Madison Winter shares her story with ASN Lifestyle Magazine — from how sex work helped her break out of her dull career to how to assert boundaries as a professional in the sex industry.
How did your journey begin as you to explored sex work?
I actually discovered sex work somewhat accidentally. At the time, I worked in the financial industry, asset management at the time. While I enjoyed what I did, I wasn’t particularly thrilled with the 9-5 cubicle, florescent light scene, and I think subconsciously, was looking for a change. One night I came across a fiction flick on Sugar Babies, and became totally enthralled, despite the super serious and negative undertones of the movie. I now look back to it and giggle a bit about it. The entire premise was your stereotypical, college girl meets handsome older guy, who exposes her to a double life of adventure and financial freedom, albeit at the expense of her good Christian girl morality. I remember watching this on my sofa when I was about 24 at the time and thinking “hell yes, sign me up!”
From there I dabbled in sugaring, and eventually into agency escorting. I ultimately ended up leaving my full-time finance role (temporarily, as I thought!) and began escorting independently.
I’ve now been a self-employed provider for over three years, and can say I don’t regret a single moment.
What is one of your favorite things about being a sex worker?
Choosing one... I’m not sure I can! There’s so much I love about being a sex worker. First, I had no idea how well suited I was to entrepreneurialism at the time when I began. The idea of building my business plan, investing and re-investing back into it, and curating a book of business suited to me keeps me buzzing. Being my own boss, setting my own hours, monitoring and tweaking my marketing approach and brand, expanding into different ventures — all of this encompasses sex work, and I find it extremely exciting. Additionally — the relationships. When I got into this line of work, the enormity and depth of the personal relationships I’d develop hadn’t yet occurred to me. Here’s the curious thing about spending time with strangers — it can completely shift your entire sense of self. The bubble that is the client/companion relationship is one that exists in this particular realm of vulnerability (on both sides)! We’re both free to explore, listen, learn, and grow in a way I wouldn’t have been able to do in conventional relationships. Spending time with clients has shaped me into a better person.
What are some qualities that you have to have in order to work in your profession?
I’ll be frank. Sex work as an industry has a relatively low barrier to entry. There isn’t a particular set of skills required to get started; all you really need is an open mind. That being said, the sex workers that I’ve watched flourish, are those with business acumen, ambition, a clear sense of self, and a high EQ. Notice I didn’t mention looks or personality. One thing that people aren’t often aware of is that sex workers can come in all shapes, sizes, colors, physical abilities, and sexes. Also, any personality type can be successful. At the core, we’re simply humans connecting with humans, and attractiveness is completely subjective. However, I believe in business acumen and a strong sense of self for a couple of reasons. Sex work, unbeknownst to the general public, is a massively time-consuming venture, not unlike any other small business. Knowing your specific skill set, target audience, and niche market is something that can help immensely. I also mentioned EQ (not to be confused with IQ!) and the reason why I choose to highlight that is because we’re not simply salespeople. Our job is to meet with a diverse range of personalities, clientele from all backgrounds, and create a connection — mentally and physically. You need to be an emotional chameleon.
You travel around a lot. Tell us about the most exciting escapade you’ve experienced, and why it had such an impact on you.
I do! Travel is a huge passion of mine in my personal life! One of my favorite trips to date was a month in India and Sri Lanka. I try to visit countries that are ethnically and culturally different than home, and I actively try to put myself in situations that I wouldn’t normally be in. One of my fondest memories on that trip was interestingly enough, spending five hours on a bus, next to a young mother and her son. It was around Christmas time and we spent most of the journey comparing the holidays between countries, discussing her family and marriage, playing games, and drinking chai masala. It was such a simple yet wholesome interaction, and I think about it often. Meeting people that are unlike me helps me to broaden my circle of ‘normal’ and I can’t help but notice that my own trivial problems become minimized.
In your personal dating life, have you ever experienced any challenges with your partner in relation to your sex work? Are potential partners intimidated by your experience?
