The Lucky Winner

Another exhausting day had come to an end.

The entire staff had gathered for the now-familiar afternoon meeting, tired but in surprisingly good spirits. Working with children could be overwhelming, unpredictable, and louder than anything Samuel had previously considered reasonable. Yet it also brought a deep sense of satisfaction. The people at Willow House seemed genuinely happy to be there, even at the end of the most difficult days.

As part of the preparations for the annual gala, Marianne announced something several members of the staff had apparently been waiting for: who would participate in the parade, and how the roles would be assigned.

“This year, four adult volunteers will represent the princesses,” she explained.

The organization had spent years building enthusiasm around the parade. Everyone knew the costumes and presentation would be of the highest quality, and both the guests and benefactors had come to expect it as one of the gala’s highlights.

There was also an additional incentive. Each of the four selected volunteers would receive a complimentary facial, a basket of beauty products, and a fifty-dollar gift card donated by one of the organization’s sponsors to spend on makeup.

Amazing, Samuel thought. Exactly what I wanted.

He relaxed when Marianne explained that, as always, participation was completely voluntary. Anyone interested could place her name in the raffle drum during the short coffee break, and four names would be selected afterward.

The announcement immediately filled the room with conversation. Some volunteers wanted the prizes. Others were excited to make the children happy. A few genuinely dreamed of being princesses for a day, while others simply wanted the story they would be able to tell afterward.

None of those reasons applied to Samantha.

She had no intention of participating.

During the break, approximately twelve volunteers placed their names in the drum. Samantha remained near the refreshment table with Jenna, drinking coffee and listening as her friend debated whether the facial alone was worth the risk of having dozens of children step on the hem of her dress.

When everyone returned to the multipurpose room, Marianne stood beside the drum.

“The first four names I draw will be our princesses for the day.”

She reached inside and unfolded the first paper.

“Claire Dawson.”

The room broke into applause as Claire covered her mouth in delighted surprise. Several volunteers around her cheered while she stood and gave an exaggerated royal wave.

Marianne selected the second name.

“Monica Hayes.”

More applause followed. Monica laughed and accepted several enthusiastic congratulations from the people seated around her.

“And our third princess will be…”

Marianne opened the next slip.

“Jenna Collins.”

Jenna gasped.

“Yes!”

She grabbed Samantha’s arm and shook it excitedly.

“I’m going to be a princess.”

“You are.”

“With a facial.”

“And a gift basket.”

“And fifty dollars’ worth of makeup.”

“You’ve achieved everything you ever wanted.”

Jenna laughed and hugged her.

Samuel congratulated her sincerely. He knew how much she loved princesses, and seeing her so excited made him genuinely happy.

The person he had wanted to win had already been selected. Feeling safe, he stopped paying attention while Marianne reached into the drum one final time.

“And our last princess…”

She unfolded the paper.

“Samantha Brooks.”

The name struck Samuel like a bucket of ice water.

“This can’t be happening,” he whispered.

Jenna turned toward him with both hands pressed against her mouth.

“Oh my God. We’re doing it together.”

The people sitting nearby immediately began congratulating Samantha. Someone behind her said she would look perfect. Another volunteer leaned over to tell her how lucky she was.

Samuel forced himself to smile.

“Thank you.”

He accepted the congratulations one after another, doing his best to hide the discomfort twisting in his stomach.

How is this possible? I didn’t even put my name in.

When the meeting ended, Marianne asked the four selected volunteers to remain behind. The rental company needed their information immediately so the dresses could be reserved and adjusted in time for the gala.

Each princess received a form requesting her height, dress size, shoe size, and bra size.

Samuel stared at the final category longer than necessary.

Writing down the numbers felt uncomfortably personal. They were not Samuel’s sizes. They belonged to Samantha—to the body he constructed beneath her clothes and presented to the world.

He filled in the form anyway.

While they worked, Marianne explained what the role would involve. The four princesses would open and close the parade, greet guests during portions of the gala, take photographs with the children, and accompany them throughout the procession.

Samantha looked up from the form.

