Spending Vacation as a Girl

I finally graduated high school, and as a treat, my sister is taking me out of town to a nice fancy hotel near the beach to have fun! It is quite a drive across state lines to the hotel, but, while I might be exhausted, I’m also super excited as I climb out of the car, and look up at the huge building.

Of course, we can’t just go straight to the beach or pool quite yet. We have to check in and drag our luggage upstairs. I eagerly stand behind my sister as she checks us in.

“Yeah, I have a reservation for me and my 12 year old sister Alex,” she says.

I hold my laughter in at that. She already explained this to me earlier, but with the way I dress and act, I really don’t look anything like an 18 year old boy, so it’s easier to just go with this. Also, she pays less if I’m under 13. I’m short, skinny, have long hair, and wear cutesy girly clothes. Right now, that includes a pink skirt, white barbie t-shirt, pink training bra, white tights, and pink shoes.

The man behind the desk looks over at me, then nods his head, and hands my sister her keys. We grab a luggage cart, and take the elevator to the third floor. We drop our luggage off, then return the cart downstairs, and park the car.

“Finally! Can I go to the beach now, Candice?” I ask.

She shakes her head. “I’m too exhausted after all that driving. I’m going to sleep. You can go to the pool if you want, but I would suggest not going to the beach, since the tides might be rough.’

I sigh. “Yeah, yeah. fine.”

I might be an adult, but I’m pretending to be her 12 year old sister, so I decide not to argue with her. Besides, the pool might be a lot of fun, too!

First things first, I follow my sister upstairs, and get changed. I have lots of swimwear, but lots of it I can’t wear in public, due to a certain little situation in the downstairs area. I’m a boy, so I have to be careful what swimsuits I wear. I pick out a swimsuit that resembles a watermelon, with green striped shorts and a red and black swim top resembling a training bra. Once changed, I head down to the first floor where the pools are.

The hotel has pools both inside and outside, including a swim up bar that is situated between the inside and outside area. If you want to swim from inside to outside, you have to swim past the bar. It also seems pretty nice that you can choose to either be in the sun or the shade depending on what you want. There’s also a lazy river, and a kid’s pool. The kid area has shallow water up to about a foot tall, and some water features. There’s an elephant fountain that shoots water out from its trunk, a pirate ship, and an octopus with a slide down its back.

I realize that even with my pretending to be 12, I’m still a bit too old to be playing there, but it still looks like a lot of fun, so I run over to there. There are a few others kids here, most under the age of 6, but there’s also a pair of siblings, a boy and girl, that look to be about 10 running around. I decide to join them. We splash water on one another, run around, play tag, and joke around for an hour or so before their parents call for them. They’ve got an appointment at a nice restaurant soon, and need to shower and get ready for that. They promise to be back later to play.

I move to the lazy river, as I figure I could use some relaxing after all that playing. As I sit down into a tube, a girl, about 15 years old, gets into one nearby.

“Were those your little siblings you were playing with earlier?” she asks.

“No, just some kids,” I tell her.

As we talk, I take note of her cute light blue swimming dress with little yellow flowers down the sides. It’s really cute, though perhaps a bit too childish for someone her age, not that I’m one to judge.

“Cute swimsuit,” I tell her.

“Thanks! You, too!”

She tells me a bit about herself as we float down the lazy river. She’s a 15 year old sophomore from Maine, and her family comes down here to California often. She likes animals, and wants to be a vet.

While I tell her about myself, I do feel a bit bad about lying. I tell her that I’m a 12 year old middle schooler, and that I’m from Arizona, though my parents are from Japan, and my sister goes to school in California, about two hours from here. I don’t tell her about the fact that I’m a guy, or that I just graduated high school. I would probably be burnt at the stake if I said that.

We talk a bit more as we float down the lazy river, but Taylor, as I learn she’s called, is itching for something a bit more exciting, so we move over to the main pool, and race one another. I’m a fairly slow swimmer, so she beats me with ease. Later, my sister Candice comes down, and goes to sit in the sun. She’s wearing a black one piece with open sides, and lots of cleavage showing. She waves over at me, but leaves me be to play with my friend for now.

After about two hours of playing, Taylor’s brother calls her out and they head off. She borrows a napkin and pen from the bar, and writes her number down for me, telling me to call her later so we can set up a date. I blush a bit at the mention of a date, but she just laughs, and squeezes my butt before running off.

“Wow, what a player!” Candice laughs. “So, are you gonna take her on a date?”

I blush, and shrug.

“How about we go upstairs and put that number in your phone ASAP so you can consider it later? You should also take a bath, since you’ve been in chlorine for several hours now.”

“Yeah. I’m also tired, so I’ll probably call it a day after that,” I nod my head. It’s a bit early, but after the long drive here and then running around for a few hours, I’m pretty wiped.

I plug the number into my phone, then climb into the bath to wash off. After I get out, my sister offers to dry my hair. I sit on the edge of the bed, and she sits behind me, her legs to either side. She blow dries and brushes my hair out, then teases me more about my friend.

