Holiday From His Own Gender

This is a top tier Reward story for one of my GenderPlay Legends! Thank you so much for being a top tier supporter! I hope you enjoy what I came up with :)

Holiday from My Own Gender

Narrowing his eyes as the Spanish sun beams in through the large airport windows, Trent waits patiently at the baggage carousel with his family.

“How are we feeling gang?” Erin, Trent’s mom asks, trying to rally everyone’s spirits.

Trent’s dad, Lee, doesn’t react, he just focuses on the moving track of the carousel. Isabell, Trent’s nonidentical twin sister looks up from her phone.

“I’m ok Mom,” Isabell replies with a smile. “Although my cell doesn’t have any signal.”

“Trent?” Mom then asks, nudging him as he stands beside her. “Excited we are finally here?”

Lost in the music blaring from his headphones, Trent looks up at his mom with a frown as she nudges him.

“W-wha?” Trent says, grunting as he pulls one headphone away from his ears.

Erin rolls her eyes as she gives her son a wry smile. “Are you excited to be here?” she repeats.

“It’s a little hot,” Trent replies, with a shrug of his shoulders. “And my phone doesn’t have any signal here. But yes, very happy we are finally here.”

“No signal? Neither does mine!” Isabell shrieks, holding out her phone. “I can’t get onto Instagram! Will the villa have Wi-Fi?”

“You two!” Erin sighs, looking at her husband for support. “Can you believe these two, Lee? We bring them to Spain and all they care about is phone signal!”

Lee still isn’t listening, he’s playing sherpa Dad and is focused on getting their stuff.

“Lee!?” Erin moans, nudging her husband in the side. “Are you listening?”

“Huh?” Lee grunts, giving his wife an odd look.

“Might as well talk to myself,” Erin huffs, folding her arms. “Your children are moaning about the phone signal here.”

“Kids,” Lee scolds, half-assing a telling-off as he instantly returns to facing the opening in which the bags are due to appear.

Trent and Isabell grin at each other as Erin puts her head into her hands in disappointment at her husband's behavior.

“Here they come!” Lee says, leaning so close to the belt he almost falls on it.

The carousel quickly fills up with bags as the entire family focuses hard on spotting their stuff. One by one each family member grabs their bag with a smile and a sense of relief.

They’d gone with a cheaper airline, so they could afford to rent a private villa. They’d also heard of all the issues of missing baggage with the cheaper airline, but decided it was worth the risk.

Eventually, the carousel empties, and the crowds of people leave. However, poor Trent stands dejected at its side still waiting for his bag.

The silence of the arrivals lounge is eerie as the family waits patiently. They are the last ones left. Just watching the metal conveyor belt go around and around.

“I knew it!” Lee complains, kicking the side of the baggage carousel. “They’ve bloody lost some of our stuff!”

“W-what am I going to do?” Trent asks, looking up at his mom with worry. “I had all my favorite stuff in that bag!”

“I know Hunny,” Erin replies, trying to comfort her son with a smile. “I’m sure if we ask someone, they will help us.”

Isabell only sees the funny side. With a smug grin, she pokes at her brother. “Ha..Ha…!” she teases. “Trent’s gonna have to be naked all holidays!”

“Izzie!” Erin replies in an instant, giving her daughter a strong look. “Don’t be mean.”

“Yes Isabell Wilks,” Lee says, backing up his wife. “Don’t push it or we will make you share your clothes with Trent.”

In unison, both Trent and Isabell’s faces drop. “No way!” they both complain, in harmony.

Isabell looks at Trent and she gives him a sour look.

“It’s not my fault Izzie!” Trent reacts desperately wanting her to stop giving him a such nasty glare.

“Stop it, Isabell,” Erin interrupts, standing between them. “Your dad was only joking.”

“Joking—yeah….,” Lee says sarcastically, spotting a member of airport staff. “Look a person. Let me go talk to them. I’m sure it’s just a mix-up.

It’s to no luck. Trent’s bags are nowhere to be seen. Hours after landing, they finally talk to a flight rep, and they learn his luggage is on another flight in another direction.

