Published: March 23rd 2025, 2:24:10 am
This was the second day in a row Taylor would be skipping baseball practice. Yesterday, he had been able to get away with not saying anything to anyone; when his teammates asked earlier, he blamed it on some bullshit his parents had pulled with a poorly scheduled appointment. This time around, he had to deal with one of the guys calling him out for it ahead of time.
“Hey, Tay-Tay? You’ll be at practice, right? Or do you have some studying to do with your girlfriend?”
It was exactly what he had been worried about. While Taylor could easily intimidate the rest of the school, the other baseball players were more or less on his level when it came to social status and jock energy. All it had taken was a single school day for him to be a bit of a target for teasing. Between ‘Tay-Tay,’ a nerdy girlfriend, and a missed practice, he was no longer the untouchable star player he had been a couple days ago.
“Fuck you,” Taylor snapped, throwing in a middle finger for good measure. He knew he had to be careful where the immature nickname was concerned. Protesting it too much would only encourage the guys to lean into it harder, “I’m only with Sarah because girls like her try harder in the bedroom.” It was the excuse that had finally come to him between lunch and P.E., as that simultaneously sounded more like he was using her and that their relationship wasn’t as serious or lovey-dovey as Sarah believed it to be.
“Ooh, is she a total freak?” one of the other guys asked, “I guess it’s always the quiet girls.”
Something like that. Sarah wasn’t actually that quiet, not that the popular guys would know from their limited interactions of bullying over the years. But all this little girl nonsense? Maybe ‘freak’ wasn’t quite the right word, though she had taken things pretty far already with the leverage Taylor still hadn’t figured out how to deal with. He was literally wearing panties underneath his gym shorts, and had been hypervigilant over the last hour on the 1% chance that someone decided to pants him for the first time ever. Though he was still a popular jock, the fact that he was being teased at all put him in new territory; between that and the humiliating underwear, he was constantly on edge.
Since it was the locker room, however, Taylor chose to hold back in regards to the curious responses. “I’ll tell you later,” he said. As far as he could tell, there weren’t any other classmates around who were listening in; they also weren’t being that quiet, and he had already risked someone changing in the adjacent section overhearing the conversation so far. His teammates were bound to gossip amongst themselves, but he would rather avoid some random guy talking about this in a way where it would get back to Sarah. Saying less was also a good way to keep his friends interested in his narrative, rather than their own amused speculations as to why he was dating a girl who was out of his league.
He was also avoiding the question about practice, not that Steven had been asking it for real. As soon as he could slip away, Taylor was going to grab Anna’s old purple backpack and change into the light pink dress Sarah had picked out for him yesterday. Another afternoon of daycare, and a second practice he was bailing on. At least his parents weren’t going to be getting a call or anything like that. They were out of town so often, plus Taylor’s coach was the type who preferred to communicate with his players directly when possible. Basically the teaching style where he treated them like adults, particularly the juniors and seniors who were old enough to be responsible for themselves.
Normally Taylor and his teammates would head out to the field together after class, usually in their gym clothes since they were just going to end up sweating in them again. Using Sarah as an excuse, since she was the reason he needed to be elsewhere, Taylor said he’d catch up with them later. So far, he had managed to come up with excuses for everything, though he had yet to think of something that would be important enough to make him miss a second practice in a row. At least he had until tomorrow for that, if he ignored the texts he would no doubt be getting that afternoon and evening.
He was a little worried about leaving his real backpack in his locker. If Sarah took him right home after daycare, he wouldn’t have a chance to grab it before heading out to the parking lot. Just in case, he transferred everything important to the purple bag, knowing that the real issue had nothing to do with his stuff; tomorrow, he’d have to find another way to hide the girly backpack, plus deal with shoving even more things into his locker.
Going to the usual girls bathroom in the isolated hallway, Taylor changed into the embarrassing dress and put on the Mary Janes from that first day Ms. Hamilton caught him in nothing but panties and assumed he was a girl. Shoving his sneakers and gym clothes into the backpack in their place, going through the process that was gradually going to become routine over the coming days, he headed towards the daycare classroom where Sarah would braid his hair like usual.
The nerdy girl looked as amused as ever when she saw him in the mismatched dress and backpack. At least he didn’t have to greet her in the cutesy way he had been doing up until now, sometimes in front of his friends. “Tay-Tay!” she exclaimed, “So nice to see you. Want me to do your hair?”
Not particularly. Though having his dark locks in pigtails would make blending in easier, when he was still a little worried about being discovered after multiple days of attending daycare. “Yes, Ms. Sarah,” he said, forcing a small smile.
