To say that my dreams came true was a gross understatement. After years of donating one dollar, twice a week, I struck it rich! I won two hundred fifty four million dollars in the national lottery. Like everyone else that I knew I had fantasized about what I'd do if I ever won.
Starting at the top, I'd bail out my brothers and sisters from their life of drudgery. There were others too, my work buddy named Joe that, by his actions, I was convinced that he would give me the shirt off of his back if I needed it. He loaned me his new Ford 4X4 to move my things into my house while it was under construction. I'll bet that I carried more and heavier weight and logged more 4 wheel drive time than he did the entire time that he owned that truck. I was sure that a new, full dress 4 X 4 was in his future among other things.
Then there was this girl that I worked with that was pretty beyond description. She had a boyfriend that I thought about buying off in favor of myself. Her name was Lisa; she was a petite five feet tall with black hair and brown almond eyes. I wanted her from the first time I met her. I trained her to do her job at the factory that we worked at and she picked up the routine amazingly fast. Soon she was the, "go to girl" on the production floor. I had trained her to perform many of the complicated operations required to assemble the widgets that we produced there. Too bad that management over looked her for a promotion. It was due to her Asian line leader's demeaning attitude towards women and the fact that she knew more about assembling widgets than he did. This was a mistake that I would try to rectify for her. I wanted to hire her as my personal assistant so she could spend her days as she did while I was teaching her the work duties that she performed.
With my winning of the lottery, I resigned from the widget factory and left word on the grapevine that I was looking for a Personal Assistant to lead my staff in the daily operations of my interests. Of course, I didn't have any daily operations yet, but I hoped that Lisa would be one of them.
I didn't have long to wait before Lisa called me and expressed her interest in applying for the position. I told her that there were a lot of responsibilities for my PA to deal with. They include extended travel and special projects that would consume much of her time. I also told her that a successful candidate would be highly compensated for their participation. She was intrigued with the job description and was eager to be evaluated for the position. I told her that she would undergo an extensive and invasive background and physical evaluation.
Lisa agreed to the application process and reported to my office located in Minneapolis to begin her job application. I hired a temp secretary named Sharon to administer the testing and using a newspaper ad, had an array of applicants to be processed with her. To set the tone I had each of the applicants sign a non-disclosure statement, and photographic release.
We conducted the battery of tests, slowly eliminating applicants throughout the course of the testing. As the tests progressed, Lisa could see that the pool of applicants would diminish as a direct result of the previous questionnaire, all of the questions were designed to be invasive. The questions elicited answers to questions of sexual experiences and preferences, extending to the extreme. So far, Lisa was still in the running for the position offered, even though she left a couple of the sexual relations questions unanswered. At the end of the first day, the remaining three applicants were photographed and rescheduled for a second interview. They were instructed to wear dresses or skirts and blouse, with stockings and heels. In addition, they were to bring a swimsuit, preferably a two piece and their makeup. It was stressed that the applicants should not buy any of the required clothes but rely on their existing wardrobe for their presentations. Wearing underwear in lieu of a swimsuit was acceptable. And makeup should be applied in the offices.
I had video of all of the applicants that passed the preliminary round of testing, and I was eager to see the results of the second round. The interview rooms were converted into dressing rooms, where the candidates would be measured for an evening gown and a cocktail dress. Facial photographs were taken without makeup. Later they would dress in the clothing that they brought with them for my evaluation. I had makeup artists and hair stylists on hand to assist the women in preparation for their personal presentations, which would take place throughout the afternoon.
The tailoring team consisted of a male tailor and his female assistant. Together they measured every aspect of the candidate's figure. Her foundation wear sizes were confirmed and compared to the clothing that the candidates had brought with them. If there were any discrepancies, the team would take note and procure replacement garments. This part of the interview took an extensive amount of time and the candidates were nude for extended periods.
After completing the sizing portion of the evaluation the tailoring team departed to prepare the clothing that was required for the evening wear.
The hair stylists arrived and applied their talent to the three women candidates, styling their hair in a late fashion to accent their facial shape characteristics. The candidates were introduced to a spa treatment with facials, manicures, pedicures, ending in a massage.
