The Boy Becomes A New Cheerleader

Urban
9 min readNov 28, 2023

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Tony enjoyed watching sports. Despite being too small to play, his girlfriend convinced him to try out for the cheerleaders’ squad. A timid boy and four girls. There had never been a boy cheerleader at the school. Then there was this spelling mistake in his name for the regional cheerleading championship.

Tony had always been an athletic kid, but except for soccer and floor exercises in gymnastics, he was too small to play most games. He was now a high school freshman and had, in fact, made the soccer team, but that was not his first love.

He was more of a gymnast, an acrobat of sorts. He could do back flips, handstands, walking, and flip-ups from a lay-down position, and his best trick was the running split, which he did with apparent ease. There wasn’t another boy in the class that could do it, not even the Kung Fu kids.

The only problem was that his school didn’t offer gymnastics as a sport for boys, only for girls. The gym was big enough that they had a permanent practice pad for the runs. He was kidding with one of his girl friends one day about ways to get into the football games for free, and she suggested he try out for the cheerleaders, something a boy had never done before. Tony did have all those moves and was, unfortunately, going to take after both his parents and be short, having probably reached his adult height of 5'5" and 125 pounds.

Brenda was, after all, already on the squad, and she could put a good word in. After some coaxing, he said that he would try out, and if he made it, then he could forget about having to buy a student pass to football and basketball. That was worth something. Tryouts were the second week of school. Tony was going to be a sophomore this year, and he wanted to earn a letter in something. He wasn’t very good at soccer. Maybe he could do it in cheerleading. Well, Mrs. Cling was impressed with Tony’s energy and all those gymnastic moves, so he was invited to join the squad.

Watching a boy wave pom-poms was something new, but they would get used to it. The four girls who were already on the squad liked Tony and were not threatened by his prowess but rather impressed by it, and so they accepted him enthusiastically. He would jump up and wave his pom-poms when the team scored, but he didn’t get all squealy and excited like the rest of the squad. It wasn’t appropriate for a boy, he thought, even though the emotion was there.

His mom was quite pleased, but his father was not too thrilled about his son being a cheerleader. “What kind of job is that for a boy?’ he asked. “Give him a chance, Frank. After all, he’s too small for team sports.” “What’s he going to be wearing, Annie?” “Just the same as the rest of the squad, a tank, tee, or sweatshirt, except he’ll wear pants or shorts, I guess,” she said. “Well, I know they use boy cheerleaders in some colleges, but Tony had better not end up coming off wimpy,” said his dad. “Oh, I don’t think so, dear, she said. The girls seem a little reserved about his being there, but they’ll get over it, I’m sure.”

As practice progressed into October and the first game, Tony and the girls were ready with all their routines. Ordinarily, having a boy on the squad would mean that there would be lifts and some tossing around, but Tony was too small for that.

He was right in the middle as to size, just as likely to be the one tossed. Instead, they featured each cheerleader in his or her specialty. The student body knew about the new cheerleader, and a lot of them were ready to make fun of him, but Tony did an exceptional job that left little room for criticism.

He was there to create enthusiasm, and he did. They were surprised at his gymnastics, and most had not seen a boy do a flying split before. That got its own applause. As the weeks progressed and Tony became really friendly with the girls and less of an outsider, they were more accepting of him. The four of them hung out together on weekends and began to ask Tony if he would like to come along and began, for all intents and purposes, to treat him just as they did each other. He was a little embarrassed and uptight hanging with a bunch of girls, and at first, he refused. However, they persisted in inviting him.

They liked him and knew that he brought something special to the team. So, from then on, if you wanted to find Tony, all you had to do was look for the rest of the cheerleaders, and there he’d be, or they knew where he was. When the school had a dance, he would dance with the ones who weren’t taller than him. Tony’s membership gave rise to another boy joining, but it soon became clear that he was there more to get next to the pretty girls than to do some serious work.

At this point, Tony was still spending some time at the bowling alley with his buddies Carl and Rick. One of the things it was hard for Tony to get used to was the pom-poms and not only being energetic in his performance but also being graceful like the rest of them. However, he soon found himself jumping up and down, squealing, and carrying on with the rest when their team made a goal or touchdown. Being with the girls all the time, the squealing just became contagious. It was so subtle, he didn’t notice his transition to a squealing teen. They worked on both the football and basketball games.

