Published: March 30th 2025, 7:24:39 pm
(The first ten chapters are compiled on my SubscribeStar, if you want an easier way to access the rest!)
Taylor’s heart was pounding.
He knew that Anna would be on the other side of the house, since she would be the one answering the door, but that didn’t account for her friend(s). Based on his experiences returning from practice on the nights where Sarah had company over, he was assuming it would be the two or three usual girls that were around. They could just as easily be in the living room or Sarah’s bedroom, meaning he could also run into them in just about any hallway or the stairwell leading to the second floor.
As he quietly slipped inside, he tensed up when his sister yelled, “Coming!!” Anna’s voice alone was enough to make him jump. She was definitely coming down to answer the door. What if her friends were following, to see who it was? The good news was, their house was the kind where the stairs didn’t lead right down to the front door. Otherwise, it would have been impossible for Taylor to make it past Anna without being seen.
It was now or never. Short of climbing up to the roof, which he could do when not worried about someone spotting him in his current get-up, there was only one way to his room. Moving as quickly as he could, stopping at every corner and doorway to check if someone was on the other side, he hiked up his skirt and raced up the stairs.
Good. No one was in the hall. However, Anna’s bedroom door was open and Taylor could hear voices coming from inside. He darted to his room, grateful that his was closer to the stairs than hers, letting out a huge sigh of relief when he had the privacy of a closed door. However, there was no time to catch his breath. Wishing that there was a lock on his door, Taylor wasted no time in kicking off the childish shoes and slipping out of the dress, both of which he shoved into the closet out of sight. In nothing but panties, he opened his drawers to find something normal to wear.
He had completely forgotten that Sarah had taken a lot more than just his boxers; every single t-shirt in his drawers belonged to Anna. The only reason he hadn’t been caught yet was because the non-dress clothes he had been left with had options that were more than just pink and purple. Actually . . . Taylor opened the girly backpack he had dropped on the floor thirty seconds ago in his haste to get out of the humiliating ensemble. His outfit from school was still in there, and there was no way Anna would recognize her simple black tee from years ago. The only reason Taylor wore it to school in the first place was that it looked gender neutral.
Wriggling into his tight jeans and triple checking to make sure that the panties were completely hidden underneath the denim waistband, he made short work of pulling on the t-shirt. Now that he was upstairs and behind a closed door, he had no idea how the conversation was going with Sarah and Anna. Had Sarah introduced herself as his girlfriend? They really hadn’t talked much about how this was going to go, aside from how Taylor was going to somehow end up ‘volunteering’ to take over his sister’s chores.
He was about to open the door to head downstairs and do whatever damage control he could, not that he ever had any luck with that when he couldn’t say anything in Sarah’s presence that she wouldn’t approve of, when he felt the sway of the pigtails as he stepped forward. “Shit,” Taylor muttered to himself. That could have been really bad. He had been wearing his hair like that for hours now, and had been so distracted by everything else that he almost let Anna and company see him like that for no reason.
Quickly removing the hair ties and undoing the braids, he took a minute to get his darker locks back to some semblance of normal. The bathroom was down the hall, and he had already learned that simply wetting his hair in the sink didn’t help that much. Plus the water could be off, depending on the renovation schedule.
“Taylor!” Anna exclaimed, “Are you home?!”
No more stalling, then. At least he got himself sorted out before being called downstairs. His bedroom door was usually closed, so his sister probably assumed he had made it home at some point without being heard down the hall. Daycare mostly lined up with baseball practice as well, and Anna didn’t pay attention to him enough to notice any discrepancies like that in his schedule.
Leaving the sanctuary of his room, knowing full well he couldn’t hide out there while his ‘girlfriend’ had come over to see him, Taylor cleared his throat and said, “Coming!” It was the first time using his actual voice since the last class of the day, which was always a bit of an adjustment regardless of how awkward and embarrassing his little girl voice was.
To his relief, it was just Sarah and Anna downstairs. The other girls must not have been curious enough to see who was at the door, or assumed from Taylor’s name that it had nothing to do with them. Anna also didn’t look particularly smug, at least not when compared to when Taylor needed a ride to school. So, Sarah couldn’t have told her that much.
“Your girlfriend’s here,” Anna said, as if Taylor couldn’t see the girl standing right next to her, “Also, since when do you have a girlfriend?”
That’s what it was. Anna was just confused and/or caught off guard. She was judgmental towards him in general, being his younger sister, but wasn’t nearly as bad as him or his teammates. Instead of making this about him being with some nerdy girl, Anna was just surprised Taylor was dating anyone when he had been single for the entirety of high school.
“You didn’t even tell your sister, Tay-Tay?” Sarah sighed, “If I had a sister, I’d tell her everything!”
