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The Cocktail Waitress Belladonna I shuddered as I looked at my reflection in the mirror as the stylist moved to touch up the makeup where my breast forms met my chest. "Looking good," Doug said as he gave me a thumbs-up from the seat that he had watched various bits and pieces of my feminization from. I shook my head in response before I gazed into the mirror and became transfixed by my reflection. What I saw made me sick to my stomach. From head to toe I looked every bit a woman, and not a particularly respectable woman at that. My feet were imprisoned in pointed toe, bronze colored pumps that were contorting my feet into an unnatural position that was quickly turning painful even as the ankle straps of the shoes hugged my skin. My complaints about that resulted in a smile from the makeup artist, Amy, who told me that I would have to get used to it since I was going to be spending a full week in them. I almost felt as if Doug had paid her extra to keep reminding me of that as she never missed a chance to do so while she directed my metamorphosis from a dapper young businessman into a busty tart. Amy pulled her hands away from my false breasts for a moment to put down the makeup before her hands cupped the sides of my breast forms and squeezed them. I felt the realistic forms jiggle as Amy laughed and said, "Sorry, I rarely get the chance to do that to a man." "There's a surprise," I muttered, sure that no man would ever willing wear the weighty, flesh toned mounds that were pulling me down. Amy stared down at my faux cleavage with a grin before she said, "The glue and makeup's holding up nice. You can't even see where they stop and your chest starts." "You wouldn't be able to see the seam, if I had something to cover these things up with," I retorted. "But then you wouldn't be in uniform, and, besides, I paid a lot of money for your girls. It would be a sin to hide them," Doug replied with a smirk while I looked at his reflection in the mirror with a scowl. Feeling a headache coming on from the overwhelmed feeling that was overtaking me, I clasped at my head and felt the long, hard strands of the blonde extensions that Amy had spent hours adding to my hair with the help of a hair stylist. The girls had added long strands to my short, naturally brown hair before they dyed it a dirty blonde color with highlights. I thought it looked bad enough when it was wet and lying flat against my head and resting on my shoulders and back. Doug, apparently, however, had paid for something more than that as the girls took to curling my newly long locks. By the time they finished, I had curly blonde hair that was held in place by a can of hairspray and gel. It seemed to cascade down around my head in errant waves that seemed to have been intended to make me look like I had just come out of bed after having more than a little fun. As I pulled my hands away from my hair, I stared down at the acrylic extensions protruding from my fingertips. They were covered in nail polish in a French manicure style that I had long found appealing on the slender fingertips of my female companions over the years. Even though it had been hours since they had been placed on my fingers, it was still strange to see them. My eyes pulled away from them as I gazed back into the mirror at the way my lean legs looked beneath the suntan pantyhose that were covering them. I was humiliated by how they looked in them. Even Doug was leering at them, and he knew who I really was beneath the padding, makeup, extensions and clothes. I had always prided myself on keeping myself fit, and I had been thin my whole life. I was a bit surprised to see how feminine an image I could strike with my lean physique and only a few tucks and padded curves. Doug stood up with a smirk and walked over to me. He walked around me for a moment and clasped the ends of the strands of a few of my extensions and pulled them away from my shoulders. With a smile, Doug said, "You're going to turn a lot heads," before he let the strands of my hair fall back into place and brush against my shoulders once more. I glared at him for a second while I looked up into his eyes. Even in my two inch heeled shoes, he was still significantly taller than me. I knew that Doug would have never looked as convincing if I had won the bet. That alone might have made me decide to not go forward with putting him on the floor with our customers. I would have been afraid that a pouched belly, 6'2" guy in pumps and pantyhose might have sent a large number of disgusted people scrambling for the exits with their money still tucked away in their pockets. My figure would not engender the same sort of concerns. In addition to my lean physique, I stood 5'8," average for a man. It was tall for a woman, but not 6'2". I didn't even reach 6' in the uniform's heels, so there was little concern about my height giving me away. The size eight shoes I wear did me no favors in getting out of the public portion of the bet either, unlike the size 12's Doug wore. I shook my head him before I realized how much larger his hands were than mine as well. While I was sometimes jealous of Doug's height, I had never felt inadequate by comparison to him before. Maybe it was his stomach or his prematurely thinning hair, but I never felt that Doug was better than me in anyway. At that moment though, I felt lowly by comparison to Doug. Despite my reluctance to admit it aloud, I made a convincing woman, and I knew that Doug never could. That's why I would be mingling with our guests, while if Doug had lost, I'm sure he would have only been parading around the back areas of our business with his fake tits hanging out. Sure, that would have been humiliating for him, and I would have seen to make sure it was, but it was not as bad as having to parade around with members of the public that were not bound by the no fraternization policy our employees had. That's was part of the reason why I feared what was quickly coming up more than anything else about my feminization. It was also the knowledge that anyone could see me once I walked through the doors that separated our staff from the general public that gave me particular pause. "Did you eat yet?" Doug asked me. Before I could answer, Amy responded, "She ate a nice light salad I got for her." "She?" I muttered before thinking that the salad she gave me hardly constituted dinner. Doug paid me no mind as he responded, "Good, then we can get her out there for the start of the shift." "Do you have to keep calling me 'She'?" I interjected with a snarl. "Put the claws away, Kitten. We've got to keep up the act. You don't want anyone out there thinking that something is off about you. Do you?" Doug asked while Amy snickered. Doug looked down at me with a determined inquisitiveness until I murmured, "No." "That a girl," Amy interjected as she playfully slapped my ass. I jumped a bit and nearly lost my balance in my heels as I blushed and glared at her. Amy shook her head with a laugh while she said, "Now, don't get excited on us. We don't want a tail peeking out at the back of that uniform." I blushed again and shook my head, disgusted by the position I found myself in while I peered down at my faux bust that was practically spilling out of the top of the bustier of my uniform. Despite knowing that the bust was fake and, supposed to be my own, the full rack I was looking down at excited me. My member struggled against its constraints where it was securely tucked away between my legs as my glorified leotard of an outfit kept it snugly pressed against my body. Amy had gone to great lengths to make sure that it was taped and tucked securely so that no trace of any unfeminine bulge was evident. 