Published: February 19th 2025, 1:48:10 am
‘Write me a love note, and take a picture of it while showing off your panties. By the end of class, babe. Oh, and no leaving your desk!’
The follow-up text had been sent carefully, in a way that would temporarily leave Taylor in suspense while also making sure that no one else could see the second half of the message if they happened to catch a glimpse of his locked screen. Not that it mattered. The bright, immature artwork of the ponies he knew from last night’s episodes would be the first thing anyone noticed if they saw his phone; Sarah probably didn’t want him undoing the customization changes she had made, which meant he was going to have to be careful when using the device around his friends.
As for Sarah’s demand, both parts of it succeeded in making Taylor grimace; the thought of doing either of those things made him shift in discomfort. It wasn’t even about Sarah and his feelings (or lack thereof) towards her. She was attractive enough, in a nerdy way, but her social status alone was enough that he didn’t really think about her like that. Taylor was mostly concerned about his friends that he was sitting with in the back of the classroom, and how pretty much anything out of the ordinary that he did would potentially be noticed by one or more of them.
He looked towards Sarah in annoyance, though couldn’t see much besides the back of her head. She was in the front row, and probably only idly amused by the idea of his reaction to what she had left on his phone; ever the academic girl, she was already taking notes and focused on class now that it had started.
The one piece of good news was that Taylor’s logic in picking a low-risk pair of panties made the second part of Sarah’s ‘request’ feasible. If he was wearing pink or purple, it would be completely out of the question. Obviously, she wanted him to squirm, as she had made a point to imply that she wanted him to do this in class; if she hadn’t clarified about his desk, he might have thought of the same thing she already did about how taking a picture would be a lot easier if he did so in the bathroom or even the hallway.
As for the love note, he wasn’t sure what to do with that, either. The last time he had passed a note was in early middle school, and that had only ever been to his friends as a way to subtly communicate back before cell phones. Deciding not to overthink it, since the note would have to be on the shorter side if Sarah wanted a picture, he simply jotted down ‘Thinking of you’ on the corner of the page his notebook was open to. He reluctantly added a heart, hoping that would satisfy the unstated conditions of Sarah’s text while keeping things low effort on his end at the same time. Then, after making sure the guys next to him weren’t looking, he slowly and quietly ripped the brief message from the page.
Thankfully, this class was more lecture-based. Though Taylor and his friends were seated in the back like they were almost every period, they couldn’t really talk or goof off when the room was quiet other than their teacher talking about whatever slide he was currently on. Unlike Sarah, Taylor hadn’t been paying attention in the slightest. That wasn’t out of character for him, but it normally wasn’t because he was stuck entertaining some unpopular girl who had him under her thumb. Regardless, it would be much more difficult to deal with Sarah’s nonsense if Taylor and his friends could talk freely.
Nervously glancing left and right, verifying that Luke was still texting and Fletcher was working on some other class’s assignment that was probably due within the next couple hours, Taylor began fiddling with the hem of his t-shirt.
The neutral white tone against the darker fabric of his tee would still be obvious to anyone who looked over. And while ‘briefs’ were less embarrassing than panties by a long shot, every guy his age wore boxers at this point. At least, those on his team that he changed with regularly. Taylor also had to hold his phone with one hand, meaning the other hand had to both flash the waistband of his panties while simultaneously holding the scrap of paper in a way that the words could be read.
Positioning the paper, he discreetly slipped his fingertips underneath the waistband of his shorts and pulled the panties out just enough that Sarah would be able to tell that they were actually panties. Snapping a quick pic, he swiftly used his shirt to cover his sister’s underwear; it was faster and less noticeable to hide the waistband, rather than risking Fletcher noticing him tucking it back down.
Leaning back and letting out a heavy breath he hadn’t realized he was holding, Taylor opened up his photos and . . . Suddenly, he was holding his breath again. There were at least a dozen pictures of himself, dressed up like a little girl and participating in daycare activities across the two days he had attended. Sarah must have gone through all the shots she had taken and cherry picked the best ones to leave for him to stumble upon when he least expected it. Actually, it was more like she set it up so he’d see them sooner rather than later, if she assumed he would double check the photo she was making him take for her.
Bitch.
Taylor had already seen her collection of pictures/videos yesterday afternoon, when Sarah was strutting around his bedroom like she owned the place. This was just another reminder that she expected him to ‘behave,’ as now he had access to some of the crisp images of himself that he could absolutely not allow anyone but himself and Sarah to see.
