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My Special Employee

One of the most fantastic women to come into my life was Kelly. A bartender I know was dating her and introduced us on night when he was working. She is a tiny redhead with green eyes and freckles, all of the traits of her Irish heritage Just 5’ 1” and under a hundred pounds. Definitely what you would call petite except for the most massive C cup breasts with nipples that are almost always erect.

After Kelly and my friend had stopped dating, I ran into Kelly again in the same bar. He was a player and never dated anyone for more than a month or so. We talking and really enjoyed getting to know each other better. The evening ended with my walking Kelly to her car, a very nice good night kiss and both of us agreeing to another date very soon. I called the next day and we set a date for dinner. She wanted to meet me at the restaurant.

I arrived a few minutes early and right on time she walked through the door. She was wearing a cream-colored cashmere sweater and pleated dark brown skirt, and heels. Her shoulder length red hair was curled and bounced with every step along with her massive breasts. Kelly was showing just the right amount of cleavage. She looked like a Hollywood sweater girl. I do not remember what we eat or even much about the dinner itself. I know I was in awe of her beauty and personality.

We stopped by a club for an after dinner cocktail. Ultimately, the date ended at my condo. Once in the bedroom, I began undressed her and enjoyed exploring her body. Underneath the sweater and skirt were a lacy white bra and matching thong. Removing the bra I found her areola were large and the color of dark caramel and her nipples just kept getting harder and harder the more I played with them. While she has a flat butt, what there was of it fit nicely in my hands. I slowly undressed her over the course of several minutes of kissing, caressing and foreplay. Now naked, she removed my shirt then dropped to her knees, removed my pants and began giving me a very talented blowjob. I wanted did not want to come just yet, so I lifted her to her feet and then placed her on the bed. The most interesting surprise came when she told me that she would probably not come our first time together. With that, I was on a mission to prove her wrong and I did. I slowly kissed my way down her body to her neatly trimmed patch of red hair just above her pussy. I would like to say at this point I pride myself on my oral techniques. I figure I must have been a lesbian in a previous life. A few moments later, she experienced her first orgasm of the night. I slid up on top of here and rock hard cock easily entered her very wet pussy. We spent the next hour entwined together, as we explored a number of positions during which time she came for the second time. Finally we finished with her on top, riding my cock until us both climaxed. She rolled off and we both fell quickly asleep.

Due to my work, we spent the next couple of weeks apart. When I returned to town, I found that my secretary/bookkeeper had quit in order to take care of her Mother. I own a small company with a family like atmosphere. Almost everyone who works for me, I already knew before I hired them, or were friends of an existing employee. I began putting the word out I was looking for a replacement.

I met up with Kelly a few nights later for drinks and low and behold, Kelly had lost her job at an accounting firm as well. I told her that the timing was amazing. I was looking for someone to work for me. I explained to Kelly what the position entailed, the salary and benefit package. Kelly was very interested. I told her that there was a tough decision we had to make. Did we want a work relationship or a personal one? I told her that my priority was to find someone to take care of my office and felt that she was more than qualified if she was interested. I remember telling her I needed an assistant more than a girlfriend. She said that being a single Mother finding a job definitely had a priority. I also explained in spite of trying to keep things on a professional level that I would still look forward to an occasional hug. She agreed providing the hugs were part of the benefit package. That is how Kelly came to work for me.

As I said, I own a small company, and except for Kelly, my employees are in the field most of the time. My mornings are spent out checking on the various job sites and the afternoons are usually in the office. Kelly duties require her to open the office and take care of things until I arrive. Immediately she jumped in a made many improvements around the office. We would often share lunch in my office from one of then many nearby restaurants. As time progressed, we got to know more and more about each other. On more than one occasion told her that I was very glad she had decided to come to work for me and I was.


One of the office computers developed a virus problem, when one of my other employees was using the internet after hours to browse porn websites. In order figure who was responsible and prevent future problems, I installed computer-monitoring software on all the computers. It took only a few days to flush out the culprit and his web surfing was promptly curtailed.

Up until this point everything between Kelly and I had remained business like. Except for the almost daily hugs hello or goodbye. All that changed after I completed a routine check of her computer. I found that she had been looking at some interesting websites on the internet. She had been visiting sites dealing in erotic stories. Much of what she had been reading dealt with submissive females. A couple involved a secretary and her boss. I began to think of possible future opportunities.

