How I Lost the Miss Congeniality Contest, Part I

“My God! Has it been twenty years already?” I exclaimed as my friend Rachel reminded me of the years we attended several of JoAnn Roberts Paradise in the Poconos events.

“It’s been twenty years and more. Those were the days, my friend.”
In the 1980s and 1990s JoAnn promoted and hosted twice yearly gatherings for the TG community. They were held in the Pocono region of Pennsylvania. I understand she used different venues over the years. Many participants came to the events twice a year, every year. I only managed to attend three of the events, all around 1990.

All the ones I attended were at a relatively small resort called The Pines. Rachel and I had met at one of these events.

It is great that JoAnn continues the Paradise tradition now every November in Rehoboth Beach, DE. The name has changed to Beauty At The Beach but the style and events remain the same after all these years. I enjoyed my time at the Beach but my heart remains at the Pines in the Poconos.

Rachel’s reminder has inspired me to write about what was for me a personally memorable Paradise weekend at the Pines.

Run by Hildy, an Austrian American and her family, the Pines seemed to be the perfect spot for some 100 crossdressers, transvestites, their friends and admirers to gather in relative security and anonymity.

The ‘weekends’ pretty well followed a standard format, starting on Thursday evening and finishing on Sunday morning, rooms, single or double and all meals were included in the price as were admission to all of the ‘Paradise’ events.

The events included a theme party on Thursday evening, seminars and a tag sale on Friday, dinner and a cocktail party dubbed the Princess Promenade on Friday evening where everyone would be introduced.  Saturday most of the attendees would spend the day practicing or priming for the evening entertainment called the Phantasie Phollies complete with crowning of the Princess of the Poconos and her court of Miss Ingénue (newcomer), Miss Congeniality and Miss Sophistication. The weekend would wind down with a farewell breakfast on Sunday morning.

I’d had enough fun at my first event that I decided to return at my next opportunity. I’d had enough fun but in retrospect I’d been a bit too shy and withdrawn. I had only met and got to know a few of the weekend participants, had not joined in many of the activities and sat quietly through any of the discussions I attended. In retrospect I realized I hadn’t taken advantage of the opportunity to learn from others what it meant to be a crossdresser in those changing and increasingly liberal times.

A year and a half later when it came time to make my return I determined that I would be more open with others: I would seek opportunities to meet and get to know everyone I could.

I wanted to involve myself in every activity and become known in a pleasant way to all the other attendees.  I set myself the goal of being as open and pleasant a person as I could be, of meeting as many of the ladies as I could. It wasn’t my main objective but I thought if I do that other participants might even consider voting for me to be Miss Congeniality.

As I wanted to take in the whole experience I had to arrange for Thursday and Friday off work, leaving home Thursday morning to drive the six hours to the Poconos. I also wanted to take in the whole experience en femme. That meant finding a place en route to ‘transform.’

The trip started out well. The line of vehicles to go through customs was very short and the border guards easily bought my explanation of going to a golf weekend in the Binghamton area. A little over two hours later I was in the Binghamton area but not to play golf. I was ready to become Linda. The transformation was achieved by going to a truck stop, renting shower facilities, going in as ‘Doug’ and coming out as Linda. No eyebrows seemed to be raised perhaps because I was careful to dress more like a trucker queen in jeans and a tee shirt than as a drag queen.

There then remained a little more than an hour’s drive to the Pines, some of it over narrow winding back roads. All was going well when I saw a group of four people walking on the road ahead of me. I started to slow down. I didn’t see the deer which chose that time to bound across the road and in to the front of my car. That is I didn’t see her until she rolled up my car hood and laid her flank across my windshield. The last I saw of the deer was of her sliding off the car, righting herself and bounding on what seemed like three legs in to the woods. I slammed on the brakes and stopped the car. The four people in front had started back to see if everything was alright. “Oh no,” I thought. “I’m going to be discovered.” However when the deer moved off so did the four. I learned later that deer collisions are pretty common in that neck of the woods. They don’t raise a lot of interest.

Finally making it to the Pines I found JoAnn, got my room key and was told I had about 15 minutes to get dinner.

The deer incident gave me an instant conversation starter with my table mates. Being ‘from away’ they were much more interested in the collision than would have been the locals. Some were concerned about my car and others about the fact that I might have been ‘outed.’ Around the room I was soon known as the ‘girl who hit the deer.’

After dinner there was a short break while the girls got ready for the opening cocktail reception and costume party. We assembled in the Pines bar area, some wearing our favourite little black dresses others in costumes according to the theme of the year.

Last time I’d been one of several nurses following the theme ‘women in uniform.’ This year I had what was sure to be a unique costume.

Costume Party

A standard of a Paradise weekend was the themed party on Thursday evening. Attendees were encouraged to dress according to an announced theme. I can’t remember what the theme was that year but it must have fit at least partially with my outfit.

I decided to present myself as a ‘professional beauty pageant contestant.’ I wore one of my best black cocktail dresses, low cut so it showed my cleavage and a black bra, only it wasn’t a bra; it was a form fitting bathing suit. Over the dress I would wear a sash highlighting my current title.  When it came my turn to be introduced Donna, the event DJ, read a series of questions I’d slipped to her and I gave some prepared responses. It went something like this:

Donna: So who have we here?

