My New Friend by Jessica Wadleigh

Editor Acacia Blackwell, Editor's Choice, November 26th, 2018

The anxiety that I felt over my gender identity was always latent, ready to present itself at a moment’s notice.


Personal Essay by Jessica Wadleigh

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A side-effect of living as a closeted trans woman and feeling like you need to police your every action is that you create a voice inside of yourself that does just that. The anxiety that I felt over my gender identity was always latent, ready to present itself at a moment’s notice.

I started smoking pot every day after my brother Drew died.

Being stoned didn’t really help with the pain. I wanted it to, and when my college housemates commented that I was smoking a lot, I used grief as an excuse, but it wasn’t the truth. Not all of it, anyway.

This jailor voice lived inside me, and was ready to remind me everyday at every opportunity that I was scum. My jailor told me that I was a faggot and a loser and a weirdo. Getting stoned finally shut that voice up, at least until the buzz wore off.

In my early teenage years, I used to steal clothes, a pair of panties here, a bra there, from women I babysat for. Slipping into a thong was pretty much the only way I could get off, even if it left me feeling terrible about myself when I finished. Once I stopped babysitting, my supply of new clothes dried up. Getting a car when I turned seventeen finally gave me the chance to go shopping for some girl’s clothes of my own.

It took me weeks to psych myself up for my first buy. I finally slid through Walmart’s sliding doors with the intention of leaving with something really special, something of my own, about half an hour before closing time.

The women’s clothes were in the middle of the store, and I went back and forth between the food and electronics sections that flanked it, scoping out the section as nonchalantly as possible. I filled my cart with sour gummy worms, a PC gaming magazine, a twelve pack of Coke, a Tommy Boy DVD and, eventually, a pink camisole and thong lingerie set that was easy to swipe on my roll-by.

I picked this Walmart for my first buy because they had self-checkout stands, not knowing that they closed earlier than the rest of the store. Only two full-service checkstands were open, and both had lines.

I decided to join one of the lines, pulling my cart behind a man in a black polo, but when another guest came up behind me, I clumsily excused myself out of the queue, feigning that I forgot something. I threw my arms up in frustration, hoping the gesticulation would tell them that I was a normal, forgetful person, and not a pervert trying to discretely buy something frilly and lacy to jerk off in.

I thought about ditching my cart, fleeing, but I was so close. I paced through the food aisles, watching for when the coast was clear. A few minutes later, the lines died. Now all that stood between me and the orgasm I’d been fighting against for the last three days were the cashiers.

I chose the younger of the two and went for it.

I was sweating and red and not doing a great job answering how my night was going when the bored blonde behind the register perfunctorily asked. I threw the magazine and candy and movie and soda and lingerie and that important applesauce I had almost forgotten onto the trolley as if these were perfectly normal things to be buying together. I was too distracted to answer her, too fearful that the newcomer pushing his cart into the line behind me would notice what she was folding into my smiling plastic bag.

I swiped my ATM card, immediately worrying that my name would print on the receipt, and that the blonde clerk would take the receipt and show the older clerk what I’d bought, and the older clerk would recognize my last name and then go to my aunt, who worked in the Walmart photo lab and ask her: “Hey, do you know this fucking homo?” And then my aunt would tell my uncle, who as Dad’s brother should really be the one to break the news to him:  “Surprise, your kid’s a freak!”

The credit card terminal beeped with acceptance. The clerk’s extended arm held out my prize, which I accepted with clammy palms and no eye contact. She robotically thanked me and my voice caught in my throat as I mumbled back a thanks. I turned and glanced at the person behind me before walking away. His hands were in his pockets and he was bent over the conveyor belt looking closely at a magazine cover, oblivious to me. I reached into the bag for the receipt and after making sure my name wasn’t on it, crumpled and threw it in the trash on the way out.

I was practically undressing from the moment I shifted my car into park.

I snuck in through the back porch of Dad’s house, then down the staircase in the garage to the basement door, until I finally made it into my room. I pulled the nightie out and dropped the bag to the floor in one motion, the case of soda landing on the bed with a small bounce. My teeth clicked as they broke the tag fastener’s thin plastic.

Price tag removed, it was finally time to put on the negligee, more salmon than pink on closer inspection. I stepped into the thong, bent down to pull it up. I walked over to the full-length mirror mounted onto one of my closet doors and my stomach dropped.

My new get-up was both too short and too wide. Thick black chest and stomach hair spilled out under lace fringe. The thong was too big and kept slipping down down my slender hips. I walked to my bed, trying to make the best of it, the thong falling to my ankles on the way.

I tried and I tried, but I couldn’t get my reflection out of my head. I couldn’t get off. I pulled the set off me and threw it under my bed in frustration. I had waited for this moment for weeks, and all I wanted to do now was scream. My hands went to my eyes and I felt like I was trying to press my tears back into them, but I couldn’t stop them.

I don’t know if I was more upset because none of it fit or because I wanted it to.

I got better at buys, but the experience still sucked. I was a regular on crossdressing forums and I learned to follow the advice of other posters. I rotated between local stores, avoiding becoming too regular at any one.

The early morning hours, right around nine or ten, were the easiest times to shop because the stores were light on customers and whatever staff was around was usually busy doing inventory or cleaning up from the day before. When I did have to face a cashier, I learned that I should always ask for gift receipts, and to explain to clerks who may ask that this was, obviously, for my girlfriend.


Once I started to smoke pot every day, the idea of shopping and getting something cute and new became more exciting than scary. Before pot, during the few times I allowed myself to think about my gender identity, the only aspect I could ever focus on were all the negatives. I worried that my parents would find out and send me to a camp for conversion, that the government would find out and my political science degree would be useless, that someone would see me dressed like this and beat me to death. Smoking helped me find a headspace where I didn’t have to listen to that, where I could think about what I actually liked about it, what it meant for me to like it, and how I could accommodate those desires.

