The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 2

Coming of Age Sex Story: Chapter 2 - An older man, a widower, chance meets a young, virginal girl in a diner. After serving him day after day as his waitress, she finds that she wants to service him sexually and offers her cherry. It's an unlikely love story due to their massive age difference, yet, they find a way to make it work, through tenderness, exploration, and learning from the experienced, older guy.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/ft   Consensual   Romantic   Heterosexual   Fiction   Workplace   First   Masturbation   Oral Sex  

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.”

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