XaiJu
GenderPlay Books
GenderPlay Books

patreon


Beauty Pageant Consultant

Beauty Pageant Consultant

“That is too much eye shadow, mama.” Leo said to his mama as he took the makeup pencil from his mother, “She already looks like she belongs in an Egyptian mural.”

“Leo Miguel Castillo,” began Teressa Castillo in her commanding tone. Leo Froze. Teressa took the pencil back. “Don’t you ever tell me how to apply makeup,” said Teressa her voice beginning to rise in both pitch and volume. Gabriela, Teressa’s youngest daughter, and the day’s model began to shrink away. “What do you know about makeup?”

“Mama,” said Elana, Teressa’s oldest daughter, truly shocked at what her mother had just said.

“Gram…?” Leo started but was then cut off.

“I don’t want to hear about what your grandmother would do either,” Teressa exploded. “Go home, Leo.”

“Mama?” Asked Leo mouth agape.

“Go home Leo,” Teressa repeated.

_________________________________________________________________

Leo slammed the door of his family’s two-story home. “How dare she dismiss me?” he asked the entryway before he went clomping up the stairs, talking to himself as he went, “Mama thinks she knows so much.”

He took a few more steps. “She thinks she’s just as good as Gram, just because she has won a few local pageants.”

He climbed a few more steps. “She thinks that she knows everything. Can do everything herself.”

Leo took the last few steps to the landing and stared at the family photo that he kept in his wallet. “Gram is only a year retired,” he said to his grandmother’s face, “and mama has already forgotten that we are team Castillo. Not team Teresa.”

Leo started down the hallway. Still, in an agitated state, Leo began to talk to each painting in turn as he passed. “She has, Gabriela, one of the most talented models in the world to work with,” Leo said to a portrait of an older woman in a rocker.

“She has the best clothes to choose from,” he explained to a group of people picnicking in a green meadow.

“And of course, let’s not forget the family name. The family reputation that Gram worked so hard to build over the years. Everyone in the pageant world knows that the Castillo family is the best,” Leo stopped to tell a maiden dancing on a lake.

Then he leaned in and spoke conspiratorially to a man busy kissing his sweetheart, “with all of that I could get a cocker spaniel named Miss Greenfield.” Leo took a moment to smile at his own jest, before exploding, “But she thinks it’s all her. What an ego.”

Leo stood before the doors to the Castillo’s private wardrobe, by far the holiest room in the entire house. He paused for a moment of reflection, said a quick prayer to the fashion gods just in case they really were any, and then opened the door and went in. Most people think of a wardrobe as a large piece of furniture that contains hanging clothes and sometimes act as a gateway to Narnia. The Castillo’s Wardrobe was an entire room filled with dresses, shoes, and jewelry.

Leo had come to two conclusions on the way home. Someone had to teach his mother a lesson, and the only way to do that was to beat her in this pageant. Which had led Leo to two further decisions, that he was the only one who could beat his mother and that since he didn’t have a model to work with, he was just going to have to be the model himself.

Leo went to the attached bathroom and shaved everywhere. He put on black thigh highs, mocha-colored panties, and a matching bra. He slipped size “C” breast forms into the bra and pulled up his hip-enhancing shaping shorts. He put on basic makeup but would wait for just before the show to apply the finishing touches. He looked at himself in the mirror. “All he needed now was a dress,” he told his reflection.

Leo began to look through the clothes. Leo held up a cute princess dress. “Oh, Gram,” Leo said to the room at large, “I can’t believe you saved Elana’s first pageant dress.” It was a pink and white dress with long-sleeved and little green hummingbirds flying around the hem. “If only this still fit him,” He reminisced, “I’d be sure to win.”

The next dress he found was a Lehenga Choli dress. It was sea foam green trimmed in pale gold. Leo loved the dress. He had seen more than one lovely lady wear and win in it. When it caught the light just right it would shimmer in a way that was almost hypnotizing. Leo knew his long jet-black hair and tan skin would go perfectly with the dress. What he didn’t have was a flat stomach and he was not going to get one in the next few hours.

“Time to get serious,” Leo said to himself.

He pulled out two real possibilities. The first was a purple floor-length natural waist gown with a scoop neck and butterfly sleeves. The second was a sleeveless hi-low hem cocktail dress with a black bodice and a cream layered skirt. He knew from personal experience that both dresses fit him. Leo had seen girls win the crown in the purple dress. He couldn’t remember ever seeing the other dress on anyone but him. The purple dress was the safe play. The cocktail dress would be a gamble.

Leo couldn’t decide. He held the two dresses at arm’s length and began to talk to them as though they were people. “I’ve worn you a hundred times,” he said to the purple dress, “You’re very nice.” “But you just seem to call to me. You show off so many of my best traits,” Leo said to the cocktail dress, “my hair, my eyes, and my long legs. Thank God, I shaved this morning.” Gram had taught him the safest path was often the correct one, and so with a heavy heart, he put the black and cream dress back. “I want to win,” Leo said by way of an explanation and apology to the discarded dress and put the purple one on.

Once it was on and zipped up Leo did a single spin in it. Leo always loved the feeling and sound of the swishing skirt. Leo kept twirling. He knew from his grandmother’s teaching the trick to not getting dizzy was to pick a point and focus on it as you turn. Leo chose the clock on the mantel. Round and round he went more than a dozen times. Then he heard someone say, “Always a bridesmaid never a bride.”

Leo stopped as though he had hit a brick wall. There in the door stood his other sister.

“Elana?” asked Leo, who was a little dizzy and more than a little shocked to see her standing there. He managed to recover quickly though, “How long have you been standing there?”

Elana smiles slyly. “Long enough to know that you would look far better in the black and cream dress.”

Leo’s fashion instincts overrode his embarrassment, “Right, but I don’t have the right eye shadow or shoes to really set it off.”

Elana walked over still smiling and looked Leo up and down, “I do.”

“Why?” was all Leo got out before Elana cut him off.

“Because Mama had no right to yell at you like that. How dare she send YOU home. Everyone knows you got a bigger helping of Gram’s fashion genes than the rest of us,” said Elana as she walked around Leo like she was the Earth and he was a purple sun. “And I thought Gabriela was graceful.”

Leo could not believe his ears. His eyes welled up with tears of pride, but before a single one could flow Elana stuck her forefinger right in his face. “Leo Miguel Castillo don’t you dare cry and mess up your face,” Elana ordered, “We don’t have time to start from scratch.”

Leo took several deep breaths and looked upward. He willed the tears back into his tear ducts. Leo was still a little in shock and so just stood there. Elana’s voice soon brought him back to reality, “Well don’t just stand there, get the other dress on and meet me at the car. I’ll grab what we need and meet you out front.”

Ten minutes later as Leo got into Elana’s car he asked, “Do You really think I can win?”

“Like Gram always said,” Elana said and then quoting their grandmother, “You can only win…”

“If you feel like a winner,” Leo finished the saying.

“So do you?” Elana asked.

“More than ever,” Leo responded. Then he took Elana’s hand, “Thank you, Elana.”

“Thank me later,” Elana said starting the car, “Right now we have a pageant to win.”

Comments

Interesting story. Can't wait to see how it works out.

Stephen Dollahan


More Creators