Winning Big in Las Vegas

I was in Las Vegas staying at one of the “lesser” hotels, playing the slots to kill time waiting for a “Shemale” show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surrounded me discouraging my flamboyant foray.

I was playing a progressive slot with little expectation when surprise of surprises, bells started ringing and lights began flashing and I realized I was a big winner. Now, being the big winner is a relative term. At this hotel, playing this game and hitting it big meant $10,000. By Las Vegas standards that’s small change but to me and to this hotel we were talking about a lot of money.

Casino employees came around and congratulated me and a picture was taken of me accepting an oversized check from the casino manager. I was then asked to accompany the manager to his room where I assumed that I would receive my money. I assumed wrong.

The manager Ben Desay told me that they would pay me, but they couldn’t pay me that day. I objected and made mention of the State Gambling Commission and how this treatment could cost the hotel their license.

Ben then offered to comp my room and to comp all room food and beverage charges and he assured me that I would still get paid tomorrow. I was still resistant until he offered to “Treat me like a Whale.”

I knew that “whale” was a term used in gambling circles to describe super high bettors. These individuals were offered plush rooms, free meals and the best tickets to shows. They were offering me the best of everything.

I wasn’t swayed until I was offered the “Full Sex Package.” This program was guaranteed to fill all of my wishes and had testimonials from “Jim G of Terra Haute, Indiana” and “David V of Walla Walla, Washington,” both of whom assured me that I was in for the time of my life. With assurances like that, how could I loose?

I was told that I could begin whenever I wanted and I decided to have a good nights sleep and get a good start in the morning. I knew that prostitution is legal in Nevada but illegal in Clark County where Las Vegas is located and I assumed that I would have to travel out of the city to get full value of the “Package”. I had underestimated Las Vegas.

The next morning I was greeted at my door at a prearranged time by a lovely lady named Celeste. She was wearing 4 inch tall high heels, a black wool suite with pencil skirt and a white silk blouse. While lovely, she would have to go some to be valued at $10,000.

Celeste diplomatically informed me that she was part of administration and not part of labor and that she would escort me through the process. We left the hotel in a limousine and we quickly arrived at an office building located off the strip. I followed her lead and we eventually exited an elevator on the third floor and we entered an unmarked office.

In a short period of time it was explained to me that I was in a psychoanalysts’ office and that the good doctor specialized in sexual therapy. She (and I was glad to hear that it was a she) had specialized in sexual satisfaction and had done research in the field of sexuality for a number of years. My sexual package would begin with her analysis of my interests.

I thought that I already knew my interests and didn’t see the need for the analysis but I was assured that it was worthwhile and it was included in the package. “People pay thousands of dollars to get this kind of analysis. I can assure you that it will add to your sexual enjoyment for the rest of your life,” said the doctor.

I was hesitant since I had a few unusual sexual interests that I really didn’t want revealed but perhaps I could get by without delving into these areas and if I could really add to my sexual enjoyment then all the better. I simply promised myself that I wouldn’t discuss anything other than normal run of the mill sex. I agreed to go through with the analysis.

I was led into the examination room where I expected to see either a couch that I would lie on as the doctor probed my inner most thoughts, or a typical medical examination room with an examination table. Instead I entered a room filled with computers and high tech instruments and a high backed chair set in the middle of the room.

I was told to sit in the chair which was then adjusted to a slightly reclining position. I assured the doctor that I was very comfortable. She then told me that I would have a helmet placed on my head. The helmet was a very expensive virtual reality device. I needed to understand that the helmet would be clamped in place and that I would have to sit through the entire program. My legs and arms would be locked down so that I wouldn’t upset the equipment. I would have access to a button placed near my palm on the arm rest which I could use to signal the doctor if I wanted to stop the program. Stopping the program would conclude the program. No information would be revealed and I would be required to leave.

I watched the doctor place strong but loose fitting restraints on my wrists and ankles. I could move a little but I couldn’t slip the restraints. She then showed me where the armrest button was and I tried a test push which immediately released my wrists and ankles. The doctor told me at that point the helmet would be released and that I would be told to leave the building and that I would not receive any information, nor would I receive my winnings. I agreed to the terms and signed my name to the document that outlined the agreement. I figured that this was the catch. I would see something so bad that I would call an end to the “analysis” and thus be cheated out of my winnings. I was determined to see this through no matter what. I would not be cheated.

