My Summer of Discontent
With the fog of the passage of time, one memory stands out in glaring Technicolor and Panavision! It was late August 1968, during my “Summer of Discontent”. It was also the Democratic National Convention. And why does this memory stand out with such blinding clarity?
Like so many I started out crossdressing in my early teens by trying on my mother’s bras and girdles. I remember the erotic feeling my pubescent body experienced putting these garments on. When I was fifteen my parents and sisters were out for a long weekend, so I went for it! I put on underwear including nylons, stuffing the bra with extra nylons. I found a late 50’s era ball gown my mother had stored way back in her closet, a low-cut bright Kelly green with a built-in petticoat. I put it on, then sat down to the mirror to try my hand at makeup. I used a powder base, then some blush. I applied some eye shadow, then a generous amount of mascara, followed by a bright red lipstick. Then the pièce de ré·sis·tance- a Marilyn Monroe style wig my mom had. When I put it on and looked into the mirror (albeit the makeup was far from perfect), I saw a rather cute girl looking back at me. I was hooked!
I continued dressing whenever I could during my teenage years, but the pressure of school, social life and chores kept me from practicing my passion except occasionally. Then I met Rodney. Rodney and I went to the same college in Chicago and shared many classes together. Being a nerd like me we shared the same interests. What was really important is Rodney had an apartment in a Brownstone on Waveland and Kenmore, directly across from Wrigley Field. Today these buildings are known as the “Rooftops”. Back then they were just an open roof where we go and watch the Cubs while listening to the play-by-play from Jack Brickhouse (pre-Harry Caray) on WGN. Rodney and I became good friends.
One Saturday afternoon, following a substantial amount of illegal beer (we were both 19), Rodney pulled out a photo of a very pretty girl and asked me if I knew who it was. My response was, “Your girlfriend- your sister”? To my surprise he said, “No, that’s me!” It almost knocked my socks off, and the floodgates opened! Before the day was out Rodney (who called herself Barbara) had made me up, given me one of her dresses to wear and topped it off with a ‘Ronnie Spector’ wig. I became Paula! And I must admit, thanks in large part to Barbara’s makeup skills, and a lot of padding in the right places, I looked (and more importantly felt) like a very pretty young girl.
Thus began a weekly tradition of getting ‘dolled up’ and sitting around the apartment drinking cheap wine. Then one Saturday we decided to ‘go for it’ and venture out. We hopped on the ‘El’ and went down to the Loop. We wore white blouses, mid-knee skirts and flats. We looked like a couple of secretaries downtown enjoying the day. I recall shopping at Marshal Fields. We capped the day off at White Castle, where a couple of guys hit on us. As we got bolder we ended up on Rush Street on Saturday nights taking in the dance clubs. Sure, we were underage, but Illinois driver’s licenses back then did not have photos, and all the bouncers cared about was that you were pretty. Pretty girls got in free as an enticement for the guys to come and pay a cover charge. For a farm boy from rural Illinois, who had become a city girl, it was wonderful!
Now bear in mind this was the late 1960’s. I do not think the words “crossdresser”, “transsexual”, “transgender”, or “non-binary” even existed then or if they did they were certainly not in my lexicon. The most common names for girls like us were “transvestite” or “female impersonator”. In the late 60’s a male dressing as a female, even in Chicago, was illegal. We didn’t care we were having too much fun. Chicago in the late 1960’s was a relatively safe place as long as you knew what parts of town to stay away from. Also, while the “Summer of Love” had just taken place the previous year, guys were still fairly prudish and girls rarely ‘put out’ unless they were ‘trashy’. That’s why the dance clubs were so much fun.
My “Summer of Discontent” began at the end of the spring semester in 1968. Prior to the introduction of the ‘lottery’ in late 1969, the draft system was comprised of a multitude of ‘eligibility’ categories. The most coveted was the 2-S Student Deferment. If you were engaged in a “field of study” at a recognized educational institution you were deferred from the draft until your studies were completed. That meant those with the financial means could stay out of the draft by being in school. By the summer of 1968 I was a fourth-year undeclared junior, who’s only goal was to stay out of Vietnam. But then for some reason, and I do not know why to this day, I decided to drop out of school and not return in the fall. Within a week I was 1-A “Eligible for the draft”.
Knowing my fate, my summer was spent in a boozy stupor. Sure, I would go to work in the morning, but my afternoons and evenings were spent drinking cheap wine and even cheaper beer. Then came August and the 1968 Democratic National Convention. For those of you who have not heard the story of the 1968 Democratic Convention I must tell you it was a tumultuous occasion that has been described by some historians as a “Police Riot”. I didn’t know about that at the time. What I did know was Barbara and I were having a great time listening to music and joining in the melee whenever the opportunity presented itself. On the evening of August 28th Barbara and I were on Michigan Avenue not too far from the Conrad Hilton hotel. It was a fairly warm night. I was wearing a white blouse, mini skirt, and wedgies. I had replaced my dark brown ‘beehive’ wig for a blonde shoulder length ‘flip-up’ with a headband. Both Barbara and I were pretty far gone, or to put it more accurately we were ‘drunk as skunks’!
Suddenly, the crowd which had been milling about shouting slogans began yelling and throwing things at the police. Then things suddenly went from bad to worse! I vividly remember the Chicago police on that night. This was before the days of riot gear. They were wearing blue hardhats and carrying nightsticks. It was a sea of blue! They weighed into the crowd like a herd of charging buffalo. It was pure mayhem! I was knocked down, then dragged by a policeman. In the process he grabbed my hair and pulled off my wig. Then all hell broke loose! Realizing I was a guy, he proceeded to give me a working over with his nightstick that I can still remember. He kept calling me ‘faggot’ and pounding! He would probably still be pounding on me if a surge in the crowd had not come along pushing him away from me.
All I remember afterward is somehow Barbara got me away from the crowd. She had even retrieved my wig! I vaguely recall her leading me back to the subway to catch the train back up to Addison and her apartment. I was dazed, confused, and traumatized over what had happened to me. I was severely beaten just because I was wearing woman’s clothes! I was also the wiser in that I realized being a crossdresser was not all ‘fun and games’ and there were some serious implications in doing so.
Five months later I was in uniform and a year later I volunteered to go the very place I spent so much time trying to stay away from. Then came more college, marriage, family, a successful career, and my days as Paula were left far behind me. But I think it was that traumatic experience on that August night in 1968 that not only kept me away from crossdressing for almost fifty years, but also made me into the quasi-homophobic person I described in an earlier article here at CDH.
Today I am fully enjoying being Paulette. No trauma, no guilt, just having a good time exploring my feminine side. However, I am reminded it was not always so easy and accepting being a crossdresser. I guess that is why I get so upset when someone says we crossdressers are not truly members of the ‘trans’ community. My membership was paid on August 28, 1968 with bruises and broken ribs, so I think I have paid my dues in full!
Thank you so very much for taking the time to read my article. Now please feel free to leave a comment in response to my article and to answer one or more of the questions I’ve posed to you below:
- When you were in your late teens or early twenties did you ever attend a dance or other large ’straight’ social gathering as a girl?
- If you did, did you find some guys were attracted to you, and if so, how did that make you feel?
- When you have been out in public as a girl have you ever feared for your safety?
Again ladies, thank you and I look forward to your responses!