What happens when a bit of fun collides with happenstance?

Happenstance

Saturday, January 3, 1987

“Where is Claire?” Julie fidgeted, absently speaking aloud to her friends.

“Well, she’s only a little late,“ Megan pointed out.

“Yeah, she’ll be here,” Jenny reassured.

We sat in Julie’s front yard, waiting for Claire, the girls dressed for a night out. Claire was the last one to show up. The gate was open in anticipation of her arrival. I had been invited to visit for a while before they went to their favorite restaurant for a girls’ night on the town, their first of the new year. As a boy, while I did understand the girls’ need for the bonds of sisterhood, I couldn’t help but feel left out and it stung.

While we talked, my nerve around Julie reasserted itself, as it had for the past year. Suddenly, Claire shot into the yard not dressed for the restaurant.

“Guys! I can’t come out tonight.” She fretted. “My grandmother had a heart attack and we’re on the way to the hospital. We got the call while I was getting ready and I didn’t have time to call you so I just had to stop by instead. I’m sorry, ladies, but I have to go!”

“That’s okay. Take care of yourself! We love you!” Julie insisted. We took turns giving her hugs and she was off.

With that, we went inside and climbed the stairs to Julie’s room. When we got there, Julie asked what everyone wanted to do. They had some time before they left for dinner... and before I went home. For the first few minutes, we chatted while we looked at clothing catalogs, occasionally cooing over a dress. We often bonded over something along those lines, whether it was a teen magazine, catalog, or celebrity gossip rag, but it didn’t matter to me. I enjoyed being as close to them as a boy could get.

At one point, Julie pointed at a dress in a catalog that had a black velvet bodice and dark royal blue, satin puff sleeves and skirt. Bursting out giggling, she joked, “Hey, Dylan! That dress would look cute on you with black pantyhose!” The other girls laughed and even I had to chuckle, albeit with my face burning... until Julie took it up a notch by making a troubling suggestion.

“You know what? Let’s dress you up for real! That’ll pass the time, won’t it?!” That won another round of laughter, and the other girls’ faces lit up with goofy smiles, but Julie wasn’t done. She continued, stepping over to her closet, as though I had already agreed, “I’ll bet you whatever you want that with your shoulder-length hair, you’re going to look like you were born a girl. In fact, you’re going to look just like Amy!”

Amy was another friend in their group who attended their get-togethers about half the time, as her schedule permitted, but not that night. We had almost the same shade of strawberry blonde hair and similar blue eyes.

Looking around the room, I saw enthusiasm without a trace of disgust. It felt safe enough and I shared their boredom. Anyway, I was curious about girls’ clothes, not that I had ever mentioned that to anyone but Julie. In fact, I had made a New Year’s Resolution just over a year earlier to explore my feminine side, but that had never panned out. I had confided it to Julie because she was my best friend and my crush. Yet, it was for that reason that my failure to carry out my resolution undermined my self-confidence around her to a greater extent each time I saw her as the year slipped by.

Oh, what the hell. I did make that resolution, didn’t I? Maybe it’s time to face it.

“Okay, you can dress me up,” I agreed.

Boy, did I underestimate what they had in mind!

Before long, I was wearing a dark royal blue, velvet, sheath dress that hung just above my knees. Beneath that, I wore a bra and panty set made of nylon in a nude shade. On my feet were black, faux suede pumps with a one inch (2.5 cm) heel. The girls had even coaxed me into a pair of pantyhose in a hue between light toast and white.

Before I could wrap my head around it all, they ran my hair through a curler before pulling the top half back and fixing it in place with a barrette. Julie joked, “You know, this is a lot easier on someone who takes care of her hair! Anyway, now that you’re dressed as a girl, you really do look a lot like Amy! Holy crap!”

“Oh my god, she really does!” Megan enthused, astonished.

Stealing a glance in the mirror, I realized they were right! “Holy crap! I do! That’s scary!”