It’s an instant downer on their holiday. Trent doesn’t know if he should be angry or sad. All he knows is that he’s probably never going to see his stuff again.

The taxi ride through the sun-licked Spanish countryside was long and silent. Well, especially for Trent. Erin does try her best to try and cheer him up, but it’s to no avail.

As the family pull up to the Villa they’d rented for the next two weeks, they all but forgot about Trent’s bags. It’s massive, overlooking the entire town below and the bright blue Mediterranean Sea. If anything, it's more beautiful in person than it was in the brochure.

“Look at this!” Erin beams, her smile as bright as the afternoon sun. “Gang, It’s amazing!”

“Sweetheart!” Lee gasps, at the view. Cuddling his wife from behind, he fondles her and they both begin to laugh and flirt.

“Gross!” Isabell whines, looking away from her parents in disgust.

As they enter the home and take in their new life of luxury for the next two weeks, they all start exploring the villa.

Isabell quickly picks the biggest bedroom as hers. Trent finds the pool and he’s delighted at how big it is. Erin and Lee stand on the balcony of the villa looking over the town below. They are all thrilled.

For Trent, the high is short-lived. Wanting to lay claim to his own room in the large villa, he remembers that his baggage is missing.

Trudging up to his mom, who’s gazing in amazement at the size of the flat screen hanging from the living room wall, he makes himself known

“Mooooom,” he whines, causing her to look around confused.

“Sweety?” Erin answers, pointing and making faces of surprise at the large TV.

“What did they say about my suitcase? Are we going to be able to pick it up tomorrow from the airport?” Trent asks, ignoring her silly expressions.

“Oh, erm…,” Erin scrunches her face to think. “Your Dad spoke with them. You should go ask him.

Trent nods as his Mom turns on the TV. As he walks away, she screams out that the TV programs are in Spanish.

Trent finds his Dad checking out the large, open-plan kitchen. He’s gazing out at the scenery. Lee understands why his wife was so adamant about this place. With the stunning views of the sea and mountain from its large open windows, it’s no surprise the villa costs so much.

“Yo dude…,” Lee greets, as his son approaches.

“Mom said you spoke to the airport people about my stuff,” Trent says, standing beside his dad whos still looking longingly out the window.

Lee slowly turns and looks down at his son with an awkward expression. Rubbing his chin, he mumbles for a moment before speaking.

“Umm….it’s good news and bad news,” Lee answers, nervously scratching his ear. “Bad news is: they’ve sent your suitcase to Norway.”

“Whaat!?” Trent groans, allowing his arms to drop lifeless to his sides.

“Don’t worry!” Lee forces a smile. “The good news is that it’s likely we can recover your stuff from the airport back home.”

“Airport at home!?” Trent kicks out at the floor. “What am I going to do without clothes for two weeks!?”

Lee looks frantically around the kitchen, avoiding any and all eye contact with his son. “Erm….wear….your sister's stuff?”

“Dad!?” Trent whines. “I can’t wear girl's clothes!”

“Oh…,” Lee waves away his protests. “We won’t be expecting you to wear her bras or anything. I’m sure she’s got some shorts and t-shirts packed.

“No way! Can’t we just go into the town and buy some more!?”

Lee moves to the kitchen counter and starts to open the drawers. He’s doing everything he can to avoid looking Trent in the eyes.

“We aren’t made of money Trent,” Lee explains, poking at some of the buttons on the double-sized oven. “I didn’t think it would be an issue.”

“Dad!” Trent stamps. “No way am I wearing Izzie’s clothes. Boys don’t wear skirts and dresses!”

Lee stops messing with the oven and turns to face Trent with a smug know-it-all smile. “Some boys wear dresses,” he replies confidently

Trent’s mouth falls open at what he’s being told. “Would you wear Mom's dresses!?”

“No son,” Lee scoffs, waving away his comment as stupid. “That's because I didn’t forget my luggage.”

Pulling a sour face, Trent gets a little angry. “I didn’t forget mine! It got lost!”

Lee rubs his face again as Trent angrily glares at him. Nervously laughing it off, Lee places a comforting hand on his son's shoulder.

