How to Do It

Do I Get a Say in How My Sugar Baby Markets Her Sex Work Online?

Older man on a computer looking over his shoulder at a neon pink dollar sign.
Photo illustration by Slate. Photo by Sanja Radin/iStock/Getty Images Plus.

How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!

Dear How to Do It,

I am the ongoing client of a high-end, low-volume, professional escort. I first met with her when she was an undergraduate at an Ivy League college; she is now in a prestigious graduate school while working at a research firm where she’s been quickly promoted. Over the three years I’ve known her, she’s shared her real name and much of her background. (I’ve helped her with her real-life LinkedIn profile, for instance.) She comes from an underprivileged home, with an absent convict father, and climbed her way up with grit and raw intelligence. I respect her more than almost anyone I’ve ever met, and if I were 30 years younger, I’d be crazy in love with her. We are now FWB and one of the benefits for her is that I give her money. By the time she completes schooling she’ll be $200,000 in debt, so doing sex work is a reasonable way to survive and pay down some of that debt. Here’s the problem: When she left for graduate school, she changed her working name and posted a Twitter and profile that clearly show her face, which she’d previously kept blurred. Because I know her screener, I know she gets very little traffic from either of these sites, gets all her clients from referrals, and, in fact, is very low volume, which is not surprising considering she works a full-time regular job and goes to school full time. Both her screener and I have suggested she remove those accounts, but she won’t because she’s convinced if she gets outed nobody would care. I think she is taking a horrible, unnecessary risk that could torpedo a promising career. I try not to give advice when it’s not been asked, but knowing that this sword of Damocles is hanging over her head is driving me crazy. She won’t listen to me; maybe she’d listen to you?

—Scared Sugar Daddy

Dear Scared Sugar Daddy,

I appreciate your faith in my power to reach hearts and change minds, but I’ll have no part in your patriarchy. You’re this person’s client, not her manager. Think about what would happen if you went into a Louis Vuitton store (or, depending on your preferred price point, Zara) and said: “I love your stuff, but your most recent ad campaign was terrible. Here’s how to fix it …” You’d be ignored, if not laughed out of the store. Same principle applies: Know your place. You’re the consumer.

By being so open about her identity and her escorting, she may be making a decision now that will complicate her life later. It also may have zero impact. Both possibilities exist in the realm of hypothesis, and since no one can predict the future, a fair directive is impossible. What’s real and true at this moment, however, is her agency. People have to be able to make their own mistakes. In any event, it seems unlikely that the road she’s on, from Ivy League to prestigious graduate school, will lead to destitution. It’s safe to assume that she will be fine. Maybe not the fine she wants to be, but fine all the same, and it will be a product of the choices she made. Don’t overstep—her business is none of yours.

Dear How to Do It,

My fiancé and I met in the summer of 2019. The first night together we talked openly about our past relationships as well as other getting-to-know-you stuff. We discussed we had some BDSM and nonmonogamy experiences in past relationships.

It became very apparent from his clear and nonemotional descriptions that his wife was emotionally abusive. He blamed himself because some of the events that led to this were his idea. Think: Opening up the marriage led to him being berated for having a small penis (he doesn’t) and not being able to satisfy her (he satisfies me just fine). It finally reached a breaking point a few years ago, he left, and she has since died. The only relationship he had after that sounded like more of the same, in that he chose a woman who didn’t think he was good enough for her. I had also just recently gotten out of a tumultuous relationship but feel like I was in a pretty good place after that. He has done counseling, and we are big on communication in our relationship.

Here is where I need help. He cannot believe that I am satisfied in our relationship sexually or otherwise. And he apologizes all the time for things he shouldn’t apologize for. I love this man like crazy. I love his hobbies, his interests, his politics (even if we don’t always agree), and, more than anything, the way his eyes light up when he gets excited by something. Anything. Please wax poetic about skateboards, video games, or buying a smoker for meats. Let’s talk about that book you love and that movie not being as good as the book. Don’t apologize for being happy about something! He lacks confidence. And sometimes I find it frustrating. How do I build him up?

—Yes It Was Good for Me

Dear Yes It Was Good for Me,

Just keep at it. While this process is understandably frustrating, I would avoid expressing that frustration to any detailed degree. Ideally, you’re providing your fiancé with a model for what a relationship could be in contrast with the mistreatment he’s experienced in the past. Because you can recognize the marks of emotional abuse, you can see them for what they are and hopefully tolerate them. I’d recommend absorbing 80 or 90 percent of his apologies with intermittent reminders that he doesn’t have anything to be sorry for. Lavish him with compliments regularly and randomly. Initiate conversations so as to hear him speak about the subjects you’re interested in. Encourage him to do things that he’s good at. Show him how much you enjoy his not-small penis and what he does with it. Build him up.

From your brief description, it sounds like you’re the more emotionally mature and aware party, which means that you may have to assume the lead here. It’s a responsibility that may feel like a burden, but if you have the patience, I implore you to take it on. (It shouldn’t be too, too hard since you love him like crazy.) The ability to help someone construct his confidence over time is a beautiful thing to experience. Being good to him will be good for you.

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Dear How to Do It,

I’m a 34-year-old man living with kidney failure and have been in dialysis for two years. Transplant is in the future, but waiting lists are long, so I am training in the art of patience and currently occupy the level of master.

One of the side effects is problems with getting or maintaining an erection. I’ve had three women break up with me soon after initiating sex because of this. They either think I’m not into them or simply say they didn’t feel any sexual chemistry. I want to find a partner, and I’m not willing to throw in the towel. But it’s gotten to the point that I’m afraid to initiate sex with a new partner because I’m afraid of having this happen to me.