Linda: I’m Linda and I’m a professional beauty pageant contestant.

Donna: I’ve never heard of that before. What do you do?

Linda: I enter beauty contests with the aim of becoming the face of companies and associations in advertising campaigns?

Donna: You mean like Miss Pabst Blue Ribbon and Miss Budweiser?

Linda: Well that last one’s a boat but you get the idea.

Donna: What titles have you won?

Linda: Well, one year I was queen of the Military Contractors Association. They called me Miss Appropriation. The next year I was named to speak for a tax preparation firm. They called me Miss Calculation.

Donna: I see you’re wearing a title right now. What is that for?

Linda: I’m to speak for the National Transsexual Association to promote the correction of mistakes made at birth. I’m called Miss Conception.

I had a few others but I was getting little reaction from the audience so I whispered to Donna to ask the last question. She complied.

Donna: So if you are a beauty contestant shouldn’t you have a swim suit contest?

Linda: I thought you’d never ask.

With that I stepped out to the middle of the floor and started to twirl. As I twirled I slipped the dress off my shoulders and let it fall to the floor, revealing my form fitting bathing suit, filled out with my expensive silicon breast forms from Lee Brewster’s and low cut to show the effect of JoAnn’s chest taping lesson on creating cleavage.

I finished to what I thought were just polite applause. The dialogue and my strip tease got a few titters but not the laughter I’d been looking for. I figured I’d bombed. However at the end of the event I was awarded second prize for the evening, an assortment of bracelets and other baubles donated by one of the event sponsors.  I also received a few quiet compliments from new friends.

The evening was a chance to meet and touch base with returning friends like TGForum’s own Dina Amberle and make new ones like Rachel and Diane. I learned Diane from DC was the reigning Miss Ingénue. She confided in me that she hoped to be this weekend’s princess. She was gorgeous and outgoing; she seemed a good choice to me. When she learned I was Canadian she told me about her teen years spent living in Montreal. That was my home town and it turns out I knew of one of her relatives who was a bit of a personality in that city.

As the evening wore on I shared some conversation with almost all of the attendees. We were a fascinating bunch, representing pretty well every type of occupation from trades people to professionals such as doctors and lawyers. Quite a few of us were involved in education as teachers, professors or administrators. I am the inquisitive type, always interested in learning more so I was more than willing to listen to others’ stories of their lives, their wives and how they managed (or not) to fit their femme identity in with the rest of their world.

Someone, I think it was Hildy’s son Billy, pointed out the new pine wood floor they had just installed a little over a year ago. “It’s beautiful,” I said.

“But look at it closely,” he replied, “especially around the bar.” It was then that I noticed the many dimples in the floor. It looked a bit like a giant beige golf ball, only flat.

“What happened there?”

He replied, “You girls did. Some of the heavier ones in their spiked high heels left indents in the wooden floor.”

“Shouldn’t we be told not to wear heels then?”

“Nah, not to worry. It’s too late to do anything about it now and it gives us a nice reminder of these weekends. No one else ever comments about it.”

It’s funny how quickly new friends could become good friends at Poconos weekends. In my case Rachel and I just seemed to click. We were about the same age – not that anyone really tells their correct age when they are en femme – and both inquisitive types who had an interest in dressing from a very early age and now a desire to be the best we could be. We both wanted to protect ourselves and our families from the ignominy of having our femme identities revealed yet we both now wanted to be the best we could be. We spent a long time late in to the evening comparing notes. I thought ‘I like Rachel but if that girl doesn’t vote for me for Miss Congeniality I’ll strangle her.”

Then it was off to bed. I by-passed the bar where I could hear some late-nighters discussing transgender politics.

It was tough getting up for breakfast but I managed. When I arrived in the dining room I found Rachel saving a place for me. I sat beside her and she gave my thigh a squeeze then left me alone. One of the other guests, a university professor, was talking about the Civil War. In my younger days the Civil War had been a great interest of mine. I had lots of question for the professor which she seemed to appreciate. Chalk up another possible vote or two.

Friday morning Rachel and I went over to the Liz Claiborne outlet to see if they had the perfect outfits for us. It was the first time out in public for Rachel. However we didn’t find any irresistible items so it was back to the Pines for lunch and to get ready for the tag sale.

Tag Sale

A standard feature of the Paradise weekends was the Friday afternoon tag sales. Attendees with items to sell would put them on display in the hope that other attendees would pluck down at least a few dollars for a few items.

For this year I went a bit overboard. I brought a hockey equipment bag full of clothes and other items that I figured might sell. Needless to say, despite my bargain basement prices I achieved few sales, perhaps $50 worth.  I did manage to part with one additional item, a dress that I thought would look good on one of the girls who seemed to be a little hard pressed for cash and who apparently was attending the event at the reduced rate that JoAnn offered to certain deserving girls. She accepted the dress but I was disappointed that she would not wear the dress for the ‘Follies’ on Saturday night. I thought she would look stunning in it. I’m sure she eventually did.

To be continued.

In the next article I will explain how my hopes rose that I might be named Miss Congeniality only to hear someone else’s name called.

Category: Transgender Fun & Entertainment