The women were made up and dressed in the clothes that they brought with them. Individually, they were escorted into my office for an interview. I asked them to answer the questions that they left unanswered on their questionnaires. Lisa was embarrassed by the questions asked about kinky sex and bestiality. They were essay questions and required thought out answers, making the question itself increasingly complicated. I enjoyed watching her squirm as she chose her words carefully to formulate her answers. Sitting in the chair with her skirt edging up her smooth thighs, had me distracted more than her obvious embarrassment at the subject at hand. I knew that her boyfriend would not let her wear anything that highlighted her legs, and I was fascinated with the fact that she was wearing a dress. She had some of the best looking legs that I have ever seen, and feminine legs were special eye candy to me, and I noticed a lot of them. I watched as she walked around the office, modeling her dress, and then directed her to sit on a low sofa and cross her legs for my pleasure. She was a keeper in my estimation and it seemed that she really wanted this position. The question that I had was how much do you really want it? As the interview came to an end, I asked Lisa to raise her dress, and show me her panties. She looked at me in surprise and contemplated my request for a minute before she reluctantly raised the hem of her dress above her panties for my evaluation. She looked away from me in embarrassment as she exposed her smooth thighs to my inquiring eyes. It was all good in my opinion, I always thought that her legs would be outstanding and I wasn't disappointed. Lisa was whisked back to her dressing where she was instructed to put on her bikini and prepare for her next showing.
Lisa did not have a bikini or other swimwear and was preparing to wear her underwear for her next evaluation, when her makeup artist stepped into her dressing room to give her a final once over before her presentation. She stopped Lisa and told her to disrobe so that she could apply a bikini trim and a tanning spray all over her body. Lisa was amazed at the attention to detail that she was experiencing. This was some pampering that she had never experienced. After the spray treatment was completed, the artist dressed her in a new pink/black Wicked Weasel, Microminimus bikini that fit her perfectly. She instructed Lisa to wear a pair of black heels that were also provided. Lisa looked at herself in the mirror, she was a true beauty and she was impressed as well as proud of her looks for this important interview. But she was almost naked! The secretary entered her dressing room to escort Lisa to her showing. As she entered, she handed Lisa a sheer black Singlet dress to wear over the bikini. Relieved, Lisa donned the translucent black dress and was led to my office. As they were underway, the secretary instructed Lisa to remove the dress as soon as she arrived at the center of the office and take up a pose. The candidates had been coached on the poses that could be used for their showing and persuaded to pick and practice a couple of them in their spare time between showings.
Lisa performed as instructed when she walked into my office. She walked around and then presented herself right in front of me for my up close evaluation of her nearly nude body. I felt her to determine the muscle tone and skin texture of her gorgeous body. (Right!) I could see her chest rising as I was exciting her with my hands, and I had only just begun to feel her up. As I held her sidewise to my sitting position, with one hand on her bare ass and the other hand massaging her stomach I asked her to remove her triangle top. Lisa seemed to be in a trance as I felt her. She removed her top and my hand moved up and cupped her stout breast. Lisa stood in her spot as I freely kneaded her newly exposed tit and roamed my hand over her smooth body. I asked her questions as I maneuvered her to sit on my lap as I continued to fondle her nearly nude body. I couldn't get enough of her.
Before the candidates left for the afternoon, they were all photographed in all of the outfits that they modeled and instructed to report back to the office for their physical. One of the dressing rooms was converted into a doctor's examining room. It was complete with an examination table and a portable x-ray machine.
The next morning the three candidates were assembled in the waiting room, waiting for their physicals. The nurse escorted each of the young women into the examining room in turn for their complete physical evaluation. Upon completion, the candidates were instructed to return to the office and prepare for their evening evaluation.