“How long do I have to be a princess?”

Jenna glanced at her.

“That is an extremely un-princess-like question.”

The other volunteers laughed.

Samantha gave them another carefully practiced smile.

 

The following morning, before the children separated into their regular activity groups, one of the group leaders gathered everyone together.

She announced that four adult princesses had been selected for the gala and read their names aloud.

Maya stood beside Samantha, as she had begun doing more frequently during the past few days. When she heard Samantha’s name, she looked up at her.

“How do you do it?”

Samantha frowned.

“Do what?”

“Want to be a princess without being scared.”

Samantha studied her expression.

“But you’ll be an amazing princess too.”

The children would be part of the parade as well, each dressed as either a prince or a princess. Their costumes had already been ordered, and the four adult princesses would accompany them throughout the procession.

Maya lowered her head.

“I’m not doing it.”

“You don’t like princesses?”

“I love them.”

“Then why don’t you want to be one?”

Maya stared down at her shoes.

“Because I’m not pretty enough to be a princess.”

The answer came so quietly that Samantha almost missed it.

She crouched beside her.

“You’re the prettiest little girl I’ve ever met.”

Maya smiled shyly, but she did not look convinced.

Samantha sat beside her on one of the low benches.

“I’m scared too.”

Maya looked at her.

“But you’re pretty.”

“That doesn’t mean I’m not scared.”

“But at least you’re going to be one.”

Samantha hesitated, then leaned closer as though sharing a secret.

“I didn’t want to be a princess.”

Maya’s eyes widened.

“You didn’t?”

“No. But I thought maybe doing it would make me stronger, because I’d be facing one of my biggest fears.”

“What fear?”

“Making a complete fool of myself.”

Maya frowned.

“How?”

“Well, imagine me tripping over the enormous skirt in front of everyone.”

Samantha lifted both arms and acted out a dramatic fall.

Maya burst into laughter.

“Or maybe my crown will fall off and roll across the floor,” Samantha continued. “Then I’ll have to chase it while everyone watches.”

“That would be funny.”

“Not for me.”

Maya continued laughing, and Samantha smiled with her.

When the laughter faded, Samantha’s voice softened.

“You don’t have to be a princess if you don’t want to.”

Maya looked down again.

“But if you decide to do it, I’ll be there. I’ll stay with the most beautiful little princess in the whole parade.”

Maya looked at her carefully.

“You promise?”

“I promise.”

“We’ll be princesses together?”

Samantha took her hand.

“We’ll be princesses together. I promise with all my heart.”

For the first time, Maya looked excited rather than frightened.

 

When Samantha arrived home that afternoon, she decided not to become Samuel immediately.

The transformation back had become tedious, and Lily was supposed to be attending a dinner that evening. He would have the house to himself, so there was no reason to rush through removing the makeup, uniform, and wig.

Besides, he reluctantly admitted, the volunteer uniform was not that bad.

The skirt kept him cool.

Samantha settled onto the couch and turned on the television while reheating a container of boneless wings left over from several nights earlier.

She had just carried the plate into the living room when the front door opened.

Samuel could not remember ever moving so quickly.

He abandoned the food and ran upstairs.

“I’m home!” Lily called. “Where are you?”

“Upstairs. I’m changing.”

He closed and locked his bedroom door, stripped off the pinafore and blouse, removed the bra and padding, pulled on a T-shirt and sweatpants, and attacked the makeup with a cleansing wipe. In his panic, he left the panties on.

When he was reasonably certain that Samantha had disappeared, he opened the door.

He had taken only a few steps into the hallway when he passed the mirror overlooking the staircase.

Samuel froze.

The wig was still on his head.

His heart began pounding again. He rushed back into the bedroom, removed it, and placed it on its stand before returning downstairs.

Lily was standing near the counter, looking at the plate he had abandoned.

“You’re so weird.”

Samuel tried to keep his breathing under control.

“Why?”

“Why would you heat up your dinner and then go upstairs to change while it gets cold?”

He picked up the plate.