We must have been getting noisy. Jenny jumped up to crack the door and make sure we weren’t attracting attention. “All clear!” She smiled, coming up to gaze at me in astonishment.

“Say, I have an idea! Just for fun, let’s see just how much we can make you look like Amy with the right makeup!” With that, in the midst of the laughter, Julie added mascara followed by Amy’s trademark cat-eye liner and her usual light coat of taupe shadow, followed by lip gloss in the shade that Amy favored. As she worked, Megan handed her the makeup, item by item. Julie had skills! She then adorned me with a silver heart-shaped pendant that matched the sweetheart neckline of the dress, along with matching heart-shaped, dangly, magnetic earrings that looked like pierced ones. My feminine appearance felt like a strange mix of foreignness and delight and it made me as nervous as I had been all night.

The rosy pink nail polish they put on my nails, another favorite of Amy’s, had just dried when Julie stood me before her full-length mirror and squealed, “I knew it; you do look like a born girl! Look at you!”

As Jenny glanced out the door again before nodding in satisfaction, I stared at my reflection, from the pumps on my feet and the nylons on my legs back up to the makeup on my face. Julie was right and, while nervous, I was aware of a secret thrill at the sight of myself and at the feeling of it all. I was right in the depth of my reverie when Julie’s mother caught us off guard. “Girls!” her voice wafted in from the stairs with urgency.

I barely had time to do anything but turn my back to the door and pretend to study the first thing I could grab, which was a Rubik’s Cube that I found on Julie’s nearby dresser. Her mother burst through the doorway in a tizzy.

“Girls, quick! I lost track of time talking to my friend on the phone,” she spoke a mile a minute. “The restaurant is too busy to hold our reservation, so we have to leave right now to make it! Come on!” Then she noticed me. “Oh, hi, Amy! You joining us tonight? Sorry about the panic. It’s my own fault! Come on! Let’s go!” she laughed, as she headed out the door and down the stairs without waiting for an answer.

All of the girls looked at me, stunned, with zero time to change me back. Thankfully, Julie had dropped my clothes on her closet floor, where they were out of sight with the door closed, so that we could see the full-length mirror on the outside of it. With my appearance now a convincing imitation of Amy, Julie’s mother didn’t have a clue that she was looking at a boy en femme.

Julie finally found words. “Dylan, I am so sorry, but you’re going to have to be Amy tonight. I-is that okay? I swear to God this was not what I had in mind, but... I-I don’t think there’s any other way.” Julie apologized, accepting a jacket and purse for me that Megan handed to her after dropping into it the tube of lip gloss they had used.

“Don’t worry about it. Let’s just get through this.” I blurted.

Handing me the feminine items, Julie noted, “Well... maybe this is a way of finally carrying out that New Year’s Resolution that you made last year.” She shrugged in apologetic fashion.

“Come on, girls! Get a move on! We’re going to lose our reservation!” her mother’s voice sounded from downstairs.

“You’re right, Julie. About all of it. There’s no time and I need to do this, I guess.” I whispered back, as I donned the proffered white bolero jacket and shouldered the small, black purse.

“I am so sorry about this!” Julie smiled. Then she grabbed my hand, and led me downstairs.

* * * * *

Thirty minutes later, after the strangest car ride of my life, we parked in the Masonic Temple Parking Garage. Exiting onto the sidewalk, we turned right, and stood at the corner, waiting for a green light. Meanwhile, I marveled at how different it felt to be standing on a downtown corner, dolled up for a girls’ night out, complete with makeup, nail polish, and pantyhose. It was scary, but in a good way, like an exhilarating roller coaster! As the light turned and we crossed the street, I glanced at Grace Cathedral, ahead and to my left, where my family and I had attended the Christmas service just nine days earlier. My coat and tie had been uncomfortable, as always.

Huh. In this dress and these nylons, I would have fit right in with all of the other girls. Well, I guess I would have worn a red or green dress instead of royal blue.

