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.
