What was the crossdresser thinking about?

27 May

Memorable sight on the street last weekend in New York City…

On Eighth Avenue near 48th Street around 3:00 p.m. on Saturday 5/19/12, a couple. A very pretty black-haired young woman in a black dress with a flared skirt, holding the hand of a not-handsome man in a blonde wig, heavy makeup, red and white minidress with horizontal stripes, and bony bare legs on strappy heels. He looked nervous and uncertain as he walked. She looked confident and understanding. What was their story? Was she indulging a boyfriend’s need to crossdress and go out in the world? Or was she perhaps punishing him in some kind of roleplay game? Or was she a hired dominatrix taking a feminized slave out for a walk on the crowded sunny street? What was the crossdresser thinking about? I couldn’t help but wonder.

This drawing by the great Eric Stanton, which I found on the cool site Permanent Obscurity, captures the feeling of uncertainty in the man’s face as I saw it, even though the circumstances of the drawing are different:

The caption at Permanent Obscurity, “The loneliness depicted in [Stanton’s] characters transcends that of a mere ‘comic book’ artist” is also what I saw in the face of the feminized man on the street. Anxiety too. Of course, this is my interpretation. I have no idea what he was actually thinking. I turned to watch them, but they were quickly lost in the milling tourist crowds spilling over from Times Square.

Seen on Sunday 5/20/12 on Ninth Avenue: man who covered up his head in his zipped jacket, so he looked either as if he had no head, or his head was invisible. An invisible man. There are many scruffy fellows along Ninth Avenue between 40th Street going down into the 20s, but this one stood out in my mind. It was as if he had zipped up his face to commune with the darkness of his jacket (and the weather was quite warm, so it must have been hot in there, too).

I couldn’t find any comparable picture to conjure that up for you visually.

Finally, also on Sunday 5/20/12, I saw a girl in a tight skirt, high heels, and a halter, sashaying into the Dream Hotel on 16th Street near Ninth Avenue. Literally a head-turner and not just for me. She was almost like a cartoon out of the great Bill Ward:

Her butt did look like the one in this cartoon, although she wasn’t dressed with stockings; and her expression of indifference to everybody ogling her was just about the same. I found this pic at the site Live Auctioneers.  I don’t resemble the guy in that hat although my gaping expression was probably similar.

On another note, I found an intriguing book at a memorabilia show last weekend, yet another addition to my small library of tomes about the history of prostitution throughout the world–a subject I always find interesting. I was once even on the radio back in the 1970s to discuss an article I wrote myself about the history of brothels for the men’s magazine Swank.

What a seedy title, no? And blunt. Will have to dip into it soon. (Hmm, is that a pun–“dip into” it? Note to porn writer self: Must consider my possible sexualization of books as proxy vaginas. Topic for a future post?)


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5 responses to “What was the crossdresser thinking about?

  1. Lulu Simawati

    May 28, 2012 at 11:57 pm

    oh, it’s your fantasy ?

    • irvoneil

      June 3, 2012 at 7:34 pm

      Not my own favorite fantasy but I was interested in what was going through the guy’s head as he walked en femme down the street with the girl. I guess I was thinking like a story writer. Thanks for reading and leaving a comment!

    • explorer3000

      April 27, 2018 at 4:15 pm

      hot fantasy………..

      • irvoneil

        April 30, 2018 at 3:31 pm

        Thanks, glad you liked it!


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