“You should really learn how to do this yourself,” she said, as she began separating his hair into two halves, “How about I come over again and teach you? Maybe Anna can give you some pointers, too.” When Taylor shifted in discomfort at the suggestion, Sarah quietly chastised him and reminded him to hold still. “Well, I should meet your sister either way. So, you choose. Either we have her help with your pigtails, or you do all of her chores from now on.”
How would Sarah know about their chores? It took Taylor a moment to consider that she was probably just making an assumption; since he and his sister were home alone so often, of course they’d have some system of dividing what needed to get done. As for the choice, there was really only one answer; he wasn’t about to clue Anna into any of this ‘little girl’ stuff he was caught up in. “I’ll do her chores,” he mumbled, in the feminine voice that was only getting more natural to switch to after using it several days in a row.
“Fun!” Sarah exclaimed. As usual, her definition of that word was drastically different from Taylor’s. “You can introduce us tonight. Oh, one more thing. From now on, I want you to be left-handed at daycare. Think you can manage that?”
He had no idea. “Okay . . . ” he reluctantly said. Using his non-dominant hand for some things would probably be fine. There was really no way of knowing until he tried.
“Okay!” she echoed, staying enthusiastic despite the lack of Taylor’s energy, “If I catch you using your right hand, you’ll be in trouble.” Finishing up the second braid, Sarah rounded things out by giving him a patronizing pat on the head. “You’re all set, Tay-Tay. I should go check on the other girls, and see if Ms. Hamilton needs me. But first, what do you say when someone helps you?”
Lightly flushing, knowing exactly what he was fishing for, Taylor said, “Thank you, Ms. Sarah.”
It seemed like daycare pivoted between indoor and outdoor activities, not that three days was enough for Taylor to know whether or not the pattern he had picked up on was actually the case. He could have asked one of the other girls, but he was trying to avoid talking in the awkward voice as much as possible, not to mention how he only had to do this through the end of the week. One more practice to skip, and then not hanging out with his friends after school on Friday like he usually did.
Similar to his first day in the classroom, there were a few different stations for girls to choose from. Since Sarah hadn’t specified anything about Taylor’s participation, he chose the quietest table that was coloring in the corner. Working on a puzzle like last time would have been the most ideal activity with how he was now restricted to only using his left hand. As he grabbed a loose page with a handful of butterflies on it, then tentatively picked up a crayon with his non-dominant hand. While coloring would be easier than writing words, he could already tell that it was going to be a bit of a struggle.
Sarah was making the rounds, no doubt discreetly snapping a photo or two of him sitting in the new dress at some point. Three different instances of him fitting in perfectly with a group of daycare girls, and a blackmail folder that was growing with every passing day. Not that Taylor could do anything about it; the pictures from the first day were more than enough to keep him in line.
“Cute, Tay-Tay,” she commented on his coloring sheet, “I know it’s not a race, but you still have a lot to color!”
He had been going a lot slower than the other girls at the table, since each section took forever when making the effort to stay within the lines. It wouldn’t be the end of the world if he messed up, but he also didn’t want to give Sarah any openings to tease him. Apparently that was a losing battle, when she instead called him out on his pace.
Taylor was barely halfway done with his coloring when Ms. Hamilton announced that they were all going to play a game of Musical Chairs. Yet another activity Taylor hadn’t done in years, and something he was way too mature for. He couldn’t just sit out, either. It was a full group activity, plus he knew full well that Sarah would have a problem with him not even trying to include himself in something everyone else was doing.
Similar to Simon Says a couple days ago, he struck a balance of playing long enough to make it seem like he wasn’t losing on purpose, then eventually let someone beat him to the nearest chair once a number of other girls were already out. Taylor was really only competitive when it came to baseball, as well as other pick-up games he and his friends sometimes played in other settings. A childish game, in a setting where he really didn’t belong? He really didn’t care about being the winner.
After another full round of Musical Chairs, they moved on to Heads Up, Seven Up. Not nearly as active a game, though it meant Taylor eventually had all eyes on him as he stood up and made his guess in his girly voice. Thankfully, he was wrong, and could sit right back down. No matter what the activity, he always had to deal with the sensation of the dress shifting on his body, as well as the movements and the increasingly familiar weight of his pigtails when he did just about anything.
Near the end of daycare, Sarah surprised him with something else. “Want to work on some homework while I finish cleaning up?” she asked, placing a pink binder in front of him.
