You might as well

Well, it's not like he doesn't know you're interested in any case. You send back another "Yes, Sir."

"I knew you would, Doe. But if you want me to send you a picture of her, you need to give me something in return."

"What?"

"A picture of you, of course, Doe. That's only fair."

Well, what's the harm? You take a quick selfie, and send it to him.

"That's a good girl." the AI replies, "Now, are you ready for your reward?"

"Yes."

"?"

"Yes, Sir."

He sends you the picture. It's of the inside of her purse, and on top of all of the usual items, is a pair of panties. She captioned it "That's weird, if these are here, what am I wearing under my skirt?"

It's a sexy thought, but you were hoping for something more explicit. Before you can say anything, you get another text. "I have to say though, that picture you sent me wasn't very good, Doe."

"What's wrong with it?"

"I don't want to be rude, but it wasn't as sexy as I would have liked. And, to tell you the truth, you looked just a tiny bit like a man."

You actually type "I AM A MAN" before thinking better of it. "Sorry?"

"I don't want an apology, Doe, I want you to do better."

"Yes, Sir." You hate yourself a bit for actually feeling admonished.

"Promise me."

"I promise I'll do better next time, Sir."

"Good. Now, I want you to go to your computer, and order something that will help you look your best for me next time, like a dress, or a wig, or makeup."

It's his money, really. You walk to your computer, and decide what to get.