How to Do It

My Brother and His Wife Think I Should Use My Virginity to Pay Off My Student Loans

I can’t shake my feelings of reluctance.

Woman's silhouette with a lock next to her.
Photo illustration by Slate. Photos by Getty Images Plus.

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Dear How to Do It, 

I graduated from college in 2019 but have had no luck finding a job in my field. My high-functioning autism makes food service and retail work impossible for me, so I’ve been applying for various administrative jobs (I’ve had numerous interviews, but haven’t been hired), as well as jobs like hotel night clerk, security guard, kennel worker, and cleaner/janitor (I haven’t even gotten any interviews for those). Since the pandemic hit I’ve been living with my older brother, his wife, and their girlfriend “Sage.” My conservative parents are not happy about this, and have cut me off financially. Even doing all the freelance writing and editing I can get, I don’t quite cover my expenses, so my brother has to help me out. He’s extremely generous but he and his wife are not rich, and have let me know this can’t go on forever.

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Sage, with whom I share the apartment in their basement, is a sex worker who makes about half her income online and half doing outcalls for a small list of clients. She makes good money, has never been in trouble with the law, and seems happy with her career. I’ve watched her work several times from off-camera, and have been OK with it, so she’s offered to help me get set up and give me all the mentoring I need. She thinks my virginity alone could pay off my student loans and launch me on a successful career. (Although she wants to list me as being 19 or 20 instead of 24, which makes me anxious about being found out.)

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I’ve given it a lot of thought, but haven’t quite been able to get over my misgivings. I’m an extremely private person, and hate the thought of sexy images and videos of me being potentially out there on the internet forever, or having to touch, make eye contact with, and have sex with a man I’m only pretending to find attractive.

My brother and sister-in-law have hinted that as a progressive feminist I’m being hypocritical for not wanting to do this, and spoiled and selfish for continuing to live off them instead. I still can’t shake my feelings of reluctance, but don’t even know if I have a right to feel this way. If, for example, after searching this long, I was offered a job cleaning public toilets, no matter how much I “hated the thought of it,” I’d be a spoiled brat to turn my nose up at it, right? So how is this any different?

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—Why Can’t I Just Clean Toilets?

Dear Why Can’t I,

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Entering sex work is different from taking a gig cleaning toilets. Sure, people might look down on you for being a janitor, but they aren’t likely to fire you from a job for having previously done that work. As up close and personal with smells and humanity as toilet cleaning is, it still isn’t as intimate as sexual labor, especially sexual labor that involves taking parts of another person into your own body.

I spoke with Reese Piper, an autistic woman living in Brooklyn who works as a stripper and writer, about sensory processing and sex work. She mentioned how eye contact, for one, can be complex and manageable.

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When I’m chatting to customers on the floor of the strip club, especially when it’s loud and crowded, I find it arduous to talk face-to-face because eye contact can make it harder for me to process language. That is, when I look people in the eye I struggle to understand what they’re saying. Simple strategies such as looking at the space between the customers’ eyebrows or staring at their noses can help, but I find chatting side-by-side to be the most beneficial to my income and well-being. When I’m approaching a customer to chat before suggesting a lap dance, I always recommend we sit next to each other at the bar or on a couch or on their lap so I’m not face-to-face. Lots of autistic people prefer to socialize ‘peripherally’—they find it more comfortable and less distracting than talking to someone head-on. Similarly, during more intimate moments with customers, I’ll whisper in their ear or bury my face in their neck, which again allows me to connect without making direct eye contact.

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So, there are ways to navigate your needs while catering to customers.

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Privacy, as you mention, is another concern. Once sexual images of you are on the internet, they’re there forever. Cory Doctorow described the internet as a “copying machine” in his 2011 book Information Doesn’t Want to Be Free, and that remains true. One uploaded copy becomes several online copies, each of which can be reuploaded. There’s no taking it back, and these images have a way of resurfacing at the worst possible time. If you’re uncomfortable with the idea of explaining your sexual images to a boss 10 years from now, please, listen to your gut and say no to this offer.

If your brother and his wife are putting pressure on you to engage in sex work, that’s coercion, and coercion isn’t OK. Sex-positive feminism sometimes twists and becomes an imperative call to engage in all the sex, including sex we don’t want to have. This can extend to sexual performance and sexual labor. Listen to your own boundaries and respect them. You’re the person who has to live with the ramifications of your choices.

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In the event you decide you would like to begin working with sexuality, Reese has some advice.

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There isn’t a lot of information readily available about the industry on the internet, so it’s imperative that you have a community of people you can rely on. Friends will give you the down-low, they’ll teach you about the unspoken rules of the industry that you may struggle to grasp. They’ll teach you how to make money and may help you find customers when you’re financially struggling. And hopefully, friends will have your back if anything bad comes your way. That being said, don’t immediately put your trust in one person. Let friendships build over time and focus on building multiple relationships, not just one.