A major change occurred when I received a call from Kelly one night asking if she could come spend the night at my place. It seems that she had gotten into a major argument with her roommate and needed a place to stay for the night. When she arrived, she had a huge suitcase with her. After providing her with a glass of wine, we sat down and I asked her what was going on and where her kids were. She said her kids were at their father’s house. They have a joint custody thing. Kelly told me the roommate had moved her unemployed boyfriend in with out asking. He was not contributing to the rent or expenses and ate like a horse. She felt like she was being confined to her bedroom. When she finally confronted her roommate there was a big blow up. The roommate told her that was the way it was going to be and if she did not like it, she could move out. I told her she was welcome to stay as long as she needed. Kelly threw her arms around me in a big hug.

After discussing her finding a new place and other things for a while longer, she excused herself to use the bathroom. The shortest route to the bathroom from the living room was through my bedroom and that was the one she took. What got my attention was that she picked up her suitcase on the way and took it with her. I figured that she was not planning to sleep on my sofa, which was fine with me.

After we finished off the rest of bottle of wine, it was late and the next day was a workday. I suggested we head to bed. I normally sleep in the nude, but figured I would keep my briefs, on depending on her attire. I offer her the bathroom first and then took my turn. When I emerged, she was already in bed. I noticed her shoulders were bare, so that gave me some idea. On the floor where she had piled her clothes I saw the top two items were her bra and panties. I walked around the bed to the other side, stripped all the way down, and slid under covers.

She immediately rolled over toward me and asked if she could have a good night kiss and hug. She snuggled into my arms and gave me a long deep kiss after which she told me she was so lucky to have me as the major stability in her life. I enjoyed the feeling of her ample breasts pressing into my chest. My arm slid down gently running her bare back working my way down and confirmed that she was nude. She at the same time began caressing my chest. We both knew that we would not be falling to sleep anytime soon. Her hand soon found its way to my rapidly hardening cock. At the same time, I began playing with her nipples with my other hand.

Remembering her interest in submissive situations, I decided to take charge of the situation. I directed her head down and told her I want to feel her lovely mouth wrapped around my cock. She quickly complied. I then lifted her over my body, so that we were in the sixty-nine position. I proceeded to explore her pussy with my tongue. I distracted her so much that she stopped sucking my cock and racked into and orgasm. I then pushed her forward on to her hands and knees so I could fuck her from behind. Her face was buried into the bed, as I pounded my cock into her roughly feeling my balls slapping against her clitoris. After a several minutes of this, I pulled out and lay back down. I told her it was her turn to do some work. With that, Kelly climbed on top of me and began riding my cock. This is my favorite position as it allows me free use of my hands and I can control the tempo by either raising my legs to slow thing down or thrusting my hips to increase things. I took full advantage of this with Kelly. I was massaging her huge breasts and toying with her nipples. I noticed that when I pinched them that Kelly seemed to close her eyes a bit tighter and at the same instance, she took a deep breath as if she was enjoying the sensation. Repeating this several times, I confirmed that this was same. I decided to try another form of mild pain. I cupped my right hand and slapped her left cheek of her butt. Kelly threw her head back and let out a low “Oh Yeah!” I rubbed her bottom where I had slapped. Then I did the other cheek with my left hand and she did the same thing and then I rubbed it as well. I alternated slaps with either hand until each one had received three slaps. I told Kelly I wanted to come for me and she did. I shot my load into her as she was in the last throws of her orgasm. As I was finishing squeezing my last drops, I massaged her butt and she collapsed on my chest. After a few moments, I rolled us over so we were lying on our sides facing each other my arms wrapped around her. Kelly the asked “How did you know I would enjoy being slapped?” I told her, “It was just a feeling I had.” She smiled and kissed me softly and deeply. With that, we drifted off to sleep.

In the morning, we headed off to work. I was off to check the jobsite and her to the office. When I came in a few hours later I, there was a very sweet thank you card on my desk from Kelly. I came out and told her thanks and got a big hug, then proceeded to get back to work. A few hours later, I went on line and emailed her a kinky e-card, which showed a woman being spanked with a caption line about the pleasure being mutual. Her reply was an even more erotic card on a submissive theme. It stated that I was in charge. I sent her back an email and asked if there was anything she felt the need to clarify. Kelly responded with the following email.

