Lady Lucia
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From Taylor to Tay-Tay, Chapter Five
🕑 Added 2025-01-22 05:00:20 +0000 UTCTaylor had his phone now, which was one of the few improvements from the previous day. He dug it out from where he had stashed it in his backpack before daycare, planning on texting Anna to see if she was at the house. Before he could do so, Sarah plucked the device from his hand. “Taylor, this is just to be used for emergencies,” she said, “Is this an emergency?” She tucked the phone between her thighs for safekeeping while driving, correctly assuming that Taylor wouldn’t reach down there to get it back.
In the awkward girl voice, Taylor explained how he wanted to ask Anna where she was. Preferably before they made it to his house. Sarah just gave a dismissive wave of her hand and said that it would be fine. If Anna was there, Sarah would explain.
Explain how? No matter what she said, there was no getting away from the fact that he was dressed like a little girl. Whether Sarah told the truth, or lied and went with something like this being a dare or a lost bet, Taylor’s sister would never let him live this down. And if she took a picture, he was totally screwed. Sarah seemed to have some self control, as she was clearly enjoying watching him squirm by dangling so much humiliating leverage over his head, but Anna was more of a wild card. He would either be under double blackmail between the two girls, or Anna would text her friends immediately and the whole school would know about it within ten minutes.
Sarah seemed indifferent to his concern. It was kind of surprising, since Anna could potentially ruin all of Sarah’s fun. Taylor obviously wouldn’t be going to daycare any more if his sister wasn’t able to keep this to herself. Somewhat of a relieving thought, even if Taylor didn’t have the courage to rip off that bandaid himself and tell Sarah to fuck off.
Taylor’s heart was pounding as they pulled up to the curb. Was this really happening? There was a good chance Anna was up in her room like yesterday, though that didn’t do him any good if Sarah was coming in to do whatever. He didn’t actually know what her plans were beyond ‘escorting him inside.’
Yesterday, he had snuck in through the side door. With Sarah holding his hand and making all the decisions, however, he was walked right up to the front door. Further proving that she didn’t mind whether or not his sister was home, Sarah rang the doorbell.
If Taylor hadn’t been holding his nerdy classmate’s hand, he would have bolted right then and there. It’s what he started to do on instinct, until he felt her grip tighten in warning. Where would he run, anyway? The Mary Janes he was wearing somewhat offset his athletic abilities as well.
A long minute passed, during which Taylor was nervously fidgeting and expecting to hear Anna’s voice at any moment announce that she was coming. Or maybe she was ignoring the bell, since opening the door was becoming similar to picking up the phone when it was an unknown number. If Anna didn’t have a delivery on the way or a friend who was coming over, then she could have just shrugged and not gotten up at all.
“Well, maybe nobody’s home,” Sarah said, “Did your parents give you a key, little girl?”
That obviously wasn’t how he would put it, but yes. He took out his key ring, stepping forward to unlock the door out of habit, until Sarah took the keys from his hand as easily as she had taken his phone. She commented that he should really have something cuter, before deciding that she would just take care of it. After opening the door, she dropped the keys in her purse, where his phone had also been tucked away once Sarah had parked the car.
“Nice place. You and Anna get it all to yourself, right?” In response to the look of confusion on Taylor’s face, Sarah explained how she knew that their parents were never around. “I’m in half your big girl classes, Taylor. You do realize everyone hears you and your loud friends when you brag about whatever, right? That’s why I made Anna your emergency contact for daycare.”
Uh huh. It was such a transparent lie; Taylor knew full well that it was really just another way to keep him in line.
After taking a quick look into the kitchen and living room, Sarah said that she wanted to see Taylor’s bedroom. She guessed correctly that it was on the second floor, leading him up the stairs before asking him which one was his. Anna’s door was closed, which could mean anything. Taylor led Sarah to his room, hoping that the combination of his sister not coming to the door and the quiet of the house aside from Sarah’s voice meant that he was in the clear.
“Wow. We have a lot of work to do,” Sarah said, upon a single glance, “Can I see your panty drawer?”
He quietly told her he just had the one pair, feeling a lot more self conscious about speaking in the higher pitch now that he was in his own bedroom. And since he had stupidly been under the impression that Sarah wouldn’t push for more beyond a second daycare appearance, Taylor had only taken the bare minimum from the boxes of Anna’s old clothes.
“Taylor, you’re a little girl,” she insisted, “You really need clothes that are appropriate for your age and gender. Why don’t you show me where you found that pretty dress?”
