“So, uh, what got you into this?”

Or — how I became an escort

Sex work has easily provided me with some of the most remarkable opportunities of my life. In the few short years since I’ve become a professional escort, I’ve:

  • Travelled personally and professionally to the US, Europe and Mexico.
  • Had a lucrative job as President of a startup company.
  • Paid off 1/3 of my substantial student loan debt and improved my credit score.
  • Made incredible friendships with amazing sex workers and our allies.
  • Become a stronger, more confident, sexually aware individual.
  • Regained control of my mental health that had been suffering for many years while working in public service.

Not bad for a hooker.

So I find it amusing to hear people ask me why I entered the business, with a patronizing tone, given all this industry has done for me. Nonetheless, I’m happy to share my story and experiences here.


I had been sugar dating on and off since 2008. Seeking Arrangement was new on the scene and I stumbled upon it while in grad school, thinking it would be a good idea to find someone to support me during my studies. Having relocated off campus to downtown Toronto, I now had a pleasant environment from which to host individuals.

I was in my 20s at the time and incredibly naïve. Although I had numerous casual partners, I had yet to negotiate the arrangement side of dating, and my first date was a quickie with an overweight Jewish guy who was incredibly arrogant. I had met a few others, but the most memorable was a guy I met in 2010 who paid me $250 for a date, ended up crashing at my house, and I slept on my sofa while he snored away (NB: I do not sleep with snorers, ever. If that’s you, prepare to have a spare bed during our overnights). What irked me was that he had stayed for so long; surely I should have made more money from this!

I dipped in and out of the sugar bowl over the years, as I had entered a serious relationship. I was having difficulty with monogamy so I ventured back in 2012 for a couple trips to Boston, which were nice but nothing special. In the fall of 2014 I was whisked off to NYC for a couple days, where I met several interesting people due to poor weather forcing me to stay an extra night at the Park Hyatt in mid-town Manhattan (sob!). But it was a January 2015 spur-of-the-moment trip that sealed the sex work deal for me.

I’d met a girl online through a mutual friend who invited me to stay with her for a few days, so I booked a last-minute trip on a Thursday and left for town the next morning. Jenna is a tall, slim brunette, who really has no business doing anything in her life other than modelling, she’s that stunning. I felt like a peasant next to her. She was always incredibly well-dressed with designer everything. She lived in a cool apartment in a walk up in the West Village, where I stayed while in town.

Jenna had been doing very well in the sugar scene in New York, but there’s a stark contrast in sugar dating between Canada and NYC. Totally different attitude, different price points, and just an all-round willingness to lay it on the line. No bullshit. Let’s do this. I had three threesomes my first day there. My girlfriend pimped me out to three of her clients, and I was the first woman she had ever been with. It was fun, and we gave these guys the time of their lives. It was the first time I’d ever done something like this: flying to a big city for sex and profit. In a former life I was somewhat against asking for money from this whole thing, but I’ve been slowly persuaded (understatement of the year) to buy in.

#tbt Winter 2015

Jenna taught me how to negotiate in this line of work; never offer your price up front, because you’re negotiating against yourself if so. Or, if they really press for a figure, suggest a range instead, and offer the clause of “I want us both to be comfortable and happy.”

Even though sugar dating is supposed to consist of “mutually beneficial relationships”, in reality it’s sex work and for those that did it full time — like Jenna — the hustle is real and truly demanding. In those short few days with her I learned how to scout and network for clients, to engage in ‘customer discovery’ — finding out what clients’ pain- and price-points are; what their needs are. I learned the importance of providing a safe, comfortable, clean environment from which to offer your services, which takes time to prepare and costs money to up keep. Then there’s the aspect of scheduling, negotiation, and overall being diplomatic and discrete about it all, while trying to earn a living.

I returned to Toronto with a gusto for sugar and in March of 2015, I made the jump to escorting proper. I contacted an agency, was hired, fired later that year, and have been working for myself ever since.

For those that were hoping for a dramatic, life changing story on my introduction to sex work, I’m sorry to disappoint you. I dove in because I enjoyed it, and income from sex work is far more reliable in many ways than that from sugar dating (a lesson to all you would-be sugar babes out there).

I’m not sure if I would have had the confidence, or at least the direct insight, to become an escort were it not for Jenna’s teachings. I definitely credit her for pointing me in the right direction and teaching me valuable lessons on knowing my worth and making myself presentable. From her I truly gained an appreciation for the hustle.

Connect with me online!

Twitter — @lafemmeisobel

Website — http://elitetorontoescort.com

Email — lafemmeisobel@protonmail.com