I've been texting this HB9 for a bit and I want to sexualize the conversation. Any tips on how to proceed?

Why not try some kino escalation? Where are we going on vacation will all of our loot? We could go to St. Marteen but I gotta warn you they go topless, a bit racy, but you know your audience better.

Or you could be more tame. Since pretty girls never get in trouble robbing banks what's your secret, what outfit just neutralizes the guard? Is it the thong or lingerie?

Some girls just aren't into it. It's almost always better to have a flirty non-sexual conversation than to force sex into the conversation and make her think too much. You want to trigger her emotions, not her brain.

I've always found that the best route to sexual flirting is non-sexual flirting. (The biggest mistake guys make, myself included, is trying to get to sexual flirting from a non-flirtatious sexual topic of conversation. Again, focus on emotional flow, not logical flow.)

Non-sexual flirting. You have it. Role play. Joking around. But you're missing the push pull.

WRONG WAY: Push-Push-Push
You: Pretty girls never get in trouble.
Her: Aww, thank you!
You: Know how to drive stick?
Her: Yeah. I drive a volkswagon.

WRONG WAY: Over-Compensating
You: Pretty girls never get in trouble.
Her: Aww, thank you!
You: Shut up you ugly bitch!
Her: WTF?

RIGHT WAY:
You: Pretty girls never get in trouble.
Her: Aww, thank you!
You: Plus girls are terrible drivers.
Her: HEY!! I'm a great driver!
You: Yeah right. I bet you can't even drive stick.