by Dana May
I came across the ad while cruising the W4W Craigslist page in the basement of my law school library. I clicked on “Looking to Start a Lesbian Escort Service,” not bothering to check over my shoulder for any potential witnesses. My queerness, at that point in my life, seeped out of me like sap from a tree, an internal truth made material in the form of flamboyant flannels and a rat tail. I had no shame and nothing to hide.
The posting read like a start-up looking for investors. The writer pitched her vision for the enterprise: Vermont’s lesbian community renting out dates for “social gatherings, companionship, and more”. I was scouring the backwaters of internet dating because I lived in a state of bucolic plague, in a town without a street light, much less a gay bar or another eligible single queer woman to date. I could see these other women, the targeted market for this business, as lonely as me, tucked away in small Vermont hamlets such as my own, or in the metropolis of Burlington some 70 miles away. A couple of years of living in the Green Mountains and I had come to believe that most queer Vermonters had already coupled up, too busy remodeling their Victorians and running their goat cheese farms to hang out in numbers large enough to be called a community with the likes of me. I longed for the elements of gay life I took for granted in cities, like themed dance nights and making out in dark corners. This potential demographic beyond monogamist monotony intrigued me. I responded to the posting primarily out of a sociological curiosity.
I met the writer of this craigslist ad, a middle-aged woman named Ali, in one of the many microbreweries in Burlington. She maintained tragically frosted tips muted by a trucker cap, paired with faded jeans that slung on her hips and a vintage denim Western Shirt with embroidered red roses on the front yoke. She told me soon after ordering the first IPA that she was “the Barbara Hammer of stained glass” and said she had slept with “or at least knew” every lesbian in the tristate area by our second round. It took until the third drink for her to get around to talking business.
“It’s just, here I was, down for a show in SoHo, some queer art crafters exhibition that an ex from my Bard days was curating, and I am seeing all these old fags with their cute little twinks and thought, ‘why not us?’ ” She paused, waiting for me, her question not entirely rhetorical. I smiled in affirmation. What else was I there for?
“Who are these Johns?” I asked with a lightness in my voice masking anxiety. She frowned. She addressed me with the made-up name I had given her.
“It’s not like that, Alex,” she said with the profundity that comes with multiple pints, “these women have feelings.” She looked away from me. “It can be so hard to find someone up here.” To that, I nodded.
Ali saw herself as a commissioned “low expectations” matchmaker for the community. I would get 80 percent of the cut, which seemed reasonable, realizing then that I had not researched the salary range for an entry-level position in this field beforehand. She offered me the job after she tongued my mouth outside the bar on Pearl Street, followed by a “sorry about that” while looking at the ground. She did look me in the eye to say goodbye and to “lose the rat tail.” I didn’t consider this order until she texted me a few days later about my first client.
“Second thought on the rat tail. This one might be into it. I’ll ask.”
“What should I wear?” I texted back.
“What do you mean?” You know damn well what I mean Ali.
“Does she like femme or butch?” I asked.
“Hard to say with Deb. She just got divorced. I’d say wear a dress but it’s been too cold and messy out.” I appreciated Ali’s sensitivity towards performing femme in prolonged Vermont winters.
“Just be hot and attentive.” A few minutes later, she texted, “Keep the rat tail, she used to have one in the 90’s. She will probably think it’s cute. lol”
I met Deb at a small hotel restaurant in Hancock, a midway point for both of us. Her WASPy navy blazer and chinos clashed with her motorcycle boots, but not her Princeton fade. I walked the line of Northeastern gender expression with a vintage green puffy vest and a tinted lip. Deb stood up to greet me after waving me down in the near-empty wood paneled restaurant. She went in for a hug as I put my hand out, a momentary awkward impasse before I let her embrace me. In the silence following our introductions, I realized my responsibility to make this pleasant for her. I complimented her on her bolo tie.
She noted my rat tail and proceeded to put on reading glasses in order to find a picture of her younger self. She looked up from her expensive-looking wire half rims to carry on the banter between us, her shyness melting into a subtle suavity. She smiled before showing her phone to me. In it, she posed tough, but had a grin holding back a laugh, her eyes covered by black wrap-around sunglasses and a little braid going over her shoulder. Her hair was the same mousey color as mine. I expected her to make a comparison between us.
“It went all the way down my back.”
“Why did you grow it out?” I asked.
