The Waitress

by wantsomefun

©Copyright 2017 wantsomefun

NOTE: I ran into wantsomefun at an erotic stories forum, and we hit it off from the start because I made friends with a classy lady there, a friend of his, ejls. Over the next five years, we had our share of laughs and triumphs and our fights too. He was a very good writer, a great conversationalist, funny, and rather intelligent. At one point, in early 2017, the three of us got pissed at the state of affairs at that site, and made a decision to leave and start a new site, one that would be, above all, devoid of trolls. And that's exactly what we did, and today, it is still running strong. Unfortunately, one month after the site opened, wantsomefun (Rich was his name) passed unexpectedly. It was a huge, huge blow to the website, and to those who knew him. As per the terms of the website that he helped create, we're publishing his stories, and we know that he is smiling down upon us. --ahorsewithnoname

Chapter 1

Now that I'm retired, every day is like the first day of a week off work. I'm not ready for a rocking chair, so I run around a lot, something I couldn't do on weekdays except in summer my entire adult life. My late wife and I used to go out for lunch most weekends at the local diner where I took her on our first date. It's an aluminum-clad monument to mid-twentieth century commercial architecture.

They've expanded the place over the decades, but the metal facade still gleams. The curb service girls with poodle skirts and roller skates are long gone, as well as the ninety-nine cent burger basket and shakes for two special and the 45 rpm jukebox, but in some ways the place hasn't changed since I was a little kid.

Their prices are the lowest around, the food is good, and they've always had the best apple pie in town. With no damn schedule anymore, I decided it might be my regular noon spot.

I went in the first Monday of my freedom. Kids were out of school for the year, and many families were away on vacation, so the diner wasn't busy. The hostess, Marge, led me to a small table in an empty part of the restaurant. “Will you be the guinea pig for a new girl, Tom?”

“Sure. You know me. I don't bite. All I plan to do this afternoon is housework. If she's slow it won't matter.”

Soon a petite brunette with her hair in a short ponytail came to my table. Her name tag said Catherine, and under it she wore a “trainee” pin. She filled my water glass and handed me a menu. When we made eye contact she blushed and looked at the floor, but she soldiered on.

“Hi! This is my first day. The boss has been training me all morning, and she said you're a regular, so she sent me over here solo. You're the first customer I'm waiting on alone. I promise I won't mess up.”

“I'll take it easy on you, Catherine.”

“How did you know my name?”

I pointed at the plastic tag pinned to her uniform above her heart.

“Oh, right. I guess you figured out I'm new then, too. I feel silly now.” More blushing.

“Don't feel silly. Marge was right sending you to me for your maiden voyage. I'm Tom - a regular customer who's pretty easy to please. I retired last week after teaching high school math for thirty-five years. Most of the employees here had me for geometry class, but I don't remember you.”

“I go to St. Bernadette's Academy.”

“That's still an all girls' school, isn't it?”

She wrinkled her pert nose in disgust. “Unfortunately. There was talk a few years ago about a merger with St. Samuel's Prep, the boys' school, but the diocese shot it down.”

“So, no guys around, huh?”

“The only men on campus are the priests and some maintenance staff. That's one of the reasons I wanted this job - so I'd learn to talk to guys in the real world before I head off to college.”

“This is a pretty non-threatening environment. You're in a structured setting with a job to do and a role to play that everyone understands. You'll see all kinds of men here. Most will be nice. If they're not, Large Marge will throw them out.”

She looked a little shocked that I used that nickname, but after a quick check to make sure the boss hadn't heard, she giggled.

“The only guys I see are my dad and my one older brother who still lives at home. I'll be a senior next year, and I just turned eighteen, but I don't have a car, and I don't have any money to spend running around. I couldn't face being cooped up in that house for another summer. I begged enough that my parents FINALLY let me get a job. I'll probably work part time next school year too. I need to save money for college, and it gets me out of the house.”

“Your folks are strict?”

“They're old-school Catholics. I'm the youngest of five kids and the only daughter, so they're super protective. I'm a legal adult, for pity's sake. I could buy lottery tickets or sign a lease or even join the armed services, but I'm kinda stuck at home.

