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Dear How to Do It,
I am a 44-year-old married man with a secret. Prior to the pandemic, I traveled extensively for work—and I would take advantage of my evenings in other cities to become “Tammy.” I’m a crossdresser. Over time, I became increasingly bold, and socializing during travel turned into flirting, which eventually led to experimentation and sexual activity with men while dressed.
I will add that I am deeply motivated by the attention and validation that I receive from men who are into this sort of thing. I’m actually not into the sex but feel attractive, empowered, and alive when being courted or pursued by a guy. The sex is just part of the deal. As a man, I have been introverted and shy and never thought of myself as particularly attractive. As Tammy, I look good and feel fantastic, alive. You might be surprised at exactly how many men in completely vanilla settings will hit on an attractive crossdresser. I certainly was at first.
So far, I have managed to compartmentalize this part of my life surprisingly well. Recently, however, I have been overcome by feelings of guilt and sadness. My wife is a wonderful, loving, attractive woman who does not deserve a lying, deceiving person like myself. I have tried many times to stop, and have managed to pause this activity for a while. The pandemic obviously put it on hold for a long time, but now that my routine is going back to normal, I recently had the opportunity to revisit Tammy and felt really bad afterward. I don’t want to continue to lie and deceive my wife, yet Tammy is a big part of who I am. I have had gender dysphoria my entire life and chose not to transition. Instead, I managed it somewhat by escaping to Tammy on occasion. I must admit that I have had a lot of fun with this, but it also has made matters worse because I have become a dishonest, deceiving person with my loved ones, even when I am an otherwise sincere and transparent person in all my dealings. What do I do?
—Truth or Tammy
Dear Truth or Tammy,
You wrote: “I don’t want to continue to lie and deceive my wife, yet Tammy is a big part of who I am.” Well, guess what? These things are not mutually exclusive. You can tell your wife the truth and you can keep being Tammy. How your wife will react to the truth is another matter. She may, in fact, decide to stop being your wife. But you owe her the opportunity to make an informed decision. I don’t feel that it would be much use to shame you and intentionally make you feel worse than you already do, but I also think you need to take a harder look at yourself and stop making excuses. You have been repeatedly dishonest over time. You may be sincere and transparent in all your other dealings, sure, but that is immaterial to your pattern of behavior. A chronic shoplifter is only in the stores he steals from for probably a fraction of his day. The time he spends not shoplifting makes him no less a thief.
You didn’t explain why you haven’t told your wife about Tammy. Perhaps this is a decision informed by past comments or general beliefs; perhaps you are simply assuming that she’d have a negative reaction based on cultural norms. A more troubling scenario would be one in which the sneaking around is part of the fun or even offers an erotic thrill. That’d be more difficult to untangle. But, look, the current situation is causing you considerable shame and distress. Your wife deserves better, you deserve better, and Tammy deserves better. She deserves to live in this world without having deception and cheating tainting her existence. The coming out process can be messy, and not everyone can bloom elegantly and flower-like into themselves; sometimes people get hurt along the way. I suspect that might be what’s happening here, and I don’t mean to excuse your lies but to put them into perspective and offer you hope of a healthier future. Consider seeing a therapist who specializes in gender issues. The World Professional Association for Transgender Health website’s provider database may provide you with some needed assistance.
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Dear How to Do It,
I’m a single trans man in his mid-20s. I’ve been on testosterone for about five years. Before I transitioned I lived as an out lesbian (and a gold-star one at that) with a few female partners over the years. I was never interested in men, other than perhaps jealousy from wanting to BE one when I got closer to figuring out my gender identity. However, after I began testosterone and started living as a man, I started to have fleeting thoughts here and there about men. The kicker is that for years, even as a lesbian, I would primarily watch gay porn. Something about primal sex between two men always turned me on. I know there is literature online about lesbians watching gay porn, and I’ve even seen some female-to-male forums discussing former lesbians, now trans men, developing an attraction to men.
