

"Does your pussy itch from me shaving it?" I asked.

"Yeah. It's starting to itch sometimes." She said.

"We'll have to keep it closely shaven. I'd love to watch you shave it. We'll have to remember that for later." I said.

"You have to admit, you've had some great orgasms." I told her.

Mary Ann said, "I'll give you that, but why do you have to humiliate me and degrade me? You are having your way with me and I'm not resisting too much because I don't want Joe or my family to find out. I'd be ruined. Can't we just stay here and you can do anything you want, but don't embarrass me again. Please Dave."

"You were getting off having the salesgirl watch you. That's why you didn't stop." I replied. "I'll tell you what Mary Ann, we were going to two different places to put you on display, but we'll only go to one of them. We'll save the other for another time. Then we'll come back here and I'm going to take you up on your offer for anything goes. Now go put on your overcoat."

"Like this??" she pleaded. "I don't have anything on below the waist. I'm completely exposed."

"That's OK. I'm taking you to a Saturday afternoon amateur show at the strip club across town. By the way, grab a few bottles of water for you to drink on the way there." I told her.

"You're going to make me pee aren't you?? PLEASE DAVE!! Please don't." She begged.

"I'm not going to make you pee. I'm going to make you drink all of those bottles of water and NOT let you pee." I told Mary Ann. "Grab your overcoat and a pair of pumps and let's go show off your pussy."

"Dave PLEASE don't make me do this. I might get recognized. It would ruin me. I meant what I said about anything Dave." She pleaded.

"I have it under control Mary Ann. I have a hood with eye, nose and mouth holes along with a place in the back for your hair to come out. Nobody will know it's you." I assured her.

On the drive to the club Mary Ann drank three bottles of water. I was hoping that might wind up to be a problem for her. I made sure to hit as many bumps in the road as I could and I had her finger herself to get her lust going and to take her mind off of what was about to happen as well as to make her urge to pee greater.

"Open your jacket Mary Ann. Let me see you fingering that pussy of yours. Show me slut." I told her.

Mary Ann obediently unbuttoned her jacket and spread her legs open. She started to rub between her pussy lips and tease her clit. Soon she had a finger inside her pussy while her other hand worked her clit. She quickly added a couple of more fingers and her breathing was picking up and her eyes were closed. Mary Ann was working her way up to a gusher despite all the water.

"You're going to cum soon aren't you slut?" I asked.

"Yeeeesss. It feels so good. Awwww. " She said.

"Beg me to allow you to cum Mary Ann." I told her.

"Let me cum Dave. I need to cum." She begged.

"No." I replied. "Now take your hands off of your pussy. We're a couple of minutes away and I don't want you rung out from an orgasm."

She obeyed me and removed her fingers from inside her pussy and stopped rubbing her clit.

"We'll be there in a couple of minutes. Put the hood on so nobody knows it's you except me." I told her. She pulled the hood over her head and adjusted it so all of the openings were in the right place and buttoned up her jacket.

When we pulled into the parking lot I zipped up the hood and then we walked into the club and registered Mary Ann. There were only four contestants today and Mary Ann was fourth. I bought Mary Ann a large Coke to drink and she also got another glass of water.

The first girl was Latino and her pink pussy really stood out next to her dark skin. The next was a blond haired big titted woman and the third was a good girl next door type brunette. Mary Ann drank both drinks as she seemed mesmerized by the girls body's on stage. I noticed her hand slip under her jacket. Mary Ann was turned on by the girls and I loved it.

Mary Ann walked onto the stage to the tune of "Do you think I'm sexy?" by Rod Stewart. As soon as she took off her jacket and was standing on stage hooded, with a corset, stockings and fuck me pumps with her glistening pussy exposed to the crowd, the answer to the song was "yes." She was dancing as she unhooked the corset and threw it over by her jacket letting her perky little up slopes out to play. Soon she was sitting on the stage with her legs spread eagle showing off her pussy up close to the guys in the front row.

