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. Dear How to Do It,
I’m a woman in my early 30s. I sometimes enjoy not wearing a bra in public (never in work settings, and nothing completely see-through, and my breasts are relatively small). I like both the possibility of somebody seeing my nipples through my shirt and the constant but minimal stimulation whatever shirt I’m wearing provides. Recently, on a solo road trip, I had the desire to pull my shirt up and expose my breasts while driving on the highway. I liked that somebody might see me, but realized that the chances of that happening were pretty minimal. Even though it was thrilling, I feel conflicted because I know if someone saw it could make them feel uncomfortable or violated. I’ve only done it the one time, but is this something I need to retire?
Dear the Flash,
If all things were equal, this wouldn’t be a question and we’d all take for granted topless women in public as we do topless men—just part of our cultural wallpaper. That all nipples are not free just goes to show how contrived our taboos can be. I wonder, though, if you’d be so prone to jiggling with the wind if, in fact, topless women were commonplace in our society. In other words, what’s the thrill here: Is it the simple act of being topless in public, or is it the transgression of social mores that results from being topless in public? It doesn’t have to be either/or, but reading your letter, I wonder if you’re leaning heavily on the latter. A potential lookie-loo may be turned on by your free-flapping sensibilities but also may be made uncomfortable—the excitement lies in that uncertainty, no? At the very least, the possibility of someone’s discomfort comes with the package, although one could reasonably argue that being made uncomfortable by a topless woman is a lack of maturity that is on the uncomfortable person to get over, not the woman who is frolicking unbound.
I guess I feel conflicted here, too, and I really want you to evaluate your motivation. I don’t want to impose on you and your breasts—I am not a bra and, to the first part of your letter, I don’t think you’re under any obligation to wear one—so I ultimately advocate that you be as free as you feel you should be. Try safe/consensual environments like nude beaches or even nudist spaces, where everyone there knows what they’re signing up for. At the very least, it would allow you to test the real source of your thrill and stay (I’m doing it, you can’t stop me) abreast of the morality of how you express your kink.
Dear How to Do It,
Both my wife and I were quite … adventurous before we found each other, albeit her even more so than me. I have somewhat recently discovered that I LOVE (that’s right, all caps) hearing about her previous conquests in pretty explicit detail: What they looked like, how they met, what they did together, how well-endowed he was, etc. My wife has been more than willing to indulge this burgeoning kink, but I want to make sure not to cross any lines. How common is this kink? Any tips or recommendations?
Congratulations, you’re much more laid back about your wife’s sexual history than what we’re conditioned to believe most men are or should be through the enduring stereotype of the jealous boyfriend. Isn’t it unfortunate that people need to pretend their partner’s sex life started with them, even though they know it’s almost never true and probably couldn’t even explain why they need that to be true? Your acknowledgment of reality qualifies you as progressive, never mind that you enjoy contemplating your wife’s sexual history.
I don’t have a spreadsheet or anything, but as a kink, I’d say this is among the most common. You’re so enthused that it sounds like you’re getting into, or are otherwise just mildly intrigued by, something approaching cuckolding. The great thing about this kink is that it’s based in communication. So keep talking and if anything, push even further. Your “quite adventurous” days don’t have to be in the past. Explore. Are you actually interested in watching your wife have sex with another guy? You could suggest it. Or you could discuss and try group sex. And then discuss it some more. Or maybe you guys would be into more scene-based dabbling and would enjoy swinging. Whatever! I see this as entirely healthy as long as your connection remains strong with your wife independent of her past—that is to say, keep yourself in check and make sure she’s still the centerpiece of your attraction, not her stories. You guys sound fun, so keep it up. Let your open mind take you on an adventure.
What do you want? A homemade vinegar-and-baking-soda volcano that she times to erupt with your ejaculation?
Dear How to Do It,
I’m happily married to my wife of 10 years. Our sex life is wonderful, and I love her more than anything. I know she feels the same way. But as a fortysomething male, my sex drive is stronger than hers is in her mid-30s. If I don’t ask for or mention oral sex, she doesn’t offer it or give it—ever. At this point, I’m used to it, but it obviously bothers me. I’ve mentioned it in our time together, but she hasn’t adjusted. When she gives it, she seems to be OK but doesn’t bring me to orgasm without her hand or just jumping on top of me for intercourse. Is this normal? My hygiene and manicuring are impeccable. I’m circumcised as well. Should I just be understanding, or is it something I’m not considering?
You’re getting blow jobs from someone who’d rather not, and you’re still not satisfied? What else do you want? Her to tap dance when you come? A homemade vinegar-and-baking-soda volcano that she times to erupt with your ejaculation as part of a larger performance art piece?
