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  1. Sisters can be strange...
  2. Vacation Gone Wrong
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Rated: 13+ · Interactive · Fashion · #1896737
When your lose your clothes on vacation, you end up dressed like a teen girl.
This choice: Try on the skirts  •  Go Back...
Chapter #2

Sisters can be strange...

    by: Unknown
You look at the inventory of clothes with disgust. You had so quickly told your big sister that you'd find something to wear, but now...now you were having second thoughts.

There's absolutely nothing in there that you'd have the stomach to wear. Not a single pair of shorts, pants, jeans or trousers. Only skirts, dresses, flower-kilts and skin-tight spandex bathing suits. Whomever these clothes belonged to, she was certainly the polar opposite of a tomboy. Hers was the girliest array of clothing that you had yet to lay eyes on.

With patience and some grumbling you sift through the impossibly feminine heap of panties, sport-bras and other frilly things you had no idea how to identify. Oh come on! There has to be something!

Usually you would not even consider imagining yourself opening a girl's suitcase or closet; let alone even try and find something of hers to wear. But as it was, this was an emergency.
You were soaked to the bone and marrow. It was late in the evening and it had been raining with a fury. Before you had succeeded in hailing a cab from the airport, the storm had sprinkled you with several baths worth of water, resulting in all your clothes you were currently wearing to be wet to the insides of their fabric.

It was autumn - the rainy season of common colds. And if you didn't get out of your freezing wet clothes this instant, then you'd be spending your vacation with your sister wiping your running nose and drinking cough syrup.
And yet...the idea of wearing girl clothes...absurd!

A lung-curdling sneeze put you out of your train of thoughts. Damn. Already? Thinking of no other alternative, you discarded your wet clothes. It's just going to be for one night, right? Just me and my sister. Nobody else to see you do this stupid thing. Just at least till your clothes dried. Yet you doubted that they would dry tonight, for the winds howled with rage around the corners of the house, and the fat droplets splattered against the windows with deafening force.

You sighed and picked out some choices. The least girliest you could obtain. Not that that helped much. All of the damn clothes were as girly as they came. Shivering in your birthday suit, (after drying yourself with a towel) you started donning something.

First, for dignity's sake, you covered your privates. Obviously with a panty, the only avaliable substitute for briefs. It was a white cotton one, with frilly pink lacings on the edges. Ugh. But at least it didn't have a bow-tie in the front like the rest. Unfortunately for you, you were a bit cramped in the front sector; obviously they weren't made to contain boys...

Next a shirt. A blue one. Least it wasn't pink. Discouragingly however was that it had a v-neckline, and a curving waistline running from the hips. A dead give-away that this was indeed a girl's shirt. Grumbling, you pulled it over your torso. You then found it to sit tightly around your sides, but loose on your chest. Weird. What kind of shirt was this, anyway? For some reason the stretchy material felt comfortable and soothing against your skin; as if the shirt felt nice to wear. You dismissed that thought quickly.

Finally, the last item. You considered yourself lucky that you found it, whatever it was. You thought it was some kind of jean shorts. Well at least not a dress.
Without wasting time, you put that on as well.

To your horror, you realized that the jean shorts had no leg pipings!!! It was a damn denim mini skirt! It hugged you snugly and made your movement limited as you couldn't run or pull your legs up for more and 40 degrees. Oh forget it! I'm pulling this off!

Before you had time to reflect on this conundrum, your sister opened the door and walked in.

"Jacob, you alright in there? You've been a while. I was getting a bit worried-" she stopped, wide eyed.

You both stared at each other in mutual silence; your face resembling a bright Christmas ornament. Oh this the pinnacle of the word awkward between family members. You can just hear your sister thinking about like what a weirdo you must be looking like.

"Aaaaah. You look so cute!" she announced after several motionless moments. Heh? What did she just say?

"What?"

"You're adorable!" she exclaimed as she came to hug the air out of your windpipes.

"Let go of me!" you said irritably.

"Oh come on. I never did have a little sister to play with. You look so sweet in those misfitting clothes." Man, sisters could be weird!

"Are you insane?"

She took out her cellphone, ready to photograph you, but you intervened in aggression: "NO! What are you doing?!" Too late. She had you digitized before you could block the flash with your palm.

"See? Don't you look nice? The skirt suits you." she pointed the picture at you.

"I look like an idiot."

"Yeah. But after a few careful touches you could really fit in those!"

"No I wouldn't. Delete that picture!" you demanded.

She didn't seem to be listening to you; as if she was in a world of her own. She eyed you with an index finger supporting her chin, the same as a fashion matron would inspect her models.
"Mmm. Your shoulders are actually quite smooth. Not very bony. You could get away with string tops easily. And you have abnormally wide hips for a boy. With the right shirt we can even replicate a waistline. And you have a round chin. Wow. You'd actually make a great crossdresser!"

"What the heck are you talking about?" you said, now thoroughly annoyed. First she said you were cute in a skirt, now that you'd make a great crossdresser. Yep. She's lost her marbles.

As if realizing for the first time that you could hear her talk aloud, your sister answered you: "Jacob. Come on have a little spirit. This could be fun."

"Fun? What part? Looking like a moron?" you said.

She looked a bit torn, as if whether considering whether to ask you something: "Please Jacob. This would mean a great deal for me. I never had a little sister to toy around with."

"Tough. Your not going to anytime soon. I'm wearing this till my old clothes dry, then they fly out of the window." You turned to walk away, but Sarah would not be so easily discouraged. She pulled your arm.

"Wait, wait. What if I told you I'd pay?"

You stopped at that.

Greed is a funny thing. It makes you forget your morals, your pride, your principles and even your embarrasment. Your eyes shone with dollar signs as your faced back to your sister.

"Oh yeah. How much?" you asked, abnormally curious.

"15 000 rubles if you will dress for me for the vacation." Holy ####! Ka-ching! That's almost half a thousand dollars! Your jaw would have dropped past the earth's crust had there not been a floor to catch it. Your sister must REALLY be wanting to see you as her little sister.

Sarah smiled. She knew she had you with hook, line and sinker. She was going to enjoy this immensely.

What happens next?
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