Chapter Three

The pigtails had done a number of Taylor’s long hair, and he didn’t have running water to deal with the mess thanks to how the water was currently shut off for the ongoing renovations. All he could do was force a brush through his dark locks in an attempt to get them back to how they usually looked. It wasn’t actually that big of a deal, now that he was safe in the privacy of his room. He and Anna weren’t particularly close as siblings, and their parents being out of town so often meant that the only time he might be seen was when he went downstairs to figure out dinner. Besides, she had seen him with unkempt hair in the mornings; the only reason he was hesitant to run into her right now was the lingering nervousness from sneaking through the house, as well as the reason why he looked slightly different than he usually did after school. Anna probably wouldn’t be that perceptive, though she would also be more familiar with hair stylings than he was.

Taylor also had to make a trip down to the basement to look through the boxes of old clothes that their parents hadn’t donated or thrown away. Though he was specifically looking for Anna’s old dresses, as of course his younger sister was taller than him at this point, that search was one thing he wasn’t worried about. If Anna decided to come down to the basement herself for whatever reason, Taylor would hear the door open and have plenty of time to stash her stuff away and pretend he was there for something else.

The part that made him embarrassed was that he had to find an outfit Sarah would approve of, panties included. There were a lot of pinks and purples, many of them with girly scripts, flowers, or other immature designs. He eventually found a simple dress that was solid purple, which would have to do. As for underwear, he settled on a white/pink pair of BARBIE panties. That was close enough to what he had been caught in that afternoon.

Since all of his stuff was back at the school, there were a few other complications. He couldn’t work on homework, not that he took school that seriously when baseball was a better use of his time. Taylor also didn’t have his backpack, and needed a way to discreetly transport the girly outfit he was going to be changing into after his last class of the day. And then there was the matter of how he was going to get to school in the first place, as that would be quite the walk.

The backpack thing was the easiest fix. It was just a matter of looking through more boxes in the basement and finding one of his old bags. His tastes for darker colors hadn’t changed much since his early teenage years, so the alternative backpack wasn’t the worst. Once that was sorted, he just had to ask Anna to ask one of her friends if he could ride with them tomorrow. A senior guy, being driven to school with a bunch of sophomores. Sarah and her friends were popular enough, which helped, but still.

He just had to explain why he couldn’t drive himself. Waiting until the next morning wasn’t a good idea, either. There was a chance all of the seats were already taken, in which case he’d have to figure something else out. Taking the bus had crossed his mind, except he had no idea what the schedule was or where the closest stop to their house was. So he reluctantly knocked on Anna’s door, ultimately giving up on his earlier plan to avoid her for the whole night.

Anna didn’t comment on his hair, nor did she seem to notice or care. However, she was predictably difficult about his request. “I’m pretty sure the last time I asked you for a ride to my friend’s house, you laughed in my face. Why can’t you drive yourself, anyway?”

It was more of a scoff, but still. Going with the best lie he had come up with before approaching her, Taylor explained how he and his friends drove together to hang out after school, and swinging back to get his car was too much of a pain once there was traffic.

“Uh huh,” Anna said, crossing her arms, “I still don’t see how this is my problem.”

After a little more back and forth, Anna offered a compromise. She was enjoying the fact that her older brother was relying on her for something, but also wanted to be careful that she wouldn’t get in trouble for being the reason he didn’t make it to school. And, unlike him, she wasn’t a brat who enjoyed picking on easy targets. “I’ll see what I can do,” she said, “But you’re going to give me $20 for gas, and treat all of us to coffee on the way. Deal?”

He reluctantly agreed. That was a good chunk of his monthly allowance, though he also had a credit card for emergencies, baseball expenses, etc.

The following morning, Taylor stuffed everything he needed into his old backpack. Dress, panties, Mary Janes, and the hair ties for the pigtails he’d be in later. He knew no one would be going through the bag, yet he still felt the need to cover up the girly clothes with one of his baseball uniforms. That, and he was still holding onto the slim hope that Sarah would let him off the hook and he’d be able to go to practice like he was supposed to.

When Anna’s friend arrived to pick them up, she made it clear right away that she wasn’t impressed that their school’s star pitcher was getting into her car. To her, Taylor was simply Anna’s obnoxious older brother. “My car, my rules,” she said, as the two siblings got into the back of her hand-me-down sedan, “No talking unless one of us asks you something, or I’ll pull over and let you out. Cash for coffee and gas?” She held out her hand expectantly.