This doesn’t occur with me 100 percent of the time. I would say maybe 40 percent. But still. It’s embarrassing no matter how understanding people say they are. This also occurs when I’m by myself. I have had some success with pills but have also been unable to get hard like I used to after taking them.

The emotional toll this has taken is significant, and I pine for the days in which I could have sex all day if I wanted to. At 34 it’s pretty depressing, and I find myself wanting to find a woman who will be patient and not be put off by this. But alas, I find myself not being able to find this person. As a psychologist, I’ve tried a number of ways to cope, which are mildly successful but mostly just Band-Aids. My success with some erections leads me to think that most of this is in my head, that I’ve perceived myself as someone who is sick and disabled and so my penis not working properly became part of the narrative.

I’d like to know what you think, if you’ve had experience with this, and what might I do on my own or with a partner to overcome this. The terrible rub of all this is that my libido is still as strong as it was prior to my illness.


Dear Daydreamer,

Erectile dysfunction is common in people experiencing renal failure—this study cites data estimating that 50 to 80 percent of patients with chronic kidney disease experience ED. There is some (contested) evidence that, because patients with CKD tend to have reduced testosterone, testosterone replacement therapy could be useful: Have your doctor test you and consider moving forward with that if your levels are low. (Note: If your libido is high, your T is probably fine, but it still won’t hurt to check.) If standard ED drugs aren’t always doing the trick, you could try a pump or vacuum therapy, as it is called—the aforementioned study cites data that found over 73 percent of patients achieving erections with the use of a vacuum device.

You should scan that link for more ideas (as well as affirmation that for many men, erectile dysfunction improves post-transplant). In the meantime, you have a cross to bear. It sucks, but it’s your reality. I encourage you to talk to your partners in advance about your condition and its sexual side effects. At the very least you’ll be able to get in front of and refute the assumption that it’s your partner’s fault your dick doesn’t stand at attention when they enter the room. People are irrational, yes, but you have a preexisting condition, and it’s egocentric to the point of frightening for a person to take your illness personally. It’s tough to endure, but that behavior is a great indication that the person in front of you will not be an adequate partner.

Instead, I’d attempt to forge more emotional connections and focus on aspects of sex that aren’t dick-centered: making out and body contact, manual and oral. It might help to find a partner who is into playing with toys in the presence of a partner—a dildo’s perpetual stiffness could pick up some of your slack.

Finally, just hang in there. It’s going to get better for you, and it will do so sooner or later if you put out what you’re looking to receive. You say you want a partner who’s patient; some patience on your part will make life easier before that person comes your way.

Dear How to Do It,

I’m a gay trans guy who used to think he was asexual. I didn’t really like the idea of sex, never had any good sexual experiences despite having been in a handful of sexual relationships, and, honestly, became uncomfortable at the thought of genitals. Well, all this kind of changed when I ended up falling for a good friend of mine, but instead of some giddy-romantic crush feeling, all I could think about was fucking him. Which we ended up doing, and it was honestly amazing. Because of some unfortunate circumstances, we stopped having sex, but I still think of it quite a bit. The thing I’ve noticed is that I really enjoy thinking about his penis. I used to be almost disgusted with genitals, and I recently looked a bit into pornography to experiment around, but genitals still turn me off except if they remind me of that specific penis. Is that … normal? Can attraction be influenced by the other person’s genitals so heavily? Can you find one type of penis a lot more attractive than others? Or is it solely because of my attraction to the person attached to the penis? (Although that seems unlikely, as I was attracted to people beforehand but never liked the look of their genitals.)

—Gay Awakening

Dear Gay Awakening,

It seems you are, in layman’s terms, dickmatized. Some dicks just end up taking up way more real estate in your head than they do in any other part of your body. It’s certainly not abnormal to encounter a dick that leaves an impression, and plenty of people retain a strong connection to all manner of body parts. I don’t know if we’ll ever be able to chicken-or-egg your cock-a-doodle-swooning. You’ll have to figure out for yourself whether the dick makes you like the guy or the guy makes you like the dick; it seems at the very least that it will be a fun study.

I’m not trans, but I do know what it is to be different and worry about whether my interests are normal. It’s liberating to realize that “normal” is a myth and we all come to our interests in our own way. Maybe this particular dick is that extraordinary, or maybe it just came at the right time for you. It’s not wrong to like what you like, and you’ve effectively encountered a penis-shaped key to unlocking pleasure that you thought was out of your reach. What a wonderful thing. I think the most important thing to keep in mind moving forward is that even if you develop a strong attachment to and/or interest in penises, they’re still attached to humans and those humans need to be respected. If not, they may feel objectified and deny you the dick. So don’t get in your own way, but by all means, enjoy the dick.


More How to Do It

For the first time in my life, I am dating a person who is very overweight—clinically speaking, I think a doctor would probably call him obese. While I am very attracted to him and enjoy touching him and being with him sexually, I wouldn’t say I am attracted to how his body looks. I don’t think this is a problem for me—if it feels good and I want to do it, I’m set. However, since he is insecure about his weight and has received a lot of negative judgment from past partners, he frequently asks me for affirmation about his body. For instance, he’ll ask if I like different parts of his body, or if I think they’re sexy. I think he’s sexy as a full human, so I just answer yes to these questions and tell him he’s gorgeous. That’s the right thing to do, right?