My Other First Time: Losing My Whoreginity
Warning for graphic description of sex work
The first time I fucked someone for money — and by this I mean, for a wad of hard cash in my palm, not for dinner or liquor or lines of cocaine, as I’d been doing for months prior — was in 2005. I was 21 and living in a sleepy Minneapolis exurb, at the tail end of a marriage in which I cheated brazenly, in which my husband was powerless to stop me. I was reckless, relentless. After a lifetime of being the ugly duckling, I had finally blossomed, through stimulants, starvation, and a “slutty” new wardrobe, into a mediocre-looking, histrionic, sexually compulsive swan.
But I was poor. Oh, was I poor.
I’d tried college for a semester on a full-ride scholarship and flunked out spectacularly. I left entry-level jobs after a week or two, huffing and puffing, my middle fingers raised in the air at bosses who dared challenge my authority. Creditors hadn’t yet discovered my complete unwillingness to pay bills, and flung high-interest credit cards at me like candy at a parade. I maxed them out with the streamlined efficiency of an addict, buying a computer I never intended to pay for and a car I neglected to maintain, making indiscriminate ATM withdrawals to support my blooming fondness for pills and powders.
This Monopoly money dried up as quickly as it had materialized. I began living entirely off of the naiveté and kindness of my cuckolded husband, who was six years older and a lifetime wiser (in finance, if not in love). But after sleeping with one too many men in our bed, forcing him onto our sofa for the night like a bad dog, I found myself without access to his bank accounts. We barely spoke of our disintegration, though the fog of it hung heavy in the air between us. If I could have left then, I would have. I had less than five dollars in change to my name and a husband whose tolerance I’d exhausted.
Still — this isn’t really why I did it.
My decision to put an ad on Craigslist that night could be roughly broken down as follows: 50% impulse, 30% desperation, 20% curiosity. Yes, I was riding the waves of an amphetamine high. Yes, I needed an immediate influx of cash. But most importantly, there was something intangibly appealing about the idea of being a whore.
Online hookups were old hat to me. I’d been there, done that, gotten the hickeys and handprints on my ass to prove it. I had placed “wannafuck” ads on Craigslist before, though never for money, and turnaround time was minimal on most of them — from email to sex in twelve hours, five hours, three. I liked the rush of it. I liked that anyone would want me that badly, that I was even worthy of that kind of desire.
So to think that someone might pay me — me, the forever fugly chick, the girl who would give a thank you blowjob to any man who called her pretty — for what I’d been giving away for free for months? I had to try it. I had to.
I didn’t even know what to call what I was attempting to do. I didn’t understand how something so illegal could be so shamelessly advertised, or what rules would govern me once I made the leap from amateur to professional. Hasty Internet research led me to the following conclusions.
1) I must never kiss a “john” on the lips, because lips are for lovers only,
2) The money is for my time, not sex (but really, it’s for sex),
3) I must never discuss or acknowledge the money — never, not ever,
4) I must keep my stash of cash tucked deep inside my bra, so he cannot steal it back,
5) I must learn to roll a condom on secretly with my mouth, because
6) if he notices the condom, he will protest and demand to fuck me without it, and
7) in order to be a hooker, I must dress the part impeccably.
This is what my ad said: Cute, fun girl looking for GENEROUS$$ friend tonite. I am very open and kinky Have pics. Email me now!! Within fifteen minutes, my inbox was teeming with responses. They ran the gamut from lazy greetings (hey) to violent, elaborate fantasies (YOU ENTER MY ROOM. IT IS DARK AND I AM WEARING A MASK. I PUSH YOU TO THE GROUND AND FUCK YOU IN THE ASS HARD AND YOU TAKE IT LIKE A GOOD SLUT…)
These, I ignored. I replied to all the rest with a picture of myself. This cut down the number of interested parties significantly, and soon I was left with Randy, a chubby retail clerk who’d sent me his own photo and pledged to be extremely generou$!
