My Journey into Escorting

In the great tapestry of life, some threads are woven with profound purpose, while others are tangled in the kind of mishaps that prompt laughter even in the most formal of settings.  The question I get the most is: How did I get into this business? Well, kick off your shoes, grab a cocktail and settle in. Because here’s the long version.  

The Seed Is Planted 

This isn’t something that happened overnight, but with a colorful journey of events that include a TV crime drama, a series of unfortunate dating apps, a podcast host and a random Craigslist ad that all came together to get me where I am today.    

 

My story begins in the early 2000s when after my previous job had sent me galivanting (if you could call it that) around the world and I finally landed in sunny southern California. There was a hot new show everyone was talking about called CSI: Crime Scene Investigation (maybe you’ve heard of it).  I was watching an episode where there was this gorgeous woman, dressed head to toe in luxury lingerie walking in slow motion through a hotel penthouse corridor.  Her outfit lightly fluttering in the breeze while her perfectly coiffed hair bounced seductively with each footstep.  I remember thinking how glamorous she was, almost jealous of this fictional character of how bad I wanted to be her.  It was a very quick scene (where, of course, within seconds she ended up dead but that’s beside the point) but I was enamored.  To wear clothes like that, live in a luxury penthouse I could have only dreamed of.  I soon learned that, according to lead character Gil Grissom, she was described as a “high end companion.”  Wait, I thought.  Like a hooker?  All I knew of hookers were from movies like Pretty Woman, where they wore blonde wigs, had pimps and walked the streets trying to find the next white whale in a Lotus Esprit SE. Although I wasn’t so naïve to think they all ended in fairytale like in the movie with the man climbing up the fire escape with a red rose between his teeth, but I certainly never pictured them like this.  This looked so… glamorous.  AND they got paid to have sex all day! It was almost like a dream job.  But it’s not like I could tell anyone that THIS is what I inspired to be.  I was supposed to be on the path to be the next Barbara Walters. So, I filed it away and forgot about it.  Little did I know, the aspirations of my younger self would someday actually come to fruition.  

 

A West Coast Playground 

 

Fast forward a few years when a friend of mine from the early days of my wild child youth had also relocated to the SoCal area, determined to be the next star of stage and screen. Thus began my eye-opening education into the gay nightlife, where I moonlighted in the West Hollywood College of Wildness. Each evening spent in the neon glow of the gay clubs was an eye-opening experience; the liberated expression of sexuality was so pervasive that at times it made even me blush.  However, nothing really shocked me, but I will say those boys can be scandalous!  After a few years of onlooking this paradise of openness and free love it was time to move on, so I returned to the chilly embrace of Minnesota and quickly noticed a stark shift in the local mindsets. 

 

In California, sex was an open subject discussed with the same nonchalance as weather forecasts. People freely and openly talked about sex.  Nobody shied away from it and nobody was embarrassed about it.  We would hit the strip clubs on a regular basis.  I was asked to join in for a threesome like it was someone asking me over for coffee.  Meanwhile, Minnesota’s attitude towards sex seemed more akin to discussing nuclear deterrents: fraught with tension and best left unmentioned. Indeed, the discomfort didn’t go unnoticed. In the years I worked in the service industry, restaurant kitchens in California erupted with vulgarity as staff bantered in an “anything goes” conversations. In contrast, Minnesota was a place where the attitudes were as frigid as the temperatures. Why, I wondered, were my fellow Minnesotans so terrified of even the mention of sex?  But this was my new normal. So, I adapted to my surroundings, joined in with the masses, found myself a mate and settled in for a long (and boring) winters nap. Well, as it turns out, I was just looking in the wrong place.  

