How I Started Escorting
Promise you it’s not something I ever thought I’d start.
In 2019, while living in LA, I got diagnosed with Polycystic Ovarian Syndrome. PCOS is a diagnosis of elimination, and/or “oh hey this ultrasound shows a cyst on your ovary.” Around the same time, I went into a walking boot for my Achilles for the third time in eight years. The first time was Achilles tendinopathy and a bone spur, the second time was plain old Achilles tendinopathy, and this third time was now both Achilles and posterior tibial tendinopathy.
I got my fourth or fifth tonsillitis in there too, to round things out, or something.
I had quit a job at a dispensary in the summer of 2019, while in the paperwork process about being the primary beneficiary of my Father’s 401K. My Dad died in May 2018, and access to his Will was withheld from me by my mother and three older siblings for an entire year. The 401K situation, a year after his death, motivated me to finally demand access to my Dad’s Will and other information.
When notified by the company about my Dad’s 401K, while sitting at a reception desk because I could no longer do the standing shifts, I was both relieved for the help and shocked that information about my Dad would be hidden from me. Especially shocked because my relatives knew about my various physical illnesses and need for financial support.
All three of my siblings and my mother, all wealthy, had seen the Will the entire time. I told them all about my health challenges, about the money I was receiving from Dad, and about my six month plan to work on my podcast and music and one human show, seated creative projects that would help me as I healed my tendons and hormones and digestion and grief.
I naively trusted these relatives. I figured the worst case scenario was not being able to monetize my art projects. I accepted this potential worst case because working on my projects would still help me rest my ankle, by giving me a creative outlet other than dancing and yoga, which my health impacted my abilities to continue. I had first gone to the Big Island of Hawai’i in 2017 for yoga teacher training, and then moved back there and taught yoga. (Seems like a place to note that I paid for training, and if I had gone to medical school like was tracked for me it would have been paid for by my relatives.) My relatives knew how important yoga and dance were and are to me, and mocked my interest aside from one singular time two of them took a yoga class taught by me.
I was very wrong about the potential worst case. Said 401K money from my Dad withheld from me by millionaire relatives, who knew I was sick. I went back to an old job I worked in the Bay Area, and was selling produce boxes with Farm Fresh to You. I was wearing the walking boot I attempted to avoid my third time needing. I was sweating through my sheets almost nightly, and was doing bloodwork and other exams to search for potential thyroid or other PCOS-related conditions. I began selling furniture and clothes, and the microphones I had been using for podcasts and music, so I could afford rent and food.
In December 2019, after being told “no” for the financial support I asked for the first time ever, I went on SeekingArrangements. Living in LA, I had no idea what I was getting into with that site, which is for sugar dating and escorting. I didn’t meet up with anyone in person in LA, though I did have a couple video chats. I remember the first time a man sent me a Zelle for a video call where I flashed him my boobs — a Zelle that got my account out of the negative. I also remember a man yelling at me through the phone about saying no to coming over for $300 because “WELL HAVEN’T YOU DONE IT FOR FREE A BUNCH!” I was horrified, and felt like the sex work industry was probably “too much” for me. Being scared of what felt like “plan Z” was scary in itself.
In the beginning of 2020 I did two family therapy sessions. I sat in my therapist’s office, in my walking boot and hormonal sweat, with my oldest sibling there in person holding his phone with our mother on FaceTime. The woman who bore me told the therapist that it would be “best for Annie’s mental health if she fully financially supported herself,” and my multi-millionaire sibling agreed.
The therapist was utterly shocked, I was only half-surprised.
Perhaps with her highlighting that I never asked them for financial help until very ill, and it still being so early in grieving our Dad, and with her highlighting their enormous wealth, the therapist somehow persuaded them to give short-term help for my basic needs.
Again I was wrong about a potential worst case scenario. My mom and my brother didn’t honor the therapist’s plan for six months of financial support, and my rent money was late or less-than-agreed or had-to-be-groveled-for. So in May 2020 I moved back to the Big Island of Hawai’i, where I had lived before living in LA. This was my plan Y — find a low-labor work trade.
I found a farm with a potential for a work trade, and despite being only a couple months out of the walking boot felt it was overall more healing than staying in a studio apartment I may or may not have enough rent money for, across from a park that was taped off due to Covid restrictions. When I notified one of my siblings of finding a farm work trade, he notified the rest of the relatives who group messaged me they would not be providing any of the final month of support agreed on with the therapist.
I had planned to use the rent money for food.
While work-trading on a rural farm, my oldest sibling messaged me asking where to send my diamond made from our Father’s ashes. My Father never asked to become a diamond. I never sent my sibling the farm address. The mailbox was open, in a cluster of mailboxes in the middle of nowhere on the island. Plus, the most financially reasonable thing for me to have done with a diamond at that point was to pawn it for food money — and my sibling was aware.
I decided to go full no contact with my relatives. The family therapist we spoke with recommended I consider this more seriously, after telling me she could not professionally recommend doing more group sessions. She was not the first therapist to tell me to go no contact. Withholding the final month of a six month plan for basic life support, while I was very sick, while withholding money left to me from my Dad, while offering a diamond Dad didn’t ask to become to be sent to a rural mailbox, was my final straw to begin grieving all three of my siblings and my mother. A completely different and similar grieving process as grieving my Dad.