“Oh, it was the thing to do then, I guess. Why are you growing yours out?” Funny that I didn’t have an elevator speech for justifying this haircut. Did my male law school peers have a reason for their long, full beards?
“What else is there to do?” I shrugged. She laughed.
Deb asked me about my life but got carried away quite easily with talking about her own when I evaded her questions. By the time I had polished off my cheeseburger and sweet potato fries, she had already confided in me about the used condom found in the trash that marked the disintegration of her marriage, along with her hopes to purchase a pottery kiln with the settlement funds. I expressed empathy while making mental notes of the clichés to relay to my friends later.
We stepped outside into the bitter evening and surveyed the settled but barren land, unsure what was supposed to happen next. I struggled to come up with a charming way to ask for my money. Before I could complete the transaction, she pointed to a neon lit bar down the street and offered me a nightcap. She kept talking while I listened to our boots crunch on the mix of salt and snow. Inside another wood paneled room, I saw a cribbage board sandwiched in a precariously stacked pile of board games and Jenga sets in the corner of the bar. We played a round while she talked about her childhood. She gave me my cash after we fucked in her Subaru. It was cold but spacious in there, and she gave like she had something to prove. I drove back to my apartment feeling full and satisfied.
The next day, I met with my friend Laura to study Admin Law. Afterwards we drank at one of the two bars in town, the one with windows. Laura shined at the top of our class and carried herself like a debutant. Despite this, she reserved a part of herself for whiskey in my company. I burned to tell her about getting fingered by a middle-aged woman in a town hall parking lot, but needed to test the ice before I could walk with complete honesty.
“You wouldn’t believe what I saw on Craigslist the other day. Someone’s trying to start a lesbian escort service!” My friend, meticulously beautiful and hopelessly heterosexual, broke her observation of some classmates navigating the snowy sidewalk across the street to look at me straight on.
“You’re not thinking of doing that, are you?”
“Of course not!” I scoffed before I could give myself away, “but can you believe it?” I looked at my reflection as I talked, my effort to steady myself into nonchalance. She remarked about the bowtie our crim pro professor wore last week, like I had made only a mere observation of the weather. I said that I loved his commitment to wearing bowties and his extensive collection, and began to pontificate on how their colors and patterns could predict his mood, when she stopped me.
“You wore a bowtie the other week.”
“Yes, I did. I found it at the basement thrift store.” I began to smile thinking about it, but saw in her face an inherent disapproval that dampened my joy.
“You know, you would be one of the prettiest girls in school if you didn’t dress so gay.” I think about this from time to time, when I see myself in windows, both gay and beautiful. I wish I had said something clever but devastating. I responded with a timid “thank you”, instead.
Ali called me up later that evening. She caught me at my desk, where I sat writing drafts of what I planned to say to her as part of my resignation. She reported Deb’s praises of me and how she wanted to set up another date soon, her voice filled with a single-minded excitement.
“But you know what. Keep them wanting. I got somebody else in the meantime. A friend of a friend. I don’t know her well but she says she’s cool. Met her at a bar recently and she wanted to know when you were free.”
“Ok,” I said, “you know what, I got a lot of things going on,” I couldn’t read my notes much the same way I choked during my moot court tryout. “Didn’t anyone else respond to your ad? You know, to do these dates?”
“She really wants to strap and fuck a girl real good”
“You said she’s in Burlington?”
Ali sent me two pictures of Bec before I drove up to see her that weekend. Both were selfies of them in a dimly lit microbrewery, arms around each other like old chums. From what I could make out, Bec looked about my age, androgynous, with high cheek bones and deep set eyes. This stirred me into character as I left my apartment in a vintage dress. It was hard driving in those heels.
I couldn’t discern at first whether Bec was a world-worn man or my date as she approached the table. Even soft, new-American restaurant lighting exposed the grey weariness of her skin. I fed my disappointment with a salad and covered it with feminine charm. She opened up to disclose that she did a lot of drugs and studied jazz saxophone at UVM. She revealed more than she probably intended to when she complained about a slight her brother committed against her while on their family boat in Florida for winter break. She paid for the meal.
Bec suggested we go back to her place to play some music as we walked out of the restaurant. I said sure to justify the trouble of driving up there, but really to hear how a poor rich queer girl played jazz. She offered me some Adderall once we were in her room. I asked for water, instead. Her room glowed a warm pink-orange when she turned on her paper lamps. I sat on her bed and watched as she snorted blue dust in the opposite corner. A wave of nausea washed over me. I had never witness someone do this and felt the definition of a square, deflowered in this way. She wiped her nose with the back of her hand and crawled on her hands and knees towards her record player on the floor, next to a few stacks of books.
