Lili; Starting Over Again

I am twenty-eight and have managed to achieve most of my life’s goals, the ones that I had visualized when I started out after college. The goals were not to own some adult clubs, but to be reasonably secure in my finances and have something to engage in to keep my mind occupied.

I own fifteen adult clubs, three that I had started myself and the others I had bought in a deal a little over a year ago. The ones that I had started myself were just run down bars, the rent was cheap and I saw an opportunity. I got them cleaned up, revamped the interior and opened for business. I managed to make rent every month, but needed something distinctive to make the bars stand out. I hired some females to serve the drinks, my first cocktail waitresses. Well from that moment on, things improved greatly. Within a month I was making a tidy profit, channeling some of that profit back into the clubs. The bar name no longer appropriate for the resulting business. I got the ladies some costumes to wear, brief but covering all the essential things that needed to be covered. Cheryl was one of my first females to be hired, drop dead gorgeous and very enthusiastic in her work ethic. I put a few more ideas in place fashioning the clubs into what I saw as the ultimate business.

I patterned them after the old Playboy clubs, only much naughtier. We served a varied menu of drinks plus some appetizers prepared at the club. The décor was fancy, opulent furniture in both the bar and lounge areas. I bought only the better wines and alcohol, the bartenders capable of mixing any drink you could name. We also offered varied coffees, some exotic teas plus some imported beers.

The centerpiece of the clubs was, of course, the waitresses whose name morphed into cocktail waitresses. The uniforms were scant, although the appropriate parts of the anatomy were covered to assure our clubs were able to get their licenses. I always thought a female looked sexier with a few well placed items of clothing then when totally naked. So the costumes were tailored to each girl featuring their best assets to the max.

In a few of the clubs locations, I had to hire attorneys to make sure we were allowed to operate. The local governments in these towns were determined that we would not be allowed to open the club, passing many temporary ordinances and rules to try and thwart us. In one particular town, we were raided seven times as they tried to close us down. They never found anything illegal but certainly tried their best to do so. I was persistent in my endeavors, the publicity of the raids very good for business. A year later, the town relented some, we were still closely watched, but the raids stopped. To this day the chief of police of that town is a frequent visitor, I am sure it is not to check us out, but to visit with some of our cocktail waitresses, one in particular catching his eye whenever in the club. On the week she is off, he comes in checks us out then leaves after hearing she is off that week.

The girls do wear clothes, pasties and G-strings are never seen in the club. The clothes however would make Frederick’s look like a clothing store for young school girls. We had a staff of five ladies that designed and made the costumes. Each girl at the club wore a different costume most every day, thirteen different costumes to chose from in their wardrobe. The costumes were designed to show off their attributes to the best advantage. The girls worked seven days a week for two weeks then received a week of off time. Another one of my ideas, I figured they would like the whole week off, even though they had to work two weeks straight to get it. Their hours were from eight in the evening until three in the morning. They received a salary, plus their tips, none of the girls seemingly wanting for money. I made sure their salary reflected an amount suitable for their position.

I toured the clubs regularly, making sure they were doing what I wanted. I really didn’t have much to do, the managers of the clubs did what they were supposed to, the girls and customer relations the most pressing matters usually. When I first started, I went with male managers, thinking they could handle the girls and any customer problems best. After a few months, I promoted one of the girls that had been with me the longest to manager and what a difference it made. A lot of the customer problems that we were having never materialized. Instead of waiting for the problem to develop, she watched for signs of a problem and stepped in right away to head it off. The girls reacted better with her, since she was aware of what they faced each night.

Three months later, the last of my male managers disappeared. I did keep one well-built male bartender/bouncer at all times, someone to handle a problem drinker and customers trying to enter the club already inebriated. The other bartenders were all female although their costumes were not as risque as the cocktail waitresses. All of the rest of the floor help were female, including the girls to clear the tables after eating. Quickly those girls earned the name bus-ty girls, still dressed provocatively but tamer. The costumes of these girls always accenting the breasts. A new girl would always be started as a bus-ty girl until she saw what was going on. Then if warranted she was promoted to a cocktail waitress.

The location outside of Orlando was always my last stop, Cheryl the manager there, the first employee I ever hired. There was nothing romantic between the two of us, I just was always at ease around her, both of us able to freely converse about almost anything. Maybe because she was the first one I hired, but I always thought she was the perfect female for the clubs. She stood five foot ten, a little over six feet in her heels. A very generous figure, firm and toned. Like most of the girls she worked out in a gym, keeping everything tight and attractive, a small price to pay for their continued employment and generous income, at least in my opinion.

I had got to the club late, traffic was worse than ever some concert or something in town. At two in the morning, the club was still packed. I made my way to the bar, settled in and watched what was going on. Cheryl waved at me, but something else held most of her attention. I watched, then smiled, one of our customers had rapidly approached the too much to drink mark and was man-handling one of the waitresses. Cheryl had a word with the waitress, then retreated to her observation spot.

The waitress was delivering some snacks that they ordered when she was groped again. She leaned close to the inebriated customer and whispered in the guy’s ear. The guy suddenly perked up quickly scanning the crowd, he spotted me and immediately straightened his posture. A few minutes later he asked for his check, paid quickly making a bee line for the door. I chuckled, Cheryl had the most success with this particular solution to the drunk customer. The waitress whispering to the guy that her boyfriend was sitting at the bar, and was not happy sharing his girl with others. I watched Cheryl make one more round of the club, then strode over to the bar grabbing my hand and leading me back to her office.