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You would need more than Sage as a mentor. And, in case you need this to show to your brother: Feminism is about freedom of choice. That includes the choice to hold out for a job scrubbing bathrooms in the park. That includes the choice to decline sexual labor, or sexual interaction at all.

Dear How to Do It, 

I’m a 33 year old woman who has had sex with men and women (both cis and trans) in the past. But lately, I’ve started to realize I’m very attracted to and interested in dating trans men. I have major love and respect for the trans community, as I have several immediate family members who are trans as well as close friends. So I’m really not sure how to explore my interest without being gross or coming off like I’m fetishizing anyone. Any ideas?

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—Branching Out

Dear Branching Out,

Objectification can be a part of healthy sexuality. It can also cause the objectified person a lot of pain. I imagine your desire to avoid being cross or coming off wrong is partially out of concern for the feelings of the people you’re hoping to hook up with. I reached out to my friend James Darling, trans man and queer porn icon, for some insight.

The line on fetishization and appreciation is really about intent. What is it about trans men that is holding your interest more than other types of men? Is it something physical, mental, emotional, or specific sexual acts and interests? It’s worth exploring and doing some work on your own around why this is important to you, without making it the trans person’s responsibility to process your interest. While some trans men would be relieved that someone is seeking them out because they are trans, some guys would be extremely uncomfortable with assumptions or perceptions about their bodies or what it means to be trans. Everyone is going to feel differently, since there are as many types of trans men in the world as there are other types of men. It sounds like you already have trans people you love in your life, which is a great sign because it hopefully means you are already familiar with some basics of what trans people go through. It’s very important to communicate where you’re coming from and as long as you are treating the trans person in question with respect as a whole person, like you would any other person you’re attracted to, you’ll be fine!

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When you’re thinking about James’ questions, you might journal, take a long shower, or go for a walk. Whatever helps your mind process these thoughts. Speaking with a trusted friend is another option. When you’re talking with a potential sexual partner, remember to use your active listening skills. I think you’ve got this.

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Dear How to Do It,

I have a problem with my partner of six years. Almost every time he performs oral sex on me I get a UTI. It really is terrible because he is so good at it, and it’s one of his favorite things to do. I know I’m really clean and also, I go yearly to my gynecologist and get an STD screen just in case because you never know if someone is cheating. I thought maybe it was his mouth. He went to the dentist and had several crowns and work done. Is it possible that his “flora” is just not compatible with mine? Also, he’s well endowed and takes a while to climax, so there’s lots of friction. I have always known to take a probiotic since I am into holistic health and yoga. I have never had this problem before and I’ve had multiple hookups and several other long-term relationships with men and women. I’m 44 now and it’s only been with him. I just want to have hot and heavy hardcore sex and sit on his face without getting sick.

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—Eat My Peach

Dear Eat My Peach,

It is completely possible that your partner’s oral flora is detrimental to your urinary health. If you haven’t already tried peeing after sex, that’s your first tactic. You also might try a dental dam, which is a sheet of protective material that needs to be held in place against the vulva (or anus!) with at least one hand. A company called Lorals makes single use latex underwear for the purpose of STI protection under the name Lorals for Protection, and received FDA approval to market that product for safer sex earlier this year. I haven’t tried the Lorals undies myself, but I imagine that the hands-free nature of the protective barrier is an improvement.

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If these suggestions don’t work, it’s worth having a talk with your gynecologist and his dentist about what might be going on. Good luck.

Dear How to Do It, 

I have recently been exploring kinks with my wife. Hers seem pretty tame (light bondage, mixed with humiliation and praise in equal measure) while mine tend to dip further toward kinky.

For example, I enjoy anal (giving) and bondage, I can be very sadistic when I really get into role-playing and enjoy role-playing incest (purely fictional, we are not related in any way). I think I might also be into watersports as well, and this is where the problem lies. I’ve expressed interest and she claims to be willing to indulge me but has let me know she doesn’t feel the same way. I’m deeply in love with her and when she isn’t into something I find myself losing interest as well. Is this something I should just let drift into oblivion or should I continue to explore this interest since she’s willing to participate, even if she doesn’t particularly enjoy it?

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—Calm Waters

Dear Calm Waters,

You say you’re losing interest in some of your kinks because your wife has expressed a low-interest level in them herself. Why force it when neither of you feel passionately? Even if the two of you have done yes-no-maybe lists together, where you independently state your interest in a lengthy list of sexual specifics, it might be worth revisiting the exercise. Once you’ve both filled out your sheets, compare them to find where you overlap at this stage in your relationship. That might change—she might develop a new interest, you might develop a new interest, one of your older interests might become appealing again—and, if that happens, you can have another talk.

—Stoya

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