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Lipstick and Liberation: Caring for Jennifer, a Transgender Woman With MS


Editor's Note

This story has been published with permission from Jennifer.

Sitting on a small patio in a Midwestern suburb, I scooted Jennifer’s wheelchair close, held her hand in my palm and painted her fingernails a hot pink, after scrubbing off the turquoise with nail polish remover — pressing each finger straight at the knuckles. Her eyes were closed as she basked in the warm sunshine.

Jennifer is a transgender, quadriplegic woman who uses she/her/hers pronouns. For 16 years, I was her direct support professional, the technical term for paid caregiver. When I started, I was a 21-year-old struggling single mother of a little girl with cerebral palsy. Jennifer was confident, charming and educated, with gray hair that was combed into a wave that swooped across the top of her high forehead. She wore polo shirts and tortoise shell eyeglasses with multifocal lenses, and looked every bit the high school teacher she had been.

Life was tough for me, raising my daughter without much support, managing all of her doctor and physical therapy appointments and endeavoring to pay my bills. Jennifer coached me on getting my finances in order, dealing with my chaotic housing and putting my daughter’s deadbeat father in the hot seat. She encouraged me to keep alive my dream of graduating college with a GPA that would make me competitive for graduate school. Every time I had a deadline or exam, she cheered, “Give it to ‘em!” as I left her house to go study.

But our conversations weren’t one-sided; she enjoyed regaling me with stories about her college days in the 1960s, which she called, “The best four years of my life.” In her early 40s, she had been diagnosed with multiple sclerosis. The first sign was double vision when she was running on a California beach one morning. Within a few years, she became paralyzed from the neck down and was living in a nursing home.

“I just love being Jennifer,” she said, without opening her eyes. She had been going out more as Jennifer, and I accompanied her. For the Pride Festival, she dressed in a long white shirt tied in front and Daisy Dukes, her bare feet adorned with several anklets and toe rings. Nobody asked any questions, and neither did anyone at her physical or occupational therapy sessions the week before. But when people did, like the suburban moms who suggested to her that she was inappropriate, I stated, matter-of-factly, that she liked wearing these things. That was what Jennifer told me to say and she trusted me to advocate for her. I was her sidekick.

She lived with her mother, a feisty former socialite in her eighties who doted on her. Although they didn’t go out often, because it was just too difficult with getting everything ready, packing up the car and simply being away from home, they were still members of their country club.

Every morning, I transferred Jennifer from her hospital bed in her living room by pulling her up into a standing position and pivoting her toward her wheelchair to sit her down. Jennifer had put on some weight since she was immobile, and I was on the smaller side, but it was a skill I was able to master because we were a team.

Throughout the day, I handled many details for her: hygiene, eating and drinking, scratching itches, moving her body to her liking, helping her pee, covering and uncovering her with blankets, wiping her nose and changing the television channel. I was in a constant state of motion as I assisted her with everything she would have done for herself, but now couldn’t.

At doctor appointments, I was not only transportation and muscle to get her in and out of the car, but someone educated in medicine who could translate the lingo for her and help her make informed decisions.

We were used to the looks, the rudeness and the pity that came with being a disabled person in this country. To cope with all the hostility, we went out anyway (planning ahead for the logistics) and didn’t care if anyone had a problem with it.

Despite the intimacy of our relationship, there was a lot I didn’t know about Jennifer, and gradually, she revealed details about her life that she had not disclosed to anyone. It started with her telling me stories about a time she lived in Las Vegas in the 1970s — escapades of a stripper who performed for an audience as a femme. Her eyes lit up as she recalled her fishnet stockings, eyeliner and high heels, and how the crowd would cheer when she worked the pole at Al’s Cabaret, dancing to her favorite song, “Love’s Theme.”

“Do you think I’m strange?” she asked me.

“Of course not,” I validated. “It’s normal.”