The doctor then brought out the helmet, which looked like a high tech motorcycle helmet, with an opaque face plate and a trunk line of wires that connected the helmet to a computer.

It was explained to me that I would see pictures and be able to watch little plays on the face plate and that it was just like watching television. While I watched the show, sensors in the helmet would record my physical response such as respiration, blood pressure, pupil size, etc. which would indicate my degree of interest in the activity displayed. Many years of research went into developing an algorithm that would optimize the sexual pleasure of the participant depending upon their response to the visual stimuli. Areas that I had no interest in would be quickly excluded from the program while my actual interests would be explored in depth. I was again strapped in and the helmet was placed on my head. The doctor touched my arm which was the pre-arranged signal that the program was about to start.

I could hear soft music and saw various color patterns on the screen. I was afraid that the screen would be too close and out of focus but the design was good and I could clearly see the colors unfold. Soon the colors were replaced by three clothed females dancing seductively.

Moving the joystick located near my hand I was able to propel myself around the women. With the virtual system I was able to move around the woman. I moved behind them to see what they looked like from the backside (they looked good) and I moved to look closely at their faces. I moved three dimensionally, flying above and hovering over them. I then returned to the ground maneuvered around the three ladies, learning the subtleties of the controls. I was able to lie on my back and look up at the women. After some trial and error I eventually amused myself by crawling on my back and looking up the ladies skirts. They were wearing rather sexy underwear. The computer generated beings didn’t respond to me. It was as if I was an invisible man.

Music began to play and the computerized ladies stepped over me. Soon, males entered the scene and each of the females was soon physically engaged with a male actor. The action escalated and soon all clothing was removed and the couples were engaged in various sexual acts. On the right I saw a girl giving a blow job to a guy. In the center we had the standard missionary position. To my left the guy was screwing the girl in the ass.

The scene kept changing and soon there was a man eating out one of the girls while two of the naked girls were making out as were two of the guys. Soon one of the guys was sucking on the other guy’s dick while the two girls were playing with each other’s tits. I didn’t even bother to see what the guy and girl were doing.

There were threesomes and foursomes and moresomes. Bondage was introduced and any combination that can be conceived was displayed. Whips were brought out and women were whipped by men, then men were whipped by women, etc. A man came out dressed in a baby outfit and he was coddled by the women. Soon they were changing his dirty diaper and allowing him to suck on their nipples.

I heard a sheep bleat behind me but I didn’t even bother to look. I had no interest in pursuing that opportunity. The last thing that I needed was to discover a new perversion that involved farm animals.

Eventually a naked man came out and the ladies dressed him in a corset, panties and bra. I knew that this was going to be a problem because I could feel my penis rise to attention. If this program was worth anything it would have recorded my excitement. Soon more men were being dressed in women’s clothing including one who had on a french maids outfit. One man was dressed as a ballerina complete with the obligatory tutu.

Another man was dressing as if to go to a square dance, first putting on gold lame sissy panties followed by a yellow double skirted petticoat. A red and gold three tiered skirt was placed atop the petticoat while the man was assisted by a lady who strapped a white bra around his chest and then added what appeared to be silicone inserts. A white eyelet blouse was added to the ensemble as were a pair of white low healed single strapped dancing shoes. I would kill to be in those shoes. My penis was rigid and I was breathing heavily. It turns out that I’m not very good at hiding my prurient interests.

Men were plucking their eyebrows and putting on lipstick and eye shadow and my nipples were as hard as my dick. I was amazed at the expertise the men displayed while putting on their makeup. I would be willing to buy a DVD of this part just to replay the makeup part.

Women came out dressed as men and another sexual orgy ensued. First there were women dressed as men with men dressed as women, then all other combinations. One of the women unzipped her pants and pulled out a rubber penis. A man dressed in a pink chiffon dress was soon on his knees sucking on the realistic dildo. I would like to be that man.

One of the men bent over and his dress was pulled up over his back and his panties were pulled down. Next fingers were dipped in a jar of lubricant and the fingers slowly lubricated his butt hole. Next one of the cross dressed females opened her fly and took out her pretend cock. You know what happened next.

I spent a lot of time rotating around two of the she males who were heavily into each other. There were all sorts of ass grabbing and face kissing and clothing rearrangement followed by dick licking and finally mutual cock sucking. I found that I could maneuver in ways that weren’t possible in the real world. I could go between the men and focus closely on the lips and cocks, area that would be normally excluded from view by body parts. I could actually go under people and see various intimate parts.

