A New Waitress in Town

THE NEW WAITRESS
Moving to a new community is always difficult, especially when you’re alone, with no friends or relatives to turn to. The advantage though is that you can be anyone you want.

My name is Robin and I recently graduated from a Boston University, where my family has lived since coming to the US from Ireland. I was only two years old when we came here and have no recollection of Ireland at all. I was very settled in Boston, a good school, swimming competitively on the school team, an excellent job as a waiter at an upscale restaurant, girls, you name it. Things were about to change though, as I decided to do post graduate work at a specialized tech collage in Kentucky. It would be a two-year program, which would launch my career in electronic design. I had not carefully considered the change in atmosphere from the big city to a small hick town off the interstate.

The school was stately and old with character. It had a pool which I would make use of as I would swim every day. Classes were to begin in ten days and I had flown in to get an apartment, get a few things, and find a job. I had sold my car in Boston so I could buy one here. Every thing worked out except the job. In Boston there was plenty of good jobs for students. Working as a waiter in a five star restaurant paid for four years of my schooling. But there were no such places here. There were only a couple of fast food joints, a small cafe, and a drug store in this town. Then I heard about the Fifth Wheel. It was a roadhouse at the exit ramp off the expressway. It had a small motel next door and was a haven for truckers passing through. The clerk at student services said the waitresses there did very well, but since they only hired women I was out of luck.

I decided to check the place out. Maybe they had work for men as well? It was early and the place was empty, but what a barn. It was huge. The kitchen was a giant BBQ, for steaks and ribs, the only menu items. There was stage for bands and a big dance floor. A couple of waitresses were getting ready for the late shift, and I couldn’t help but notice how beautiful they were. They were all tall, leggy, with great bodies and long gorgeous hair. The uniforms helped too. They wore black silk western shirts like Johnny Cash, a black leather mini skirt, black stockings, high-heeled boots and a western scarf, like sexy outlaws. I bet they hauled in great tips.

One of the waitresses asked me if needed anything, so I inquired about the job opening they advertised. She said there were no openings in the kitchen, or for bus boys, but the boss has been looking for a new girl to wait tables for a while. That left me out. She said most girls were either intimidated about their looks, didn’t like the uniform, or were too squeamish of the boss. She did mention that he was a pig and that any self-respecting girl would never work for him. She got back to work when he entered the room. He was about forty, tough looking, with a couple of scars on his face, gray hair in a brush cut, smoked a cigar, but wore an expensive looking suit without a tie. I left feeling vanquished.

Back in Boston I gathered the last of my things. My family was watching Mrs. Doubtfire on the television when it dawned on me. I had done some acting in high school. I stood in front of a mirror and did a quick assessment. I was very slim, one hundred twenty-five pounds, from running and long distance swimming, yet my legs looked strong. I have a fair complexion, no hair on my chest, a small nose, but full lips, green eyes, and my blond hair I keep short for swimming. I tried to imagine myself as a woman. To think of it I was never the brutish masculine type at all.

Later that night when everyone was asleep, I put on my sisters dress, pantyhose and bra. I stuffed the bra, and donned an old wig off my moms. I applied makeup from sister’s kit in the bathroom. Once more I stood before the mirror and I liked what I saw. It needed work but it could be done. The next morning I did some shopping downtown in the gay district. I bought some special items like panties which conceal the obvious, custom high heels, and a magnificent redhead wig. The wig actually gets glued to the skin to stay in place and look more realistic. I also picked out a sexy dress for the interview. One stop at a lingerie store and another at the drug store for makeup and I was set.

I needed an extra suitcase to fly back to Kentucky. The two big problems I would face now were my adams apple and my voice. Although mine doesn’t stand out that much, any adams apples show a little. Since the waitresses wore western scarves around their necks, mine would be hidden, so I decided to where one for the interview too. My voice is far from deep, but trying to squeak up an octave all the time would be real tough. That’s were Mrs. Doubtfire reminded me about the accent. The accent threw everyone. Since I was well practiced mocking my mother all my life, I was able to do a pretty mean impression of an Irish woman. I figured since my birth certificate states I was born in Ireland that it would be believable. My name is gender neutral so I wouldn’t need to fake one. It seemed to be working out.

Once in Kentucky, I finished moving into my new apartment, bought a car, and went to check the Fifth Wheel. The job was still available and school was five days away. I immediately practiced walking about the apartment in the high heels. They were tough getting used to. I did my makeup several times for practice. With false eyelashes, mascara, lipstick, the works, it took over an hour to put on.

Finally the day of reckoning came. I was nervous but remembered to be confident like my old drama teacher had taught. I used to shave my body hair for swim meets so this was not new to me. I clean shaved my armpits, legs, even my crotch, for full effect. Then I carefully shaved my face very close taking my sideburns away too. I covered myself with body lotion, powder, and a hit of perfume. I applied my false fingernails, my wig and did my makeup. I put on a black pushup bra over my foam tits which I had placed silicon inserts in. They gave me a nice 36C bust. I also wore a small corset, not that I needed to be thinner but it gave my hips a feminine flair. The black panties forced my dick up in the crotch so no bulges would show. I then rolled on black, seemed stockings attaching them to my garters on the corset. I picked out the black and white gingham two-piece dress. I wore a white blouse under the tight waistcoat and pulled up the skin tight, mid thigh skirt. I put my high heels and a scarf on and viola, instant babe. I did look great, no shit! My ass looked exceptionally round and squeezable with the help of the corset and high heels.

My backdoor goes out to the parking lot, so I snuck out to my car. At the Fifth Wheel I confidently strutted in, turning lots of heads, hopefully for the right reasons. The waitress who greeted me was the same one I spoke with the week before. She showed no signs of recognizing me or of catching my act.