The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 8

Coming of Age Sex Story: Chapter 8 - 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 unbuckled her seat belt and turned to face me. “I got in the shower and pretended you licked me and then put your cock inside me, and you had your hands on my butt the whole time. I took my hairbrush with me and made believe it was your penis. I never got off so fast or so hard. I just kept going.

“I don’t know how many orgasms I had, but I had to sit down before I fell down. All I could think about was your hard cock in your pants and what it would feel like shooting cum inside me. They say a girl can feel a guy go off.”

She looked at the bulge in my pants again.

“Your cock looks bigger than my hairbrush handle. Can I see it?”

“What? No! I can’t show you that!”

“Why not? I want to know if it’s bigger than my brother’s. That’s what I wanted to tell you. There were dirty clothes on the floor around my hamper when I went upstairs last night. I’m kind of a neat freak, so I never do that. Charlie left his door open partway, maybe on purpose. I heard him, like, breathing hard, so I sneaked over to see what was wrong.

“He had the panties I wore all day in his mouth, and he was stroking his cock. I couldn’t see real well, but he had his hand wrapped around it and was rubbing pretty fast. I wanted to watch him cum, but I heard Mom downstairs saying she was ready for bed, so I went back in my room and shut the door. Can I watch you?”

“What? No! I can’t do that! You’re the age of some of my students!”

“But I’m not one of your students. Besides, you’re retired, aren’t you?”

“That’s not the point, Cat.”

She flashed a naughty grin.

“There’s no one here. I’ve seen guys in videos, but not for real. Please? I wanna see.”

Her hand was under her skirt.

“Are you playing with yourself?”

“Uh huh. I’ll show you mine if you show me yours.”

“This isn’t right, Cat.”

“Oh, I know. I’ll have to go to confession, but I don’t care. I want to see you play with your penis.”

“No.”

“I bet I’m, like, the only eighteen year old girl in town who hasn’t seen a real cock.”

She lifted herself in her seat and pulled her panties from under her uniform dress.

“I know you’re going to masturbate when you get home. That’s what I want to do – play with myself, but I don’t want to wait, and I want to watch you stroke your cock while I rub my pussy.”

She reached across the console and fondled me through my clothes.

“Can I touch it? Here, maybe you’ll enjoy smelling my panties like Charlie does.”

She handed me her warm white cotton undergarment and started on my fly.

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