'My god I'm going to look like this for a week', I thought as I snapped back to reality, remembering that the breasts I was ogling were my own. Every bit of me of me seemed feminine in that uniform as the tight laced bustier was helping give me an hourglass look. As Doug opened the door that lead towards the floor area, I felt sick to my stomach. I put my hands to my sides and looked down, dejectedly, towards the floor. The garish, bright floral patterns and the ruffles around the leg holes of my uniform caught my attention. I knew that it was intended to draw the attention of men and that was something that I feared when I walked out the door to finally face them. Despite the modicum of a covering the skimpy uniform was providing me, I felt naked as I walked towards the casino floor. The thought of being seen by anyone in that uniform, besides Doug and Amy, made me blush to my core. With hesitant steps, I headed down the hallway before I made a turn. I could suddenly hear the crowd of people on the floor while I made my way towards the last door separating me from the public as Amy and Doug walked beside me. As Doug reached for the door, I clasped his arm and asked, "Is this really necessary?" "A bet's a bet," Doug replied with a grin before he pushed the door open. He held it open for me and said, "Ladies first." As I walked through the door, I felt as if all eyes were upon me. They weren't, of course, since the gamblers and our staff had much better things to do than stare at a new waitress walking onto the floor for the first time. Doug and Amy peeled away from me while I walked towards the bar where I was required to report to start carrying over drinks to our cliental. I had been at that bar before, but only as a boss. The bartenders didn't know me though. They didn't know Doug either. We aren't Steve Wynn types. While our chains of casino's are nice, they're not on par with that. We, thankfully, don't have that type of visibility either. As I continued to move towards the bar, I thought back to when Doug and I decided to take advantage of the opportunity to make a dime when the chance to get into the gaming business opened up to us. Our parents were against it, which was no small thing since the money at our disposal was largely a product of our birth. We had grown up together in the same town and had known each other since childhood. Our parents were friends, and they shared my mother's opinion that we both possessed more dollars than sense. Despite that, Doug and I pressed along with our idea to finance and run a casino when the chance came as our state relaxed its gaming rules to raise revenue without increasing taxes. It was not long after that we managed to finance another, and we soon had a whole chain of Casino's to our names. I suppose it was our successes with gambling that helped feed our own need to make bets. Of course, we typically kept our bets in house so that we never lost any money. This bet, however, was different. The stakes were pure humiliation for the loser. The bet was the result of hubris on both our parts. We were both sure that there was no way that we could ever lose. When the results came in, I was crushed. Doug was cheering as if he had just won the Super Bowl. I suppose I would have been just as obnoxious given the stakes of the bet. The loser was stuck working as a cocktail waitress at one of our casinos for a full week. We kidded each other about what we would make the other do when we won. I was still stunned when I lost and surprised when I found out where Doug was going to make work. In fairness, I probably would have reacted in shock no matter what casino he decided that I was going to work in. That it turned out to be the one closest to where we lived, however, was something I had not expected. Despite the fact that no one at that casino, outside of the managers in the building, knew us, I was afraid of what would happen if someone I recognized from the public saw me working on the floor in a cocktail waitress uniform. Given my appearance, those fears had dissipated. Even if someone figured out that I was a man, I believed that no one would place my face to my male name under the dank casino lighting. I tried to put up a happy front as I reached the bar. The bartender grinned as he looked at me. He looked down at my name tag that bore my feminine name in oversized writing and said, "Ruby. Cute name." "Thanks," I managed to respond in a higher voice than I was used to using. The bartender smiled as he handed me a drink and told me to carry it over to another waitress standing on the floor, who was serving drinks to a group of people at a roulette table. I clasped the drink as I walked towards the girl in the identical uniform. My heart almost stopped as I approached her. She looked my girlfriend from afar as she stood there. The chesty build, 5'3" height and long auburn hair made me start to sweat. As she turned towards me, I let out a sigh of relief. The face gave away that she was not my girlfriend. My fears about Doug giving me up abated by the time I handed the girl the drink. She smiled at me and thanked me as did the rest of the table. I quickly realized that the men were already drunk despite the fact that it was only 4 pm. One man reached around my waist and pulled me close to him. I gave an alarmed look at the waitress I had just handed a drink to. I could see her struggling not to laugh. Later that night, she told me that basically every girl responded the same way I did the first time a man decides to get physical on her first shift. She motioned for me to smile. I forced one onto my face as the man stared eye level at my fake bust and said, "Ruby, beautiful, please wiggle that pretty ass over to the bar and get us a round of shots." I was stunned by his directness, but I knew that I should have expected it. Still, the first time it happened, I was taken aback. The other waitress responded for me, "And what exactly would you like?" I made a mental note of the drink he requested and the number shots to get. I smiled and forced myself to respond, "Right away, Sir." "Sir? How old do you think I am?" The man asked with a laugh. "I didn't mean anything by it," I responded with real concern, fearing I had somehow offended the drunk. The man laughed before he laughed, "Don't worry about it, beautiful." I nodded as I walked away from the table, struggling to keep my composure. I thanked God that the girl that had just seen my forced interaction with that drunkard was not my girlfriend of three years. I came to realize that the fear I momentarily had was ridiculous as I made my way back towards the bar. I knew that Florence would never work as a cocktail waitress. Her family was too prim and proper to ever let one of their daughters work in a casino in such a skimpy outfit. Hell, they weren't even crazy about her dating a guy involved in the casino business. They all thought Florence could do better than me, and I couldn't disagree with that assessment. That was a big part of the reason that I knew I couldn't let Florence know the truth about the week I was spending at the casino. I lied to her and told her that I had to leave town on business. She didn't ask many questions other then were I was going. She never did though. When the departure day came, I got in my car and drove to the casino. I booked a room there for the full week so that I wouldn't have to go far en femme. It was all part of my plan to never venture outside of the casino complex en femme for a second. I was relieved that Doug showed no opposition to my plan whatsoever. I can't say I would have done the same if I won. I got to the bar and put in the order with the bartender. He made a few quick jokes before he handed me the shots. I then put them on a serving tray and headed over to the table. I was nervous as I balanced the tray while I walked in my awkward steps, making sure that I was landing my heeled feet perfectly on the stone floor beneath me. The faint sound of my heels