How it began

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Oliver was just your average 16 year old guy. Short blonde hair, blue eyes and about 5 foot 8 in height. He was quite a nerdy and smart kid, with mostly top of the class scores on all of his tests. This all changes when Emma came along. She was a "popular kid" and was adored by most if not all of the year however Oliver did not care for such popularity contests of who was the most popular, why they where and when they were, he preferred to sit alone at his lunch table studying over worrying about such things. Emma was a tall, black haired individual with long hair with 2 pink stripes in her hair, she was about 5 foot 9 and wore a smug smile on her face wherever she went.

 Emma was a tall, black haired individual with long hair with 2 pink stripes in her hair, she was about 5 foot 9 and wore a smug smile on her face wherever she went

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One day, Emma decided to walk over to the table ... was sat at and sit herself down next to him. There was an awkward silence for a minute or two before she spoke, she said "Hey boyyy, what's your name?"
He replied with a swift "Oliver, and you?"
She chuckled and replied with "Emma. So, you wanna be friends?"
Oliver said back without thinking it over "Yeah sure."
She looked happily at him and giddily exclaimed "Oh my god thank you sooo much, I love meeting new friends. Do you want to come over to my house after school today?"
He thought it over then replied with "I don't know, I might be busy."
Emma swiftly responded with "Please please please, please come over, it would be so much fun."
He said he would go as he had nothing to do that day. Over the next two weeks the pair grew a close friendship almost as if they were siblings. One time when ... was over at Emma's house she asked him "Have you ever worn a skirt before?"
He answered with "No. Why do you ask?"
She said "Please try one of mine on, I bet you'll look dashing!"
He responded with a quick "no" which shut the conversation down very fast.

One month later...
The pair were once again over at Emma's house however this time playing truth or dare. Emma asked Oliver "Truth or Dare?"
At which he responded with "Dare"
She chuckled, she began to explain the dare to him in the words of "You have to let me be you outfit designer for 1 whole year. I choose what you wear to where and how you wear it. That is your dare!"
He looked around the room dumbfounded and finally muttered "Fine, its a dare I've got to do it."
Emma was very excited, she ran straight to her wardrobe and pulled out ...'s new outfit. She said "It starts today at this very moment."
She handed him the outfit, it was a set of:
1) A pair of black thigh high socks
2) A very short yellow skirt
3) A green sweater
4) and finally a bit of green hair dye
... was ordered to go put his new outfit on immediately, he asked if it was clean and ... responded with "All of it is clean minus the skirt. Teehee"
He had a shocked look on his face as he was surprised that she would give him a pre-worn skirt but he ignored it and went to get changed in the bathroom. He came back wearing his new outfit.

He was next instructed to grow out his hair and add two stripes of green dye like the pink in Emma's hair to his

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He was next instructed to grow out his hair and add two stripes of green dye like the pink in Emma's hair to his.

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⏰ Last updated: Mar 04, 2022 ⏰

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