Published: May 21st 2025, 2:52:34 am
The silver lining to being put to bed so early was that it caused Taylor to naturally wake up well before Anna did. Once he double checked that the lights were still out in the bedroom that had been his up until yesterday, Taylor padded back to Anna’s former room and finally got around to figuring out what to do with all the dresses Sarah had picked out for him from the storage boxes.
He settled on hanging them all up on the side of the closet that couldn’t be seen from the hallway door, since apparently he had to keep that wide open from now on, then draping one of his darker dress shirts over the pinks and purples. It didn’t totally hide them, as the skirt portions were still sticking out below, though he also planned on keeping the closet closed most of the time. The only way he’d get caught is if Anna went snooping, in which case she’d probably find her old dresses no matter where he stashed them in there.
Sarah had sent him another text at some point last night. Thanks to his early bedtime, the nerdy girl was now staying up later than he did. She ‘suggested’ he wear a pink dress after school, to match his panties. It was obvious that she was poking fun at the color of his room, since he hadn’t been told to wear this much pink at first. He also noticed that all of Sarah’s texts were teasing, playful, and/or flirty. On the surface, it seemed like she was just aiming to make him feel awkward about her being overly affectionate as his ‘girlfriend,’ though he suspected it was also to give her deniability if he decided to try and blame her for all of this. Now that Anna had taunted him about the kinky nonsense he wasn’t actually into, Taylor realized it could absolutely look like that based on Sarah’s texts. He was the weirdo who was into wearing girls’ clothes, and she was the girlfriend who humored his fetish.
After changing into a brighter pair of panties in the bathroom, doing the usual quadruple check to make sure absolutely nothing could be seen as he moved this way and that in the same jeans from yesterday, Taylor returned to his room to pack up for the day.
There was no getting away from the purple backpack. He didn’t have an old bag down in storage or anything, and there wasn’t much else that would hold the girly binder, the Mary Janes he’d be wearing later, and the dress of the day. Since Taylor would rather risk an embarrassing backpack than being seen with any of its contents, he decided to claim he lost a bet and hoped that he wouldn’t be pressed to elaborate too much. He was for sure going to have to deal with Anna seeing it and teasing him about it. The real question was whether or not he’d be able to make it to his locker without any of his friends seeing, or even some random student who would be inclined to take a picture of the popular baseball star walking around with something that drastically clashed with his usual alternative image.
It was still pretty early in the morning. Taylor was tempted to just leave and text Sarah to meet him somewhere else, but he knew full well that he was at the mercy of her whims. She might want to come inside and chat with Anna for a minute, or could simply insist that the pick-up spot is on the curb in front of the house. Until he heard what the plan was, he was going to have to wait around. Leaving the girly backpack near the front door, tucking it slightly out of sight in the corner, he poured himself a bowl of cereal and impatiently watched the clock.
“Morning, Tay-Tay!” Anna greeted him as she stepped into the kitchen, “How’d you sleep? Liking your new room?”
Normally, they barely spoke to each other before school. Neither sibling was a morning person, so they were both content getting ready for the day in silence, save for sometimes speaking up to figure out logistics about whatever needed to get done in their parents’ absence. That’s what Taylor was used to, which made Anna’s chipper attitude particularly grating on top of everything else he had to deal with.
His annoyed look was enough of an answer, apparently. “Cute,” Anna chuckled, “Well, I love mine. We should have switched forever ago, don’t you think?” Letting that tease linger for a moment, she went on, “No bowl of cereal for me? What a thoughtless little brother. Why don’t you pour me one now?”
“The box is right there,” he said, with a small eye roll. There was a fine line between letting Anna ‘supervise’ him, which Sarah had encouraged her to do, and letting her needlessly boss him around. Despite how he felt about her bratty attitude, however, he knew he had to be careful where that line was concerned.
“Rude,” Anna muttered. Still, she didn’t push the issue. Grabbing a bowl for herself, she waited until she was done pouring the milk and about to take a bite before casually saying, “Sarah will be here in ten minutes, by the way. She texted me.”
Taylor definitely didn’t expect that. “Umm, what?” he asked. His phone was right there on the table, and he definitely hadn’t received a text.
Noticing his little glance, Anna smiled and said, “Guess she knows who the more mature and responsible sibling is. She wants me to tie your shoes, help you put your backpack on, and put your hair up in a ponytail.”
“What? No!” Taylor snapped. All of that was terrible. He could put his own shoes on, he was still hoping to keep Anna from seeing how he was using her old backpack, and he absolutely could not go to school in a ponytail.
“What? Yes!” Anna replied, mocking his little outburst, “Don’t blame me. You and your girlfriend are the ones who are into this weird kink. But if she wants to do the whole Domme-y Mommy thing, I’m not going to stand in her way. Or maybe you’re the one who’s into that stuff. Either way, she says you’re my little brother and that I’m in charge.”