“So you like older girls, huh?”

“She’s younger than me, remember?”

“Ah, right. So you like younger girls, huh? Should I alert the authorities?”

“Hey! She’s the one who flirted with me! Anyways, she’s only 3 years younger, so it’s fine!”

“Wait, does this make you a lesbian?”

“No! I’m a guy, remember?”

She laughs, and pats my head. “Yes, yes, sweetheart. I’m just teasing you. I’m happy for you! I encourage you to have fun on your date with this girl.”

“Mhm,” I nod my head. She was cute…

I drift off to sleep in my sister’s lap. When I wake up in the morning, she’s moved me so that I’m lying in the bed. I’m cuddled up against her back as she snores deeply.

I get up, careful not to wake her, and start texting Taylor. She says that she’s free later today, and asks if I would be up to going on a date with her. I take her up on that offer, and she tells me where to meet and when. It’s a fancy restaurant, which makes me a bit anxious. Thankfully, I did pack a nice dress, as we didn’t know if we would be eating somewhere nice while we were here.

The dress is a one shoulder red knee length dress with a black ribbon around the waist, tied in the back, and lace details over the shoulder strap. When I meet up with Taylor, she’s wearing a white button up shirt, and a black skirt.

“I’m glad you could make it,” she says, taking my hand.

I’m blushing deeply, and nod my head. “Yeah, I was excited!”

“You know, you’re really adorable,” she tells me.

“Jeez, look whose talking!”

She giggles at that, then walks me in, hand in hand. The restaurant is really fancy and expensive, but thankfully both of our siblings have offered to pay, so we split the bill in half to make things fair.I’ll just pocket the rest to spend on clothes later.

The food is nice, though I find it hard to pay much attention to it when I’m sitting across the table from such a cute girl.

“So, are you into girls?” she asks.

“Yeah, of course! And I can only assume that I don’t need to ask you.”

She laughs. “Yeah! I mean, I’m the one who came on to you, huh? But I also saw you checking some girls out, including that girl at the bar.”

“I was only looking at her clothes!”

“Right, sure. The butt area of the clothes. Anyhow, it’s fine! I mean, I was checking you out plenty enough! How long have you known that you’ve liked girls?”

“Uh? My whole life, I guess?”

She nods her head. “Me too. Guys are just… boring. Girls are so much more colorful and exciting! And especially you! You have such a good fashion sense!”

“You, too. You look really elegant today, and your swimsuit yesterday was really cute!”

We end up talking a lot about fashion. My taste is pretty childish, but Taylor thinks that it’s cute, and thinks that people should wear what they want regardless of age!

“Besides,” she says, “you’re only 12! There’s no rush to grow old!”


I’m a bit more awkward after that, but we still have a good time. We promise to meet up again later, and as we wait outside for our rides to get here, she takes my hands, and turns me towards her. Slowly, she leans in for a kiss, giving me all the time I need to back down if I don’t want to. But I don’t back down. I lean in, and she kisses me on the lips. I feel my heart speed up, and never want the kiss to end. A car honks its horn.

“Alright, lovebirds! Let’s keep it PG-13!” my sister scolds us.

“Sorry,” I mutter to nobody in particular. I get in my sister’s car, and tell her about how the date went while we wait for Taylor’s brother to arrive. When he picks her up, we drive back to the hotel.

“Sounds like you had fun! Lucky you!”

“Do I hear a hint of jealousy?” I ask.

“Ha! Please! I have a girlfriend, too, you know!”

“Yes, and she’s really nice.”

“But I think I know how you feel, now. We’ve always been so close, and yet we now have other people that we care about. Of course, if you do feel serious about that girl, you need to tell her how old you are, and that you’re a guy.”

I nod my head. As much fun as I’m having right now, the fact is that if I want it to continue for longer than just vacation, I need to tell her the truth. Ideally I would have told her before the kiss, but I guess we’re already past that.

I text Taylor, and ask if we can meet up again later tonight so I can tell her some things. She says OK, and promises to come to my hotel room later. The entire time I wait for her to arrive, I shake with anxiety.

Finally, around 8 PM, she arrives. Thankfully, her brother isn’t with her.

“I was hoping it would just be the two of us,” she says as she notices her sister there.

“Leave you two kids alone? Yeah, I don’t think so!” Candice scoffs.

“Anyways, I didn’t call you here for that,” I tell her.

“I’m disappointed to hear that,” she admits.

“I have something important to tell you.”

She looks more serious now. “What is it?”

“I’m a guy.”

She jerks back in surprise, and looks over at my sister to see if we’re just messing with her. My sister nods her head, confirming that I am, in fact, a guy.

“Moreover, I’m 18 years old. I know I said I was 12 and a girl, but-”

“But you lied to me? And we even kissed?”

“I know, but I wasn’t planning on all of this to happen! I like dressing like this, and with how I look, act, and dress, it’s easier to just say that I’m a 12 year old girl!”

“You realize how messed up that is, right?”

