My First Time

Originally appeared in Transgender Tapestry #105, Spring 2004.

by Allana Allen

I arrived in Provincetown on Sunday, the first day of Fantasia Fair, and couldn?t even bring myself to walk into the inn where I had reserved my room, even though I was in boy clothes. I was so scared I drove past the inn twice and eventually parked in a public lot so I could walk around the town to go CD spotting before I could decide whether
I had the nerve to try it myself. Either there were no other crossdressers in Provincetown that day, or they were so passable I certainly wouldn?t fit in.

Disheartened, with tears welling in my eyes, I walked back to the car, where I sat for a very long time, trying to decide what to do. I had all but decided to forget this silly fantasy and make the three-hour drive back home when it came to me that the worst-case scenario was that I could simply check into my room and spend a pleasant week in this lovely little tourist town on Cape Cod?as a man. It took me more than two hours before I had enough nerve just to check in.
Locked safely inside my room, I
somehow found the courage to unpack the four suitcases of women?s clothing and lingerie I had brought with me. As I unpacked, hanging each item in the tiny closet or folding it neatly into the two drawers of the small dresser, Allana fought her way to the surface. What would it hurt if I dressed here in my room?
The transformation was somehow
different this time than it had ever been before. For more than forty years I had slapped myself together haphazardly,
and it had always been good enough. Something deep inside me, something I couldn?t reach or even understand, was telling me that this time good enough wasn?t good enough. This time I wasn?t dressing to look like a woman. This time, I was a woman getting dressed.
I tried to let go and let Allana come to the surface as she had never been allowed to before. The inner struggle was one of the hardest things I had ever done, but slowly she fought her way out. In time, I stood before the dresser mirror looking and feeling more like a woman than I ever had before. It took me another hour and a large pair of woman?s sunglasses to hide behind before I found the courage to actually open the door and walk out of my room.

Literally trembling in my panties, I fretfully walked the length of the hallway in my high heels, praying no one would open a door, step into the hall, and see me. My legs trembled as I descended the staircase to the lobby, and my eyes looked neither left nor right as I took the four or five steps from the stairs to the front door. Riddled with apprehension and nervousness, and overwhelmed with absolute fear, Allana pushed us out the door and I stepped into the real world, dressed as a woman, for the very first time in my life.

I headed for Fantasia Fair headquarters at the Crown & Anchor Inn, just a couple of blocks away. It was the longest walk of my life. My heart was pounding so hard I truly thought it would leap right out of my chest.
Commercial Street, the main drag
(no pun intended) in Provincetown, was filled with people. I just knew they could tell I wasn?t a real woman. My stomach was one gigantic knot and my legs trembled with every step as I walked, but I marched on, keeping my eyes on the ground and looking up only to make sure I didn?t stumble in my high heels.
After what seemed an eternity, I finally reached the C&A and quickly headed for the side door. The apprehension of what lay behind that door was nothing compared to the complete and overwhelming fear I was feeling out in the open.

Inside, I found a large meeting room similar to a small theater. A long table had been set along one wall, and three women sat behind it, papers covering every inch of the tabletop. Around the room were men and women(?) filling
out forms.

When you spend your entire life
inside the box, and the only time you ever express your inner self is when you are alone, the opportunity for conversation simply doesn?t happen. As a result, you never really know what the woman within sounds like. I approached the table, never even considering to try to disguise my voice, and actually spoke for the first time ever in my life while dressed as a woman. In my own husky male voice I quavered out a nervous, ?Hi, I?m here for Fantasia Fair.?

I was greeted without so much as a strange glance, and as naturally as if they were talking to a real woman.

?Have you been to FanFair before?? I was asked.

?No? I replied, my masculine voice still quaking. I was handed a packet of papers and asked to fill them out at one of the smaller tables and bring them back.

If it wasn?t for the fact that I was so nervous, this could just as easily have been an everyday transaction at my local bank. There was such a calming sense of normalcy in the air that I could hardly believe what was happening. I filled out the papers and returned them to the same woman. Another woman started handing me more papers and began to explain that this one was a guide to the Fair and included a map of all the places in Provincetown where I would be going?these were lunch tickets for the different restaurants around town where the women would be eating. On and on she went, with me hearing less than ten percent of what she was saying because
I was still so nervous.

The last thing she told me was that there would be a welcoming cocktail party at Crowne Pointe Inn at 5:30 and that she expected to see me there. It was now approximately 3:00.
Somehow, I had managed to make it this far without so much as causing a raised eyebrow. I was still nervous and still scared to death, because now I had to walk Commercial Street again to get back to my inn! I donned my sunglasses once more to hide my true identity, and ventured out into the open for the second time in my life!