Taylor cringed at the awkward term that echoed what Anna had suggested the previous evening. It wasn’t like that at ALL. Sarah was a nerdy bitch who had an ever growing pile of leverage on him; aside from ‘affectionate’ cheek kisses and patronizing hand holding, there was nothing physical about their fake relationship. This wasn’t some fetish or roleplay; it was Sarah gradually pushing his daycare self into his real life, while he tried to minimize the damage along the way.
After another bite of cereal, and a failure on Taylor’s part to come up with anything to say against such an overt tease, Anna said, “Well? Are you going to do what your girlfriend says? Or should we explain to her that you were a bratty little brother first thing in the morning?”
“Fine,” Taylor muttered. It was just like the early bedtime. While he could deny Anna when it was just Anna, like he did with her request for cereal, there wasn’t much he could do when she invoked Sarah’s name. He could suffer through getting his shoes tied like he was a child, and Anna’s laughter and/of confusion regarding the purple backpack; the main concern was the ponytail, which he was going to have to have a conversation with Sarah about. He absolutely was not going to go to school like that.
As soon as she was done with the simple breakfast, Anna practically skipped towards the front door, calling over her shoulder for Taylor to follow. While the girly backpack was tucked away, it wasn’t fully hidden. “What’s this?” she asked, picking up her old bag. She clearly recognized it, and only needed a second or two in order to process why it was by the front door. “Ooh, is Sarah making you wear this to school?”
“No,” he said, unable to keep from flushing slightly. It didn’t matter that he had anticipated Anna catching him with the backpack, even before the things Sarah texted her about. Either way, her older brother was wearing her early middle school backpack. “I lost a bet.”
“Hmm, with Sarah?” Anna asked, “Or your boyfriends?”
How much had she and Sarah been messaging each other? That was how Sarah referred to his teammates, as a way to further tease him about being a ‘girl’ after school. Regardless of context, everyone knew that only girls referred to their friends as girlfriends; it didn’t work with the opposite gender. “It doesn’t matter,” Taylor said, not dignifying her teasing with a real response.
“Hmm, you really should have asked,” Anna said, “Next time you want to borrow my stuff, make sure you double check with me. I’ll give you a pass this time, only because I really want to see you wearing this out the door.”
It didn’t sound like she knew the extent to which he had ‘borrowed’ from the boxes downstairs. And Sarah would only be sharing so much, when the only reason Taylor was still going to daycare and letting her embarrass him at school and at home was because she was keeping the majority of the ‘Tay-Tay’ stuff to herself. “Whatever. I’m going to wait at the curb,” he said.
Anna tilted her head. “Aren’t you forgetting something?” Shoes. Backpack. Hair. She started with the backpack, since it was already in her hands, making Taylor turn around so she could help him slip his arms into it from behind. It was all kinds of demeaning, considering his age. Then she knelt down and decided that just tying his shoes wasn’t enough. Instead of letting him put them on himself, she took his foot and roughly worked it into the first sneaker without bothering to loosen the laces at all.
Nearly tripping from the jerky motions while he was only standing on one foot, Taylor snapped out a stern, “Careful!” If he was at school, with his teammates to back him up, it might have been intimidating. But even before all this Tay-Tay nonsense, Anna was immune to his bullying ways.
She just giggled. “You be careful, Tay-Tay. Okay, other foot.” Ever since hearing the awful nickname, she had been using it as often as possible. Once she was done putting his shoes on and taking care of the laces, she then snapped the hair tie on her wrist against her own skin for dramatic effect. “Now your hair. You want it up in a ponytail, right?”
Taylor just gave her an annoyed look. ‘Get on with it,’ essentially. While he’d let Sarah put words in his mouth and make him talk like a little girl, he wasn’t going to give Anna the satisfaction of affirming that he wanted his hair in a feminine style. At least it would be simple enough to undo it before getting out of the car.
In response, Anna sighed and rolled her eyes. Not pushing her luck for now, she decided to subtly punish her brother’s immature attitude by doing something a bit more fun with his hair. Guessing that he wouldn’t be able to tell the difference, when he always wore it down, Anna collected his dark locks and went for a high ponytail instead of the normal variety. “There,” she said. Stepping back and dusting off her hands, she gestured towards the window. “Perfect timing, too. Your girlfriend is here.”
Feeling absolutely ridiculous as he stepped outside with Anna in tow, even more so when he felt the swish of the ponytail with every step on the way to the car, Taylor hesitated as he approached the curb when he remembered that he’d be sitting in the back. On a booster seat. His sister already had so much to tease him about, and that would absolutely feed into the misconceptions she had about his dynamic with Sarah.
“Morning, babe!” Sarah greeted him through the rolled down passenger window, “Cute hair. Trying something new today?”