“Since facts are facts...and...Rules are rules...I also have my own personal rules, which I have learned, work for me throughout my sexual life and do not deviate from...it's to cover my ass.

1. Any and all personal info and/or sexual relationships stays between you and I...or if agreed upon in advance...specific information shared with any other party will be allowed.

2. I expect any personal encounters between you and me to be considered completely separate from our business relationship. I do not want to ever feel uncomfortable at work or to be treated as less of an employee.

3. I expect the same personal respect from you as you have always given me since day one...I, of course, have and do respect and admire you and I don't want that tarnished.

4. No dropping innuendos around my fellow employees...they respect me; and I them...let's keep it that way.

5. I will do out of town trips, as long as I am given prior notice to make arrangements for my children.

6. No pressure means "no pressure"...I do not ever want any regrets the next day.

7. Keep it fun...It's not a job or work.”

The game was on. I sent her hack an email that stated there was going to be a new dress code for all female employees. She was the only female.

Here are the new rules for your attire.
1. Dresses and skirts are definitely preferred over shorts and pants.
2. Button front or loose fitting tops is preferred over tee shirts.
3. Heels, dress boots or sandals.

What is or is not underneath is more important:
4. The preference is no underwear whatsoever, especially when in dresses or skirts
5. The only acceptable underwear is thongs or g-strings.
6. Open or demi cup bras are preferred.
7. No pantyhose at anytime.
8. Bare legs or thigh high stockings depend upon time of year and occasion.
9. You are to keep your pubic hairs neatly trimmed or shaved.

She sent me back an email agreeing to try to comply, but did not have many clothes that would meet the dress code. I knew her finances were limited and understood when she said would be more than happy to wear anything I purchased. She provided me with sizes and pointed out that dresses were extremely difficult for her to find because of her small size and large bust. Skirts and blouses were easier.

I decided to let Kelly get started, gave her some money, and told her to take the rest of the day off to go shopping. I would see her later at my place. After she left, I went on line and did some shopping for her myself. A found her some shelf bras, so her nipples would be visible. I ordered three in red, white, and black with matching g-string thongs and several pairs of thigh high stockings in both nude and black.

I arrived home before Kelly. She came in with numerous bags. I asked her if she wanted to put on something new and go out to dinner or I could cook. Of course, she opted to go out and asked for a few minutes to shower and get dressed. A short time later, she emerged in in a flared beige skirt with a matching jacket over a dark brown button front lacy blouse showing some very nice cleavage and nudes stockings with tan heeled sandals. Her long red hair hung freely to her shoulders in natural curls. Very classy and very hot. I complimented Kelly on her excellent taste. She said there were two other tops, a skirt, and a pair of black high heels as well. She was also very good as stretching a dollar.

After dinner, we return home and she asked if I was ready to see the rest of her outfit. With that, she took my hand, led me into the bedroom, and sat me on the bed. Climbed on my lap, gave me a long deep kiss, and then said. “Thank you for all you have done for me. I had the best time today shopping. I kept you in mind every time I tried something on. Now you get to undress me.” So I did. Off came the jacket, and then after some hugs kisses and caressing it began to unbutton her blouse, exposing a sheer lavender bra. Her areolas were very visible through the bra. I then unzipped the skirt and she stood and let it drop to the floor revealing a matching thong and thigh high stockings. She did a couple of slow turn a rounds asking if I approved. I stood up and pulled her into my arms. After another kiss, I reached around, unhooked her bra, and began playing with her lovely breasts and nipples. Kelly began to unbutton my shirt, after pushing it off my shoulders she went to work on my belt and pants. I kicked off my pants, sat down on the bed and removed my shoes and socks. I then reached out and pulled Kelly on to the bed. I slowly removed her panties. I discovered another surprise. Kelly had shaved her pussy very bare. I left her in just the stockings and heels. I removed my underwear and then dropped down and began enjoying the taste of her new look. After bring her to an orgasm, I had her stand up, turn around and bend over so I could fuck her from behind. I also took the opportunity to spank her lovely ass a few times turning it a nice shade of pink. Between her vocal encouragement and tight pussy, I shot my load as she came in a matter of minutes. Kelly asked if she could now remove her heels and stockings. I said yes, as we should get some sleep as tomorrow was Friday and a workday.