I wrote down Randy’s address and contemplated how a prostitute should dress for her inaugural trick. I settled on a short black slipdress through which my underthings were quite visible, lace thigh-high stockings so tight that my leg fat ballooned over the tops like sausages bursting from their casings, and a pair of black vinyl go-go boots I’d worn to a screening of Rocky Horror Picture Show in high school. I clasped a black beaded choker around my neck, applied an excess of very red lipstick in the bathroom mirror, and forgot to blot with a tissue. I stared at myself in all my trashy glory. Yes, I thought. You’re a whore. You can do this. Let’s go.
Randy lived nearly thirty miles away. I begged gas money off my husband, who knew what I was up to because I told him — he could barely look at me. I drove my rusty, oil-dribbling, bumper-stickered Honda Accord. But right then, on that stretch of dark highway, it felt more like a Jaguar: sultry, audacious, powerful.
“Jesus, what are you wearing?” were the first words out of Randy’s mouth when he saw me. I looked down at my slip-covered body, and in the harsh fluorescent light of his apartment building’s hallway I could suddenly see my nipples through the sheer fabric of my bra, every chubby roll around my waist, every individual scallop of lace on my bargain-bin thong underwear. He glanced down the hallway, then at me again with a half-laugh, half-scoff. He tugged me gently inside. He shut the door.
I studied him, heart pounding. He was not unattractive. I could bang him. He was sweaty, sort of, but so was I. A bit too hairy for my tastes, maybe, but he was young and his eyes were friendly and most of his teeth were in proper alignment. A decent smile.
I smiled back as violently as I could, baring my canines and most of my molars. I was shooting for fuckable, yet menacing, and it must have worked, because he took a step back and fumbled for his wallet.
“How much?” he asked.
I froze with the stupid grin on my face. Rule 3. Don’t talk about money. Don’t look at it. Don’t even think about it.
“Muh?” I said.
“Your rate,” he said. “How much?”
My go-go boots and I ignored the question and waddled into the kitchen. I pretended to study his refrigerator magnets. Randy had a lot of refrigerator magnets.
“Here,” he said, following me, flapping a thin fold of bills. “Do you want it now, or…?”
Or what, I thought, you’ll drop it in the mail for me next week? Of course I wanted it now. I grabbed at it hungrily, and without looking at it or acknowledging its existence, turned away from him and shoved the money deep into my bra. My slip was so thin you could see the crease of the bills.
Randy led me into his bedroom. It was small and cluttered, but not dirty, though it smelled of newsprint and chronic masturbation and Lysol. He pulled my slip over my head, then fumbled for a long time at the back of my bra, with both hands, until it unsnapped or maybe broke. It fell to the ground, but the wad of money was affixed sweatily to my breast; horrified, I peeled it off and flung it into a dark corner of the room.
“You’re very pretty,” he said.
“I don’t kiss on the lips,” I said.
“Okay,” he said.
Afterwards I sat in my car and wiped my face with a napkin, trying to remove the red lipstick that had migrated to my nose and chin when I’d attempted — failed — to roll a rubber on Randy with my mouth. I’d pierced the latex with my teeth, scratching poor Randy with the sharp edge of my incisor in the process. I used my hands to apply the second condom, but I was so flustered that I put it on backwards and it wouldn’t roll down.
My third try: the proverbial charm.
In my fist I held my paycheck: three $20 bills still damp from my cleavage sweat, plus an extra $20 Randy had slipped me at the end for my “hard work.” It was more cash than I’d seen in months, and if my eager, awkward, very pretty body was worth more than eighty dollars, I did not consider it. I just fondled the money, stared at it, slid each bill slowly between my fingers, breathed them in, squeezed the life out of them, and felt a heat wave of adrenaline wash over me, better than any drug or drink or endorphin or lover. What that money meant — what I knew from the moment it was mine — was this: I would never need a lover again.
Written by Sadie Palomino