As soon as we were in her office, I was hugged, held for quite some time. We sat on her couch, right next to each other. That was just the way Cheryl was, maybe not romantically involved but definitely wanting to share the same space with you intimately. Other than a hug from time to time she was all business, even more so than myself. We talked about the club some, her sales and profits on the increase again, after a brief leveling off, a couple of months ago. She had hired three more girls, anticipating an increase in business. Woman’s intuition or something else, she was seldom wrong in her hunches, so I never questioned her about her actions.

Recently in our conversations, we had begun to talk about what both of us would do after the clubs. She had told me that ten years is about it for a female to look her best, then age and time starts to make changes to the figure. She figures another three years and she needs to find something else to do. I tried to convince her she could stay at the clubs, even moving up in the business. For me the lure of developing something new and making it profitable was gone now, I still had feelings for the business, but not as strong as when I started. Cheryl could easily take over the running of the clubs leaving me to find something else to occupy my time and interest.

The problem was, and has always been, what that something was? I graduated college, got my bachelor’s degree but never excelled at anything. At times I think I was passed so that they would not have to face me in class again. I had sort of a bad reputation, asking way too many questions and arguing almost any view point that was presented. I am sure that most of my professors were very glad to see me walk across the stage to receive my degree, a pain in their ass no longer.

I never took any interest in sports, the effort that needed to be put forth was not worth the energy required to do so. I never got into the bad habit of snacking on things during the day, breakfast and something light for dinner was my normal daily menu. I stayed busy, so the idle times to maybe seek something to eat never materialized. For my five foot nine inch height, I weighed in at one hundred and thirty-five pounds. My features were not pronounced, nose and ears proportionate to my face and not sticking out obscenely. I did however have hair down to my shoulder blades, a dark ash blonde in color. Since there never has been any participation in sports, no muscle development, so none of my limbs were other than minimal in size and thickness. Walking around the block would leave me winded, if I even made it around the block in the first place. Well lets be truthful, I would never attempt to walk around the block, any physical exertion other than picking up a drink glass or feeding my face just nor indulged in.

Cheryl and I have talked about the future before, lots of possibilities explored but nothing decided on. Tonight was another of those times, four hours of conversation about possible futures for both of us but nothing even remotely decided on. I gave her a hug as we parted, the club now closed, the sun coming up in another hour or two. Her girls had handled closing the club as they normally do, making sure everything was set up for tomorrow’s business. Then they quietly headed home to get some well-deserved rest. The club was now empty, Cheryl and I deciding to do the same. That is the nature of the business, days are for sleeping nights are for business and work.

I made it home, a townhouse that I bought several years ago. In fact, it was only three blocks from Cheryl’s club. Nothing exciting happened in the next week, then an unusual request for Cheryl for some time off. No problem, she has taken very little time for herself in the years we have been working together. Her assistant more than capable of running the place. Then my attorney called asking if I could come in to talk to her on Friday. Judy was another one like Cheryl, in fact, I put her on retainer shortly after hiring Cheryl those many years ago. When we were having difficulty with a few towns that we opened clubs in she ran the show, keeping the politicians toeing the line. She was meticulous in her work saving my butt on more than a few occasions as I put together my little group of businesses. I tried to pry out of her the reason for the meeting, but she just told me to wait until Friday. In some things she and Cheryl were almost identical, one of those being I will tell you what is going on when I feel like it and not a moment sooner.

When I bought the other clubs, her checking into things and handling all the paperwork was worth a fortune to me. I walked in signed the papers and wrote out a check and the deal was finished. Twelve clubs and eight hundred thousand dollars were exchanged in the deal. The clubs were in need of repair and renovation, the previous owner had made no improvements for over two years. The price was right, so I entered into the deal. I was nervous about spending that amount of money, but somehow I found the confidence to close the deal.

Over the next few weeks the clubs were renovated, repairs made as necessary and new décor added throughout. Cheryl handled briefing the managers we had decided to use for the new clubs. We kept three of the existing managers, all female incidentally, then moved some of our existing assistant managers to handle the rest of the clubs. Cheryl and I made the rounds giving support when needed, but we had very little difficulty. We had kept an advertising ban in effect until we had the clubs functioning properly, then ran a few ads. Those probably were not necessary as the business was already picking up at the new clubs. I think most of it was the better decor, the clubs looked more inviting now, not like an old rundown bar. Of course, the girls and their costumes contributed greatly, much better sights to look at as they were enjoying their drinks.

Cheryl did come back on Wednesday, a smile on her face, but no reasons for that smile. Friday morning I slept late, forgetting all about the meeting. When I did manage to remember and get ready I ended up twenty minutes late. Of course Judy gave me hell for it, reminding me that time is money, but since I was paying her, she would let it go this time, her obvious smirk more than visible.

She took out this huge folder from her desk drawer, laid it on top of her desk and then stared at me. I chuckled, then just told her to get on with it, whatever it was. Her next words caught me by surprise. “I have an offer here to buy all of your clubs presented to me yesterday. The group making the offer I have checked out thoroughly, they have more than enough funds to handle the purchase and run the clubs for a year never needing to tap into any additional funds. The offer is quite substantial, twenty percent over an appraisal of your business that was done just a month ago.”