Of course she was being coy about why he was really wearing his hair up. “Morning,” he reluctantly said, before turning to Anna, “Believe it or not, I can get to the car myself.”
“Sure about that?” she smirked, “By the way, Sarah only texted me that she was on the way. I made the rest up.”
Taylor froze. She was lying, right? If he just went through all of that for nothing . . .
“Hey, Anna!” Sarah called to his sister. She seemed oblivious to whatever was going on between them. “Do you need a ride, too? I’m happy to take you!”
“Hmm, maybe another time,” Anna said, “My friends are picking me up today, though it might be fun to go with you and Tay-Tay one of these days. His hair was my idea, by the way.”
Sarah smiled. “I was assuming. Have you seen Tay-Tay in pigtails? He lets me braid his hair sometimes for practice. I love trying out different ribbons and bows!”
Ignoring Anna’s enthusiastic question about whether or not Sarah had pictures, Taylor hastily moved to the car and opened the passenger door, hoping Sarah would make an exception with his sister there.
Not so much. “What are you doing, Tay-Tay?” she asked, “You’re not legally tall enough to sit up front, remember? Back seat, babe. I don’t want to get my first ticket because of you.”
Taylor grimaced. There was no way Anna was going inside and missing this; now that she knew he had to sit in the back when Sarah drove, he would almost certainly get caught using the booster seat.
And Sarah wasn’t about to do him any favors, since something like that was simple enough to reveal without giving away the ‘little girl’ stuff. “Get in, babe! Mind getting the door for him, Anna?”
“Not at all,” Anna said. She didn’t know what was coming, but assumed it would be fun due to how Sarah was including her in general. Stepping forward and gripping the car door before Taylor could do the same, she opened it and proceeded to burst into laughter upon seeing what he was going to be sitting in. “Oh, my God!” she exclaimed, “Taylor- sorry, Tay-Tay sits in a car seat when you drive him??”
“That’s the law!” Sarah said, “It’s a booster seat, actually. But yeah. He should actually be in one of those whenever he’s in any car.”
Taylor desperately looked back and forth between Sarah and Anna, knowing how bad this was. Anna was absolutely going to be sharing this with her friends the second she was picked up. And, if he ever needed to hitch a ride with her again, there was a good chance she and/or the others would insist on a similar seat for him.
Doing his best to keep a straight face, as if it would do him any good at this point, Taylor pushed forward and begrudgingly got in the booster seat and immediately closed the door behind him before buckling in.
“Don’t be rude, babe,” Sarah said, “Aren’t you going to say goodbye to your older sister, and wish her a good day?” Further prompting him to do so, she pressed the button on her door the rolled down his own window. As in, they weren’t leaving until he played along.
“Bye, Anna.” He said it so coldly, glowering at her with crimson cheeks as he utterly failed at being the mean older brother. That only worked when he was taller than her, and when they were both a little younger. “Have a good day.”
“Bye, Tay-Tay!” Countering his pouty attitude by acting overly peppy and giving him a teasing wave for good measure, Anna made sure to not leave Sarah out. “Bye, Sarah! Take care of my little brother, okay? Have SO much fun at school.”
Sarah returned the energetic parting with a smile of her own before pulling out and rolling up the windows. Once it was just the two of them, she met his eyes in the rearview mirror, partially for the sake of checking out his high pony again. “You let Anna do your hair? Should I be jealous?”
Of his sister? Not even a little bit. And unless Sarah was pretending to be clueless, Anna hadn’t been lying about how she never got a text from Sarah beyond the pick-up time. “She said you texted her,” Taylor said.
“I did text her,” Sarah said, “And where’s that cute girl voice, Tay-Tay-? You’re supposed to be working on that, remember? We both know you’re a little girl at heart.”
Uh huh. Something like that. Taylor cleared his throat, forcing the higher tone he hadn’t used since they were last in her car. “You didn’t text her about my hair?”
Sarah didn’t reply right away. Then she scoffed. “Oh, I see. Anna said I wanted you in a ponytail. And you believed her. Cute!” Glancing at him in the mirror again, she went, “Tell you what. Keep it like that for the drive, for being a gullible little girl and falling for your big sister’s tricks. And I can quiz while you keep working on that voice. Last night was episode four, five, and six, yes?”
Yes. As they headed towards the school, Taylor summarized the plot of the episodes he watched, and answered all the questions Sarah asked about the details. Was she also wasting an hour on the show, or just looking up what happened to know enough to check that Taylor was keeping up? Either way, he couldn’t risk taking the easy way out like that.
As Sarah pulled into the parking lot, she said, “By the way, I was thinking . . . You probably need someone to drive you to your game on Saturday, right? And I bet you’d be a lot more comfortable wearing panties while you play.”