clicking beneath me was a constant reminder of my new femininity, as if the perpetual feeling that I was naked was not enough. I smiled as I brought the tray over to the men. I struggled to not drop the tray while I reached onto it and took hold of each shot glass, clutched it and leaned down to hand a glass to each of the men. As the last man took his shot, the man who placed the order gave some rambling toast before they downed the shots. After a cheer amongst the men, one of the men gently spanked my ass. I went to punch the man, but, instead, found him holding out a cash tip. I took the twenty from his hands and thought, 'Maybe it's not all bad.' Carrying the tray, I walked through the floor area until a loud girl read my name tag and shouted my name. As the sound of shouting and cheering went on around us, the young girl in a trampy, bondage dress gave me her order while her male companion nodded alongside her. I took down the order for the expensive drink and headed over to the bar and placed the order. The bartender smirked as he heard the drink the woman wanted. "Trophy bitch, right?" I nodded and said, "I would bet on it." "I wouldn't bet on things if I was you." "Why?" "Betting is for suckers," the bartender replied to the laughter of those standing around the bar. I knew well enough that he was right, as I profited mightily from the saps that came into my casinos and emptied their wallets and pocketbooks for nothing. My present situation further confirmed the truth in his statement. I nodded at the man while I took hold of the expensive drink. As I handed the drink to the girl, she took it from my hand and whirled around, spilling about a third of the expensive drink on the floor and her laughing companion, who seemed eager to take his primed girl up to a hotel room as his prize for the evening. It was a position that I had been in before. I had been that man that got to take a pretty girl for a one night stand by throwing money around, but, now, I wasn't a high roller. I was the girl in pumps, but I wasn't even the prey. I was a lowly employee and servant at everyone's beck and call. While there were some men trying to seduce me, I wasn't getting the same type of flirting that the girls who were not in uniform were getting. The men seemed to believe that they had to do less to sleep with a girl like me, since they assumed they could already touch me because they were my employer's cliental. I was kind of offended by it, but I knew that I had to keep my composure since I could not risk doing something that would hurt the casino's image or reputation. I smiled as I took the tip the girl's companion gave me before I turned away from them. I shook my head as I heard her shouting in celebration that "Don't Stop Believing is the best fucking song ever" while the man's phone began to play the ringtone. The sound of girls cheering drew my attention before another waitress grabbed me by the arm and said that we had to do a bottle presentation. That was the first moment that I remembered that we had instituted the policy after I saw it done at a club in Las Vegas. I shuddered at the thought of doing what I was knew I was going to have to do while I walked beside my fellow waitress. We joined a line of the casino's cocktail waitresses and picked up lighted wands and carried them over head while the girls who took the order carried the heavily marked up bottles of liquor we kept for the self-proclaimed liquor "connoisseurs". I was happy to be moving the product since I knew the amount of money we made on the bottle. Still, I was not so happy to be parading around the casino floor as we drew the maximum amount of attention to ourselves and the men ordering the several expensive bottles. As the girls placed them down, the waitresses who took the order poured the men's first glasses while the other girls and I danced around while the men cheered. When the whole spectacle came to an end, I felt relieved. I knew, however, that I would be repeating the sequence a few more times over the course of the week. As I made my way back towards the bar, I felt a man pat me on the hip as I walked past. Swinging around to face him, the man's hand inadvertently touched my other hip before lingering there for a moment while he asked for drink. I nodded as I took down his order and headed back towards the bar. I got the man his drink and brought back over to him. The fact that he didn't tip me kind of pissed me off after having to feel his gross hands on me. I managed to give the man a smile as I walked away though. The night, largely, fell into a pattern from then on. Outside of the brief respite I got when I got to take a short break to grab a quick bite to eat in the employees' area, I spent the majority of my night refilling glasses for the cliental. The men frequently picked up women throughout the night, who were typically even more intoxicated than the men who they suddenly seemed to find charming. I was jealous of the men for the opportunities at their fingertips. I had taken them so many times before I began dating Florence. Now, I couldn't even take the opportunity if it was mine at that time. I guess it's love when a man turns down a sure thing. It wasn't like the opportunity was mine for the taking that night, however, anyway. The only things at my fingertips were someone else's glasses and my French manicured nails. We had two more bottle presentations, and I lit a few broker and Asian men's cigarettes as they played at the tables. I laughed at their jokes, but any other place was where I wanted to be as the pain in my feet seemed to grow more unbearable with each passing hour. I had no way of actually gauging how long I was on the floor at a time since the windowless and clock less room deliberately kept the time of day a mystery to everyone on the casino floor. I sometimes felt as if that wasn't the only mystery as I seemed to become invisible to all the patrons when they weren't touching me or snapping their fingers while they called out my name for a drink or a light. Many of the cliental also seemed to have an inability to hear anything other then what they wanted to hear, which was typically related to what they wanted to drink. I lost track of the amount of times I had to shout, "Excuse me," at someone who seemed to not be paying any attention to me as I tried to follow up on what exactly they were ordering. As this drew their attention away from their games, this did not make me particularly popular with the gamblers. Despite their expectations, I was incapable of reading their minds. Given the looks and grabs I experienced throughout the night, however, I counted myself lucky to not have that super power for the first time in my adult life. The jokes I heard about my rack and others were enough to give me as much of a window into many of the drunken men's heads as I would want as well. The longer the night wore on, the more obvious it became to me that the non-cocktail waitress employees kind of look down on me and the other waitresses. I noticed that the jokes at the expenses of our bodies came not just from the clients but also from the bartenders, security and the managers. I noticed too that the staff seemed to laugh while we endured the leers, jokes, pinching and bottom slaps that felt so demeaning. I felt as if all the pride I ever possessed had been sucked out of me by the end of the night. When the shift ended at 3 a.m., I walked out of the casino floor area that I had been working on feeling as if someone was stabbing knives into my feet. I headed for the employees lockers and took out my purse. I then headed out into the lobby of the hotel, growing angry that Doug and Amy had neglected to give me anything to change into or, at the least, cover up my revealing cocktail waitress uniform. I shook my head, as there were still a large number of people in the