A Sexy, Flirtatious, Cocktail Waitress

It was sheer bedlam in the casino, some group had booked the whole casino and hotel for seven days straight, we are talking major money here. No info on the group was shared down at our level yet, but it was rumored they were major high rollers. The problem was quite a few employees were on vacation, something the casino allowed, in fact encouraged, right after the Christmas holiday. So the powers to be were down interviewing everybody to see who could work extra shifts to fill in the gaps.

I was an assistant supervisor of the waiters and waitresses, having served here the longest and being the most experienced of the group. In fact, I started as a waiter at the casino many years ago. My boss was doing the interviews, making sure anyone that had any free time was scheduled somewhere. Towards the end of the day we met to plan out a schedule to see how many positions we still had vacant. Three hours later we had a tentative plan, based on the fact of everybody showing up at the scheduled time.

Several maids got shifted to waitress duties, especially for the times the buffets would be offered. Some of the more experienced waitresses were chosen to be cocktail waitresses, just not in the main gaming areas where most of the special guests were expected to be.

We were still short in the main gaming areas, a situation that we could not allow. The cocktail waitress in this area often did more than just serve drinks. She consoled the losers, and hung on the arms of the winners encouraging them to play a little more, giving the casino time to win back what it had lost. Kind of a social butterfly, flitting from one guest to the other to keep everyone happy and content.

Their job was to do everything possible to keep the customer playing the games of chance, those duties ranged from giving a massage to the shoulders and neck of a guest to a kiss for luck or to soothe a substantial loss. The position required a keen sense of who to help and where they could be of the most benefit. To be skilled in flirting a prime prerequisite of the position.

If the casino guest was female a waiter would be called upon to perform the same tasks, but in those cases it was usually the female guest that noticed a certain waiter and motioned them over. Where as with the male guests any attractive cocktail waitress would usually suffice. When I say attractive I am implying gals that would be an eleven on a scale of ten in normal society. Heavy in the breast area, nice rounded hips and long hair either loose and framing the face or piled high up on their heads in curls.

One of our best cocktail waitress examples is Vicky, a blonde with hair to her waist, a 42/32/40 figure with killer breasts. She always sported long polished nails with nail art while her makeup was sultry and sexy all the time. With the standard cocktail waitress costume and the six inch heels there isn’t any male that could resist a look of lust at what she represented. The rest of the girls were similar, at least a high ten if you had to rate them. Blondes the preferred hair color of most of them. It was a much sought after job by the gals, the tips they received often exceeding their wages most shifts.

Unfortunately for us Vicky was one of the ones on vacation, in Yucatan of all places. Cynthia was the next most experienced, but being a brunette, not the most popular of the cocktail waitresses with the guests. I did find out that Cynthia was scheduled to become a blonde, a sacrifice she was making for the good of the casino. Everybody seemed to be cooperating, realizing what a golden opportunity this was for themselves and the casino.

Mary my boss kept me after the meeting broke up, wanting to discuss some things with me. I stayed but deep down in my inner being there were alarms going off. She had me get a couple of soft drinks from her refrigerator over in the corner of her office and we got comfortable on her sofa.

She started the conversation mentioning the booking of the rooms alone was worth a third of a million dollars in revenue. One of the principal guests was listed on the official Las Vegas high roller list, an estimate of his gambling losses and wins totaling almost a million dollars a year. He owned several major shipping companies, both sea and trucking and depending on who estimated his total worth a billionaire at worse.

Several others in his immediate party also in that Fortune 100 grouping. The group as a whole was organized by one of his buddies, a week of luxury, shows and lots of gambling. There was so many people interested in joining the group they ended up turning down some, the hotel not having any more rooms available. Since the hotel had a little over three hundred rooms, a major feat. Of course, all members of the elusive group were of the male sex, for some reason the male of the species more likely to gamble than the female.

Mary asked how far my loyalty to the casino extended. I smiled and told her that I looked at my job as a career, not wanting to go somewhere else for more money or a better lifestyle. She had a proposition for me. One that would insure my future with the casino.

She slid over a picture of a female, very similar in looks to Vicky and asked if I recognized the female. I picked up the picture and knew immediately I was in deep do do. They had taken one of my pictures and photo shopped it, the male image changed to that of a female. Hair color now blonde, makeup and long hair flowing over my shoulders and significant breasts.

The only way that I recognized it as a picture of me is the birthmark right below my right ear. This particular picture had the hair swept to one side allowing my ear and my tell tale birthmark to show. Most of the time I keep it covered up with some makeup, but whoever did the alterations to the photo missed it. I tried to play dumb, I am sure I will get roped into this somehow, but I was not going to make it easy for Mary. Hey she is my boss and the smart one so let her earn her wages.

