The Enslavement of My Boss Pt. 02

My boss, Joan, had been promoted and was going to move up the corporate food-chain but had forgotten to take me along with her despite all the sacrifice I had made for her success. During the twelve years we had worked together she had every now and then talked about some aspect of her sex life that had really stuck in my mind. I don't know if she did this out some feeling of trust and friendship or to tease and torment me.

Unfortunately for her I still had the paperwork from one of the times she had stolen then replaced a client's funds. The deal I struck with her was that she would explore the top thirteen things she had said to me or one of my own fantasies and in exchange I would destroy the paperwork; or she could take her chances with the authorities. She had already done one of them in her office, so we were down to twelve.

To be fair to her she did get me a killer parking spot in front of the building like I had requested, but did that make up for twelve years of abuse?

Before going on to her next erotic labor I had waited a couple of months as she had taken some time off for a cosmetic re-freshening, after all you have to look young in the corporate world, especially if you are a woman. She looked great, especially with the breast implants she had gotten. On my insistence he had gone from a pair of cute 36Cs to a pair of attention getting 38DDs.

I went into her office and was greeted about as warmly as the grim reaper. As I latched closed the office door I smiled at her drinking in the sight of her new body. "Well, let me see them," I said.

She looked up from her paperwork and scowled, "Really? Here now?" I reminded her of the Cosgrove files. She got up from her desk and sighed. She started to unbutton her blouse as I watched. Her breasts were fuller than before and were well shaped. I could see even through her bra she had gotten her nipple pierced with the iron ring I had bought her, its weight pulled down her nipple ever so slightly, a constant reminder of her enslavement.

She opened her bra and looked away from me as I looked at her tits.

"Are you going to stare at them all day? Then again why not? Everyone else is."

"I bet you had to buy a whole new wardrobe."

"Yes, especially the bras," she said.

"Well it is another asset for you at meetings. You probably can get them to agree to anything," at this she smiled slightly.

I went over to her and kissed her as I let my hands feel her new breasts.

"We are going out to dinner tonight." I gave her the address as she put back on her bra and closed her blouse; I then left her office unlatching the door on the way out.

In the village we dined on some good Cuban food and had a drink or two. Then we walked down the curved streets to a locally famous sex shop. The counter girl, Amy smiled at me and looked Joan over.

"I have it right here!" she said smiling her big toothy smile as she handed me a shopping bag with the items I ordered on line.

As we took a cab ride to my place I told Joan that Amy actually knew her. Joan asked from where, I smiled and scolded her for not remembering.

At my place we had some more drinks. I told her she looked fantastic but now she would have to undress. I went behind her taking her blazer and carefully putting it over a chair. Then as I did earlier I slowly undid her blouse but this time I faced her towards a mirror she could watch herself being undressed, one button at a time.

Her blouse soon joined her blazer on the chair. I pressed against her nice round behind as I undid her bra letting her breasts bounce out. I cupped her tits giving them a light squeeze as I kissed the back of her neck. Her ass thrust against me lightly. Breaking the spell I moved away from her.

"I want you to put this on," I said.

"What, are you serious?" she said as took the lingerie out of the bag. It was a crotchless black lace catsuit. I told her I thought she'd look every sexy in it.

I put the bag on the coffee table. "It was a rainy night, we were in a bar in the airport waiting for our flight back to New York from the conference. You had told me that you had never used a vibrator or sex toys as you were afraid you would become addicted. The image stuck in my mind, the moment you said it I pictured you shaking as you played with one, having orgasm after orgasm as I watched. Well this bag has several of them and tonight you will use them all." In truth I think some of her rejection of sex toys might have come from her upbringing rather than an aversion to becoming addicted.

She started to protest but knew it would not help,. "I can't believe I am doing this," she muttered as she kicked off her shoes and undid her skirt. "Must you watch?" she said as she took off her pantyhose and panties, I nodded back that I did. She took bodysuit and put it on. Even the noise it made when she slid it on was sensual.

"I can't believe this," she muttered again as she turned around to let me inspect her in her lingerie. I smiled my approval. I loved the way it accentuated her ass and curves. I had her come over to me and I pulled down the top slightly letting her breasts tumble over the top.

"Are you going to fuck me?" she asked in a meek but sexy voice and I wondered if it was an invite or a question. I told her we were not up to that fantasy- yet.

"Now before the toys I want to see you play with yourself without them. But first come here," I sat on a chair as she sat on the couch across from me, "If it helps close your eyes, that's it."

I told her to spread her legs and rub herself, she hesitated so I got up and sat next to her, I kissed her and guided her hands down to her pussy.

"Rub yourself, that's it!" I told her, then kissed her again. "Show me how sexy you can be."

I played with her tits some more, I told her to keep her eyes closed regretting I had not thought to buy her a blindfold. I lifted one of her tits to her mouth and had her suck on it, then on the other as she fingered herself. "That's it! Now lick your nipples and make them nice and hard for me," I told her how sexy she looked doing it. Five years ago I would have never dreamed I'd actually be doing this with her; or more precisely I had dreamed it but did not think it would come true.

