A couple months ago I had a date with someone whom I had been exchanging emails.  I don’t remember if it was a scheduling conflict or inability to agree on a price that led to the delay.  I remember it was a Friday when he contacted me.  He was insistent that we meet that night.

Cassandra, please, he said.  I just got laid off today.

Of course, the overly cautious Chinese in me was thinking, you just got laid off. Is it really a good idea to blow money on a hooker right now?  But the hooker in me just saw the money.  Better I take it than someone else.

We agreed to meet, but then came the bigger issue to resolve: the kind of sex that he wanted.  The picture in this post is the same pic that I used in the CL ad that lured him in.  My platform stilettos really did a number on him.  He wanted to cum on it and then lick it off.  He wanted me to stick it up his ass.  He wanted me to jerk him off with my stiletto up his ass.  He wanted to swallow my load with the stiletto up his ass.  It was just infinite variations involving my stilettos and his ass. 

Take a good look at these stilettos.  They are thin and sharp.  Very Single White Female.  Can you imagine having this sharp, pointy object up your ass and risk me rupturing your rectum?  The stilettos are SEVEN inches long, so maybe his lower intestines are at risk too.   And I can just picture me accompanying him to the Emergency Room, having to confess to the nurse that, Yes, I’m a Hooker.  And Yes, I stuck my heels up his ass because he paid me.

Beyond the concern for his personal safety was my concern, which was that I DIDN’T WANT SHIT SHIT SHIT ALL OVER MY HEELS!   People, I use these heels to make money.  I don’t want them covered in shit.  My other customers don’t want that, either. 

I ended up wearing zip-up boots with sensible, round heels when I greeted him at the door.  I know, I know: the exact opposite of what a stiletto-fetishist wants.   And just so he couldn’t get any ideas, I had rounded up all my high heels and hid them in Reuben’s room.  I would have been OK if he wanted to end the date right then. 

He didn’t want to end the date.  He just wanted me to cum. In under a minute! Seriously.  His buddies were taking him out for drinks.  He was on a timeline.  He had to swallow my load before he could go out and commiserate. 

I was a mere check-off on his List of Things To Do When You Lose a Job.  First on the list was to hire a prostitute and act out your kinkiest fantasy.   Follow that with drugs and alcohol.  The motto is “Fuck tomorrow, enjoy the rest of today.”

He was a pretty cool guy, I have to say.  That kind of attitude takes balls.  Getting fired, being let-go, downsized, laid-off, eliminated — even if you know it’s coming, you can never adequately prepare for it.  The shock of having the rug pulled out from right under you. 

When I was fired I took a tab of ecstasy and soaked in a hot bubble bath until three in the morning.  The wound to your pride, your sense of self-worth, oh it stings.  I couldn’t even walk around downtown San Francisco because I was afraid of running into my former co-workers.  I later moved to another state and started an entirely different career.

After you do prostitution for a while most dates are just blurry, vague memories.  I haven’t thought of this guy again until today.  He did email me afterwards to say how much he enjoyed me cumming in his mouth.  He wanted to come back and see me once he got a new job.  That was the last I heard from him. 

I hope he’s doing well.

Who knows, maybe next time I’ll just fuck him with my stilettos and let him keep it as a souvenir.

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