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.

Crossdresser Superstore

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”.

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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

 

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Kim Dahlenbergen
Active Member
1 month ago

Oh my god, I have lived such a sheltered life! I recall watching Mayor Daley’s police riot as a 15 year old. Later I participated in a few anti-war rallies, even spoke at one…rather inarticulately and no one got the joke. But from my preschool age through much of my adult life I lived in desperate fear of being seen for what and who I was (and am). So short answer is 1) no, at that age I hid everything about myself, 2) I have been propositioned by guys, but it was not my thing, and 3) since around 2010… Read more »

Kim Dahlenbergen
Active Member
1 month ago

Hi Paulette, well, three months after that campus rally I was in basic training… totally stateside. And yes, it has taken me all those decades to accept myself. Truth be told, I still struggle with self acceptance and still live two distinctly different lives. I am trying to shift the balance away from the center, to the point where most of my life is lived as a woman. I am pretty reserved by nature, so but for a few early forays to gay/drag clubs in Houston, most of my real life experience has been in everyday places doing everyday things.… Read more »

Lea
Active Member
1 month ago

Paula, your story is so touching and the writing is so good! I felt like I was there, following as your shadow, experiencing a side of crossdressing so different.

I admire how you had a friend, and how you both went out as pretty girls. The beating sounded scary, if not one of those moments of life flashing before you. Then the rest of life after.

I’m happy for you that finally you get to enjoy the freedom of being you. Thanks for sharing, your story is inspiring.

Sherry Kirk
1 month ago

As I’ve slowly been transitioning over the past 5 or so years, I’ve come to the conclusion that I’m not going to care what others think of myself. I’m happier now than when I was forced by marriage to stifle my desires. Now I’m full time Sherry. I have found most people are accepting and peaceful with me. Even my church has welcomed me for who I’ve become. I’m out to just about everyone I know. I dress in a feminine “male” attire at work, but wear my breast forms with my shirts. I’m happy now and at peace with… Read more »

Sherry Kirk
1 month ago

Thanks for the reply. I’m really enjoying my life and have found the inner peace I have today. It’s so much easier than hiding from myself and the world.

Kathryn Lynn Peters
Active Member
1 month ago

Just WOW, Paulette! Thanks for writing such an excellent story, totally enjoyed it! I’m just a couple of years younger than you but I remember the riots in Chicago! I was a sophomore in college that summer (Rutgers – Newark NJ) and was 2-S. I started crossdressing about age 5 when I discovered lipstick! And trying on mom’s underwear, shoes and dresses when I was alone (not much opportunities back then!). But like you, college and later being drafted before the lottery had me running to the USAF recruiter who signed me up for 4 years. Not a lot of… Read more »

Kathryn Lynn Peters
Active Member
1 month ago

Hey Paulette, just a forgotten item re: the draft…I was overseas in Libya when my lottery number came up…341! Can you believe it? Had I hid for another six months before enlisting, I’d have never gone in. But, I don’t regret it at all, gave me a chance to travel throughout Europe and led to my eventual career, a dentist. So, all good.
Hugs,
Kathryn
PS: Sure, let’s keep in touch!

Kathryn Lynn Peters
Active Member
1 month ago

Lolol

Trish White
Baroness
Active Member
1 month ago

Wow, Paulette what a great well written article, I loved it. Don’t get me wrong but after reading it I was glad I was a Canuck. We never had stuff like that happen when I was a young crossdresser. Of course we still had to be very careful where we went and with whom. Just like the States, back then, homophobia reigned supreme in the Great White North as well. I might add that you look absolutely gorgeous in the pic. Keep the articles coming, they’re very good and if you’re not a writer….you should have been.

Love,
Trish

Darlene Congdon
1 month ago

Paulette, great article. I can understand why you are a part-time girl now. I am so sorry you had to face the negative side of being a transgenderd woman. I am glad to see that the pleasant aspects of of womanhood did not stop you from being the beautiful woman you are.

Elle Jonson
1 month ago

Kim, what a heartbreaking story. I am so glad, however, that you overcame that horrible trauma and have reclaimed Paulette. I didn’t dress publicly until late in life. Although I’m not interested in men (though I do find stylish transfemmes incredibly sexy), I have been “hit on” by guys and do love the attention. Like any girl, I am much more concerned about my personal safety than I am when I am in guy mode.

Marie Chandler
Baroness
Trusted Member
1 month ago

Oh my gosh! This is an incredible, personal story. I felt like I was there with you. Thank you for sharing and for being a pioneer for us all. How wonderful that you met a kindred spirit at such a young age. I haven’t read through all the comments, so forgive me if you’ve answered this, but are you and Barbara still in contact?

Marie Chandler
Baroness
Trusted Member
1 month ago

I totally understand. It happens. About 20 years ago, when I was going out dressed on a simi-regular basis, I met a crossdresser with a similar viewpoint on dressing as myself and she happened to live in my neighborhood. We would get dressed at each others homes before heading to the club. I burned out on it after a while and lost interest. I only returned to dressing and going out again in the last few years. We lost touch and I have no contact info for her, but I wonder where she ended up.

Sapphire Steele
1 month ago

OMG, I can’t believe that happened to you. I’m glad you made it through ok, and didn’t let that define your life.

To answer your questions, I’ve never been out of the house dolled up. It’s so hard to find anything that would fit me, and I know I’m not passable. I’m hoping being here will help change that

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