I didn’t have any of the answers yet, but these were new questions to ask. I still wasn’t ready to admit at twenty-one that I was transgender, preferring to define myself to myself as a crossdresser. Being a crossdresser defined what I was going through as a pastime, something avoidable and under my control, not something that was as unavoidable and intrinsic as being trans would be. Being able to think about what I was living in new ways felt like a path forward.

Back at college, away from my parents and stoned for all my waking hours, it didn’t take as long to build up the nerve to go to the JC Penney in the strip mall on the east side of town for a buy. I sat in my car in their too big, empty parking lot, mid-afternoon on a weekday, smoking a bowl, hyping myself up to go in and walk straight toward what I wanted, instead of browsing the men’s section first.

I told the clerk in the junior’s section that I was just browsing when they asked if I needed any help, and for the first time ever, I actually browsed. I took my time. I brushed my fingers over fabrics. I looked things over, turning them down because I didn’t like the color of the thread or the way the collar sat. It was love at first sight when I picked up a flowy black sleeveless top made with soft, stretchy fabric. After a quick glance over each shoulder, I held it against my body, making sure it was the right length.

I didn’t ask for a gift receipt when I checked out.

The house I shared with my two roommates was empty when I got back. I decided to take my time—a top like this deserved celebration. I packed my bong, drew a bath and began the tedious process of shaving my legs. The water grew cold and I nicked my legs in more than a few spots, but the sight of my smooth legs when I finished was forbidden and thrilling.

The cool air soothed my legs as my bong and I walked up the stairs from the bathroom to my bedroom. I pulled out a black demi cup bra from the suitcase I stashed toward the back of my closet. The bra fit tightly around my rib cage, holding the socks that I stuffed with in place. The boyshorts I paired with it were hot pink and stretchy, stolen from someone drying their clothes in our campus’ shared laundry facilities. I hiked up a denim mini skirt that was definitely too short and then finally pulled the top—my top—over my head. It fit me well, and I loved the way the flowy fabric swayed when I shimmied.

I unplugged my digital camera from the charging stand by the computer and started snapping pictures. I took a trial shot, making sure that my face wouldn’t appear in any of them, set the self-timer, and then positioned myself in a variety of poses, hands on my hips, wide-leg stances showing off my fresh-shaved legs, shots where I wiggled, trying to time the movement of the fabric with the camera’s five-second timer.

I often posted pictures of my outfits on the crossdressing forums I visited. Other users would comment, offering advice on more feminine poses or to compliment the outfit. I couldn’t wait to share my new top and my smooth legs. I jammed my memory card into my computer and started uploading the good pictures into a group thread.

I had a particular admirer that I was hoping would respond to my new outfit. One user, Doug, was always complimentary whenever I posted a new picture. He used flattering words like “beautiful” and “breathtaking” and didn’t tell me how much cum he’d spilled while looking at them.

Doug asked me to keep it secret when he sent me a picture of himself. He was older, fishing from a rowboat. He had a rod in hand and one of those khaki bucket hats to keep his presumably bald head from burning. Whoever took the picture was probably the last person he ever wanted to know where he was sharing it and with who.

I was never attracted to Doug or any of the other men who messaged me, but it was intoxicating to feel attractive to anyone. I decided to take some special pics, just for him. I laid down on the bed and took shots that showed off my legs, his favorite part of me. I sat on the edge of the bed and crossed my legs, perching the camera on the computer chair to provide the best vantage point. I left the camera in the same spot and spread my legs for an upskirt. I hesitated to click the small silver SEND bubble in the private message to him, but when I did and finally orgasmed, my body shook and shuddered like never before.

I wanted him to like how I looked. I wanted anyone to.

The intensity of my orgasm overpowered my high. In just a single second, everything flipped. The excitement disappeared, maybe as a consequence of a high dose of testosterone or whatever hormone hitting my brain on the moment of release. My stomach flipped. I wanted to barf at the thought of having sent Doug those pictures.

I looked down at my body. The trashy skirt hiked up to my stomach. My fake tits were lumpy, a bit of sock poking out. My legs were red and blotchy, itching and burning, especially through my inner thighs. I’d stopped shaving at my groin and there was a strange demarcation between my clear cut legs and the forest of chest hair that extended dick to neck. A few shots of ejaculate had geysered onto the rayon, in no time caking permanently into the now forever-marred fabric.

I looked disgusting.

I was disgusting.

I folded my arms over my face, blocking any light.

I didn’t cry, just wondered.

Who did this kind of fucked up shit?

Why had I wasted a whole afternoon for this?

Why couldn’t I stop doing this?

I grabbed my bong and took a few hits before cleaning myself up.


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Header photograph courtesy of Devin N. Morris. To view his Photographer Feature, go here.

Jessica Wadleigh is a creative non-fiction author. Born in upstate New York, Jessica moved to Portland eight years ago. She is the author of several zines, including Sunshine and Grape Crush, as well as the host of the reading series Tell Me A Story. Catch her on Instagram @jesswadleigh.


Acacia Blackwell

Acacia is a writer from Portland, OR, which suits her because sunshine gives her anxiety. She is currently completing an MFA, despite being recently told by Tom Spanbauer that to become a better writer, she needs to "unlearn all that grad school stuff." She listened, and it seems to be working. Acacia is working on a collection of personal essays that she really doesn't want to admit might be a memoir, and a memoir that she really doesn't want to admit might be a novel.