About three or so years ago, I curiously ventured into the online gay hookup world and created a Grindr account. In that time, I’ve probably spoken with over a hundred men, all online, and never met up with one. I get off on sharing intimate photos back and forth. Even better if they send me snippets of them jerking off. Pretty much half the time I masturbate nowadays, I download all the apps where I have communicated with men anonymously (Kik, Snapchat, Grindr) and for the entire time I am pleasuring myself, I sext with various men. While I am jerking off, the idea of hooking up with a man excites me to no end. I talk a big game with these men too. But, literally as soon as I cum, I delete everything from my phone and am disgusted by the prospect of being with a man. I am just so confused by myself. Sometimes I think I’m bi, but the only time I want to be with a man is when I’m horny. Never do I see a man in public and think of him as attractive in the same way I do a woman. When I look to the future, I also picture myself dating women and settling down with one. I guess all this comes down to the main question: Do you think I am shamefully suppressing an attraction to men, or something else is going on? What is your arm-chair take on my sexting carousel when masturbating? I know telling someone what you think their sexuality is may be a fine line to walk, but I just really am at a loss for this habit I’ve developed.
I think you are luxuriating in the liminal. One of my all-time favorite studies examined Craigslist cruising as a self-contained behavior, that is, an erotic event in itself regardless of whether actual sex resulted in these online interactions. The study found that self-identified heterosexual and bisexual respondents were more likely to find erotic the process of browsing sex ads on Craigslist, the posting of them, and the email exchanges than the gay men who answered. Though “success rate” of such exchanges (i.e. resulting sex) was measured in the survey, it was not the focus of the report. The authors Brandon Andrew Robinson and David A. Moskowitz surmised that “in seeking to explore and experiment instead of enacting their desires offline, bisexual and heterosexual men seeking men might find internet cruising and emailing to be an erotic tool for sexual self-expression, satisfaction, and possible identity development” outside of venues specifically designated for gay men. Additionally: “The anonymity and accessibility of the internet allows these men to find pleasure in cruising for other men without having to reveal their own identity, without actualizing ‘gay’ (i.e., physical sex with another man) behavior, and also without upsetting their potential partners or having sex outside of their relationship.”
So, the thrill of the act could arise from how near-yet-far it is to sexual contact with other men. Much has changed since the survey was conducted in 2008 (the paper wasn’t published till 2013). Craigslist no longer allows sex ads, and geolocation apps like Grindr seem to be the primary means that men coordinate sex with men virtually. However, it’s not unreasonable to interpret your cruising as similar to that of the respondents’, just with 13 years of technological process under your belt. Perhaps this is so erotic to you precisely because it is not actual sex with another man, nor does it ever have to be, precisely by your choosing. Or maybe this is a way of you exploring a side of yourself that is underdeveloped, as you suspect. Certainly, it is not at all uncommon to be repelled by your turn-ons in non-erotic contexts—the disgust response tends to diminish when we are engaged sexually. You seem to have a good grip on what you’re into and feeling, which makes me doubt that you’re repressing much here. I think you’re just feeling things out, and your sexting with men could just be one of those “it is what it is” situations. No biggie!
Dear How to Do It,
I’m 30-year-old woman who has never had sex. I suspect I’m on the asexuality spectrum, since I do have crushes on men and women but I’m not easily sexually attracted to them. On top of that, I deal with anxiety, which annoyingly flares up whenever I try to start dating. Recently, I tried to push past my anxieties and got on a dating app mostly because the lockdown made me feel super horny and crave human touch. However, once I started talking to someone that wanted to meet up in person, my anxiety got so bad I had to go on medication and stopped talking to the guy. I think part of the reason my brain freaks out at the thought of finally having physical intimacy is because I’ve been putting it off for so long. I also think meeting people on dating apps isn’t ideal for my mental health; I think I would do better meeting people in person and having things develop organically, but honestly in COVID times that seems hard to do. Help!