“I see you have found a new girl, does she have any experience at all or is she still green behind the ears.” Mary smiled. Now that we have that handled, I need you in female mode and in heels so that by the time you are needed you will be just the sexiest cocktail waitress supervisor we have ever had. I looked at her, wait a minute you haven’t even asked if I will do it, this is obvious harassment. She just smiled, if you are going to play games with me than I will assume you are on board, just wanting to wind me up.

You have an appointment in the salon in precisely fifteen minutes, so be on time. That is the Turnabout Gurl salon in the west annex, I am sure you can find it. Then after your transformation you are in female mode till the guests leave ten days from now. Everything is paid for so all you have to do is show up. You can thank me later, if you excel in your new position I might even be persuaded to leave you as a cocktail waitress, with your new looks I am sure you will clean up financially, maybe even give Vicky a challenge as sexiest cocktail waitress.

Oh, I forgot to mention you are now known as Fawn, a buxom transfer from our casino on the east coast. Give me a hug, your future awaits. As I stood up I was in a daze, Mary had somehow turned this all around on me presuming I had agreed to this idiotic scenario and was just winding her up. She had half of it right, but got carried away with the other half. I did get the hug and she assisted me to the door, well shoved me out the door to be more precise, pointing me in the direction of the west annex.

I stumbled along in that general direction, not realizing until I was standing in front of the salon that I had made it to my salon appointment. Still on autopilot I walked in and gave them my name, a puzzled look from the receptionist then I remembered that I was now to be called Fawn. Well that was the magic word as several of their stylists came forward, helping me back to a treatment room. Before I could figure out what to do or ask about I was naked and permission slips were slid in front of me to sign.

I have no idea why I signed them, my mind was still back at Mary’s office and her telling me that I needed to convert to the female sex and become a cocktail waitress. I presume any logical thoughts were impossible so I signed and was soon up on a table being stripped of any body hair. From there things seem to escalate, ears pierced, with my nails now extended and polished.

Then an intimidating machine was wheeled in and large cups were glued on my chest right above my nipples. Hoses hooked up to the cups and the pump turned on pulling any excess flesh into the cups, the start of my soon to be breasts. From the size of the cups I will be giving Vicky some serious competition in the breast department.

With the pump on the machine humming away my chair was leaned back and my hair was worked on. First task seemed to be coloring my hair, as a paste was spread over my roots, then worked into the rest of the hair. While the coloring was processing several bundles of long blonde hair were brought in and hung on a small table next to my chair. From the light blonde color of the extensions I will definitely be classified as a blonde, even maybe a little ditzy since blondes of that lighter color tend to be at a disadvantage IQ wise.

Since I am sitting in the salon allowing them to convert me to the female sex, I might have to agree with the low IQ premise associated with that hair color. To think I had allowed myself to get roped into this when my hair was brunette in color. My IQ must be pretty low initially, now being turned into a blonde I am sure it will fail to register anything on the IQ scale now.

Once the hair coloring was finished and my hair again dry they started adding in the extensions. I had stupidly let my hair grow the last year, its length now to my shoulder blades, frequently worn in a low ponytail when working. Now with the extensions there would be little doubt of my gender, since very few males had hair below their shoulder blades. From what some of the other waitresses had said extensions tied in like they were doing to my hair were almost permanent until the hair they were tied to fell out naturally. Maybe Mary was serious about me staying as a cocktail waitress after this current scenario plays out.

It took them five hours to get all the extensions tied in to my hair, a look at the image reflecting in the mirror in front of me was surreal. It seemed like my hair was twice as big as before, the volume of it much more than I had previously possessed. Then we have the length, the tips of my extensions coming down to my waist.

Other than how I look now with the extensions I knew taking care of this new hair would be quite a feat, in my case I can see myself in the salon quite often. A better way to deal with my new mass of intimidating hair.

With the breast machine still sucking my soon to be breasts from my chest, they started applying makeup to my face. The tech explaining it was semi-permanent lasting for up to six months, with only a touch up needed to keep the color fresh and kissable. Not sure that is what I wanted to hear. It is sounding more and more like this masquerade was going to be for the long term, not just for the present group of high rollers. I need to confront Mary on this and find out why I am being prepared for the job like it was to be my long term career with the casino.

Stopping and thinking about all of this I might have waited too long already, breasts, hair, makeup and no telling what else already making me appear as a member of the female sex. A member that can’t just take everything off and return to the male gender that easily.