The trip back to the inn was no easier than the trip down, and I was wet with perspiration, despite the cold ocean breeze, by the time I reached my inn.
I quickly ascended the staircase to
my room without looking left or right. To this day, I couldn?t tell you if anyone was in the lobby or even standing behind the desk.

I reached my room, slammed the door, and realized I had not breathed since I had left the C&A. BUT I HAD DONE IT! And I was so proud of myself!
I selected a black skirt suit with white stripes and a zippered jacket top to wear to the cocktail party, then spent the next two hours getting ready. When I was done, I checked myself out in the mirror?and went out anyway!

The one-block walk to Crowne Pointe was so short that I didn?t have time to get scared. Besides, I was starting (mind you, only STARTING), to feel a little better. After all, I had managed to stroll outdoors twice already and no one had laughed at me, pointed fingers, or even snickered. I was amazed!
The cocktail party was absolutely fabulous! I had never been to one before, not even as a man. I was greeted at the door by the owners of Crowne Point, who very graciously welcomed me and THANKED me for coming. Nothing in my entire life had ever made me feel so much like a lady. I was directed to a bar where I was handed a cosmopolitan (a delicious pink mixed drink that looked very feminine and was served in a fluted glass). I began to mingle.

Some of the other Fair attendees were already there. Most seemed comfortable in this surrounding. People chatted over here and laughed and joked over there. I quickly noticed to my surprise that most didn?t even try to disguise their voices. Some of the women were very beautiful and some were simply passable, but the vast majority were girls like me who would have a hard time sneaking past a blind man without being discovered.

As I walked toward the rear of the house to what appeared to be the sitting area, I passed through a huge, beautiful, formal dining room with a banquet-sized table at one end and a baby grand piano at the other. The sitting room itself was lavishly appointed with beautiful furniture. I felt like a debutante.
I meekly squeaked out a few polite hellos as I walked past people and found a place to sit. Another woman struck up
a conversation with me as if I were her long lost sister, and I soon started to become comfortable in this surrounding. It felt as if we were just a bunch a women out for an elegant evening.
Across the room, two beautiful genetic women were chatting away and laughing with two of our girls. When one of them walked past me, she paused to tell me my suit was gorgeous, and introduced herself. I nervously thanked her, but when she looked deeply into my eyes, I nearly died. She called her friend over, introduced her as her lesbian partner, then said, ?Doesn?t she have the most beautiful eyes you ever saw?? I could hardly believe my ears. I was being complimented by a real woman!

They began giving me pointers on
eye makeup to enhance my eyes and beauty tips on eye shadow and face makeup. One of them took the zipper
of my jacket and slid it down a bit to expose my (lack of) cleavage, explaining that if I took some makeup and put a little here and there it would give the illusion of cleavage. Then she pointed out that next time I should wear a black bra under the outfit. Perhaps I should have been embarrassed by that, but I wasn?t.
It was my first GIRL TALK, and I loved it. They made me feel so comfortable,
like one of the gals, and we chatted like this was the way it was supposed to be!
Little by little, the rooms filled, until you could barely move, and little by little, more and more of Allana came to the surface. My knees went together automatically as my ankles crossed and slipped under my chair. My hands found themselves folded femininely in my lap, and I began to feel more comfortable in my female persona than I ever had in my life. This was Allana, and she was finally home!

When you?ve hidden inside the box
for more than forty years, as I have, and it has become your entire, comfortable little crossdressing world, it?s hard to even imagine that anything else exists. When your secret life has become so routine that your second self, screaming to come out, amounts to nothing more than another trip to the back of the closet to drag out those dusty suitcases where you keep your life hidden from view like one of Aunt Sophie?s reindeer sweaters, and you double- and triple-check to make sure you?ve put it all away again so nothing is missed that might out you to your family and friends, even the mere idea of a life outside the box seems like a cruel joke.

To allow yourself to think, for even a second, that there might be a place outside that box, outside your secret little world, where you could go and be who you want to be in a real-world setting, surrounded by people who are literally aching to give you all the support, encouragement, and love you could ever dream of, would surely be nothing more than fantasy.

But to suddenly find that it?s not just some joke, it?s not just a fantasy, that it?s real, and does exist, to finally not just peek over the top edge of the box, but come out of the box completely and, for one preciously fleeting week of your life, experience the pure magical wonder of it, to be literally reborn and be able to hold in your hands everything you ever dreamed of and be allowed for the very first time to be a whole person, is such a wonderfully life-altering experience that it?s well worth the personal hell it costs to then have to give it all up and go back into the box!
It took me three years to build up the courage to attend the Fair because I had never, that?s right, NEVER set foot out of the house dressed as a woman before. You want to talk scared? I was petrified!
That first day, Sunday, was the turning point for me. Monday served to further build my confidence. By Tuesday, I was waltzing down Commercial Street and all over Provincetown with my ?head up and tits out,? walking my best female walk and looking people in the eye as I greeted them with a smile and a pleasant hello in a softer version of my own voice. In fact, I was so comfortable by Wednesday that I stopped a local woman on the street to ask directions.

