Chapter Two

Taylor so badly wanted to correct her.

He wasn’t a girl. He wasn’t a tween. However, the very fact that Ms. Hamilton assumed both of those things was what kept him from blurting out the truth. What if she knew some of his current teachers? What if the wrong person heard about a dark haired ‘Taylor’ who was mistaken as a little girl? He couldn’t risk it. Plus he couldn’t begin to imagine how she might react if he used his real voice now that he was dressed like this. With that in mind, he squeaked out an awkward, “Mm hmm.” Affirming that he was indeed in fifth grade, or so he’d let her believe for a little bit longer.

Luckily, he didn’t have to speak beyond that. Ms. Hamilton filled the silence herself, talking more about the after school program for girls from the adjacent elementary school. There were plenty of games and activities for everyone, though it was perfectly acceptable to simply spend the time working on homework for those that wanted to be done with that by the time they were picked up.

It didn’t take long before Taylor’s hair was in pigtails. Easily the worst style for someone who wasn’t actually a girl. “All done,” Ms. Hamilton said, stepping back and commenting on how the braids were much better than how his hair looked before. “All the girls here are really nice,” she said, “But you still might get teased if your hair is a mess. Or, you know, if you’re running around in nothing but your panties. No, I don’t want to know; just promise me it’s not going to happen again.”

He blushed again and nodded. Even a small movement like that was enough to make his pigtails shift enough so he noticed them. Between the unfamiliar tightness on his scalp, as he wasn’t used to any kind of braid, as well as how the pigtails were going to continue to bounce and swish slightly whenever he did pretty much anything, he wasn’t going to forget about the girly styling any time soon.

Just like that, it was time for him to actually be taken to the classroom down the hall. The point of no return, in a sense, as it wasn’t too late to come clean and walk away. But Taylor had already committed. Now that he was dressed, albeit in something that was barely better than being naked, it would be much easier to sneak off when Ms. Hamilton wasn’t focusing solely on him.

He followed her to one of the larger rooms on this side of the school. As he stepped through the door, he could see right away that the space had been transformed from the usual classroom set up. Half the desks were stacked up in the corner to make more space for everyone, while the other half were set up in clusters for the girls to sit together rather than how they were normally lined up with everyone facing the front.

There were a good twenty or thirty girls present. Before Taylor could take in much more than that, Ms. Hamilton was calling over a girl who was clearly older than the rest. “Hey, Sarah? Did you check Taylor in? I found her out in the hall.”

Taylor recognized the nerdy brunette immediately. They didn’t really know each other, as he was popular and she wasn’t, but she was in a few of his classes. Was it too late to bolt? Now that he was all dolled up, hopefully Sarah wouldn’t recognize him. However, he wasn’t going to be in whatever system they used, which meant his ‘disguise’ would only work so well if they started asking questions. Short of turning around right now and darting out of the room, Sarah was going to see him either way.

She walked over, tilting her head slightly. “I think so? Check-in was so hectic today. She’s one of our new girls, right?”

“It’s her first day,” Ms. Hamilton said, “Do you mind getting her settled? I need to finish prepping a few more things for this afternoon.”

“Not at all!” Sarah smiled, “Come on, Taylor. Let’s introduce you to some of the girls. What grade are you in?”

It didn’t seem like Sarah knew who he really was; she was treating him just like any other girl here. Still embarrassing, yet not nearly as bad as it could have been. The bad news was, Taylor had just been asked a question. Aside from awkwardly murmuring a couple of words to Ms. Hamilton earlier, Taylor hadn’t spoken since being caught in panties. His real voice would obviously give him away. At the same time, he had no idea how to sound like a girl. Leaning into Ms. Hamilton’s assumption that he was a more shy and soft spoken girl, Taylor squeaked out a feminine, “Fifth grade.” Blushing furiously, he prayed that he didn’t sound like a guy who was faking it.

“Perfect!” Sarah exclaimed, “There’s a spot just for you over there.” She gestured to a clump of four desks, three of which were already taken. The girls were either studying or reading books, since Sarah clearly perceived him as someone who would fit in more with the quiet girls. Objectively, it was ideal, as minimal talking was the best approach at the moment. All Taylor had to do was hang out in daycare until Sarah and Ms. Hamilton were looking the other way. The only minor frustration was that he was a popular guy, and this was the last table he would normally pick. Not that he actually cared, since he had nothing to prove here and nothing in common with anyone in the classroom.

