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Love Walter: Why’d You Come in Here Lookin’ Like That

Dear Walter,

I’m a gay man in my twenties experimenting with both my fashion and sexuality. I also look like a girl and sometimes I wear women’s clothes. But I don’t identify as trans either. But I’m meeting all sorts of guys who think that I am. It’s almost like I’m their late night fetish. And I don’t know how to deal with this especially while dating? How do I maintain a healthy relationship and still wear what I want?

—Androgynous Dresser


Dear Androgynous Dresser,

I am not a transsexual either. There’s a meeting in the ladies room. But I’m using the men’s bathroom. No need to call your Senator. We live in an age where you can transition your private parts, or use them on married men from New Jersey. But, it’s not my thing. 

I enjoy an androgynous mix of kilts, tanks, and jewelry. One Friday night after a couple of cocktails and sample sales, someone handed me a flyer stating:

“Transexual wanted! A reality show producer seeks a transvestite, transgender, or transsexual person. Looking to pay up to $500+ a day….”

Oh, my!  At $500 a day, I could be!

My mind spun with thoughts of spending so much cash. Where am I going to find some breasts? I could ask someone at the pier. Why do they think I’m a transsexual?

We live in an environment where dressing like our straight male counterparts is ideal. I meet so many of these cookie-cutter “masculine” men, who by day don t-shirts and Timberlands, and by night they are performing fellatios on fellas behind the scenes in baggy jeans. 

Living in the city that never sleeps, you’ll find that the way we dress is not as queer as you think. What we wear, is a lot more closeted. Men’s fashion remained stagnant for half a century. Visit a gay bar, and you’ll find most guys dressed in t-shirts, jeans, and baseball caps. When did homosexuality become a homogenous decree?

I get running around the village in a black kilt and white boots aren’t the height of masculinity. But preferring an androgynous mix of fashion is not a transsexual make. Remember when it was stigmatized to cross-dress in women’s clothing? 

Visions of middle-aged men in ladies lingerie like Robin Williams in Mrs. Doubtfire—the scene on the bus where his leg hair protruded from his soggy hosiery. A man darted his eyes at him with disapproval. Why did this flyer affect me? And all of these memories resurfaced on this letter. 

I’m not looking for acceptance and you shouldn’t either. People judge, while transgender men and women remain misunderstood. Questions like do you have a penis? Or does not having one disqualify you as a man? They linger on pursed lips like Herpes. 

Once upon a time in a distant past, I traveled to the video booths off 42nd street, where hood boys hung out. Broke black and latino men moonlighting as low-end rent boys. One guy approached me with a complexion marked by crystal meth, groping the front of his baggy blue jeans.

“You generous tonight?”

“Hell no, I’m checking out the scene.”

“Na, your faggot ass got me fucked up,” he said. “You can’t come up in here.” 

One of the five men perched on the balcony like a band of zombies threw a Pepsi can at me. There was a war between the “homo thugs” and “t-gurls.” And I didn’t qualify for either role. 

These booths were like portals of poverty where the disenfranchised competed for cocks and clients. I heard love was a battlefield but money was the motivator. 

I threw that Pepsi can back along with a jar of condoms. Someone had to fight for me and I was my best advocate. The Asian owner escorted me out. I never felt more discriminated and disrespected by my own people. 

Once while in the throws of passion where I spent five days in a hotel, he mentioned that he wanted to buy me breasts. To him, me having “titties” made me more desirable. He had a hard time finding transgenders in their natural habitat.

Being transgendered transcended wardrobe. Man, I feel like a woman when I’m around the most masculine men. Tough guys calling my ass pussy to heighten their own masculinity. I’m just a girl like No Doubt whenever I let daddy drill me.

But I love being a male. I enjoy having a penis.

Wearing a skirt doesn’t mean I want to transition to a woman either. A real man will see that. And he’s out there. Sometimes putting on a pair of pants will draw him right in. Then reveal the rest of the collection when he falls in love with you. 

Don’t give him all of you at the first twilight. 

Love, 

Walter


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