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How a Sex Worker With Hefty Medical Bills Shops

Alyssa, 30, is a lingerie designer whose sugar daddy helps cover expenses.

An illustration of a coin being dropped into a piggy bank.

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Welcome to Racked’s How Do You Shop? series, in which we ask a variety of people some deeply personal questions about how they earn, save, and especially spend their money. If you know or are someone with an interesting relationship to $$$, email

This week we spoke with Alyssa, 30, who lives in a major Midwestern city and covers immense medical costs — as well as rent — with a little help from her sugar daddy and an inheritance from her mother.

What is your job?

I run a small lingerie business and I’m a sex worker.

What is your annual salary?

It varies so much because the [lingerie] business is really new, about 14 months old. January of last year I made probably $500, and then December of last year I made $3,000. When I was still bartending the first half of last year, I made about $25,000.

My mom died 10 years ago, and she left me some money that’s been sitting in a trust fund. When I turned 30 a few months ago I got the money, and I had been using it to pay my medical bills. That’s also how I paid for college. Once I had the money, I made an assessment of my financial situation and was like, “If I continue to be sick, this really isn’t going to last much longer.”

I have this mysterious chronic illness that’s like an episode of House where no one can really figure it out, and I have to get a lot of tests done all the time. I’ve had surgeries in the past few years — and that shit’s expensive.

Basically, my sinuses just stopped working four years ago. I think I’ve seen seven different ear, nose, and throat doctors at this point, and I finally found one who’s able to help me, because they all just do the same thing, you know? They just throw antibiotics at you and don’t try to find what the underlying thing, what’s causing it.

If you had to guess, about how much did your medical bills run in total last year?

I get my insurance through the ACA, so that’s another reason I’ve been panicking about money since the election last year — since the future of the ACA is uncertain. If the ACA gets dismantled, then I probably just have to get a job at Starbucks so I can survive. I’ve been trying to trick people into marrying me so that I can get other insurance, but that hasn’t worked so far.

Last year [my medical bills] were about $9,000. My co-pays for insurance are just a couple hundred dollars a month, but because I have a really atypical illness that there’s no given treatment for and it’s still stumping doctors, some of the treatments that I have aren’t covered.

This is something they don’t tell you: Insurance helps you until you get really sick, and then you’re kind of just on your own. I get some prescriptions that are custom-made for me by a custom-compounding pharmacy, and those I have to pay for out of pocket, and it can be, like, $400 a month. It’s kind of fucked.

How much money did your mom leave you when she passed away?

$100,000 is what’s left of it. I mean, it was a lot, so I don’t have student loans and I paid off all of my medical stuff prior to this year. When you have a strange, chronic illness that doesn’t have a prescribed route of treatment, that can just disappear so quickly.

Tell me a little bit about the sex work that you do.

I have a lot of friends who do sex work, and it’s something I’ve been curious about for a long time. I have a really high sex drive and I’m into weird shit.

Honestly, I’ve been so busy with my business that my business is like my boyfriend right now. For the past year, my sex life has just been casual sex with people that I don’t even like. I wanted to monetize that interest. I started dipping my toes into it maybe four months ago. I talked to a few friends who do it, who have been doing it for years or decades, and it just seemed like a good idea. I started to try it, and I like it. It’s really interesting.

Right now, I’m sugaring. I have one main client who I see once a week. We text each other and keep in touch. He lives in a few different cities because he’s a one-percenter. He’s a retired CEO. He is filthy rich. We go on dates and then have sex. I spend the night at his house sometimes. He’s married. His wife lives in another city and obviously has no idea.

He pays my rent, which is $1,100 a month. That includes my work studio, which is in my apartment. Then every time I see him, he gives me a few hundred dollars.

On top of that, if I need anything, I can ask him for it. The last surgery I had before I hit my deductible last year, the co-pay was $3,500, and he just paid that for me. When I told him how much it was, he pulled out his phone and PayPal-ed me $3,500 — which is insane.

I feel like a lot of people think the hardest part is having sex with a guy in his 60s, but the hardest part of the job is definitely keeping my mouth shut when he talks about politics. I try to, like, steer the conversation away from there.

He’s very conservative. He voted for Trump. He’s actually the first Trump supporter I’ve ever met. Every now and then he’ll just say something that’s so fucked up. The other day, he made this comment that was just, like, really racist. It’s so against my nature to just not argue or call people out on their bullshit, but at this point, I’m relying on him. Like I said, I spent about $9,000 on my medical expenses last year. In the two months that I’ve been seeing him, he’s already paid all of that off.

But I get mine, too. Whenever my sugar daddy says something racist, I take a chunk of the money he gives me for that particular date and donate it to Black Lives Matter. It definitely makes it easier to keep my cool just knowing that he’s unwittingly supporting the very people that he’s putting down.

If you had to guess, how much a month on average would you say that your sugar daddy gives you?

I’d say probably around $2,500. Then with paying for the surgery on top of that, that’s an insane amount of money.

Do you ever go shopping with your sugar daddy?

No, but that’s definitely what Seeking Arrangements advertises itself to be — you find someone and he’s going to take you shopping for handbags and things. The sugar daddy I found was specifically seeking out someone like me. On his profile, he said he was looking for a woman who was a single mom or in grad school, a woman who didn’t want to be spoiled with expensive manicures but actually had a reasonable need for money.

Like I said, he’s a retired CEO, so he loves that I have a small business. He loves giving me business advice; a lot of it is just, like, him getting off on explaining something to a younger woman, but a lot of it is actually helpful.

I value all of the advice he gives me. He was also a business professor for a while, so yeah. It’s definitely helpful to sit down with someone who has so much experience in running businesses and have them look at your business model and give you advice.

He’s got to be really dope come tax season, too.

Yeah, for sure. I’m not paying taxes on what he gives me. At a certain point, when I’m making more money a year and I find more clients, I’ll have to figure out how to make that work without getting arrested — but we’ll burn that bridge when we get to it.