She was still getting ready as I left for the jobsite in the morning. I would have to wait until I got to the office to see her attire for the day. I rushed through my morning “To Do List,” in anticipation for what was waiting for me at the office.

Kelly did not disappoint me. She came in to the office the picture of a proper businessperson with a flair for fashion. She was wearing a charcoal grey pleated shirt, a white blouse underneath a black ¾ length long sleeved sweater with black stockings and classic black pumps. A lovely black & white print scarf tied behind her neck pulled her hair back. She did a little modeling turn and the slipped off the sweater. I had not noticed earlier that the blouse was sheer. My attention was immediately drawn to the fact she had not worn a bra as her nipples were clearly visible underneath. Kelly asked if I this met the new dress requirements. She apologized that did not have enough money left from my shopping trip for another set lingerie. However, she thought I would enjoy the tact that in addition to no bra she was not wearing panties either. She said the sweater was necessary in case someone came in. We seldom get customers at the shop, but are often getting deliveries from suppliers. When she first started I told her for safety purposes to keep the front door locked when she was alone. While we have never had any problems, we are not located in the best of neighborhoods. I could see it now being locked all the time in the future for other reasons as well.

I took a seat behind my desk and told her that I approved of this outfit as well; I especially enjoyed the underwear or lack of it. It was also appropriate for some additional behavior modifications that I would like. I told her to go take a seat on the couch that faced the desk, but stopped her just before she sat down. I told her to lift the back of the skirt so that he bare bottom was against the cushion. I then instructed her not to cross her legs at the knee, but rather at the ankles leaving her knees apart. I told her that she should get use to sitting that way, so I could enjoy looking at her up her skirt. It would also make her more available to me when I was seated next to her. She agreed to comply and work on it. Kelly sat down on the couch as instructed.

I told her that I though it would be an excellent idea that we start keeping the front door locked all the time. She should create a sign for people to knock for entrance. There were already Venetian blinds on the windows and glass front door, which I said would have to be closed a bit further. Kelly desk was in the front office and my office was immediately behind it. My office door aligned up directly across from the front door and the end of the couch that Kelly was sitting on. Anyone at the door could see her profile sitting on the couch. The phone rang and it was time to get back to work. I told her I was very pleased and we would continue more later.

While later, Kelly brought me the daily mail. Rather than handing it to me across the desk, she came around and stood next to me. I took the opportunity to reach out, slide my hand up under her skirt, and enjoy feeling her bare butt. In the next moment, she was on my lap and we were going at it. I was playing with her pussy and she was rubbing her butt against my hardening cock contained in my pants. Finally, she stood up turned around and began opening my pants to free my cock. Taking it in her hands, she dropped to her knees and gave me the most fantastic blowjob. I enjoyed it so much that I did not stop her and just released my load in her mouth. She swallowed every drop and licked me clean. I helped her to her feet and placed her on the desk, spread her legs and lifted her skirt exposing her pussy. I then proceed to return the favor and brought her to an orgasm. It was the first of was would become our regular afternoon sex breaks.

Later in the day, she said that she was going to return to her place that night to try to work out the roommate situation. Part of me was disappointed about not seeing her, but I knew it was the weekend and her kids would be returning as well. At the end of her workday, she came in, gave me a big hug, a kiss good-bye, and thanked me for all I had done for her. When I checked, my email near the end of the day there was one from Kelly. She must have sent it right as she was leaving the office. It read

“I have come to the self-realization that I must break free from the restraints of my parents over protective introverted, self-conscience, cult- religious sexually formative years in my life...I have determined a particular place and position when I'm away from my desk would help train me (or untrained). I am suggesting bringing the wood stool from the warehouse into your office. I enjoy wearing your required clothing and in the future will sit on the stool in the appropriate position. Let me know, K”

The stool she was referring to was a basic walnut wood bar stool with a swiveling top the legs had been cut off, so that it was less than two feet tall. For quite a while, it had sat in my office in the corner near my desk. I did not even notice it was not there any more. One of the guys must have borrowed it to sit on while working on a project back in the warehouse. I n the past when Kelly wanted to discuss a problem, she was having or something serious with me, she would pull the stool closer to the end of my desk and sit on it. This was because she did not want to separated by the desk and space across the office to the sofa. I immediately got up, found the stool, and placed it back in my office.

