Madeline is a 23-year-old prostitute. She’s been selling sex for more than two years, primarily sleeping with men she meets through sugar daddy websites. She talked to me about her life fucking Saudi princes, paid orgies, and the truth about men who pay for sex.
So how long have you been fucking people for money?
Madeline: Since I was 20. For a long time before that I’d had a prostitution fetish. I was living in London at the time, working as a nanny, and basically I crashed the family’s car. So I was looking on Craigslist for babysitting gigs to make extra cash to help them pay for it, and I noticed there were a few ads from older men looking for a “rendezvous.” Most of them were like sixty years old, but there was one guy who was 32 and offering £500 for an hour, so I emailed him and was like, “I’ve never done anything like this before, I have no idea if I’m even capable, but I’m interested.”
He was very polite and eased me through the whole thing. I asked him a million questions—literally down to “Do I have to act into you?” He just made me feel really comfortable. So I went through with it and I really, really liked it.
You just went and fucked him at his house or something?
No, we got a hotel. But basically after that I knew I could psychologically handle having sex for money–it wasn’t just a fantasy anymore. And then I came across an article about sugar daddy websites, and so I made a profile on one of the sites, just to see if the daddies were only looking for supermodel types, and I got loads to replies. That was more than two years ago, and I’ve been doing it ever since.
So you see sugar daddies, and you also work for an escort agency, right?
Yeah, but I only do the agency when I’m low on cash, because it’s a sure thing, and I know I can definitely make a certain amount in a night. Working for the agency is more standard prostitution–you’re given a driver/bodyguard who drives you around the city in a black car, and you see multiple clients in a row, who are all pre-booked for you by the Madam. But I’d much rather see an SD. It’s classier and more fun.
So what types of guys do you meet through sugar daddy sites and what do they want from you?
There’s generally two types of guys—I’ve nicknamed them. There’s the ‘Bleeding Heart,’ and the ‘Contract Sugar Daddy.’ The ‘Bleeding Heart’ actually thinks he’s in a relationship with you and wants you to generally be attracted to him, and wants to spend time together and for you to have sex with him. Those types are always like, “I’m always really generous with my girlfriends so I don’t see why this is any different. I would take care of you anyway, so the fact that we met on this site doesn’t make a difference for me,” sort of thing. Sometimes they even want you not to see other people. And the Contract Sugar Daddies are more business about it, and pay you a set fee each time they see you, or give you an “allowance” of a set amount each month.
So with the Bleeding Heart types do you have to “act” a bit more?
Yeah, you need to cuddle, you need to sleep over.
You sleep over? Eww.
I know it’s really awful, I hate doing it. I can’t sleep! But I tried the whole, “I can’t sleep over, I don’t sleep well” thing, but sometimes they won’t call you back if you don’t. I feel like I’ve missed out on some opportunities by not sleeping over. I’m thinking of investing in sleeping aids.
I feel like I’d be scared the guy would murder me in my sleep.
I think by the time you’ve been comfortable enough to lock yourself in a room with someone and get naked, you’ve committed. And by the way, guys you meet in bars for one-night-stands can murder you in your sleep too! I’d rather not sleep over, but if it means getting a more reliable SD then I’ll do it.
So have you ever met an SD who you were legitimately into?
Definitely. There was this one guy who was a Saudi prince. He flew me to Paris first-class and put me in a five star hotel. When I got there, there were four dozen roses and a bottle of Dom Perignon from my birth year. And at that point I hadn’t even talked to him on the phone, we had just emailed and sent pictures. When I finally saw him in person I was nervous because he was so good looking. He looked like Aladdin. His deal was that he wanted to meet me in Paris once every other month and he would give me 30 grand over a six month period.
That’s crazy. So what happened?
We had dinner and then went up to the room and fucked a couple of times. I was really into it but he was kind of insecure like, “I know I’m good but I’m not that good.” I felt like I had hit the jackpot.
So did the 6 months deal pan out?
Well, no. What happened was that he gave me five grand on the first night, and the next morning he went to Cannes to do renovations on a house. So I just stayed in Paris, and he was like, “Charge everything to the hotel and I’ll take care of it,” so I invited friends over and we would just order room service and watch TV and jump on the bed. But after a few days, when he still wasn’t back, I got an email saying, “I’m sorry darling, this is my first transgression against my wife and I don’t feel good about it.” It was totally fair enough, but it sucked as well!
So do you have a reliable SD now?
I’ve been seeing a lot of this one guy who runs a fashion company. He wants to dress me up as his doll and put me in high fashion shit, so that’s cool. He’s really fun to hang out with, and actually sort of has a gay vibe. He texted me today with a plan for our next date saying, “We’ll go to the spa and get mani/pedis and then we’ll go home and have sex and then we’ll go shopping and get you all dressed up and then we’ll go to Book of Mormon and then we’ll go to a fabulous dinner.” LOL. Like, can’t complain there!
But you “date” more than one SD at once, right?
When I first signed up I was really ‘girl next door’ about it and would only talk to one person at a time. But you kill so much time that way. It’s not like I’m trying to have five guys at once–I’m too lazy for that. Ideally I would just have one reliable guy. But these guys are so unpredictable and flaky. Like for example I had this one guy who was amazing. We met a total of four times and we never had sex–we’d just have dinner or get drinks–but every time we met he’d give me a thousand dollars in an envelope.
Wait, why didn’t you have sex?
Because he did but he was, like, getting to know me or whatever.
Yeah. So the first meeting we just met for drinks and then he had to go back to work, but he handed me an envelope. The standard for a non-sex meeting is usually around $200 to $250. I’m not saying the majority of guys do that, but if they want to show you that they’re serious about being a sugar daddy, and that they’re capable, they usually give you a gift. So anyway that’s what I expected, and then I looked in the envelope and saw a grand and was like OMG.