hotel lobby while I walked through it that early morning to get to the elevator. I saw people's eyes drifting towards me. I'm sure they figured I was going to meet some guest to do something that I was not supposed to. Breathing a sigh of relief, I got into the elevator alone and pressed the button for my floor. I rode it up and got off at my floor and walked in silence towards my hotel room. I pushed in the keycard and entered my room. The second I closed the door behind me, I kicked off my pumps and felt a sense of relief even though the pain lingered in my feet. I then walked towards the bathroom and took a quick shower before I climbed into bed. It was not long before my pained and weary body fell asleep. ----------------------------------------------------------------------- The next morning, I awoke feeling groggy. I pushed myself out of bed and showered before I called room service and ordered in breakfast as I did not want to leave the hotel room looking like I did. Not long after, my food was brought up. I answered the door in the pink ladies robe the casino provided and tipped the man with some sweaty, crumpled dollars that men had tossed at me the night before. I struggled to get through the morning before Amy came up to the room with Doug. I was surprised to see Amy again, but I quickly learned that while Doug was in many ways a cheap man, he would spare no expense when it came to maximizing my humiliation. After a shower and a close inspection by Amy to determine that my body was still hair free, Amy styled my hair into a playfully messy style again before I redressed in a pair of pantyhose and the cocktail waitress uniform. As with the day before, Amy laced the corset of the top up for me, tying up the ribbons in the back with ever more force as I sensed the same suffocating feeling that I experienced the day before when I first put on the corset. With the uniform on, they called in a lunch order for me. Once I finished eating it, Amy touched up my makeup on my face and bust and left for the day. Doug exited the room not long after her, but not before reminding me not to be late for my shift. I almost wanted to do so, but I knew that if I did, I would hear it from the casino employees who thought that I really was their underling. I spent the rest of my time lounging around my room watching the television and checking things on my phone. When the time came for my shift to start, I walked towards the door and slipped my feet into the pumps that I knew would leave me in so much pain by the end of the night. As I stepped out of my hotel room, I saw the eyes of some the hotel guests standing in the hallway drawn to me. I knew that that was unavoidable given how I was dressed. I gave them a faint smile as I hurried towards the elevator, hoping that none of them got a good look at me. I was far more nervous about being seen in the lighting of the hotel area than the casino floor, as the lighting was far brighter in the hotel hallways. With a sense of relief, I reached the employees area and put my bag away in the locker area. I checked my appearance in the mirror once again before I began to walk towards the doors leading to the casino floor. As I walked back onto the floor with the same sense of exposure that I felt the first time I stepped onto the floor in uniform, I went back to the same routine as the day before. I scurried around fetching drinks, lighting smokes and listening to flirts that were little more than harassment. Given my ability to keep up the forced cheeriness and delight from the demeaning treatment I received, I was getting good tips and helping to keep business at the casino, which was my main concern. Some of the gamblers felt the need to point out some of the less chipper waitresses. They complained about them and made a few jokes at their expense that I forced myself to laugh at, even as I knew the girls had a reason not to find the jerks all that amusing. Midway through my shift, I made my way to the employees' ladies room. I went through the ordeal of undoing my corset pulling it down my body together with my pantyhose and squatting in the pink bathroom stall. I have to admit, it felt good to feel the cold air on my poor compressed manhood, which seemed to be positively relieved for me to be letting it out of part of its prison as it remained taped between my legs. I then stood up and redressed before I pulled the corset strings of the bustier up tight against me before I stepped out of the stall. I washed my hands and touched up my makeup. I took hold of the purse that Amy had given me to carry my makeup bag in, which I was keeping in the employee locker area. I zipped the bag up and headed for the bathroom door. As I stepped out of the ladies' room, I saw a woman's feet in a pair of familiar heels standing beside a large pair of men's oxfords. My eyes rose to greet Doug's before I realized that it was my girlfriend standing beside him. "Florence, this is the lovely, little lady I wanted you to meet." Florence stuck out her hand to greet me before she realized where she had seen my face before. As she started to get loud, Doug pulled us into the vacant manager's office and closed the door behind him. "What the hell is going here?" Florence shouted. I quickly explained the bet to her as Doug nodded along and confirmed that I was standing before her in pumps, a bustier/corset and pantyhose because I had lost a stupid bet. Florence shook her head and asked, "Why didn't you tell me?" "I didn't want you to see me like this," I responded truthfully. "That's no excuse," Florence retorted, clearly more upset about that the fact that I lied about where I was going than how I looked. "I'm sorry," I replied with genuine contriteness. Florence shook her head and bit her lip before she asked, "Those aren't..." "They're not real," I hastily replied as I touched my breast forms. Florence breathed a sigh of relief before she asked, "Well, how do you like it, Ruby?" I gave her a stunned look as a smile came across her face. I realized that she was simply trying to play games with me before I responded, "About as much as you would probably expect." Doug laughed as he interjected, "Why don't you see for yourself, Florence? That's why I invited you down here tonight." "How thoughtful of you," I deadpanned while I adjusted my name oversized nametag. "At least he was keeping you honest," Florence retorted. "Yes, I'm here to make an honest woman out of Ruby," Doug interjected, prompting Florence to laugh. "With her tits out like that, I doubt you're the only one," Florence managed to respond as she stared at my fake breasts. "Hey, I'm up here. Not down there," I shouted at my girlfriend as I pointed at my eyes and then my breast forms and then back to my eyes. Florence laughed since she had used the same line on me before, probably never dreaming that I would ever be in the position to ever use it against her. She put her hands over her face while she shook her head. Florence pulled her hands away from her face as she turned towards Doug and said, "I think we've kept Ruby away from her duties long enough." "I couldn't agree more. After all, I'm running a business here," Doug replied with a brief laugh. I looked at both of them in silence before Florence shouted, "What are you waiting for girl? Get your tight ass back out on the floor." "And remember, always smile," Doug added as he used he pushed his fingers against his cheeks and grinned. I shook my head and said goodbye to Florence before I went to exit the room. "I'm not going anywhere," Florence responded. "What?" I asked. "Yes, I invited her to see you in action," Doug interjected. "You told her about this? Why was she so..." "I didn't tell her that you were here. I just told that you left a surprise for her here." "I guess I was the surprise," I responded, clearly peeved. "I'll say," Florence