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:

  1. 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?
  2. If you did, did you find some guys were attracted to you, and if so, how did that make you feel?
  3. 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!

Sincerely, Paulette

En Femme Style

 

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Brooke Stevens
Member
3 months ago

Paulette. Thank you so much for your article. I am just now learning to put into context what I have known for 45 years. I’m bisexual and genderfluid. I am neither male more fully female although I do lean towards the female more and more as the years go by. I am married to a wonderful woman who knows I am bisexual but swings from forbidding me to explore to “go ahead, just don’t tell me about it.” It has been a difficult journey and now at age 55, I am entertaining something I thought I never would. Coming out… Read more »

Kerri Smith' class='avatar avatar-64 photo' height='64' width='64' />
Kerri Smith
3 months ago

Paulette,

Thanks for the wonderful article you posted. I have been out in public dressed as a woman and feared for my safety when a guy started giving me second looks,
Kerri

JackieBoy
Baroness
Noble Member
3 months ago

Wow, wow, wow what a great article. I too am a native illinoisan, but from the far north, safe suburbs of Mundelein. I remember changing my license when I was 17. Back then a license was just a 4-5 layer piece of paper with no photos and definitely not covered in plastic. Since my birth year on the license was 56 all I did was go to my SS# and with a straight edged razor blade and cut out a :4″ there and replace the “6”. Voila Jackie is now 19 the legal drinking age when I was a freshman… Read more »

JackieBoy
Baroness
Noble Member
3 months ago

I am a Huskie. NIU BABY

JackieBoy
Baroness
Noble Member
3 months ago

Not for anyone from Illinois

Kristen Smithly
Active Member
3 months ago

I was a young lass (lad?) in ’68, my oldest sibling was 17, turned 18 that fall. I was aware of the riots in Chicago, we watched them. Both my mom and dad were visibly shaken and upset at was the police were doing.(We lived in a small town in the rural west and this stuff “just didn’t happen in America”), naïveté working it’s magic. When I was older and married, my wife went on a week long business trip and the kids were at grandparents 350 miles away. So I was dressed all week when not at work. Two… Read more »

Jillian(Jill) Evers
Member
3 months ago

What an Amazing Story Paulette, You were so Lucky to have those experiences and at the same time so unlucky to have some of those experiences.. We Are Lucky to have you here!! I never did the dances or even went out dressed But I had Very Long Hair in the late 60’s & 70’s which led to Bullying in and out of school , along with the wrath of “certain” family members.. I can’t even imagine if I had tried dressing then in public! As I look back (Thank You) I’m sure those experiences helped keep me an ultra… Read more »

Peggy Sue Williams
Duchess
Noble Member
3 months ago

Thanks for the memories of “the draft” a.k.a. The Selective Service System. It sure interrupted my cross dressing activities back in the 1960s. When I mention “the draft” around people today, they look at me with blank faces. Imagine compulsory military service in America today?

Gwyneth
Active Member
3 months ago

Great article Paula. I remember those Vietnam days. Watching the draft lottery on TV. Wondering how my birthdate would land when it came my time. I turned 18 in 1975. Vietnam was over, but we weren’t sure. I remember the 68 DNC riots. Looks like you were living the dream before that.

I also remember a lot of bad things in my life. Would I change it? Some of it for sure. But it might change where I am now. So….

Love,
Gwyn

ps.. you are pretty!

Gwyneth
Active Member
3 months ago

I remember hearing horror stories from some happenings in some pretty redneck bars. Why a transgurl would seek out companionship in those places boggles my mind. Maybe a deathwish. Back then, I’m not sure how I would have reacted if I was making out in a bar and got a crotch surprise.

Angela Booth
Active Member
3 months ago

That is quite some tale Paulette. I am slightly younger than you and live in the U.K. but do vaguely recall the late 60’s and news reports from the states with various riots with police going in with batons. It all seemed very ugly and quite a time of turmoil. I was preteens and finding my way around my sisters clothes and dressed secretly. At that age I did fear reparation if I was caught dressing and knew that it was ‘not right’ by others but I felt differently of course! I did have opportunities to dress for fun and… Read more »

Teri Linnealis
Member
3 months ago

I consider Paulette a good friend and have heard this story before. Those of you that are younger and freely crossdress in public now might not know the real dangers that were the 1960’s to the 1980’s. Across the board, blacks, whites or any group that was nonconforming stood a good chance of being singled out as the enemy. WE as a society have made huge strides in if not understanding at least in not giving a shit what others do. But the haters are still out there. Be diligent in your adventures, avoid the areas where miss information breeds,… Read more »

Suzanne Martin
Member
Member
3 months ago

Paulette – I remember the days of the draft and the lottery. I attended college as well and had the student deferment. I also remember the DNC riots. Those were tumultuous times in our country. As others have said they were times when if you were different you could expect to be treated poorly. My crossdressing stopped during my high school years out of fear of being caught. I did have an experience in college where I attended a Halloween party dressed as a woman and had the help of my girlfriend getting ready. I remember being nervous and it… Read more »

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