Monday arrived and I had spent the weekend think of how to proceed with Kelly and her desire to explore her sexuality further. When I got to the office, we started things got right to the business side of things. She was in a simple, short “A” shaped dress that hugged the curves of her body very nicely with stocking and heels. Because of her erect nipples, I could tell that she was not wearing a bra and there were no panty lines. There was much to be done and little time to play. Late in the afternoon the ups truck arrived with a package. Usually the deliveries are work related and I take care of opening them. This package was the lingerie I had ordered the previous week. At the end of the day, I called Kelly into my office at the end of the day. She came in, lifting the back of her dress she and sat down with her bare butt on the stool crossing her legs at the ankles. I gave her the box and told her to open it. Her face lit up as she removed the tissue from each item. She stood up unzipped her dress and let it drop to the floor. Kelly stood there in just her shoes and stockings. She slipped on the black g-string and then the matching shelf bra. It was sculpted in such a manner that all her areola was fully exposed. She looked stunning and I told her so. She asked if I wanted to see the others now. I said, that would not be necessary, as they were just different colors. She crawled into my lap and gave me a long wet kiss. I took advantage of the benefits of the new bra and lightly rubbed her nipples against the palm of my hands until they were both extremely hard. I brought one breast to my mouth and enjoyed nibbling and sucking on her nipple. My free hand found its way down the front of the g-string finding a very wet and waiting pussy. Kelly was rubbing hand against the front of my crouch massaging my cock through my pants. I lifted her onto the desk and unzipped my pants to free my cock I did not bother removing the g-string, but pulled it to one side and proceeded to fuck her until I shot my load inside her. Somewhere along the way, she had come too. We cleaned things up a bit, with her slipping the dress over the new underwear and we closed up the office for the day.

In the past she had always sat on the sofa in my office, I now noticed that she had began using the stool instead always sitting with her bare butt on the stool and her legs open so I could see her pussy. She was clearly making an effort to conform to my desires.

I wanted to find out more about Kelly’s previous experiences, as well as how much she was willing try. I found a questionnaire on one of the on one of the alternative dating sites and emailed it to her. I told her that turn around was fair play. After she filled it out and returned it, I would share mine with her as well. At the end of the next day, she emailed me her responses. Once again, this was the last thing she did just before leaving. Therefore, I did not receive it after she had left. In reading it there was only one surprise. She had experienced sex with two guys at once and was not interested in repeating it. Other than that, her past was very vanilla. She had never been photographed or video taped in the nude or having sex. The last part was a long list of sexual activities. It covered most of the various sexual activities and several extreme kinks as well. It asked which she had experienced, did she enjoy it. I she had not experienced it, would she be willing to engage in the activity or not. Her responses said that she had enjoyed most of her previous experiences and that there was very little that she was not open to trying. She did have limits in some of the extreme kink area. I now had some good information to work with. I sent her a mildly kinky BDSM e-card thanking her for completing the task so promptly. As I had promised, I also sent her off my responses as well.

The next day I found a very submissive e card waiting for me, which showed a naked woman kneeling with her hands bound by photographer Craig Morey. Kelly said that was something she would like to try.

A few days later, I sent her out to pick up lunch for the two of us and we ate at the coffee table in my office. Afterward we were cuddling on the couch; this led to my massaging her shoulders. That moved on to my undressing her and ultimately massaging her pussy to orgasm. At the peak, she was pulling on her nipples. She helped me remove my clothes climbed on my lap facing me and rode my cock until I came as well. After we cleaned up and returned to work, I went on line and order some new toys: a bondage starter kit that included soft wrist and ankle restraints, a blindfold, as well as some nipple clamps.

Afternoon sex became a regular weekly ritual. After on session I informed her that I would like to take some photographs of her in both sexy clothing and nude. She replied, “I'm camera shy, so you'll have to work with me on that one. I don't think I'm very photogenic, but there's always room for improvement.” I went on to tell her that she would need to become more comfortable with her body and who she wanted to become. In preparation, I would like her to start spending more time in the nude.