Reluctant as he was to leave the privacy of his room now that they had made it there, Taylor also knew that Sarah probably wasn’t going to leave until he went along with whatever she wanted. So he walked her down to the basement, still nervous about Anna catching him; though it felt like she wasn’t currently home, she could easily show up at any minute.
He also felt awkward about being dolled up in his own house. It was one thing at daycare, when he could somewhat disassociate due to it being so different from his teenage life. Walking around in a dress and pigtails at home, however, was a different experience entirely.
Taylor brought Sarah to the well organized storage room in the basement, where he pulled out the boxes he had gone through the previous day. Before he could open them, or step aside to let Sarah look through everything, she told him to take it all up to his room.
She grabbed one of the boxes herself, leaving the other two for him to stack and carry himself. “You’re a big girl, right?” she teased, “I bet you can handle a couple boxes!”
Obviously, he could. Clothes weren’t that heavy. And yet, it was still a bit of an endeavor thanks to how maneuvering the armful of wide boxes up the stairs and around corners wasn’t quite as natural while he was still in the Mary Janes. Sarah ended up making it upstairs way before he did, where she proceeded to dump her box onto his bed to look through his sister’s old clothes more easily than if she had kept everything neatly folded in the plastic container.
“Oh, Taylor!” she gushed, holding up a light pink dress, “This is perfect for you. Wear it to daycare tomorrow?” It wasn’t actually a question.
While Sarah emptied the other two boxes onto the bed, creating an enormous pile of Anna’s old clothes, she gave Taylor an unexpected task. He was to go through his laundry hamper and sort everything. It didn’t make any sense, when all his clothes went to the same place to be washed, but it definitely wasn’t an argument worth having. Like before, he justified doing whatever Sarah said with the logic that he would be able to undo his feminine image as soon as she left. Until then, it was better to suck it up and entertain her power tripping whims.
A few minutes later, Taylor had completed the task. The hamper hadn’t been that full, so it hadn’t taken too long to separate his dirty clothes into piles of shirts, underwear, etc. Meanwhile, Sarah had made some progress with a similar endeavor. She had pulled out every dress that Anna used to wear, laying them on top of each other in two distinct piles. Taylor could already tell that the categories were something along the lines of ‘normal’ and ‘little girl.’
“Done already?” Sarah smiled, “What a good little girl! Okay, why don’t you take over for me? See what I did with the dresses? Do the same with your sister’s t-shirts and panties. One cute pile, one boring pile. Can you handle that?”
Taylor nodded, a faint flush creeping up. Technically, yes; he could manage something that simple. It didn’t mean he wanted to be going through the immature collection.
He could put two and two together in terms of how the ‘cute’ clothes were meant for him. At the same time, the bigger picture eluded him until Sarah started going through his clothes. She started by taking the dirty boxers he had sorted from the hamper, tossing all of them into one of the now empty boxes they had brought up to his room. Then she raided his underwear drawer, doing the same with every clean pair. When Sarah caught him looking at what she was doing, she reminded him that he had a job to do.
Once all his boxers had been thrown into the plastic storage container, Sarah shifted gears and grabbed all the childish dresses from his bed. She brought them over to his closet, where she hung them up one at a time. There were only so many free hangers; when she needed more, she took the ones that were being used for his dress shirts. One at a time, she dropped the dark button-downs onto the floor until every dress had a home. Then she added those to the same box holding his underwear.
It didn’t take long for Taylor to connect the dots about how Sarah was completely overhauling his collection of clothes. All of his t-shirts from the hamper and the drawers were dropped in the box next, and replaced with the youthful/girly ones he had sorted on the bed. And, once he was done going through Anna’s old underwear, Sarah added all the cartoon print ones to the underwear drawer she had emptied out.
She didn’t take all of his clothes, though the box was nearly full by the time she was finished swapping out his clothes with the more immature outfit pieces his sister used to wear.
“Okay!” she smiled, “I think that should do it. Here, you take the rest of Anna’s stuff back downstairs. I’m going to put your stuff in my car.”
“What?” he asked. This was all supposed to be some way to embarrass him, right? He didn’t actually expect her to remove the clothes from his room entirely. At the very most, he assumed she would make him bring it down to the basement as if he was putting his real clothes into storage for the extent of his time in daycare this week.
“In my car, Taylor,” she repeated, “I’m going to hold onto your silly boy clothes for now. You said you’re going to wear panties from now on, and I think it’s best if I take away any temptations to do otherwise. Don’t worry, I’ll keep everything nice and safe for you. Oh! I bet I missed something.” Sarah retrieved his backpack and opened it up, pulling out the outfit Taylor had worn to school prior to changing for daycare. “There. That should be the last of it.”