“There are several stipulations in the deal that are a little unusual, not normally in any agreements to purchase an existing business. One of the stipulations is that you have to stay on in a position of their choice for five years. The exact wording is that all of the purchase price is to be put into a trust in your name. If you fulfill their requirements to work for them those funds will be released to you after the five years have passed. The guaranteed interest on these trust funds is quite high, fifteen percent. They want to be sure they have your help guaranteed for the full five years. If you fail to live up to their requirements, there will be no interest paid and the trust funds will remain frozen until the five years are up.”

I just looked at her but she continued, “They are very adamant on this, the whole deal revolves solely on this one condition. I have suggested some other possible wording of the clause, but they have turned down any re-wording of the clause. I have spoken to the principles in this they seem capable and quite gung ho. They have prior experience in the adult club business, so they are not new to the business.”

“Now for the good part, recently your business was appraised for thirteen and a half million dollars by three separate appraisers. They are offering sixteen million dollars subject to the stipulations I have just stated. That is quite a premium profit for what you have invested in the clubs, I personally would suggest that you consider this offer quite favorably. Offers like this do not just pop up, at your wishing.

If you are agreeable, they will meet you on Monday in this office with a cashier’s check and the agreements they want you to fulfill. We can conclude the purchase that morning. Your bank is alright with them for the trust fund, so that should not be a problem. You will receive compensation for your work with them at the usual rate for that position during your employ. Let me know later today so that I can finalize the Monday meeting, otherwise, I will have to arrange another meeting when all the parties will be available.”

I didn’t even ask any questions of Judy, all of this was just too much to get a handle on. I did tell her I would call her later if I decided to sell. I wandered out of her office, got in my car and drove back home. I set at my computer in my little office and tried to figure out what to do. I had kept a spreadsheet of what I had invested over the years, the leases on the properties, the décor, renovations to the clubs and the deal that resulted in me getting twelve more clubs a year ago. I looked at the total and I had only invested a little over eight million so far. With an offer of sixteen million that is quite a good return on my investment. That does not take into consideration the money I have withdrawn so far in wages for myself over the years.

It sounded too good to be true, but I knew Judy had checked the proposal to the nth degree, just her normal habit. I eventually decided to take the offer and called Judy to let her know of my decision. The meeting was set up for Monday morning at eight A.M. I questioned the early start time, since I have never been up that early in the last seven years. Judy said it was requested by the buyers. They also requested you to be available later that same day to start your tenure with them. I gave her a quizzical look, but she just smirked, telling me to be sure and call her when I decide what I am going to do. That was it, discussion over, typical of Judy but frustrating, nonetheless.

I did have many thoughts on the deal and the unusual request of me. Since I had nothing to do otherwise, I had no trouble working for them for five years. I imagined it would be in the same capacity as now. Still something just didn’t seem quite right. I ended up with a headache so with my head pounding all thoughts quickly ceased on the subject.

The weekend passed quickly, I visited Cheryl once on Saturday night although we didn’t talk much. For some reason the club was packed, even people standing behind customers at the bar waiting to get their drinks. All of the tables were full, both dining room and the lounge. When someone left, the ones at the bar were seated in the empty table. It was unreal, I briefly wondered if I was doing the right thing about selling the business, but it was only a passing thought. The offer was just too lucrative to pass up.

I was awake most of Sunday night, couldn’t get comfortable, then when I found a spot, my mind went bonkers with different scenarios. I wondered who was buying the club. Sixteen million is some pretty hefty change to come up with, and in the form of a cashier’s check even more incredible. Then to be told the group had some experience in managing adult clubs, I was not aware of any other group in the area that had some adult clubs, maybe they are from the west coast. So many unknowns, but still a wonderful deal for me, I think.

So at a few minutes till eight, it was a very tired and poorly put together me that made an appearance at my attorney’s office. I was shown into their conference room, the entire room filled with beautiful females. Then on a second look, they were all my employees, even some of the other managers from my clubs out of town. I focused on the table where Judy sat, a huge smile plastered on her face. Right next to her was Cheryl in a drop dead gorgeous business suit that seemed molded to her body. More than a little cleavage was visible, my eyes focusing on that particular point of interest.

Some of the other gals led me to the table and I was helped into a seat right next to Cheryl. In front of me on the table was a cashier’s check made out to me. Right above that was the purchase agreement, several copies waiting to be signed. It took me a while to regain some control of my body, a more normal breathing the first thing I sorely needed. My heart rate seemed to stabilize some, at least the loud sound of my heart beating could no longer be heard in my head.

Judy got everybody’s attention and started with the documents. The first was the setup of the trust fund, once that was signed she had me endorse the back of the check and she sent her secretary to the bank to make the deposit. I was only about half there, way too many thoughts trying to get a foothold in my mind and none of them achieving that feat. I hadn’t drank any coffee this morning yet, that also a major cause for my sluggishness.

Then she moved to the purchase agreement, once more explaining what was involved. The part of me working for them for five years in the job of their choice was especially stressed. When the agreements were pushed in front of me I quickly signed, I doubted I could keep it together much longer. I felt like I was awash in a large body of water, not knowing where I was or what is happening. I remembered the purchase offer, the money and that I would be staying on with the new owners, but not much else. I was given copies of everything and everybody filed out except for Cheryl. All the girls gave me hugs as they left, they seemed especially happy at the deal and what was to come. Cheryl remained seated, eventually moving her hand to carefully grasp my arm and pull it to her.

