“What’s the weirdest thing you’ve ever masturbated with?”

Samantha bursts our laughing as she looks at your phone.

“What?” you ask, “What’s the question!?”

“Oh my, we can skip this if you don’t want to answer.”

“Just ask me the question.”

Samantha composes herself and with a straight face asks, “What’s the weirdest thing you’ve ever masturbated with?”

“Ah, yeah…” you say. “Okay, give me a second to think.”

“You’ve have a lot of masturbation sessions to think through, I imagine.”

“I’m sure it’s more than you imagine,” you say. “I really wish you had gotten this question, I’m very curious what your answer would be.”

“Well it’s not your lucky day, Mr. Madison. You’ll never know what toys…”

“I’d be more interested in the other objects,” you say cutting her off.

Samantha laughs, “toys or other objects have been inside of me.”

Your cock is throbbing as you imagine a young Samantha exploring her body.

“So what’s your answer? That’s what the world wants to know,” she asks.

“One time, I jerked off… with a cantaloupe,” you admit.

Samantha tries to keep a straight face, but fails. She bursts out laughing and covers her face to try to stifle her laughter. “Sorry! Sorry!”

“It’s okay. I was dating a girl long distance and we’d do things over Skype and one time I jerked off into a hollowed out cantaloupe while she watched.”

“Oh,” Samantha says regaining her composure. It suddenly felt less silly knowing that there was someone watching. She couldn’t help but imagine picturing you with a cantaloupe, and knowing that you were doing it, not in secret, but o display made it pretty sexy. “I guess that’s pretty cool then.”

“Cool?” you say. “What does that mean?!”

“I just mean, there’s a certain vulnerability to like exploring sexuality, so that you were confident enough…” Samantha is brightly blushing. “Uh… kinky enough, I guess. That’s cool.”

“I’m glad my masturbation has your approval, Samantha” you say with mock sincerity and put your hands on her.

“You’re welcome, John,” Samantha says smiling brightly.

“Okay, it’s your turn! You say. Are you ready?”

“Yeah, give me your worse, Book of Questions App!,” Samantha says talking to your phone. “I’m prepared to bare my soul to my boss!”

“Samantha, what was your earliest sexual experience,” you read.