Michigan Ave

To your surprise instead of walking out to the car Alice pulls up the Uber app on her phone and types in an address.

"Why don't we just drive? Wouldn't that be faster?"

"We're heading downtown and parking would be a pain, this is way easier."

You had expected to be headed to the nearby mall but it was definitely true that downtown Chicago had much better options than the rundown suburban mall nearby.

You slip on your flats and practice walking while you wait for the driver to arrive. As long as you focus on it you can mostly walk in a straight line without stumbling, you were going to flat out refuse if Alice wanted you to try on heels though.

Soon a black escalade with tinted windows pulled up to the corporate parking lot. Alice checked the plates to be safe but it would have been an astronomical coincidence for someone to just happen to pull up to the deserted parking lot in the middle of the day.

"This is us, I ordered an Uber Chauffeur so he'll be our ride all day, good to have a place to put the bags."

She says excitedly.

Suddenly you're a little uncomfortable that someone else is going to see you as you are now. You were so used to being deathly afraid of being caught en femme that you couldn't shake the feeling that someone was going to call you out as an imposter.

An attractive man in a nice suit stepped out of the driver's door and opened the door for you. You weren't used to service like this. Even the cheapest Chauffeur option was pretty expensive and this was definitely not the minimum package.

You sit on the nice leather, you weren't sure if it was the premium interior or your new expanded rump providing the extra cushioning but it was very comfortable. Alice joins you on the other side and the driver gets in the front seat.

"Good morning, I'm Geoffrey and I'll be your chauffeur today, you two beautiful ladies are headed to Wilfurd on Oak first right?"

You blushed deep red at being referred to as a Beautiful lady as Alice nodded.

"That's right, you'll be keeping us company during a little shopping spree. Me and my best friend Penny here just graduated and our trust funds are finally available!"

You bristle a little bit at being referred to as a 'friend', but that was the deal. And as far as cover stories went being a couple of trust fund girls would serve you fine.