I sighed with nostalgia. Turning right to wait for the next light, we faced Huntington park, its trees lit by colorful Christmas lights. They reminded me of the tree lighting ceremony that I had attended a month before Christmas. I had been relaxed then, enjoying the ceremony but awkward with myself. Now, I was apprehensive, but enjoying myself. The contrast between those two moments was profound. Focusing on my present circumstances, my thoughts went in a different direction.

Hmmm. I wish I could get rid of my nerves. What if I experiment with seeing myself as a girl for the evening, instead of seeing myself as a boy in a dress? Maybe I’ll feel normal and I can rela--

“You okay?” Julie checked while her mother was occupied by Megan and Jenny.

“Yeah. I was just noticing and thinking.” I smiled and nodded to reassure her. “Normally, I’m relaxed with the circumstances but nervous about myself. Now, I’m nervous about the circumstances but I’m relaxed with myself. It’s such a switch!”

“Wow. Then you’re already learning about yourself! That’s great!” she returned my smile.

“Yeah,” I nodded.

And I’m noticing that I’m not nervous around you anymore!

* * * * *

The light changed and we completed the short walk to The Tonga Room, a Polynesian restaurant at the Fairmont Hotel. My predicament began to feel even more real as we walked into the establishment packed with diners. I was worried about maintaining my cover, but I was glad to eat there. I loved the food.

The room was once an indoor swimming pool with a good amount of deck space. The pool was still there, but it was surrounded by a railing and now featured a floating stage that could be moved to one end of the pool for access and back to the center for performance. The restaurant was rich in Polynesian decor, with thatched roofs over the bar and several tables. The eatery was even capable of a simulated tropical storm that put on a five-minute show every thirty minutes. It was rigged to pump water from the pool into overhead pipes from which it downpoured back into the pool. During the first couple of minutes of each storm, it was just the rain. Then thunder and lightning effects would kick in for the remainder. It was always fun! Only this time, I was dressed as a girl and grateful in the extreme that the show included no wind to mess up my hair!

Our table was a short distance from the dance floor next to the bar. My seat turned out to afford the dancers a clear view of me, along with Julie, who sat at that end of the table. Julie’s mother occupied the other end of the table, at a ninety-degree angle to me.

“So, Amy, what’s new with you?” She chatted.

During the ride in the car, the girls had given me information to rattle off when questioned, so I knew what to say.

“Not that much, actually. We’re still settling into the new home, but I’ve almost got my new room set up.” I smiled, doing my best to imitate Amy’s voice and speech patterns.

“That’s great,” she congratulated.

Julie then jumped right into the discussion, perhaps to give me an excuse to turn my face away from her mother. “So, do you have more space now? Your old room was a closet!” That, I realized, was a clue.

“Yeah. My queen bed fits better now!” I ad-libbed, deciding that was a safe assumption. Anyway, the real Amy could always explain that she had measured improperly or had meant to say “full bed” or whatever size her bed really was.

“Amy, did you have your sister’s birthday dinner last night?” came Julie’s mother’s next inquiry, indicating that she was suddenly puzzled.

Julie fielded that one. “Yeah, Mom. They had a great time!” she lied.

“Yeah. What she said!” I blurted. All I had to do was smile and nod before I turned back to Julie.

That was how it went throughout the meal. I spoke only to Julie or Jenny, who was seated across from me, unless Julie’s mother spoke to me. Every time she did, the other girls managed to give me a subtle signal to tell me how Amy would answer. Julie would then comment and I would look over at her. It gave Julie’s mother minimal opportunity to look me over and, having no other expectation, she thought I was Amy the whole time. When that wasn’t going on, the other girls would take turns chatting with her.

I enjoyed hearing the wait staff address me as Miss. As I spent time with my girl friends, I realized that enjoying their friendship and their company was different as a girl in delightful ways. Before long, I needed the restroom. As girls do, I asked Julie to come with me.

As we rose to head in that direction, I realized a few things.

