A young boy falls victim to prank from his sister and her friend, at the Kentucky Derby.

Hats Off
By Shawna Stimple

Jack Parker had always wanted to be a jockey. There weren’t really many other sports he could participate in. At only 5’5” and 110 lbs., he was almost the smallest person in his family, second only to his sister Gwen, who was only a few pounds lighter. He loved horses, and even though he came from a wealthy family, he wanted to make his living competing, but he promised his mother he would finish college first.

Jack was attending school at the University of North Carolina. Shortly before summer break, his sister had phoned him, and asked if he would like to join her and a few of her friends at the Kentucky Derby. Unbelievably excited, he thanked her and threw some things in a suitcase, and began the long drive down to Louisville.

Once he arrived at the hotel he waited in the lounge for his sister. When she met him downstairs they embraced tightly, having not seen each other since Christmas. Gwen and Jack were Irish twins, Gwen being only 10 months older than her brother. Both had long blonde hair, but Jack’s was usually a mess, stuffed under some toboggan, where as Gwen’s was always perfectly coiffed in a nice style, framing her beautiful face. By contrast to Jack, Gwen was very proud of her affluent upbringing, and dressed the part. She would only be seen with perfect makeup, and stylish attire. Sweaters and skirts mostly, and she always carried a sophisticated demeanor.

“How are you brother dear?” she greeted, wearing a huge smile.

He replied, “Just wonderful. I’m so glad you invited me out. This is a dream come true.”

“Well come upstairs, and we’ll get you acquainted with some of the girls that will be joining us.”

In the hotel room he was introduced to several of her friends, all fairly attractive upscale young women. The only one who caught his eye long enough for him to remember her name was Christy. She too was well dressed, and groomed, but he could see a mischievous spark in her eye, that told him she too was bored with the upper crust lifestyle, and liked to do her own thing as well.

Shaking his hand, Christ said, “Well, won’t you be the luckiest guy at the track tomorrow? Showing up escorted by a bevy of beautiful young ladies.”

Smiling back, he said, “I’m sure I will. Especially if I’m with you.”

“Do those corny lines ever get you anywhere?” she replied laughing.

Lowering his eyes embarrassed, he replied, “I guess not.”

“Don’t be sad. I’m just messing with you. Come on. Have a drink with us and relax.” she said taking him by the hand and leading him over to the mini bar.

The gathering continued well into the night, and alcohol was abundant. When the clock struck 11, several of the girls made their way back to their rooms. The only ones left were Jack, Gwen, and Christy. Jack stumbled over to his suitcase to gather his sleepwear, and when he opened it Gwen looked in it. Gazing upon the mess of unfolded rags, as she put it, a look of anger crossed her face.

With fury in her eyes she barked, “I can’t believe you! We’re going to be on millionaires row. Not the infield. This is supposed to be a social event. Not a kegger.”

Dumbfounded, the drunk boy replied, “C’mon. It’s not that big of a deal. I’m only going to see the race.”

“Not that big of a deal?! When are you going to learn, that sometimes you can’t just do whatever you feel like? I just don’t see anyway around this.”

“I’m sure we can find him something.” Christy piped in. “There’s bound to be somewhere we can find something more appropriate.”

“No. All the stores are closed, and there’s no way we’ll have time to shop in the morning.” Gwen said, still fuming. “This is going to be so embarrassing.”

“I know. Why don’t I just borrow something of yours.” Jack drunkenly giggled. And with that the intoxicated youth. Made his way over to the bed, and passed out flat. Gwen and Christy stared at each other dumbfounded.

It was Christy that finally broke the silence. “You heard the man.”

The next morning, Jack woke up, head pounding. As he stood to make his way to the toilet he felt restricted in his gait. It was as though his shirt had shrunk over night, and was somehow around his legs. Pulling it up and his undies down, he sat on the commode. He started to regain his senses a little, after chugging some of the water that was left by his bed. When he looked down at the rim of the bottle, he noticed hints of pink. That was strange. Had he been kissing a girl last night? Finally finished he replaced his underpants, and thought to himself that they seemed a little smaller than usual, and his legs also seemed unusually smooth. Turning to the mirror, he saw an image that shocked him so bad that he dropped his water, spilling it all over the entire floor.

The image was him, but it wasn’t. It was him, if he were a girl, with her face covered in makeup, hair up in curlers, and wearing a white slip, with hints of matching white panties, and bra underneath. Angrily he stomped out to the connecting door between his and his sisters room.

Entering the room mirrored to his own, he saw Gwen and Christy sitting at the vanity putting the finishing touches on their make up. Gwen was wearing a white halter neck dress with pink polka dots, falling to below knee length, with a slightly flaring skirt. Her feet were encased in a pair of pink open toed pumps with a four inch heel. Her blond hair was curled and gathered to the back of her head in a loose bun. On her head she wore a pink bowlers hat with a white veil turned up around the brim. Gwen was wearing a pink knee length sweater dress with ¾” sleeves. On her feet were a pair of brown heels, with a slightly raised platform at the toe. Her brunette hair was gathered in a bun on the lower right side of her head, and she was wearing a white cloche hat, with a white rose on the right side, accented by a large white bow behind it.

Feeling the effects of his hangover, Jack rasps, “Is this your idea of a Joke?”, pointing at his head.

Christy turns to face him with a sly look on her face. “Oh Jackie dear. You’re up.

Finishing her mascara Gwen responds, “I believe it was your idea of a joke. We just took you literally.”

“What on earth are you talking about?” Jack said, head splitting.

“Remember last night when we were trying to figure out your clothing situation? Well you said you could borrow something of mine.”

“I was being a smart ass”

Christy joined the conversation, “Well then you should have clarified before you fell over dead.”

“C’mon. Help me get all of this off. We need to get me something before the race.”