The women, Janet, Cherpree and Lisa were scheduled to attend at least two social functions tomorrow evening. The women, would each have dates and attend a formal function, then switch partners and then change clothes to attend a cocktail party, where they would again change escorts to the third gentlemen, I was the principle escort and the simulation was addressed around the candidate in the three different scenarios. The first encounter was with the candidate approaching a client and occupying his time while waiting for the boss to arrive and take over the hospitality. Later, after the exchange, the assistant to be would be filling in for her recently departed boss to occupy the client for the evening. The third scenario was to evaluate the ability of the candidate to cover for her boss; the candidate would be evaluated by her escorts as they tried to take advantage of the woman left to her own resources. It promised to be a unique experience.
I arraigned to escort Lisa on her second encounter with the option of terminating her participation in the exercise if she succumbed to my advances. I interceded in her evening at the first intermission of the theatric presentation we all were attending. We talked briefly about the evaluation process and how it was affecting her personal life. Lisa said that she had no problems with her involvement and still wanted to be selected as my PA. I explained to her that there would be a two week training retreat for the selected candidate. I wondered if she would be available for such an adventure. I could see that she was getting more intrigued as I spoke, but I would not divulge the location of the retreat that I had planned for us.
We watched the performance through its conclusion, and departed via limousine to The Hyatt Regency Hotel, where there was a VIP Suite reserved in my name. Lisa was stunned at the elegance as we promenaded to the elevator for our assent to the top floor. I led her to the suite where we were met by a concierge who opened the door for us. He handed me the key card as I walked by and closed the door as we strolled into the massive main room. I directed Lisa into the bedroom and had her prepare for our entrance into the hotel restaurant for our evening meal. She was still awe struck as she proceeded into the bedroom to find a house maiden to assist her in disrobing, and escorting her into the luxurious bath tub, her cocktail dress, complete with her stockings and under garments, laid out on the King Size Grand Bed for her to slip into, after the bath.
Myself, I retired to the second bedroom and prepared for my shower as well. I changed from my suit into a white dinner jacket with navy blue trousers with a powder blue tie and returned to the main room to sit and await my future PA.
Lisa was bathed by the young House Maiden and dried with a fluffy towel before being dressed by her maid, who paid attention to every detail of the young woman's body as she presented and smoothed every article of clothing onto Lisa's exquisite figure. As Lisa gazed upon herself in the full length mirror, she could plainly see the visual change that this evening of pampering had instilled upon her. She was simply gorgeous!
As she entered the main room, I stood and embraced the young woman and kissed her like a lover would, with a promise of more to come. We departed the suite and shortly arrived at the dining room.
We were immediately escorted to their table and seated. The wine Steward appeared and offered me the wine list for my selection. I ordered Champaign for the both of us and waited for the menu to arrive. Soon the waiter materialized and handed the menus to us. I ordered a steak for me and marinated chicken on a rice pilaf for Lisa. Lisa had no idea what I ordered for her so she had to wait to see what would transpire. She was pleasantly surprised to see that I had ordered for her as I appeared to know what would fit her palate the best. As we were eating a band assembled and began to play soft rock tunes for the diners.
When we finished eating we were joined by the other two couples who were similarly dressed in their cocktail dresses, the male escorts in their powder blue dinner jackets and white ties.
I led the festivities by escorting Lisa out onto the dance floor to engage in a waltz. Lisa had not been schooled in ballroom dances and it showed, as we regressed into a slow two step and pulled Lisa close to me. We moved around the dance floor until the music glided into a faster tempo allowing us to leave the floor. The other two couples moved onto the dance floor and grooved to the thumping beat of "We Will Rock You", as we sat in our chairs at the table. I beckoned Lisa over next to me and he whispered in her ear that she would have to undergo three weeks at the retreat to improve her dancing skills. I placed one arm around her shoulder and slid my hand up her smooth thigh, and whispered that she had the job if she wanted it. I told her to report to my suite in the morning to discuss the benefit package. Lisa knew that she would be nudging me in the morning to awaken me for that conversation.
We partied among ourselves the rest of the night, and I took advantage of this situation by spending time with the other two candidates, where I felt them up as we sat or danced together. All of the women receptive to all of my advances and I started reflecting on other positions in this organization where they would fit in. I needed a driver and could use a house keeper to round out my core staff. I decided that he would offer positions to each of the women to keep them around and available. I would take them on a retreat to break them in as well.
