Winning Big in Las Vegas

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.