He followed Sarah to the spot near the corner, where she briefly introduced the three girls. Thankfully, she included Taylor’s name, meaning he could stay quiet for the time being. The arrival of a new girl didn’t change much. Once Sarah left, the bookish trio returned to quietly reading/working. While Taylor was relieved that he could just sit there without dealing with any smalltalk as a ‘fifth grader’ that would perpetually threaten to give away his gender, he was aware that he looked a bit out of place without anything to do. Since he didn’t have a backpack here like the rest of the girls, as his was back in his gym locker halfway across the building, he was a little bit nervous Sarah or Ms. Hamilton would ask about that. So far, it seemed like they had both forgotten about double checking the list he wasn’t on.

As for leaving, Taylor still wasn’t sure when the best time to make his escape would be. The classroom had two doors, which was helpful. He really doubted his ability to run in the Mary Janes, in case he was chased, and he also didn’t want to make a scene. Any number of students and teachers could still be around for whatever extracurriculars were going on today, and the only way he’d safely be able to make it to his locker was if there was some degree of stealth and caution used. That wasn’t going to be possible if Sarah was running after. She was a nerdy girl, and he was definitely faster as a baseball player, though could still draw unwanted attention by calling after him.

He was just going to have to bide his time. Maybe there was some game they’d play where he could inch towards one of the doors without being noticed. All throughout his brainstorming process, there was the persistent disbelief that he was actually mistaken as an eleven year old girl by everyone. It was a humiliating low, especially since he had succeeded in overcoming the height thing with his social status. The ‘little girl’ part of it was so much worse, even if he did have long hair.

After another few minutes, Ms. Hamilton got everyone’s attention and announced that they were going to start the afternoon with a few different stations. There would be puzzles at one table, arts and crafts at another, a couple different board games for girls that wanted to play, and the usual option to work quietly. None of the options were particularly active, which Taylor had been relying on. Since he didn’t have any homework on him, not to mention how his assignments were for high school classes, it probably wasn’t a good idea to just sit there and do nothing. So, going with the second best antisocial choice, Taylor went to work on a puzzle.

The girls at his table were a little more talkative than the previous one. He did his best to avoid conversation, keeping his eyes down and only speaking when absolutely necessary. As the ‘new girl,’ it wasn’t that strange to come across as shy/nervous/etc. Taylor just focused on the colorful butterflies he was slowly putting together on the desk in front of him.

Aside from the mental side of things, as he continued to be perceived in such a mortifying manner, there was also the physical he had to deal with. He was wearing a dress. Panties, too. His downward gaze also meant he constantly glimpsed the girly shoes as well. It was all so uncomfortable and unfamiliar compared to what he normally wore to school. Taylor tried to avoid fidgeting, as sitting still was the best way to keep as much focus away from himself as possible.

After twenty or thirty minutes, Ms. Hamilton told everyone that it was time to switch gears. They were going to play a round or two of Simon Says, so the girls could all re-energize. It was easily the worst choice of games, as it meant Taylor was going to be stuck participating while also having to stand more or less in the same spot during all the actions. He was tempted to mess up right away, to be involved as little as possible in the childish game. However, he wanted to stay under the radar; it would be better to play along until at least one or two others were out.

So, feeling absolutely ridiculous in his current getup and as he took his spot for a game he hadn’t played since elementary school, Taylor started copying the moves Ms. Hamilton simultaneously called out and physically demonstrated. “Simon says touch your toes” “Simon says hands on head.” “Simon says stand on one foot.” “Switch feet.” That’s all it took for a couple girls to be tricked. At that point, Taylor was comfortable following through with his plan, purposely falling for the next one so he could go stand off to the side.

He did the same thing for the next few rounds, feeling particularly embarrassed when the actions reminded him of his situation. Not that he needed much of a reminder, when he was surrounded by a classroom of girls who were waiting for their parents to pick them up. Still, something like ‘jump up and down’ made both his pigtails and his skirt bounce, and he also noticed along the way that he was basically the same height as the others. Definitely on the taller side, due to his age and gender, but not by much.

Once the third game was over, everyone was free to go back to the same activities as before, and encouraged to switch stations. Sarah made a point to walk Taylor over to the arts and crafts area, no doubt wanting to nudge the new girl to try different things. She informed him that there would normally be stuff to do outdoors. Since it was drizzling outside, they were restricted to the classroom at the moment. Taylor was fine with that; similar to his worries from before, there was a chance that one or more of his peers were hanging around after school for whatever reason. And, while he normally thrived when it came to physical activities, running around in a pink dress sounded terrible.