The distinctions between “family” and “relatives” became more clear everyday.
After a couple months, I had to stop work trading on the farm because of my ankle again. Even small plantings and weeding was too much. One of the owners of the farm kindly and graciously found computer work for him for me to do seated, which gave me more time while I scrambled with my legs up the wall in constant ankle and knee pain. I had both an Etsy Shop and Patreon for my podcast, though they didn’t make enough to even cover my phone bill.
Still unsure how to rest and heal my body, I found a room rental in town and started OnlyFans. I applied for EBT food stamps and Medicaid, which felt so surreal while sharing DNA with millionaires. I had also applied for unemployment in California in April 2020, as at first I didn’t want to clog up the system for people who weren’t directly related to millionaires who could help them. I was one of the millions who had identity theft on their unemployment, and so had to go through paperwork and hearings for it to finally come through in November 2020.
So back to September 2020, starting OnlyFans. I started very softcore, for all sorts of reasons. I was uncomfortable showing much of my body, both because of a history of eating disorders and body dysmorphia and because my body was physically hurting in so many ways. I enjoyed parts of posting, and being front-facing about it all. Sharing pictures and videos on my own terms felt healing for years of insecurities with my body and sexuality and preferences, like exposure therapy for all my conditioning to hide. It felt like a very specific art therapy project. I was confused about liking parts of something that was a plan Z last resort.
I was still too sick to teach yoga. I had considered and attempted various mindless computer jobs, and found myself completely incapable. After going no contact because of financial and emotional abuse, I was flooded with memories of sexual abuse I had repressed.
I had flashbacks of the sexual and physical abuses my whole life, though it wasn’t until the silence of no contact that I had the space to connect the dots. In college and after, I had projectile vomited multiple times during sex with men I loved and trusted. I remember talking about this and related things with therapists, unable to wrap my mind around how violently my body had responded.
Now, literally on my ass from tendon and nerve and hormonal and digestive and ovarian cyst pain, I had a lot of time to remember the flashbacks’ details.
While deep in my own tendon and hormone and trauma healing, I turned to escorting. Most of my emotional and thought space was on various sexual healings of my own, so extending it to include others felt less intimidating. My days were hazes of PTSD flashbacks with whatever grounding exercises I could do, whatever floor yoga and stretching I could do, and physical therapy. I had to budget basic things like grocery trips based on how much I could walk or carry. I couldn’t carry heavy things or go on long walks, and could manage even shorter beach walks because of the uneven surface. I was constantly stressing about my health and money, and feeling hopeless and powerless. Being sick is very expensive, and also a very challenging state to be in attempting to make money.
My ankle and knee and hips would hurt extra some days, and it wasn’t for another year when I was referred to a pelvic floor physical therapist that I knew I was also managing nerve pain.
I decided to get on SeekingArrangements again, now living on Maui. My disabilities and desperation made me more open to navigate the website, and I figured it would be very different than in LA. It was different, though I was still resistant to actually meet anyone in person.
I had two adulthood sexual assaults while living on Maui that triggered more flashbacks. I’m grateful for those assaults in a fucked up way, for the clarities they gifted me. Half awake feeling unequivocally, “I’ve experienced exactly this before.” Though I was more set back emotionally and financially, managing even more flashbacks of old memories flooding in and incapacitating me. So I took the plunge to meet someone in person.
The first client I ever had was in an open relationship, where his partner gave him permission for “paid play partners” that she approved of. We met on video chat, then I met him for coffee, then a few days later he was at my place. We talked, we fucked, he sent me a Venmo, he left.
I logged on my computer and paid a bill I was behind on, immediately.
My last escorting experience was with a man who was experimenting with his queerness, and wanted me to bring another man in. I invited a filming partner, as I had started making hardcore porn on OnlyFans and PornHub at that point. Before the filming partner came over, the client said “I’m so gay!” — while his dick was in my mouth between words of the dick about to be in his mouth — followed by “omg I’ve never said that before” and a distant stare. I felt that stare, back to a stare I’d experienced decades ago.
In the shower after I prayed that would be my last experience in person, and I could switch to all virtual. I knew an article would be coming out soon quoting me in New York Magazine, and I prayed it would give me the exposure to support myself with OnlyFans.
Then maybe I could give energy to my podcast and writing and singing and teaching yoga again, too.
Who knows how much financial freedom I could have had from online work outside of the sex industry without the various technological blocks I’ve experienced.
I had podcast ratings get deleted, and my personal home wifi repeatedly hacked, and more, before I ever started sex work. I learned even more about shadow-banning and more since starting sex work, as that community is the most targeted demographic. I also learned that sex work triggers tech companies because it is so powerful — sex work proliferates the internet and all technology, and perhaps all companies at their base. “The oldest profession.”
I survived sickness because of survival sex work.
Escorting: I’m not at all glad that it happened; I am grateful.