“You need to listen to me. The girls and I have been putting money aside for our future. Some of it had been invested in stocks to hopefully give us a little more to work with when we retire. We got lucky last week and four of our stocks split five to one. That allowed us to buy you out. I have remembered our conversations over the last few months about what you might do when you suddenly have to face your future. Well that time is now, since you have no idea of what you want to do, it has been decided for you. We have all discussed your future, thus the clauses that you will work for us in the job of our choice.”

She let go of my arm and said, “That starts tomorrow after we get your body too match what you will be doing.” She carefully looked my way to see if I had suddenly realized my fate. A smile then appeared on her face, shaking her head at me I was helped up and led from the room. As we made it out to her car, I was seated in her passenger seat and my seat belt fastened. On the trip to wherever, I was just there, maybe physically but definitely not mentally. My mind was trying to put two and two together, but for some reason ten kept coming up, then when I came up with fourteen I sighed and my mind shut down.

She drove us to the other side of the town and to the side entrance of a large building. Since she came in from the backside I had no idea what was housed in the building. We were in a partially protected area, shielded from the rest of the area with a few hedges and small outbuildings. I was released from the seat belt, then stood up right next to the car. She quickly undid my belt buckle and as my pants slid down my legs, she lifted my polo shirt over my head. As I tried to grab my pants my boxers soon joined them, then she pushed me forward, forcing me to step out of my pants and boxers or trip on my own clothes. My loafers were caught in the mess around my feet and I lost them too.

Now entering the door next to the car, I was totally naked except for a pair of socks. She did take the time to gather some of my clothes and place them in the dumpster, giggling as she did so. I watched her do it, but any significance of why escaped me.

Along a short hall and then into a room where several more ladies awaited me. I was helped up onto a table and then laid back with my head and chest facing up. Quickly my legs were secured and then Cheryl grabbed my hands and handed them to the other two ladies. Those too were secured and then the ladies left for a minute to get things ready. I laid there dazed, no rational thoughts appearing, just breathing and staring at the ceiling as Cheryl tried to get through to me.

“Well I see that your mind has not caught up with your fate. You agreed to work for us in a job of our choice for the five years, that job is as a cocktail waitress for the duration of the agreement. You have a choice now to make, it can be done with you as a male in a special costume we have designed for you or you can get transformed to a female to do your job. No pressure here, but I think the better choice is to do it as a female. In your special costume, that male organ of yours will kind of stand out, maybe a little too much. The fact that you will be serving your friends and business associates, I think the female look might be preferred. A little less humiliation that way.”

I just stared at her, my mouth about as wide as the bones in my jaw would allow. I couldn’t even form a question as to why this was being done to me. Another one of her huge smiles settled on her face as she took my hand in the restraint at the side of the table and squeezed.

“Let’s face it you have lost your drive and push in life. There is no longer a challenge for you in any part of your life. Well we are going to fix that and very soon. You will need to learn how to be a female, how to dress, do hair and makeup, and interact with society as a member of the female gender. If you apply yourself, I just might promote you to the manager of the Orlando club someday, hell if you do real well I might let you run the whole shebang.” She was giggling as those words left her mouth.

“Every day you will face a challenge, to become Lili and work for a living. I don’t think you have realized that you have no income to live on for five years, so the job as a waitress is necessary for you to eat and pay your bills. So much money but not a dime to spend. All of this was done to you on purpose to force you to immerse yourself in life again, although it is a part of life you have not visited before. At first it may seem cruel, but after a few days, I think you will find it exciting and exhilarating.

“I need to know your decision, the ladies are ready to transform you, we just need to know which way you want to go. The paperwork has already been signed by you, so give us the word and we can get you fixed up.” She did stress the fixed up wording. I swallowed hard several times, finally squeaking out an answer to Cheryl. “A female please, I can’t see me as a male waitress for five years. Just the thought of that makes my stomach turn.”

Just as quick as she heard my answer, the ladies were asked back in and I was kissed on the forehead and Cheryl left, smiling and giggling as she exited the room. My feet already in stirrups were spread apart as far as the muscles would allow. The portion of the table directly below my genitals was lowered and my male apparatus hung there swaying in the breeze. As I was trying to come to terms with my proposed sex change, a cream was rubbed onto my body covering all areas below my eyebrows. It remained on my skin for about thirty minutes then a towel was used to remove it along with all of my body hair.

Next a cool spray down below and suddenly I lost all feeling there. I tried to turn and see what had happened to my favorite companion but I couldn’t see anything. I felt a presence between my legs, but couldn’t see who or what they were doing. I groaned trying to get someone’s attention, but everybody ignored me. I finally relaxed, I couldn’t get loose and I was helpless to do anything to stop the process. My days as a member of the male sex seem abruptly over.

When I was finally able to see between my legs, there was no sign whatsoever of me ever being a member of the male sex. A cute slit, with two puffy lips framing it was all there was to be seen. I shuddered, in a few minutes my entire male life had disappeared. I was secured to the table but my body was twitching some, like the missing organ could still be felt, one more look to make sure that it indeed was missing.

My cute and sexy slit was quite prominent, nothing left to camouflage the area. Just soft barren skin that looked so soft and desirable. My chest hair in particular took years to amount to anything, now it was totally gone. I kept looking at my groin every time I had a chance to see it, hoping somehow that the missing part would reappear. Now the cool air over my hair free skin was messing with my mind. Goose pimples were popping up everywhere.