It was a good thing he was already being cautious where his phone was concerned, too. Between the daycare photos and a separate but just as girly pony background on his home screen, he was going to have to use the device a lot less around his teammates until he was done with all this nonsense.
For the time being, he proceeded to tap the photo he had just taken; that was why he had opened the app to begin with. He had no idea what Sarah was expecting, as her text had been both teasing and vague. Hopefully this would be fine. The good news was, he doubted she was going to check it until the bell rang. Not when she was sitting in the front row, and too busy actually listening to their teacher and taking notes.
Taylor sent the embarrassing photo, then immediately locked his phone and slipped it into his jeans pocket. He’d have to kill time some other way. Unlike Fletcher, he didn’t have any assignments to tackle at the last second. Since there was nothing else to do without his phone, Taylor decided to use the time to brainstorm ways to deal with his situation with Sarah. Of course, he made no progress. If a whole evening at home wasn’t enough for him to think of a solution, he wasn’t going to suddenly come up with an idea in the middle of a history lecture at school.
At the end of class, Sarah surprised him by walking over to the back row and throwing her arms around him. Before, he only had to deal with a couple of his friends witnessing the false relationship. This time, at least half the classroom was there to see the nerdy girl being affectionate with the last person anyone would expect her to be with.
“Walk me to class?” she asked. Though she was speaking at a normal volume, it was as if she was shouting when there were so many eyes on them. “You can carry my books!” Sarah planted a kiss on his cheek, then strutted to her desk to grab her stack of binders and textbooks.
As she did, Taylor was mostly focused on keeping himself from glaring. Letting out a quiet sigh, he muttered to his friends, “Like I said, it’s a long story. I’ll explain later.” That was something else he had spent some time thinking about over the last thirty minutes or so. Whatever he told the guys have to be believable, yet not too mean. Anything that got back to Sarah wouldn’t be good for him.
“Sounds good, Tay-Tay,” Luke said, “Catch you later.”
“Shut the fuck up,” he muttered.
That was all the time he had before Sarah was coming back over. “Here you go!” she dropped her things on top of his small stack of books, smiling as she said, “You’re the best, babe. Ready to go?”
Not particularly. They didn’t even have class together next period. She was just having Taylor be a ‘good boyfriend’ by going out of his way to do this couple-y thing with her. Ignoring the looks he was getting from those who had stuck around when they were hit with this unexpected social development, Taylor followed her out of the classroom and towards the other side of the school.
As they walked, Sarah had a smug look on her face as Taylor carried the books he would normally knock out of her hands if given the opportunity. “By the way,” she said, when they were clear of anyone who would be listening in, “We’re going to keep this PG, like the cartoons you watch. You’re really not my type and I don’t want to actually kiss you. Besides, you’re too immature to be kissing anyone. But we can hold hands and kiss each other on the cheek!”
Good. Taylor didn’t want to kiss her on the lips, either. Or on the cheek for that matter, though it sounded like he was going to have to occasionally do that to keep up appearances. As for the rest, it didn’t make a lot of sense for Sarah to push this boyfriend/girlfriend thing when she wasn’t actually into him. He had too much on his mind to consider that this was the perfect combination of ‘good for her’ and ‘bad for him’ from a social standpoint.
“Cute pic, by the way,” she said, “Tomorrow, I want you in something bright pink. Okay?”
“Umm . . . ” he hesitated. That really went against his strategy of wearing the lowest risk options that she had left in his underwear drawer.
“Tay-Tay,” Sarah said, quietly and sternly. She nudged him towards the side of the hall, to a wall without any lockers on it so they could stand out of the way. Despite her tone, she maintained a soft smile in case anyone was watching. For an unpopular girl, she was surprisingly competent when it came to stuff like this. Maybe having leverage on someone like him was all it took to shift her awkward, downward glances into confident eye contact. That, or Sarah was just nervous when she was outnumbered by a small group of jocks who decided to pick on her. “Are you wearing your sister’s panties?”
His eyes widened at the mortifying question. It wasn’t the first time she had referenced the feminine underwear in such a way, though it was way different in public than when it had just been the two of them. For the first time in his high school career, it was Taylor’s turn to avert his gaze when someone confronted him. Part of it was to make sure no one had overheard Sarah, while the other part was that she was taller than him and unexpectedly intimidating despite the clothes and the glasses he normally made fun of.
“I asked you a question, babe,” she murmured, with a smug smile, “Are. You. Wearing-”
“Yes!” he hissed. Hearing it once was bad enough, and anyone he knew could be passing by in the crowded hallway.