“It isn’t like I was trying to do anything bad!”

She looks pissed as her gaze flickers between my sister and I.

“I don’t enjoy being lied to, you know.”

“Of course! Nobody wants to be lied to! But this is why I’m telling you! I want us to continue dating, but I can’t continue lying to you if we do date! Please, understand where I’m coming from!”

“But how much more of what you said is a lie? You’re cute, so I have a weak spot for you, but can I trust anything you say?”

“I’ll tell you all about me – the real me! Much of what you know is already true, about me liking cute clothes and being from Arizona. But I’m 18 and just graduated high school. I’ll be attending Tangerine Academy in California starting this fall.”

“And how would they react knowing that you were pretending to be a 12 year old girl?”

“I don’t know, but I would rather not find out!”

She crosses her arms, and glares at me. “I don’t know what to think, other than just being really mad. I’m leaving, and will consider all of this. I don’t know what will come next, but I promise you this: if you ever lie to me again, I will personally ensure that you are no longer a boy.”


With that, she leaves, and I collapse into my sister’s arms, crying.

“There, there, honey,” Candice says, patting my hair. “That was rough, but it was for the best. Now she can decide how your relationship can progress. Hopefully she can see through her anger.”

“But what if I get in trouble for this?”

“You won’t, relax. The worst you did was kiss her, and while you really shouldn’t have done that without first telling her the truth, I think that she can look past that.”

I sniffle, and rest my head in my sister’s arms for a bit. Finally, I get up, and take a deep breath.

“I need to take a shower. I’ll be back.”

Before I can leave, my sister grabs my hand, and pulls me back onto the bed with her.

“Sorry about that,” she says. “I just wanted to make sure that you know that no matter what happens, I’m going to b here for you, okay? We’ll be together forever.”

I nod my head, and pull my sister in for a hug. We hold like that for a minute before she pulls back, and holds herself up with her hands, looking down at me.

“You know, I can see why she fell for you. You’re really cute,” she mutters, brushing the hair from my face. She leans down, and kisses my forehead. “Of course, maybe I’m just biased because we share our genetics. After all, I’m pretty damn cute, too! Alright, now you can get out of here.”

Instead of getting up, I pull my sister down, and hug her tight. Her forehead hits my nose, and I let out a quick yelp of pain. She laughs at that, then gets back up, and pulls me to my feet. She’s dead asleep by the time I get out of the shower. I get in bed beside her, and try to fall asleep, though I have trouble after what happened today.

In the morning, I get a text from Taylor. She says she wants to meet up with me again today, this time in her room. I’m uncertain about it, but decide to go for it. I’m unsure how to dress, but decide to wear a flowery beach dress.

“Good luck, heartbreaker,” Candice says, slapping my butt as I finish dressing.

“Shut up,” I roll my eyes.

I knock at Taylor’s hotel room door, and she lets me in soon after. She’s wearing a crop top and denim shorts. She motions for me to come in, and I do so. The room is empty save for us.

“So, what did you want to talk about?” I ask.

“Like it isn’t obvious? It’s about last night? Are you actually a guy?”

“Yes. I’m sorry I lied to you.”

“Prove it.”

“How can I prove that I’m sorry?”

“No, prove that you’re a guy!”


“Life up your dress, genius!” she rolls her eyes.

I gasp. “No! I can’t!”

“Chill! I’m not planning anything weird, I just want confirmation! Besides, you’re wearing underwear, right? Or were you planning something?”

I sigh, and slowly lift the dress to reveal my flower print panties below. Taylor stares for an uncomfortably long moment, then signals for me to put the dress down.

“Alright, I believe you, though I admit I’m not very impressed. You’re really 18?”


She looks at me for a moment, then closes the distance between us, and pushes me against the wall. She pins my arms against the wall, and gives me a quick kiss, before letting me go.

“I still don’t know how I feel, but I want to try. If you’re up for it, I’m tentatively willing to go out with you, at least until our vacation ends. After that, we can discuss things, but a long distance relationship will be difficult. Anyhow, just until summer ends, will you be my girlfriend?”

“Even though I’m a guy?”

“Yeah, even so. I want you to be my girlfriend.”

I’m uncertain what to say, but nod my head. Taylor leaps on me, pulling me to the ground.

“Wait! What are you doing?”

“I can’t hug my girlfriend? Oh, come on! Don’t worry, my brother isn’t here!”

‘Yeah, but-”

“And besides, we’re not going to be doing anything bad anyhow. First things first, though, I want to use you as a dress up doll! Come to my room!”

“Uhh, okay?”

It’s just as she says. For over an hour, she has me try on her different clothes, including dresses, shorts, and swimsuits. I feel embarrassed, but she’s having fun, so I go along with it.

My summer continues like that: going on dates, swimming, and trying on clothes with Taylor either in one of our rooms or at a store. When the vacation comes to an end, Taylor gives me a long kiss, squeezes my butt, and promises that this won’t be the end of things. This, in fact, is only the beginning for the two of us.

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