Taylor’s athletics were strong. His artistic abilities, however, were practically nonexistent. He settled on a box of colored pencils and a Color By Number book. It was one that had more involved drawings, for older girls to enjoy the simple, cathartic experience of coloring. Even so, he was too old and too mature for the experience. Like the previous table, he kept to himself for the most part, content to be the ‘quiet girl’ as he remained in the daycare classroom way longer than he had anticipated. Going to the bathroom wasn’t an option, either, as Ms. Hamilton had mentioned that girls needed an escort rather than a hall pass or whatever.

Before he knew it, parents started showing up. Not all at the same time, as they all had different reasons for having their daughters stay for an extra hour or so, but enough that Taylor was belatedly hit with a whole new problem. No one was coming to pick him up, as he wasn’t actually supposed to be here. It wasn’t as if Ms. Hamilton was simply going to let him leave when he was the last ‘girl’ there. Did he put himself through this extended humiliation just for her to find out who he really was anyway? Short of falling back on his original thought of making a break for it, he had no idea how that would play out.

As the room continued to clear out over the next ten or fifteen minutes, Taylor continued to quietly stress as he kept working on the coloring sheet. Eventually, Sarah came over. “Hey, Taylor? I’m done helping Ms. Hamilton for the day. Do you need a ride home?”

Was Sarah allowed to do that? Even if she was, Taylor didn’t want her knowing where he lived. Then again, he could always lie and have her drop him off down the block. Wait, then he’d have to walk through his neighborhood in a dress. Also, his car was still out in the school parking lot, while the keys and everything else was in his locker.

Despite all of that, he gave a nod and a quiet, “Yes.” One problem at a time. Right now, the priority was getting home and back into his own clothes; he could figure out the rest later.

“I thought you might,” she chuckled, “Tell you what. Give me a big smile, and I’ll give you a ride. Otherwise, we can go have a little chat with Ms. Hamilton about how you’re an asshole jock who’s secretly a little sissy.”

It took a moment for Sarah’s words to register. The friendly tone didn’t at all line up with what she actually said, and Taylor was also used to her being a nerdy girl who wouldn’t dare talk to a star athlete like that. Of course, he was far more concerned with the fact that the brunette before him apparently did know who he really was. And could easily rat him out if she wanted to.

When Taylor didn’t reply right away, Sarah said, “Go on, Taylor. Smile.” She held up her phone, not making any attempt to hide that she planned on taking a photo. Just for good measure, she added, “Not that it really matters. I have so many good pictures of you. I’m sure the whole school would love to see them.”

This was quickly turning into his worst case scenario. Sarah knowing might have actually been worse than Ms. Hamilton finding out, as she was a peer in a unique position to boss around a boy who normally walked all over girls like her. It didn’t matter that she wasn’t friends with his friends; a single group text from her, and the photos she was referencing would spread like wildfire.

With all that in mind, he forced a smile that wasn’t candid in the slightest. It looked more demure than anything else, with the way he kept his lips closed. “Real cute,” Sarah giggled. She snapped the photo, then took his hand. “Okay, let’s go.”

Taylor let her walk him out of the classroom, where he was assuming the risk of being seen was a lot lower now that so much time had passed since the final bell. The moment they were out of earshot of both the room itself and any parents that were around to pick up their girls on the later end, Taylor said, “Now, can I-”

“Ah, ah,” Sarah cut him off, “When you’re dressed like a little girl, you talk like a little girl. Understand?”

His head was still spinning. And talking in the girly pitch when Sarah was well aware that he was a classmate? It was a lot. He was also in no position to argue when he was still in the middle of the mess that a simple locker room prank had snowballed into. “I just need to go get my stuff,” he said, “I can drive myself.” God, it was so much worse saying full sentences as if he was a female tween, rather than the limited vocabulary he had managed to get away with earlier.

“Don’t be silly, Taylor!” she exclaimed, “A girl your age wouldn’t have any stuff in this building. This is a good look for you, by the way. Who knew that you really pick on girls because you secretly want to be one? Honestly, I’m not sure I would have recognized you if you hadn’t used your real name. But it’s a good thing I did. This is going to be so much fun!”

He hadn’t meant to use his real name! It just slipped out, as he had been flustered from being caught ‘streaking’ through the halls in panties. As for the rest, it wasn’t that Taylor specifically picked on girls. He just tended to tease and taunt the obvious targets; Sarah just happened to be one of them.