Her hands soon found themselves playing with her pussy. Suddenly, it looked like she was cumming, but it was pee. Mary Ann was sitting in the middle of the stage with her legs spread open while she emptied her bladder on the stage.

"This bitch is pissing herself." One patron yelled out.

"Whore." Another bellowed. "What a dirty slut."

I could tell Mary Ann was sobbing as she sat on the stage in a pool of her own urine while the crowd called her every name imaginable. Yet, she kept her legs wide open showing off her pussy.

The manager jumped on stage and told her to clean it up. "What's the matter with you? Dumb whore. Clean it up slut!!" He demanded. She just sat there crying.

I jumped on stage to help her out. I laid her down and used her long red hair sticking out of the back of the hood as a mop to soak up her pee. I then used her jacket to wipe up the rest. I grabbed her corset and we left.

"What a dirty whore." "Piss slut." "Dirty cunt." Were just some of the insults directed at Mary Ann as I put her piss soaked jacket over her and we walked out to the car leaving the club.

When we got back in the car she took off the piss jacket and was sitting there crying in the front seat. "How could you make me Dave? How could you? You knew that would happen." I don't think that she realized that she was only wearing fishnets with pumps and a hood.

I reached over between her legs and she was soaking wet. Not just from having peed. I stuffed two fingers into her awaiting snatch and could hear her mumble "MMMM Dave," as I fingered her pussy. I was turned on and so was she. I reclined my seat and pulled her on top of me. I quickly undid my pants pulling out my cock. I sat Mary Ann right on top of my rock hard cock and penetrated her wet love hole. I grabbed her hips and slammed her up and down knowing I wasn't going to last too long. I bit down on her left nipple while I fucked her as she pulled my head closer to her chest.

"AAWWWW GOD" Mary Ann screamed out just before I could feel her warm juices exploding onto my cock. That sent me over the top and I came deep inside of her. As she was climbing off of me and getting back to her seat we noticed that the bouncer had followed us out to make sure we were leaving and it looked like he enjoyed the show. I pulled my pants up and drove away as quickly as I could.

The ride home was quite. Mary Ann reclined in her seat and took off her hood. She didn't seem to mind wearing only stockings and heels in the car. Perhaps she was lost in her lust as she was burying her fingers in her pie hole and rubbing my jizz from her pussy on her tits. I slowed down a bit so the show on the way home would last.

"Spread them wide slut and finger yourself." I ordered Mary Ann. She was obedient and worked her snatch hole hard. Stuffing two or three fingers in and rubbing her clit with the other hand. "Don't even think about coming without me saying you can, understand?"

"Yes. Please let me cum again. I'm being a dirty girl for you." She pleaded.

"NO. You'll have plenty of time to cum, but for now stop playing with your pussy and start fingering your ass." I instructed her.

"Awww" Mary Ann moaned as her right index finger slowly worked its way up her ass. Cars were honking and yelling at Mary Ann as well as cheering her on as they could see in the car as they drove past. I made sure to adjust my speed to allow maximum viewing for strangers.

Mary Ann had pulled her knees to her chest so her asshole would be wider and she was jamming her finger in and out of her rosebud. I don't think she realized that I had pulled into a drive through until I placed our order. She quickly came out of her sexual trance and pulled her finger out of her asshole. She reached for her piss stained jacket but I wouldn't let her reach for it.

"Go back to what you were doing Mary Ann." I insisted, "and don't stop until we pull into your garage at home."

"People I know might see me Dave. Let me put the hood back on. PLEASE!!" she begged.

"No Mary Ann. You'll get off on it. Whoever takes our money and hands us our order I want you to look in the eye as you bury your fingers inside of you."

"I can't Dave." She sobbed.

"You can or I'll drive you to where the homeless guys were and I'll let you out of the car just the way you are. Choose slut." I told her.