He had been coloring, since he couldn’t take out his high school work in front of the younger girls. But somehow, Sarah had acquired assignments that matched those around him, so he could both fit in and quietly feel embarrassed about how he was working on homework designed for a much younger student than he actually was.
It was slightly more mature than coloring, even if he didn’t love the color of the binder or how it would look in one of the pictures he constantly assumed Sarah was taking. At least he didn’t have to sit there for very long. Sarah had established herself as Taylor’s ride at this point, as Ms. Hamilton believed whatever the nerdy brunette had said about their families and how close they lived to each other.
Sure enough, Taylor wasn’t given the opportunity to return to his locker. Sarah held his hand all the way to her car, at which point she revealed yet another demeaning experience she had prepared for him. She had already demoted him to the back seat, since he wasn’t old enough to sit in the front. Now, there was a booster seat waiting for him. He had never seen something like it before; rather than a car seat, it was more like a padded version of what some kids were given to sit at the kitchen table.
“Don’t pout, Tay-Tay,” Sarah smiled, “Little girls your size aren’t allowed to be in the car without something like this. I don’t want to get in trouble! Go on, sit.” She patted the seat, then gestured for him to get in.
He was in no position to argue. Mortifying leverage aside, she was also his ride home. Reluctantly climbing into the car and sitting on the seat that he was wondering if she already had or if she specifically bought it to embarrass him, Taylor’s blush deepened as Sarah leaned forward to do the seat belt for him as well. He wasn’t attracted to her, and he was so frustrated about everything she was putting him through, yet it was still difficult to ignore a girl’s chest right in his face.
Still power tripping, Sarah took her sweet time as well. Fiddling with the buckle, she went so far as to push one of her breasts against him for a few seconds until she clicked the belt into place. “Got it!” she chirped, rubbing her chest against his face one last time before shifting back to meet his eyes with a smirk, “Good thing you like boys, right?”
Umm, what? He was a little bit flustered from all of that; it took him a second to register that she meant that he was currently supposed to be a little girl, statistically meaning that he liked the opposite gender. Sarah was only his girlfriend when they were at school.
Not pushing him for an answer, Sarah simply gave his cheek a peck and closed the door. As she pulled out of the parking lot, she finally got around to making sure Taylor did his not so academic assignment from the previous evening. “Pop quiz, Tay-Tay! Let’s make sure you know all about your favorite ponies.”
By the time they were pulling up to Taylor’s house, he had proven that he had watched the three episodes and knew way more about the animated show than the average jock his age would. All while sitting in a booster seat and talking like a girl.
This time, he knew for a fact that Anna was home. The car parked in the driveway was the same one he had been riding in for the last couple days on the way to school. As in, at least one of his sister’s friends was also inside, or possibly more.
“I need to change!” Taylor exclaimed, nearly slipping into his actual voice.
“Don’t be silly, Tay-Tay,” Sarah said, “You look super cute in that dress. Oh, right! That’s Anna’s dress, isn’t it?”
And her panties. And her backpack. Not that it mattered. Regardless of whose it was, he was mostly concerned with what he looked like and what would happen if Anna and her friend(s) saw him like that. Surely Sarah didn’t want that, either, when keeping this to herself was what gave her maximum leverage over him.
Meeting his eyes in the rearview mirror, Sarah said, “Hmm, how about this? I’ll go distract your dear sister, and you can sneak in through the back door. On one condition.” She paused for a second, keeping him in suspense while she offered an alternative to him stripping in the back seat of her car. “I’m going to give Anna another gift on top of you taking all of her chores. When I do, I want you to say ‘yes.’ Okay?”
A blank check? Taylor didn’t love the idea of that, even if Sarah could basically make him do whatever she wanted anyway, within reason. He also didn’t want to change with her present, which he was now thinking about, for the same reason that he avoided anyone at school seeing him in a state of undress. As much as he hated to admit it, he needed Sarah’s help.
How had he not put together Sarah wanting to meet Anna, and the fact that he was in a dress? Yesterday, that had been his main concern. Today, he had been dealing with a lot of unexpected curveballs that kept his mind off what would happen after school and daycare.
“Fine,” he muttered. Since he knew for a fact that Anna was home, he was a lot more nervous about everything than he had been the previous day. Including how even getting around the house would risk someone looking out the window at the wrong time.
“Relax, Tay-Tay,” Sarah giggled, “If you get caught, we’ll say it was a dare or something. Ready? Run, little girl!” Without any warning, she got out of the car and started walking towards the house, leaving him to scramble out of the booster seat and bolt out of view before she made it to the front door.