The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 3

Coming of Age Sex Story: Chapter 3 - 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 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?”

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