themariogamer

From Bully to Cheerleader

Published: September 22nd 2024, 7:12:57 pm

Hey there dudes and dudettes!

I am back again with a new caption, this time around a Patreon request by
Milo47, who wanted to see a bully getting turned into a docile cheerleader.

This is a Patreon July 2024 request, and I hope you all enjoy it!
And with that I say my goodbyes for now, and until next time stay happy and healthy!

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"Okay, so why am I wearing this again?" Jan asked his younger sister who was just giving him a smug grin while he tried to pull down his skirt to cover his legs at least once, but to no avail.
"Because I need someone to drive me to the school event tomorrow, duh. And you need to fit in with the crowd!" Steph, Jan's annoying younger sister replied in an amused tone.
"I know that. I just never expected to end up like THIS! I mean what is this supposed to be? These are surely not normal clothes" the feminized guy exclaimed, clearly unhappy with the situation.
"Oh don't be like that" Steph said, circling her brother and looking him up and down in glee. "This is just our normal cheer uniform. Granted, it is a bit too small on you, but nobody will mind."
Jan only grumbled at that, clearly minding this situation very much, but he bit his tongue as he knew it was useless and instead thought about how he found himself in this mess.

Just yesterday the 20-year-old guy was your average young adult male, sitting in his room, playing video games and not caring much for anything feminine as he enjoyed his time gaming.
However that came to a halt when his door suddenly opened and his sister Steph entered, making him groan in frustration as he paused the game he was immersed in at the moment.
"What do you want, pipsqueak" he gruffly asked, not even bothering to look at her as he just wanted her to leave, but she would not give him that pleasure as she gave him a big smile.
"Oh brother dearest~" she sang, and instantly putting Jan on alert. "You remember the cheer festival at school? Well, I need a driver, and since mom and dad are away I thought you could do it!"
"Oh hell no" he immediately said back. "Why would I drive you if I can just chill in my room? And even then what do you expect me to do? Just wait 3 hours for you to come out again?! Just take the bus!"
"But the bus takes nearly 2 hours, while the car ride is just 30 minutes" she whined, but her brother just put on his headphones and resumed. "Fine, then I will take the bus. But good to know that you don't mind our parents finding out about your little secret" she said with a huff before turning to leave.

But before she could leave Jan perked up, slightly confused yet afraid of what Steph was talking about. "What do you mean? What do you want to tell mom and dad? I didn't do anything!"
"Oh yes, you didn't do anything" Steph replied with a smirk. "You know, outside of that one incident in the lockers a few years back? Lia told me how it never made its way to the headmaster."
"W-What?! Oh no. No no no. You can't tell that mom and dad, alright?! If they find out I will either be grounded until I am gray and old, or worse, they throw me out!" Jan started to panic before looking at his sister.
"Okay sis, you have yourself a deal, alright? I will drive you to school, just don't tell mom and dad about this little incident, alright?" he said, sweating heavily as he hoped this would be enough.
"Alright bro, you got yourself a deal! So just get up at 5 in the morning, alright?" she answered, puzzling Jan. "But school doesn't start until 8?" he asked, but his sister was long gone.
Seeing nothing else he could do he just resumed gaming, hoping that his sister would keep her word and would not tell their parents how he once peeked at the cheerleaders while they changed.

The next morning Jan was rudely awakened by his sister at 5am straight, and the groggy and still confused guy was then led to the bathroom by his sister, who looked excited.
"You know I can get ready myself, right? No need for you to get in the bathroom with me" he said, but quickly stopped when his sister handed him a razor and pushed him to the shower. "Shave".
"Huh?" was the only thing Jan could say, still too confused, but Steph gave him a no-nonsense stare. "Shave, now. Unless you want mom and dad finding out stuff they shouldn't find out."
With that Jan gave up, and once his sister left did as he told, cringing with every hair he removed, until the only thing that was left was the hair on his head, and just as he was finished Seph returned.
"You did as I told you, cool! This makes things so much easier!" Steph said with excitement over her new pair before grabbing some medium-sized breastforms, hipforms, and a tube of glue.
"W-What the fuck is this?!" he shouted, looking shocked at what his sister brought in. "Why, this is part of your outfit. After all you complained about needing to sit in the car, so I thought that I can make you blend in with the other students so you could just stay in our school" Steph replied.
But when she saw her brother ready to argue she just gave him an intense look. "Lockerroom" was all she said, and with a heavy sigh and a hung head Jan just nodded, letting the girl do as she pleased.

