Whorigin Stories: Part One

Madeleine Blair as “Vera,” summer 2014

Madeleine Blair II

Becoming an independent escort has been one of the best decisions of my life.

As mentioned in my first post, my experience beneath the “red umbrella” of SW includes work as an agency escort, a webcam model, a sugar-babe, a topless bartender in a strip club, and—finally!—an independent full-service companion. I first entered the adult industry while living near the Carolina coast. It was the summer of 2014; I was 26 years old. I was curious and aroused as well as significantly underemployed and nearly six-figures in debt. (Imagine! Both existing at once!)

Of course, it’s much more complicated than that. And besides, when I really think about it, my first act of sex work was twenty years ago, when I was 14. (Cool it, now! Just read on.

At a party to commemorate the end of 8th grade, a boy or two paid my friend B. and I $10 or $20 apiece to kiss for five seconds (or was it ten?). No brainer! B. was about to accompany me on a family trip to the Bay Area to visit my mom’s brother and his family. We wanted spending money for Haight-Ashbury ephemera. We’d kissed each other before; we understood boys.

Truth be told, I think most of us are Whores —at least a little bit, in the broad sense.  

Twelve years later—nearly to the day—I didn’t see the connection to this teenaged moment when I finally took the plunge and contacted “Olivia’s Elite,” a Craigslist “modeling agency” with gigs that boasted $250+/hr. Which is to say: I didn’t already feel like a Whore when I became one. After years of being called a slut for no apparent reason other than having strong opinions, I wanted to feel more like one. 

Sexuality has always occupied a large and special place within me; it fascinates me, the way it fundamentally informs how we relate to ourselves and to others. I’ve known for a long time that I’m a Whore, without much need to interrogate that fact. Truth be told, I think most of us are—at least a little bit, in the broad sense. Too few, in my approximation, embrace this faction of their identities; and only the ones who either most rely upon or most enjoy their inner Whores become literal sex workers. 

I both rely upon and enjoy it, both today and when I first started in the industry. However, when I began, my reliance upon sexuality as a skill to sustain myself was a much greater factor in my decision to work. Am I, eight years later, still toting some debt for a degree that never yielded me annually even close to a third of what I paid for it? (Oh and believe me, I tried different fields!) Well, yes. But the difference today is I can afford to feed that beast while also renting a nice apartment in a major city and divvying money between taxes, savings, and my IRAs (and, prior to COVID, that beast gobbled up $12,000 annually without denting its hunger). 

I will later interrogate whether I would have entered the industry had I not accrued so much student debt. That question is beyond the scope of this post and, frankly, one for which I don’t yet have a solid answer. I am a composer, you see. Any work unrelated to my writing has always been to support my existence as a Creative.

Regardless, I didn’t even know what an IRA was when I knocked on the front door of “Olivia”’s yellow bungalow, my sandaled feet fidgeting over a stiff-tufted welcome mat which read: “Come Back With A Warrant.” A young woman—22 years old, I’d learn—answered the door and greeted me by name. She was dressed very casually—a baggy T-shirt and yoga pants. She wore no makeup under her wire glasses; a mid-century novelist might have described her hair as “mousy.” She suggested we sit on the porch. Approachable. Sweet. Calm. Her youth surprised me, as did her plainness. I don’t know what I was expecting—someone older? more glamorous? more judgmental, maybe?—but I liked her. 

“So,” she said, pen poised above the open notebook resting on her lap. “Why do you want to be an escort?” She directed a long glance in my direction, like any other interview I’d had in my life. Why did I want to be an escort? I could have found work at yet another restaurant. I could have commuted an hour to a starvation-wage adjunct position at a community college. I could continue to cobble together hours between tutoring and babysitting and odd proofreading jobs. I could have searched harder for clients, marketed differently. And if that didn’t pan out, or pan out soon enough, I could just get evicted from my apartment, I suppose. I guess I had friends I could crash with a while, but… 

I don’t remember how I answered her question, but I do remember telling her that I knew I’d be good at it. “I just can’t believe you actually have a Masters degree,” she kept saying. 

“Yep,” I’d say. “Yep.”

Any work unrelated to my writing has always been to support my existence as a Creative.

Of my bookings, Olivia explained, she would take 30%. “You’ll still be making a lot, because you’re so clean and you’re pretty and, you know, upscale.” (Thinking back, I’m almost positive “Olivia’s Elite” only represented other white women.) In exchange, she told me, she (and her boyfriend, D.) would take care of my Backpage ad, screen my clients, and provide me with a muscle-y driver.

“Think it over for at least a night,” she said. “If this is something you want to do, let me know when we can get some photos.” I nodded vigorously. “And you’ll have to choose your working name,” she added, quipping, “That’s the best part.” She paused in a moment of reconsideration. “Besides the money, of course.” 

