Before I answer the question, let me just warn you that I included three photographs containing nudity — they are part of a study of two models, and they are the subjects of my answer.
Well, More than fifteen years ago, I lived in a city with a famous red-light district, and sometimes, after a good night’s out, I walked passed the windows where the window prostitutes sat, waiting for the next costumers.
Many a times, I had noticed a beautiful young prostitute — I think she was about 23 or 24 (I was younger) -- and I thought she was stunning.
On one evening, I stepped in the bar where she was sitting — just like that — and I boldly asked her if she wanted to model for me.
She was extremely kind, and kind of baffled that I did not want to have sex with her (I did, but that was not my intention), and she agreed. Her name was June.
In the following weeks, I visited her once a week for about half an hour, and I made photographs, and drawings, of her every which way. I paid her as a model, of course.
The situation made me rather uncomfortable indeed. Working in a brothel, in the dark red gloom of the sex house, with the smell of used condoms and lubricant, and incense sticks. Sometimes other prostitutes passed by, totally nude, to take a shower, after a customer had left.
In the last night I was there, she spontaneously masturbated while I watched, and sketched. I did not know what to do (approach her ?), but I feared she would see me as a regular customer, so I did nothing.
(But I must be honest, dear friend: there was only one thing that I wanted to do at that very moment, and it wasn’t drawing. I still regret that moment, but what could I do ?)
Some years later, I met a woman who was just starting as a part-time nude model (and occasional sex worker), and I also made a study of her body. I photographed, made drawings, we talked. She was Alexandra.
(That situation was also rather awkward, since she was a top lawyer, and not one other person knew what she was doing when darkness fell.)
Here are two (vague) photographs (I was into vague images at that time) of our very first session:
Eventually, I composed one pastel painting which merged both encounters into one.
I called it “Faceless girl (in stockings),” and I still dream, whenever I see it, about the missed opportunities.