Not Your Average Teen Boy

Chapter 2: First Day Of School

Jacob was still embarrassed over his sister forcing him to dress up and his mum knowing. But hopefully he could get away from the constant torment of his sister calling him 'sissy' and asking him when they are going out clubbing. Tomorrow was the first day of his new school and he couldn't wait to make some new friends so he can get away from his sister. It was late at night and Jacob couldn't sleep despite his best efforts. All he could think about was that dress and those heels. Thinking back on that moment, Jacob wasn't angry or upset. He kinda liked it. Only until his mum came back, he acted like he didn't like them. He wonders if his sister noticed.
He laid there for another couple of hours before he finally drifted off to sleep.

*TIMEJUMP UNTIL MORNING*

Jacob woke up in a hurry. He overslept and if he didn't get moving then he wouldn't get to school on time. "Way to make a first impression" Jacob thought. Amelia had just left wearing some super high waisted jeans and a cute crop top. She had her hair flowing down ovet her shoulders. Amelia was no doubt trying to be the new hottest girl in the school. Jacob was still having his breakfast. "Your clothes are on the bed already as you are running late" shouted down his mum. What she had actually laid out for him was not really his normal boy clothes but some girly clothes instead. His mum hadn't gone to crazy as she didn't want him to notice and it was the perfect start as he had no time to complain.
Jacob got upstairs and on his bed laid this

He slipped on the jeans. Well eventually as they were girls high waisted jeans. He thought that they were abit high and tight but didn't have time to think about it. He pulled on his shirt that gave him more of a femenine look and his favourite black trainers. His mum looked at him as if she had won something and waved her son off to school.

Jacob had just arrived at the school gates and his sister had already got a group of boys and girls around her. Jacob thought that this couldn't go too badly. Jacob liked to play soccer and when he saw a group of kids his age playing, he decided to go and join them. He heard a wolf whistle but he assumed it wasn't aimed at him. "Nice ass!"shouted someone behind him but Jacob ignored as he was sure it wasn't directed at him. "Nice jeans" said one of the people playing soccer " Where did you get them?"another one asked.
"They're mine."replied Jacob,"Can I play?"
"Sorry, we have already had enough on each team, but meet me in the toilets at break and we can discuss."said the captain of one team.
The bell rang and Jacob was off to his first lesson. Jacob got told to sit on the girls table and all the boys chuckled to themselves. Once the lesson had got underway, the girl sitting to his left said "Hi, my name is Holly, this is Ellie, Sharni, Jodie, Lily and Chloe."
"Hi!!"said all the girls.
"Hi"said Jacob nervously. He wasn't sure why he was put on this table nor why all the girls were acting so nice. They were all very attractive and so nice to him.
"I love your outfit!"said Chloe. All the other girls agreed but Jacob wasn't so sure about it.
"So, what is your name?"asked Ellie.
"Jacob"he replied.
"Since you're on the girl table, we are going to call you Jess."stated Ellie. Jacob wasn't sure about it but he was surrounded by attractive girls so he couldn't disagree.
The bell rang and it was time for break. All the girls wished him luck for the rest of the day and went off to break. Jacob however went to meet the soccer team captain in the restroom. Jacob opened the door to see him.
"My name is Reuben, you want to join our team?"asked he sternly.
"Yeah"replied Jacob politely.
"One issue is we don't usually allow girls to play."he said.
"But I'm not a girl"said Jacob confused.
"Then why are you wearing girls clothes and why were you on the girls table in first period?"he replied smirking. Jacob had no words. He was wearing some really tight high waisted jeans and his femenine body shape was emphasised by his top. "Now I can let you play if you suck my dick like a girl would or you become a cheerleader for our side whenever we have an official school match and wear slutty outfit for the rest of this week." Reuben said. Jacob didn't want to suck his dick so he guessed he had to become a cheerleader and wear something slutty for the rest of the week. Just as Jacob was about to leave, Reuben slapped his ass as he walked past. Jacob's ass jiggled from the impact of the slap. Jacob was powerless and went off to his next period.
Nothing interesting happened during the period but he was invited onto the girls table at lunch. Lunch had arrived and Jacob needed to sign up as a cheerleader. So he asked Holly the head cheerleader. "Hey Holly, can i join the cheerleading squad?"asked Jacob.
"Sure, we would love another fitty in the squad and then you can truly join in on all of the girl gossip as everyone here is already on the team."replied Holly. She gave him a  kit and told him it is a perfect fit and she wouldn't allow him to give it back. Jacob was now on the cheerleading squad, all he needed now was a slutty outfit for the rest of the week. His only option was his sister.