Married, but with lingering desires

Timaree answers your questions about sex, love and relationships

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Sex advice shouldn’t be syndicated. We wanted a local feel to ours so we’ve enlisted the sound advice of resident sex professor Timaree Schmit. Have a question about your love life that needs answers? Email her at asktimaree@philadelphiaweekly.com. | Image: Redlite photos

Q: I used to date cross-dressing males before my marriage, but was not open about this part of my life. My wife has been forgiving with this (it came to light a few years into the marriage), but is not open to any cheating. I treasure her patience with me and truly want to remain married. For now, I am abstaining from seeking out any friendship from the transgender community, but I feel like there may be opportunity to meet another local married male in the same boat and help each other out. Do you have recommendations or resources I can explore?

Thanks for sharing this. It was undoubtedly a challenge, given you’ve kept this so clandestine – taking years to reveal it even to your spouse. That said, I have a lot more questions and points of clarification before I can be useful. 

First up! Let’s talk about … what we’re talking about. 

Gender and sexual orientation are concepts that we continue to learn about and the vocab shifts rapidly. Some terms people used to describe themselves decades ago are considered slurs today. I don’t want to assume anything, so instead let’s review some terms that are prevalent now.

Cisgender means that the gender you were assigned at birth (like the doctor proclaimed, “it’s a boy/girl!”) is the same as the gender with which you identify. For example: if you were called a girl and as an adult identify as a woman, you’d be considered cisgender. 

Cross-dresser is often used to describe cisgender men who enjoy wearing clothes or makeup that are culturally considered feminine. Usually it’s for fun – maybe sexual or just because it’s relaxing. Really, cross-dressers can be anyone who wears clothes not expected or associated with their gender. Anecdotally, most guys who fall into this category consider themselves heterosexual, but that’s not a rule. Previously the word “transvestite” might have been used here, but it’s outmoded. 

“I don’t think monogamy is required for a lasting marriage, but if it’s what y’all continue to agree to, ostensibly that’s what you both want.”

Drag queens are people of any gender who dress up in feminine costumes and makeup for entertainment or artistic expression. Many drag queens are gay cisgender men, but certainly not all; non-binary people, trans and cis women can be drag queens too.

Transgender is an umbrella term for when the gender you were assigned at birth differs from the gender with which you identify. Some people who are trans seek medical care that brings their bodies into alignment with their identity, but not all do or can. Gender identity is an internal concept, so it’s not contingent on appearance, clothing or medical status. 

Next up! Let’s talk about what you want.

Again, I can’t assume anything. Let me just say that some of the most common reasons people message me are because they LOVE their partner and REALLY WANT TO STAY MARRIED but also would like to do [insert thing] that feels incongruous with that. 

I’m not entirely clear on what you’re looking for here, whether you would like to meet like-minded married men with whom to commiserate, want my professional dispensation for an affair, or are curious about exploring gender and sexual orientation – perhaps within the structure of a community. Maybe this is what you’re trying to figure out too. 

What I’m not about to do is condone operating outside the agreements of your relationship. It sucks that you felt like you had to keep this facet of yourself a secret. And it also sounds not great that your wife’s take on it is forgiveness – as though there is anything wrong with being attracted to trans people or engaging in cross-dressing or that anyone gets to approve/disapprove of your dating history. 

“Very often we come up with solutions before we’ve figured out the need we’re trying to meet. Then, having decided on a solution, we strive, argue, and connive to get something that maybe doesn’t make us feel the way we hoped it would.”

I don’t think monogamy is required for a lasting marriage, but if it’s what y’all continue to agree to, ostensibly that’s what you both want. Otherwise, you’d part ways and look elsewhere for a more compatible situation, right? It certainly wouldn’t be very loving to string someone along, consciously aware that they weren’t what you wanted. 

Finally, what can you do?

My highest recommendation is to devote energy to identifying your feelings. Very often we come up with solutions before we’ve figured out the need we’re trying to meet. Then, having decided on a solution, we strive, argue, and connive to get something that maybe doesn’t make us feel the way we hoped it would. I’d wager a good percent of the straight guys who cajole their girlfriends into anal sex or threesomes haven’t actually thought through WHY they want those things…but that’s another story.

Is this a sexual desire that is not being met? Could it be satisfied another way – like through porn, role play or fantasy? Is this a part of your own gender journey that you want to explore? Could reading more about trans experiences help you? Are you discontented with your life or relationship? Would it be useful to have a therapist talk through this stuff with you?

These are questions only you can answer. Ultimately, what you asked was a little vague, but thinking, reading, and talking about this is going to lead you closer to clarity. Don’t be afraid of asking your wife to be a part of this conversation. Treat her like a teammate, not your warden, and it’ll likely be less challenging to her. In any event, good luck!

Have a question for Timaree? Send an email to asktimaree@philadelphiaweekly.com.

  • Timaree Schmit Headshot

    Timaree Schmit is basically an episode of Adam Ruins Everything, but in the shape of a person. She has a PhD in Human Sexuality Education and years of experience in community organizing, performance art, and finding the extra weird pockets of Philly.

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