I’m messing with you, but look: I feel you. Getting head is amazing, and getting head from someone who loves to give it is phenomenal. The cards just didn’t fall that way for you. And really, I think your wife giving you blow jobs despite her apparent lack of enthusiasm for them is a pretty good deal. She seems awesome. She’s doing enough. You could tell her exactly what you told me—that you want her to want to do this—but it doesn’t sound like that’s helped much in the past. If this is really so important to you, you could also talk about opening things up, but is it worth messing with a sex life that you describe as “wonderful” for the sake of enhancing one facet? I doubt it. Proceed with caution. Be happy with what you have.
By the way, are you giving her head? I assume that you are, and I hope that you approach it like it’s what you were put on earth to do. If you put out what you want in return, you never know what you’ll get back.
Dear How to Do It,
I’m a bisexual trans man in my 20s. I’ve been on hormones for more than a year and had top surgery three months ago. I’m in a long-term romantically exclusive but sexually open relationship with another trans man, and the rest of my partners have either been women or nonbinary. I’ve never slept with anyone with a dick, and I want to so badly. I’ve spent my entire life knowing and mourning the fact that I’ll never experience gay male sexual culture like cis men do. Recently, I considered going on Grindr, but I’ve heard horror stories from trans men who pass much better than I do. I look small and skinny, but under all my clothes, my body is jiggly, unattractively feminine, and riddled with cellulite. I feel like no cis gay man could look at my body and feel desire. I also have no experience with dicks, so I’d probably suck (ha-ha) at giving head.
Adding onto that is the fact that anal hurts me a lot, and I would never be able to bottom in the way cis dudes would want me to (and topping a cis dude is out of the question—I’m tiny and no one wants a prosthetic dick). I would only be able to use the front hole, and I know how gay men are about vaginas. Plus, there’s the fact that, after a decade of antidepressants, I am much less sensitive than others, and often need an inconvenient vibrator on my dick to get off. Put all of this together, and you’ve got one entirely undesirable dude. I’m not attractive naked, I can’t do butt stuff, I don’t have a real dick to take dick pics, I look like a girl under everything, and I can’t even have a normal orgasm. There are too many inconvenient variables for any guy to be interested, even besides the very obvious trans thing. Is it so wrong for me to want the same experiences as other men? Should I just give up? What else can I do? How can I even get any experience with cis men if none of them will ever want me?
Dear Not It,
Please don’t give up before you’ve even started. Please do try to change your attitude. You told me several times how unappealing you are, effectively subverting you own cause. Get out of your own way. Confidence and the overall way a guy carries himself play a huge role in his attractiveness, and this is a perfect venue for a fake-it-till-you-make-it approach. (False confidence, in fact, is effectively real confidence. Get good at it and no one will spot the difference anyway.)
Look, you’re going to deal with small-minded guys on apps. Shitty men are everywhere. It’s not necessarily going to be a nice time for you on an app, because it isn’t for most guys. Sometimes you really have to search for someone that is both attracted to you and worthy of your time. You may be right that you have a more complicated experience than most ahead, but I also think that people’s minds are expanding, that their understanding of gender and sexuality is sharpening, and that there’s no reason to assume that you won’t find someone who’s into you, cellulite and all. There are gay men who act like shrieking latency-period children around vaginas, and there are those who don’t. There are guys who only want to drive in the cis lane, and there are guys who are pansexual and attracted to people regardless of gender identity. The world is changing, and you get to witness that change firsthand. I understand why you are daunted, but I also think that if you adjust your eyes, you could see that this is also potentially exciting.
As for the other particulars you mention, you are not one entirely undesirable dude. You’re just a dude with idiosyncrasies like the rest of them. Please don’t beat yourself up about who you are or what it takes for you to come.
I think you should be upfront with who you are, what you’re looking for, and, to whatever degree you can stand it, what you’re working with. That way there are no surprises when you meet a guy in person. While I think that sex parties are rather advanced forums, they are an option if you want to go that route—New York, for example, has a number of them that I’m aware of that cater to a trans clientele and where you’d be welcomed and likely have the option to get laid several times over in a night/afternoon if you were up for it. You can also find queer spaces and meet potential partners face to face—that almost always leads to the best sex in my experience.
Your letter bummed me out so much that I asked my friend Riley MacLeod, who’s trans and gay and also an editor at the gaming site Kotaku, if he could share some life experience to help clear out your cobwebs and sorrow. Riley has been out as trans for nearly 20 years, during which time he says he’s seen “huge shifts in cis gay men’s understanding of trans men.” If you’re looking for a jumping off point, he shared that exploring BDSM and leather early in his transition was a great way “for me to be sexual with other men while having a built-in space to navigate boundaries around how undressed I wanted to be or where I wanted to be touched.” Finally, he says don’t fear the front hole: “Speaking hugely for myself, a lot of cis men I’ve been with are pretty into using the front hole—there can be a bit of a learning curve for some guys, but I’m personally a fan of it, and many of my cis gay partners have been too. Overall I totally get feeling down about your body when it’s different from ‘most’ men’s, but I am 100 percent sure there are tons of guys who would be happy to be with you.”
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I Get a Thrill Out of Exposing My Breasts While Driving. Is That Wrong?