Jon's steps always echoed through the halls of the school, grabbing the attention of the people on his way to class. The girls, even if just for a quick instinctual glance, would check out his ass and legs whenever he passed by, the heels would ensure that they were the most prominent part of his figure. He was not the most attractive boy at school, but a good outfit, and knowing how to wear it goes a long way.
"Nice heels Johnny, did your mom pick them for you?" Snarked Biff while walking past Jon, having an ugly laugh.
Jon was used to this and simply ignored the heckling as he finally arrived at his first period for today, History with Mr. Jones, an old war vet. Most classes with him were a bore, and today this was no different. Unless Mr. Jones was talking about military history, most of his students were falling asleep, as he showed no passion in his teaching for anything but war.
On most days, Jon would’ve slept through his class, but today he had gym class right after, he couldn't miss it by sleeping too much. And so despite his teacher’s best effort, he was able to power through it. His determination was finally rewarded by the bell, signaling a change of classes, and with no time to spare he made his way out of this boring class, straight to the locker rooms.
Taking the heels off was a relief, though Jon adored them, he couldn’t deny they took a toll on his feet. Looking back to when he started wearing them, he remembered all the blisters and tumbles—he wasn't used to something so tall. But it was all worth it in the end, the added attention he got from the girls was more than enough to make up for the bruises. It also helped that they made him a few inches taller, putting him above most of the other students, something most girls his age liked in a boy.
To replace the heels, he had his special gym shoes, a white and gray Nike’s. They had a bright pink sole, with streaks of the same color all over them. A treasured gift from his father, he gave them to Jon on his birthday, the year after his parents had divorced. His father knew how much Jon loves shoes just as much as he loves sports so this was a natural choice for a gift. Jon loved it, he hadn’t seen his dad much after the divorce, and seeing how much his father still thought about him made the gift even better.
Finishing getting ready for gym class, the other boys started pouring in the locker room. Jon liked to be one of the first in so he could get a set of stretches before class. Before leaving, he double-checked his attire to make sure he was ready for the class. Shoes, check. Shirt, check. Reaching for his shorts, poof, they suddenly became a high-waisted tight pencil skirt, that was also paired with black see-through tights. Skirt and tights, ‘Hmm, a little messy” he said, adjusting the skirt to sit comfortably and continued with his checklist. Everything seemed in order. Satisfied, he confidently strode to the gym, each step with a noticeable sway, due to the restrictiveness of the skirt.
Jon wasn’t quite sure why he wore those tight skirts to gym class, maybe it was the added challenge that enticed him, maybe it helped keep his body cooler, but one thing he was sure of, it just felt right. From middle school, he always wore skirts to gym class, he despised those long shorts you would normally see in a boy’s locker. He didn’t like the way they clung to his body, so from then on he started wearing skirts to PE. At first they used to be those skirts you’d see women wear to work out, they gave him a lot more freedom during class, they were also fun to twirl around. But ever since his mom started working in this new company, he felt the need to wear pencil skirts, which was a bit odd even for him.
Just as Jon was finishing stretching, Biff walked in with his lackeys, in time to make fun of Jon. “Nice skirt princess,” he started, mocking Jon “Trying to grab the teacher’s attention, are you?” he proceeded to the stands, laughing with his gang. Jon thought about responding to him, but today was gym class, nothing would ruin this day for him, it’s what he always looks forward to every week. A bit of mocking and bullying weren’t going to affect him this time.
The rest of the students made their way to the gym just as the teacher arrived. She is a fairly young woman that has just hit her thirties, short in stature and with a noticeable muscular build, that drew the attention of many of the boys. Without any delay, she began organizing the students, splitting them into two teams of five for a basketball game. The boys eagerly gathered around, ready for the competition to begin.
Jon was placed on the blue team, while Biff was on the opposing red team. They take their places on the field and the teacher blew the whistle, starting the game. Despite sporting a tight restricting skirt, Jon was surprisingly agile, being able to play an effective defense to Biff’s offense and even scoring a few three-pointers.
The game was tightly contested. Occasionally Jon’s skirt restrained him too much, allowing the red team to score a few points because of it, but Jon was already used to it, without the restraints the game would have been too easy for him.
With 30 seconds left, the score was 49-48 in favor of blue, and Biff had just gotten the ball. Jon knew that he had to act quickly, otherwise it would be game over for his team. The clock now ticked 20 seconds, Biff was close to the basket, Jon had almost reached him. 10 seconds, they were now head to head, “I got this,” thought Jon. Reading Biff’s movements, Jon anticipated he was going right and positioned himself to block the shot. Biff then cleverly switched directions, tricking Jon, which was already committed to blocking the right side. Jon had to adjust quickly, widening his stance to try to intercept Biff’s shot.
Just as Biff was about to release the ball, a loud ripping sound cut through the gym. The room fell silent as everyone turned to see what had happened. Jon’s face turned bright red with embarrassment as he realized his skirt had ripped, leaving his boxers exposed. In the chaos of his attempt to block Biff, he had lost his balance and fell face first to the ground, his underwear now visible to the entire class, his ass in full display to the whole class.
