The Waitress - Cover

The Waitress

Copyright© 2025 by wantsomefun

Chapter 14

Coming of Age Sex Story: Chapter 14 - 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 experimented with moving her pelvis to change her pussy’s grip on me.

“If you don’t cum soon I might go again.”

“Is that such a bad thing?”

“How can I make you shoot your cum into me?”

I worked my hand between us to play with the tissues around her clit.

“Just keep doing what you’re doing. Feeling you orgasm again might do it for me.”

“I’m not sure how much more I can take. Please cum for me.”

She moved herself more rapidly on and off me, kissing me wildly and grinding herself onto my cock and fingers.

“You’re getting bigger. You get bigger when you cum.”

“Yes,” I hissed.

“I feel it. I feel it moving. Are you cumming? Oh my God you are I’m all warm and wet inside different than before oh my God!”

Her orgasm’s rhythmic pulses in her vagina drained me completely. We clung together kissing until my spent cock wilted from her.

“I want to do that some more,” she said.

She rolled off and then nuzzled against me.

“I can’t believe we did that.”

My heart sank. “I’m so sorry.”

“No, I mean it in a good way, Tom. I hear stuff my friends say and watch some porn, so I kinda thought I knew what was going to happen. But I can’t believe it actually did, like, I finally not only had sex, but I had good sex. I have no regrets. Do you?”

“Depends on whether you can keep a secret.”

She wiped some of the mess from her pussy with finger and smeared an X above her left nipple.

“Cross my heart.”

We lay side by side for about a half hour, cuddling quietly.

“Tom? When do you want to shower?”

I led her to the bathroom and turned on the water. When the temperature was right, I pulled her under the shower with me. She worked shampoo into her hair. I lathered up a wash cloth and started on her face.

“I never showered with anyone before. Gym showers, yeah, but we don’t touch, and of course I never showered with a guy. This is so hot.”

“Washing each other is in some ways more intimate than sharing a bed. We can see and touch everything in here. Plenty of light.”

“Yeah, you can see how small my boobs really are.”

I cupped water in my hands to rinse the suds off her right nipple and sucked it into my mouth.

“They’re a perfect size for you.”

She reached for my re-awakened cock.

“This is the right size for me too.”

When we were done bathing, I held her close to kiss, grabbing her cute little ass to pull her against me.

She reached between us to stroke my cock.

“Can we have sex in here like I talked about?”

“Hold onto my neck,” I said, and I lifted her so her opening was poised over my erection. “Now, aim me.”

She did, notching me in her opening and then lifting her legs and locking her ankles behind me. We mated that way for quite a while, slowly, deliberately, not saying a word, kissing furiously. Her tight little pussy caressed my manhood as it moved in and out of her. Eventually, the pace of her breathing increased until she was panting and gasping, using her arms to help her move on my shaft as I pumped her.

“Oh God, Tom, I’m gonna cum so hard!”

“Good.”

I thrust upward more forcefully as my orgasm approached, and she fucked me back just as hard. When my spasms dwindled away she was limp, barely able to support herself when I set her down.

We dried off, and I found my late wife’s old hair dryer for her to use. When we returned to the bedroom, she looked at my bedside clock.

“Not sure we really have time to go to the mall this afternoon. I need to get home before Mom does and change clothes so she doesn’t give me grief about going outside dressed like this.”

“Should I take you now?”

“Not yet.”

“Then come to bed.”

We lay there and cuddled until she got drowsy.

“I could lie here naked with you all day,” she yawned.

“I’m sorry we didn’t get to shop for a bathing suit for you.”

“It’s okay. I enjoyed this a lot more. Besides, I feel sexier with you than I would in any bikini. Maybe we can go shopping on Saturday, since I don’t have to work.”

“I’d like that.”

“We can come here first and see if there’s time when we’re done making love,” she said. “I want to do it a lot.”

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