After the makeup was finished it was another hour before the breast machine was finished with its task. As the cups were unhooked from the machine they quivered some, acting just like real breasts would. I closed my eyes, hoping that when I opened them again things would be like they were before, but the hair laying on my back and shoulders, the taste of the lipstick on my lips and the quivering masses on my chest were sure to keep that from happening. The mirror that had been covered in front of me, now reflected my new image. An image of the new cocktail waitress working for the casino, Fawn is now amazingly real.

They were not through with me body wise, the proper feminine look was administered to my groin, my male member glued back between my legs and covered with a most realistic female looking appliance. It was explained to me that I needed to sit to pee now, just like a female, and of course apply the proper sanitary items when it was my time of the month.

That last statement got one of my you have got to be kidding looks, but the tech performing the procedure simply handed me a tampon and showed me how to use it. It felt more than a little weird as it slid inside of me, but the hardest part was getting used to seeing a string hanging from my new slit, a definite indication of the new body I now occupied.

Some clothes were next, brief and sexy as befitting a cocktail waitress. I swear that most of my body was on display, the cute cropped tee and the barely visible short shorts the only clothes I was allowed other than a pair of sky high heels. It was as I was heading up to the front of the salon I realized I was not given panties or a bra. Still in a daze I made it up to the front of the salon, to only come face to face with Mary, her megawatt smile from ear to ear. I was dragged from the salon, then down to the casino, our apparent destination.

I received a short review in flirting, then Mary and I wandered the floor, making our presence known and interacting with a lot of the customers trying their luck at the tables. We were not employees of the casino tonight, just two friendly ladies out for some fun and maybe meet up with someone special. That thought kept entering my mind as I flirted and kissed some of my admirers. Was I doing this for real? Surely what little common sense I might have possessed had left me some time ago.

Several hours later Mary suggested that we take a break, I agreed immediately, my feet sorely in need of some rest. Mary treated me to a nice meal in one of our better restaurants, my stomach and feet most appreciative for the nourishment and being able to sit down for awhile.

Then the next revelation, I will be staying in one of the casino’s apartments so that I can maintain the role, leaving no chance to escape to my own apartment and my former male existence. As if that would change anything.

The casino had purchased an apartment building nearby a few years ago, allowing the female employees a place to stay close to work and at a reduced rental. Quite a few of the cocktail waitresses took advantage of the offer, since the more time they worked the floor, the more money they made in tips. Living close to work allowed them to spend a few more hours at work, eliminating the daily commute.

Mary had seen to my accommodation, taking away any chance I might have had to slip back into my previous male existence. Of course the breasts, and my lack of anything resembling a male penis had pretty much accomplished that already.

She went with me to see my new apartment, I am sure she just wanted to be sure I was settled in before she left for home. She did gather up my keys for my old apartment and my ID, credit cards and cash before she left. I was told I could eat at any of their restaurants and buy whatever else I needed at one of their boutiques just by signing my name. I quickly thought of how thorough she was, the boutiques at the casino only offered clothes for the female. Of course, any beauty needs would be handled at the salon.

She made sure I was not mad at her for all she had done, then I got a passionate kiss and she left, making sure I knew my first shift started at one in the afternoon. Since it was now two in the morning, that did not leave much time for sleep. I really could not be mad at her, she has been a great boss and we have become quite good friends, maybe a little more than that judging by the kiss I received as she left. That kiss definitely left me in a quandary.

I tried out the bed, it was pure heaven, making me not want to get out of bed to get undressed. I did manage to shed my clothes, then peeked into my closet. I saw only the uniforms for our cocktail waitresses in our standard array of colors. At the bottom of the closet, way too many pairs of heels, none with a heel height less than four inches. The six inch heels were the majority though, a requirement for a cocktail waitress. No other dresses, skirts, or blouses hung on the closet rod, not even a single pair of pants. In the dresser I found a nightie, although it felt better to have it on than naked, there was not much difference.

A note hanging on the bathroom mirror reminded me to use a moisturizer cream all over my body before I went to sleep, and a special moisturizer in the gold bottle on my face. What they had told me about my makeup was true, the cream did moisturize my skin but not one fleck of makeup was removed from my skin. That being completed I sunk back into the bed and was soon sound asleep.

The alarm was persistent, although I do not remember setting it before I crawled into bed. The breasts did cause a change in my sleep configuration, my old way of sleeping on my stomach no longer feasible, much less comfortable. I slid out of bed, staggering to the bathroom, my nipples getting rock hard in the process since it was cool in the room. I used the facilities, flushed, then stood in front of the bathroom mirror and stared at the image before me.