I told her from now on at least once a week she was to undress out front and then come into the office and sit on the stool for an hour. I told her to use this time to think about whom she was and what she wanted and expected as a submissive. That I might or might not have sex and for that matter, we might not engage in any conversation. She was to be there for me to enjoy as I pleased. An hour later in she walked totally naked and sat down on the stool. I just went on with my work. When I looked over again, her hands were resting on her thighs palms up and her eyes were closed. It was almost as if she was meditating. After about 45 minutes, I decided to change things up. Her eyes were still closed when I reached into the small office refrigerator behind my desk and got a cold soda. I then leaned over and pressed the can against one of her nipples. She immediate jumped with a surprised look on her face. I then applied it to the other nipple. Both were immediately gumdrops. I smiled and said I was not done yet and placed the cold can on the stool between her spread legs and right up against her pussy and held it there as she squirmed. My cock was now as hard as her cold nipples. I moved the can away opened it and took a long gulp, then stood and lifted her into my arms and took her to the couch and laid her down. I dove in right between her legs lifting them over my shoulders to give me better access to her pussy. I licked, sucked, kissed and nibbled until she was in the throws of a massive orgasm. I then stood up opened my pants and had her suck me off, taking every drop of my load.

On the next occasion, I immediate blindfolded her and left her that way for a full hour. I totally ignored her for the entire time, but enjoyed the thought that she was sitting there, totally naked for me. For the next few weeks, she repeated the exercise at least one a week with a variety of variations. I used the wrist and ankle restraints to secure her hand behind her and her ankles to the outside legs of the stool for a half hour. Then had her kneel on the floor and using several carabineers connected her wrists and ankles together. I had her give me a blowjob this way. She could use only her mouth. Kelly was fantastic. One time there was a knock at the front door. I left her there while I dealt with visitor. I deliberately left the office door slight ajar. Her clothes were all neatly folded and sitting on her office chair in the front office. Later she said that she had spent the time trying to figure what to do. Hiding under the desk was the only thing she said could figure out and she was thankful that it was not one of the other employees.

A couple of days before Christmas I called Kelly into my office. I had numerous presents for her to open. There was some clothing for work, a couple of outfits that is referred to as club attire, but is more the kind of stuff that strippers wear. I also had a couple of different vibrators: one a small traditional another was a larger rabbit with numerous options, and the last was a vibrating egg. After she opened everything, she asked about batteries for the toys. I went out in the warehouse to get some. Reentering my office I found Kelly had undressed and was lying on the sofa. One leg was resting on the back of the sofa the other was on the floor. I was looking straight into her freshly shaven pussy. The fingers of her right hand were already rubbing with her clit. “I just could not wait for you to get back, I was so excited.” I Picked up the small vibrator off the coffee table, inserted the batteries, and handed it to her. Kelly immediately turned it on and started using it, while I put the batteries in the rest of the toys. I sat down on the coffee table, turned on the rabbit, and then moved Kelly’s hand containing the smaller vibrator from her pussy. I slowly began to insert the rabbit into her pussy, and then began increasing the speed of the various options. Kelly took the smaller vibrator and began holding it up against her nipples. It was only a matter of moments until she was spamming in a massive orgasm. After she caught her breath, she sat up, undid my belt and unzipped my pants. I moved over to the couch. I then picked up the egg and put it into her pussy, but did not turn it on. I wanted her to get use to the feeling of having it inside her. Besides I was distracted her guiding my cock into her lovely mouth. As soon as I felt myself building to an approaching climax, I turned on the control for the egg. This intensified Kelly’s efforts and I exploded a load cum down her throat. As she was trying to lick me clean, she began to shutter in another orgasm. After we straighten up, she stored the toys and special clothing in her employee locker in the restroom in anticipation of future use. Then we called it a day.

Our relationship went on for over nearly three years lasting until I sold the business. There were major changes taking place in the industry. These were going to require substantial capital improvements and I just could not justify the expense, so when I saw the opportunity to sell I took it. That was five years ago. I still see Kelly from time to time, but regretfully we have never had the chance to play again. The thing I really miss most being in my office chair and having Kelly come in a sit on my lap, leaning back against my chest with her lovely bare breast in my hands and feeling her nipples getting hard against my palms as my cock gets hard against the crack of her ass. I took the wood stool with me when I cleaned out my office and it now sits in the corner of my office at home. I often envision having Kelly sitting on it once again.

End of Story