The Waitress
Copyright© 2025 by wantsomefun
Chapter 10
Coming of Age Sex Story: Chapter 10 - 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
We rode in silence until she started to giggle. “You know what?”
“What?”
“I’m still soaked. My panties will smell good to Charlie if he steals them tonight. Maybe I should just give them to him.”
“Give them to him?”
“When I get home I’ll take a shower like I always do after work. Instead of putting my panties in the hamper and making him sneak around, I’ll put them on his pillow to find when he gets home.”
“You’re more naughty than I thought.”
“I can’t help it. The idea of a guy masturbating thinking about me makes me wet, even if it is my brother. Thanks to you I suddenly feel pretty and desirable and sexy. I like it. I never thought anyone would see me that way. Ever since I saw you checking me out I’ve been thinking about sex constantly. I liked what we did today.”
“I’m sure you could tell I enjoyed it.”
I pulled into her driveway.
“I want to taste your cum again, Tom. Will I see you tomorrow?”
“At noon.”
She got out of the car and flipped up the back of her skirt.
“Sometime I want you to play with my butt.”
Then she went in the house.
The following day Cat greeted me as though nothing had happened. Her station was busy, so she simply filled my water glass and handed me a menu. She leaned in a little to make sure no one would hear.
“I masturbated until I fell asleep last night, Tom. What can I get you?”
I ordered the day’s special. We barely had time to chat.
When she brought my bill she said, “Mom’s taking me shopping this afternoon, so she’s picking me up when I’m done work. Will you be here tomorrow? I have another story about Charlie.”
Wednesday dawned drizzly and cool. Things didn’t improve during the morning. At lunch time Cat said, “Charlie is definitely picking me up after work tonight. Will you be in tomorrow?”
The following day she greeted me with a big grin.
“I have the day off tomorrow, you know.”
“Right, you said that.”
She blushed and looked around to make sure no one could hear.
“A friend of mine owes me a favor. I want to go shopping again.”
I grinned.
“Girls and their shopping.”
“The favor is she’ll cover for me and say I was with her all day.”
“What did you do for her to make her agree to that?”
“I lied for her when she went to a college party. She was too drunk to go home, so I called her mom and said she was with me. I didn’t ask too many questions, so she won’t either if you want to do something.”
“Do something like what?”
“Well, Mom wouldn’t even let me go in some of the cute shops for a bathing suit. You keep telling me men like looking at girls like me, so why not show off a little?”