 

Single and Ready to Mingle 

 

After an arduous relationship marathon that would exhaust anyone’s sense of romantic stamina I, for the first time in years, found myself single.  By now,  times had changed and online dating was the new arena. But at this stage in my life, If I was going to join my peers on the path to holy matrimony, keeping on said path of finding a partner for “till death do us part” was the next logical step. I was pretty apprehensive about going it alone but with all my friends now busy building their families, venturing into the world of this kind of adult companionship felt more like a brave expedition with no Sherpa to guide me.  It seemed suddenly and without warning, dating had shifted to a chaotic battlefield where I navigated a sea of questionable online profiles resulting in stranger-than-fiction encounters. Frankly, it resembled a dumpster fire with more dates than a stale fruitcake—a sight both tragic and amusing. It didn’t take long for me to grasp that not every prince rides a white horse; in fact, some rode in on the back of a unicycle while juggling flaming torches.  My dating profile became a comedy of errors as I juggled ill-prepared suitors and ridiculous expectations.  This was NOT what I signed up for. I found myself flailing around, desperately trying to locate my soulmate, who I apparently thought would just jump out of my glowing computer screen, ready and willing to start a life adventure with me.  It didn’t take long before my pursuit of love quickly morphed into a stark reality: online personas are often just clever façades, and the whole scene should have come with an invitation that read “Welcome to the Shit Show.”  So, I decided on a new route.  

 

As the Millennials Would Say: YOLO 

 

After my gentle tumble down the rabbit hole of dating failures, I made an executive decision.  Instead of searching for Mr. Right, I decided to take a more cavalier approach—find Mr. Right Now! Live in the moment! Love’em and Leave’em! My new philosophy was simple: Why couldn’t sex just be a fun time between two consenting adults, no-strings-attached and completely devoid of expectations?  As long as we’re safe and not hurting anybody else, who cares? This is about the time in my life I honestly stopped caring about what other people thought of me. Their opinions?  Irrelevant.  If someone had issues with me and the way I lived my life, it was their problem, not mine.  They want to use my dating life for fodder or gossip? Fuck it. Then it was their cross to bear. Kudos to me for living rent-free in their heads while I’m over here, living each day as if it were my last. I mean, it’s only life after all, right?  

 

I joined sites like adultfriendfinder and fetlife and perused the craigslist personals.  Let’s just say my life wasn’t lacking in entertainment.  Some of these meetups I ran for the hills. Some are still my friends to this day. My California friend moved back and joined me in my quest to wreak havoc through Minneapolis, and we discussed how convenient it would be for us if hotel rooms had revolving doors – one spin and I was tapping out of one rendezvous straight into another without any of the awkward, “Are you staying for breakfast?” conversaion.  It was during this time that I was introduced a whole other community of like-minded people in Minnesota. And unbeknownst to me, they were hiding in plain sight.  

 

I Come Out Swinging 

 

It started innocently enough with a nudge from a guy I had been seeing towards a…shall we say…different kind of dating website. Lifestylelounge became my new go-to stop for an entertainment venue.  This world wasn’t exactly new to me, but this wasn’t California.  I was in a different venue altogether. So, I cautiously dipped my toes in, a few flirty messages here and there but nothing real substantial—until a couple reached out to me, the wife’s message promising a safe haven of normalcy. Our subsequent meeting revealed a refreshing honesty that left me blinking in disbelief. Compared to my past, where accusations of infidelity flew like confetti at a parade, this couple’s openness about desires was a revelation, and it was refreshing to meet a couple you could end the night in bed with just as easily as if they invited you over to a family BBQ. 

As I eased deeper into the swinger scene—one-on-ones, hotel parties, costume parties, house parties, nudist resorts, hedonist resorts, dungeons, you name it—I found that there was an advantage to having sex being a pre-discussed topic. The awkwardness typical of first-date fumbling was blissfully absent; here, everyone came to the table with intentions clearly laid out. And being a single female—or as some would call a “unicorn” amongst the community—was like being a kid let loose in a candy store. The world was my oyster, and I took full advantage.  

 

Then one day, an off-handed comment got me thinking.  Sitting at the Saloon while dishing on our latest escapades, my long-time accomplice turned to me and wondered aloud, “Why don’t you just make money doing this? I mean, you’re doing it anyways.” Making money doing something I was already doing? Genius! Then I remembered that titular TV episode from so long ago.  Maybe this was my chance to fulfill the dream job of my younger self?  I never thought it would actually happen. But alas, I said I wished I could but I didn’t know the first thing about this type of entrepreneurship. After all, I could barely manage the schedule of my dating life—how was I supposed to navigate the complex world of sex work?  Well, as it turned out, with the help of two anonymous strangers it wasn’t as hard as I thought.