"I'm, like, the only girl in my class who isn't allowed to go on solo dates, and my brothers intimidate anyone who might ask. I don't even bring my girlfriends to the house much. My parents have to listen in on everything, and my brother Charlie is kinda weird.”

“A job outside the home will do you wonders, then. Other employees tell me this is a nice place to work. If you take care of your customers, they'll request your station and give you good tips.”

“That's what Marge said. It's my first job, so it's all kinda new to me, ya know?”

“Be polite to people, write legibly so the kitchen staff can read your orders, and check what they give you before you serve it to make sure everything is right. Sooner or later you'll get customers who seem to be out to ruin your day.

"Some people try to make everyone as miserable as they are. Rise above them - do your job, smile when they give you a lousy tip, and go on with your day. Most people are nice if you're nice to them. I'm sure you'll do fine. Now, a pop quiz for you. What's today's special?”

“Oh, I'm sorry,” she blushed yet again. “I was supposed to tell you that right away.”

“After greeting me, which you did. Calm down. You don't have any other customers, and I'm not in a rush. Do you know the special? No cheating and looking at the note inside the menu, either.”

“Marge had me clip the notes on so I could memorize it.”

Chapter 2

She stood up a little straighter like she was preparing to recite in a formal classroom and took a deep breath.

“Sir, today's five dollar lunch special is a cup of our famous homemade chicken vegetable soup, along with a grilled ham and cheese sandwich, french fries, a pickle spear, and a medium soda or iced tea. Sir.”

“One 'sir' is more than enough, Catherine. Besides, I prefer Tom. Pop quiz question number two: who are your french fry and pickle vendors?”

“Vendors?”

“What companies supply the diner with french fries and pickles?”

“Oh! They don't have vendors for those things. They get everything - fresh produce, cheeses, meats, you name it - from the farmers' market. Even the pickles come from a stand there, but they use the diner's recipe. The only things they serve that are, like, name brand ready-made are potato chips and ice cream. And of course soft drinks.”

“Good girl. The same as it's been for over fifty years. Did Marge teach you that?”

“Yes. I've been here almost four hours, and the first two were in the kitchen learning about how they make the food. I'm taking a copy of the menu home to study tonight.”

“Oh? You'll make a good employee. Now, I'll have the special and an iced tea with extra lemon.”

She wrote quickly on her pad. “Thank you! I'll be right back with your beverage.” She scurried away.

Waitresses here wear vintage style uniform dresses, white, with the skirt hemmed just above the knee, red gingham trim, and a matching half apron with pockets for their order pad and pens. Catherine's dress fit loosely enough to give her freedom of movement and to be modest, but not so loosely it hid her shape, especially with the apron tied around her waist. Her hips moved fluidly as she walked - nothing intentionally seductive, but graceful and light on her feet.

True to her word, she was back in a moment with my iced tea and a small bowl of lemon slices. “Here you are, sir.”

“I'm sure Marge said you should call everyone Miss, Madam, or Sir, but I told you my name. Now that I'm retired, I like hearing Tom instead of Sir or Mr. Cooper.”

“Isn't that, like, too familiar?”

“Not for me. You'll probably see me in here a lot, so just call me Tom like my other friends do.”

Warm color flooded her fair cheeks.

“Thank you. Marge said you were nice. My parents and the nuns call me Catherine. Everyone else calls me Cat. Let me check on that soup. They're making a fresh batch. I'll be right back.”

She returned a minute later with a steaming cup, as much chunks of tender chicken and crisp veggies as broth.

“You should wait a bit. This is boiling hot.”

“As it should be when it's freshly made. This is the only place I've ever had soup like this. There's a mix of seasonings here I can't identify. My late wife used to hound Marge for the recipe, but she said it was a secret.”

“It is,” Cat said. “I actually had to sign a paper saying I wouldn't tell the ingredients before I could start work.”

“I was a child when the diner first opened. They sold burgers, hot dogs, french fries, and this soup. My parents brought me here on Saturday nights for burgers and took soup home to re-heat after church.”

“My folks did the same thing when I was younger. They'd bring my brothers and me here for dinner on Saturday after a matinee movie or miniature golf, and they'd take containers of soup home to serve on Sunday after Mass. I should go check on your sandwich. Do you want another iced tea?”