Sarah had clearly saved the nickname for this moment, as Anna immediately smirked upon hearing it. “Tay-Tay?” she asked. Just like when his teammates had heard it, the amusement was painfully obvious. “Cute.”
“Just like him,” Anna smiled, “Anyway, are Tay-Tay and I allowed to hang out in his room, or is there a rule about that? We can keep the door open, or whatever!”
With their parents gone so frequently, nothing like that had ever been established. Plus Taylor and Anna generally only had their same-gender friends over. “There’s not-”
“Shush, babe!” Sarah cut him off, “I was asking Anna. You’re the one in charge while your parents aren’t here, right?”
At that, Anna’s eyes lit up. “That’s right!” she said, “I’m the more mature sibling, after all. And our parents don’t trust him at all.”
Total bullshit. They were both old enough and self-sufficient enough to coexist, and stayed out of each other’s way for the most part. “Anna-”
“Shush, Tay-Tay!” Anna interrupted him, mirroring the way Sarah did so, “I’m trying to talk to Sarah.”
Sarah shot him a quick look, subtly reminding him that he was supposed to play along whenever she was having her fun. It was discreet enough that Anna didn’t catch it and, just in case, Sarah distracted her with a question meant to further embarrass Taylor. “Soooo, do we need your permission to chill in his bedroom?” she asked.
“You do,” Anna nodded, “As long as Taylor asks nicely, you should be fine!”
“He can do that!” Sarah said, “Okay, Tay-Tay. You can talk now!”
Thoroughly frustrated by how both girls were walking all over him, when they had literally just met and didn’t seem to be working together, he begrudgingly asked, “Can we hang out upstairs?”
“May we please hang out upstairs,” Anna corrected him.
“May we please hang out upstairs,” he echoed in a flat tone.
“You may,” Anna said, “But leave the door wide open. I don’t want you two doing anything inappropriate while my friends are over. Plus it’s bad enough when I have to hear your music through the wall.”
“What do you say, Taylor?” Sarah asked, always making a point to pivot back to his actual name just enough that ‘Tay-Tay’ was still a little bit fresh despite how it had really taken off over the last twelve hours.
Sounding just as unenthusiastic as before, Taylor said, “Thank you.”
“Why are you so mean to your sister?” Sarah giggled, “You’re so sweet to me! Oh, Anna? Can we come into your room later? I’d love to see your space! And Taylor has a surprise for you.”
More curiosity flashed across Anna’s face, though she shook it off pretty quickly. “I have friends over, but it’s whatever. Come say ‘hey’ whenever. But Tay-Tay has to knock, whether the door is open or closed. House rules!”
That one was actually true. Not that it was an official rule. He and Anna just never went into the other’s room, nor did they have a reason to.
“Sounds good. Let’s go, Tay-Tay!” Sarah took his hand in the familiar way, tugging him towards the stairs and up to the bedroom that she was already perfectly familiar with. Once they were inside, she did exactly what Anna suggested and left the door all the way open. It didn’t give them any privacy whatsoever, which was annoying; while Taylor didn’t plan on doing anything intimate with the nerdy girl, he did want to talk to her about everything she just did with Anna. With the door open, however, he was worried about one of the girls down the hall eavesdropping from around the corner, as they would all be hearing about this relationship development from his sister in a matter of minutes.
Sarah led him over to his desk, where she guided him into the seat and pulled out his mostly complete coloring sheet from daycare. “It would be a shame if we didn’t see the finished product!” she said, setting down a pack of crayons next to it. “Why don’t you get started on that, and I’ll do a little homework? That’s what boyfriends and girlfriends do, right? Spend time together, even when doing different stuff?” She was speaking quietly enough that someone in the hall wouldn’t overhear, since there was a pretty telling ‘we’re not actually dating’ remark in there. She gave his cheek a teasing peck, then flopped down onto the bed.
Just like that, he was put in a bit of a paranoid state as they fell into a silent, productive state. Not that Taylor would call coloring productive. Someone standing at the door probably wouldn’t be able to see what he was working on from across the room; then again, the fact that he was using crayons might be noticeable from a distance. He also couldn’t remember the last time he left his door open. Instead of peace and quiet, like he was used to, he could faintly hear Anna and her friends talking from down the hall. It sounded like their door was closed, though it was difficult to tell for sure.
After ten or twenty minutes had passed, as coloring with his left hand never got any easier, he turned to tell Sarah that he was done. He was this close to speaking like a girl, as the daycare activity put him right back in that mindset even though he was in his own bedroom.
“Aww, you did such a good job!” she smiled. Getting up and coming over, she looked at the colored sheet more closely. “Oh. You didn’t sign it, silly! How about purple? It’s one of your favorite colors!” And there wasn’t any pink in the box of crayons.