He couldn’t believe a sophomore was talking to him like that. And that she was getting away with it. Her little power trip did make a little bit of sense, as she wasn’t someone Taylor could target later for revenge. Between her confidence and the fact that she was one of Anna’s friends, she knew how much she could get away with while Taylor was relying on her for a ride.

“My wallet is at school,” Taylor admitted.

“Anna?” she asked.

“I’ll pay for now,” Anna shrugged, “Taylor will pay me back later, plus interest. As long as he admits that sophomores girls are better than senior boys.”

Suddenly, all three girls were staring at him. Feeling put on the spot, though alert enough to make sure none of them had their phones recording him, he begrudgingly muttered the phrase. Repeating it word for word in a flat tone made it so it was obvious that he didn’t mean it, though the girls still giggled in amusement.

Once they were done having fun taking advantage of the rare situation where Anna’s older brother needed something from them, everyone basically pretended like he didn’t exist. Taylor didn’t mind being ignored, though having his phone would have been a nice distraction from the giggles and all the girly conversations he didn’t care about. All three girls ordered large specialty drinks, splurging more than they normally would since Anna would be fully reimbursed later. Then they headed to the school, where Anna’s friend pulled over half a block from the parking lot.

“You can get out here, Taylor!” she said, “Do you need a ride after school?”

No, he didn’t. As for being dropped off in a less convenient spot, that was fine. He didn’t need to be seen carpooling with them, just like they didn’t want to be seen doing a favor for some jock.

As Taylor crossed the nearby intersection and made his way towards the school, he slowed down to check on his own car . . . It was nowhere to be seen. Had it been towed? Maybe. That, or he was mis-remembering where he had parked it the previous day, and just couldn’t spot it amidst all the other vehicles. Students didn’t get reserved spots, so it was always first come/first served each morning.

He didn’t have time to investigate, as the warning bell meant that he only had five minutes to swing by his locker and get to his first class. Thanks to the mortifying events of the previous day, as well as how Sarah took him directly home after daycare, Taylor hadn’t done any schoolwork. That wasn’t completely out of character for him, since he and his friends would often hang out after baseball practice and shirk all of their responsibilities. Still, he usually found time to at least do the bare minimum, like burning through a simple assignment at breakfast or cramming for an upcoming quiz.

The school day was normal enough; once he was sitting with his teammates in first period, Taylor gradually settled into the familiar routine. Talking about the upcoming game, picking on a couple of the usual targets, and generally being immature boys between classes and at lunch. He didn’t say anything about how he was going to have to miss practice later; his excuse was pretty weak, and he didn’t want someone to mention it to their coach before the end of the day. Instead, he waited until the end of PE before turning to one of the guys and lying about how his parents screwed up and scheduled an appointment for him on the wrong day.

Naturally, they told him to blow it off and come to practice instead. If something like that actually did happen, that’s exactly what Taylor would do. But since he needed to satisfy Sarah’s conditions, he just came up with some bullshit about how it was important and that rescheduling stuff like that was a total chore thanks to how his parents were out of town so often.

Learning his lesson from before, Taylor didn’t shower right away. His friends hadn’t shared any knowing glances or said anything about the prank, which made him think it was some random classmate who thought it would be funny. Either way, he waited until the area was mostly cleared out and, this time around, had a spare set of clothes secured in his locker as an extra precaution.

He also wasn’t going to put on panties and a dress in the boys’ locker room. After drying off, he grabbed his stuff and made his way to the bathrooms just around the corner from where the daycare room was. Bracing himself for the awkwardness, he called into the girls’ bathroom, “Anyone still in here?” If there was, he planned on darting into the other bathroom and letting the person(s) think it was a janitor checking.

Luckily for Taylor, it was empty. He tentatively stepped into the opposite gender’s restroom, quickly scanning the stalls to make sure some shy girl had failed to speak up or whatever. Once he was sure it was clear, he darted into the far stall and hung his backpack on the hook before stripping down.

He still couldn’t believe he was doing this. Putting on an old pair of his sister’s panties, followed by a childish dress. And, finally, swapping out his shoes for the Mary Janes he had been given yesterday. It wasn’t too late. He could still change into his baseball gear and go to practice, and tell his teammates that he decided to skip his fake appointment. Sarah’s leverage on him was too damning, however, and degrading himself for the second day in a row was the only way to make sure no one else saw it.

The ‘girl’ in the mirror was an embarrassing sight. Taylor knew he was a guy, which meant he could see that it was a short male in a dress looking back at him. But he could also see how Ms. Hamilton and the others so easily believed he was a younger girl. Between his height, his long hair, and his barely existent body hair, the dress that he was wearing easily sealed the deal in terms of making him look like a girl who belonged in daycare.

