How to Do It is Slate’s sex advice column. Send your questions for Stoya and Rich to firstname.lastname@example.org. Nothing’s too small (or big).
Dear How to Do It,
I am a cisgender male who is attracted to people who are female-presenting despite their pronouns, sexuality, or genitalia. That last thing bothers me because I have read online about “trans chasers” in passing, and it seems the rule of thumb is not to specifically date or have sex with someone just because they’re transgender. I have had sex with one transgender woman (no bottom surgery) and I really enjoyed it. I’m a top so I am not getting anything new except that my partner has a dick I can play with. Whenever I masturbate, there are usually a few videos or cams of transgender women (no bottom surgery) included with whatever else I watch. Long question short, am I fetishizing or being a trans chaser by dating/having sex with/watching porn of pre-op transgender women in addition to cisgender women?
Dear Cis Kiss,
Here is a good rule of thumb for dealing with all people, regardless of sexuality and gender expression/identity: Don’t be a dick. And here’s another: Treat them like people. A few years ago for Slate, Christin Scarlett Milloy qualified the difference between cis people who admire trans people and cis people who are trans chasers. The chaser “really, really, really wants to ‘be with’ a trans person, one with original anatomy intact,” she wrote, “to the extent that other interpersonal concerns are neglected and ignored.” The chaser prioritizes the trans over the person; the admirer prioritizes humanity.
Your letter is encouraging in the respect that you have to some degree internalized that trans women are women. This is a simple concept that cis men struggle with nonetheless. While it’s important to be sensitive of the way our culture has historically treated and continues to treat marginalized groups, it’s also crucial to refrain from othering members of those groups. It’s a delicate balance, that whole sensitivity thing. A friend of mine who is trans said she’s noticed narratives out there that “make men feel like creeps for being into us,” which is absurd. This is a wokeness trap—so much consideration and concern that it becomes paralyzing and self-defeating.
I shared your question with my friend, and she surmised that you had the wherewithal to educate yourself on trans women and then became “ terrified he’s one of the bad men and is now so worried about being bad to trans women that he’s separating us from the other women he fetishizes regularly and seems to understand is not a problem.” Because, let’s face it: There’s a degree of objectification in all porn consumption and most casual sex. “If you’re just having casual sex with people, it almost doesn’t even matter if you’re a chaser or not,” is how my friend put it. “We’re all chasers for the people we’re having casual sex with. We’re all objectifying each other.”
She says trans women tend to be aware of the red flags and can spot a chaser a mile away. Regarding arrangements that endure beyond one-time hookups—friends with benefits, romantic relationships—she said that acknowledging a person’s interiority and subjectivity is a surefire way to avoid the pitfalls of chaserdom. “If you understand those things, it’d be pretty hard for you to be a chaser because then you’re not just after this thing with tits and [a] cock,” she said.
In short, she thinks you’re probably fine. “He just needs to chill out,” she said. I agree.
Dear How to Do It,
I’m an attractive woman in her early 30s who really wants to have a threesome with two other men, with them focused entirely on me. This has been on my mind a long time, but I’ve been in mostly monogamous relationships and, for various reasons, didn’t want to bring this fantasy into those spaces. I’m happy to do this with two unattached partners, but I’m not sure how to approach finding them, or communicating with them about exactly I want—or even if it’s too demanding or selfish to request exactly what I want. I’ve tried to find poly men on apps like FetLife, but I’ve mostly found them to be flaky or not what I’m looking for. I could also afford to pay two men for this, and have considered that, but I have no idea where to start finding or vetting male sex workers. Part of me wants to just go to a bar and point at two dudes, but as a smaller woman, that seems risky and like my boundaries too easily wouldn’t be respected. How should I go about this? And if I did want to hire someone, how’s that work?
—Two for One
Dear Two for One,
Have you looked into swingers’ clubs/organizations? I think that’d be your best bet—the general objective of everyone in the room is to bone, and you’d get to see the goods in motion and check out whether you vibe with a potential partner (apps don’t transmit these things particularly well). A lot of the guys in those spaces would have no problem sharing a partner with another guy; it generally comes with the territory. And, as an attractive single woman, you’d be welcomed with open arms, among body parts.
If that is not your scene, though, you could try any number of online male escort agencies simply by Googling “straight male escorts.” Cowboys4Angels is one such agency that caters to straight women and has gotten a lot of press. Not being a straight woman, I can’t vouch for the quality of its service, but a woman named Heather Smith who was, at least at one point, a frequent patron of the service said, “Best therapy ever!” when interviewed about it on Nightline. (Some fine print on the C4A website: “Cowboys 4 Angels does not contract for sexual services and we are never compensated for sexual services.”)
There are also other apps out there besides FetLife (like Feeld and 3Somer), though as with all apps, you’re likely to encounter flakes and/or people you aren’t into. That’s life. I encourage pickiness. Its benefits outweigh its drawbacks, as anyone who’s been in a threesome that has ended in an argument or tears will have you know. I could tell you horror stories that I’ve amassed while learning to be picky the slow, hard way. Keep looking, openly but carefully, and you’ll find your guys.