Gradually, the sharp edges of his performance disappeared to be replaced with all of the aplomb that would have been expected had he really been one of the girls with all those gymnastic talents. Mrs. Cling seemed pleased with the streamlining, which made him seem more ‘one of the group’ rather than a lone boy on the team. Except for the red pants and no bumps in his sweater, Tony could now easily pass in the upcoming cheerleading competition if it were not for the fact that he was a boy. There were no provisions in the rules for accommodating a male in the competition. Boys were not at all common as yet, at least in his district.

She kept working on a way to get around that. He did have long hair, which he kept in a ponytail at the nape of his neck, and he did wear an earring, like most of the guys on the athletic teams. He wore the same saddle shoes and socks as the girls, too. Brenda had given him a cheerleader’s bracelet to wear, which he wore to school most of the time. It was quite feminine, but it was, after all, a gift from a girlfriend.

How could he not wear it? She was nice, and they became rather close during the season. It was time to submit applications for the competition, and Janice, their coach, submitted the applications for all five of them but made a slight error and spelled his name TONI. When she handed the applications out for their signatures, Tony was quick to notice this and was going to make a big deal of it but then thought, What the heck, I’ll just sign it the way she wrote it, and so he did.

And, coincidentally, Brenda asked him if he was looking forward to having to shave one day. He said that he’d watched his dad have to do it every day, and it wasn’t really one of the things about adulthood he was looking forward to. Brenda told him that he might not have to. “What do you mean? he said.”

“My mom has some pills that will help you out with that if you want to try them. They’ll probably keep it from growing. She’s making me take them. You could just try two or three a week. I really think it might help you.” “I’ll think about it, Brenda, and thanks.” Brenda, it seems, wanted a closer, more homogenous group.

The committee’s acceptance letter came and stated that their five girls would be welcome and that they were looking forward to meeting them. Well, her five girls? They could only compete on that basis now unless she wanted to jump through a lot of bureaucratic hoops or just go with a team of four, but what was she going to do about Tony? His gymnastics were an impressive contribution to the squad. She decided to pass out copies of the letter and drop the matter into the team’s lap.

They were all shocked, and needless to say, Tony was a little beside himself. He had picked up on their mannerisms and gestures, giggles, and general good humor, all of which now seemed to be continually plugged in, but go to the competition as a girl? Brenda was the team captain and his best friend on the team, so she took it upon herself to talk it out with him. “Tony, I know this is quite a shock, but if we don’t compete the way we were entered, then we can’t compete at all, and I just know that with all your gymnastics, we can win. Won’t you please consider it for me?” she cooed. Since it was Brenda doing the asking, he said he would think about it.

After all, none of the kids from the school were going to be at the competition, just the other teams and the judges. A week later, he told Brenda that he would be Toni for the competition, and she told his teammates. They were ecstatic. They began to treat him more like Toni and got him a girl’s uniform to practice in, complete with a bra, pants, and skirt. They quickly decided Toni should wear a very tight control panty under ‘her’ uniform panty just to be certain.

The skirts were pretty short, after all. “Brenda.” “Yes Tony?” “I think it might be the right time to try those pills now. I have a feeling about something.” “OK. I’ll bring you some.” He began taking one every other day or so with no apparent ill effects. Tony wasn’t stupid. He knew what they were, but they were for keeping you from getting pregnant, and he sure knew he couldn’t do that, so what harm could they do except keep his beard from growing?

Unfortunately, biology was not on Tony’s curriculum, so he altered the routine to take 5, then 6 a week. Toni was rather enjoying ‘her’ new level of acceptance and began wearing ‘her’ ponytail with a Scunci (otherwise known as a scrunchie) holding it rather than a rubber band. ‘ She’ also began wearing that tight panty all the time to get used to the confinement so it would feel natural and not affect ‘her’ performance at the competition, especially when she did a split, except on the days she had gym class.

‘She’ also needed some practice in the best way to hide the obvious and found that he could actually put part of himself back inside and push the other one down and back. It was a little uncomfortable and he had to sit to pee, but he was getting used to it. Brenda talked him into getting his other ear pierced and, while not wanting to wear two earrings to school, just switched the stud from his left ear to his right while at school and it was healing.

He was wearing them both most of the time, however, when not at school. Brenda even got him a pair of little gold hoops for his birthday, and he took to wearing them all the time, both of them. Rather than subject Toni to any ridicule, they decided to hold their last couple weeks’ practice for the competition after dinner rather than right after school, having the gym all to themselves so he could get used to being Toni, his girl self. Well, they had him in the weighted bra and a skirt, but he still didn’t pass because of one tiny inconsistency — no makeup.

READ THE STORY — https://www.patreon.com/posts/93451611

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