If I’d been here as a boy, I would have had to go alone. I would have felt cut off from the rest of the group... and now I can see that I’ve always felt that way. But as a girl, I have a friend with me and I feel like I’m part of the group, even going to the restroom. I feel so much more connected to them! I’ve been missing out on this part of my friends! I like it so much better this way. I don’t know if I want to go back to being a boy.

* * * * *

As I self-checked in the mirror, reapplying my lip gloss unbidden, waiting for Julie, my thoughts wandered again.

I feel like I’ve wasted a year of my life being afraid to keep my New Year’s Resolution to explore my feminine side, especially now that I have some good reasons to believe that the pretty girl in the mirror is who I really am. I’ll have to talk to Julie when we have more time.

Soon, she joined me at the sinks and, making sure we were alone, I spoke to her.

“You know, I think this may be the real me.” I murmured, looking her in the eyes. My face must have shown the weight of that realization.

“Wow. You know, now that you mention it, I think you might be right. I have kind of wondered, you know, even since before you made your New Year’s Resolution last year.” She sighed as she thought for a moment before echoing one of my own thoughts. “It’s like you’ve never been very comfortable with the boundaries that kind of have to be there between boys and girls because they both need them. Do you know what I mean?” She smiled at length.

“Yeah.” I nodded. “I had that same thought myself. Now that those boundaries are pretty much gone, at least for the night, it’s becoming so clear how much they’ve been keeping out.” I sighed.

“Yeah. Well, we’ll talk more, but right now, we’d better get back. I don’t want Mom to wonder what’s taking us so long because we don’t want to draw her attention to you. Come on,” she smiled, offering her hand.

“Yeah, let’s go back,” I took her hand and we left the restroom.

* * * * *

Julie’s mother glanced in our direction with a smile as we resumed our seats at the table, but Megan chatted her up while Julie began a private conversation with me. Just then, the next simulated storm began and Julie took advantage of the noise to lean close.

“By the way, I didn’t get a chance to ask. Are you having a good time?” She inquired.

“Yeah, I am. You know, I should probably tell the others about what we discussed, now that I think I know, I mean. I don’t want to have any secrets from my friends.” I hazarded. With that, the simulation sounded a thunder clap and flashed a strobe.

With a subtle tilt of her head and a suppressed smile, she nodded her understanding, trying not to giggle at the timing.

“Do you think—” I cut myself off to give myself a chance to lean close to Julie. “Do you think they’ll be okay with it?” I ventured, using the simulated rain to cover my voice.

“Yeah, they will. You know us; we don’t hate anyone.” She winked.

Just then Jenny’s eyebrows rose and she glanced at us, noting our secretive discussion, before focusing on me with a quizzical look on her face.

“What are you two talking about?” she queried, thankfully not loud enough to draw the attention of Julie’s mother, but glancing her way to ensure she was occupied with Megan.

“We’ll talk later,” I smiled.

Megan’s eyes had also flickered in our direction, but she was sharp enough to keep her discussion going with Julie’s mother. The simulated storm continued and I breathed a sigh of relief that it had covered my clandestine conversation with Julie. But it wasn't done doing so just yet! It was then that I felt a little girl grab my right arm with a giggle.

“Amy, come back to the table! We’re gonna have cake!” She beamed.

Dear God! Please tell me she’s looking for a different Amy!

I looked into the eyes of the eight-year-old as Julie spoke to her.

“Erm, hi, Emily! Happy Birthday!” Julie bid her.

“Thank you!” She smiled.

“I thought you guys were eating at Carlos and Pancho’s!” Julie investigated.

She shrugged, glancing at Julie. “Well, we were, but they had a fire today and they had to close. Daddy says they burned it down making my birthday cake, but he’s joking!” She giggled. “Anyway, we’re here now!” She smiled, self-satisfied. “I like this place better. Look at the storm!” As if on cue, another burst of thunder sounded, accompanied by fake lightning.

