What happens if you apply for a waiter's position and all they have are waitress uniforms?


by Barbara Lynn Terry


There was an ad in the paper for waitress/waiter. I answered the ad and filled out an application. The woman who took my application was about my age, 25, with flaming red hair, Irish green eyes, flawless face and makeup and a figure that just wouldn't quit. when I saw her I thought this wouldn't be a bad place to work after all. Her name was Megan, and she was the owner's daughter.

After I filled out the application, I took it to the cashier, who said have a seat in the corner booth and Megan would be right with me. She brought me a complimentary cup of coffee, and I sat there for what must have been twenty minutes or so. Finally, Megan came and sat down with me, my application in her hand.

"Hi," she said and then looked at my application, "uhm Jaime, is it? I'm Megan Miller. My mother owns the restaurant, but I manage it for her. I see you have applied for the waiter position. Why do you want to wait tables?"

"Well, I'm just out of school, with a BA in sociology...I want to be a social worker. I thought maybe this would give me working experience with the public, while I look for a social work position."

"I see. Well, that is a very good answer. But, I'm not sure you would like the pay, though. You see, we pay three dollars an hour plus any tips you may receive. Do you still want the positon? It isn't going to be easy. When we have our lunch rush during the week you are going to be very busy hopping from one table and booth in your section to another. You may not even have time for a cup of coffee, until you leave for the day.

"Yes ma'am, I would like to take the positon."

She smiled at me and then said, "Good, I thought you would say that. I see also, that you didn't put down the sizes in the uniform section. Why is that?"

"Well, to be truthful, I really don't know my sizes. My mother buys all of my clothes and all I know is they fit." We both giggled at that.

"All right Jaime, come with me and we'll take your measurements in the locker room. Uhm, there is just one thing, our locker room is where the waitresses change. You don't mind being in there, do you?"

I thought that would be seventh heaven so I said no, and we went to the locker room.

"Jaime, you are how tall, five feet, five inches?"


"Okay then, lets get your waist measured." She put the tape measure around my waist and it is 28 inches. Next she meausred my chest and it is 32 inches. Then she did something unexpected. She measured my hips.

"Uhm, Megan? Why did you measure around my butt?"

"Oh! I'm sorry, force of habit. I'm so used to women working here, I just kind of did it out of habit."

"Oh, okay."

"So Jaime, when can you start. We have uniforms here but they are waitress uniforms and I don't think you want to be dressed like a woman, now do you?"

I kind of hesitated at that for a moment, cause ever since I was little, I had been crossdressing here and there. So, when I didn't answer right away, she looked at me very closely. My eyes were very wide and clear, my lashes long, my face very oval in shape and my voice wasn't that deep. In fact, I could be very well mistaken for a natural female, when I was dressed like one.

"Oh my god, Jaime!" She exclaimed. "I just saw you for the first time, and I can see that you are very feminine in appearance, even dressed the way you are! And your name is spelled in the feminine too! Tell you what sweetie, let's get you a uniform and see what you look like, okay?"

I said okay and she went to a cabinet that contained skirts and blouses. Uhm yes, they furnished the uniforms right away if you were a woman, men had to wait two weeks for theirs. She asked me to take off my pants and shirt, and I did. I was wearing a pair of white satin lace panties, with regular nylon stockings, something she had not noticed before. She stood there looking at me with one finger on her chin.

"Hmmmm, nylons, panties, no leg or body hair and no bra either. Hmmmm, did you know we are the same chest size, Jaime? I have a bra you can have, but I suggest you get your own. If you want I could go shopping with you tomorrow."

"Uhm okay, I will accept your present of the bra, but you don't have to bother to go out of your way to go shopping with me."

"It isn't a bother, girlfriend. If you're going to be one of my waitresses, I want to see you get off on the right foot. And besides, we are just one happy family here. Now listen though. We have three waiters on staff and they are all gay. You're not gay are you, Jaime?"

"No ma'am, I'm not. I have always wanted to be a female ever since I was very young, but I haven't had the opportunity to do anyting about it. My reason for wanting to take this job, was so I could start earning money to start my transitional period into becoming female."

"Well, I am not disappointed. You speak very nicely, you look very feminine, and with the right clothes, I can assure you, you will make a fine woman. Have you told your mother yet, about your wish to be female?"

"No, I'm actually kind of scared to tell her. I don't know how she would take it."

"Do you mind if I kind of break the ice for you? I mean, I can explain things to her, a little, so when you tell her, it won't be quite a shock?"