Before I left, she gave me the name of a website I assume is now defunct (when I type in iterations of “date” and “dating” dot-com: nada). “Read it all,” she told me. “And I can answer any other questions you have.”


I often carried my computer with me at that time, as in-home Wi-Fi had been one of the first things to go when I realized how quickly I was careening towards “financially fucked.” After getting the job, I, unabashed, pillaged the salad and hot bars of the natural grocery store, zealous with the promise of money. Content beside a kombucha and plateful of food, I opened the laptop and started to read. 

After finding Madeleine, I’d grown steadily obsessed with learning about the history of sex work, especially in the early 1900s, around the time of the Social Hygiene Movement. I knew I at least wanted to write about the industry, and that it behooved me to understand how it felt to explicitly exchange sex for money if I was ever going to do so with any authority. I’d read a lot before the interview, but nothing like the website Olivia shared, which allowed me to peer into the actual experience of a contemporary professional date. 

“That’s the best part.” She paused in a moment of reconsideration. “Besides the money, of course.” 

I struggle to describe the genre of what I read other than by calling it “instructional fiction.” It was written from a completely hypothetical stance, presumably so as not to incriminate the author, who could have caught charges for something like “manifesting prostitution” (and maybe did). For some reason, I seem to remember the site being Canadian. Anyway, it went something like this: 

Sam and Gerry sat with milkshakes. “If you were to consider escorting, Sam,” Gerry said, taking a sip, “you would ideally be in the financial position to justify a second “burner” phone from which to communicate with clients. And the best case scenario is working from a computer with a secure VPN.”  Sam leaned in, intrigued. “Of course, this is a lot of work, and requires resources.”

“‘So, what if I want to start tonight?’ Sam asked, excited. 

‘I wouldn’t advise it,’ replied Gerry. ‘Posting an online ad is often the safest way to find clients because you can screen them, and it might take a few days to find your first trick. When you’re too eager—that’s when dangerous mistakes happen.’ Gerry took another sip, appraising Sam. ‘And you’re going to want some photos. Good ones. With proper lighting. Only drunk clients respond to shitty photos, ‘cause their vision is blurry at baseline.’ A nut caught in the straw, distracting Gerry from the conversation. 

Sam’s wheels were spinning now. What’s better: hosting an in-call or making an out-call visit? Would Sam show face in an escort ad, or blur all distinguishing characteristics? Considering overhead costs, what’s a good hourly rate, and should longer sessions be incentivized? 

Gerry had finally sucked the nut through. ‘But if you need cash immediately, at the very least work under a different name, make a free Google account to conceal your phone number, do your best to get as much personal information from the client as possible in case something happens, even if you’re on the street. Always get the money first. And remember, you are charging only for your time and companionship. Whatever else happens, happens between consenting adults. Never ever EVER agree to a specific sex act for money or drugs.’”

“It’s wild to think about legality,” I told a friend later that night. “Read this stuff!”

“You know,” she said, scrolling through the Sam and Gerry saga, “if anyone else told me they came from an interview to be a hooker, I would have had some reservations. But you?” She had a sip of wine. “You, I don’t worry about.”

I smiled. “So what about a name?”

“I vote Vera,” she said. “You got excited about that one.”


“Oh! Vera: I like that,” Olivia said, taking the margarita I handed her. She had come over to my apartment to snap photos for my ad. I wore an old silk robe, some cheap lingerie from the mall underneath. As she took photos for D. to edit, I continued answering the question she’d posed in the interview, the why. 

I told her about how, at the beginning of my last semester of grad school, I lost my serving position at what was easily one of the nicest restaurants in town. I’d been making good money, and despite all the toxic traits of the food service industry, I enjoyed (and today sometimes miss!) the work: facilitating sensual experiences, shit-shooting with regulars.

“To be honest,” I told her, “losing that job was devastating, and it couldn’t have come at a worse time.” Consumed with writing my thesis, I’d handed my loan check to my landlords and subsisted on Trader Joe’s frozen tamales with rice and beans, or, if I was lucky, leftovers my boyfriend brought home from his line cook job at a diner. “I tutored some kids here and there and landed the odd babysitting job, but saving any money? Forget about it.”

“Don’t be afraid to really arch your back,” Olivia reminded me, snapping away. “And point those toes.” 

I adjusted my body, glancing to the camera lens, mind zipping to thoughts of John Berger. “At the end of my last semester of grad school, the boyfriend moved out—which, thank god—but it of course left me with double the rent—which, oh shit.” 

“Oh, fuck,” Olivia concurred.

My friend Bunny also shot me at his condo on his white leather couch wearing a black lace teddy, then in nothing but panties, his lens close to a lighting fixture to obscure my face.