I was so concerned about the changes that I forgot about how this drastic change would affect my life. I pictured myself in one the girl’s scant outfits, in towering heels and waiting on customers. It finally sunk in, my new life will not be anything like my old life. With that thought bouncing around in my mind, all of the implications started to materialize and I zoned out. I don’t think I fainted, I just lost track of what was happening to me, at least mentally. I do remember brief episodes, one when a pump started pulling excess tissue into forms glued to my chest. I didn’t spend any time trying to figure that one out.

The thing that brought me back to reality was when a cloth was ripped from my eyebrow, the warm feeling first then the pain shortly thereafter. Looking in the mirror above me I could not find any eyebrow left, another causality in my transformation. Right after that episode, some rational thoughts did appear, and I got my first look at the enormous breasts that now are residing on my formerly flat chest. The forms were still there, two hoses leading from the cups to the pump somewhere, the suction of it still trying to pull more flesh into the already jam packed cups.

Finally the suction stopped, the hoses were released from the cups and I was released from the table. Just the act of sitting all the way up was harder than I imagined. The considerable weight added to my chest was not helping matters, as I managed to get to a sitting position the protrusions swayed a little, even though they were still in the forms. Talk about a weird feeling, my mind was now focused on my new breasts, temporarily forgetting that I had lost my penis in the process. I just sat there looking down at my chest, then shaking my body some so that one of my breasts moved slightly so that I could peek at my new slit. As my breast swayed a little against my chest, it felt warm, they indeed were my flesh and attached firmly to my body.

It was several minutes later when one of the technicians came to get me. She explained that the forms stayed on, dissolving after a few days. The breasts are indeed mine, there for the duration or until I desired to remove them. The nipple is very responsive, can get hard from a touch or visual stimulation. I can feel touch to other parts of my breasts, and when not in costume a bra needs to be worn at all times to prevent sagging over the years. That word years seemed so dramatic when she used it.

My lower equipment is also touch sensitive, can be used for sex if I want. It needs to be douched regularly, especially after sex. You can handle most size male organs except for the well-endowed specimens. A little lubrication is usually beneficial, but not entirely necessary. I will not suffer a period, but a tampon will help after sex to keep the fluid from dripping down my legs. Oh gawd, a male can penetrate me for sex, that can’t be right. Surely I won’t be expected to have sex with males, Ewwwww.

Her last sentence was not what I wanted to hear, neither the sex nor using a tampon to keep from dripping was anything I ever wanted to experience. I know my face showed the embarrassment, bright red from my forehead to my neck. I imagine there was also more blushing from other body areas, but I forced myself not to look.

My hair was shampooed, conditioned and a female style cut in to my shoulder length locks. Then she coated the hair in a foul smelling liquid, I presume my hair will no longer be ash blonde, from the light color of the liquid, I would guess that I would now be a very light shade of blonde. After the bleach was washed out and a toner added then washed out, my hair was set in curlers. A dryer was placed over my head and a steady warm heat poured over my head until my hair was dry.

I could still not come to terms with what the girls had done to me. I was rich, but unless I worked for them I would not have any money for five years. I am sure most of that is Cheryl’s doing, maybe with a little help from Judy. I remember the smile on Judy’s face in the meeting, she was quite pleased with my fate, the many looks exchanged with Cheryl probably gloating at the coo they had pulled off. I was totally screwed in the deal, no choice left but to do as they wanted, any other option either not available or a real bad choice. Since I didn’t own the clubs anymore I had no way to get anything changed, I had signed the papers, now I essentially belonged to Cheryl and the new owners. With a female body, chances of getting employment anywhere else is scant, I even doubt if any of my old identification is valid anymore.

Once my hair had been dealt with, a corset was wrapped around my body and I was cinched tighter than I thought possible. I was gasping for breath as they tightened away, the laces secured behind me where I could not reach them. Believe me I tried. I was helped into a short robe, then Cheryl showed up grabbing my hand and leading me away. Out the same door I entered and into her car. I was driven to my townhouse, a smile flickering across my face knowing that my male clothes, and something to cut the laces on the corset would be found inside. Once she unlocked the door, I looked around, a large frown settling on my face. This is no longer a townhouse of a male, but of some girly gurl female. Frilly drapes, pastel colors on the wall, and a shaggy white carpet, all screaming female. Surely I had not been at the salon that long for all of this to be changed.

Then when I entered my bedroom I sat hard on the edge of the canopy bed, my closet door was open part way and all I saw was the costumes for my new occupation. The floor lined with heels in most any color imaginable. Not just heels but five and six inch high heels, with only tiny straps to hold them on my feet. A new vanity was next to the bed, covered with cosmetics with a lighted mirror at the back. Cheryl went into the closet and retrieved one of the costumes, laid in on the bed next to me, and told me to get dressed. You start work in an hour. I glanced at the brief costume, it at least would cover my corset some, I imagined I would start as a bus-ty girl like all the others. Looking at my chest I seemed to have the primary requirement handled easily. The six inch heels did evoke a tear from me, Not only would I have to learn to walk in heels but at the higher heel height.

First some sheer stockings that attached to the garter tabs hanging from the corset. The tension of the stockings and the pull of the tabs on the corset sent more unwelcome feelings through my body. Gawd, how do females cope with everything seeming to keep them aroused and on edge all the time?