“You’re weirder. That dinner must have been terrible if you’re already back.”

“I forgot my friend’s gift.” Lily grabbed a small wrapped box from the counter. “I only made a quick detour to pick it up. I’m still going.”

“Oh.”

She studied him for a moment.

“Are you okay?”

“Fine.”

“You look nervous.”

“You almost gave me a heart attack.”

“By coming home?”

“By opening the door like a normal person.”

Lily shook her head.

“You really are weird.”

She left a minute later.

Samuel remained in the kitchen until he heard her car pull away. Only then did the tension begin to leave his shoulders.

His phone vibrated on the counter.

A new message.

Congratulations on your prize, Princess. You’re going to look adorable.

Samuel stared at the screen.

Another message arrived.

Remember, tomorrow is the Patron Reception. Cocktail dress, heels, pretty makeup—and, most importantly, your guest.

Then came a third.

I probably don’t need to say this, but Samuel isn’t invited. How exciting! I can’t wait to see Samantha again.

The familiar sickness returned to his stomach.

He had spent days postponing the question of what he would wear. Now the reception was tomorrow, and he still had no answer.

Samuel climbed the stairs and pulled the four garment bags from the back of his closet. He laid them across the bed, then retrieved the only pair of heels Samantha owned—the same ones she had worn to the Graduation Gala.

The sight of them brought back memories of that evening.

Samantha in the fuchsia gown. Her elegant hairstyle. The carefully applied makeup.

That reminded him of another problem: his hair and makeup. The simple routine he used for Willow House would not be enough for a formal reception, and he was not willing to experiment with either of them the night before.

He opened his conversation with Emily.

Samantha: SOS.

Emily: That sounds serious.

Samantha: Patron Reception tomorrow. Cocktail dress. I need help with my hair and makeup.

Emily: What time do you need to be ready?

Samantha: Seven.

Emily: Come to the salon at five. Bring the dress.

Samantha: You’re saving my life.

Emily: I’ll add emergency services to the menu.

Samantha smiled.

At least that was one problem she would not have to solve alone.

Then she began trying on the dresses one by one.

The first was too formal. It was beautiful, but it belonged at a larger evening event, not a reception.

The second was far too conspicuous. Samantha would already attract enough attention without wearing something that seemed designed to ensure every person in the room noticed her.

The third was the simplest and, for that reason, Samuel’s favorite. Unfortunately, the zipper jammed halfway up. After several increasingly frustrated attempts, he decided he could not risk becoming trapped inside it on the night of the reception.

Then there was the fourth dress.

The moment he looked in the mirror, the decision was over.

As if his friends had somehow sensed it, Natalie sent a message just as he finished trying it on.

Natalie: Does everyone have a dress for tomorrow?

The others quickly confirmed that they did.

Maddie: Tell me you tried every single one.

Samuel: Obviously.

For several seconds, no one responded.

Riley: Did you just say “obviously”?

Samuel: How else was I supposed to choose?

Natalie: Which one won?

Samuel: You’ll see tomorrow.

Maddie: That is unbelievably selfish.

Riley: Traitor.

Samuel smiled. He liked the relationship he had developed with them more every day.

Another message appeared, this time from Andrew.

Andrew: Suit and tie acquired.

Samuel: Congratulations.

Andrew: Should my tie match your dress?

Samuel: No.

Andrew: What color is it?

Samuel: Nice try.

Andrew: See you tomorrow, Samantha. Should I pick you up?

Samuel: I don’t know yet. I’m still trying to figure out how to leave without Lily discovering she has a little sister. I’ll tell you the plan tomorrow.

Andrew: Understood.

Samuel hesitated before typing again.

Samuel: Thank you. For everything. I’m serious.

Andrew: That’s what friends are for.

Three dots appeared.

Then another message.

Andrew: Accompanying their cross-dressing friends to formal receptions.

Samuel laughed.

He changed out of the chosen dress, returned all four to their garment bags, and put the heels away.

Tomorrow, Samantha would attend the Patron Reception.

But tonight, Samuel fell asleep smiling.