I was less disciplined than I wanted to be with my writing this year, I hope this essay with three parts makes up for those who’ve been waiting a while. I’ve starting writing today on the winter Solstice, the longest night of darkness. I picture in my mind we’re all at bottom of the sea before we reverse course and slowly start rising up again towards the sun. The past two years have marked my bigger transformation of moving towards the light, coming out, writing about my experiences to reveal more and slowly become one person again. After taking baby steps, I strapped on the rocket booster in 2022 and thrusted myself up faster when I came out online under my real name, starting here on Substack. Every essay I publish, I exorcise a few more demons taking up space in my brain— they won't let met think about anything else until I release them so they can burrow into other people’s minds. Writing in this raw way and making it public have been self-therapy sessions, letting all of you witness it so I can bless it and let it go. I don’t think I would be the talented artist, jester and therapist without the suffering. I’m grateful for the dark experiences as it’s given me so many great stories to share, like paintings in my head waiting to take hold of a canvas and reveal themselves.
_______
It was ten years ago this month, December of 2013. I was on a week-long cruise in the Caribbean with my dad, stepmother and her children. It was a very generous gift from my parents as I was pretty broke at the time, just fired from my $12 an hour sales job and I don’t think I had any paid photography gigs that year. The year prior I took real estate classes at a community college and I passed the California realtor licensing exam on the first try, which I was proud of. But the fantasy I had in my mind of million dollar listings falling into my lap (it was the Bay Area after all) and collecting $30,000 agent fees didn’t match the reality of hustling hard to just get your first client. It was the same hungry feeling I knew too well as a struggling freelance photographer and hustling for clients (sugar daddies) as a wannabe baller escort.
When I look at the photos of us in swimming in the turquoise ocean, walking past the colorful architecture in San Juan and our smiling faces around the table at dinner, all I really remember is my feelings of longing and anticipation and how I had to keep those feelings a secret. Every day on the ship I would go to the business center to get on their dollar-a-minute, dial-up modem and check my email to see if my account was verified and approved on Eros Guide, the biggest sex worker advertising site at the time. I had done my first professional photo shoot the month before, created a website and my first ad as Joy, my escort persona name. All the while I was surrounded in a paradise that was gifted to me which most people would kill to have, but I couldn’t be present with everything looming in my mind.
At that time I was a semi-washed up freelance photographer and I had to take a minimum wage sales job at age 42 to help pay my bills— it was the first time going back to work for someone else since my twenties. I also hustled on Craigslist and Airbnb pimping out my rent-controlled San Francisco apartment and sometimes I got by on little allowance checks from my dad when I couldn’t pay my bills that month. I had no close friends that lived nearby, just an on-and-off boyfriend who started off as a sugar daddy but he quickly turned into a cheap Splenda dude. I treaded through life trying to get through most days and struggled with depressive episodes. Hustling was now my life and I was barely keeping my head above water.
Creating a secret escort persona was like my ticket off this boat; I would have new adventures where no one would know about my life on land.
Before I became an escort, I was playing money mind games with men I met on the sugar baby/daddy dating site Seeking Arrangement. I wasted years in “the sugar bowl” as I was brainwashed to fear and loathe the “pros” (whores.) Once I crossed that line I realized why they hated us: We were the employer with the power. We set our rates, our hours, our rules. I no longer had to swallow the truth and ego stroke after hearing the same words I heard over from every “Daddy” I met: I can tell you’re a genuine nice normal girl. You’re with me because you’re actually attracted me and not just using me for my money, not like those gold digging whores.
Riiiight. And you’re a middle-aged, pudgy, needy married dude who gets hot younger women on the side to fuck you by telling you sweet little lies so we can pay our bills.
When I was creating my escort persona, I studied other escort’s websites I admired and wanted to emulate, mostly the ones whose rates started at $1500 and over. I daydreamed about the cash, the stupidly overpriced (but gorgeous) lingerie from Agent Provocateur I would be gifted, the dark hotel bars I would nervously be meeting clients in.
And all the wild, criminalized and secret sex I would be having.
Money and sex = Illicit Whore*, which made me feel dirty and immoral and an outlaw and bad girl who would be punished and therefore I was very very
Super. Fucking. Turned. On.