I did manage to get the costume on, a body stocking that barely covered my erogenous zones, breasts spewing over the top of the corset, the part between my legs conforming tightly to my slit, making it seem even more noticeable. There was a frilly little transparent skirt around the bottom of the body stocking letting the top of the stockings and the garter tabs of the corset show right through. Then Cheryl helped zip the back of the stocking, now it fitting even more tightly than before. I slipped into the heels, struggled to get the straps fastened then had to almost run to keep up with Cheryl as we headed back to her car. I was far from graceful, teetering in the heels and trying to keep from falling flat on my tush. Getting into her car was an adventure, everything smooth and silky, just sliding across the seat almost making me come. We were at the club before I realized I had no way to get home, my car still in my garage at home. I never did see my wallet, ID or any of my credit cards, presuming that I will not have use of any of them for the foreseeable future.

I was given an area to work, reminded what my duties are and patted on my butt to get me in motion. The first half hour I was pretty much useless. Learning to walk in the heels and the swaying of my breasts as I made the rounds totally consuming my limited abilities. When I leaned over to pick up some dishes my breasts almost escaped their confinement, the first time it happened I dropped a few dishes as my hands went to my erstwhile appendages to prevent them escaping the corset. Then I had to get used to the customers staring at me, specifically my boobs. When I was being talked to, their eyes never left my chest. A most disconcerting thing to get used to. I did get some gropes, a pinch or two and two very sore feet in the time I worked my shift. I had doubts my day would ever end, every time I looked at the clock it was only minutes since the last time I looked.

After the club closed and we had cleaned up Cheryl and several of the girls came and took me to one of the booths. I was helped into the seat, and two girls each grabbed a foot, removed the heels and started massaging my poor abused feet. It felt so good. Cheryl wanted to know what I thought after my first night on the job. I told her it was alright, not something I would choose to do, but I managed to live through it. Then she showed me my percentage of the tips, almost two hundred dollars and that was as a bus-ty girl. My pay for the evening would be another one hundred and fifty dollars, making for quite a good night income wise. “Just think at the end of the five years you could save enough to buy the clubs back.”

I let that statement slide by, everything was still all new to me, my breasts and feet the two most prominent things on my mind. Cheryl took me home, advising me that walking alone was now a forbidden task, in the past I have walked from the club to my townhouse, now that seems to no longer be an option. “With that body you will not make it a block before some guy is trying to have his way with you. With those heels and in a corset, he might just get his way.”

Cheryl did help me get undressed, but unfortunately she told me the corset stays. I was handed a nightie after brushing my teeth and we set on the sofa sipping some hot chocolate. She wanted to know if I was still mad at them for what they pulled. I thought about it, but then shook my head no. I am not particularly happy with your solution, but I guess it could have been worse. If I am truthful it opened my eyes to what females go through. Maybe I could have been spared that revelation, but at least I will never be bored. I did inquire if she is serious about the five years, her smirky smile answered that question for me immediately.

You have so much to learn, how to deal with the male of the species, how to maintain yourself as a female and how to deal with being a female. In case you have not figured it out yet, you will have a period like the rest of us, so you need to pay attention. If you get pregnant, you will not have an income for a while, so plan ahead. My face was twisted in shock, red all over and I was swallowing hard. Me pregnant, I hope she is kidding. I tried to get more info from her, but all she would say is that I would experience periods and if not careful pregnancy is a possibility.

She changed the subject, telling me she would pick me up at one P.M. tomorrow, so I had the majority of the morning to do my hair and makeup. For the immediate future until you have saved enough for a car, you will have to ride with me to work or take the bus. I started to say I had a car, but she waved the key to my garage in front of me, not any more. Your identification, credit cards and extra cash have been put in a safe deposit box at your bank for safe keeping along with your car keys. You have a refrigerator full of healthy items and you first gym appointment is the day after tomorrow. We must keep your figure attractive so you will still be able to hold a job, any income you get coming from that job.

When I ran the clubs I had no idea what the girls went through to keep their job. I knew they went to the gym regularly, but figured they just wanted to exercise some. According to Cheryl it is a necessity to help maintain the figure, a sexy feminine figure that is required to keep the job. No one hires or keeps a plump female cocktail waitress. Salads the majority of the time, forsaking anything sweet or rich. Those foods are high in calories, a female’s worst enemy.

When Cheryl picked me up the next day, she took one look at me, then started giggling. I knew why she was doing it, I was a total failure at makeup and hair. She did straighten a couple of things out with regard to my clothes, or I should say my lack of clothing since the outfit I am to wear is just pieces of fabric. The ladies who do the costumes must be having a field day with mine, today’s even briefer than yesterday.

I was helped into her car, then she headed to the salon. There I received another crash course in makeup and hair, with me having to do it again myself. I barely passed inspection, the grins on Cheryl’s face proved she was having so much enjoyment at my expense. Then to the club and to work. The heels were still bothering me some, but not as bad as yesterday. The hardest part for me was the male customers, their staring at me, mainly my breasts, was unnerving. I did think back to what I had done in the past, I guess I was getting what I deserved, because I did focus on certain female attributes more than once, forgetting the person inside. I did make it through another night, but barely. After Cheryl dropped me off she reminded me of my gym appointment, she would be by at eleven in the morning to pick me up. An hour at the gym, then back home to shower and change clothes.

At that time I regretfully remembered working seven days a week for several weeks before I got a week off. Another example of my male ego, just presuming that it would be best for the girls. I did learn later in the day Cheryl had changed that schedule for everyone but me.