—Horny but Hesitant
Dear Horny but Hesitant,
It’s hard to get over the humps we consciously avoid; over time, they can start to look more like mountains. But I have to wonder if there isn’t something else going on—could your reaction have anything to do with past trauma that you didn’t mention? Just something to keep an eye out for as you figure this out. You might do well to talk to or even consider dating other ace people—there are forums and apps that a Google search will turn up. It may be less intimidating to connect with people who know where you’re coming from (or may be coming from). I agree that apps are not for everyone—they can be impersonal, foster casual cruelty, and they deny access to some crucial elements of attraction (like the way people carry themselves). The pandemic rages on, yes, but things are more open now. You need not peruse a meat market where people are packed in like cattle and breathing into each other’s mouths to find a potential match—take up a group hobby or a sport or join a book club. Something to get you out and in front of people so that you can see their humanity and they can see yours.
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Dear How to Do It,
I’m a woman in my mid-30s who grew up in a very conservative Christian community. This is pertinent because it may be the reason I’m just not really that into sex, although when I left that community I spent a lot of time reading erotica and sex-positive material and getting in touch with my sexuality, such as it is. I don’t think I’m asexual, because I masturbate with a vibrator once a week or so and do enjoy sex from time to time. I’ve only had three partners, all in long-term relationships, and have been married for eight years. My husband would like to have a lot more physical affection than we currently have—not just sex, but also fondling, cuddling, etc. I don’t think my disinterest in sex is because of him, because he’s a very attentive lover, and I’ve never been all that into sex even with previous partners. It’s so much work for not much payoff, in my experience! I just don’t experience a lot of fulfillment or satisfaction from sex and rarely crave it, except in special moments like reuniting after a separation or other times of emotional closeness. I feel guilty because I know my husband’s physical needs aren’t being met and it’s hard on him. I would fake it, but faking it feels wrong, because he wants the intimacy and emotional connection, and he’s trying to kiss me and gaze into my eyes while I’m mentally composing my grocery list. Should I talk to a sex therapist about this? Is it even something I can reasonably expect to improve on?
— Not Feeling It
Dear Not Feeling It,
There are absolutely ways to improve the erotic connection with a mate. Ian Kerner’s So Tell Me About the Last Time You Had Sex lays out several, including guidance for psychological stimulation. His rationale goes: “There are two powerful pathways for creating arousal—the physical and the psychogenic—and if you’re only using one channel, then at best you’re only using 50 percent of your capacity for arousal.” The two categories of psychological stimulation he explores are face-to-face (things like sharing a fantasy or watching a partner masturbate) and side-by-side (reading erotica together or watching porn with a partner). Does any of this sound remotely appealing or even feasible? It’s OK if the answer is no, it just makes everyone’s jobs a little more complicated.
The thing is, you have determined you are not asexual using uninformed criteria. It may seem counterintuitive, but asexual people masturbate and enjoy sex. Typically, what is considered to divide allosexuals from asexuals is desire or lust; the former have it, the latter don’t. There are plenty of reasons for enjoying sex without said desire (for release, for example), but if you aren’t experiencing desire for other people (or, in the case of objectum sexuals, objects), you may be asexual. Reading Angela Chen’s Ace may open your eyes to your own experience, or it may help you clarify why you aren’t ace. It’s worthwhile, either way. In any event, what do you want to do about your husband if you determine that sex will likely remain a rarity? Is it fair to ask him to go at your pace? Do you want to consider allowing him alternate outlets for his own desire? You will, in all likelihood, have to confront this issue. Better to get in front of it now than have it sneak up from behind later.
More How to Do It
My husband and I have been married for more than 25 years and have had what I consider a great marriage overall. Couple of kids, couple of cats, house, etc. Nothing out of the ordinary. And that (nothing out of the ordinary) largely describes our sex life too. It’s been kind and loving, but not particularly kinky. My husband has always been aware he’s not particularly well endowed—but recently that’s, uh changed.