It’s difficult to say yes or no on this one. I’m extremely transparent in what I do. I’m on Tinder right now and it’s right in my bio! The downsides of this is that people are curious, and explaining (nearly justifying) my beloved industry is quite frankly, an enormous amount of labor. Especially when it’s someone who doesn’t last. Although in the same breath, I’ve been lucky enough to have several long term relationships while working as a companion, each with their own challenges, but all successful in their own rights. I’ve never had anyone be intimidated of my sexual experiences or anything of the sort but I have had partners on a lower income feel that they can’t measure up. Which is completely understandable. I think relationships whilst in this business take a considerable amount of transparency and communication, but they certainly are doable. As of right now, I have no trouble meeting men in my personal dating life, job withstanding. There are open-minded people out there. The world is shifting.
To what degree are your friends and family aware of your work? If they know about your profession, how did they react when they found out?
There’s a small handful of people in my family that still (somehow) do not know what I do. Although, 95% of them do, and all of my friends know. When I began showing my face online, I was comfortable with the fact that people may find out. I was included in an article for Vice Canada a couple of years back, which happened to make its way across numerous social media platforms, and onto the screens of my old colleagues, high school friends, and siblings. It ultimately took a lot of education, but funnily enough, the people in my personal life are my biggest supporters. I’ve certainly lost friends and it wasn’t easy changing people’s preconceived notions about sex work, but it eventually happened. My siblings often ask intelligent questions and say that they’re proud of me. Most of my civilian friends follow my Twitter and work Instagram, often shooting me funny comments on my content, and joke about booking me in advance for girl-time! I consider myself extremely fortunate to have such a solid circle around me.
What are some myths about sex workers that you’d like to help debunk and bring awareness to?
Ah, my favorite myth is that sex work is easy money. Everyone likes to jokingly suggest of becoming a stripper at some point only to lament ‘I could never!’ when actually offered a sex work job. In all seriousness, intimacy with a stranger is not easy. It requires a very particular kind of person. That aside, all sex workers (dancers, agency escorts, independent escorts, cam performers, and adult film actors) have their own particular and unique challenges. On my side, the volume of administrative work nearly exceeds the client-facing hours. Ongoing social media management and engagement, monitoring analytics, web design, editing one’s copy, photoshoots, content creating and editing, responding to emails / verifying screening, and the event planning required for longer dates, is all behind the scenes work that, generally speaking, isn’t universally acknowledged. Another myth on sex workers that bothers me is that we’re all damsels simply waiting to be saved, rather than the entrepreneurial boss bitches we are. There’s a stereotype that those that do sex work do so out of desperation. Disclaimer: survival sex work does exist and is completely valid. However, many of us choose sex work, frankly, because we love it.
What are some challenges with clients that you’ve experienced in your line of work?
The only challenge that I’ve found in this particular business is clients who begin to disregard (intentionally or not) the boundaries and invisible lines in the sand surrounding the nature of our unconventional relationship. Of course, every sex worker is entirely different in the boundaries they enforce; always communicate with them what is okay vs what is not. However, some basic ground rules are usually universal. An understanding that while it is a relationship, it cannot replace a conventional one. Chronic over-staying of the time booked, ongoing excessive chatting outside of dates, and shorting and/or ‘forgetting’ about the financial aspect are behaviors I think many of us would classify as an abuse of trust. Luckily, most of the suitors I spend time with are all extraordinarily considerate of these things, and I don’t run into problems often.
Do you have any advice for our readers about how they can kink up their sex lives and try something new?
Absolutely! After becoming a sex worker, my mind expanded and I was able to explore things I otherwise wouldn’t have explored. I’m so grateful that this line of work pushed me outside of my comfort zone. Thankfully, my job was the catalyst that opened my mind, but why wait for a reason? Start exploring and experimenting with new kinds of sex. Try new toys. Watch a different kind of porn (but pay for it)! Perhaps consider the idea of experimenting with new people, alone or as a couple. Explore kinks, find yours. Also, it’d be amiss if I didn’t say this — hire a sex worker! You might be surprised by how your sex life changes thereafter.
This article originally appeared in the February 2020 issue of ASN Lifestyle Magazine.