The gym appointment was an hour of hell, from one machine to another, never even a minute to relax. I was sweating within minutes and thoroughly soaked by the time the hour was up. Cheryl was there the whole time, her leotard only lightly moist, but with way too much energy and bounciness. Dropped off back at home I wanted to just crawl into bed and forget the world. Unfortunately for me Cheryl saw that and came in to supervise my bath and dressing to work another shift. I hated her, so energetic and Ms. Happiness. I did manage the turnaround in the required time, but barely.

By the time we reached the club I was feeling a bit better, the tiredness waning a little, somehow the exercise did help, it just took some time to kick in. Another shift as a bus-ty girl, each day a little easier. The male attention still bothered me, tonight especially since I was groped and felt up more than a few times. Finally Cheryl pulled me aside and told me how to avoid most of the fondling. Instead of being passive I had to be forward, brushing up against the male customer as I got him water or refilled his drink. Leaning over to expose my cleavage and lightly brushing a tit on his arm or when removing something from the table letting my nipple brush against his face. That way he got what he wanted and I remained pinch free. I doubted her advice, but another hour and I reluctantly tried her solution. Surprise, surprise it worked, so now on top of everything else I was a first class flirt, make that a second or third class flirt, still awkward but trying so hard to avoid the pinches.

It was another exhausting shift, although teetering around in the heels was getting better, my legs were still aching by the time we made it to her car and then to the townhouse. I slipped out of the heels at the door, another step wearing the heels could not be tolerated. Cheryl snickered as she watched me try to walk to the bedroom, I had to stay up on my toes to be able to walk. I tried to walk regularly, the pain shooting up my calves in an instant. I collapsed in a nearby chair and looked at Cheryl.

“Now you know why wearing heels can be so addictive. The tendons in your legs shrink as you wear the heels day after day. Then when you try to walk flat footed again it is impossible. You have the first stage of this affliction, a couple more weeks in the heels and you will be wearing them the rest of your life, even at night when you are just lounging around the townhouse. Since the job requires the heels to make your legs look shapely and sexy there is no way around the situation.”

Another revelation about the female in the clubs that I had no idea about, in fact I was one of the first to suggest the higher heels for the cocktail waitresses since it made their legs so much more attractive to the customers. Now I was experiencing the other side of the coin. Just think five years of this and I doubt I will ever be able to walk normally again. Well normally as in a way a male would walk. Then my mind came to a few other conclusions, the breasts sucked from my body, now the addiction to the heels, the constant use of cosmetics and doing my hair and life as a male in the future looks improbable if not down right impossible.

It was three weeks more as a bus-ty girl before I was moved up. The heels still bothered me some, especially around the townhouse. I had to beg Cheryl to take me shopping for some mules, something I could just slide my foot into when headed to the bathroom or kitchen. I had lots of heels, but all with some type of strap. My nails had been lengthened twice in my weekly appointments at the salon. Now they were almost three-quarters of an inch past my finger tip. I could get the strap into the buckle, but not anything else. I did notice the girls had no trouble with their straps, accomplishing the task with ease. When I asked how they did it, I was told I would eventually be able to do it myself, it just take time to get used to the nails. I was doing better with the breasts, I could actually get some sleep without rolling over and pinching one between my body and the bed.

My lower anatomy was another matter though. For a male to have something there all the time, and then suddenly it is gone is very hard to get used to. Even after a few weeks when I need to go to the bathroom, I stand there for a minute looking at the toilet thinking that I need to pull out my penis to pee. The reality sets in and I have to remove clothes, lower my panty and then sit. The water spews forth, not necessarily in a neat and confined way, then having to wipe to get the remaining moisture requiring some additional effort.

When my cocktail waitress costumes were shown to me I let out a low groan. Cheryl was already giggling, she was the one that had brought them to my place. She wanted a fashion show, really it was only so she could see me in the creations and get some more giggling at my expense. I wondered what I had done to the wardrobe ladies that was so mean that they had to take revenge on me. It was a bodysuit like all the other costumes, but in my case it was very thin and almost transparent.

Hanging on the hanger with the bodysuit were three pieces of lace, each piece gathered up and stitched to stay in a ruffled circle. In the middle of the circle was a few diamonds to make sure anyone’s eyes would be fixated on my breasts or sex. They were to be glued on, then the bodysuit slid over my body and buttoned up the back. That meant I would be caught in the bodysuit unless I could get someone to undo my buttons. The buttons were extremely small and looked like diamonds. The last button was at my anus, positioned just as my body curved under at my hips.

I quickly came to the conclusion that I would not be eating anything or drinking anything until my shift ended. That way I might be spared some humiliation and embarrassment. After I had the first bodysuit on I discovered the other fault in the design. No support for the breasts, meant that they would flop around on my chest, causing the glued on fabric to move back and forth across the bodysuit. Just wearing it for fifteen minutes had my nipples so erect that I feared I would come instantly if someone touched them or fondled them.

Five years of this, even if I performed flawlessly I doubt I would be in any condition mentally to even remember my name, much less do any other type of job. Cheryl had planned well, I was stuck in a situation that would have me so stimulated that any touching would send me off on a wild ride of female orgasms.