"aaaah huh huh, aaah,huh, huh" she cried out loud, but she opened her legs and started to finger herself.

I handed the young man the money for our order and he handed me our food as Mary Ann cried and fingered herself.

"Give him a good tip Mary Ann. Turn your body towards him so he can see your pussy better." I said.

"aaaah huh huh, aaah huh huh" she balled as she turned to face her pussy towards him.

"Tell him what a slut you are Mary Ann." I told her.

"aaah huh huh" sniff, sniff "aaaah huh huh" she cried louder. His eyes were fixed on Mary Ann's body fingering herself." aaah huh huh, I...I'm a slut. I can't help myself." She blurted out.

There weren't any cars behind us so I told Mary Ann to cum.

"I aaah huh huh can't aaah huh huh. PPPlease stop Dave."

"Enjoy the rest of your day." I told him as we drove off.

"I did as you asked Mary Ann, but there will be a price to pay for it when we get back to your place slut." I informed her.

"Please leave me alone Dave. Aaah huh huh" Mary Ann sobbed. "You've had enough fun with me. Please stop. Please aaah huh huh."

"Stop it or I'll make you walk home down your street with just your stockings and shoes on." I said.

We ate our food as I drove and Mary Ann was lucky as none of her neighbors were out as we drove down her street and pulled into her garage. I made her remove her fuck me pumps and stockings before we walked into her house. I brought in my duffel bag full of toys. I needed a new bag after expanding my toy collection.

Mary Ann was still sniffling and trying to regain her composure when she said, "I need to shower and shampoo the urine out of my hair." Her hair was somewhat matted down from her own pee.

"I don't think so Mary Ann. Besides pee in your hair is the least of your concerns right now." I told her as I grabbed her left arm and pulled it straight up in the air as I used my right hand to smack her ass as hard as I ever have hit it.

SMACK. SMACK. SMACK.

"AAAAH HUH HUH AAAH HUH HUH" Mary Ann cried out with tears flowing down her face. I pulled out the bar stool from the counter and bent her over it.

SMACK. SMACK.

"AAAAAH HUUH HUUH AAAAH HUUH HUUH" Mary Ann was nearly hysterical.

"Stay bent over slut." I told her as I grabbed my duffel bag. I pulled out two pair of hand cuffs and secured her wrists to the leg of the bar stool at the point where the crossbar connects the two legs so she couldn't move her wrists at all. Mary Ann was still crying her eyes out as I made sure her tits were hanging over the seat of the bar stool and then looked to secure her legs. Fortunately, I planned ahead and had some rope and tied both her legs to the corresponding leg of the bar stool. Mary Ann was helpless.

"By the time we're done Mary Ann, I'll break your spirit and you WILL obey me without hesitation. You'll wish you came for the guy at the drive thru." I told her. "I'm not going to blindfold you or put a gag in your mouth. I'm going to show you what I'm going to do to you before I do it and I want to hear you cry and beg me to stop. I'll be a good sport, however, I'll give you a chance to get out of it. If you suck my cock right now and get me off swallowing every drop and not letting me feel any teeth, then I'll free you and we're done for today. If, on the other hand I feel a single tooth or if you lose a single drop of my cum out of your mouth without swallowing my entire load, then your pain will be our pleasure. Deal?"

"Promise Dave?" she said through her sniffles.

"Promise." I swore to Mary Ann.

"OK I'll try it." She said.

"Try what?" I toyed with her. "I want to hear you say it slut."

"I'll suck your cock." Mary Ann said.

"And?" I questioned her.

"And I won't let you feel a tooth and I'll swallow all of you." She said semi-confidently.

With that, I took off my clothes figuring I wasn't going to need them and smacked Mary Ann in the face with my hard cock. I wiped my pre-cum on her cheeks and waved my cock in front of her mouth and watched as Mary Ann opened her mouth wide and stuck out her tongue trying to lick me. I liked the idea so I let her lick my balls and suck on my cock. I reached under the bar stool and pulled on her nipples while she lapped on my cock.