Writing was a lot different than coloring. With the latter, all Taylor had to do was slow down and stay in the lines. His handwriting was bad enough with his dominant hand, and he could tell by writing a single T that a proper signature wasn’t going to happen. Between the larger crayon letters and how he was stuck doing the task with his left hand, it looked like a child had written ‘TAY.’ A male child, at least, as there was nothing stereotypically feminine about the letters.
“Hmm, you can sign it as ‘Taylor,’” Sarah said, easily able to figure out why he had hesitated.
He finished up the task at hand, slightly worried that Sarah was going to tell him to hang it up on the fridge or something. The conversation with Anna had been embarrassing enough; he didn’t need her asking why he was coloring and felt the need to sign in such an immature manner.
For the time being, he was apparently going to be kept in the dark regarding her intentions. She picked up the drawing and tucked it into her binder’s front pocket. “You should probably work on your homework before it gets too late! Where’s your backpack?”
Hidden. Not very well. Taylor had just wanted everything out of sight when he hastily removed the girly outfit and accessories after managing to safely make it to his room. “In the closet,” he said. As soon as he had changed into his clothes from school, he had thrown the dress into the laundry hamper and dropped the backpack in the same corner.
“Got it!” Sarah exclaimed a few seconds later. Unlike Taylor, she didn’t seem remotely concerned with the open bedroom door. Placing Anna’s old backpack down on the bed, she pulled out the pink binder he had been given at daycare. “Do you remember where you left off?”
“Math,” he said. Because numbers were a little easier to manage with his left hand, compared to how he would have written out answers for the other subjects.
“Here you go,” Sarah said. Rather than letting him find the page himself, she opened the binder and flipped to the worksheet before placing it down in front of him, “These all need to be done before school tomorrow morning. And then there’s your video assignment. Oh, and I still have to teach you how to braid hair!”
That was SO much. The My Little Pony episodes alone were going to take an hour. The homework was easy enough, even for a jock with iffy grades, but working on it with the wrong hand was going to make it take longer. And he was nervous enough about the pink binder and Anna’s backpack, both of which could easily be seen by anyone who stopped to glance in on their way past his room. It was bound to happen eventually, if only so his sister’s friends could check out his ‘girlfriend.’
Once again, they settled into silence for a little while. Sarah was working on her actual homework, which Taylor wouldn’t have the option to do at all. Not when his normal backpack was still stuffed in his locker back at school. It wouldn’t be the first time he did an assignment at the last minute for one or more of his classes, though he normally pulled that off by not paying attention during a lesson; if he was busy writing love letters and sending panty pics to Sarah, there wouldn’t be much time to focus on his work.
Eventually, Sarah decided that it was time to go see Anna’s room and whatever that entailed. “Let’s go see your sister, Tay-Tay! Honestly, I’m surprised she hasn’t checked in on you yet.”
So much for waiting until Anna’s friends were gone. And Taylor still didn’t know what to make of the whole ‘Anna is in charge’ concept. Just another thing that Sarah surprised him with, and Anna jumped on it the same way she did when he needed a ride. Though they weren’t that close as siblings, Anna was always happy to tease Taylor when the opportunity presented itself to her.
It didn’t matter whether it was from class to class at school or a twenty second walk down the hall to Anna’s bedroom. Sarah took Taylor’s hand and led him in a way that was simultaneously like they were boyfriend/girlfriend and like he was a daycare girl who couldn’t be trusted alone.
“Who is it?” Anna called through the door after Sarah knocked.
“Sarah and Tay-Tay!” Sarah replied.
Taylor could easily hear the giggling from the other side. A moment later, Anna opened the door for them and said, “Come on in.”
Anna’s bedroom was the same pink as it had been for years. It was just one of those backburner projects, when something like a renovation or a remodel took priority over painting a room. Their parents had given Anna permission to tackle the project herself, though it was getting to the point where it was too much work to drag all her stuff to the middle of the room and paint when she’d be leaving for college in a couple years.
After briefly explaining as much to Sarah, Anna also introduced the two girls she was hanging out with. With Taylor and Sarah standing there hand in hand, the nerdy girl standing way taller than her ‘boyfriend,’ Anna’s friends looked just as intrigued as she had been earlier. Taylor’s first official relationship was with a girl who wasn’t annoyingly popular? It was certainly an interesting pairing.
Taylor was anticipating the thing about doing Anna’s chores, which was going to be worse with an audience. What he didn’t expect was Sarah running with what she had just heard about the bedroom.
“Ooh, you know what you should do?” Sarah said, giving Taylor’s hand a squeeze, “Why don’t you swap bedrooms with Taylor? He wouldn’t mind! Plus you’re in charge when it’s just the two of you. And shouldn’t the bigger, more mature sibling get the bigger bedroom?” She gave Anna a friendly smile. “Tay-Tay and I have been working on being nice to people. What do you say, babe? Should Anna take your bedroom?”