“Mm hmm,” Sarah hummed, “Whine about your panties again, and we’re going to tell Anna all about what you’ve been wearing all year. Now, what are you going to wear tomorrow?”
That was so unfair. She was threatening to twist what had just been a humiliating 1-2 days into suggesting that he had secretly been wearing panties for months. Anna might believe it, too. That, or go along with it regardless of whether or not she bought whatever Sarah was saying. Taylor had already somewhat lost the upper hand of being the older sibling when his sister passed him in height, and he could only imagine how many chores and other tasks he’d be on the hook for if Anna dangled this over his head in a similar yet totally different way than how Sarah was power tripping.
“Pink panties,” he muttered. Sarah would probably just make him try again if he didn’t actually use the word. Sure enough, she made him clarify right away, and he begrudgingly said, “Bright pink panties.”
“What a good little girl,” Sarah giggled. She leaned in and gave his cheek a peck, then nudged him back in the direction they had been walking before, “Come on, babe. I don’t want to be late to class!”
Just like that, she was pretending that nothing had just happened. They were just boyfriend and girlfriend, walking down the hall together as if it was totally normal for the two of them to be dating.
When they arrived at her AP class, Sarah further flexed her control by smiling and saying, “Now, you should kiss me, boyfriend dearest. And whisper in my ear what you really are.”
It took Taylor a second to process what she meant like that. He hadn’t actually said the phrase out loud very often, though Sarah did make him say it in daycare yesterday by threatening to extend his time in panties and dresses.
Leaning up and brushing a kiss against her cheek, he remained on his toes for an extra second to reluctantly murmur, “I’m a little girl . . . ”
Quietly giggling, Sarah looked down into his eyes and said, “You’re so cute, Tay-Tay. Now, run along. I’ll see you at lunch; I can’t wait to get to know your friends! Maybe I’ll bring one or two of my own?”
Hoping she was just teasing about that, as he couldn’t imagine a meal with those two groups mixed, Taylor allowed himself to be dismissed in the patronizing way. After all that, he could use a breather from the nerdy girl.
Once Sarah took her things from his arms, Taylor headed back towards the other side of the school. As for his own class, he didn’t care if he was a minute or two late. It wouldn’t be the first time an athlete missed the bell for whatever reason.
Taylor was used to getting looks at school, just in a more positive light. Admiration and/or jealousy for being a star player on their school’s top team, interest from girls in his grade, and nervousness from the less popular crowd. When he got to his general pre-calculus class, however, he could feel that things had shifted. Word had clearly gotten around between first and second period, and everyone was clearly curious as to why Taylor had broken his single streak with Sarah of all people. It was too early for anyone to be judgmental about the whole thing, save for perhaps his teammates, though he still felt a bit awkward about the energy in the room as he took his seat. It didn’t help that he was the last one to arrive, meaning there was nothing casual about his walk from the door to his desk.
He half expected to receive another text from Sarah. If she gave him another ‘by the end of class’ task, it would be more difficult to see it through when this teacher usually gave them at least half the period to work through examples of whatever she had most recently gone through. There was only so much Taylor could do when he and his friends were free to hang out in the back corner and only do the bare minimum when it came to calculus formulas.
Thankfully, his phone didn’t buzz with any new notifications as the class settled into the formula their teacher was reviewing. Either Sarah was giving him a break, or her own phone was stashed away for class. Taylor didn’t have the energy to consider the possibilities, as he was too busy trying to act normal. Showing up to school in panties had already made it feel like everyone had X-Ray vision when he first stepped through the main doors; now that people were glancing towards him more than usual, that same illogical fear was creeping in.
Shifting in his seat, once again unable to ignore the difference in how it felt to wear girls’ underwear compared to his usual boxers, Taylor turned his attention to the projector and whatever problem that was being demonstrated. The crazy thing was, daycare was starting to sound a lot more attractive than the normalcy of his high school life being disrupted like this. Mortifying as it was to participate in immature games and activities, while everyone assumed he belonged there, at least it was in a setting that was almost completely isolated from his actual life.
Taylor took a breath, finding the slightest bit of solace in the fact that Sarah was in a different class this period. He just had to get through lunch, skip another practice, and deal with yet another dress after school. Sarah would almost certainly be taking more pictures and videos as well, as if the collection she already had wasn’t more than enough.
He wasn’t even halfway done, either. It was only Wednesday, and Taylor had to keep doing this ‘little girl’ thing through Friday. After that . . . He had no idea what Sara’s intentions were.