I decided to skip any shower this morning, my mind probably not able to handle soaping up my breasts or vagina, gawd even thinking about it made me sprout a million goose pimples.
I shed the nightie, then dressed in the uniform of my new job, trying my best to get the uniform to cover more than it was doing. The stockings were probably the worst, as they slid up my legs I could swear I was becoming wet down there. The bra was a joke, two small patches of fabric and three pieces of lacy elastic was all there was to it. The rest of the uniform was a gauze/lace concoction that covered up just enough to keep us from being classified as strippers, but left absolutely nothing from being seen. Even though I was dressed my nipples were standing out a mile, and hard, so hard I could feel them ache to be touched.

I debated grabbing something to eat, but decided against it, my nerves already on edge, I didn’t need a queasy stomach on top of everything else. The salon was next on my schedule, way too much hair to deal with and not the slightest idea of what to do with it. I did manage to get a brush through it, so I didn’t look like death warmed over as I made my way to the salon.

The gals at the salon were waiting for me, huge smiles greeted me as I entered the salon. My hair was handled promptly and they made a few adjustments to my clothes, then glossed up the appropriate areas of my makeup. New earrings this afternoon, a bracelet that kept sliding up and down my wrist, and a necklace that settled comfortably in the cleavage of my uniform. As I made my way up front to check out who did I find waiting for me?

Yep, Mary was all smiles as she grabbed my hand and we made our way to the casino. Incidentally she was dressed as a cocktail waitress too, doing her part to fill in. She informed me that a few of the honored guests had showed up early, so we had our work cut out for us. As we entered the main casino, there seemed to be wall to wall people. I glanced at Mary, she just smirked then stepped up to a couple of the gamblers playing twenty-one.

So I guess my new job has already started. I found another table of enthused gamblers playing poker and squeezed in between a couple of them. When one of them looked up at me I leaned over and gave him a kiss on the cheek, then a shoulder rub. He grabbed me when I kissed his cheek, but I twisted loose pointing to his cards, and he resumed his interest in the game. I did pretty well for the first hour, then realized I had become pretty popular. Several of the gamblers that I had flirted with were calling my name wanting me to join them again, since when I was around they seemed to be winning.

I did get grabbed often, with a few drinks in them they wanted more than just a shoulder massage or a peck on the cheek. I did experience several passionate kisses, tongue included and had more than my fair share of breast fondling. I tried to minimize the contact and passionate kisses, but couldn’t just slap them and walk away. So a lot of twisting and turning, then my finger waving about telling them no no. Five hours later the second shift of waitresses came in and we got a break for awhile.

This time I was the one to grab a hold of Mary and drag her to one of the restaurants. As we entered we were led to one of their banquet rooms where they had set up a buffet, for the employees. I did grab something to eat, mostly food that might replace some of the energy I had expelled earlier. I did watch what I drank, knowing that the more I drank the more I would be making visits to the little girls room.

I nibbled on my food, Mary sitting across from me watching me carefully. I had lots of questions for her, but not sure where to start. After several minutes of silence she decided to take the lead, explaining what she had planned with regards to me.

Let’s face it you turned out much better than I expected. Vickie has lost her title of sexiest cocktail waitress, that honor solely yours. The way you handled yourself the last few hours just proves that you were wasted in your old job. As far as the casino and myself is concerned you will be a cocktail waitress from now on.

I will see to the disposal of your old apartment, you can stay at your company apartment rent free as long as you work here. Now to add to all these revelations after the high rollers leave I am being promoted to head of personnel for the entire company, this leaves my current job vacant. I have already turned in the paperwork for you to replace me at this casino. You can still work your shifts as a cocktail waitress, then in your spare time handle any personnel problems as needed.

I don’t want you swayed by any sweet talking high rollers, as they try and seduce you or drag you away from us. I have purchased a chastity belt especially for you and placed it in your room. I will be by later to help you into it, and to make sure it fits you properly. I intend to keep the key, since I have a personal interest in preserving your virginity.

Other than when I am on the other coast I have the adjoining room to yours, so I will be able to make sure you remember who loves you and who will see to your sexual needs. No need to thank me, but I would like to exercise my stake in you, so close your eyes and pucker up.

I felt her lips on mine and her tongue entering my mouth. Her hands were playing with my nipples and I quickly started moaning as her body pressed up against mine. The fondling lasted forever, when she finally backed away I was out of breath and panting.

The chastity belt fit way too snugly, it taking Mary almost an hour to get me into it properly. When the lock clicked I swallowed hard, but soon was moaning as her lips attacked mine and my nipples became rock hard. After I was assaulted for the second time today, we lay on my bed holding each other tightly.

I thought of what I had become, happy to be a sexy flirtatious cocktail waitress now. A life so special and diverse and a lover who simply adores me.

© 2016 thru 2024 by Francesca