As I looked at Julie for answers, noting the uncomfortable expression that she did her best to hide, she understood my question. “Oh. I should introduce you. Emily is Amy’s little sister.” She introduced with a smile, making Emily look at me with a bewildered expression. Staring at Julie, I felt my eyes widen and I instantly smiled to hide my startled expression.

“Oh, my goodness! Happy Birthday, Emily!” I looked back at Emily.

“Thank you,” she beamed. “Come on, Amy!” She tugged at my arm.

Shit! I’d better think fast!

“Erm, sweetheart? I’m not Amy. My name’s Dylan,” I used my own name, glancing at Julie. That way, if Emily mentioned my name to Amy – which she would, of course – it would trigger no alarms. Since Emily didn’t know that I was a boy, she would notice nothing amiss, either, beyond the resemblance to her sister. Hopefully. She took a close look at me and nodded to herself.

“You’re right! I’m the silly one. Sorry!” She laughed, blushing. “I better go now! I gotta blow out my candles!”

With that, she scampered back to her table, which I couldn’t see, perhaps in the back corner somewhere. The storm ended and I started to calm down with relief. Alas, just as I thought the crisis was over, Jenny stifled a soft gasp and cleared her throat. With her eyes, she gestured behind Julie’s mother, where I spotted Amy approaching from a little ways off. I grabbed Julie to “talk in the restroom” and intercept Amy before she got near our table.

This just might work out after all!

“Hey! Did I see my sister stop by your table?” She laughed, making eye contact with Julie. Then she saw me and did a double-take, her eyes bulging.

“Whoa!!” she blurted.

“Hi, Amy.” I smiled, before explaining our antics at Julie’s house before we rushed to the restaurant. I shrugged, acting natural in hopes that she would follow my lead, which she did.

“Well, I have to admit we look more alike than I thought, especially when you’re stealing my look, you bitch!” she giggled, getting us started. “It’s kind of scary, actually.”

I shrugged in embarrassment.

“Yeah, it is! Anyway, we need to get to the restroom and back to the table before my mother looks this way. Otherwise, Dylan’s cover is blown! We’ll fill you in on the rest of the night later!” Julie coordinated.

She hugged Amy, who then hugged me. “You look terrific!” she smiled.

“Thanks!” I grinned.

With that, we parted ways.

* * * * *

After a quick visit to the restroom to freshen our lip gloss for an appearance of legitimacy to our departure, we returned to the table. Julie’s mother didn’t seem to notice anything.

Gawd! I really hope nothing else happens! I’ve had enough close calls for one night!

Before I knew it, we finished our entrees, passed on desert, paid the bill, and headed for the exit. I breathed a sigh of relief that I had made it through the meal. Julie locked arms with me and whispered, “You okay?”

“Yeah. I’m okay. I’m still... enjoying being a girl, but... phew! Too many close calls already!” I murmured under my breath.

“Yeah. Well, we’re out of here. We’ll be home soon. When we get there... let’s see...” she thought for a moment. “As soon as either Jenny or Megan gets picked up, we’ll stall long enough to change you back and pretend that Amy got a ride home with whoever it is. Either one will work. Anyway, then we’ll sneak you out of the house and you’ll be home free!” she strategized.

“Yeah. That’ll be good,” I shook my head, as if disagreeing with myself. I’ll be a boy again... back to being cut off from my friends by those boy-girl boundaries that will keep it that way.

“We’ll talk at home.” Julie promised.

* * * * *

Thirty minutes later, we gathered in Julie’s room to discuss what had been held back for later discussion. We made ourselves comfortable, except for Jenny, who headed for the door to make sure the coast was clear and close it. Alas, she didn’t get there before Julie’s mother stepped into the room, closed the door behind her, and leaned on it.

Uh oh. What is happening?

“Hello, girls.” She flashed a Cheshire grin. “If I may say so, Dylan, you are so convincing as Amy that it wasn't even you who blew your cover. Emily did when she ran up to grab your arm. The poor kid had no idea what she was doing. Anyway, that was what tipped me off.”