“You wanna go to the water park?” Lee asks gently.

“Yes,” Trent answers with a frustrated pout.

“You want to go to the theme park?”

“Yes”

“You want to go out on the private speed boat?”

“Yes, dad!”

“Well,” Lee says delicately. “If we go and buy you clothes, we might not have money to do any of those things.

Trent looks into his father's eyes and he can tell he’s telling the truth. However, he doesn’t want to believe it!

“MOOOM!” Trent cries out, screaming down the house.

Appearing from the living room in a blind panic, Erin scurries into the room. “What's going on!?” she asks with her fists up ready for action.

Following behind her is Isabell. She’s just as curious as to why Trent’s crying out like a baby.

“Dad is telling me that I have to wear Izzie’s clothes for the rest of the holiday!” Trent shouts with emotion.

Erin lowers her fists and beams a big smile at Trent. “Don’t get upset. We thought you wouldn’t mind. I mean, it’s only for two weeks. No one knows us here, so don’t worry about that.”

“Wait,” Isabell interrupts, on hand onto her hip. “I didn’t agree to that.”

Erin gives Isabell a stern look. Putting both her hands onto her hips, Erin makes a more sassy pose than her daughter.

“Like Oh My God,” Erin says, teasing her daughter by mocking how she speaks. “You’ve brought enough stuff to cloth all of us Izzie. I’m sure you can lend your brother some tops and pants.”

“Stop it, Mom!” Isabell replies annoyed at her impression. “This is so not fair on me.”

“Think how I feel,” says Trent.

“It’s only for two weeks guys!” Lee laughs, trying to lighten the mood. “No one will even notice that you’re wearing girl's clothes, Trent. You and your sister are the same height, so it really shouldn’t be a big deal.”

“And what if I want to go swimming!?” Trent asks with a sour tone, knowing he’s losing the battle.

“We will cross the bridge when we come to it,” Erin chuckles, rustling her son's almost shoulder-length hair.

Later on that evening…..

Having been a bit mopy all afternoon, Trent and Isabell stand in her room looking at her two unopened and unpacked suitcases. Isabell unzips one and folds it open. Trent winches at the colorful skirts, shoes, and pretty-looking clothing.

Isabell starts digging through the clothing as she moves a pile from the suitcase and onto the bed.

“So what do you wanna wear?” Isabell asks with a slightly annoyed tone.

Trent folds his arms tight at the sight of his sister's frilly underwear. “I don’t know Izzie. Some jeans I guess and a t-shirt.

Isabell looks around at Trent, who’s standing behind her. She pulls a face of concern.

“What?” Trent asks, reacting to the worry on his sister's face.

“I……..,” she says slowly, giving her brother a nervous grin. “Haven’t packed any Jeans, Trent. It’s hot here and I didn’t think I’d wanna wear any of my skinny jeans.”

“You…..,” Trent says, pausing to stressfully rub at his face. “Don’t….have any jeans packed?

“No.”

“Izzie!?” Trent criticizes, shaking his head.

“Well, I am sorry!” Isabell complains back. “I didn’t pack with you in mind. Why don’t you go ask dad for some jeans!?”

Trent lowers his head and looks at his petite male frame. “They don’t fit,” he answers reluctantly.

“Well don’t complain then,” Isabell groans, turning her attention back to the pile of clothing she’s made on the bed. “How about some yoga pants?”

Pulling the black yoga pants out from the pile, she holds them up. Trent frowns, but Isabell smiles.

“Don’t look so sad,” Isabell mocks. “Just pretend it’s like those times when I’ve dressed you before, but this time it’s ok if Mom or Dad catches you.”

“Please don’t tease me Izzie,” Trent replies, seeing that familiar look on his sister's face. “Mom and Dad aren’t helping me and you know how much I’ve been looking forward to this holiday!”

“Yeah I know,” Isabell smiles. “I’m smiling because I know what I’ve packed and if you want to wear anything remotely like pants, it’s going to have to be these yoga pants.”

Isabell turns around and grabs a small yellow top crop top with very thin straps. “They go killer with a little crop top like this. Super cute.”

“Cute…?” Trent replies, gritting his teeth.

