The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 1

Coming of Age Sex Story: Chapter 1 - 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  

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.”

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