And so she slathered the forms in glue before attaching them to his chest and ass, making sure to keep them in place until the glue dried before covering his willy in glue and tucking it between his legs.
With the shaping done Steph moved on to the next part, the clothing, though if one would ask Jan
the pieces of fabric his sister was holding could never be called clothes to begin with.
But unable to do anything against his sister's wishes he just had to endure, and soon he found a black G-string and a lacy black bra being pulled up his legs and clasped onto his chest respectively.
After this Steph grabbed the cheerleader uniform and put it onto her resignated brother, and before he knew it he was dressed in the known red-and-white of the school cheer uniform. However, the outfit was a bit too small with the skirt barely reaching over his ass and the top showing underboob.

"Now we only need some makeup to complete that pretty look of yours!" Steph said while grabbing multiple different products from the cabinet, happy how her big brother turned out.
She started by caking Jan's face in light foundation before grabbing a razor and shaving his eyebrows off, giving him new ones by drawing them on expertly.
After that, she took some fake lashes which she glued onto his eyes and covered them in black mascara before using some black eyeliner to give him some doe-eyes.
Next on the list were his lips which she covered in some lip-plumper before she painted them with some neutral nude pink lipstick.
The final part of the transformation was a long brunette wig which Steph glued onto Jan's head, putting it into a ponytail before piercing his ears and adding dangly earrings to them.

"And we are done! With that look you surely will blend in with the rest" Stephexclaimed in glee, holding up a mirror for Jan to see while fighting to control her laughter at the sight.
The boy-turned-girl meanwhile was not as happy with the situation, and he could only stare in shock at his transformation, as a slutty-looking cheerleader stared back at him.
"I-I can't go out like that..." he whispered, still in shock, while Steph just shook her head. "Sure you can. This is the normal cheer uniform after all" Steph lied easily to her brother.
"No! I can't and I won't go out like that! Screw you!" he screamed, though the sister was unimpressed. "Okay, then don't. Though I wonder what mom and dad would say about your peeking. Though maybe they understand if I tell them you always wanted to be a girly girl, which is the reason you asked me to dress you up like that?" she continued with a smile before showing her brother her phone that recorded the transformation in full.
Seeing no other way out Jan once again dropped his head. "Alright, you win. I will go..." he quietly whispered, and Steph cheered, grabbing some heels for Jan to put on before driving off to school.

During the whole trip Jan was very nervous, hoping that they would not be stopped, after all it would be hard to explain why he was driving a car when he looked like a student.
Luckily they arrived with no problems, and after parking a few blocks away they made their way to Steph's school so she could enjoy the cheerleader event.
At the school though some problems arose, many people asking who Jan was, but "luckily" for him his sister always stuck close to him and came to the rescue.
"Oh, this is Jahna, my younger cousin out of town" she said with a smile. "She is gonna join the school soon, and desperately wants to become a cheerleader, which is why she wanted to come to the event! She even wanted to show off some of her cheers and ask if she could join the team!".

Those words made Jan's eyes widen as this was not part of the plan, but before he could say anything the cheerleaders whisked them away, overjoyed with having a potential new recruit.
Though as Steph watched her brother getting led outside to the training field she still was not done with her plan, and pocketing his car keys she went over to a group of jocks.
"Hey Matt!" she greeted. "Could you do me a favor? I have to leave early, family emergency. So could you tell my cousin that I had to leave early once she is done with the cheerleaders?"
"Yeah, I can do that, no problem, Steph" the giant Matt said in a soft tone. "Great, you are the best! Though could you also accompany my cousin? She is afraid to go home all alone, so it would really help her if you big guys keep her safe. And I promise she will make it worth your while, after all have you seen how she dresses? She is totally down on her knees in seconds if you take her home!"
The group of jocks now all grinned perversely, once again agreeing to walk Jahna home together, and as Steph left the school she could only think how this was just the beginning of her plans for her brother, after all years of bullying don't just go away with one little revenge plot.