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What does it mean when straight men sleep with crossdressing men?

“Girls are too easy to pick up,” admits Max*, a 27-year old New Yorker who works at a startup. 

“After a while it gets boring.”

Don’t get him wrong. He’s into girls. Like, really into them. A serial dater, his last girlfriend was an Asian American who he was “completely infatuated with.”

“But it’s a lot hotter when it’s with a certain kind,” he says. “It’s different and taboo, I suppose.”

He’s referring to crossdressing men, those who are completely feminine, have little to no body hair, and are “passable” — a term used when said guys look like cisgender females. “There’s a challenge and a certain taboo that makes it sexy and different,” he says. “But I’m definitely not gay and not into guys.”

Max isn’t alone in his sexual preference, though it’s one that’s completely discreet.

“My buddies don’t need to know about this,” he says. “It’s no one’s business.” More than being shamed or outed, the feelings are outright confusing, as sexuality usually is. If a dude likes to sleep with guys who dress up as women, what do we make of them? According to Dr. Joe Kort, author of the book, “Is My Husband Straight, Gay or Bi?” the predilection is completely normal.

“These guys are totally straight,” he says, reaffirming what mostly all of them have already known. “Women get really freaked out when they see their husband’s porn and it’s of men who crossdress. No, they’re not gay, they’re not even bi. You’re not going to find a gay or bi man attracted to a crossdressing man.”

Kort explains that there is a very distinct differentiator between sexual identity and sexual preference. “For many straight men, they are not interested in gay sex,” he says. “Again, this differentiates him from gay and bisexual man who would not be turned on I been with a guy in women’s clothes. It really comes down to who they ultimately desire to be with longterm.”

When it comes to crossdressers, the big turn on for men comes from a multitude of reasons, says Dr. Ian Kerner, a psychotherapist who specializes in sex therapy.  “Still others will say that a woman with a penis is a hot fantasy that plays into their power-play interests, whether dominating or submitting,” he says.

So where does this stem from? Is it innate or learned? While there are no current studies on this, Kort has a Kerner has a hypothesis: “Perhaps, for some men, having sex with a cross-dressing male would help them overcome internalized gender models and feel like they were still attracted to women, while enjoying a penis.”

“Other times it’s exciting to make the other made feel degraded or inferior, to be made into a bitch,” says Kort. “Or maybe they’re interested in the feminized male. It’s a blurring of boundaries.”

Or perhaps, childhood.

Corey*, a 26-year old from New Jersey, works at a wine shop. He says his fascination with crossdressers stemmed from when he was younger. One day, as he tells it, he got an erection when watching a drag queen on television. “Ever since then, I suppose, is when I fantasized about being with one,” he says. But these encounters seem to begin and end as one night stands.

“I don’t see myself with these people during the day and don’t want to see these people outside of their wigs and outfits. I’m really not into men and can’t go there, I’d lose my boner.” Dr. Michael Aaron, a New York-based sexologist, says this interest with crossdressers comes from fetishizing the male genitalia altogether.

“I don’t think most of these folks are bisexual,” he says. “Most would probably consider themselves heterosexual but also happen to fetishize the penis, just as they would a female body part as breasts.”

Says Kort: “These straight men would never go to a bar or get with another straight guy. They’d only do it if the guy is dressed as a woman. It makes him feel more like a man and reinforces being straight.” Sexuality, as Kort explains, isn’t black and white, rather, has “numerous dimensions to orientation.”

In his recent article for Psychology Today called, “Sexuality Is More Fluid Than You Think,” Aaron explains sexuality in two ways. 

On one hand, we have a nascent field of research (called ‘epigenetics’) that suggests that our genes get switched off and on during the course of our lifetimes,” he writes. “In addition …sexual fluidity is merely a matter of uncovering. In other words, they may not have realized they were interested in some aspect of sexuality until they tried it and realized that they enjoyed it.”

Meaning, a guy’s sexuality can twist and turn in every which way as he goes through life’s new experiences. It also might explain why a recent study found “she-male” porn to be one of the most popular categories for straight men

“To my knowledge, this has not been studied, but I wonder if the attraction to crossdressers is similar to that of ‘T-porn’ (shemale porn) or having sex with pre-op trans women, in that it features performers or involves individuals with a penis, but with all of external trappings of a female,” says Aaron. 

Ultimately, whether straight, bi or gay, or fluid, Kort makes it a point that these men are probably most interested in sexual fluidity, a topic we’re now learning more about. “It’s totally normal though,” he says. “We need to start eliminating shame and so do these men. There’s nothing to be ashamed of with your sexual identity, especially when sexuality as we know, is completely fluid.”

Attraction to fluidity? There’s nothing wrong with that. But the bigger issue could be objectifying these other men and turning them into objects of sexual desire instead of perceiving them as real human-beings. Ultimately, there are issues when it comes to fetishizing and the power dynamics that come to play with it. Additionally, the hypocrisy that comes with embracing someone behind closed doors but being ashamed of it in the public eye.

When it comes down to it, it’s an issue of the patriarchy and how homophobic our world still is. It’s also societal conditioning that fails to embrace that sexuality is a spectrum. But one needs to also be aware of exploring their sexuality at another’s cost. Because when it comes down to it, sexuality is never black and white and should be between two (or more) willing participants.

Here’s to hoping we can move forward with more understanding and fighting to end these toxic notions of desirability and what is and isn’t “normal.”

*Names were altered on the behalf of subject who agreed to speak to Very Good Light on the grounds of anonymity.