I had grown up in a religious sect with a lot of rules: no makeup, piercings, dancing, movies, television, popular music or friends outside of the church. Of course, no homosexuality — much less being transgender or queer. But since leaving when I was 18 and moving out on my own, I had begun to embrace not only myself, but others the church had told me to avoid. I had partied at gay clubs and shaved my head and rejected any notion that God existed or that I should follow what any man told me to do with my life or body.

With my reassurances that she wasn’t a creep, Jennifer let me further and further into her old life.

“I had real boobs in Las Vegas because of estrogen pills and shots and testosterone blockers. I loved it,” Jennifer said. She described how she got into stripping: starting with nude modeling for an art class at a community college near home and strip-o-grams when she got to Las Vegas after taking a leave of absence from teaching. A transgender dancer at Al’s Cabaret inspired her to see a doctor and begin to transition.

But when the 14 months of leave were over, she stopped taking estrogen and testosterone blockers and returned to teaching. After a couple weeks, her breasts had deflated, but underneath where they had been, white lines remained. She wasn’t ready to disclose who she really was, not while her mother was alive, admiring her “perfect son.”

As she told me stories while reminiscing on her secret life, she shared her desire to to be out as Jennifer, if there was a way.

Since her hands were too swollen from MS to wear rings on her fingers, she compensated with other over-the-top jewelry. I showed her the best sites for online shopping to buy flashy clip-on earrings and smoky eye makeup and helped her complete transactions. She asked me to store her purchases in a safe. I took pictures of her hair as it got longer and what it looked like in the back when I put it in a ponytail. I held her hands up for her to see how her fingernails were growing out.

“You sexy lady,” I complimented her.

“You can call me a queen,” she whispered hoarsely, winking.

Then one day, as we surfed the Internet, she asked me to look for nudist resorts. Being warm helped her muscles relax. We found one that advertised all the amenities Jennifer liked from her former life: spa, restaurants (even though she was on tube feedings now), nightclub, and a tropical poolside setting. Jennifer offered to pay me a travel rate per day and cover my expenses. For about a month, I considered whether it would be feasible for me to go with parenting and other obligations. I had my B.A. degree now and was building my career in public policy, but still needed my “day job.” My daughter was thriving academically and taking violin lessons. I resolved to make the trip work because it would make Jennifer happy.

Once we got there, it was surprisingly liberating. People were walking around nude like it was normal and laughing with each other and playing volleyball in the pool. Some were at the bar, sitting bare-butt on towels and sipping cocktails like they were in their own living rooms. Jennifer’s face was ecstatic, like she had found her new Vegas. After getting checked in and putting our luggage in our room, her first request was to strip her down. I had seen her naked every day. But I kept my clothes on. Even after getting many piercings, having multiple sex partners and generally telling society where to go, keeping covered up was a remnant of my strict upbringing I held onto.

Within the first few days, I painted Jennifer’s nails and let her wear my lipstick. Although reticent, I finally — self-consciously — sat by the pool with her in a bikini she had helped me pick out online. We developed a routine: mornings sunbathing by the pool and chatting with newfound friends, afternoons napping, and evenings watching karaoke or a live band in the pool bar or mingling in the nightclub where guests (who were about her age) flaunted kinky outfits and danced to hip hop and retro music. Wherever we were, I parked Jennifer in a strategic location, so she could participate in the action as much as she wanted to.

When we got back, she told her mother that she had won a trivia contest and the prize was a mani-pedi. She had offered it to me, but I told her she should do it. Jennifer’s mother didn’t question the story, nor did she protest when Jennifer began to regularly have her nails painted.

The trip to the resort became an annual event, and with each visit, Jennifer gradually emerged — from pretty manicures and lipstick to eye shadow and lingerie, and finally, a blonde curly wig and silicone breast forms placed under a bra. My daughter graduated from high school. I became more comfortable in my own skin. Each time Jennifer returns, she brings more of herself back home. And we sit on her patio in the northern sun, painting our nails and showing off our beautiful bodies — to ourselves.

This story originally appeared on A String of Paper Suns.

Getty image by Puhhha.