Looking at the photo sets, I was surprised. I had taken plenty of sexy selfies before, but had never seen such blatant images of my body taken by others. I could see the dimples on my thighs and the pudge surrounding my navel, but Olivia seemed thrilled with our results. Through her discernment, and through Bunny’s giddiness, I saw myself differently. Like a centerfold. Aloof. Smoldering.

“D. did some edits,” Olivia said. No wonder my ass looked a little bit rounder. “Nothing too dramatic. You don’t want someone getting angry when you show up not looking like your photos.”


Olivia called with my first date. “He’s from Raleigh,” she told me. “He’s in town to buy a boat. It’s his first time seeing someone, but everything about him checks out.” She told me when to expect my driver, and I prepared for my evening. 

My friend P. came over with our usual bottle of red to keep me company as I did my makeup. With the fascination of a researcher, he watched as I concealed and powdered some blemishes on my ass. “How do you think to do that?” he asked, probably writing this moment into his next novel. “It’s so natural to you, like you’ve been doing this forever.”

We didn’t discuss the line between self-consciousness and self-awareness that night, but I think of this moment when I consider the distinction.

I was absolutely thrilled to like what I saw, to see what it was these men were willing to spend hundreds (and, later, I’d find, thousands) of dollars for.

Soon enough, my driver, W., picked me up in a Honda CRV, blasting Wu Tang and worshipping cigarettes. He had dark hair, thick eyebrows, and wire-rimmed glasses. When I commented on his Weedeater T-shirt, he launched into a monologue about Carolinian sludge rock that ended with a story about how the night prior his boss’s daughter had seduced him. He worked at a bakery for pennies, and rented a room in Olivia and D.’s house. “I gotta fuckin’ hangover,” he told me.

My first client was staying at his friend’s villa near the beach. “Always get the money first,” I heard Olivia whisper through the ether. “Fan it out discreetly to make sure it looks like it’s all there, but don’t count it in front of him.” I don’t remember the details of this moment, but I think he had the money in an envelope on the bar. He was young-ish, maybe just 40. White guy. Shy.

He offered W. a Bud Light upon arrival. In retrospect, I wonder if he did this to give me a chance to count the bills. I declined the beer (piss-water; gross) and opted to make myself a Manhattan. We sat on the porch and talked for most of the booking. He wore a little too much cologne, but I didn’t really mind.

I had the feeling he was more nervous than I was, even after I told him it was my first time, too. “Are you serious?” he asked, shocked. He composed himself. “I mean, you don’t just say that to everyone?”

He shared with me that a business he managed had been featured on a “recover my business” show on television, which I later watched on Youtube. Professionally speaking, he was a total push-over. Makes sense. (I hope he’s gotten into submission since we met eight years ago; I think he’d love it.)

Excited to create a persona, I lied and told him that I was from Oak Park, Illinois. It didn’t give me quite the thrill I wanted, and now when asked, I usually just tell people from which “vowel state” I hail.

When we headed inside, he, completely unprompted, brushed his teeth and used mouthwash before standing on his tiptoes and asking “May I kiss you?” (And this is in 2014, people! Pre-#MeToo! Don’t tell me sex workers should expect boundary-pushing!) He was more careful about consent than any vanilla date with a man I’d ever been on to that point in my life. This is certainly not to say that every kiss before it had been forced, but I had never felt like I had actually granted someone permission before.

I was hooked on that feeling, the feeling of a man deferring to me, his acknowledgment of my power and control over the situation. As someone who’s experienced intimate partner violence, this was nothing short of therapy. It brings a smile to my face just to think about how I giggled, genuinely, and responded: “Sure.” How I could taste his anxiety through the endearing consideration of mint. How an hour of my conversation punctuated with a quick flourish of my palms paid half my rent. After a some making out and brief HJ, his cum found its resting place on my outer thigh. How innocuous, I thought.

“How’d it go?” my driver asked as I got into the car. 

“Easy!” I exclaimed. 

“Well, Olivia texted me while you were in there to see if you want to take another call tonight. Have you looked at your phone yet?” 

The request was from one of the agency’s regulars. “He’s a pharmacist,” is how she described him. “Super clean.” His wife, a doctor, was working the night shift. 

I was up for it. After all, my first “date” was such a breeze. W. and I hung out in my backyard, waiting for 9pm to roll around. When took off his glasses, I was struck by how cute I found him.


The house was gigantic: completely stone, with absurd-looking columns. Inside, those eerie pastel portraits of children’s faces lined the walls. The pharmacist was super-Southern and very polite. He gestured toward the money on the foyer buffet, and we got right to business.