answered for Doug. "Don't let us hold you up," Doug said as he gave Florence a bunch of free chips before he told me that they would see me on the floor. I was mortified at the thought of what Florence would think while she saw me serving the casino's clients and dealing with the inappropriate conduct that was directed towards me. I shuddered as I walked through the door that led to the lockers to put away my purse before I headed back onto the casino floor. Not long after I stepped onto the floor, I was called over to get a round of drinks for some gamblers. By the time I brought them back over to the group, Florence and Doug had taken a seat at a Blackjack table. "Oh, Ruby," Florence called over to me. "What can I get for you?" I answered politely with a smile, as I was supposed to. "How about a Vodka and Cranberry for me, and what about you, Doug?" Florence replied. "I'll take a Gin and Tonic," Doug responded. "Coming right up," I replied before I headed towards the bar. I was stopped on my way there to take down another two orders before I managed to place Florence and Doug's orders. I carried the drinks out and served the cliental before I made my way over to Doug and Florence. I placed their drinks down in front of them and said, "Here you go." Florence thanked me before I was sent on my way. As I walked away from them, a group of men called over to me. I walked over and took down their order. The drinks they ordered were not something that we ordinarily gave out to the patrons for free. After I told the man that I couldn't comp his drink, the man laughed as he replied, "I don't need you to comp my drink, babe." "Would you like to settle up or start a tab?" The man grinned as he replied, "Start me a tab. It's on me. I'm the big daddy here." The man's friends rolled their eyes and called him delusional, but none of them reached into their own pockets, so I knew there was more than a kernel of truth to the boisterous man's claims. The man gave me his credit card and sent me on my way. I brought his card to the bar and gave it to the bartender before I collected drinks for the man and his friends. I gave the men their drinks and gave the man who ordered for the table his last. I gave him a forced smile as I said, "Here's one for the big daddy." "I like this girl," the man replied. I shrugged and grinned before he said, "Say, tell me, Ruby, have you ever sucked a dick as big as mine?" The man's crude question stunned me. I was speechless as the man and his friends laughed. The pit boss near the table laughed along with them. Florence overheard the man and shouted, "Hey, loser, I know that girl's got to have sucked a bigger dick than yours." I blushed while I heard my girlfriend's attempt to come to my defense. The man's friends snickered at Florence's words before the man bellowed, "I could show you what a real man is!" "And I could show you what a clitoris is, but I don't want to spoil the fun for the woman who finally spreads her legs for you," Florence retorted. The man clasped him around my waist and said, "Don't flatter yourself. I'd go for a real lady like this little number." My God, that remark almost made Florence fall over laughing. I struggled not to blush too noticeably before the man continued, "Just look at her hair, that's kind you just want to yank." With that comment, I felt a queasiness that was growing normal whenever I was in pantyhose. "And that ass I'd like to ride all day," the man then added. Florence collected herself to say, "Okay. You've harassed her enough for one day." "It's not harassment if she likes it," the man replied as he turned and saw the forced smile on my face that made him think that he was right. The man's friends nudged him to let go of me. I felt a sense of relief to be free from his strong arms. I stared at him for a second and struggled to fight off the urge to punch him. I walked away from the table before Florence called over to me. "Ruby, darling, can get I drink?" "Yes, what can I get you, Miss," I replied out of habit, which had formed quickly for addressing women in the casino while I was working. "Miss?" Florence replied with a smile before she gave me her order. I took it to the bar and got her the drink. I noticed her watching me while I walked to and from the bar. She smiled as she took the drink and said, "Thank you, Ruby." "You're welcome," I replied. I went to turn away from her before Florence said, "Oh, and just one more thing." "What?" "You did a wonderful job," Florence replied as he pulled two dollars out of her pocketbook and stuffed it into my faux cleavage. I blushed and prayed that none of the patrons took any ideas from what Florence had just done. Florence winked at me as she spanked my bottom and said, "Now, go shake what Doug bought you." My girlfriend's treatment of me was not lost on a few of the patrons, who seemed to lose whatever inhibitions about touching me they had. Men and women alike called me over to fetch them drinks. Then, they wouldn't miss the opportunity to paw and grope at me for their own amusement while they gave me their orders or I placed their drinks down. All the while, I had to keep a smile on my face, knowing that it was expected of each of the girls on the floor. Florence just watched the whole thing with a smile and laughed as she gambled with house money beside Doug. I was uncomfortable about how close they were sitting to each other as they shared laughs, which I had no doubt were at my expense. Despite my displeasure, I was in no position to do anything about it while I scurried around the casino floor with my pushed up tits almost bursting out of my top. Neither of them, nor anyone on the floor that could see my name tag, wasted anytime that night before shouting "Ruby" to get my attention to make me get them a drink or a light for their smoke. While I hated doing it for the cliental, getting drinks for my girlfriend and Doug was almost too much for me. They both knew who I really was and why I was on the floor, and they both seemed to take pleasure watching my pantyhose covered ass squirm. Being hit on by guys in front of my girlfriend only seemed to make Florence laugh. The drunks had their hands on me and asked me to do this or that with them. I just replied that I couldn't because of the casino's policy. I was thankful that Doug decided not to correct me whenever he overheard me give my excuse to let the guys down gently. The only time Florence even seemed a bit upset was when a very drunken woman I gave a martini to gave me a slobbering kiss almost on my lips and squealed as she said, "I love you," before she turned her attention back to the gaming table and her husband. Florence gave the woman a peeved look. I thought that she was going to get up and hit her. Doug, however, seemed to talk her down, especially as Florence realized that the woman really had no intentions towards me. She was simply acting like a drunken fool. After watching me for a few hours, I noticed that Florence was starting to pickup her chips and her bag before she stood up. I watched as she walked across the room and came over to me. She waited for me to finish putting drinks on the table and take my tip before she clutched me by the elbow. "Ruby, I want you to come home tonight." "I don't know about that, Florence. I don't have any other clothes besides...," I replied as I pointed at my uniform. Florence smirked and shook her head as she replied, "Well, that's just cruel, but I need you to come home tonight." "But..." "No buts, missy. You're coming home tonight. Is that understood," Florence replied with a playful forcefulness. "Yes, dear," I replied. Florence smiled at me before she strolled away from me and out of my view. I then turned my attention back to working. I finished my shift and collected my belongings in the employees' locker area before I headed for the hotel area to exit