When my first advertisement on Eros Guide went live I received a lot of inquires in the first week as I was the new girl on the site and everyone wanted to be the first one through the door, so to speak. I was so nervous meeting my first client which was nothing of what I thought it would be like, in a good way. The thing I remember most vividly about that session is how I felt afterward. Skipping down the street, feeling the weight of the heavy cash in my bag, smiling ear to ear with a secret and telling my old life to fuck off in my mind.
My first year as an escort was decent and profitable, I grossed around $75K and I was really proud of myself. It’s so hard to know if that’s a high or low number as so many of the “high-end”, hookers post photos of themselves on private jets flashing their new Rolexes with their classy-not-trashy French-manicured nails toasting the good life with a glass of Dom Perignon (bottle label facing front) and their client gifted Hermès Birkin bag by their side that whispers I’m a stupid ugly bag that costs as much as your car, so go have a good cry in your Subaru. They try to be all cool about it in the caption Thank you to a very special gentleman for the amazing #FMTY weekend and all the gifts, can’t wait to come back to Belize again soon xxoo <3! acting like they’re flying around the world making bank all the time and it’s an easy breezy fun life. But who knows if it’s all just marketing to get those type of clients.
The internet is the illusion we want it to be.
After a few month I started to feel restless as an escort— I saw so many men who were chronically lonely and touch starved, afraid to ask their wives for what they wanted in their relationship or got their sex education from watching porn. I wanted to be a sexual healer, to have a higher purpose and not just be the entertainment de jour. I stumbled upon a course that to become a certified somatic sex educator. I felt like I needed something “legitimate” to put next to my name and tell people what I did. I had taken previous workshops on sex and I wanted to be able to use those skills with my clients. I completed the Sexological Bodywork program in the spring of 2014 and started marketing myself as a certified somatic sex coach. I tried to get bodywork clients but I couldn’t command the same rates as full-service escorting which I resented as it was actually a lot more work, and the few clients I managed to see were boundary-pushers as they really just wanted to have sex. It was around that time the Splenda daddy turned-boyfriend and I broke up for a second time. I was free to travel and have some new adventures. I was following another sex worker on Twitter who was getting her master’s degree at UNLV and worked at The Chicken Ranch (brothel) when she wasn’t in school. I was fascinated with legal sex work after watching episodes of the HBO series The Cathouse. I contacted her and she got me an interview with Denis Hof, the infamous owner of several brothels around Nevada. They accepted me and I told my roommate I would be going away to travel around the country for the next few weeks. I had this ridiculous fantasy of what working in a brothel and living at this place would be like. I imaged it like sleep-away camp and we would all live in a communal tent and borrow each other’s curling iron, bitch about clients and gossip under the stars in the wee hours and make tons of money, all legally and in a presumably safer environment. I wouldn’t have to advertise, hustle for clients or have to screen them, the part of escorting I really hated. I would be one of the oldest campers, the hippy lady dressed in a more conservative fashion with sensible shoes. My specialty would be slow sensual connection and coaching men and couples on communication and being present during sex. My sex coaching work could reach the masses! Maybe I would be featured on HBO? I was ready for a new and exciting adventures and lots of wild stories to tell my closest friends!
(Note, I decided to edit this part out of the story and make it its own essay as it’s very long even though I left the brothel two hours after just arriving!)
I will sum up this part: when I talk to people about human rights, stigmatization and why we need to de-criminalize sex work, many assume that legalization and decriminalization are pretty much the same thing. I can tell you from experience, they couldn’t be further apart (brothel owners including the late Dennis Hof want to keep sex work criminalized and dangerous so they can exploit the system and profit off it. They’re so far to the right they might as well be on the side of anti-sex work abolitionists.) Even though I didn’t do any work in a brothel, just visiting for two hours made me even more of a decriminalization and sex worker rights activist.