The pharmacist was probably in his late 40s, I’d say. The age gap was not that weird: I’d had a one-nighter with a 40-something journalist when I was 22. What did throw me off was how his body was completely shaven. I teased him when he played a Miley Cyrus Pandora station. “C’mon man,” I teased, straddling him as he laid flat on his back. “Hendrix or Dylan?” Did he think I was vapid? Uncultured? A ditz? A kid?

This date was more typical, though: not his first time and, now, not mine either. I don’t know if Olivia told him I’d had a date before him—only that it was my first night working. In retrospect especially, I detect the power differential you can only experience on your first night on the job.

Sometimes raised is the idea that sex work can be “empowering” or “a reclamation.” For one, the encounter with the journalist hadn’t ended particularly well—in the grey area that later began to be clarified by #MeToo—and I knew I wanted to fuck someone older than me. He thought my body was great, and in a mirror near the bed, I could understand why. I must’ve had sex in front of a mirror before, but this is the first time I remember it. And I was absolutely thrilled to like what I saw, to see what it was these men were willing to spend hundreds (and, later, I’d find, thousands) of dollars for. 

The night went as I expected: a taste of dominatrix-like adrenaline paired with mixed feelings about the assumption that I was a fuckable imbecile in class drag.  

I lost track of time. I accidentally overstayed. My phone was blowing up. When I realized it, I quickly excused myself. He was gracious, with a sleepy expression I am now unable to categorize as a smirk or a sneer. 

“I was about to come knocking!” W. huffed when I got back into the car. “Only reason I didn’t is ‘cuz Olivia told me he’s a regular and thought maybe he’d extend. Did you ask for any extra money?”

“No, I, uh…”

“Oh, Jesus,” he muttered, driving away.

“I, uh… wasn’t watching the clock.”

“What do you mean ‘not watching the clock’?” he barked, lighting a cigarette. “That’s kinda the whole fucking point.”

Olivia texted me. R U OK???? There were several similar messages beneath it. My euphoria was gone. “I just…”

“I mean, she told me it’s fine, you’re new, she’s not going to make you pay for it.”

“She did?” I verified, scrolling through her messages. 

“Yeah, she’s not going to try to scare you off on your first night.” He took a drag and visibly relaxed; I heaved a sigh. “So,” he asked, “how did this one go, other than you letting yourself get fucked over?”

“Oh, shut up,” I snapped back, finding my groove alongside his brassiness. “It was fine. More physically exerting than the first, but still easy. He was nice.” He finally rolled down his window to release the smoke. “He was playing fucking ‘Wrecking Ball,’” I laughed. “And he shaved his entire body,” I noted. “Which was all very pink.” 

“Gross,” he said.

“Not gross,” I retorted with vehemence that surprised even me. “Just…like a naked mole rat.”

“Gross!” he laughed, and I joined him. “Wanna get a few more beers?” he asked me, dialing up the volume on his CD when “C.R.E.A.M.” came on. I rolled my window down farther to feel the Carolina night air.


I knew I’d been duped; the pharmacist was experienced and had known what he was doing. I should have been smarter, and more aware, and it was truly a learning experience. The night went as I expected, all in all: a taste of dominatrix-like adrenaline paired with mixed feelings about the assumption that I was a fuckable imbecile in class drag.  

W. and I chose a 6-pack of IPA and drank them in my backyard, talking until 4am. He slept on my couch; we went to the beach when we woke up. As the summer progressed, we were spending at least six nights a week together, usually at my apartment. He started contributing rent, alleviating my financial situation substantially.

I switched to camming; we also tried to cam together, but lacked the self-control to sit next to one another barely-clad without logging off to bump uglies. Vanilla work picked up when school resumed. Eventually, my (read: regrettable!) hiatus began. We spent the next two and a half years together, and he’s still one of my best friends. When my partner and I visit his partner and him, everyone exchanges hugs. He and I still say I love you when we get off the phone.

When W. and I broke up, I dabbled in sugar-babedom before taking the plunge into companionship. Becoming an independent escort has been one of the best decisions of my life. I have had the luxury of pretty much always choosing the clients with whom I’ve worked, and I have—with very few exceptions—felt more compensated for my time than at any other job I’ve held in my almost two decades of work experience, even when I was managed (I am very lucky). My re-entry is another tale entirely. 

Whether you revere or revile or question my words, I hope you comment and join the conversation with me. If you enjoy reading, you can always support this work by subscribing to my Patreon here, or by tipping me via Cash-App ($madeleineblair) or Venmo (@cookiegoogleman). Even small gestures are encouraging and deeply appreciated. Really.

Thanks for popping in!

*Sex workers everywhere stand in solidarity with the victims and survivors of labor trafficking and exploitation. If you or someone you know is being forced to work against their will, you can contact the SWOP’s Community Support Line at 877-776-2004 -or- the Human Trafficking Hotline at 888-373-7888 for support.

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