The Cheerleader Bet

Hello there dudes and dudettes,

I am back with another caption for you all!
This time another Patreon commission, and something slightly more wholesome/less forced than my other works!

This is a commission by Emerald Phenix, about a pair of siblings that make a bet about who gets the better grades.
And as is standard with such captions the guy looses, but this time around he takes it all in stride!

I hope you all enjoy, and until next time stay happy and healthy!

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Andrew and his sister Isabelle were like most other siblings, sometimes they are the best of friends, sometimes they are at each other's throats, but they are ALWAYS competitive.
They often made bets, ranging from simple things like who can do the housework faster or who can get to school faster without any stakes, but sometimes they got a bit more risky, such as this time.
It began harmless, with the siblings teasing each other about being dumb, which after a few days let them to bet about who would get the better grades by the end of the school year.
To make the bet more interesting they decided that the winner gets to choose what the loser has to do during the summer break, being at the complete mercy of the winner.

On the last day of school Andrew happily went home, thinking he had the bet in his bag with his 99 points all across, but he was shocked to see his sister getting the straight 100 points.
"Oh brother, I just know what I am going to do to you! Don't worry, I will surely have fun with this!" Isabelle giggled when she saw that she won, finally able to do what she planned to do for the better part of the school year.

Immediately she grabbed her brother and dragged him upstairs to the bathroom, and once inside she told him to strip down before handing him a razor and shaving cream.
"Now Andy, make sure to shave everything besides your head. And yeah, that includes the eyebrows" she ordered with a smile on her face before leaving the room.
Andrew, saying nothing, just took the razor, went into the shower, stripped and began to shave.
After all this was not the first time one of them lost their hair thanks to a bet, so why would he complain, especially when he was allowed to keep the hair on his head?
Once he was done shaving he rinsed himself off, grabbed a towel that he wrapped around his waist and stepped out of the shower, now being shaven smooth from forehead to toe.

"Hey Bella, I am done!" Andrew shouted, and a few seconds later the door opened and his sister walked in holding various items in her arms.
"Wow, it has been some time since I have seen you so clean" she giggled, making Andrew roll his eyes before she hold out some round objects to him.
"What are those?" he asked, eyeing the object curiously, never having seen something like it before.
"These, my dearest brother" Isabelle explained, holding the globs out like holy objects "are breastforms! And I want you to glue them to your chest!"
This made Andrew stop for a moment. They from time to time had bets that forced them to dress up, especially when they were younger, but nothing ever this extreme.

But instead of declining Andrew just let out a sigh before taking the forms and glue from his sister.
"Well, a bet is a bet" he said after which he slathered the breast forms in glue and pressed them to his chest until the have settled nicely.
"Oh, they look wonderful! But I think you need some counterweight" his sister teased, this time holding out hipforms, and without needing to be told what to do Andrew glued them to himself.
Once that was done he eyed the remaining stuff that his sister had in her hands, and getting where this was all going he just sighed again and held out his hand expectantly.
At that Isabelle just giggled, before handing him a pair of white panties and an equally white bra which Andrew wordlessly took.
Then he stepped into the panties and slid them up his legs, making sure to tuck his wiener between his legs, before clasping the bra around his chest, not struggling at all thanks to his experience.

"Wow, you really look nice like that! I would have done this way sooner if I knew just how good you look..." Isabelle grumbled to herself, bemoaning the lost opportunities.
"But no tiem to cry over spilled milk, after all we are not finished with your dress yet!"
With that she grabbed the white skirt with red trims before motioning her brother to step inside, after which she pulled it up his legs.
Next she grabbed the white top with red letters before making her brother raise his hands and pulling the shirt over his head before finishing the outfit with some red sneakers.
After everything was done the outfit revealed itself to be a cheerleader uniform, the pleated skirt just barely covering the butt enough to be decent while Andrew's slim midriff was left unveiled.

"And now to finish my magnum opus" Isabelle said, looking on in wonder at just how feminine her brother looked with just the clothes before grabbing her make-up supplies.
She started by caking his face in waterproof foundation before moving on to his eyes, gluing false lashes to them and drawing some thin feminine arches for eyebrows.
She then grabbed some lip-plumper and covered her brother's lips with it until they became slightly puffy before adding some dark-red lipstick to his now slightly swollen lips.
The finishing touches were some long blonde hair extensions that she expertly weaved into his hair, making sure to use some glue so they would not become loose.

"Aaaaand we are done!" Isabelle said proudly once she was finished with turning her brother into a sister, and said new sister could only look in the mirror in a bit of shock and awe.
"I have to say sis, you REALLY did go all out this time. I really look like a hot chick" he joked, going along with the silly idea of the bet of theirs.
Because while Andrew is many things, he is not a sore loser, and he would honor the bet and lay in the grave he dug himself with it without complaining, after all his honor demands it.
"So, now that you made me look like a cheerleader, what is the next thing you want me to do? You wanna take some pictures or go straight to filming?" he said with a challenging smirk.
"Well, Andrea" Isabelle said with a smirk, ready to drop the bomb of all bombs on her brother.
"I think we should start getting ready and prepare your suitcase for camp."

"Andrea, huh? Well, it kind ma-- wait, suitcase? Camp?" he just asked in confusion, having no clue what the hell his sister was talking about, only that it could not be anything good.
"Yeah, camp! I have signed us two up for cheerleader camp for the whole summer! Isn't that great?" Isabelle explained with a laugh at seeing her brother's shocked face.
"B-But-- You ca--- What am I sup---" Andrew could only stammer, for the first time since this ordeal began at a loss for words.
"What's wrong, sis?" Isabelle teased. "The bet was that you have to do what I want the whole summer, and I want to go to cheer-camp with my new sister! That is alright, right? After all you don't want to be known as a bet-break, do you?"

Andrew just continued to stammer for a few minutes before hanging his head low and saying with a grumble: "This is gonna be worse than the time you forced me to take ballet classes, isn't it?"
"Well, at least this time I won't you make wear heels" his sister giggled in response.
"Just make sure you don't flash your panties too much during practice. And maybe get some ice before we start to learn splits! But now come, we still have to get your suitcase ready, and I have just the cutest dresses for you to wear!"
With that Isabelle dragged her brother to get ready, with said brother in question just submitting to his fate, after all he would never dream of not honoring a bet, no matter how bad it was for him.