Just a Regular Working Girl: Moralistic Values Gleaned from my Time in Chicago’s Seedy Underworld

Moral 35: Buying Condoms is Always Awkward. Buying 192 Condoms is EPIC Awkward.

 

“We’re going to have to refill the condom bag,” I suggested.

“Geez,” said my boss, Caroline. “I wonder how many expired ones I’ve used in the past month or so.”

“Don’t you check the dates before you put them on?” I said. She was an escort, and I was her assistant. I did her shopping and cleaned her house. I’d come from a pretty sheltered Catholic upbringing, and if I’d ever given any thought to the lives of escorts, I would have assumed that condom safety was Escort 101.

Caroline was disillusioning me about a lot of things.

She shrugged. “Sometimes. I don’t want to spoil things in the moment by digging through the bag. And I don’t want to toss aside old condom after condom in front of the client—he’ll think I’m irresponsible.”

“Well, we wouldn’t want to give him the wrong impression,” I said.

She caught the sarcasm. “What did you say?”

I played it off as though I’d meant it honestly. “I mean, look at all the condoms you have here. Safety is a big deal to you.”

This wasn’t entirely true. Caroline talked a big game about safety. But she didn’t actually walk the talk. If she cared that much about safety, she wouldn’t have become an escort in the first place. Nor would she use expired condoms. And she had confessed to me that sometimes, if the client asked, she didn’t use condoms at all.

 

Moral 33: A whore’s concept of safety is sketchy at best.

 

The suspicion faded from her face and I heaved an internal sigh of relief. I had to get better at biting my tongue. I never should have said that thing about wrong impressions.

“You’re right,” she said, her image of her own responsible nature momentarily restored. “So we should get more condoms. Go to Walgreens and get . . .” she assessed the contents of the bag. “. . . 300.”

“300?” I said, trying to sound like this was a very normal request. Like I was not at all surprised or nervous. But how many packages would that be? Even buying one package of condoms sounded intimidating. I was only 20 and I’d never done anything like that before.

“Yeah, I don’t know how many packages that is,” Caroline said. “Sometimes you can get them in boxes of 36, so do that if they have them. If not, the 12 packs will be fine.”

I took out my journal and pen. It was the closest thing to armor I had. “What kind?” I said.

“Trojan,” she said. “And some Durex. Make sure you get plenty of all sizes. And if they have hypoallergenic, get those too. And get some KY Jelly. Get like, 20 bottles of that.”

Oh my god. This wasn’t happening.

She had a client coming over. That meant it was time for me to leave. I put on my coat, ventured out into the Chicago winter, and headed for Walgreens. I decided the best way to do this was not to think about it too much.

My first dilemma came when I walked in the door. Well, no. My first dilemma was that I worked for a whore and had to buy 300 condoms. My second dilemma was whether to choose a basket or a cart. How much space would that many condoms take up? I had no idea. I chose the cart.

Then I had to find the condoms—without accepting the assistance of the creepy employee with the blue vest and greasy hair. It didn’t matter. He saw where I was going and leered anyway.

There were no 36 packs. In fact, there seemed to be a limited amount of 12 packs. I counted, and there were only about 16 boxes of condoms there. I was no good at mental math, so whipped out my trusty journal and imagined my old math teacher, Sister Mary Katherine, saying,

“If we have 16 boxes of condoms, and 12 condoms in each box, how many condoms do we have total?”

“192,” I told imaginary Sister Mary Katherine. Nowhere near 300.

“Well,” said Sister Mary Katherine, “what do we do in a situation like this?”

“There’s only one thing,” I said, and proceeded to put every box of condoms they had in my cart. I also took every package of KY Jelly they had, since there were only 12 and Caroline had wanted 20.

 

Moral 34: Nuns really do want to help the misguided . . . even if they’re misguided themselves.

I avoided the aisle with the creepy blue vest guy, and went right up to the counter. The woman in front of me glanced in my cart and then pretended she hadn’t.

Then it was time to check out. I had been trying to think of something clever to say about my cart full of condoms and KY, but there really was nothing. I thought if I tried to say, “They’re not all for me,” or “I’m doing a project,” it would probably have just sound like an excuse for being a huge slut.

So I didn’t say anything. I just stood there blushing like the most awkward girl in Chicago, feeling ashamed of the fact that I was ashamed, because I should be more mature and worldly, and hoping that someday I wouldn’t feel like this. Someday buying condoms would be fine for me, right?

And the girl at the counter didn’t say anything either. She just scanned box after box after box, and when it was time to start a second bag, she did it as coolly as if I were buying 16 bags of gummi bears.

Looking back, it was probably no big deal for her. She probably assumed I was doing some kind of project, and might even have believed what I told her. But I was self-conscious, as most people are when they’re buying condoms—whether it’s one box or 16.

 

Moral 35: Buying condoms is always awkward. Buying 192 condoms is EPIC awkward.

***

L. Marrick is a historical fantasy writer and freelance copywriter. She waxes poetic about swords and the Renaissance Faire at her author blog. She looks all professional-like at her copywriting site. She eats too much chocolate and still doesn’t believe downward dog is supposed to be a restful yoga pose. You can connect with her at either of her websites, and follow her on Twitter .

It wasn’t anywhere near 300, though. I was lucky Caroline didn’t send me back out to the Walgreens on the other side of town.