Q: 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 while I stayed behind. 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. Following rule #2, I didn’t tell my wife anything about any of these encounters. But then she flew home unannounced to get her things (with her ex-husband along to help), 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 that I derive more pleasure from cross-dressing than from 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
Q: I’m a 22-year-old nonbinary person and I’m debating whether to come out to my father as nonbinary. Complicating things is that I tried to come out to him at 18, back when I thought I was “only” a hetero-leaning bi cross-dresser. He didn’t 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
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’s 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 women out of your life, EGADS, you’re free to go find a woman who wants a guy like you. Pro tip: You’re likelier to find those women at a fetish party or club, or via a kink social-media or dating website. Good luck. v