As the evening ended, I escorted Lisa to the elevator, where we ascended to the suite prepared for us on the top floor. As before, a concierge awaited us at the entrance to the suite with a key card, and opened the door for us. As we entered the suite I told the concierge that we would not require the services of the House Maiden until tomorrow morning, at which time I would send for her. The concierge held the door for the House Maiden as she departed and then closed and locked the entrance to the suite.
I led the astounded Lisa into the bedroom and began making out with her as I removed her clothing. Stopping at her underwear, I caressed her skin, taking care to fondle and kiss every exposed square inch of her female form. Lisa was on fire, she had never been loved like this and the previously feeble attempts of her soon to be ex-boyfriend equated to groping of her sensitive body. And to think that I haven't touched her most sensitive areas yet! I could feel Lisa's breath rasping as her excitement grew to a higher level each minute of manipulation of her sexy body. I removed her bra to revisit Lisa's generous tits, this time using my mouth as well as my agile fingers to stimulate her glorious breast meat. Lisa exploded in a massive orgasm as I continued to kindle the flames within her writhing body. As I trailed kisses down across her smooth stomach, I removed her panties as I kissed her just above her soaking mound. Lisa's fingers turned white as she grasped the bedding and held on in preparation for the ride of her life. I slapped Lisa's clit with my tongue as I descended onto Lisa's dripping slit, all the time I was lapping the abundant juices that the young beauty was expelling from her tiny pussy. My hands were stroking up and down Lisa's smooth thighs as I ate her fastidiously. Provoking yet another climax from the overstimulated beauty, I gently slid my finger into her drenched canal and searched for her elusive "G spot". Upon finding the nerve bundle, I increased my fingering tempo as I bit down gently on her engorged clitoris. Lisa screamed as she trembled and bucked herself into oblivion at my adept mastery of her body. She lay on the bed spent as I moved into position, between her trembling thighs. Lisa was continually moaning as she lay still, recovering from the most intensive orgasms that she had ever experienced.
I was not one to wait as I surveyed the young beauty, slowly recuperating from my sexual onslaught on her inexperienced body. I lined up my cock and aimed it directly at the young woman's center and gently impressed it into her gushing pussy canal. Lisa squirmed as I impaled her young body on my pole, driving deeper and deeper until our pubic hair meshed and my massive meat kissed the opening of her cervix. I lay in Lisa's lap and gently kissed her lips as I afforded her the time for her to acclimate to my immense displacement of her womanly canal. Lisa swiveled her hips in an attempt to fully seat my member into her frothing quim. As Lisa regained her composure, I began my drive to split the beauty by impressing his protrusion into the frantic woman. As my speed increased, Lisa bucked into me thrust for thrust until she blasted the room with another exemplary scream of pleasure as the result of another climax. I dived into Lisa with a final stroke and emptied my pent up sperm laden balls into Lisa's receptive womb.
We slowly untangled from each other the next morning and hand in hand we entered the shower to give each other a thorough scrubbing and rubdown. I once again took Lisa, this time in the shower where I lifted her off of her feet and pounded her little pussy. Lisa hung onto my neck while wrapping her legs around my hips while she kissed me profusely. Soon I could stand no more and properly greased Lisa's steamy pussy again.
We both adjourned into the main room and took up seating on the sofa, Lisa sat on my lap as I fondled her sensitive tits, and stole kisses from her periodically. This was serious business but I was determined to consume Lisa with my newfound wealth and hyper libido. I knew that my offerings would blow her away; she had no concept of the wealth that I possessed and the limits of my pocketbook. I started my offering as I slid my hand into Lisa's steaming pussy, and pressing my finger gently over her swollen clit.
Seventy five thousand dollars per year, salary, flat rate, on call twenty four hours per day, seven days per week. Luxury class car of her choice, fully expenses paid. This includes gas, oil, all maintenance, personal driver on call twenty four/ seven, and a clothing allowance, to be determined. Lisa was getting increasingly excited as I tantalized her with my tongue in her ear, describing her benefits with my fingers in her pussy. After this first round, Lisa was a yes girl as my description of her new life astounded her beyond her wildest imagination.