How to Do It

I’m a Male Virgin, and I Have an Idea for How to Use My Stimulus Check …

I told my sister, and she’s furious.

A man looks on from some dollar bills.
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’m a 24-year-old male virgin. I’ve never been in a relationship beyond platonic or professional with a woman, largely because of a mixture of never really feeling the need for a romantic relationship, as well as social anxiety arising from Asperger’s syndrome. On a website I regularly browse (it begins with the number 4 and is associated with the Pepe the Frog meme), there was a thread the other day where other users were talking about using money from the stimulus checks for prostitution. After I saw that thread, I started considering it. I’m fully comfortable with my sexuality, yet the thought of having actual sex versus masturbating honestly has never been a priority or honestly desire of mine. When I brought this up to my older sister, who I’m extremely close with and have as a roommate in adult life, she was completely against it. She had three main reasons, which I admit are very valid: 1) The possibility of human trafficking being involved, 2) It would be a bad use of money in a very bad economy, 3) She thinks I have a unhealthy view of women that borders on gynophobia (I didn’t have the bravery to ask why she thinks this at the time). After that, however, she did say it was ultimately my decision, and if I did go through with it, she did want to know. I told her she had convinced me to not do it, but in reality, I’m still considering the prostitute. I honestly have no idea what to choose. Got any advice?

—Extra Cash

Dear Extra Cash,

As a rule of thumb, 4chan is not a great place to take social cues. That’s like learning how to take care of animals from Lena Dunham or Justin Bieber. Your sister knows you better than the strangers you may or may not interact with on a caustic forum, so I’d follow her lead. (You seem comfortable and willing to have this kind of conversation with your sister, so I won’t question that part here.) If you can stomach it, circle back and talk to her about the suspicions of gynophobia. As painful as it may be, this is a conversation worth having, as it could lead to you reevaluating how you perceive and treat women. And, to boot, the instruction would be coming from an expert source—your sister is, after all, a woman.

On principle, though, I don’t think there is anything morally wrong with hiring a sex worker. It might be illegal where you are, so take this as a hypothetical. On the trafficking question, I encourage you to read my co-columnist Stoya on sex work and exploitation—we often assume a lot about people in the profession. In terms of doing this during a likely global recession, you could file such a purchase under “self-care ephemera” along the lines of weed and video games. People on lockdown are smoking a lot of weed and playing a lot of video games, and I don’t see any social movements urging them to use their money more wisely. For many people who are effectively chained to their couches, the pursuit of happiness is lapsing into frivolity, which may speak to our flaws as a species, but that’s hardly a problem I’m going to solve in a sex advice column. It would, of course, be silly to spend on sex (which you do not need to survive) money that you absolutely need for food (which you do). When in doubt, let hunger pangs be your guide.

The preceding paragraph, though, is just since you asked. A hypothetical tangent, if you will. Talk to your sister, really listen to what she has to say, and think twice before exposing a sex worker to tendencies that, however inadvertent, could be toxic. Sex workers don’t deserve that.

Dear How to Do It,

For those of us who are currently single in this time of social distancing, will we ever be able to date and have casual sex normally again? I saw that Dr. Fauci suggested recently that handshakes may become a thing of the past, which inevitably led to the question (for me) of what dating and sex is going to look like in a post-coronavirus world?

—Liberate Me

Dear Liberate Me,

In the immortal words of Jeff Goldblum spoken in Jurassic Park, life finds a way. And so does that which makes life: sex. And where there is the possibility for sex, there is the possibility for casual sex. Without any moralizing either way, without guidance from neither wishful thinking nor despair, I will say with as much confidence as I can have about the future without possessing actual psychic powers that hooking up isn’t going anywhere.

I used your letter as an excuse to call my very smart friend and infectious disease activist James Krellenstein to talk about the future of sex. I haven’t seen him in over a month, thanks to quarantine. Like me, he doesn’t think COVID-19 means the end of casual sex. “These sorts of epidemics are very, very rare,” he said. “The 1918 flu killed more people than World War I, between 17 million and 50 million people. We didn’t stop shaking hands when it ended in 1920. It’s only 100 years later that we have an epidemic.” He conceded that things like increased international travel and habitat disruption might make such infections more common now, but perpetually contending with a new infection is unlikely to become our new normal. A COVID-19 vaccine/prophylaxis should do a lot to return us to where we were, in terms of socializing.

Also: Hand-shaking and sex are two very different things. “You probably shake more people’s hands than you sleep with casually. That’s true for me. I don’t know if that’s true for everyone—if that isn’t, I’m very jealous of them,” Krellenstein said. Maybe hand shakes will change or go away, but hookups won’t. Casual sex was certainly affected by HIV but by no means eradicated among men who have sex with men, even before the innovation of PrEP regimens. If we are to return to our old ways, when is the crucial component to the equation—too early could mean a new wave of infections. Stay tuned and don’t give up on your dream of casual encounters. I know I’m not.