"It's harder to suck cock without your hands isn't it Mary Ann? You don't have to answer if your mouth is full slut." I joked. She was trying really hard to give me a good blow job so I grabbed her hair to hold her head steady while I face fucked her. I could feel myself getting ready to blow my load sooner rather than later so I pushed Mary Ann's head from behind jamming my dick as far into her mouth as it could go at the same time I reached across the length of her back and gave her ass a good slap. She gagged on my cock just before I shot my load which caused some of my jizz to come out of her mouth and hit the floor.

"Good try Mary Ann." I said.

"Good try? I did it! I used my tongue and sucked as hard as I could. You're right it's tougher with no hands. Thanks for the help Dave." Mary Ann said panting as she regained her breath.

"Look down Mary Ann." I informed her. She spotted the dab of my cum on the floor.

"But Dave I.." she started to say but I interrupted her.

"A deal's a deal Mary Ann." I told her. "You're mine. You didn't swallow it all." I walked to the other side of the stool and looked down at her ass before moving eye level and opening her cheeks and pussy lips for my inspection. I took a deep breath of her pink pie hole and took a quick taste. I did the same with her rosebud taking extra time to trace my tongue around her asshole.

"Time to play with some toys." I told Mary Ann as I reached into the duffel bag. I pulled out a pair of nipple clamps attached to each other with a chain. I put them in front of her face as I snapped the clamps. "What do you think?"

"Please don't Dave. PLEEEASE!" she begged.

I ignored her begging and reached under and pulled and twisted on her nipples. I then positioned myself so I could bite on her nipples. I held her left nipple in my teeth and pulled down on it before giving the right nipple the same treatment. I grabbed her left tit and squeezed it hard forcing her nipple out as far as possible before clipping on a clamp.

"SHIT! That hurts." Mary Ann yelled out. "PLEEEEASE Dave. PLEEEASE!"

I squeezed her right tit extending her nipple before I bit it.

"DAVE. That hurts!!" she exclaimed.

I replaced my teeth with the clamp. "Does that feel better Mary Ann?"

"NOOO" she shouted.

"How about now?" I said as I pulled down on the chain causing her nipples to stretch. Mary Ann was biting on her bottom lip to try and not cry again. I grabbed a weight out of the duffel bag and hooked it on the chain causing Mary Ann's tits to be stretched even further.

"Aaaah huh huh, AAAH huh huh" she cried. I swung the weight to cause her more discomfort. "pppplleeeease DDAve, aaah huh huh, please stop."

"Stop? We've just started Mary Ann. You have a lot ahead of you yet tonight." I said as I took out my flogger from the bag. I showed it to Mary Ann and snapped it in front of her for effect. Then I moved behind her and whipped her ass.

CRACK.CRACK.CRACK. I snapped my flogger against her ass.

"AAAAAAAHHHHH HUUUUH HUUUUH" Mary Ann screamed. She was crying so loud I thought the neighbors might hear so I ball gagged her. Next I snapped the flogger up from behind her to catch her pussy.

CRACK.

Muffled screams were coming from behind the ball gag and tears were flowing down her face.

"I'm going to clamp your pussy lips and tape the clamps to your thighs so your pussy is wide open for a good whipping." I said to Mary Ann as I looked her in the eye. She violently shook her head no. "Well I have something else in mind that is very degrading and humiliating. You're right, we should do that instead." I didn't pay attention to her response as I pulled out my next toy for Mary Ann's abuse. I showed her my enema kit and her eyes opened wide and she shook her head. I wanted to hear her so I took off the ball gag and I took off the weight and clamps from her nipples. Mary Ann cried a little bit when the blood went back into her tits.

As I filled the bag with warm water I could hear Mary Ann say "You can't, you can't give me an enema. PLEEEASE." She sobbed.

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