That’s insane. Was he good looking?
Yeah! He was really cute. He wasn’t my type but he was like 35, 6’2, blond hair, Tom Ford suit, nice glasses. He was totally someone I could take out and not be embarrassed by. He wasn’t “cool,” like he doesn’t work at Vice or whatever, but he was fine.
He wasn’t alt.
Defs not alt. But I was really pumped on it going somewhere. So we went on four dates and every time it was a thousand dollars, and then on the last date we made out and he was like, “I’m really happy I met you,” but then I just never heard from him again.
That’s so weird. Do you think he found another girl?
Who knows. That’s what I mean, these guys are so flaky. Maybe he was married. If he found another girl that would have been totally fine. The thing about these kinds of relationships is that they’re so direct and honest–you’re basically a commodity, so guys can just tell you if they don’t want to see you anymore and it’s not a big deal–which is why I was so confused when he disappeared with no explanation at all.
This seems like it’s a huge part of your life. To what extent do you keep it a secret? Do your friends and parents know what you do?
Most of my friends do. I have no filter! Especially when I’m blacked-out, lol. I always end up telling most of the guys I’m dating in my “real life” about my job too, which is probably why I haven’t had a boyfriend in a couple years. I would really like to find someone to date who didn’t mind my work though, and for the right person I would probably be willing to work less. Also, my parents know what I do because my sister told them. Afterward I got a call from my dad. He literally said, “Hey honey, I heard you’re turning tricks.”
Well, they care, but they’re hippies, so they’re sort of ok with it. Once my dad was really low on cash and struggling to pay his bills, and I was home visiting him and felt really bad. So I went on the site and this guy was offering me $1,000 for a blow job, so he picked me up and I sucked him off and was back like 30 min later, and just handed my dad the cash. He started crying actually, he couldn’t really deal. But he was also like, “What the fuck, you were only gone half an hour!” He could NOT believe anyone would pay me that much. I was like, “Uhh… Dad, that’s actually weirdly insulting.”
That’s so awkward, we need to move on. So do you ever sleep with other escorts, like in an American Psycho threesome sort of way, but without the chainsaw?
Yeah, actually I have one client who only sleeps with more than woman at a time, so with him I only do threesomes. He always brings the other girl and gives us each $700, and the whole thing takes about an hour. He’s so sweet, I love him. He grew up in a really poor family, so it’s a rags to riches story.
Do you like the threesomes?
Well threesomes are cool because you only have to do half the work. But there’s a bit more pressure, especially because I never know what the other girl’s going to look like, and I’m always nervous she’s going to hate me. I have more confidence with wooing men than I do women. I can’t tell if a girl is thinking, “I can’t wait for this to be over.” I guess it’s an insecurity thing.
Do clients ever want you to do really kinky shit?
I recently had this one client who’s an amazing German guy, early thirties, top lawyer in his field, speaks five languages, and he was staying at the Ritz and we would go for really nice dinners. The sex with him was really weird and perverted and hot. He’s really into lactation. He was like, “You might be a little young but maybe three years from now, if you work on it and milk your tits, you’ll be able to lactate.” And he’d always be working my tits. One time he was lying in bed, completely naked with a boner and a pillow on top of his face, and he was like, “This is my newest fetish,” and I got on top of him and was fucking him while suffocating him. It was just fun, adventurous, interesting sex.
But I’m semi confused because for the guys it’s like—you’re good-looking, you’re successful, you’re rich, so why can’t you just fuck someone without having to pay them? Are they just awful people?
No, they’re usually fine. They’re just too busy. And they have standards. It’s hard to just meet someone at a bar who’s hot and smart and who you can have an interesting conversation with, who also wants to fuck you on the first night.
And they know they will find hot and smart girls on an SD site?
Well they can read your profile. If your profile is written well and witty and your photos are hot, that’s a good start.
So how much money do you make per month?
It’s so month-to-month. But I had one arrangement that was 7.5K a month just from one guy.
Really? Do you have a huge savings?
No, I have zero savings! You think it’s so much money until you have it. I think my biggest problem was that I felt almost guilty about how much money I had, since my friends are obviously all young and poor, so I would just pay for everything. Also I had just moved to New York so I was going out every night until 4am, and basically paying for everyone. And my apartment was $2350 a month. That was part of the deal–he was married so he wanted me to have my own place and he asked that it be within four stops of Grand Central.
How long did that arrangement last?
Four months, and he told me it would last that long right from the beginning, which was cool.
So has whoredom been a pretty positive experience throughout, or has there ever been times when you felt used or in danger or whatev?
That’s so subjective, if you’re asking me that versus another sugar baby, you’re going to get very different answers. One of my closest friends signed up and was getting slimy messages and was not really into it, but it takes a lot for me to be shocked or grossed out. Also I sort of get off on the riskiness of it. I genuinely love my job.
Would there be a reason that you would say no to sleeping with a client?
No. The only time I walked out of a meeting was when an agency sent me somewhere really shady–like a drug den, and not the baller swag type of drug den.
Do you have personal rules for yourself?
Always use condoms, I always meet SDs in public before going to their houses.
What would you say is the best part of the job, besides the money?
You get to meet people outside of your social circle, which I like. And also this job has led me to discover that there is a silver lining to everyone. There are guys I go on dates with who in “real life” I wouldn’t look twice at, but when I’m forced to sit down and talk to them, I always find something endearing about their personality. Like maybe the guy know tons about the soil in Argentina and how it affects the climate… I can get down with that, I can take home some trivia.
So basically being a whore makes you rich and smart.
Totally. Or at least I know way more about the stock market than most 23-year-old girls living in Williamsburg.