“What's wrong with cute?” Isabell asks, reacting to her brother's expression. “It’s not like you’re a jock or anything, Trent. I’d understand more if you had more muscle on you, but you’re as skinny as a rake! I think I’ve got more muscle than you.”

Trent swallows down his pride and looks past his sister at her clothes on the bed. “What else you got?” he asks begrudgingly.

Isabell throws the yoga pants to one side. “We will put those on the maybe pile.”

Starting to sift through her clothes one by one, she starts making small neat little piles.

“Dress. Dress. Dress,” she says, neatly folding each garment. “Dress again. Super cute dress. My little black dress.

Trent sighs. “Did you bring anything other than dresses, Izz?”

Isabell doesn’t look around or respond. She answers his questions by picking up a few skirts. “Miniskirt. Pleated skirt,” she says with a point to prove.

Letting out a long breath, Trent moves past Isabell and sits on the edge of her large double bed. Isabell stops sort and looks up at him with a cheeky smile.

“What am I going to do, Izz?” Trent groans, lowering his head into his hands. “I can’t wear yoga pants for two weeks.”

Dropping a skirt as she stands up, Isabell just looks at her brother with a vacant expression. “Honesty, I don’t know.”

Trent lifts his head and looks into his sister's eyes. He wants to cry, but he holds it in as she just stares down at him. Their eyes remain locked together for a moment before Isabell looks up at Trent’s hairline.

Reaching for his messy bangs, Isabell uses her fingertips to swipe hair some of his long hair across his face and into a more feminine hairstyle. She holds it there for a moment as Trent looks at her bemused.

“Izzy?” he asks, as she fiddles with his hair some more.

“I think I’ve got an idea,” Isabell replies, searching for a hairbrush in her suitcase. As she pulls it from a zipped compartment in the case, she brings the brush to Trent’s hair.

“Ah not now Izzie,” Trent complains.

“No no,” Isabell smiles, brushing at his bangs. “I’m not wanting to practice on your hair right now—I’ve had a thought…. so just go with it.”

Trent’s curious as to what Isabell is thinking. He sits patiently as she brushes at his hair. Winching at every knot she works through with her brush, she eventually steps back and looks at him from several different directions.

“Izz?” Trent asks again, now super curious by the focus on her face.

Not answering, Isabell grins and turns her attention back to her open suitcase. Reaching back into the zipped compartment, she pulls out her makeup bag.

Dispensing the contents of the makeup onto the bed, she searches for her mascara. Holding the small black tub to reveal the small bristled brush, she holds it near Trent’s face.

“Can I….?” she asks, gesturing for permission to put some on him.

Having had his makeup done by his sister on several occasions, Trent sighs but nods in agreement.

Opening his eyes wide, she runs the mascara brush gently up and down his eyelashes. Feeling the cool liquid coating his lashes, he looks at the concentration on Isabell's face.

Closing the mascara tube, Isabell steps back from him and studies his face. Reaching to adjust his hair once again, she eventually give him wide smile.

“Look in the mirror,” Isabell says, pointing at the large full-length mirror hanging in the room.

Trent gets up from the bed and does what he is told. Having his hair combed over one side of his face, he has to flick his hair so he can see his reflection in full.

She’s feminized his hair and made him look more girly with mascara. “What am I looking at here Izz?” Trent asks, holding hair away from his left eye.

“Just look at yourself close,” Isabell replies. “What do you see?”

“Myself…,” Trent answers sarcastically. “…looking girly.”

“Exactly!” Isabell laughs, standing just behind him. “All I’ve done is styled your hair and put on a tiny amount of makeup.”

“No, sis….,” Trent sighs, already knowing whats shes going to suggest.

“I think you’d totally get away with being a girl while we are here!” Isabell cheers, clapping her hands together. “It’s the perfect solution to your worries about wearing my stuff!”

“No…,” Trent repeats, but it falls on deaf ears.

Before he can do or say anything further, Isabell throws open the bedroom door. “Mom!” she calls out. “Dad! Come here!”