the casino complex. My lack of feminine clothing, other then my uniform and robe, was even more galling to me as I had to leave the casino with my fake tits popping out of my top and without even the modesty of a skirt. I attracted a few catcalls while I made my way through the parking lot. I hurried as fast as I could in my pained steps, though I had to slow down to make sure my heels didn't get caught in any of the cracks in the pavement beneath me. I breathed a sigh of relief as I got into my car. I pulled off my shoes and started it before drove I drove my car out of the parking lot and towards the highway that lead to the home I shared with Florence. I spent most of the drive wondering what Florence was going to have say about what she had seen and about the lies I had used to cover up what I was doing that week. I pulled up at the front gate of my development with a sense of unease. The guard smirked as he stared down my top and asked where I was going. After I told him I lived there, he shook his head and stated, "Please show me your ID." I objected, which only confirmed his suspicions that a cocktail waitress would not be living in such an expensive, private development. "Miss, please show me your ID or turn around before I have to call the cops." I mumbled as I fiddled with my pocketbook and took out my identification. With a trembling hand I took it out and handed it to the man. The man took a look at it and stared intently at the picture in silence before he looked at me and said, "Miss, this is a man's identification." "I know that," I responded trying to sound confident and vaguely masculine. "You can't expect me to think this is you," before he tossed my identification back at me. "It is," I said dropping into a baritone that stunned the man. The man laughed and said, "Whatever, miss, sir, whatever you want to be called. I don't buy it." "I live here! Open the gate." "I'm going to have to ask you to leave, Miss." "But I live here! Call Florence Ford at my home. She's expecting me." "Miss, I'm not calling one of our residents at 3:30 in the morning based on some insane delusion." "I'm not crazy. Here, I'll call her. See the number right here," I shouted as I held up my blackberry that was framed by my polished fingernails. I dialed the phone and began to speak to her before I gave the phone to him. As a smile came across the security guard's face, I knew that she had convinced them that I was really the man I claimed to be. The security guard handed me back my phone and said, "Sorry for the misunderstanding, Mister," emphasizing the "mis" in both words. The man opened the gate to let me in, and I drove to my home. I pulled into the driveway and hurried to the door that I was unhappy enough to find locked. While I fidgeted with my keys, I counted myself lucky that it was so early in the morning that my neighbors were not getting a chance to see what the security guard had. I sighed as I took hold of the key to the front door and turned it in the lock. The sound of my heels clicking on my wood floor as I entered drew Florence's attention. "Ruby?" "Very funny," I shouted in my most masculine tone, even though doing so made look even more ridiculous when I walked up to her, still dressed in my cocktail waitress uniform. "Well, look at you," Florence said as she sat in her satin robe sipping on wine. "Laugh it up," I said as I rolled my eyes and removed my shoes, which in retrospect was the first thing I should have done the moment I walked through the doorway. "I've already had my fill," Florence replied with a grin. "I'm glad that you did because the security around here certainly hasn't." "So what?" "So what? We're going to have to move." "Why do we have to move?" Florence replied with a bemused laugh. "You'll know he'll talk." "So?" Florence said before she took another sip of her wine. "What will the neighbors say?" I shouted as I pointed at my bustier. "The neighbors? I've lived here with you for two years. You haven't said one word to the neighbors in all that time." "That's why I like it here!" "If everyone keeps to themselves, what's the harm of anyone knowing about this?" "I have a reputation." "A reputation? For what? You run casinos. No one expects you to be some holier than thou guy!" "It's a tough business. We've got to be tough." "Ladies can be tough too." "I'm no lady!" "I'll say! Your suntan pantyhose are a dead give away. Very trashy, babe." "That's not funny?" I retorted. "To you, perhaps," Florence replied with a smile. "I can't talk about this now. I'm beat." "So?" "I'm heading to bed. We can talk about this later." "No, we can talk about it, now," Florence countered, speaking with a tone that was more domineering than she had ever used before. While I was used to Florence getting what she wanted, it was normally obtained through the use of manipulation. She knew what I wanted from her and played me accordingly to get what she wanted. I didn't know how to process her response, so I shot back, "Florence. I told you I'm tired. We'll talk about this later." Florence shook her head at my commanding tone before she said, "Last I checked, you were the one who was dishonest with me!" "I was, but..." "I need to talk about it," Florence said as she cut off my response forcefully. It was at that moment that I decided to strongly put my nylon covered foot down, "Florence, we'll talk about this later! Do you have any idea what I've been through? The long hours! The fucking pain in my feet, ankles and back that won't go away. The ass grabbing! Do you have any idea what it's like to get your ass grabbed by a drunk, horny man?" "Yes," Florence deadpanned, stunning me before I realized that I had certainly done the same thing to her. I forced myself to refocus before I responded, "Well, it's not the same." "It's not? You're bitching about something that probably every girl you employ in your position goes through! Hell, every girl you and I know has a problem with heels, but they just put up with the pain like big girls, not whiny little bitches." "Put up with it?" "It isn't easy being one of the beautiful, babe. I would think that you would know that by now, Ruby," Florence responded with a wink before she laughed a little. "That's so different." "Why?" "They're girls. They're supposed to be putting themselves through this shit to..." "To what, attract men?" "That's what procreating is all about! Girl dresses to catch man's attention. Man undresses girl. Then Fucking! Circle of life," I answered before I clapped my hands together, briefly touching my elongated and painted fingernails together. "You're a pig," Florence replied shaking her head, while I reflexively tried to hide my fingers behind my back. "Would you say that to a girl in my position?" I managed to have the presence of mind to ask. Florence smiled and laughed at my comment, momentarily defusing the problem I realized that I was making worse for myself each time I opened my mouth. Trying to take advantage of her smiling face, I added, "Now, baby, I got to go to bed." "We have to talk about this first." "No. We don't! This is my house. These are my rules," I responded trying to pull rank given the name on the deed. Florence sneered at me as I tried to make a display of my dominance while I was wearing a bustier and pantyhose. She decided then to make a power play herself as she pulled out her phone and snapped a picture of me in my cocktail waitress uniform. "What the hell? Delete it!" "Oh, no. It's my phone, my rules," Florence retorted with a sneer. Feeling weak and desperate I made a foolish lunge for the phone. Florence was a bit more rested and spry than me and easily got out of the way. As she threatened to send the picture to my parents if I didn't sit down, I thought better about what I was doing. I sat down on the couch before she pointed to the bottle of wine on the table and said, "Pour