“So. Here’s what I’m thinking,” she continued, squeezing his hand and walking him towards the side door that led out to the parking lot, “I can keep this to myself, and I might even delete all the adorable photos from this afternoon. As long as you do a little something for me.”

As in, what? He had no idea what a girl like her would want. And asking meant he’d have to suffer through more of the girly voice. Instead, he kept quiet, assuming she was getting to her point regardless.

Sure enough, Sarah smirked and said, “I think you should come back to daycare tomorrow. In those shoes and another cute dress, of course. Oh, and definitely in panties like the ones you have on right now! Ms. Hamilton told me you were running around in My Little Pony panties? I think underwear like that is perfect for a sissy like you!”

Absolutely not. One day of a humiliating case of mistaken identity was bad enough. “I can’t,” he said, blushing deeply at how he was stuck using the girly voice, “I have baseball practice.” It wasn’t a lie. They didn’t practice on Monday, but he was committed to the team tomorrow.

“Then I guess you have a decision to make,” Sarah shrugged, “Do you want to be a boy, and have everyone know that you’re actually a little girl at heart? Or do you want to be a girl, and continue pretending to be a boy at school? Guess we’ll find out tomorrow after school!” Not pressing for an answer right away, she simply walked him to her car and opened the rear door. According to her, he was both too young and too short to sit in the front seat.

Aside from asking for his address to put into her GPS, Sarah didn’t tease him any further or imply anything else about the obvious leverage that she had. She was content with the sight of him in the rearview mirror, sitting in the back seat as if he was actually a girl who needed a ride home. Meanwhile, Taylor had to watch helplessly as his own car vanished from sight as they turned the corner. He probably wouldn’t get a fine for a single night of leaving it in the parking lot, though it did mean he would have to figure out how to get to school tomorrow. His sister didn’t have her license yet, and he also didn’t have his phone. Until he could figure out how to explain why he was home without his car, it would be difficult to ask anyone for a ride.

Speaking of Anna, there was a good chance she was home. Considering no one two feet away from him had noticed that he wasn’t actually a girl, Taylor wasn’t that worried about darting from Sarah’s car to the house. Getting to his bedroom would be a whole different story if Anna was pretty much anywhere but her own room.

“Here you are, Taylor!” Sarah said, as they pulled up to the curb, “What do you say?”

He had half a mind to just get out of the car. Instead, after making sure both of Sarah’s hands were on the wheel and her phone was nowhere in sight, he forced out a quiet, “Thank you.”

“What a well behaved little girl!” she grinned, “Bye, Taylor. See you tomorrow, maybe!”

After triple checking that no one was walking nearby, Taylor got out of the car and sprinted to the side of the house. He didn’t want to be seen on the off chance that Anna was looking out the window. And while he logically knew that their neighbors likely wouldn’t recognize him in his current state, it didn’t keep him from being nervous about it while it was still light outside.

Slipping in through the garage, briefly stopping to see if there was anything he could use to cover up or change into, Taylor braved the house itself. Calling for his sister was a terrible idea. Instead, he carefully and quietly padded down the hall. Where was the closest change of clothes? Both his bedroom and the laundry room were on the second floor.

Sarah having pictures was bad enough. If Anna saw him like this, he was dead.

Finally, Taylor caught a lucky break. The first floor was empty, and he eventually resorted to racing up the stairs and to his room before Anna left hers. If she was home at all, as she could easily be at a friend’s place. Either way, Taylor made it safely to his bedroom, where he promptly locked the door and closed the curtains.

Safe. For now. Even so, he quickly stripped himself of the dress, the panties, and the shoes. Then he stuffed them under his covers, as if someone would burst in any second and see that he had just been dressed up like a girl. After pulling on a pair of boxers and some of his own clothes, he flopped down onto the bed and took a deep breath. He still had to undo the pigtails; that would just be more involved than changing, and potentially require seeing himself in the mirror with braided hair.

He already knew what he had to do in order to keep Sarah from totally ruining his reputation. That’s why she hadn’t pressed that hard about it. Baseball practice or not, Taylor was going to have to swallow his pride and go through another round of daycare. Either Sarah was assuming that’s what he would do, or she was happy with either outcome.

Speaking of his pigtails, Taylor realized that it wasn’t nearly as simple as showing up to the classroom after school. To keep up the charade, he was going to have to find a new dress to wear. And a new pair of panties.

Without a car, he really only had one option. He was going to have to ‘borrow’ some of his sister’s old clothes, bring them to school, and change into them after P.E. All so he could skip practice for the sake of pretending to be a tween girl for the second afternoon in a row.

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