“Not yet. Is there any apple pie back there?”

She grinned. “There certainly is. Best in town, just like the sign outside says. There were six pies in the oven when I came in this morning. I just wanted to stand there and inhale.”

“I'll have a slice of apple pie later with my second glass of tea.”

She noted it on her pad and went back to the kitchen. A short time later, she returned with my meal. “Is this correct, sir … I mean, Tom?”

“It is. Thank you.”

“I'll be back to check on you in a few minutes.”

“No hurry. That soup was delicious. I could probably eat it every day and not get tired of it.”

“I know, right? I'm going to have some on my break.”

She grinned and went back to the counter to wrap paper napkins around place settings of flatware for later use. Every time I looked up from my plate she was busy, but she kept glancing at me. Just before I finished with my meal she came back.

“Do you still want that apple pie?”

“You didn't eat all of it, did you?”

“No!”

“I didn't think so. I don't know where you'd put it.”

She blushed yet again and smoothed her uniform dress over her mid-section. “I'm not THAT skinny!”

“Not skinny, Cat. Petite. How tall are you?”

“Five foot four.”

“What do you weigh? A hundred pounds?”

“You're not supposed to ask a girl that.”

“I guess you're right. It's not something a gentleman asks a young lady.”

Her face was the color of the red gingham trim on her uniform. Barely above a whisper she said, “My brother Charlie teases me about not having curves. Some of the girls in school do too. I hate gym class. Some of those girls are built like centerfolds. Most of the others are at least tall. To answer your question, I can't seem to get over a hundred and three pounds.”

“It's a good weight for you. Turn around slowly.”

“What? Why?”

“I want to look at you.”

Chapter 3

She glanced around the room to make sure no one was paying attention to us and then turned for my inspection. When she faced me again, her cheeks were so red they looked like they hurt.

“I can see why your family is nervous about boys.”

“What do you mean?”

“You're an attractive young woman, Cat. And stop blushing.”

“I can't help it. No one ever complimented me on my appearance before.”

“Maybe this job will boost your self-confidence. Stand up straight, pull your shoulders back, open those pretty brown eyes wide, and smile.”

She did, squaring her shoulders, sucking in her soft little belly, and lifting her chin, which helped to display her petite breasts. “Like this?”

“Yes, exactly. You look taller that way. Your posture now says you're alert and eager to please your customers.”

She smiled broadly this time.

“Thanks, Tom. Do you want whipped cream on your pie? It's the real thing, not that canned spray goop from the supermarket.”

“I know they don't use that crap here. Yes, just a little whipped cream.”

“And your iced tea with extra lemon.”

She cleared the table, grinning the whole time, and walked smartly back to the kitchen.

I was done with my pie and sipping on my iced tea when she brought my check.

“You can pay the cashier, or I can take it for you.”

I pulled a twenty out of my wallet and gave it to her. She took the slip and the money to the register and returned with my change.

“Keep it,” I said.

“Tom, even with the pie and second iced tea your bill was less than ten dollars. I can't keep all this.”

“Yes you can. You spent a lot of time waiting on me, and you did a perfect job. You won't earn much in tips until you have a full station. This may be about it for today. You're a good kid, Cat. Take it.”

Barely above a whisper she said, “Thanks.”

“When do you work next?”

“I'm scheduled eight to four today through Thursday and again on Saturday.”

“I'm a widower who hates to cook. I was never much of a breakfast person, so I usually don't eat until lunch. By then I'm pretty hungry. I come in here all the time, so you'll see me a lot. I'll ask for your station. Consider me your first regular.”

“I look forward to waiting on you again, Tom.”

Marge caught me on my way out the door.

“What did you do to that girl?”

“Excuse me?”

“Catherine is walking on the clouds. She's in the kitchen humming with a silly grin on her face.”

“Ah. I gave her some advice on being a waitress people would request again, and I gave her a big tip.”

Marge nodded.

“She's a fast learner, and she seems like a nice girl, but she's shy. I think you made her day.”

“She chatted well enough with me after I got her going. I gather she's pretty sheltered at home, so I tried to make her feel comfortable. When I was in college I was a waiter in a busy Italian family-type restaurant. I know how hard this job is. She said she's working this time again tomorrow?”