With a soft moan I knew she had reached a small orgasm from rubbing her light brown haired pussy. She'd dyed her hair blonde (she said it coved the gray better) but she had not taken care of herself down there, at least not yet.

I asked her if this was the way she always masturbated and she told me yes but that she did it in the bathroom, alone with her hand; I told her that was going to change.

I went across the room taking out of the bag the smallest of the vibrators. Amy had unboxed them for me at the store and had made sure they all had batteries in them. I had told her on the phone as a joke not to test them but she giggled saying she already had one of her own inside of her.

The vibrator was purple with a ring at the top to slip your finger through. I told her to be careful, that like some hot peppers sometimes the smallest ones could be the most powerful.

"Wait one moment! I have something else for you," I said as I took out of the draw of an end table a black vinyl bondage hood.

"What are you doing with that?" she demanded to know a bit shocked.

I told her it was my own personal kink (which it was) and also I wanted her to wear in case I wanted to take a photo as a souvenir. She did not want to put it on but I reminded her again of the Cosgrove file which could undo her whole career. She thought about it and changed her mind. I helped her lace the back of the hood on and buckled the neck piece locking the eyelid in place with a small padlock.

"Now you look like the proper sex robot," I said as I kissed her. She stared at herself in the mirror and realized the loss of her own identity might free her to reach even greater erotic heights.

I placed the vibrator it in my slave's hand showing her how to turn it on. It buzzed in her fingers.

"It tickles," she giggled as she brushed it against herself, then she hit just the right spot and almost instantly let out a soft moan, her breasts heaved slightly and her nipple became nearly rock hard.

"That's it! Work it right over there, lightly," I said grabbing her hand

"Oh fuck! I am going to be become addicted to this! Aren't I?" she said almost dreamily as she came.

"So what is wrong with that? I can think of worse things than being addicted to pleasure."

"No, to vibrators."

"Don't worry about it," I told her as I leaned forward to kiss her, it was odd but sexy to kiss her with her bondage hood on.

Moaning I could see her learning how to pleasure herself with the small vibrator. Her back arched slightly as she came yet again as her breasts jiggled slightly.

I got up and brought the bag over to her taking out of it a bigger vibrator. I worked it around her pussy while she worked the smaller one at the top of her clit. I had her wrap her fingers around the bigger one and told her to push it into herself noticing how wet she was.

"That's it work your own pussy, become addicted and make yourself cum. Later if you are a good girl I will tell you where you know Amy from."

"Ugh! Oh! Oh! Oh!" she moaned as the vibrators brought her to orgasm after orgasm. She pushed the bigger one deeper into her pussy while I told her to put the smaller one against her nipples.

"Oh shit! Oh shit! Oh shit! Who needs a man!" she muttered then laughed.

I told her I wanted to her to stick her finger into her pussy and then suck on it. She put down the vibrator and did so almost instantly, I made a note to put off spanking her until another session as I juggled my mental list of things I had planned for her to do.

She did it for me several times making a big show of it; then she picked back up the vibrator and worked it inside herself, her eyes tight little slits as she came over and over again.

I opened my pants and pulled out my cock and walked over to her.

"Are you going to fuck me?" she pleaded this time. I told her not today.

She grabbed my cock and jerked me off while she played with her pussy with her toy.

"Please fuck me! It does not even have to count against that list of yours."

There is a certain state of pleasure in saying yes and there was a certain state of pleasure in saying no. This time I took the latter.

I did reach down and fingered her, enjoying its heat and wetness. "At least stick your finger inside me," she begged. I slid my pointer finger into her now thoroughly slick cunt and she squeezed it with her muscles. I had to summon up all my will power as that was the closest I came to giving up on my plans and fucking her.

Instead I held fast, but barely, to my resolve and fingered her making her tremble. "Cum on me! Cum all over me!" the voice said trembling, the same voice that usually commanded me to get a report or call someone up for her. Despite my resolve the human body has limits and I had soon reached mine.

I groaned and laughing she pumped my cock all over her tits and stomach. She was very good at milking another wave of pleasure from me even after I had finished. Then she bent forward and without being asked to she used the gentle suction of her mouth to drain the rest of my cum from me. When she was finished she gave my cock a long, almost romantic kiss before letting it go.

I closed my pants and directed her to get up on the coffee table. I took out one last item; it was an eight inch realistic dildo with a suction cup on the bottom. I handed her the small bottle of lube as I stuck it onto the coffee table.

"Well now, show me how you would have sex with me," I said.

"Okay. Honey stick it in me!" she said as she squatted down onto the dildo. She used her hands to hold it steady as it entered her."

"Oh yeah! Fuck me!" she said as she rode it up and down. I watched her pussy lips drag along the thick rubber cock as she went up the shaft as she added her juice to the lube already on the cock.