Sighing as he sees his sister's cheerful expression, Trent turns back to look at his reflection in the mirror. For a split second, he doesn’t recognize the reflection as himself. He freaks him out for a moment because he realizes that Isabell might be onto something.

“What what?” Erin says, bursting into the room. Lee follows behind her.

Isabell points at Trent and Trent nervously smiles back. “I totally think Trent could pass as a girl!” Isabell states.

Erin looks a little shocked as she stares at her little prince. Then after a moment, she smiles. Lee does the same, but he waits for his wife's response, not wanting to say the wrong thing.

“I see what you mean Izzie,” Erin reacts, putting her hands together like she’s seen a cute puppy. “What do you think Trent? Could be an eye-opening experience for you!”

Erin turns to her husband to crack a joke. “He’d be having a literal holiday from his own gender!” she says, laughing.

“Good one,” Lee chuckles, throwing his wife a lifelin, but swiftly moving the conversation forward. “How do you feel about this thought Trent? Would be a good solution to the issue—but we wouldn’t want you to do anything you are uncomfortable with.”

Quickly glancing at himself again in the mirror, Trent turns to look at his family all staring at him in anticipation of his answer. He rolls his head. “Ah, fine.”

“Is that a yes to being a girl for the next two weeks!?” Isabell asks, desperately excited.

“Yes Izzie,” Trent replies to fanfare from his entire family.

“Very grown-up decision Trent,” Erin congratulates him. “I’m proud of you and I think you going to learn a lot about us girl this next two weeks. Your future wife will be a lucky woman, having had her man walk a mile in her proverbial shoes.”

“Yes,” Lee agrees, reaching over to pat his son on the shoulder. “Very good.”

Turning his attention to Isabell, Lee looks at his watch. “Do you think you can do a makeover in an hour? We’ve got reservations at the restaurant overlooking the marina. I’d like us all looking sharp.”

“Probably,” Isabell replies with a smile. “Mom, what are you wearing tonight?”

“Erm…my black dress with the high slit,” Erins replies, pleased to have been asked. “What about your Izzie?”

Izzy looks up in thought. “I guess my black dress too,” she replies, then points at Trent. “But I was more asking for what I should dress Trent in. Maybe my red dress?”

Lee gets instantly bored by the outfit conversation. “I’ll leave you girl’s to it,” he says giving his son a cheeky wink.

“Erm, maybe not the red one,” Erin says, continuing her conversation with her daughter. “That’s a little short, isn’t it? Maybe not good for his first night out as one of us.”

Isabell looks around at the pile of clothes on the bed. “Maybe my halterneck?” she asks.

“Have your heels to go with that?” Erin asks, almost pushing past Trent to look at the clothes on the bed.”

“H-heels?” Trent asks, terrified by the thought.

“Yeah sweety,” Erin says giving him a quick smile, before turning her attention back to the clothes.

Watching his sister and mother decide on his outfit, Trent looks again at his reflection in the mirror. It gives him some comfort knowing at least he’s passable.

“Trent!” Isabell looks up at him with a commanding face. “There are razors in my suitcase. Go have an everything shower. We don’t have all night”

“Everything shower?” Trent replies in confusion.

“Oh right. I’ve got this Isabell.” Erins giggles, looking up at him. “It’s what us girls mean by a shower where we shave all over. Make sure you moisturize afterward.”

“Ok…,” Trent replies, a little lost. Reaching for the door handle to leave the room, Isabell stops him.

“Where are you going?” she asks bluntly.

“To have a shower,” Trent replies.

“You can use mine,” Isabell replies, pointing at the razors in her suitcase. “Don’t be too long though. We’ve got to style your hair and do makeup. I’ve gotta get ready too!”

Reluctantly reaching for the razors, Trent sheepishly enters Erin’s ensuite. Grabbing a couple of towls from her side table, Trent locks the door behind him. Looking at the large rainfull shower head, he knows he’s in for a long night.

Erin looks at the bathroom door he’s just closed then turns her attention to her daughter sifting through her stuff.

“I was going to ask him to get a haircut before this holiday,” Erin admits to Isabell with a smug grin. “I’m glad I didn’t. She’s going to look so pretty!!”