At that point, to my disappointment, the picture dissolved into a myriad of colors as the program ended. I realized again where I was as the doctor removed the helmet from my head. “That was fantastic” I exclaimed and she indicated that I was displaying the usual reaction. I told her that she should market this thing as a computer game or in a computer arcade.

She understood the attraction that the program could have on the masses but she also knew that it could also be used in a harmful way. She told me “My research should only be used for enlightenment and betterment. I’m not the world’s entertainer.”

I then tried to get a few more hours on the gizmo, saying that I had just won a fair amount of money and that I would be willing to pay handsomely for the opportunity. She would not agree to my suggestion. This was not a game! There could be no deal. My session was over. The report would be issued later that day. I asked how I would get a copy but was told that I would have to get the copy from the casino since they paid for the testing.

Celeste drove me back to the casino. I tried to get Celeste to get me a copy of the report but to no avail. She did call Ben, who told her to have me meet him “backstage.”

I followed Celeste into the bowels of the Casino and came upon Ben sitting in a chair having a facial. I told Ben how much I enjoyed the testing and asked if I could get a copy of the report or if I could get another session with the doctor.

Ben stated “I know what you mean. I had a session with the doctor and thought it was great. Unfortunately the doctor is probably the only person living in Las Vegas who has ethics. She won’t let you have an extra session. Hell she won’t let me have an extra session. You can buy the report from me in trade for your winnings if you want.”

I declined saying I was interested but not stupid.

“Suit yourself” replied Ben. He then suggested that I get a facial. “Have a seat. Sandra here will make life worthwhile. Sandra, give this man everything he desires. It’s all covered. All on the house.”

Lovely Sandra motioned to the chair that Ben vacated and I sat down. Sandra asked me if I did much in the area of skincare. I admitted that I did not and with a knowing grunt she proceeded to lather on various emollients on my skin. There was discussion of blackhead removal and softeners and moisturizers and pore reducers, all areas that I lacked knowledge.

While swathed in hot towels another person came into the room begging Sandra to do his face. “We have to go on in 30 minutes and I just don’t have the time to make myself up” said the mystery intruder.

Sandra asked me if I could just sit with the hot towel as she took care of Renée. I agreed out of sheer interest in the process. Renée grabbed my hand and said “Thank you sweetie you are a dear” and sat in the seat next to me.

I removed the towel and watched as Sandra transformed Renée’s’ face from that of an ordinary man into a goddess. Renée then popped up, gave Sandra a kiss on the cheek, squeezed my hand again and told us that we were both dear’s for putting up with her.

Sandra and I talked about the transformation and she told me that most men have facial virtues that they don’t even know about. “For example you have beautiful eyes and with just a little bit of work they would put most women to shame.”

Before I knew it she was applying eye liner and eye shadow. I protested saying that it would make me look weird. “Honey, in this place the only guys that look weird are the ones not wearing makeup.” I had to admit that my eyes did look spectacular, certainly better than after any of my personal attempts.

It didn’t take long before she was working on the rest of my face. “It’s just the two of us and you have such nice cheek bones, you should see what you would look like with your face professionally done.” How could I resist?

It took less than 10 minutes and the results were amazing. Sandra had accentuated my cheekbones and had minimized my eyebrows using a white pencil to transform my thick brows to ultra thin brows. She then blended in the white brows with some skin tone making it look like I had severely arched eyebrows. I loved it. Plum lipstick with raspberry lip liner, false eyelashes and “Deep Purple” eye shadow and I was ready for the Miss America pageant. I looked good from the forehead to the chin but I wasn’t in any position to continue the charade.

I admired the look and congratulated Sandra and I said “You may as well take it off; I can’t go out looking like this.” Just as I finished, in stormed Renée, now dressed as a waitress with 4 inch white pumps, a short, pink skirt with white frilly edging, a white short satin apron, a tight white blouse unbuttoned to show an ample cleavage that miraculously grew in the past 30 minutes, her beautifully coiffed hair was adorned with a satin pillbox hat the color and material of which matched her skirt. I was truly envious of the bitch.

