New York Cit-Dee, Dee One

As I wrote a couple of Sun-Dee’s ago, following my three Dees in Atlantic Cit-Dee, my destination between my races on one weekend and the music phestival in Philly the following weekend was four Dees/three nights in New York Cit-Dee. 

As I had been in NYC a couple of weeks before with my wife, both visiting my son, seeing the US Open (tennis), and a couple of Yankees/Cardinals games at Yankee Stadium, I had been thinking about coming back dressed for a couple of weeks. With me, anticipation is a large part of the fun of dressing; deciding what to wear, where to go, what to do, the whole enchilada. 

Between gear for races, and clothes for Dee, my hotel room often resembles a disaster zone. I managed to get everything packed in enough time that I could go on a morning walk on the beach, this time with a black swim top and my bikini bottoms. It was a nice morning and a good farewell to my time in AC.

I loaded my rental car with my luggage and bike case and drove a little over an hour to the Philly Amtrak station. I had some issues finding the parking garage, but finally figured it out and made the train. For comfort, I wore a halter top and slacks combo with my Red Keds. On the train I pulled out my quick dry nail polish and painted my nails. I rarely do a good job, but usually most people aren’t close enough to see them anyway.

As it was warm in NYC, after arriving at my hotel (a few block walk from the train station) and checking in–yes, the reservation was in my male name, and no, I don’t care–I changed into a cooler summer dress to wander around. My friends Renee and Ms. Dee-ism like pictures with backdrops, so I was looking for photo opportunities. I love just wandering around New York, doubly so in a cute dress. I went by–and into–St. Patrick’s Cathedral, a favorite of Ms. Dee-ism, and other landmarks like Rockefeller Center.

Anyone who visits NYC knows there are an unlimited number of food vendors on the streets, so in lieu of a restaurant, I got a gyro at a food truck next to Bryant Park and found a table to sit and eat, enjoying the day changing to twilight, feeling the energy of NYC. I like number puzzles (former CPA, go figure) so I listened to a band in the park playing cover songs, watching the sun go down and the lights go on, doing my puzzle and content with life.

Being in the city that never sleeps, via Google I located a bar with live music about a block away from my hotel. I had previously found a short on top–and short on bottom–LBD at Plato’s Closet and followed Ms. Dee-ism’s advice (“buy it, buy it, buy it”) and was just looking for a place to wear it. Tonight was the night.

I paired the dress with black fishnet stockings and heels (that I thought I could walk in, but I overestimated my abilities), and carefully strutted the block to the bar. I took a seat at the bar, and made limited small talk with the couple next to me, while eating a race’s worth of calories in my 28 layer cake. The cider on draft was also pretty yummy, and I drank my self-imposed limit of two.

Meanwhile, I was trying to take some fun (read: sexy and seductive) selfies, and texting them to Renee. I can’t explain why putting on a slinky dress with hose and heels makes me feel sexy, but it does. I’m straight, so dressing AS a woman to attract women isn’t the greatest strategy (plus, I am married, so I’m not out looking), but it is nice to feel desirable.

I’m sure Renee can’t explain it either, but she loves seeing me dressed. Three plus decades ago, before either of us were married, we engaged in some adult activities, and she helped me dress a couple of times. Even though we are both married, it’s fun to exchange some flirtatious messages about events which are extremely unlikely to happen. 

I texted her pictures I took in my hotel room, accompanied by this message.

Decided to get a drink and wear a wow dress

(I will occasionally send a picture to Renee and get a response picture with “Wow” in text).

Then at the bar, took some selfies, including the drink and the one with the bare shoulders, and sent this.

Trying for my alluring photo

Feeling my oats–and the alcohol–after some thought and hesitation, I upped the ante.

So, would ya do me? 🙂

Yes, I’ve drunk too much.

Renee’s answer?

Absolutely 

Would you do me?!

Mine?

Yes.

As Renee needed to sleep, and I needed to stagger (part heels, part alcohol) the block back to my hotel, the conversation ended there.

But a fun (unlikely) fantasy to daydream about, and in-Dee-d nice to know at least one person finds the female me desirable. 

Dee-two next Sun-Dee. 

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5 Responses

  1. DEE,

    JUST ABSOLUTELY LOVE TO WANDER AROUND CENTRAL MANHATTAN. OLD STOOPING GROUNDS AS TEEN> BEFORE MARIE ERA> HAVE FUN TO THE HILT GIRL.

    MARIE ANNE

  2. I can’t explain why getting dressed to the nines excites you. Or why it excites me. Perhaps because it flies in the face of convention.

    You are one of the few people who have seen me all dresed up.

    The same way my spouse and I refer to each other as “spouse”.
    It’s no one’s business what my sexual preference is. And saying spouse is free of the societal baggage that comes with “husband and “wife”.

    And whenever someone refers to my husband after I’ve said spouse, I say “why do you assume it’s a man”?

    I did not intend to pontificate on languge representating behavior. Ok, maybe I did.

    I love the pics, the woman in them, and the narrative!!!

    Lastly, thanks for the shout out!

  3. Dan Savage talks about the transgressive nature of things like gender bending. That could be part of it.

    As to assuming your spouse is male, Dan Savage also says everyone defaults to heterosexuality. These days, I try not to assume when I hear someone is getting married they have an opposite sex partner (made that mistake once).

    I will try for a few more pictures to keep you happy ..

  4. Dee, I love reading about your travels and adventures as Dee. Although I do not get out for extended trips as you do, I do manage to go to some musicals or concerts as Donna. Toronto is a pretty safe place for that. You look great in your outfits. Kudos to you for wearing what ever you feel like. As an aside, whereas you are a CPA (former) who likes music, I am a musician and former music educator who likes discussing math and taxes. (My sister is a CA, and we sometimes discuss such topics) Thanks for your travelogues and posts.
    Donna

  5. Thanks Donna. I definitely appreciate the feedback and the kind words. I have decided (and written about) wearing what you want to wear, even though some of those clothes are for a different age demographic.

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