Ms Olivia Sinclair wears House of Harlot. Photographer: A.J Hamilton
It’s unusual being an escort in 2021, we’re pitied and glamourised in equal measure. Many presume I live the easiest life on the planet, being spoiled and adored by streams of wealthy men. Others assume this is a manifestation of my childhood trauma, that I must be desperate for money or have come to crave toxic affection. It’s particularly unusual because the industry is so nuanced and varied. There are people who fit into these categories and there are people – like me – who don’t. Not all of my clients are obscenely wealthy and my preference is to see a small selection, not an endless stream. I also run a separate business and therefore don’t lead a life of leisure in between Olivia escapades – I work.
For me the following quote by Oscar Wilde illustrates my position:
‘Give a man a mask and he will tell you the truth.’
Or how I prefer it: ‘give a man a mask and he’ll show you who he really is.’ Once you remove your identity or the consequence of what others might think, the world is a liberating playground. In my real life I am seen as reliable, professional, intelligent. Of course in a different shade those skills are required to be a successful companion, but as Olivia I’m also provocative, kinky, unpredictable without having to sacrifice my career. I can be sexual and adventurous in a space where it’s celebrated and safe.
I’ve often had a complex perspective on my own identity. I am bisexual and rarely use my ‘legal name’ going by various self-appointed nicknames. When I was younger I used to carve out secret spaces to explore, I didn’t have a strict upbringing, in fact as the youngest I was pretty much discipline-free. That being said, my sexuality was a disappintment to my family and I think learning that I am bisexual ( not lesbian) offered them a level of relief. Some of the spaces I’d explore included gay bars, festish clubs and I was intrigued by places like Camden Town. My friends and I would invent fake names and explore as someone else – or, how hindsight shows me, as our truest selves. In reality we weren’t doing much exploring, but just being around these people opened my eyes and shaped who I am today.
I became an escort at just eighteen years old which, I know, sounds horrendously young and I would not endorse this now. I had two clients who I’d see regularly and it lasted only six months. I then plunged back into a vanilla life (significantly richer) and feeling like I’d got it out of my system. Over the next few years I focussed on my career and barely looked back.
Then two years ago after a long-term relationship, I was dying to get out and explore my sexuality. I tried dating normally but I was craving an adventure, not commitment. Within a couple of months I decided it was time to resurrect my 18 year old fantasy. I applied for a leading escort agency in the UK and within weeks I was working again. I still had a full-time day job at the time and loved the thrill of finishing work, going home to have a shower and change before spending the night at one of London’s finest hotels. Often going into work straight from the date with my handbag full of cash and gifts. I found it elevated my career because when in the boardroom I no longer felt intimidated, I saw these characters through a very different lens and any self-doubt I’d felt vanished. There are pros and cons when working for an agency, but on the whole I think it was the right avenue for me at the time. You learn fast because you’re surrounded by other women. Clients were often booking duos or group dates so I would meet girls with a similar lifestyle to me and I felt understood and protected. Agencies though, are not designed for long-term relationships, they will recommend the client to whoever is available on n their desired dates, and if you take time off they will suggest your favourite sees someone else. Even so, within a year I had built myself a pool of high-quality gentlemen. One of whom would book me for multiple days a month and took me on trips to Paris and Florence. Having someone reliably see me this often meant I could be selective when it came to new clients and work less without losing income.
One thing the agency taught me was how common this lifestyle is. I met with men (and women) for whom having a companion or two (or three) was simply part of their lifestyle. It is an expensive luxury so it naturally attracts those with higher disposable incomes, but even so within a certain demographic it surprised me how ‘normal’ it was.
In the end I left the agency due to representation. My sense of self and lust for adventure was at the very core of why I became an escort and the agency marketed everyone in a similar vanilla way. I was the traditional girl next door, which increasingly didn’t fit my kinky, opinionated and original personality, so with a big kiss goodbye I decided to go it alone. I then built a brand that fully encapsulates my artistic, femme fatale personality and began attracting a different type of client. They knew so much more about me before we’d met due to my website, blogs and Instagram account and would tailor dates and locations to my tastes and interests.
When I am not locked up in my apartment I adore my Olivia dates. They don’t just offer me space to remove the shackles of my identity but they offer it for my clients too. They often tell me their deepest insecurities and secrets and we can get to know each other on an intimate level. I do actually know all of their legal names and workplaces because this is a prerequisite for meeting me, but the nature of my role in their lives encourages honesty.
Like everyone in my line of work, I am looking forward to the world reopening. I have savings but I wasn’t prepared for this to happen. Although in an advantageous position, spending my savings on my rent and bills does feel extremely disappointing, my vanilla income stream is also paused indefinitely, so it’s a frustrating time.
I anticipate a shift in my industry once the world resumes. I was already operating this way but I think many more companions will lean towards long-term friendships with a select few accepting fewer but longer bookings. I indulged in my first ever two-month exclusive arrangement last summer and I anticipate these becoming more common too. Until then I’ll be awaiting interludes in the delicious hotels, champagne soaked dinners, latex drenched desserts and a space for you and I to lift our mask.