Moving on in the timeline- my second year as an escort was slow, maybe because I was no longer the novel new girl. My one big spender client had to stop seeing me and we were starting to catch feelings for each other. The Splenda boyfriend and I broke up for the third and final time. Then my creepy roommate started surveilling and stalking me, so I moved out of my own apartment into a temporary place in Berkeley while I figured out my next move. I had been wanting to settle down with the boyfriend for years and I would fantasize all the time about buying a house with him, but now I had no reason to stick around. And I certainly couldn’t afford to buy anything on my own in the Bay Area. I was effectively pushed out of my apartment by my stalker, found a subletter for my room for a few months and prayed the stalker would finally give his notice to move out. I had visited Portland Oregon the year before, fell madly in love with the area and now all signs pointed north. On June 2nd, 2015 I packed two suitcases, shipped a few boxes and found a sublet with six twenty-somethings in a funky old house in Southeast Portland. I finally found home. Three months later I bought an old house that needed a lot of work so spent my time and lots of hooker money fixing it up. For the next three years I would be dealing with contractors while I flew back to San Francisco a few times a month to see clients (sometimes I wished Portland had all those rich tech bros that basically were paying for my house upgrades, but then I couldn’t afford to live in Portland.)
In 2018, after a year of construction headaches and expenses the tiny house was finally completed in the backyard. I imagined using it mainly as a work from home space to do therapeutic somatic bodywork and sex coaching sessions. I was experiencing burnout getting on a plane every few weeks to spend days cooped up in a hotel trying to line up sessions. I was also getting tired of being the one-trick pony, one-dimensional call girl. I had completed a course combining spirituality, Tantra, elements of BDSM, sensation play and sensual massage and I saw a way I could combine it with my very clinical sexological bodywork, so I cleverly made my own type of sessions. I started with tweaking the equipment I owned: I drilled 4 D-rings under my massage table and tied adjustable restraints to them. I didn’t have any real bondage furniture as I didn’t have the space to keep anything permanently out as I rented the house on Airbnb between my sessions. I often had fears that a guest would try to check in early while I was in the middle of a session. One time a guest found my leash and one of my strap-on dildos that fell behind the sofa so she asked if I had a dog (most dildos look like dog toys so I was relieved.) After that, I made sure to look under all the furniture when I finished up the session.
I liked being able to walk 100 feet to work instead of getting on a plane, but one of my worst fears came true when I saw my very first client as a Dominatrix.
He ended up being a stalker.
Naïvely, I thought submissive clients would be better behaved than the vanilla variety of escort clients, but I learned the hard to always keep my guard up as boys will be boys. One of the perks of escorting was being anonymous— I always saw clients in a hotel (even in Portland) and they didn’t know my real name or where I lived. After the incident I took steps to protect my identity but it was a fear in the back of my head with every new client I saw at the house. I did travel to work in other locations as a Domme, but I had to lug a 40-pound suitcase of bondage gear and I needed an extra large hotel room to use my long floggers.
After a few years I was burned out being Mistress M. The fear of clients coming to my home and the Domme persona just wasn’t me (I cracked a lot of jokes while cracking the whip on their ass and they laughed between moans.) I tried my hand at online sex work creating fetish content on Onlyfans (Mommy Domme MILFs are a popular fetish genre) and I didn’t mind setting up the photo shoots (I like being behind the camera) but I hated messaging fans back and forth to get them to tip me (“That’s right, @Johnnysimpcake69, mommy’s ass is so big that NO ONE will hear your pathetic screams when she sits on your face, hahaha!! Then I’ll tell all the neighbors to come over and we’ll all laugh at your PATHETIC little baby dick that would never satisfy anyone…”)
(Rolls my eyes and shrugs.)
Embodying a Dominatrix didn’t make me feel dominant or powerful. I was simply taking orders from the subs who were paying. If I was really a Dominant, when they asked me “But Mistress, how can I truly please you? I would have said something like Pay me a few hundreds dollars so I can take the day off to ride my bike, pay for a housecleaner, get a massage or write about my weird bifurcated life. Or just pay off my entire mortgage and don’t talk to me ever again, you dirty little paypig…Um, that is if you feel comfortable having the financial means to do it, I don’t want to push your boundaries. Also, I apologize for calling you a pig…
Being phony and taking fetish orders from submissive does not please me.
I needed to make money, so I kept renewing my ads and marketing on Twitter, but inquires started dwindling as my enthusiasm playing Mistress M waned.
Read the 2nd half of the story (check back in a few hours when it posts), End of an Era