I felt my face blanche. “Erm. Thank you?”

“You’re welcome! Now, I don’t have any problem with you... enjoying femininity as it were, but... may I ask why you’ve graced us with the presence of your feminine alter ego this evening?” She probed.

“Well, we were going to do some talking. So here it is. On New Year’s Eve, not a few days ago but last year, I mean, erm, I made a New Year’s Resolution to explore my feminine side because I have suspected for a while that... I’m a girl.” I began. “But I couldn’t bring myself to do anything about it. The events that took place before we left for dinner tonight... well, they pushed me into it and... I finally carried out my year-old resolution.” I smiled at Julie. “I learned a lot tonight. A lot became clear, including who I really am.”

“Well, it’s certainly been an eventful night for you!” Julie’s mother marveled. “I must admit, you seemed to have a delightful time at the restaurant and, what the hell, I suppose that a girl’s night out is a perfect time to explore your feminine side.” She shrugged with a smile.

“Yeah! And now I see how different it is, how much better it is to be with my friends as a girl! I don’t want it to stop. Ever.” I choked up.

“Well, I don’t know that it has to. It’s time you brought this to your parents, if you haven’t already, and you’ll need to talk to a specialist who can help you sort this out, but you may well be right about who you are.” Julie’s mother smiled.

“Yeah, I think I am. And I will.” I grinned.

“Alright, I’ll leave you girls alone now,” she bobbed her head before she departed the room, closing the door behind her.

“Okay, Dylan. Now it’s my turn to talk. I need to tell you something... well, all of you, I guess.” Julie swallowed.

Oh no. What is she going to tell me?

“Okay. I’m listening. We all are. No pressure or anything.” I tittered, getting her started.

“Okay, okay. Here it is.” She took a breath. “Dylan, that last-minute rush before dinner came out of nowhere. None of us planned that.”

“I know?” my brow furrowed in confusion.

“But you made that New Year’s Resolution to explore your feminine side a little more than a year ago, and like you said, you couldn’t bring yourself to do anything about it. So, I decided to give you a little push by dressing you up tonight. That’s why the shoes look brand new, because they are.”

Seeing my face as I processed, she hastened to continue, “N-now, I didn’t tell the others about your New Year’s Resolution until now because I knew I didn’t have your permission, but I also knew that they’d have fun dressing you up. Like I said, we’re not haters.” She took a breath. “Once you were dressed, I was going to invite you to come out with us as a girl to explore yourself because you really have to live it. You can’t do that here. But I would never just spring it on you or force you into it. Mom really did lose track of the time and, well, we got caught up in turning you into Amy,” she giggled, making us all start.

She took a breath. “Anyway, Dylan, real friends do push you to step out of your comfort zone so that you can grow. Or heal. It’s just that real friends go with you and they take care of you along the way.” she smiled.

“Okay. I will admit that I needed that push, so thank you for that.” I embraced her and she returned the sentiment.

“Hey, Dylan?” she murmured in my ear, still clutching me.

“Yeah?” I responded as she pulled back far enough to look me in the eyes, our arms still holding each another.

“It’s my turn to make a New Year’s Resolution. From now on, I have got to give us a lot more time or just pick another time altogether.” She giggled. “I don’t want to surprise you like that again. I mean, with Amy’s family showing up at the Tonga Room, we took too much risk and we did it without really having your consent to leave the house as a girl. I-I really don’t like that.” Her face turned serious.

“Well, me either, but it couldn’t be helped.” I shrugged, letting it go. “Anyway, don’t worry about it. I did consent to being dressed up and even to being turned into Amy.” Cue the fresh round of giggles. “Besides, I had to do this eventually, so why not tonight, surrounded by my friends?”

“Yeah, you might as well,” Megan smiled.

“Besides, it was fun!” Jenny chimed in.

With that, I knew I was going to continue being myself, with their help.

I really am going to be a whole new person this year!

* * * * * The End * * * * *