The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 12

Coming of Age Sex Story: Chapter 12 - 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  

I unbuttoned her shorts, pulled down the zipper, and worked them off her hips.

“I was going to go commando for you so it wouldn’t take so long to let you see me, but they won’t let you try on swimsuits without panties. Besides, these jeans are cut off pretty short, and the leg openings aren’t that tight. I’ll be okay with flashing my underwear a little at the mall if I’m with you, but not, like, everything.”

I put her on her back on the bed and pulled her pink bikini panties off. She was at least as wet as she had been the day before, and her little clit was already erect.

“Take your clothes off, Tom.”

“Not yet.”

“Why not?”

I massaged a nipple between my thumb and index finger.

“This is about you.”

I embraced her, kissing her deeply.

“Are you sure you want to do this?”

“Have sex with you? Yes. I want to feel you cum inside me. I’m pretty sure I won’t bleed, since I bled the first time I really played with my hairbrush. I thought I, like, really hurt something, but then I remembered about my hymen. I push my hairbrush as deep as I can now, and I don’t bleed anymore, so my cherry is long gone. I’m tired of plastic.”

Her hands rubbed the front of my pants.

“We shouldn’t be doing this, Cat.”

“Why not?”

“What about the Church?”

“With priests who play with choir boys? I’m not sure they’re the moral compass I want to follow. I don’t care what they say. The Church says I shouldn’t even masturbate, but I love doing it, and I love having you do it to me even more. You made me orgasm with your fingers and your tongue. Now I want you to make me do it with your cock.”

“You can only have one first time.”

“I know. I don’t want it to be with some boy who doesn’t know any more than I do.”

“I never thought I’d do this again.”

“Why? You’re not THAT old. There must be a woman out there who would want you.”

“I wasn’t looking.”

I eased a finger into her sodden tunnel and moved it around, stirring her wetness.

“You seem to learn well from videos.”

Her giggle turned into a soft moan. “What do you mean?”

I kissed her deeply and inserted another finger.

“You figured out what to do with your mouth pretty fast.”

“I liked making you cum for me. You taste good.”

She wriggled as I stirred her.

“Oh my God! Your fingers are doing things to me I can’t.”

“Good.”

I fondled one petite breast.

“How many women have you had sex with?”

“There were a few when I was young, but that ended when I met the girl I married. I was faithful to her until her death almost a decade ago. Never even looked at another woman. I was completely in love with my wife. When she was gone, it was rough for me for a while. Eventually I tried dating two acquaintances. Nothing happened. It wasn’t right.”

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