"No, I don't mind at all. It will give me time to..." I trailed off before I could finish. It suddenly hit me that Megan was going out of her way already for me and I needed to know why.

"Uhm Megan? Why are you doing this? I mean, here you are ready to accept me as one of the girls and you don't even really know me. Why are you doing this?"

"If I tell you, will you keep it just between you and me. I mean tell no one about this, not even the other staff members. Okay???"

I looked at her very puzzled, but I said "Okay."

"When I was just seven years old, I liked to play with dolls, dress in pretty clothes, and have my hair very long so it could be styled like all the other girls. My name then was Michael. My mother raised me as a girl and I have had so much fun being Megan, my mother went and got my name and gender changed. Then, during the summer before I was to start high school, I had my surgeries completed. I am now female in all respects. Yes Jaime, I am a transsexual and I love being Megan. No one, except you and my mother know of this here, so don't tell a soul. Okay?"

"Wow! Uhm .... Okay then. I won't tell anyone and to prove it let's pinky swear."

"You are a girl, aren't you?!? Yes, let's pinky swear. Girlfriend, we are going to get along just fine."

Chapter 2 - Telling Mom

I went home that night, and right into my room so my mother wouldn't see my new uniform and get the wrong idea. I tried my uniform on again, just to see what it would look like on me to others. I wasn't exactly going to win Miss America, but I was cute. Tonight I would have to do my hair up really nice and get up early enough to put my makeup on. Then the phone rang.

"Jaime dear, it's for you. A girl."

That's my mom. Always wanting me to get married. Well mother dear, I will get married to a very nice man, after I become the woman I need to be.

I went into the living room and answered the phone. It was Megan.

"Jaime, I just thought that maybe I would come over tomorrow. I talked to mom after you left and she said what I was planning about talking to your mom was a good idea. So, tomorrow being Saturday, I figured I would come over and we could talk and then the three of us could go shopping. Your mom doesn't have to work tomorrow, does she?"

"Uhm no Megan, she is off tomorrow."

"Good. So girlfriend, sleep in tomorrow and I'll be there around lunch time. Okay? Oh! and Jaime? When I come over tomorrow, I want to see you in your uniform and how you will look when you are working. Okay?"

"Okay Megan, no prob."

"See ya tomorrow then, sweetie. Goodnight."

"Goodnight, Megan."

We each hng up and I thought for a while. I will be working as a waitress for a girl my age and a transsexual. That actually makes her one of my peers and I thought that is a good thing. My mother came in the living room.

"She sounds very sweet, dear. Are you going out with this young lady, Jaime?"

"Well mom, I...I...well, I just..."

"Jaime girl, I know. I've known for quite some time now. When you applied for that position at the restaurant, it was as a waitress. Wasn't it dear?"

I looked at her with surprise and shock. My mouth was really wide open and would have hit the floor if it wasn't attached to my jaw.

"Oh honey. I know you're not a man, no matter how you're packaged. See dear, women come in many shapes, sizes and packages. Not to mention that you are very feminine looking, you take after me, and your name is Jaime Lynn so everything is already set for you to be the girl you should have been at birth. What time is she coming over tomorrow?"

"She's coming for lunch, mom. Mom? She is the restaurant manager. Her mother owns it, but she manages it. And she is coming over to talk to you about my position and kind of break the ice. But, you've already done that. Haven't you, mom?"

"Yes dear, quite. Now, go and let me see your new uniform that you were in such a rush to hide from me." That's my mom, nothing gets by her too easily.

So, I went back to my room and got out of my clothes, took a shower, patted down with a soft terry towel, put some lotion on my legs, body, and arms, powdered that down and went to get dressed. I put on the bra that Megan gave me, a pair of off white satin lace panties, rolled my stockings up my legs, I don't wear pantyhose, and put on a white satin lace half slip. Then I sat in front of the mirror and put my makeup on. First I exfoliated my pores, then I put on a light foundation until it blended with my skin, then I put on a light powder. For my eyes I used a blend of natural colors so my baby blues would stand out. I used a waterproof black mascara for my lashes and a light pink lip color. After I put my hair in a really nice pony tail, I went back in the living room. My mother was waiting patiently for my entrance. (Giggle).

"Oh dear!" She exclaimed when she saw me. "And you did this all by yourself? My god Jaime, how long have you been a girl?"

