Crossed Dressers [Savage Love]

My wife has been seriously ill for three years, and I have been her sole caregiver. The doctors here weren’t getting the job done, so we made the difficult decision for her to move 2,000 miles away to start over and be near her family. Our sex life has been nonexistent since she became ill. She offered me a “hall pass,” with two rules: (1) It couldn’t be anyone I worked with, and (2) she didn’t want to know about it. She offered multiple times, but I was taking care of her 24/7 and never used it. I started to consider using it after she moved, but I didn’t want to just find some random person on Tinder. You see, I am a cross-dresser. My wife knows. She’s never seen me dressed and isn’t interested in knowing more about it. So instead of paying for a traditional escort, I found someone who would dress me, do my makeup and go out to dinner with me, but no sex. We met three times. However, one time, I did hire a trans woman who dressed me, and we did have sex. Obviously, I had to lie at times about where I was when I was using my hall pass, but I considered it a white lie to meet Rule No. 2. But my wife flew home unannounced to get her things (with her ex-husband along to help) and found my clothes out and quickly got out of me what I had done. She was beyond pissed. She says I had a hall pass for sex but not cross-dressing. She belittled me for the cross-dressing and said the sex was supposed to be a one-and-done thing. She knew I was a cross-dresser, and I derived more pleasure from this cross-dressing experience than having anonymous sex with an escort. My questions: Did I violate the hall pass? Was I wrong to cross-dress?

Dude Relishing Erotic Sexcapades Suddenly Entertaining Divorce

P.S. I am quite convincing when dressed and blend well in public.

Your wife went home to get well and “start over.” And it sounds like she got well—at least well enough to fly—and started over with her ex-husband.

I don’t think you were wrong to cross-dress, DRESSED, and if you violated that hall pass, it was only because your soon-to-be-ex-wife didn’t share all the rules with you until after you used it. It looks like a setup to me. Your soon-to-be-ex-wife gave you permission to fuck someone else—permission that came with rules that were disclosed and secret bylaws and codicils that were not—because, consciously or subconsciously, she wanted to catch you doing it wrong (in your case, DRESSED, doing it more than once, cross-dressing when you did it, etc.). Because now she can divorce you with a clear conscience, since she’s not to blame for the split—you and your dick and your dresses are to blame.

You might want to brace yourself for some hardcore blaming and kink-shaming, DRESSED, and for the very real possibility she’ll out you as a cheat and a cross-dresser to family and friends. But however the divorce plays out—and here’s hoping it doesn’t get ugly—at least you’ll soon be free to find a partner you don’t have to hide your cross-dressing from.

* * * * *

I’m a 22-year-old nonbinary person, and I’m debating whether to come out to my father as nonbinary. Complicating things is the fact that I tried to come out to him at 18 back when I thought I was “only” a hetero-leaning bi cross-dresser. He did not take the news well. Today we don’t talk about it, and I think he pretends it never happened. I’m wanting to move toward living in a less-gender-conforming way—including changing my name—and am considering making a second attempt. Pros: not feeling like I’m hiding who I am, maybe I get him off my back about kids, being able to be out on Facebook. Cons: screaming matches, strong possibility of being disowned and losing the modest amount of financial support I get from him, small possibility of him telling my mom (they’re divorced). Any advice?

One Foot Out

What’s more important to you, OFO: Living authentically, or living off your dad? If being your authentic self means giving up the money he sends you and you don’t desperately need his money, the choice is obvious. But if his money is all that stands between you and gender-nonconforming homelessness, you might want to think through your options, the risks and the rewards, before going nonbinary official on Facebook.

* * * * *

I’m a 25-year-old man who is mostly interested in women, but I like to mess around with men sometimes. I also love wearing high heels and makeup—not to “pass,” but just because I love it. Most women seem to be instantly turned off by these two things. I usually do very well with women, but they bolt when I tell them, and some have been quite hurtful. My family is very understanding about the high heels and my sexuality—even my father—but the average woman doesn’t seem to like it when I do something they deem “theirs,” which is so unfair. Women can do anything they please—wear pants if they like, have same-sex experiences—but I must submit or face the life of an outcast. Any advice on how to deal with this while also dealing with the bitterness and envy I feel?

Enraging Gender And Double Standards

Let’s start with those feelings of envy, shall we? While it’s true that women can wear pantsuits without causing alarm (or winning the White House), and while it’s also true that women can have same-sex experiences without freaking out the men in their lives (because straight men are likelier to be aroused than repulsed), women’s choices and their bodies are subjected to much more scrutiny, control and violence than our male bodies are, EGADS. Until politicians legislate against your right to control your own body (and wear your own heels), you can note the few areas in which women enjoy more latitude than men, but you aren’t allowed to bitch about them.

And this should put your pain in perspective: According to a new report from the Centers for Disease Control and Prevention, more than half the women murdered in the United States every year—55 percent—are killed by their husbands, boyfriends or exes. It sucks to be dumped for your sexual orientation or gender expression, I know. And people kink-shaming is more painful than non-kinksters realize. But none of your exes have stalked and murdered you.

Now the good news: There are women out there who dig men in high heels, there are women out there into bi guys, and there is a significant overlap between those two groups of women. If you succumb to bitterness at your young age because you’ve been dumped a few times—if you despise all women because you were dumped by women you wouldn’t want to be with anyway—you’re going to scare off the women who are genuinely attracted to guys like you. The women who bolted did you a painful favor, and you should be grateful. Because with those average women out of your life, EGADS, you’re free to go find an above-average woman who wants an above-average guy like you. Pro-tip: You’re likelier to find those women at a fetish party or club, or via a kink social-media site or dating website. Good luck.

On the Lovecast (, “sub space” with Mollena Williams. Contact Dan via email at ma**@sa********.net, follow him on Twitter (@fakedansavage), and visit

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