Through her mask she looked at me and said, "You like watching me get fucked don't you?" shifting the narrative from her pretending to fuck me to her fucking someone else as I watched. I told her I did, then I went over and kissed her.

She managed to play with her tits as she fucked the dildo, I took a smaller vibrator, one that was nearly pencil thin and put some lube on it. I told her to hold still as I turned it on and pushed it up her ass telling her to hold onto it as she fucked the dildo.

This new addition made her fuck the rubber cock even harder, and yes I took out my phone and took several pictures of her humping the cock. At first she was shy, but then she realized with the bodysuit and mask there is no way anyone could really identify her and knowing this she put on show. At one point she stopped with the dildo buried deep in her and sucked on her own tits (something I find highly erotic) and I took several more shots.

I was afraid the table would break as humped the shit out of the cock begging me to fuck her until she came so hard she almost fell off the table. "Oh fuck!" she said as she laid down on the table panting as she shifted to let the dildo slide out of her pussy.

I let her rest for a moment or so, then I took out of the linen closet the surprise, it was purple, a foot long with a handle for someone else to use.

"No way you are putting that in me!" she said getting off the table. I went behind her and unlaced and unlocked her mask, her hair was matted from her sweat. I kissed her and said it was the last thing for the night and that if she was good, really good I would tell her one of the things I have planned for her.

"Really?" she asked in a submissive voice that delighted me.

"Just one thing."

"What?"

"When you address me at home, like this you shall call me master," I said swatting that fat ass of hers. She tried to pull away and I slapped her butt a few more times until she nodded her submission.

"Now lean over that couch," I told her as I squirted some lube onto the new toy which I told her she could also call "master," also. I turned it on and it shook my hand as it vibrated.

"Ugh! Oh fuck! You mean it!" she said as I slid it partway into her; I let her adjust to its size before working it in and out of her. Her moaning and groaning got so loud I wish I had turned on the stereo or television. Her body stiffened and relaxed as she came in waves. "You are ruining me! Ruining me!" Then she whispered, "Please don't stop!"

Her ass rocked backwards pushing more of it inside of her as she came still harder. Then she pulled herself off of the dildo and turned around and kissed my face, lips, my neck. "Please fuck me master please! It does not have to count! Please I won't tell! Fuck me!"

I held her and threw the vibrator onto the couch, for a second I wondered if I had gone too far. She bit my ear lobe none too lightly telling me I owned her as she cried. I kissed her and fingered her as I told her to relax. I could feel her pussy clench my finger but lighter with each minute as her breathing returned to normal.

After she rested some I helped her get dressed keeping her panties as a souvenir and called a car for her,

We went out into the cold night air as we waited for the car service car to arrive. In a reusable shopping bag was the bag of sex toys for her to take home and continue to use as part of her training.

As we waited for the cab I told her about time I was trying to talk my wife into having sex with a much bigger endowed man as I watched, and another time I had the more conventional fantasy of her with another woman. Maureen was redheaded like the actress she was named after. I found that most of the redheads I had dated could be divided into two groups, those who would shut down the bar and those who are devout near prude homebodies. Maureen was the latter, but I always hoped to make her into the former.

"Now who is Amy?" she asked but the car had arrived.

I slipped a small package into her coat pocket, whispering it was for her left nipple.

"What's next a tongue stud?" she asked worried.

I just smiled at her as she got in looking a little bit worried.

After she was gone Amy came out of her car. As she walked towards me I tried as always to figure her out. Small and blonde she was part Asian and something else that I could never quite figure out, nor did I really need to. She gave me a kiss as her hand quickly gave my cock a squeeze.

"I see it went pretty good!" she giggled.

I told it had. I asked her if she had any problems coming over to meet me. She told me no, reminding me her and Erica were not exclusive.

"You know she still wants to hump you, and so do I" Amy said as we went inside my apartment. Changing the subject she said "I think she is at the point she wants to include me in the deal," she said referring to her steady girlfriend Erica.

"Really? You mean big bad Erica wants to bargain? What is this world coming to?"

"Well if it comes to that, you better act like it is our first time," Amy said giggling.

She gave me a nice kiss as she pressed her body against me. "Are you sure you are up to it?" she said looking around the living room with the cum stained body stocking and bondage mask on the coffee table. I picked her up and carried her to the bedroom telling her I'd have double or triple coffees in the morning to stay up if I had to.

Later in bed she asked me what I had planned next for my boss. I laughed and told her something that would involve her and Erica and some of their friends if they were available.

Laughing she kissed me and said she'd have to check her calendar.

I told her not to make it too soon, as I wanted Joan to think and worry a bit about what was going to happen next.

Amy laughed saying I was a cruel man, I told her it was a cruel world out there. Seeing I was getting serious again she slammed me with a pillow.

Over the next few weeks Joan came to work looking exhausted every day, she told me in private that she had been playing with the sex toys I have given her, and a few that she had bought on her own. I smiled thinking how this might get her ready for the next few tasks I had lined up for her.