Dear How to Do It,

Straight male here. I’ve been interested in practicing ethical nonmonogamy for a long time. I’ve never understood the concept of sexual jealousy, and I’ve always enjoyed the idea of my partner being with other people. Since coming out of a monogamous relationship, I’ve gone on dates and attempted to find people who have the same outlook on relationships.

Here’s my problem: During the course of dating a few people, I’ve discovered that many people who claim to be “nonmonogamous” seem to be lying about what they really want. To give one example, a woman with whom I went on a few dates and claimed to be non-monogamous and interested in practicing open relationships later became enraged when she discovered I was going on dates with other people.

So my question is, how can you tell that someone is truly being honest about being non-monogamous? Should I run from anyone who shows any signs of sexual jealousy? I know that sexual jealousy can exist to some degree even with people who genuinely want to practice nonmonogamy, so I feel that I shouldn’t call someone an impostor simply because they get a little jealous every now and then. But since I never experience sexual jealousy at all, I’m tempted to dismiss anyone’s claim to be “nonmonogamous” as soon as they show discomfort at the attention I give to other people. What’s the best approach here?

—Suspicious Nonmonogamist

Dear Suspicious Nonmonogamist,

I think there’s a more charitable assessment of the situation than what you’ve offered. These people you’ve dated were not necessarily lying to you; they may just have been having a hard time dealing with the transition from considering nonmonogamy to actually practicing it. We can never really predict how we’ll feel about something until we’re in the specific situation. Even if the women you’re dating have previously practiced nonmonogamy, perhaps there is something about you that makes it difficult this time around. Since we’re reading charitably, let’s say that it’s just that you’re an irresistible keeper—one they know with rapid certainty that they want only for themselves.

In general, you cannot absorb all there is to know about someone by hearing them talk about themselves upon making their acquaintance. It’s a process, and acquiring this information is one of dating’s primary functions. I can’t offer you a shortcut here. You needn’t have the cynical worldview that assumes everyone is lying until they’re proven honest, but it’s probably smart to approach these situations with your eyes open. When someone proves that she cannot live up to your standards, or those which she claimed for herself previously, it is entirely reasonable to move on to find someone with the traits you desire. The more stringent you are, the more difficult it will be for you to find a mate, so I’m cautioning against running at any sign of sexual jealousy. You have to allow people their imperfections or you’re just going to be disappointed all the time. But, yes, listen to your gut and identify the red flags as they beckon. Everyone needs filters.

Dear How to Do It,

I’m a bi trans man in his early 20s, and I’ve been dating a cis bi guy in his early 30s for about nine months. We get along really well, and we recently moved in together as a trial run before a potential bigger move. He’s super thoughtful, innovative, and intelligent. He’s also probably the “hottest” person I’ve ever been with—he’s the pretty one for sure!

The only issue is our sex life. I have always had a really high sexual drive, which has only been increased by my testosterone therapy. He is usually willing to engage my advances but not as often as I would like. I feel like he rarely, if ever, initiates. And when we do have sex, he finishes really quickly (like a couple minutes quickly) and I’m left unsatisfied. He doesn’t offer to go down on me or anything after. To be honest, it doesn’t seem like he really cares if I get off or not. I often finish myself off in another room after, and I’m not shy about it. He seems content to leave me to take care of myself. I really do care for this man, and he says he loves me and wants to spend his life with me. But I’m afraid I’ll never be satisfied by him sexually. He is less than average in size and doesn’t put any effort into foreplay. I’ve mostly been with women in the past, and I know the only way I can orgasm is from receiving oral sex. I can count on one hand how many times he’s done it. I don’t want to break up, but I’m going insane with 10 minutes of sex spread out into six sessions. I feel like I’ve dropped plenty of hints and I’ve straight up asked for him to be more attentive at least twice. What should I do?

—Quickied Out

Dear QO,

Your request is far from extraordinary—plenty of people get off only from oral—so his refusal to engage with it is pointed in its own way. Approach the conversation again firmly but with compassion, at a time when you’re both relaxed and not engaged in any kind of sex. He may have some sort of issue with giving oral sex that he’s been too embarrassed to talk about. Or he might just be flagrantly inconsiderate. I don’t think you can make any decisions without knowing the whole truth. He doesn’t owe you oral, but as your partner, he does owe you honesty. If he’s unwilling to talk about this, I can’t see the situation improving.

In the event that he will not talk about his oral avoidance, you can assess its origins roughly: If he is otherwise generous and considerate of your well-being, his issue is more likely with sex or the act than an indication of his aptitude as a partner. If he is not particularly giving in any facet of your relationship then, well, why do you want to be with him in the first place? I’m sorry that I have to graze the idea of your breaking up with him during a time when societal lockdown has made that logistically tricky, if not downright impossible, but hey, you asked. Good luck.


More How to Do It

Recently I had sex with a man who said he had a 10-inch penis. It was, indeed, huge. But when I told my friend about this guy’s endowment, he told me that specific measurement was statistically very, very unlikely, and that the guy was probably just getting away with it because people have a skewed perspective (mostly because guys lie constantly). He said my guy was probably more like 8 or 9 inches, and that is already “huge” by most people’s standards. Is this … right? How rare is a 10-inch penis? Do all guys lie?