She had stopped her giggling just staring at me with her usual smirk, knowing that I figured some of this out and now knew I was screwed, both physically and mentally. I had been out maneuvered by one of the best, now having to start over, learning everything new and then have to try and live with the feelings and emotions. That last part probably the hardest. As a male I made decisions, building the business up from nothing. However feelings and emotions never were a part of that process. Now simply wearing sensual clothes had me sexually excited, and constantly frustrated. The equation had changed, simple business decisions had suddenly morphed into new life experiences, threatening to disrupt any and all normality in my life.

I did finally got into a routine of sorts, each day getting ready for work, dressing in the ridiculous costumes and working my shift. When my first two week period ended, I was so looking forward to some time off. A whole week to do what I wanted, not have to dress, do my makeup and hair everyday and then teeter on my heels for eight hours. Well it didn’t quite work out like I had envisioned. By the second day I was pestering Cheryl to let me come back to work. Without things to occupy my mind, my thoughts were on my body, my lack of what I used to have, and a pair of breasts that were determined to drive me insane. The lack of the lace circles and rubbing against the rest of my costume left me wanting for anything to stimulate me. The final straw was when I was rubbing my breasts against the door frame trying to recreate the feeling. I guess I could have just rubbed them with my hands, but in reality I was afraid if I did I would not be able to stop. Just the thought of my fingers on my nipples was so intoxicating.

We will not talk about my period, when first mentioned I thought it was a prank to tease me. Well when I awoke one morning and the crotch of my panties were bright red, I panicked. I called Cheryl, not knowing anything else I could do. I was scared to go to the hospital, to be probed and examined by a male just too much. So I called Cheryl. Once she quit laughing she told me she would be right over, and instruct me in the process of dealing with my period.

I let her in the door, my hand holding a towel to my groin trying to stop the blood flow. I was taken to my bathroom, sat on the commode and then she retrieved a tampon from under the sink. She peeled the wrapper off and made me insert it in my vagina. As it slid in, I almost fainted, the pleasure of it sliding in had me weak in the knees and gasping for breath.

Jerked up from the commode and told to take a shower, making sure to wash down there thoroughly. I was confused and out of it standing there in the bathroom naked with a string hanging from my female sex. The water did feel good as I entered the shower, and although I did wash down there, I did it very gingerly. I swear I could feel the tampon expanding as it soaked up the red liquid. I knew I was not a real female, but how I ended up having a period baffled me. Gawd, if I have to deal with this every month, life sure as heck took a wrong turn in my case. My period did pass eventually, although the next two days were quite miserable. I was allowed to work the bar, keeping me somewhat off my feet and allowing me to sit every once in a while, although still in the heels. For that I was very grateful.

Once the aches and pains eased up some it was back to my job as a cocktail waitress. I could have taken part of my week off then, but being home alone with a distinctly female body, made my mind go bonkers. At least at work I was busy, not having time to think about my situation and what I was doing. Invariably in any thinking the five years time requirement came up, instant depression over coming me. Five long years, if I even last that long I am sure my feminine behavior and actions will be so ingrained it will be impossible to rejoin the male gender.

I am not sure when it happened, at least a couple of weeks later to my thinking. Instead of dreading life every day I started looking forward to going in, somebody to talk to, even some of my customers seemed interesting. Maybe I did not want to return to my male existence. The clothes ceased to be a problem, often after donning my brief little costume I admired myself in the mirror, my breasts and hips quite seductive. Because of that seductiveness I was often chatted up, the male doing all kinds of things trying to get me to notice him. It was like I was suddenly popular, lots of interest in me, people talking to me endlessly about anything and everything.

As a male none of that happened, I asked a question and it was answered. If I made a comment and they wanted to respond they did, but nothing more. I am sure most of them just wanted in my panties or to fondle my breasts, but they kept trying day after day. I was hugged by everybody unless I pushed them away. Even though it was not genuine affection in most cases, it still felt good.

Cheryl did notice the difference in my behavior, complimenting me on finally facing my fate head on. She started hanging around me more, often coming to the townhouse early in the morning just to talk. Then on the days I had my hour of gym she would come early and we would shop before heading to the gym. I missed having her around, eventually asking her to move in with me. She held off for a couple of days, then when I pleaded with her to move in with me she did agree.

I did not have much time away from work, begging to not have any full days off, the loneliness and being aware of my female additions still too much to deal with my myself. Yeah, I now had adjusted to having them all the time, but alone thinking of the long term was just too depressing. Then one day early in the morning I was thinking of the five year term again and a sudden realization ran through my mind. If the time had expired and I had returned to my male existence, I would have none of the things I have now. The first thing that popped into my mind was having no breasts. I immediately cupped my breasts through the nightie I was wearing and caressed them, the warm erotic feelings spreading through my body. That was the last time I thought of returning to the male persona.

Cheryl and I have become a couple, a couple with both of us as females. I still work at the clubs as a cocktail waitress, now entering my sixth year in that position. Cheryl several times has offered me the manager position at the Orlando location, but I routinely turn it down. I have saved quite a bit of money over the years, my tips responsible for most of it.

I did get access to the trust fund, but promptly gave it to Cheryl to use as she sees fit. So what does she go and do, she buys ten more clubs. I do get to go with her when she visits the other clubs, her taking care of business and me working a shift as a cocktail waitress.

At the time the original agreement came into being I dreaded everything about it. Yeah the money was good, but living and working as a female had me scared to death. It was staring over again right from the bottom. I look back now fondly, the best thing to happen to me in this lifetime, well that and having Cheryl as a soulmate.

Starting over again, simply wonderful.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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