First off, this posting violates the prime directive of this blog, established back in December 2005. So be it. Rules are intended to be bent, or broken. I will try not to make a habit of it.
Second, I confess to no particular skill at writing, story-telling, or humor. The fact is, that any story wherein the protaganist is speaking of hirself in one gender, from the perspective of living in a different gender, is going to be pretty rich territory in the categories of pathos, humor, irony, sympathy, etc. Like shooting fish in a barrel, to be honest. It's somewhat critical to the story to know that at the time, I was living as a fairly geeky young male.
So here, (more or less as told, with some additional colorations and vibrant details) is my story:
When I was in high school, I worked at McDonald's. I started out cleaning the lot & lobby (where I toiled for over a year, I was a slow learner or perhaps just patient when it came to getting shit jobs dumped on me). It was the lowest caste of fast-food employment. Over time, I worked my way into the kitchen, to the front register, eventually to crew manager (sort of half way between underpaid hourly workers and underpaid management). But the summer between high school and college, I worked the overnight shift, cleaning the restaurant after close and getting it ready for the next day. (This was back in the 70's, before fast food joints stayed open all night)
It was a two person shift - a maintenance person who cleaned the lobby, seating areas, bathrooms, and the exterior (an 8 hour job that one could finish up in 4 if one cut corners), and a close-open person who cleaned the kitchen area and got ready for the breakfast shift (my job). My co-worker that summer was a guy named Paul McNally, who was a few years older, and a business major. Paul often smoked a bit of weed in the evening before his shift, and would insist I go get my guitar, which often lived in my car, I being a wanna-be rock and roller, and also imagining opportunities to connect with young women by dint of my sensitive musical side. Paul's favorite song was that Kink's classic - Lola. He'd stonedly slur my last name "Roussel, play that L-O-L-A lola song....." Of course, being a wanna-be woman (on top of wanna be musician), Lola was dangerous ground. (Exactly what did he know, or had he guessed, about me?) But I played it.
Paul's foible was marijuana. Mine was sneaking out of the restaurant at 3:00 am, driving to a nearby goodwill trailer that always had bags of clothes piled outside, and going shopping for women's clothes. I'd grab a bag or two, and later that morning, after my shift ended, go through the clothes looking for something that fit and was worth keeping. Then I would either take the remainder back to the Goodwill trailer, or dump them somewhere. I am, for the record, not proud of this - but at that time I was too freaked out at the notion of actually going shopping for myself. The whole scared young transperson in the pre-internet, pre-daytime talk show era, when information came mostly from the library card-catalog or encyclopedia yearbook updates, led me to some less than admirable behaviors over the years.
One summer morning, after my shift, I drove my car (a 1973 periwinkle blue AMC Hornet hatchback, recently inherited from my father) over to a quiet industrial park to go through my stash. And for whatever reason, that day I decided to dump the remainder in the woods. As I finished that task, up rolls a Framingham MA police cruiser. I was bagged.
The officer approached, wondering what I was doing. I made up some story about my mom giving me a bag of clothes to take to goodwill but deciding to dump it in the woods. He told me to recollect the clothes while he called my house for confirmation.
Fortunately, this was the late 70's, before voice mail, call waiting, etc. My sister (bless her social vivaciousness) was on the phone, and so the officer could not get through. So.....we waited, me in my car, looking nervously in the rear view window at the officer trying to get through to my mom.
Finally, I decided to fess up, to be honest. I stepped out of my car, and walked back to the cruiser, and as the officer cracked the window, I croaked "I need to tell you the truth". So I told him. I was a cross-dresser, I had grabbed the clothes from the goodwill box, but I was disgusted with myself so I was dumping them (ok, maybe a little lie, now that I recall it further). I suspect there were some tears involved (this being the first time in my young life I had actually admitted this to another person). He sent me back to my car.
A few minutes later, he called me back. He had a friend (perhaps he himself?) who faced "that same struggle". Get some help, you can overcome this. Take the clothes back to the goodwill box, never do this again. Understand? I most certainly did.....
I often think back to that day. How my life would have been different had the officer gotten through to my mom. Or if he had decided to arrest me. (I got arrested later that summer, for sign stealing, a story best left for another time). Or any of a dozen other permutations or outcomes.