Let’s call him ‘Sal’

Two years ago a neighbor asked me out for a drink.  Let’s call him Sal.  Sal and I had a fun evening sharing stories and getting to know one another.  Having had family members in the same industry, we found plenty of great missives worth sharing.   It was obvious at the time that he was pursuing a dating situation – one for which I was not ready.  For a few weeks following our initial meet up, he kept asking until, in no other words, I said no.  

None the less Sal and I have become dear friends, and should a few days pass without one of us contacting the other, well, something then feels off.  When he was away for a month long vacation out of the country it felt odd having no connection other than Instagram.  He is one of the very few guys I’ve met who goes out of his way to communicate and include me in his circle of friends.  And when I came down with COVID, he brought over a batch of Hamburger Helper. 

Sal grew up in a lovely home in a mid-sized mid-western city.  His father was a cop and his mother a very accomplished socialite.  I’ve met them both – and am always invited over when they happen to be in town.  True to their nature, his father stands back, scans and observes the environs while his mother talks, spars, interacts, and explores them. 

At the time Sal had a long-standing career with a prestigious foreign bank that maintained a U.S. office in Chicago.  His lifestyle was reflective of his career and income.  A beautiful, well appointed home.  Nice car.  Plentiful vacations both near and far.  He’s in his early 50’s, swims and boxes weekly,  has a body reflective of this, and has a personality that is the kind that immediately puts people at ease. 

Around mid summer of this year Sal lost his job.  And although he had received a sizable year-end bonus in December last year, the loss of his job meant the loss of his income.  Fortunately, around this time last year, Sal decided to rent a room to a friend of his who had moved to Chicago and needed a place to live while establishing himself in a new city.   The added income from temporary roommate has staved off any catastrophe and has given Sal time to find a new job.  Coming up on four months, Sal has only had two interviews, neither of which has proven successful.  

Last month, in response to growing angst over his future finances, Sal became a sex worker.  

This didn’t come as too much of a surprise considering what I know about his sexual appetite but what has surprised me is the level of success he’s had in doing so.  Sal is booked for his services several times throughout the week and already has a handful of repeat customers.  

Sal bills himself as a masseur and has a listing one one of the most popular sites.   The site where he lists his services has 154 listings for men in Chicago in the same vocation.  To be fair, he’s actually pretty good at it.  I’ve experienced it – the massage part that is.  He asked if he could practice on me.  A friend of his had created an hour-long voice memo talking Sal through the ‘mechanics’ of an sensual massage.  Sal wore an earbud and followed the directions as he worked on me.  I thought that was quite clever – and on par with the way Sal approaches things. 

Sal’s listing highlights his massage background – though he is untrained and unlicensed, and shows a variety of photographs, some of which were shot by me.  I also wrote the copy of his listing.  Sal wanted copy that stood out from the usual and I was happy to help him.   

Still, with a 154 listings, Sal’s doesn’t stand out all that much.  I’ve seen a few of the other guys listed on the site, a couple I know from the gym, one is a former college, and a couple others I’ve seen around town.  I know of one guy listed on the site that is legitimately trained in massage.  There may be others.  None the less and for the most part, the site is known as a place to find a sex worker that has reviews from previous clients. 

Sal has given me permission to document parts of what’s taking place.  No real names will be used and locations will be anonymized for privacy and security reasons.