"All of my life mother. This is how I will look when I am working. Megan, that's her name, wants us three to go shopping tomorrow for new clothes for me. Mom? Would it be alright if I gave all my guy clothes to the second hand store? I mean I won't be using them any more and they are still very good."

"Yes dear, you may. And I think it is wonderful that you have found someone who is accepting of you as a girl. I also think it is a very good idea that we go shopping. But, you will pick out your own clothes though dear, as I am just a tad out of touch with young fashions."

We giggled at that, and we went into the kitchen to prepare dinner. For the first time in my 25 years, I was now able to bond with my mother as a daughter and it felt great. Oh! Right! My uniform. Well It is a black skirt with a sewn on frilly white apron, the blouse was red with ruffles, and the shoes were red two inch pumps with an ankle strap.

"Jaime? I just want you to know that I am glad you are able to be the girl you are, without being embarrassed, especially in front of me. I want you to know, I'm very proud of my daughter."

"Thanks mom. That means a lot to me."

"I know dear. Now, get out the chicken breasts and the bouillon cubes. We are having a fat free dinner tonight."

"Sounds great mom. Are we having a salad with the chicken?"

"Yes dear, we are."

"Can I make the salad, mom?"

"Why of course, dear," she said with a beaming smile.

I was enjoying this. My mother accepted me as her daughter without the slightest hesitation and it felt really great. Oh! I almost forgot. My full name is Jaime Lynn McConoughy. And today is the first day of the rest of my life ... as a girl...woman...female. When dinner was ready, we sat down to a nice meal and we talked some.

"Jaime, I have been watching you. I don't need to teach you anything about being a girl. You seem very feminine in the way you smooth out your skirt as you gently sit down with your legs together and your back very straight. And look how you take small bites instead of gulping your food. That is very ladylike. I'm going to enjoy having my daughter."

"Thanks mom. I'm going to enjoy being your daughter too. I'm still going to look for a social work position though. I don't want to be a waitress all of my life (giggle)."

"Yes dear. But waitressing can give you experience with the public and you will have some customers that will tell you their problems uninvited. Waitresses, bartenders and cab drivers should all have a sociology degrees the way they listen to others problems and sometimes offer advice. You graduated with honors from high school, and you graduated in the top ten of your college class. I'm am very proud of my daughter. And you should be very proud of yourself too, girl."

"Thanks mom, you're the greatest."

Chapter 3 - Megan comes to lunch

After dinner was over and we cleaned the dishes and the rest of the kitchen together, I gave mom a kiss and a hug and told her I was getting an early to bed as tomorrow would be a very busy day.

"Goodnight swetheart, sleep well and sweet dreams."

"Goodnight mother, you too."

I slept very well that night, dreaming I was walking down the aisle to be wed to my new husband. He was handsome, tall and all muscle. I couldn't see a face though,as I don't know who he may be, but that is my dream man and I will meet him one day. I woke up to my alarm clock, opened my eyes and stretched. I swung both legs out of bed so my feet would hit the floor together. I sauntered into the bathroom and ran my bath. No shower today. I wanted a bubble bath. I took out some lavender crystal and put them in the tub. They bubbled up very nicely. I gingerly stepped into the tub and took a soft terry wash cloth and just ran the water over me by squeezing the cloth. Oh my god! the sensations I was feeling. I then sat there soaking up the suds until I started looking like a prune (giggle). I drained the tub and ran the shower to rinse the rest of the suds off. I patted down with a soft terry towel and wrapped it around me the way women do. I went to my dresser and got out my under clothes, my uniform and my uniform pumps. I laid everything out on the bed and went to put on my makeup. I wear natural or very light colors, so that I look natural and I went through the same routine as I did the night before. Since I had been wearing makeup for years, even in high school with some of my girl friends, it didn't take me long at all to complete a very natural look. Makeup should enhance a woman's beauty not camouflage it. After I was dressed I looked at myself from all angles to make sure everything was perfect. It was. I then went down to make breakfast.

I took out a pack of breakfast rolls, a package of lean bacon, and the eggs. I took a cookie sheet and put some margarine on it so the rolls wouldn't stick, set the oven for three hundred and fifty degrees. I put the bacon on a table top electric grill so the fat, what there was of it, would drip off. Just as I was ready to start the eggs, mom came in and I poured her a cup of coffee. We have a coffee maker that you can set te night before, so it is ready by the time you wake up.

"Why Jaime! Thank you so much for making breakfast. I was going to get up and make breakfast for you in honor of my daughter. But you beat me to it (smile)."

