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I tried to look fabulous, sexy and sophisticated, when I met Brooke that night.  Brooke, as explained to me by Jackie, was going to be my phone girl, so I had to make sure she thought I was hot and classy enough to book high and often.  I had no idea what an escort would wear. After much staring at my closet, I put on a tight turquoise satin button down shirt, my black satin pants, and my knee-high boots.  I thought I looked pretty good.

But I was wrong.

“You’ve got to look classy, honey,” Jackie told me, just after I’d shown up at the agency and been introduced to Brooke, an average looking woman with a headset firmly in her ear. She never stopped taking calls while I was there, merely shaking my hand briefly while negotiating some girl’s rate with a prospective client. 

“I want you to work the really rich ones,” Jackie explained.  “Lots of money.  You need to look expensive.  Not like you’re coming over to my house to watch a movie.”

“So what kind of outfit should I wear?”  I really didn’t know how much better I could do.  I certainly never dressed like this to go to a friend’s house to see a movie.  If this was casual, I was screwed. How much fancier did I need to go?

“That’s a nice shirt.”  She fingered it thoughtfully.  “Great fabric, and it shows your figure.  You want something kind of tight, but classy…” That word again. I clearly had no idea how to pull off classy. Her voice trailed off as she surveyed my entire figure.  “The pants are okay, too.  Maybe if you had a matching jacket or something?  And definitely heels.”

I must have still looked confused.

“A lot of the girls will wear a sexy top and then a matching suit or something,” she continued, trying to sound helpful.  “You want to look sexy, but you want to look nice enough to meet their sister, know what I mean?”

“Yeah, I think so.”  I was starting to get the right idea. And I would need to buy new shoes.

“Think first date at a classy restaurant.”

“Got it.” Obviously, none of my dates were ever at classy restaurants if I didn’t even own the right apparel. I had no idea what I could find in my closet that would be work, but at least I knew what Jackie was looking for. 

My first night “on call,” I ended up following Jackie’s advice to the letter, keeping the turquoise shirt, adding a black satin button down jacket over it as a sort of blazer, and switching to a pair of black wide-leg pants.  It wasn’t perfect, but it would do.  I bought a pair of black suede stiletto boots at Macy’s to complete the ensemble.  I wouldn’t be able to walk, but I figured my night would entail cabs and horizontal positions, so uncomfortable shoes would not be a problem. 

Waiting for the phone to ring, I lay on my bed, exhausted and scared at the same time.  My room was covered with clothes that hadn’t made the cut, but I couldn’t deal with putting them away.  I just stared at the ceiling and wondered how long I’d have to wait. Would I even get a client tonight? Would anyone want me? Was this idea as stupid as I thought it was in this insecurity-laden moment? I got up and stared at myself in the mirror. Did I look classy? Or did I look like a fraud? Would anyone know my shirt had only cost $10 at the vintage clothing store in Williamsburg? That apparently I didn’t know the meaning of the word “classy”? Would I be able to pull this off?

Ten minutes later, the phone rang.  It was Brooke.

“Honey, I’ve got a call for you.”