Alone first

Boruto chuckled to himself and pulled Shizune into an alleyway where they wouldn't be disturbed. His first order of business was getting a look at her body.

She was clad in her typical black kimono which did her figure no favors. As he pulled it open, he realized her tits were bigger and hips were wider than he assumed.

"From now on, I want you to wear clothes that better suit your figure" he said plainly

"Yes Master" she droned in reply.

He began running his hands over her body. The moment his finger touched her pussy through her panties, she shivered, even in her trance.

"Woah. You're really sensitive. When was the last time you had sex huh?" He asked jokingly, not expecting a reply. However, in this state Shizune couldn't comprehend the concept of a joke.

"Almost 20 years ago" she replied blankly.

"Wait WHAT?! A hottie like you?! When was your last boyfriend?!"

"Never" she replied in a matter of fact tone.

Boruto was, frankly, flabbergasted.

"Man. I bet you're desperate to cum, huh?"

"Yes Master" she answered.