"Yes mom, I thought I would do something for you today, cause you did something for me last night."

"Oh? And what was that, dear?"

"You accepted me as your daughter without any hesitation. This is my way of saying thank you."

"You are a sweet girl, Jaime, and I love you dearly." She then gave me a hug and kiss. And just look at you today! You wouldn't have an important date today, would you?"

"Yes mom, I do. I'm going shopping with my bestest friend in all the world and a new friend I met yesterday. Today is a very important day in my life and I have you and Megan to thank for it."

"Oh dear! Think nothing of it. You are my daughter, you always have been in more ways than you know. I'm only glad I have her now."

"Thanks Mom, you're the greatest."

Breakfast finished, we cleaned up the kitchen again together and went in the front room. It would be a few hours before Megan got here, so we had time to bond a little more. Just then the doorbell rang.

"I'll get it mom. I wonder who that could be so early?"

I opened the door and to my surprise, it was Megan.

"Megan!" I exclaimed and gave her a big hug and sisterly kiss. "What are you doing here so early?"

"I wanted to see how my new sister was dressed today and you did not disappoint me. I see you already told your mom."

"Well girlfriend, she actually told me. We have had a very nice time though, doing things around the house as mother and daughter. Come in! I want you meet the bestest friend a girl could ever have."

"Mom? This is Megan Miller. She manages the Copper Kettle over on Main Street."

Holding out her hand, my mother walked toward Megan. "I'm Estelle, Essie to my friends."

Megan hugged my mom and we sat down for a little chat.

"Megan would you like a cup of coffee and a roll?"

"Just coffee, I've already had breakfast. Thank you."

"Jaime made breakfast this morning. She did a wonderful job of it too. So Meagan, Jaime tells me you manage the restaurant for your mother. How long have you been doing that?"

"I've been managing for a little over three years now, but I have always helped out in the restaurant even when I was a little girl. I kind of grew up in that place. When my dad passed away of heart failure, my mom wanted to sell the restaurant, but I talked her into keeping it. She doesn't take an active part in it anymore, cause it brings back too many painful memories for her. So I run it for her."

"That's great dear. But tell me. How did you happen to guess that Jaime wasn't what she seemed at first?"

"Essie, if I tell you, will you keep just between us three? I mean, not that I'm ashamed or anything like that. It's just that the less people know the less problems I have."

"Why of course, dear. Anything said here stays here."

"Good. Well I told Jaime yesterday about me and she swore to take it to the grave. We even pinky swore on it too. Well Essie, I have not always been female. My name when I was younger was Michael. I loved to play with dolls, wear dresses be, one of the girls and so on. So my mother raised me as a girl from the age of seven, and just before I was to go into high school I had all of my surgeries completed. My full name is Megan Marie Miller. I recognized the same traits in Jaime yesterday that I saw in myself years ago."

"You Know Megan," my mom interjected. "I asked Jaime last night how long she had been a girl cause when she came down to help me with dinner she was impeccably made up and I told her I wanted to see her uniform. So she tells me she has been a girl all of her life. She's a good girl, Megan. A daughter any mother would be proud to have."

"You did that makeup yourself, Jaime?!? Oh my god! You look really beautiful!"

"Thanks Megan. Thanks mom. I have a very important date today with two of the most beautiful women in the world and they are both my bestest friends." I gave mom and Megan each a kiss and hug. "Sooooo, we have a few hours before lunch. Why don't we all go shopping and get it started anyway. I want to make a day of it cause I have so much to get. I also called yesterday too and made a last minute appointment to get my hair really done up pretty like. (Giggle) I did that when I left the restaurant. Then I was thinking we could have lunch at a little out of the way place on Main Street called the Copper Kettle. Ever hear of it? (Giggle)."

"Copper Kettle hey? Nope, never heard of it (giggle)," Megan joked.

"All right girls, if we're ready to go we should start now then. Today Jaime becomes a woman for the rest of her life."

I said thank you to mom again for those nice compliments she has been showering me with since yesterday, grabbed a purse I had hidden in my room, but will be hidden no more, and out the door we went. Three women out on the town on a nice summer Saturday.


Readers, Please Remember to Leave a Comment

Want to comment but don't want to open an account?
Anyone can log in as Guest Reader -- password topshelf to leave a comment.


If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
62 users have voted.

And please, remember to comment, too! Thanks. 
This story is 4041 words long.