How to Do It

I Had Sex With a Woman Online. Now a Blackmailer Wants $2,000 for the Video.

A man looks stressed on his laptop while dollar bills flash next to him.
Photo illustration by Slate. Photos by 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 a 55-year-old single straight man. I have a partner of several years (same age), but because of COVID-19 and our situation—we live in different homes, I have kids, she doesn’t—we are in different bubbles. We do walks and talk in person, but no physical contact. She is not into online sex between us, and I am OK with that.

So with the lockdown, I discovered online live adult entertainment on a cam site. It is fun, but expensive. Mostly I watch and chat, but it got kind of hot and heavy with one particular person online. Let’s say that what took place on either end, while pretty vanilla, would not be fare for PBS. There was also one private session. I should add that my partner is not aware of these recent online activities, and would probably be really pissed if she found out.

To get to the point: A couple of days ago, I got an attempted extortion letter. (I will send it to you separately.) The summary is that the person claims to have a recording of what took place, at least at my end, and wants $2,000 in Bitcoin to destroy the evidence. The extortionist says they have access to my emails and other contacts and will send the video out to my contacts if I do not pay. It is clear from the letter that they really do have more information about me than I would like.

It would be quite embarrassing for this to get around, but I have no intention of paying. Any suggestions about what to do? A quick look at the FBI website had me confused—it looks at first glance like you need to have lost money first before they will look at the case.

—Candid Camera

Dear Candid Camera,

Unfortunately, I cannot provide you with a cure-all. No matter what you do, you could still be screwed. This I gathered during a conversation I had with a lawyer who has handled extortion cases (and who asked to remain anonymous). While the call is yours to make, and while the outcome is entirely uncertain, you’re probably best off not paying the $2,000, contacting local authorities (not the FBI, which would probably be hard to persuade to take on a case involving just $2,000), and retaining a lawyer. That lawyer may cost you well more than the $2,000 the extortionist is asking for. But there’s no guarantee that this person will stop asking for money just because they receive a payment, and there’s no certainty that the recording that you wish to suppress will remain unreleased, anyway. There are lawyers out there who are extremely vigilant about stopping extortion, even arranging meetings with the would-be extortionist and putting wires on their clients. At the very least, legal counsel could help you strategize. You could also attempt to contact the site from which the footage was recorded, though what’s particularly tough here is that you have no idea who or where the person trying to extort you is. It could be someone involved with the site or a hacker.

This sucks and your distress is palpable. While your anxiety might complicate (if not render impossible) what I’m about to suggest, I still think it’s worth considering: This person’s power over you exists in direct relation to your shame over the stolen footage of you. I’m not trying to write off your extortionist’s illegal and immoral behavior, but coming to terms with the possibility of the release of such footage might buy you some peace of mind. Would your life change drastically? Would you lose work or respect? There’s an online initiative called Post Shame that encourages people to come to terms with sensitive material they feel may leak by posting it themselves, effectively reclaiming that which could be exploited and rendering it unexploitable. I’m not telling you to leak your own jerk-off video—it does not sound like that would be a great option for you—but at the very least, reading accounts on the Post Shame site may be useful for coping and preparing for a worst-case scenario. You have no obligation to just get over this, but attempting to do so may help. Good luck.

Update, May 12, 3:31 p.m.: Several readers wrote in to note that you may be experiencing a blackmail scam that has become pervasive in recent weeks. You can read about it more at the Federal Trade Commission or in a series of Reddit threads that have documented the scam. These scammers often do have some personal information, like a password, and use that to fool people into believing they have more. This sounds a lot like what you describe. And if that’s the case, here is the FTC’s advice: “The scammers may say they have access to your computer or webcam, or installed clever software to defeat you. That’s all talk. But they may really know one of your old—or recent—passwords, and they include it in the message to prove it. When you see that, you know it’s time to update your password on that account, and consider updating other passwords, too.”

Dear How to Do It,

How will I know when it’s OK to hook up again? I am a single person who had been dating and had a couple casual sex partners before this all began, and one of them has started sniffing around as conditions have improved in my area. But I’m wondering, literally, how will I know when this is OK again? When my state’s governor lifts shelter-in-place orders? When I can get a haircut? When my office reopens? I don’t get how I’m supposed to know, and I kind of want to take up this offer.

—Tipping Point

Dear Tipping Point

All that I’ve read suggests that we can’t really drop social distancing en masse and get back to “normal” until we have a COVID-19 vaccine, effective treatment, and mass testing. That could be a while. The best way to determine whether these things are in place is to follow the news, which is how we found out that the sort of causal contact we’ve been accustomed to, including hooking up, is no longer OK. Keep listening to the latest best practices and medical developments. I’m not sure where you are, but several reports (like this one) suggest that current efforts to reopen states in the U.S. are premature and may result in an uptick in infections, so I don’t think the lifting of shelter-in-place orders or the ability to get a haircut should be your guiding light. At some point, the facts about infection rates may change, and you can reassess then.