Doing his best to will the blush away, he slung his backpack over his shoulder and left the girls’ bathroom. At least he had his stuff this time. Life after daycare would be a lot easier now, even if it made him a little nervous to have identification and high school assignments stashed in his bag. But Ms. Hamilton had no reason to go through his things; as long as Taylor didn’t take out his actual assignments, like some of the other girls did, he’d be fine.

He hesitantly turned the corner, walking towards the classroom of girls and bracing himself for another afternoon of daycare. Right away, he thought Ms. Hamilton was going to figure out that he didn’t actually belong there and start asking questions. To his surprise, she simply greeted him with a smile and checked his name on the sign-in sheet. As in, there was a name to check off.

Before he could dwell on that, Sarah was sauntering over. “Taylor!” she exclaimed, “So good to see you again.” Her smile wasn’t quite as friendly. “Come on, I can do your hair.” With that, she took his hand and walked him to a desk near the opposite corner of the room. At this point, only around half of the girls had arrived, giving them plenty of time to get sorted. “You should really learn how to do this yourself, by the way. Pigtails are perfect for a little girl like you. Maybe your older sister can teach you?”

Taylor simply sat there and allowed the nerdy girl to braid his hair. From here on out, any talking he did would have to be in a feminine tone, so he only planned on talking unless absolutely necessary. As badly as he wanted to ask about how his name had been added to the list, or say something about how he was not a little girl, he opted to stay quiet.

Of course, Sarah wasn’t going to make it that easy. “You’re wearing panties, right?” With how she was positioned behind him during the braiding process, she could speak close to his ear and keep anyone else from overhearing their conversation.

Grateful that he was facing away from the girl, Taylor blushed and gave a small nod.

“Good,” she giggled, “Where did you get them? You better not be wearing the same pair as yesterday.”

Taylor tensed up. Would Sarah know if he was lying? She gave him a ride home, and there wasn’t a store that was particularly close to his house. There was a good chance she already had an idea of how he acquired panties between then and now. Clearing his throat, doing his best to recreate the girly voice from yesterday, he meekly said, “My sister . . . ”

“Wow, really?” Sarah asked, “What did Anna say when you asked to borrow her panties?”

It- It wasn’t like that! “Umm, she didn’t,” Taylor muttered. He gave a brief yet awkward explanation as to how he found some of her old clothes.

Sarah just smirked, reveling in how the tables were totally turned on the jock that usually bullied her and so many others. “You’re such a freak, Taylor. Going through your sister’s underwear. Dressing up like a little girl. Did you wear Anna’s panties all day?”

Taylor merely shook his head. No, he just changed into all of this. As for the rest, he was in no position to defend himself. It did sound bad out of context, even though they both knew he was only doing this because he had to. Regardless, it would be better if Sarah stopped referencing his sister, who had nothing to do with this.

“Huh. That’s no fun,” Sarah replied, “From now on, I want you in panties 24/7. You clearly like wearing them, and it will remind you that you secretly wish you were a girl despite how you pretend otherwise at school.”

“No, you said-” Taylor started, cutting himself off as he tried to remember what exactly Sarah had said. The whole thing was kind of a humiliating blur, outside of her insistence that he show up again to daycare. Still, the point was that he was only supposed to deal with this for another afternoon.

“I said you needed to decide,” Sarah giggled again, giving his completed pigtail a flick, “You chose daycare. Besides, I already went through the trouble of getting you registered. If you don’t show up, Ms. Hamilton is going to call your sister to verify that you’re not coming. We can re-negotiate some of this stuff after daycare on Friday, okay? Until then, you’re only allowed to wear panties.”

Until Friday?! He couldn’t skip that many practices! Not to mention the rest of it. That his name was on the list because Sarah had registered him, the implication that Anna’s number was used for contact information, and the suggestion that he should wear panties to class. “Sarah-”

“Shush, Tay-Tay.” As she finished up the second braid, she gripped both of them and gave a rough tug. “You think picking on girls is funny? Now you can see what it’s like to be a girl who gets pushed around.”

“But-” he started to protest.

“I said shush,” Sarah murmured, with another sharp tug, “It’s up to you, girl. We could make it two weeks of daycare. Or you can agree that you deserve to wear panties through Friday. Which would you prefer?”

-------------------------
Check out my website: www.ladyluciastories.com

And read more of "From Taylor to Tay-Tay" (10+ chapters) and other exclusive stories on my SubscribeStar: https://subscribestar.adult/lady-lucia