The Waitress
Copyright© 2025 by wantsomefun
Chapter 4
Coming of Age Sex Story: Chapter 4 - 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
“You ARE special, Cat. Don’t ever doubt that. Some day a man will tell you how special you are to him.”
“See? There you go, making me blush again! Now, what can I get you?”
“California cheeseburger, medium well done, fries, and an iced tea.”
“With extra lemon. Coming right up.”
She wrote on her pad and hurried away. Her butt really did look nice in that uniform dress. Just like the day before, she kept herself busy. She had two other tables like Marge had said, a young couple who left shortly after I arrived, and two guys dressed like they were on lunch break from an office.
She moved quickly but with grace. I noticed the older businessman looking at her too. We made eye contact, and he mouthed, “Nice ass.” I nodded my guilty agreement and looked away.
Her station was empty by the time I finished my pie. She brought me my bill made out in her neat penmanship.
“Tom? I think I know what that guy said to you.”
I tried to play dumb. “What guy?”
Color flooded her face, and she looked at the floor.
“The bald guy who was sitting right over there. He said I have a nice, ... um, ... butt. And you nodded at him.”
“I’m sorry, Cat.”
“Do guys look at girls’ backsides that much?”
“Do you want the truth? Yes. Men are animals. We look at faces, legs, boobs, butts, and crotches if we can see them.”
Reflexively, her hands covered her groin.
“Suddenly I’m glad I’m wearing an apron.”
“You said you wanted to learn about men, so here’s a fact for you. We look a lot. We try not to get caught. Sometimes we get away with it. Basically, men are pigs, like the guy who grabbed you yesterday. Some simply look and appreciate, like that customer and me. Maybe that makes us more subtle pigs. Anyway, yes, in the real world guys are going to look at your body.”
She raised her big brown eyes to me, a hint of a grin playing in them.
“You’ve been looking at my body a lot, haven’t you?”
Shit. Busted.
“Honestly, Cat, yes. I don’t mean to freak you out, but guys look. If you had gone to public school you’d be used to it by now. I’m not saying it’s right, but it’s true.”
She lowered her voice.
“Sometimes when I go to the mall with my friends we catch guys checking us out. I’m okay with some people looking.”
“I hope that includes me.”
“I wouldn’t have said it otherwise. I look at guys, so I guess it’s only fair they look back.”
“Oh, you look too?”
“Yeah, like when I’m out with my girlfriends. We all do. Sometimes if a guy checks us out long enough we’ll see a bulge in his pants. I kinda like that. Please tell me that’s normal, Tom.”
“Normal and healthy. As long as you don’t leer, most guys would be flattered to know a cute girl like you is admiring them. Relax. No one’s judging you. Just make sure you’re aware of your surroundings. Don’t let yourself get cornered by a strange man. Some people aren’t nice, like those workmen you told me about. Always remember safety.”
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