Renée immediately exclaimed “Can you believe it, I give her a job and she is as thankful as can be and then she doesn’t show up for her shift? Where in the hell can I get a replacement waitress at this hour?” as she thrust her hands to her side.

She looks at me, points and says “You, you can do it. Come on, help me out here. You saved me once. You were my prince. This time you can be my princess. It’s just a waitressing job.” I’m flustered, I say “I can’t, I don’t have the clothes, I don’t know what to do, and I don’t know how to act.”

But with Renée and Sandra encouraging me and almost pulling me out of the chair I am semi-reluctantly led off to another room where I see many boy/girls in various states of undress. Renée yells out “Rogelio” and immediately a man prances over to my side.

“Rogelio will be your dressing assistant. He is a dear and you are a dear. Do you have a Fem name?” I am perplexed for a moment and then say in a quivering voice, “Well I always liked the name Allison.” Rogelio chimed in “Well that’s not as unique as Cha-cha DeWilde but I guess it will have to do. Ok Allison lets strip down so we can take your measurements.”

Again I am hesitant but I looked around and there were boys and girls all over the place in various stages of transformation. I guess one more naked body wouldn’t be noticed. I stripped down to my socks, and stood there with my hand nonchalantly positioned over my engorged penis.

As Rogelio looked me over he intoned “Sugar, you need to step a little closer to the Nair bottle. Ok, we don’t have time to do you up right so we will have to do what we can. Here put these panties on so you don’t die of embarrassment.”

I caught the pink bikini sissy pettipants with 10 rows of lace. I put them on immediately and was told in an offhand way that the restaurant/show has theme nights, and tonight the theme was “Adult Sissy.”

More wise words from Rogelio “Allison honey, if you are thrilled by frills then this is your night. This is Vegas baby and we always go over the top. You will love the Boom Boom Room”

And over the top we did. Rogelio preceded to swath me in appropriate garb, paying special attention to my novice needs. I received a pair of light purple stockings with metal flecks and a dark purple garter belt. Rogelio apologized saying that he should have given me the garter belt first but that I seemed preoccupied by my “raging hard on” and he suggested that I work the belt beneath my panties and pass the garters down through the legs. None of this was working to reduce my penis problem. When I was having problems hooking the garters to the stockings Rogelio got down on his knees and told me to let him do it since “he didn’t have all day.”

Rogelio attached all four garters without leaving his kneeling position. For the back garters he just moved one arm around my leg and the other between my legs. As he was attaching the garters he periodically moved his forearm up between my legs, gently massaging my testicles. When he reached around my other leg he looked up at my face and smiled and said, “I hope you don’t mind I think my arm may have inadvertently brushed against one of your private places.” He secured the garter and placed his hand directly on my engorged panty encased cock saying “Nope I guess you don’t mind.”

Rogelio stood up, laughed and retrieved a black organza petticoat with a purple leader line around the edge. As I slipped it up my legs to my waist I found that it was really full and spread out almost perpendicular to my hips. Rogelio drew the petticoat a little higher up my waist saying that this wasn’t a hip hugger. I could feel the ruffles at a mid thigh position. Somewhere beneath the ruffles my cock was as stiff as it could get.

I was given a pink bra that matched the color of my panties. It had delightful large scalloped frills across the top edge. I put the bra on, and it was noted that I put the bra on faster than most women. My red face acknowledged the fact that I did have experience wearing a brassier. Rogelio thrust some nice silicone boobs down my bra, and as he did so he took the liberty of running the back of his fingers across my erect nipples.

Finally the dress was produced and there was no question that I would be a sissy. The dress was light purple (Rogelio called the color azalea), and it was festooned with white frills in a V pattern down the bodice, along the Peter Pan Color and at the edge of the puffed, elbow length sleeves. A small apron decorated the front of the skirt followed by tiers of lace edged hems. I almost spurted in my panties when I slipped the dress on; it was so delicious. The back of the dress was ornamented with a large white puffy bow and the ends trailed down towards the hem. Rogelio spent some time arranging the skirt atop the petticoat. He also spent a little more time than was necessary while his hands roamed under my petticoat. He assisted in putting on my shoes, a pair of black patent leather Mary Janes with 3 inch heels.

Rogelio made a comment that some people might have a problem walking in the 3 inch heels but he had a feeling that I could handle them. He was correct. I have owned and worn many a pair of high heeled shoes, although my walks were always solitary in nature.

