Hookers

The first time I picked up a prostitute – it was a mistake… but more on this later.

I have only been SOLICITED by a prostitute once… I was late for an awful temp job at an insurance company on the upper east side and as I rounded the corner I nearly collided with someone. She was a normal looking black woman - maybe in her early 40’s – wearing a purple track suit. I was in my early 20s at the time but in my pleated khakis and green LL bean backpack I probably looked 14. She was leaning against the building, one leg propped up against it James Dean style. Very cool and relaxed. She caught my eyes and held my gaze. She had a toothpick or lollipop stick in her mouth. Without hesitation she asked me a clear and steady voice:

“How’d you like to start your morning off with a blowjob?”

"Uh, no thanks" I said. My voice wavering.

“Okay, suit yourself,” she said with a shrug of her shoulders as if I was refusing the extra insurance on a rental car. It was weirdly casual - I felt like I was saying no to a second helping of blueberry cobbler.

I went upstairs and stared at my cube wall and processed our brief exchange. I admired her moxie. I sometimes get nervous simply asking someone for directions. But she just asked a complete stranger if she could put her mouth on his penis and she didn’t even blink an eye. Impressive.

And where was she going to blow me at 8:15am - On the corner of Lexington and 86th? In between 2 parked cars? In a deli? In the starbucks bathroom. I’m still not sure how she thought she was going to pull it off. Maybe she doesn’t think that far ahead – her first goal is to get someone who’s interested – then she moves onto the logistics from there. not a very good planner – probably a Sagittarius.

I walked on the other side of the street the next day. I looked for her on the corner but she wasn’t there.

- The first time I picked up a prostitute was the only time I picked up a prostitute.

I was driving at night to Midway airport in Chicago. A blizzard erupted that morning and all flights were canceled - a friend was stranded there and instead of letting him spend the night on a cot – I decided to take my chances on the treacherous road and pick him up.

I could barely see out the front window of my ex girlfriends grey 1987 Camry. This was a real Chicago blizzard – where the gusts of wind are so strong it moves your car. It was also about 10 degrees. Completely MISERABLE. Old timers in Chicago call the winter wind The Hawk – because it swoops down from the sky and rips your face off. So there I am driving on the main avenue towards the airport. It was just plowed so I was moving semi-fast. As I pass a bus stop on my right I catch a glimpse of someone huddled and waiting for the bus. I looked back in my mirror and see that this person is wearing a light jacket and either shorts or a miniskirt.

I was shocked. This was the worst storm I had ever been in… who would be out in this weather dressed like that!!!!

I drove along and began to feel horrible for this person.

I did a u-turn and came back around. I slowly pulled up to the bus stop and rolled down the window – I yelled “get in here!!” she did.

She was a 20 something year old girl with dirty blond hair wearing a miniskirt, boots and a jean jacket.

“What are you doing out there” I said – my voice a mix of anger, confusion and bewilderment. “are you crazy?” a car started honking behind me.

“Where are you going?” I asked as I pulled back into traffic. I aimed the heater directionals at her legs.

She was looking out the window. Not looking at me. I couldn’t see her face.

“I’m going wherever you’re going” she said.

“What?!” I said. “I’m going to the airport. I’ll drop you off somewhere…. Somewhere along the bus route. I’m heading the same way.

Her shoulders slumped down. And her voice lowered.

“Just take me back there.”

"Where?"

To the bus stop… back there.

"What? Take you back to the bus stop? But I can drop you off somewhere. Just tell me…"

"No. just take me back to the bus stop."

"Ok" I said. I moved over to the left lane to take my second illegal u-turn of the evening.

We sat in silence at the red light. The snow falling all around us. The heater blowing on high.

“You don’t get it do you” she said.

"No I guess don’t," I said.

I started driving back to the bus stop.

We were stopped at another light about a block from the bus stop when she let out a sigh.

I looked over at her – at the boots, the jacket, the skirt and went “Ohhhhhhhhh”

She shook her head up and down and said “Yeah.”

I stopped at the bus stop.

"Are you sure I can’t take you anywhere."

"No I’m fine" she said.

"I don’t have any money or I’d give you something."

"Its ok" she said. She looked at me one more time her look said "so you’re sure you're not interested?

I just stared back with a half smile.

She opened the door stepped out into the wind and the freezing cold.

I stayed for a moment watching her through the window. She wouldn’t look at me – just kept staring into the lights of the oncoming traffic.

I drove off - picked up my friend at the airport – and when I drove back past the bus stop she was gone.