“Do you like the Velvet Underground?”
“Yeah, especially the stuff they did with Nico.”
“Yeah, she’s ok,” she said, pulling a record out of its sleeve and putting it on to play. Vaguely familiar music that reminded me of similarly lit undergraduate settings provided a backdrop to Bec’s musings.
“Have you ever done heroin?”
“No,” I said, “never had the opportunity.” My effort to come off as cool sounded more like a provincial response to having ever studied abroad or eaten escargot. She kept her eyes on the record, never looking at me.
“They say Velvet Underground wrote this album, well, specifically, this song here, to sound exactly what it feels like to be on heroin.” I took in the swell of the guitar and minimal drum taps and translated them into an unknown physical sensation.
“What’s it like?”
“What is what like?”
“Heroin. What does it feel like?”
“Warm, soft, peaceful. Like this song.” I remembered why I came here and nodded at the black case leaning against the wall.
“Is that your axe?”
“Axe? We don’t call them axes.”
“Just sax?” I giggled but she shot me an annoyed look. She lowered the volume of the record after she took her saxophone out of its case. Her body looked bird frail next to the metal. She ran up and down scales, shot out a few melodies, her phrasing familiar but forlorn, like a sigh. Her fingers stretched over the mechanics of her instrument.
“You’re really talented,” I said after she stopped. She gave a perfunctory “thanks” while she flipped the record and turned the music back up. She got off the floor and went to her closet.
“So, are we going to do this?” she asked, fumbling in the darkness.
“If you want to.” Offer and acceptance. She pulled out a strap-on, already set up.
We went through the motions of wanting, the steps unmemorable from us clothed to naked in her bed.
“What happened here?” I asked of a large bandage wrapped around the arm that rested above her head on the pillow. She looked over at it like it was a forgotten souvenir resting on her vanity.
“Oh, that,” she said, “I tried killing myself the other day.” The dance stopped. I sat up slow as not to appear startled, still straddling her. The weight of the room, and the sadness it contained, permeated. It now circulated within me, heavy and disorientating.
“I can’t do this,” I said and started to get off her.
“Yeah, my therapist did tell me I shouldn’t date for a while,” her voice distant and resigned. She took off the strap. We got dressed together. It wasn’t until I was out of the city that I realize she didn’t offer to pay me, not like I gave her much of a reason or chance to do so. I called my friend Olli from DC on the dark drive home.
“Is she ok?” They asked.
“I don’t know. I think so?”
“So, you just left after they revealed that to you?”
“What was I supposed to do?”
“Yeah,” they reflected, “I guess that’s kinda a lot for a casual hook up.”
“What if I told you I was supposed to get paid for it?” I waited for their response to my confession. My eyes started to tear in the silence, blurring my vision in the night. I looked at my phone. The call dropped. I was on that stretch of 89 where I couldn’t reach anyone.
When I got home, I took out a pair of scissors from my desk drawer and snipped off my rat tail. In my hands, it felt like a feather. I set it on a textbook and climbed into bed. In the morning, I returned to where I had left it. My parents kept a lock of my hair from my first haircut. At least once, growing up, while we were unpacking from one of our moves, my father came across it and held it up to my hair. “You haven’t changed at all,” he said. I tied an end of the lock with a rubber band and placed it in a desk drawer.
I couldn’t get up for my 10am corporations class that following Monday. The lack of motivation came on stronger than usual. I had not done the reading, so busy I was on Sunday avoiding everything I needed to do, on top of questioning my choices. As derelict as I was with my studies, I continued to mull over my current predicament like a seasoned professional, walking through every worst-case scenario of how my foray into escorting could ruin me.
I kept checking my phone, hoping for a response to my texts from Olli. I groaned when I saw Ali appear on the screen with an agonizingly neutral “Hey, what happened Saturday night?” I rolled over in bed and googled, “how to fake your own death.” Another text came in as I scrolled through the “faked death” Wikipedia page.
“Good morning beautiful! Miss you! I can’t stop thinking about you in my car the other night” followed by a kissy face emoji chaser. Had I given Deb my number?
“Ali is being weird so I just thought I would reach out to you. Who needs her, right?” For the first time in what could have been days, or a lifetime, I heard the sound of birds outside. Great question, Deb. I threw the covers off me and gathered my books for class.