This week in Savage Love: Crossed off

I’m a 35-year-old bisexual man in a LTR with a man. My question, however, has to do with my parents. As an adolescent/teen, I was a snoop (as I think most of us are, looking for dad’s porn stash, etc.). I was probably 12 or so when I found evidence of my dad being a cross-dresser. There were pictures of him in makeup and women’s clothing, and correspondence (under an alias and to a separate PO box) with other men interested in cross-dressing. As far as I could tell, he did this alone in hotel rooms while on work trips. Two years ago while on vacation, it came up while my mom and I were at dinner. She had recently found evidence, and she needed to take a short break to visit a friend out of state to process. She suggested I bring it up with him (I guess) because I’m queer and she knows I used to help host pansexual play parties. My dad is a devout Republican and comes off as very masculine. I see them only a couple times a year. Should I try to bring this up with my dad and let him know that I’ve known about his cross-dressing for more than 20 years and offer my knowledge about kink and alternative sexuality? Or just let him do his thing and we all retain the illusion of ignorance? My parents are still happily married—and whether it is more companionate than lusty, they love each other and have been married for more than 40 years. Your take would be appreciated.
Son Of A Cross-Dresser

Why does your mother want you to talk to your dad about his cross-dressing? Does she want you to talk him out of it? Does she want you to convince him to include her on his cross-dressing trips? Does she think he would benefit from attending a pansexual play party with his adult bisexual son?

Unless your father is in some sort of emotional distress or your mother is in some sort of danger, I really don’t see the point of this conversation, SOACD. It doesn’t sound like your dad is struggling with shame. If your dad had to abuse alcohol or smoke a crate of meth in order to give himself permission to cross-dress alone in a hotel room, you surely would have mentioned that fact. And if your father was having unprotected sex with the other straight male cross-dressers he corresponded with, you surely would have mentioned that, too.

From the details you included in your letter, SOACD, it sounds like your dad has successfully integrated cross-dressing into his life without harming himself or neglecting and endangering your mom. You could say your parents had a long and loving marriage despite the cross-dressing… or you could say it’s possible your parents’ marriage is an ongoing success not despite the cross-dressing but because of it. If dressing up in women’s clothes and occasionally escaping the confines of masculine performance helped your dad feel centered and emotionally whole, having this escape and having some people he could be open with about it—some straight male cross-dressing peers—could have made him a better husband and father. (It’s too bad it didn’t make him a better person politically, but you can’t have everything.) And while it might have been better for everyone if your dad had been open about his cross-dressing with his wife and kid(s), that ship sailed a long time ago.

I don’t see what this convo—coming 20 years after you discovered his cross-dressing and two years after your mother discovered it—will achieve other than embarrassing and humiliating your father. Even a married person has a right to some small degree of privacy, and each of us has a right to a small zone of erotic autonomy. Your parents’ long, loving, successful marriage coexisted with your father’s cross-dressing for four decades, and I don’t see why it can’t continue to coexist with it now. And if your mother is sad that your dad never shared this with her and wants to reassure him that he didn’t need to hide this part of himself from her and that she loves him just the same, she doesn’t need to deputize her bisexual son to initiate that conversation. If she thinks it would be a relief and not a torment for her husband to know she knows and that knowing hasn’t changed how she feels about him, she should tell him.

I’m so sorry, PTP, but it would appear you’ve lost the unemployed guy with the drinking problem to another. But take heart: You’re young enough to meet someone else, someone who wants what you want and doesn’t want what you don’t. I’m certain that after meeting this person—or even long before you meet them—you’ll be able to recognize that your ex did you a favor. Sometimes we dodge the bullet, PTP, but on rare occasions the bullet dodges us.

P.S. I know about this because he told me—I didn’t stumble over his Twitter account.

You’ve already told your brother the internet is forever and the low-key, low-stakes pseudo sex work he’s doing could come back to haunt him, FINDOMS. Beyond that… well, there’s really not much more you can do. Your brother is an adult, as are the men paying “tribute” to him, as they say in FinDom/FinSub Twitter, and he’s free to make his own choices. As for your parents, why is explaining where your brother is getting all those new shoes your problem? If your brother is old enough to set up his own Twitter and Venmo accounts, he’s old enough to come up with a plausible lie about those shoes.