My College Roommate Was Pretty Woman

by Jackie Linder Olson
Originally Published: 
A female roommate's legs with high red heels lying on the bed while partially covered with a blanket

My college roommate was an escort. I could call her Candy or Lola to be cheeky, but the truth is she had a Jennifer-ish name and looked like every other 19-year-old in my economics class in her Jordache jeans, Guess tops and flip-flops. She was always performing magic with her hands and promised to teach me a few tricks, but little did I know what she had up her sleeve.

Within days of school starting, she finagled her way into living in my apartment, and we settled into a rhythm, passing each other in the shared bathroom and leaving Post-it notes about our study schedules. But then I started noticing strange things. For one, she had two pagers (yes, this was 1992), but really, who needed two pagers? Secondly, she kept all kinds of crazy hours and I’d see thousands of dollars in cash piled on her dresser.

Her true profession was exposed when she called me at 2 a.m. to pick her up from a local hotel one night. “Bring me sweatpants and Nikes,” she commanded. I did, and in room 805, she explained to me that the cops were waiting to arrest her. Her john had just left, and she needed me to help her sneak out unnoticed. Apparently, you can’t do that in hooker attire (remember, this was before ubiquitous security cameras and cell phones). Jennifer spilled her guts, and I was horrified and fascinated at once.

I lived with Pretty Woman.

Jennifer allowed me behind the smoke and mirrors of her life and shared her secrets. A strip club was her bait job. She hooked them working one night a week as a cocktail waitress, and it was a calculated process that went like this:

Step 1. She’d charm the men, letting them know she was slinging drinks to pay for her education. She was a good girl and couldn’t take off her clothes like those nearby strippers.

Step 2. They’d offer to pay her for sex—kind of like a college scholarship program. Step 3. She’d act offended, but offer a small glimmer of hope. Step 4. They’d keep increasing the amount they would pay. Step 5. Once the price got high enough, abracadabra! She’d give them the ultimate fantasy of being her very first customer.

The service she provided was sex, but the illusion was what they paid the high price for: the good girl with the heart of gold…or was it the golden vagina?

Her client pager went off 24/7, which explained the second pager reserved for her family. Airport runs seemed to be popular. They’d call for a blow job on their way out of town or when they had just arrived. She was Super Shuttle’s biggest competition.

Over the next few months, I met some of her local regulars, all wealthy, older gentlemen. She dragged me along to the finest restaurants and events, not wanting to be bored to death during her working hours. “He’s so wrinkled and gross. I hate his laugh,” she’d whisper in my ear while flashing him a million-dollar smile.

I learned that “never” was a magic word. She would tell them: “I’ve never had an orgasm,” or “I’ve never done a private lap dance,” or “I’ve never slept with a married man.” And the real moneymaker: “I’ve never loved anyone else before.” That one would get her a credit card or even a new car. The only thing on par with “never” was “only”: “I only wear my crotchless panties for you.” And it got even more twisted. She had a boyfriend–like a real, our age, going-to-med-school boyfriend–whom she adored. Yep, this was dysfunction at its finest.

Our friendship ended as quickly as it started, lasting just under a semester. I came home from school one day, and she was sucking on the fingers of a guy I had just started dating. I kicked him out, which was a no-brainer, but then I saw her. I truly saw her for the sociopath she was, because she said, “I’ll never do anything like that again. You’re my best friend, and I only love you.” I knew in that instant of “nevers” and “onlys” that she was a user, and if I didn’t end the friendship, I was going to get burned. Worse, I could end up in a dangerous situation.

She dropped out of school, and I never saw her again, although thanks to Facebook, I know she’s been married twice. Those suckers had to have paid big time.

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