?Excuse me,? I asked, ?but have I passed Napi?s Restaurant??

?No sir, er, ma?am,? she blushingly replied.

I laughed, patted her femininely on the arm, and said ?that?s okay... I?m not sure yet, either.?

We both laughed, and she said, ?In that case, good morning. It?s right down at the next corner.? I thanked her, and as I began to walk away she said, ?I hope you enjoy the week.? I almost cried.

On Saturday night, the last night of the Fair, there was a very elegant final banquet and awards ceremony. One award, Miss Cinderella, is voted on by everyone who attends the Fair. This award goes to the first-timer who best overcame her fears and went on to enjoy her female identity throughout the Fair. By the night of the banquet I was so comfortable in my female identity that I was feeling as if this was the way life was supposed to be for crossdressers. Every-thing was just so natural that I felt like a princess in a fairy tale. I was stunned when I heard I was a runner-up for Miss Cinderella!

No, I didn?t win it, and I didn?t expect to, either. So many other wonderful sisters who were also there for their first Fair had overcome much more difficult obstacles than I. Besides, I wasn?t trying to win an award, I was just enjoying, for the first time in my life, the freedom of being me. Still, I couldn?t believe so many had actually voted for me. I cried like a lady!

EVERYONE in Provincetown was so nice to us and so accepting that it would be almost impossible to be uncomfortable there. I?m convinced that there is nowhere else in the world where I could have come so far in such a short period of time. During the week, I made many new friends and bonded with so many sisters. It was absolutely amazing! Everyone had the same story. Everyone knew where you were coming from. Everyone could identify with you. I met transgendered folks from all over the United States, from Mexico, Colombia, Canada, England, and even from as far away as Scandinavia, and every one of them was my girlfriend instantly! It?s like a wonderful, worldwide, secret sorority, but instead of a secret handshake, we use skirts to identify each other.

Some were passable, others (like me) weren?t. Some were tall, some short, some fat, some thin. Some had wonderful female voices and others sounded like truck drivers. One even had a full male beard! And every single one of them, EVERY ONE! was open, warm, friendly, unassuming, non-judgmental, completely accepting, and ready to offer a huge warm, heart-felt hug at the drop of a hat!
Throughout my lifetime, I have truly felt that I have been in the right place at exactly the right time only three times. The first two times were at the hospitals when my sons were born. The last was my first Fantasia Fair!

It?s hard to describe what it?s like to come out of the box for the very first time in your life, or to explain the overwhelming depth of suppressed emotions that come flooding to the surface in torrential waves when it finally happens. Unless you have experienced it yourself, it?s impossible to convey in written words the wonderful feeling of absolute freedom to actually be the woman who has hidden deep inside the darkest recesses
of your being for your entire life. It is
an unequalled opportunity to explore your inner self, to evaluate your life, to learn who you truly are, and to laugh
and to cry.

The hardest part of Fantasia Fair for all first-timers isn?t taking that first step outdoors?it?s leaving the Fair! They call it the pink fog?that extraordinary sense of self you acquire during the Fair?the feeling of normalcy, wholeness, and oneness, a feeling that everything is now right in the world. It fills us with hopes and dreams and, sadly, the fantasy that we don?t ever have to go back into the box.
For some that is true; Fantasia Fair is
a turning point in their lives from which they never return. They go on to live their lives outside the box, being who they want to be. For others like me, sadly, it is not. Social pressures, work demands, and family relationships are too great to overcome and make it impossible for us to remain outside. The pink fog has special meaning to those of us who must pack our lives, our selves, back into those dusty suitcases and bury them deep into the back of the closet, back into the box once more. We must go on with only the memory of who we really are. We struggle each day to hold on to the identity and the love we found that week in Provincetown, as, day by day, it slips
further and further from our grasp.

We try to return to who we were before the Fair, but that?s impossible.
To paraphrase a few lines from The Velveteen Rabbit: ?Real isn?t how you are made, real is what you become, and once you become real, you can never be unreal again.? So a song on the radio, the faint scent of a certain perfume, the sound of high heels clicking across a room, or the fleeting memory of a special moment at the Fair wells up inside you until you find yourself driving down the road with tears streaming down your face.

Allana Allen at can be reached at: