The Day I Prostituted My Self For The First Time
1996Crash! A package of uncooked spaghetti hits the wall as I grab my winter coat and make a dash for the garage.
Everything I need to survive in this moment is in there.
It’s mid-January, and a massive snowstorm is hammering Southern Ontario.
I’m from Scarborough—the east end of Toronto.
If you’ve lived through a southern Ontario winter, you know the type — it’s more like Fargo than fairy tale most of the time.
The wind was howling, and the snow was whirling and parallel to the ground at speeds unknown. It was a blizzard as you’d see on one of those reality survival shows like ALONE.
Some snowfalls are lovely in Southern Ontario — big, lazy flakes drifting down like parachutes.
This wasn’t one of those.
This day—the day I prostituted myself for the first time—was just underway for me, and I had just been booted from the house after another brutal fight with my possessed girlfriend.
Yes… she was possessed… ughhhhhh… if only you could have only seen her, you’d agree.
SLAM!
It’s me this time; I slam the inside door that goes from the house to the garage—I have to get away.
There are only a few things in the garage, including my 1987 yellow convertible Corvette. I had her covered for the winter. Oh, how I longed for summer when she would have the ability to thrive once again—winters and Corvettes are adversaries.
I also keep my tool bag in the garage; music, costumes, and G-strings—yup, we actually wore G-strings—oh gosh—see below 😔.
NOTE: The girl on the left is different than the girl on the right. The girl on the right was a friend (and still today—we spoke recently in fact), and she approved this picture and the following. This was her stagette (or bachelorette), and there were about 8-10 girls gathered at the maid of honours house for a whoop-up. It’s not uncommon to do these parties before going to the club. We do 2 or 3 songs and have some fun. About 10 minutes after this picture we banged in a bedroom beside the exit. This is also not uncommon. About 10 days later, she was walking down the isle — it didn’t work out in the end.
…back to the story…
…it was still light out, though dusk was looming, and the snow was already a foot or so deep.
I bundled up and left the house dressed like a scientist in Antarctica, carrying my tool bag over my shoulder, and hope in my heart.
I galumphed through the storm and called my agent on my brand-new Motorola flip phone.
“I need some work tonight,” I told him. “I just got kicked out, and I’ve only got a hundred bucks in my pocket.”
“I’ll call you back.” Click.
I flip it open again and start dialling.
“Hi, Ma, I love you. Can you put Dad on?”
“Where are you? Tell me you aren’t outside.”
“I’m outside.”
“Has that lunatic kicked you out again?”
“Yup. Can I borrow Dad’s station wagon?”
“Of course.”
“Only a fool or an Eskimo would go out in this. Where are you going?”
Word choice tip: Don’t use Eskimo anymore. Use Inuit.
“I said, where are you going!?”
“Sorry, Momma, I’m going to Hamilton to work.”
“Oh, crikey… you’re gonna give me a stroke.”
My mother was a renowned sofa-based stroke researcher—also fluent in diabetes, heart and kidney disease, and how to deal with a 25-year-old who can’t seem to keep his shit together—or at least stop someone from kicking him out in a snowstorm—or, at the very least, get a winter-beater.
winter-beater: noun: a piece of shit old car, likely rusty and full of holes, that one uses in the winter to save their yellow, convertible Corvette from the ghastly catastrophes that Ontario has to offer from December to May.
…back to the story.
My agent called back: there’s a gig in Hamilton, which is two hours away—snowstorm or not, I’m going.
I white-knuckled it along the northern banks of Lake Ontario, finally rolling into The Foxes Den—a seedy basement, downtown strip club.
It’s a dead Thursday night: four strippers, a bartender, and a server. But I was happy for the $100 pay.
When it was my turn to go on stage, there were exactly nine girls there. If it weren’t for the snowstorm, there would have been double that—hard times in the Hamilton male stripper scene.
I spotted two women having what looked like more fun than they should be.
They were cheers-ing and laughing somewhat hysterically, and I remember automatically thinking one of them must be a comedian, or farted.
When it was my turn to hit the stage, I noticed their attention turn to me.
I was getting googly-eyed (verb). Eye-fucked. Evaluated.
Of course, I played into it—it was my job, after all.
Then the bigger girl came up on stage and tipped me $50. A stray from the standard $2 or $5—but certainly very welcome.
…before I forget, just for visuals—when I say “bigger,” she 250–300 pounds—and very sweet. Her name was Bernice.
When I came off stage, she asked me for a lap dance in the corner, which includes all forms of foreplay and is not limited to include intercourse—and also dependent on what the client wants, what she looks like, and how high my sex drive is that night.
The lap dances were a standard $10 per song, and we would go to a designated dark corner to “get down to business.”
She handed me $100, then bought me a drink, and we got underway.
In the corner, I did the standard probing: …
(…not that kind of probing, you perverts)
I was probing with my words, to get to know her.
What does she do? Where’s she from? What’s the occasion? Oh ya… and uh… what’s her name?
Every stripper must always remember that this is a business transaction; a service like getting a plumber to fix your leaky pipes (pun intended).
I need to know what she’s looking for and ask about her budget without asking “what is your budget?”
It’s a business, but you must be colloquial with your words—especially in Canada’s steel town.
col·lo·qui·al /kəˈlōkwēəl/ adjective (of language) used in ordinary or familiar conversation; not formal or literary. Note: It just dawned on me that the word colloquial is the exact opposite of it’s meaning. I can’t think of any other word that can boast that at the annual Oxford word-of-the-year banquette
🎤Communication Tip: Silence Sells • Every interaction is an opportunity to connect with someone. Listening is key to connecting. • If you want to get to know someone, or just need information, you should be listening 80% of the time. Talk 20%. Not to be polite—although that is always important—but rather, strategically. • Don’t just listen for facts. Listen for emotion—their emotional state will tell you much more about them than what they are saying, (more on that in a following newsletter). Why it lands: Silence creates an awkwardness for most people.
…back to the story.
By the third lap dance, she told me she'd just won $50K on a scratch-and-win bingo ticket.
The over-excitement now added up.
A few more pussy rubs with my knee and she hit me with the six-inch question.
"How much for the night?" — said with a blush and a cute little smile.
I stepped back, smiled, and paused.
Here's the thing nobody tells you about shyness — it's magnetic.
She looked down when she said it. Couldn't hold eye contact. Bit her lip a little. She wanted something and was almost too embarrassed to ask for it.
And that was it. That was the connection.
There is nothing more disarming than someone who isn't trying to be anything.
🗣️COMMUNICATION TIP: — Shyness (or perceived shyness), can be a superpower. You can use shyness as a way for to gather information on your counterpart. • Shyness lowers perceived threat. Low threat increases trust. • Take a breath. Pausing before answering signals control, not uncertainty. • Observer advantage. Shy reads the room while loud tries to own it. Observation beats domination in any negotiation. • Why it works: People don’t relax around confidence. They relax around calm.
“It’s usually $1,000 bucks for the boyfriend experience,” I say, “…but I do have a ‘bad weather, half-price special going on right now.’”
We both laugh.
boyfriend experience: noun-phrase (informal) • it’s kinda in the title—unlike a sex transaction from decades past, the boyfriend experience includes, but is not limited to, holding hands in public, kissing, french kissing, rubbing on the outside of clothing, rubbing on the inside of the clothing, blow jobs with no condom, fucking with no condom, and (maybe) bum sex—if they wanted to be choked or pissed on, of course that would have been extra.
annnnnd…we’re back
The night wraps up, and I tell her and her skinny-legged friend to meet me at the top of the back stairs.
We head outside, and believe it or not, it’s still snowing—it feels much warmer because the wind has died down, and now it is starting to feel like one of those fairy-tale snowfalls with the parachutes on.
However, the only parachute going on tonight has Trojan medium/small written on it.
We drop the skinny girl off.
Note: For visuals, when I say “skinny girl,” I mean like a person who either has the metabolism of a leaf-cutter ant or smokes a heck of a lot of speed—I’m not saying she did; I’m just saying that’s what she looked like. She was very polite and lovely.
We drive the snowy, deserted streets of downtown Hamilton for what seems like not very long until Bernice navigates us to a small strip of three or four motels.
I remember having to choose between the Faded Star Motor Court and the Golden Mile Motor Court. I don’t side with pessimism—I chose the Golden Mile Motor Court; although in hindsight, the Faded Star seems more accurate.
She paid for the room, of course. The customer always does.
NOTE: The first girl I dated when I started stripping was also a stripper and would charge some of her clients on the side for sex. We lasted six months. That’s how I know: the customer always paid for the room— makes sense.
I tell her to stay in the car and stay warm while I get us a room.
She pulls money out of her wallet to hand it to me, but I refuse.
“We’ll worry about that later,” I say. After all, isn’t it what a boyfriend would do? (A good boyfriend would, of course, pay too. But hey, it’s a business, and I feel like I’m doing pretty well for a rookie.)
I jump back in the car and brush the snow off my face. Holding the keys up, I give her a flirtatious smile.
“Is it on the first floor?” she asks with a nervous voice.
“Not just because of the ice, but… you know… I’m kinda a bigg—”
I cut her off.
“We’re just a few cinder-block units over. Let me take us right up front.”
I can’t help but think to myself, holy mother of God, Jesus Mary and Joseph! I’m going to be a great boyfriend one day.
There’s only one problem—I already am a boyfriend, and I must be horrible at it if I keep getting kicked out.
I go around and open Bernice’s door, and cover her from the dangers of the elements of Mother Nature—and potential harm from the locals.
I enter the room first, holding her hand in tow. A gentleman would always enter an unknown room first—especially when the room is painted cinder block.
It smells like cigarettes and what I’m having trouble deciding between either mould or pussy and dicks.
She sits on the edge of the bed while I take off my jacket and start to get comfortable.
Then it dawns on me that I don’t have an inkling of arousal in me. How am I gonna pull this off?
As luck would have it, I go over to the television to find a music channel, and when I turn it on, there are two hot blondes sixty-nining. Perfect. I feel something moving in my pants.
I go over and start kissing her while occasionally glancing at the blondes—now they are scissoring.
I’ll skip the romantic details.
So, we fuck and do all the necessary prostituting.
The night was a success. She had a couple of orgasms and seemed pleased with my performance, and made me feel as if her money was well spent.
I make it back to Scarborough… it’s almost 6 a.m. and still dark out.
I’m locked out, remember, so I go in the same way I left—through the garage.
I enter and there she is. The love of my life.
As beautiful as ever, I walk over and take her top off. Then I reach down and stroke her rim.
She always gets me horny, but there is no time to take her for a ride. I’m tired.
I pull the cover snug, step away, and flick the light switch off.
“Sleep well, my beauty,” I say to my yellow convertible Corvette—“see you in spring.
And slide over: I’m getting a winter beater.”
Until next week, take care.
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