“But-” he started to argue. While he had technically agreed to wearing girls’ underwear 24/7, his interpretation was that he’d suffer through wearing them to school and being super careful about every move he made. Until now, he had planned on changing into boxers at home.
“Now you’re wearing panties through Saturday,” Sarah cut him off, “Remember that deal about not pouting?”
Yeah, but- That was just supposed to be for daycare! It was already a lot of work committing to the girl voice, and now she expected him to keep pretending like he was the immature tween that attended such a program? Of course, he also remembered all the leverage Sarah had on him, and what he had already put himself through to keep his reputation intact. So he forced a smile that looked both awkward and demure.
“Much better!” she said, “Okay, let’s meet back up here in a minute.” With that, she clicked the lid into place on top of the box of his clothes. Without waiting for him to follow suit with Anna’s old outfits that weren’t childish or girly enough, Sarah headed out into the hall.
Taylor reluctantly stacked the other two boxes like he had before and hauled them back to the basement. The moment he placed them on the shelf where they belonged, he darted back to his room. As usual, his main concern was his sister catching him like this. The rest would have to wait until he had more than a minute away from Sarah. Not that a whole evening yesterday had done him much good.
Sarah managed to beat him upstairs, where she was standing by his desk. He took a seat when she gestured for him to do so, unable to keep himself from fidgeting slightly with the skirt as it rode up slightly. Two days in dresses wasn’t nearly enough to get him used to having the loose fabric around his thighs.
She started by playing with his pigtails for a moment, teasing about how cute he looked when getting ready to do homework. Then she pulled out her phone and showed him that her blackmail folder had nearly doubled in content. Sarah had a handful of shots of him in the second dress, looking just as young and feminine as he had yesterday. She went on to play a video of him participating in Hopscotch, followed by him doing jump rope with the group of girls he had been for most of their time outside.
He distinctly remembered the feeling of both the skirt and his pigtails bouncing with his movements, though it was so much worse to watch it from an outside perspective. If he hadn’t known what he was looking at, the ‘girl’ in the video would look totally realistic. Unfortunately, that wasn’t enough for him to tell Sarah that no one would believe her; she had way too much on him at this point, and the pictures would be a lot easier for her to zoom in on and point out the similarities.
“So, there’s that,” Sarah said. She opened his laptop and told him to unlock it for her, clarifying that she didn’t really care about the password. Just for good measure, she turned away and went over towards his bed for a second as he typed in the simple combination of numbers. “Also, there’s this.” Holding up a bright purple backpack, she said, “I think this is much better than what you brought to daycare today. Do you like it?”
Obviously not. Except he knew what she was fishing for, and knew that he wasn’t supposed to pout. “Umm, yeah,” he said, in the higher pitch he had been stuck using for several hours now.
“Good! You can bring this to school tomorrow,” she casually asserted.
Just something else he had to worry about on top of wearing panties to class. Would Anna’s old backpack fit inside his own? That’s how he had stashed the clothes he had brought to change into at the end of the day. It wasn’t as if he could show up in the morning wearing his sister’s backpack, especially if he hitched a ride with her and her friends again.
Without giving him much time to think about the latest development, Sarah leaned forward and pulled up his browser to search for something. A few seconds later, she found what she was looking for. It was one of those websites with a bunch of shows and movies that someone out there had compiled for people to watch for free. Only this one seemed to be focused more on kids’ shows and movies.
“Here you go, missy,” Sarah said, as she clicked on the first season of My Little Pony, “Since you were running around in panties made for girls who love this show, I bet it would be fun to rewatch it from the beginning.” She scrolled down to the first link, starting the episode for a second only to pause it after making it full screen. “Why don’t you watch the first three episodes tonight?” she said, “And tomorrow, I’m going to quiz you to make sure that you did your cute assignment.”
That would take at least an hour. He had the time to do it, but that didn’t mean he wanted to waste it on some show that was for little girls. This was just another way of Sarah proving that she was in charge, and/or a way to mess with him from afar.
Flicking one of his pigtails, Sarah said, “I’ll leave you to it, Taylor! Remember, I’m your girlfriend now. You better act like it tomorrow morning, and you better be wearing panties.”
Fuck. He had completely forgotten about the ‘girlfriend’ thing. So much had happened since she decided that they should pretend to be dating for whatever reason.
Ignoring his blush and stupefied expression, Sarah exclaimed, “Later, babe!” She strutted out of the room, leaving the door wide open.