Gwen shot back, “We’re leaving for the race in 20 minutes. That only leaves us enough time to finish your hair, and get you dressed.”

“Well then why did you let me sleep so late?”

“We figured we’d let you sleep. Most of the things we did, you wouldn’t have been able to help out anyway.”

“How do you expect me to be ready in time?! And what all did you do to me?!”

Christy approached, and took his hand. “You know. Waxing, shaving, plucking, curling, painting, and what not. Don’t worry. You look gorgeous. Just have a bit of fun with it. Anyway, I like adventurous men.”

Gwen added, “Besides. You can either be ready in 20 minutes, or you can find your own way there.”

Jack sat quietly for a second, looking at both his tormentors. He glanced back and forth weighing the most exciting experience of his life, vs. the possible humiliation of being discovered. He thought about how his sister had never done anything to really hurt him. “Fuck it.” came the answer. “You just have to promise not to tell anyone.”

“Don’t worry brother dear, or should I say sister dear. This stays between us. It’s our little secret. No come on. Let’s get you ready.”

And with that Jack was led over to the vanity. After each roller was removed, Gwen began brushing his hair out, while Christy unzipped, the dress bag and removed his outfit from the hanger. Once his hair was finished the had him step into the bright pink garment. After being zipped in, he stepped into the offered shoes, and had gloves slipped over his hands. They removed the captive beads from his ears, and replaced them with pearl studs, and a double strand pearl necklace was fastened around his neck. They placed a hat on his head, handed him a purse, and led him over to the mirror.

After taking himself in, he started to think they might actually get away with this. He was wearing a pink spaghetti strapped dress, with a high waist, and a square neckline that fell to mid thigh, fitting snugly all the way down. The waist was accented by a small ruffled skirt that flared outward slightly from the dress. He was wearing white round toed heels, with pink lining around the instep. On his hands were a set of wrist length white gloves, and in them was a white clutch purse. His head now sported a large white dress hat with a brim as wide as his shoulders, just slightly off center. It had pink trim around the outside of the brim, and a pink ribbon tied around the center, finishing in a large pink puff of lace on the left. From his shining pearls to his glowing complexion to his long blonde hair curling softly away from his face, he looked every bit a southern socialite, ready to attend her first derby.

“I think I’m in love.” he laughed, with a better outlook on his situation.

Laughing hysterically, Christy said, “Well don’t make a pass at yourself. The only place you’ll get is where you’ve already been.”

Gwen took his purse, and remove a lipstick and a mascara wand. Putting the finishing touches on his make up, she says, “Well I guess we should leave if we plan to make it on time.” She then replaces the items in the bag, and they make their way out the door.

Arriving at the gates of Churchill Downs, they meet a gaggle of young well dressed girls. After being introduced to Jackie, a few of the girls start giggling, and ask for the story. After being recounted the story of the night before, they are sworn to secrecy, and the groups made it’s way into the track.

The first stop was the bar to acquire the traditional mint julep, and to socialize. All the girls roamed around, jumping from conversation to conversation, flirting, and drinking. Meanwhile, Christy and Jack, sat at the bar trapped in their own discussion.

“I must say, you’re a good sport about this.”

“Well I usually just tried to go with the flow, and I guess I did kind of ask for it.”

“True true. But I think you are some kind of special. You’re certainly funny. And you have the cutest eyes.”

“Well you’re not to hard to look at yourself. I’d have to say that out of the two of us, you’re definitely the prettier.”

He reached his gloved hand up to stroke her face, but she gently pushes it back down.

“Come on now Jackie. That’s not the way a lady behaves in public. That’s how a lady behaves in private later tonight.”

“Oh right. Sorry. It’s just sitting here looking at you right now, it’s easy for me to forget about this skimpy dress, and this garish hat. Let’s go do something fun, and then we can sort out all that other stuff later.”

“Sounds great.”

And with that, the two began to wander around the stands. They stumbled upon the fashion contest, and dared each other to enter. While they didn’t win, it turned out to be a blast. After that they decided to place a bet. If they won they’d do something amazing together with it. Suddenly the announcer shouted for the fans to make their way to the track.

Leaning over the railing, Jack and Christy watched as the horses made their way around the track. It was exhilarating. Jack only took his eyes away once, looking at Christy, and thinking that today was totally worth it. Just as he looked back to the track, his horse was crossing the finish line.

They hugged each other jumping up and down, the happiest both had been in a long time. Once the excitement settled, they made their way back to the bar area to find Gwen. She was face down on the bar, drooling just a little. With a glance, and a shrug, they each throw an arm over their shoulders, and make their way to the car.

On the drive back they chatted about what to do with the money.

Christy said, “What do you think about heading to Vegas tonight? We could drive all night, all day tomorrow, and the next get a fancy room, and get better acquainted.”

Jack replied, “Sounds great. But first I want to do one more thing.”

Entering their room they helped Gwen over to the bed, and plopped her in. Jack grabbed a few of his things from his suitcase, while Christy removed Gwen’s hat and makeup, and took down her hair. She saw the clothes in his hand and asked, “Do you need help changing?”

His lips shifted to a sly smile, and he replied, “These aren’t for me.”

Realizing what he meant, Christy took the offered clothes, and proceeded to redress the drunk Gwen while Jack took all the suitcases, and makeup cases to Christies car. After they were finished they left an intoxicated Gwen tucked into bed, wearing Jack’s smelliest, dirtiest, holiest jeans and sweatshirt combo, and leaving nothing to change into in the morning. On the night stand they left her car keys, wallet, and her cell phone.

The two pink ladies then sashayed in a comically exaggerative gate, down to the car, waving, and blowing kisses to the bellboys on their way out. Hopping into the car they drove off into the night, laughing the entire way.

The end.