So I wouldn’t advise taking this person up on their offer, but I understand the toll of loneliness and impatience. Everyone is in coping mode, but I wonder how satisfying this taboo hookup would actually be. If you were to break social distancing for this partner, what if it were underwhelming? Would you be content to take that one on the chin, or would you search for a more satisfying reason to break social distancing? Say it were good: You did it with one person, what’s another? Sometimes all it takes is the violation of one restriction to eradicate them all, a crack that breaks the dam. Annoying and sucky as it is, for now, self-quarantining is our civic duty. Do your best to do your part.

Dear How to Do It,

I am a 33-year-old trans man who is pre … everything, really. I am out and I present male in my day-to-day life as well as I can, but I am still working through a difficult insurance situation and have not yet started hormones, and surgery is little more than a speck on the horizon. I want to find a romantic partner, and dating apps seem like an easy way to filter for people who are trans-friendly. However, I consistently run into a major problem: Nearly every app I have tried will let me identify myself as a trans man, but will then have me fill out a question saying “Show me to people who are interested in…” with “men” and “women” as the only possible answers. I don’t know how to answer that! I am not a woman and have zero interest in misgendering myself, but at the same time, people who are looking for men are generally not looking for bodies like mine. The only app that did not ask me this question had other drawbacks that made it functionally unusable for me. How do I best and most honestly present myself, or do I just give up on apps until I am farther into a medical transition?


Dear M4?,

You’re a man, so your profile should be seen by people who are interested in men. Anyone you would want to connect with would consider trans men to be men, right? By choosing that option, you are availing yourself to that population. Like all men, you will not appeal to everyone. That’s part of dating, though you should be careful on apps, because I’ve heard many stories about people being especially unkind to trans people. It may get to be too much.

It’s rather compassionate of you to consider how people will relate to your equipment, and there are no set rules for the right time and manner to disclose the state of said equipment, but if you’re identifying yourself as trans in your profile anyway, those serious about wanting to get to know you should get the gist of where you are in your transition. I’m not sure who you’re interested in dating, but if it’s men, apps like Grindr and Scruff have a visible trans man population. If you’re looking for women, you could try an app like Lex, which caters to queer women but is also (reportedly) inclusive to trans men. OkCupid has features that help make it more trans-friendly.

The most important thing to do is to take it slow and know that as connected as technology can allow us to be, distance empowers people to say unkind things to others. Many people have disappointing experiences on apps, regardless of their gender identities. I hope you have good experiences and make an effort not to take the bad ones personally.

Dear How to Do It,

I’m a teenager. I have been living in my grandparents’ house from childhood until now because it worked better for our family. During the coronavirus, I have to live with my parents and brother. It is OK but for one thing: Both my elder brother, who is 23, and my father, who is 50, sleep naked, and they aren’t shy about walking around naked too. I got dressed one night to go to the bathroom, and my elder brother teased me. My mother lives here too. I am not comfortable being nude in front of anyone. I am shy. Once you hit puberty, isn’t it better not to be nude in front of your parents? How should I discuss this with my parents and overcome it?

—Cover Up

Dear Cover Up,

You should stand your ground and continue to refrain from doing anything you aren’t comfortable with. Your comfort level should also be informing your family members’ nudity around you—the party line on this issue is that if this nudity is nonsexual and everyone is comfortable with it, there isn’t a problem. I get the feeling that you’re not exactly comfortable with your father’s and brother’s tendency to walk around naked. You should speak up about it and your own shyness, if you can, and you can show them articles on the issue like this one if they don’t take your feelings seriously.

Not being taken seriously is a risk. In some families, ridicule is the risk you take by opening your mouth. Your older brother is giving you shit because that’s what older brothers do. You are under no obligation to do anything with your body—including exposing it—that you don’t want to. You have every right to your privacy. I don’t think there is anything to overcome here. Your feelings on the matter are valid as is, and should be respected as such.


More How to Do It

I’m a 39-year-old woman. When I was 20, I met my first very well-endowed man, who in a way “trained” me to take a large penis. Since then, I’ve been in two monogamous long-term relationships, both with average-size men. I hate to admit this, but I left both those relationships because the length just didn’t cut it for me. I needed more. I’m great at taking it, and it’s the most satisfying way for me to come. I’m still out there dating. My question is, how do I put it out there in the online dating world that anything less than a hard 8 inches will only disappoint me?