yourself a glass." I pouted as I followed her command and sat back in my seat while she sat across from me and took hold of her drink. After I took a sip, Florence shook her head and said, "I can't think straight anymore." I gave her a dumbfounded look, not knowing what to say that wouldn't make my situation any worse. Consequently, I kept my mouth shut. Florence shook her head as she added, "You know what? We both need some time to think. Why don't you just go to bed." I shot Florence a flabbergasted expression as she was telling me to do exactly what I wanted to do in the first place, in total opposition to her forceful, earlier demands. Not wanting to look a gift horse in the mouth, however, I nodded and complied with her order. I practically crawled up the stairs and went into the master bedroom. I undressed and felt a sense of ease as I slipped under the covers of my own bed. The sheets and blanket felt different to me as they rubbed against my smooth skin. I rather liked the feeling, which was evident given my hardened manhood pitching a tent in the sheets. I was happy that Florence didn't catch it as I feel asleep before she came up the stairs. I slept very little that night, frequently waking up throughout the night. I was relieved to see that Florence joined me at some point in the night. It made feel a little more at ease about our relationship, but I knew that we had a lot more to discuss ahead of us. ----------------------------------------------------------------------- I woke up the next morning feeling drained. I opened my eyes and stared at the breast forms that were obscuring my view of the clock I typically looked at in the room when I was in bed. After forcing myself up onto my elbows, I saw the time on the clock and got out of bed. I then headed for the shower. I showered for a good half an hour while I inspected my body for hair. Relieved to find that there wasn't any, I got out of the shower and put a towel around my body. I walked back into my bedroom and looked around for something that would cover my adhesive augmented top for the trip back to the casino. There was nothing that would work accept for the uniform so I resigned myself to putting it back on. After putting on my pantyhose from the day before, I stepped back into the uniform and brought it up my waist. I positioned my faux breasts in the bustier of the uniform and reached around my backs to tighten the corset laces. Florence walked in and smiled at the scene playing out in front of her before she said, "Let me help you, baby." "Thanks," I replied, blushing because she was seeing my cross-dressing routine. It wasn't any worse than what she saw the day before, but I was still embarrassed to let her see me put on such a ridiculous outfit. "It's my pleasure. You know you really should have told me about the bet," Florence replied as she pulled the laces. I cringed a little from the pain as I replied, "I'm sorry about that." "But that was not the worst thing," Florence responded. "What was it?" I asked, immediately regretting the question as I knew the answer. "It was that you lied to me," Florence replied as she pulled the laces even tighter, practically forcing all the air out of my lungs. "I'm sorry," I struggled to say. "Sorry because you got caught," Florence replied as she tied the strings to the bustier behind my back. "No. I'm really sorry for lying," I replied. Florence looked me in the eyes and said, "Well, I think you've been punished enough," before she patted me on the ass. "Thanks," I replied. Florence placed a kiss upon my lips and said with a straight face, "You know you can never ask me to wear heels again after all your bitching last night, right?" I sighed as I nodded. A smile came upon Florence's face before she reached for my purse. She took out the makeup bag Amy gave me and applied cosmetics to my face and on my faux breasts. When she finished, we went back down the stairs. Florence lent me one of her longer coats to give me have some modesty once I stepped out the door. I put on the heels right before I kissed Florence goodbye and left my home. I then hurried to my car, hoping that my neighbors would not see me. After getting into my car, I pulled out of the driveway and headed down the road that led to the entrance gate. I was let out far more easily than I was let in and drove towards the highway. Once I reached the casino, I headed into the hotel lobby and went up to my room. As I walked in, I saw that Amy was waiting for me. She peered up at me from the couch and said, "Where the hell have you been?" "I went home with my girlfriend last night." "Your girlfriend or girl friend?" Amy asked for clarity. "My girlfriend." "Really? How did she take it?" Amy asked with raised eyebrows. "Pretty well, under the circumstances. There was some unpleasantness. I'm going to kill Doug when this is all over, but it wasn't that bad." "Don't blame him. You both made the bet." "Yes, but he's the one who ratted me out to my girlfriend," I countered. "Fair enough," Amy replied as she shrugged. I pulled off my wife's coat and a grin came across Amy's face. She examined me up close and said, "Your girlfriend helped you dress, didn't she?" "What gave it away?" "Your laces aren't that tight when you tie it yourself. And that makeup, she did it, didn't she?" I nodded prompting Amy to grin and shake her head, "It takes all types." "What's that supposed to mean?" "Nothing much," Amy replied before she told me to change into a fresh uniform. I was not opposed to that since the uniform I was wearing had a slight stink to it. I undressed and redressed in a clean uniform and pantyhose with Amy's assistance before she called in a lunch order for me. Amy left as I ate and tried to relax while I waited for my next shift to begin. As the time came for me to back down to the casino floor, I freshened up my makeup, grabbed my purse and put my feet into the bronze pumps I wanted to burn with every fiber of my body. I went down into the casino and put away my pocketbook in a locker before I headed back onto the floor. I worked for a few hours. After I grabbed a late dinner, and the second half of the shift started, the cliental grew more sloshed, free spending and grabby. While I had never been bothered by any of this before, as it certainly helped my bottom line, dealing with drunks while sober was growing to be every bit as annoying as the groping was degrading. Still I soldiered through it with a forced smile upon my face until I heard my girlfriend call out, "Ruby, a drink por favor." I jerked my head towards her and my eyes grew wide as I saw the snickering faces of her closest friends. Their eyes were looking me over from head to toe as they whispered comments between laughs. I was stunned as I walked over to Florence, wanting to shout at her, but not wanting to cause a scene given that I was the one who had everything to lose at that moment. I forced a smile back onto my face as I asked in a faked chipper tone, "What can I get for you ladies?" That comment just brought more uncontrolled laughed from her friends as Florence giggled along with them. They made comments about me that vaguely referenced what was beneath my pantyhose and uniform, but they restrained themselves from basically shouting to the heavens that I was a man in drag. Once they all gave me their orders, I went and fetched their drinks. I brought them back over to Florence and her friends. They laughed as I served them their drinks. Each took care to call me Ruby as I did so. A few of them even felt the need to pinch and at pat my body. Christie, Florence's best friend, went even further by pressing her face against my false rack and taking a picture with a cell phone to the laughter of their friends. I was mortified as I walked away from them and went to serve other patrons. As I served a group of businessmen in town