Dear How to Do It,
I’m a 25-year-old woman who happens to be a virgin. I grew up in a fundamentalist area where the men I dated practiced abstinence, so being pressured for sex wasn’t something I had to worry about in high school. I spent all of college studying (to an unhealthy extent) and didn’t pursue relationships during that time. Now, as an adult, I’m finding that sex is something most people expect in relationships. I feel both behind the curve—I’ve literally never seen a penis—and afraid of sex with another person in general. I’ve had plenty of self-administered orgasms and enjoy them, but getting another person involved seems like … a lot of mess and trouble, honestly. Is something wrong with me? I feel broken compared to everyone who seems to really want to bone.
Dear Big V,
There’s nothing wrong with you, and you’re right about at least one thing: Sometimes getting another person involved in your sex life is a lot of mess and trouble. If I had a jelly bean for every underwhelming hookup that made me think, “I would have been better off just masturbating,” I’d have so many jelly beans I’d have no choice but to keep them in my tub, and then I’d never leave the house. (I wouldn’t really be able to bathe for one thing.)
You’re not broken, but you might be on the asexuality continuum. Then there are people who just really like to masturbate. That’s their thing, and that’s all they need. You might also be swept up in the fear of the unknown; sometimes all it takes to get into sex is some sex. The longer you go without sex, the more likely you are to get anxious about not yet having had it. Once you do indulge, you may find that one time was all you needed to prove to yourself that you could do it. Or you may find that once is enough. There’s no correct outcome—the sooner you stop comparing yourself to other people and their expressed desires, the better off you will be. Life’s too short to be chasing someone else’s idea of pleasure. It seems like not having sex is what’s making you most comfortable now, but perhaps at some point, you’ll be so uncomfortable with the comfort you take in not having sex that you’ll want to venture out. By all means, give it a whirl. Go on some dates; talk to some guys. Remember that you don’t necessarily have to have intercourse to have fulfilling sex with someone. If you’re into self-administering orgasms, perhaps you could start with mutual masturbation. Even if your journey takes you right back to where you started, the knowledge you gain about yourself in the process will likely provide comfort.
Dear How to Do It,
I am a thirtysomething gay male in a monogamous marriage with my husband and partner of seven years. Things between us are generally great, and our relationship has never been stronger. We get along, I find him wildly attractive, he’s really good in bed. The only thing that could be better is penetrative sex.
And that’s totally on me. He’s mostly a top; I’m mostly a bottom. We’ve tried it other ways, and we’re both open and willing to flip our roles when someone wants to. But honestly, we both just gravitate toward those positions. The problem is that it feels like sometimes my butt just won’t cooperate. I can’t relax it half the time, so it feels tight. I also seem to be particular sensitive (in a bad way) to certain positions. Other times I feel like it’s just going to be too messy of a situation, even though I do all the things they say to do to help there. I know butt play is inherently not clean, but it still bothers me. Overall, sometimes I get so in my head about bottoming that we’ll go weeks without doing it. In the interim, we’ll do other things, so it’s not terrible. But I want to bottom more! Any advice on how I can power through to power bottom?
Dear Bottom Out,
Let’s break it down point by point: You can’t relax half of the time, so relax. This is not always something that comes naturally (people often reflexively tense up when penetrated), and so you must concentrate on relaxing. It sounds paradoxical, and maybe it is, but if you put your focus into relaxing, you may find that your body follows suit. Repeat to yourself that you are relaxing, breathe, and really focus on making sure your butt is as open as possible. Practice on your own with a finger or small toy; just try to relax on command, nothing else. It can be a huge task—anyone who thinks the top does all the work hasn’t had very much butt sex.
If you’re sensitive to certain positions, don’t use those positions. Use the ones that feel good. The goal is to actively and mindfully maximize your pleasure. Avoid that which you don’t enjoy.
As far as the messiness goes, it’s inevitable sometimes but can greatly be curbed by taking psyllium husk regularly and perhaps even altering your diet when you know you are going to bottom (curb grease, junk food, spicy food, and even coffee). Most mature guys who top know about the possibility of poop. Comes with the territory. If your husband is not particularly squeamish about this, it’s your issue to get over. Our culture hits us over the head with messages of cleanliness that, combined with the taboo nature of gay sex, can make anal a minefield of shame. It’s not surprising that you feel the way that you do, and the real kick in the ass is that it sometimes takes real effort—like the kind that demands time out of your day—to move past it. I promise you, though, it’s well worth it.
More Advice From Slate
My husband and I were married for nearly a year. A past friend came into my life, and we went out for drinks. He and I ended up sleeping together that night. Ever since, I have been guilt-ridden. I will not ever let it happen again, I have not seen this friend again, and I even told him that I felt such guilt that I can’t talk to him any longer. My husband is a wonderful man who is attentive, sweet, and an all-around great person to be with. My motives for cheating? Frankly, there are none. There were times just before the “one night stand” took place where I did feel lonely. Not for lack of lovemaking, because we are pretty into being together. But we have children, children who, like any other, demand our time. My husband works more than one job and helps tend to the kids, and at times I am not only bored, and lonely, but I also feel like I don’t have any personal time with him. Someone else spending personal time with me … it made me feel wanted. I know this is wrong. Trust me, my guilt has me totally consumed. I plan on telling my husband the truth, because he deserves that. I’m hoping to save my marriage, because I know what a big mistake I have made, and I love my husband more than anything. My questions are: How do I bring it up? And how do I let him know that I am so sorry for what I have done? I feel like the worst person in the world.