Next I was presented with a blond, shoulder length wig cut in a bob style with bangs. Rogelio made a few adjustments to the crown and he fluffed out the sides while using hair spray as if he supplied the material to the casino. He then placed a silver tiara atop my head and glued geometric cascade earrings to my ear lobes giving the impression that I had pierced ears.

I had multiple rings placed on fingers of both hand and jingly jangly bracelets placed on both wrists. I was then given a pink ruffled soft sided Tahari purse. The leather wrist strap was placed on my left wrist and it actually attached to my bracelet, making it impossible to misplace as well as difficult to remove. I was told that the purse contained lipstick and makeup and that when I wasn’t working, that I should be working on my face. I transferred my room key and wallet to the purse.

When I walked, I was told that I needed to lead with the purse, my left arm should be held at a right angle to my body, and my wrist was to be limp. As I practiced walking Rogelio pronounced me to be “As pretty as a princess.”

I spent the next three hours waiting on tables. I learned to take drink orders and to deliver the drinks, all with one working arm and one leading arm. Admittedly, I had only half of the tables that the experienced girls had and I did flub a number of orders, but the customers were reasonable. I was hit on by two older “gentlemen,” I declined both offers to join them in their rooms.

Another man thought it fun to run his hand up my inner thigh as I was delivering his drink. He received a lap full of drink for his trouble. I didn’t do it on purpose but he made me jump and the drink landed in his lap. The combination of men with drinks and girls in short dresses is volatile.

The night ended and I had made $230 in tips and I must admit I had a wonderful time. I went up to my room still wearing my uniform and leading with my limp wristed left arm. The next morning I dressed in my usual clothing and met with Ben Desay. We came to an agreement. The cost of my dress, shoes, handbag, wig etc was charged against my winnings. I was credited with three hours of work at the normal beginning waitress rate. I could of course keep my new adornments.

We agreed that I would come back and receive a room at ½ the going rate, which would be charged against my winnings. Additionally, on my subsequent visits, should I choose, I would receive money as credit for gambling purposes, up until I exhausted my winnings.

As an extra bonus, when I showed up, I could work for Renée in the Boom Boom Lounge for as long as I wanted.

It turns out that not every night is Adult Sissy Night. The theme changed and I would find the other themes equally desirable, based on my psychological profile. I believe they are correct. I’m going back next week and can hardly wait.

My advice to you my gentle reader is that should you hit it big in Vegas, take the recommendation of “Jim G of Terra Haute, Indiana” and “David V of Walla Walla, Washington” and “Allison K of Huntington Beach, California” and take the full sex package. It definitely is worth it.

I now have a gig where I show up and I am transformed into my delicious cross dressing self. I have been a sissy and a maid and a slut. I deliver drinks on a monthly basis to people who don’t know me (once in a while I know them but they don’t seem to tumble.)” I receive little pay but the reality is that I would pay for this opportunity.

Each session is unique. I now shave off all of my body hair to improve my “presentation” as a woman and I have lost 25 lbs (that’s 11.3 kilograms for the metric enabled). I recently had a two hour session with a “Deportment Coach” who taught me how to walk in a more feminine manner (at a rate of $200 per hour, but who is counting). I now have a hobby, walking in heels. I can now walk gracefully in 5 inch heels, but my goal is to walk in 6 inch heels. Interestingly, the pay in the Boom Boom Room increases for a waitress based on the height of the heel.

I solved the problem of hands roaming under my dress. I purchased a stainless steel locking chastity belt. My balls and dick are encased in stainless steel and there is a hinged plate that covers the crack of my ass. While I don’t advertise it, if a man should move his hand under my dress I just relax and smile. He eventually reaches my nether regions and is shocked at what he discovers.

Typically everyone at the table will have a go at it as I am delivering drinks or taking drink orders, and I will invariably receive a good tip. I used to add the belt as I was dressing for my shift. Now I drive from Los Angeles with belt in place. I even leave the belt key at home.

I had an extra key made and this week I’ll be taking it with me. Last week a woman noted the whispers and laughing at the next table and determined that the hand play was the cause. When I delivered her drinks her hand immediately went up my dress and her reaction was somewhat different. She told me that I excited her and that she had to have me.

I explained to her that my “lover” had the key and that I couldn’t release myself.

We made plans to return this weekend. If she is at a table this week she will receive her drink and two keys. One key will be for my room.