A Trans Woman’s Worst Nightmare

Photo by Hailey Kean on Unsplash

The Transamorous Network offers free 1:1s for trans-attracted men or trans women to chat with us and learn whether what we offer can help them live more fulfilling, happy lives.

Most times those conversations offer insight and satisfaction for everyone involved. In rare instances though, something else happens.

That’s what happened this morning. This conversation offered insight into what many trans women experience in their attempts to fulfill their relationship dreams. It also sheds light on why trans women degrade men who naturally find them attractive.

A classic connection

Not many schedule a Free 1:1. Especially since we implemented a $25 refundable fee to dissuade men who schedule a free session (perhaps while drunk or high) then don’t show up.

We know what we offer the trans community benefits that community. Over time we’ve spoken to many, many trans-attracted men, trans women and people who don’t fit in those categories, yet express trans-attraction. Many such people thank us for what we do. But seeing our clients transform their lives prove what we offer helps.

Then there’s “Josh”.

Josh got on his free 1:1 this morning. Hispanic and in his 60s, Josh has been single for 18 years. Before that he was married to a cis woman, who divorced him after she discovered him cheating with another cis woman.

Like many trans-attracted men, Josh’s past includes experiences where he learned about and enjoyed sex with men at an early age. He also enjoyed and still enjoys wearing clothing seen by society as “Women’s clothes”. He wears nylons and garters under his male clothes and loves wearing negliges at night.

Josh married a cis-woman because, in his words, he was “battling what he really wanted” which included expressing submissive characteristics in bed.

And also, like many trans-attracted men, Josh first encountered trans women through porn. This happened in the last year, and since that discovery, Josh found himself irresistibly trans-attracted.

Marriage often, but not always, can smoke screen what’s really going on for both parties. Which is why they often end in divorce.

Stereotypes prove the rule

Many trans women encounter men like Josh. Josh is in his very early stage of the chaser to transamorous journey. This was clear from the first few seconds. He referred to trans women as “shemales” and “transexuals”. He fixated on the idea that they had penises and expected a trans woman would be happy being with a man who dresses in women’s clothes.

Josh expressed fantasies of him “doing” the trans woman and then her “doing” him. When I asked what else he liked about trans women beyond his ideas of what sex would be like, he offered very little.

“I like that I could take her out, wine and dine her,” he answered. “Then we’d come home and cuddle on the couch, with me in my lingerie.”

He mentioned nothing about what this trans woman might think, whether she might be intelligent, thoughtful, generous, kind, interested in world events, or interested in having children. Josh didn’t consider the amazingly admirable fortitude needed to go through what trans women do to align with what they know they are. In other words, he didn’t see his future partner as a person.

Still in the closet

When I gently explained more dimensions to trans women exist beyond where he focused, I felt him almost immediately become defensive. I explained how “shemale” and “transexual” were not the best terms, which he accepted. Then, changing the subject deliberately, I asked him what his friends and family thought about him wearing women’s clothes.

“Oh they don’t know,” he said. “They’d be devastated.”

“Why does that stop you from being who you authentically are and sharing that with them?” I asked.

He said he didn’t think he was being inauthentic by not sharing all of who he is. So I explained to him that so long as he wasn’t out and about about who and what he really is, and what he really likes, finding a match to what he wants will present challenges. I also suggested the way he talks about trans women indicates he isn’t quite ready to meet someone. Trying to do so, I suggested, would produce unhappy outcomes.

That’s when the conversation shifted for Josh.

Being on the down low (DL) indicates for the down low person that he harbors stories creating a reality he’d rather not have. But the DL person doesn’t know that, which is why he’s getting the results he gets, including feeling of shame and insecurity. (Photo by Kristina Flour on Unsplash)

Why women meet men like Josh

“Who do you think you are?” he responded. “You don’t know me.”

“I’m going off of what you’ve told me,” I said. “And what hundreds of men and trans women have told me.”

Josh didn’t like that. I suggested he had a lot of preconceived ideas about trans women. Those ideas, I tried to explain, would cause him more difficulty than satisfaction because he’s not a match to what he thinks he really wants, which is a loving relationship with someone who happens to be trans.

Josh told me I was not making sense, that I was not listening. Moments later he hung up.

Clearly these kinds of men exist. They are the kinds of trans-attracted men trans women meet a lot of the time. They aren’t ready to meet anyone seriously because they’re still trying to figure themselves out.

Experience often presents the best “figuring out” opportunity. Often that means meeting trans women via sex worker venues, or through dating sites. And, usually, that means men like Josh meet women who match who Josh is being.

That means a trans woman on equal story footing. Such trans women, like Josh, are unclear about what they want, insecure in their own self-acceptance, and harbor inaccurate stories about dating, what’s possible and what they want. In many ways, they’re transgender versions of Josh. So they’re perfect matches.

The best way, believe it or not, to meet your ideal match is becoming that which you’re wanting. That means seeing the best in everything you experience. That’s what telling the best stories is all about. (Photo by Nathan Dumlao on Unsplash)

Trans women don’t need Josh

Just because men like Josh exist doesn’t mean such men need be part of a trans woman’s experience. But they will when a trans woman harbors stories which make them a match to such men. If you’re trans and you think Josh is a “tranny chaser”, for example, that story tells me you’re on track to meet your Josh.

And yet, such men and the women they match with benefit each other. Through experiences with each other, a trans woman and such a man learns what stories need attention. It’s good knowing that because, if they don’t know what stories need attention, neither person fulfills their dreams. Particularly when it comes to relationships. Which is why many compromise.

So while men like this comprise many a trans woman’s nightmare, they can also be the best thing that happens to a trans woman. For in the experience the woman and the man stand in opportunity. Seizing that opportunity guarantees a new experience with better matches offering better opportunity.

Better matches don’t come guaranteed. People sometimes never get over their negative stories. That doesn’t mean you can’t be the exception because they’re always are. The question is: are you?

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