for a business conference, one asked about what Christie had done. I could sense that he was fishing to see if he could get a picture like that, but I noted that the girls were all friends of mine. This made the man look somewhat disappointed before he asked if I could introduce him and his friends to them. Seeing the wedding rings on some of the men's hands, and using my better judgment, I managed to change the subject. I walked away from the table and served others before Florence and her friends called me back over to them. I got them a second round of drinks while they played at their table. I brought the drinks back, and the girls grew more aggressive with me. I suppose the fact that they had a drink them, knew me and knew that there was a man under the bustier and pantyhose, made them think it was perfectly acceptable to step up their fondling of me. I was a bit embarrassed by it, but I was also turned on by having my girlfriend's pretty friends touching me all over, even while they were calling me "Ruby" and were giving me 'compliments' for my girlish appearance. Florence was a bit upset about what her friends were doing with me. She was the only one in the casino that seemed to have a problem with it though. A few minutes after I walked away from the table, Florence stomped over to me and grabbed my arm as she pointed out the obvious, "You don't seem to mind as much when my friends grab as when the boys do." "It proves my point," I whispered. "What point?" Florence asked with an inquisitive look. "That this is a lot easier job to do for a girl." "It doesn?t prove that point," Florence countered with evident anger in her voice. "Why not?" "A girl would probably rather be touched by a man than a woman." "Girls touch each other all the time." "Girl friends touch each other, but they don't grab each others asses, unless they're drunk sorority girls or strippers." "Women like being treated like a piece of meat, just like I like it when your friends do it to me," I responded. Well, given my girlfriends reaction, I instantly regretted that response. Florence shook her head, glared at me and told me to not bother coming home that night. I tried to defend myself, but I was in no position to get into an argument on the casino floor where Florence could spill my secret at a moments notice. Florence walked over to her friends and convinced them to leave with her. In silence, I watched them leave. I spent the rest of my shift bemoaning my words while I rushed around as a servant to the casino's various gamblers that were in my area of the floor. Florence was still on my mind when I made my way up to my hotel room after my shift ended. I pushed the hotel room door open and walked inside. I turned on the light and saw Florence staring back at me intently. Startled, I jumped a little, prompting Florence to smile and say, "Startle you?" I nodded as I clutched at my heart, which probably looked like I was grabbing my breasts given my outfit and what was stuffing it. As I caught my breath, I asked, "What's going on?" "We're going to test out your theory that you like being treated like a piece of meat by a girl." More then a little turned on by her aggressive tone and the way she looked in her sexy black lingerie, I unconsciously tried to take a step back, crossing one foot behind the other, but crumpled to the floor as I lost my balance. Florence laughed at me as I struggled to remove my heels and stand up. I got back to my feet and looked over at Florence as she approached me. Florence cupped her hands over my false bust and smirked. I blushed, embarrassed by the very thought of having my girlfriend feeling up the breasts that I shouldn't have. I watched her right hand pull of my chest as it crept behind my back to reach for the laces to my uniform. Florence pulled me close and kissed me as she undid the laces before the bustier of my uniform lifted away from my chest. With some tugging, it soon fell to my feet. While I felt a sense of relief from getting out of the constrictive uniform, Florence smiled and spanked my rear as hard as she could. She had never struck me so hard and flush. I was surprised by her strength as I jumped to her delight. As I stumbled, slightly off balance, Florence pushed me onto the bed. Shortly after I collapsed onto it, Florence was on top of my body, straddling me. I stared up into her eyes as her toned, smooth bare legs pressed down on my pantyhose covered legs. My member strained between my cheeks as Florence smiled down at me. Florence reached down and pressed her hand against the gusset of my pantyhose. She caressed my manhood as she dragged the cotton of the gusset against it. Florence pulled her hand away and brushed her hair away from her face as she said, "Well, I guess you were right. You like being treated like a piece of meat." She paused before she then added, "Now, let's see if you like being treated like a whore." My eyes grew wide as I felt my manhood surge while I wondered just what Florence had planned for me. ----------------------------------------------------------------------- "Wakie, wakie, sleeping beauty," I heard in my ear the next morning. My body felt sore, and I pushed myself up to look at the alarm clock. I was shocked to see that it was already three in the afternoon. I struggled to get out of bed, feeling exhausted. "Don?t dawdle," Florence replied, sounding quite chipper. I don't know how she found the energy to be so lively. I figure it was the fact that while our evening ended the same, she didn't have to spend so many hours on her feet while having her ass made to feel like a pincushion. Florence pulled me away from the bed and shoved me into the shower. The cold water on my skin woke me up before I adjusted the temperature and took a long shower. I made sure to remove all the meager body hair stubble I had before I stepped out of the shower and toweled myself off. As I began to shave, Florence told me that she was stepping out of the hotel room for a minute. I nodded in response before I gave myself as close a shave as I could. Although the casino floor lighting was dark, I still feared that a faint 5 o'clock shadow might be visible and a dead give away. Florence noticed my lingering in the bathroom as I took my time shaving. Shortly after she returned, I heard a knock upon the bathroom door. I opened the door with the towel tied around my waist before Florence pulled it off of me and said, "This goes on around your chest." Blushing, I stayed still while Florence wrapped the towel around my top. She brushed my hair with her hand before she reached for a brush. She brushed my hair out and put it up in the same style that Amy had put it when she first saw me en femme. Florence then grabbed my makeup bag and said, "It's time to make you pretty." "Oh, joy," I replied. Florence ignored my sarcasm as she began to apply the makeup that Amy had selected for me. I stayed still why she applied it before she finished and stepped out of the bathroom. As I followed her out the bathroom door, I saw a v-neck, sleeveless pink dress with a lace floral print laid out on the bed. "Where did that come from?" I asked. "I brought it up while you were shaving. Doug had it dropped off at the casino for us," Florence replied. "What for?" "For you, sweetie," Florence answered. "For what?" I asked, still confused. "For our dinner tonight." "I've got a shift," I mumbled in response. "No. It's okay. I cleared it with Doug. He's got a got another waitress covering the first half of your shift so that we can grab dinner together." "I hope that dress is for you," I responded. "Are you kidding? I wouldn't wear something that low-cut. What kind of girl do you think I am?" Florence responded with a smirk as she slapped my arm. I reflexively rubbed my arm, a little surprised that Florence could make my arm sting. She rolled her eyes with a smile as