“Kate, what are you doing?”
“Making sure you do your dare! What, would you rather lift your skirt to prove it outside?”
“No, but-” I began, trailing off. As usual, my sister had a way of making it sound like she was right. There were plenty of reasons why I shouldn’t have to do what she was suggesting, but none of them came to mind. The visual of lifting my skirt in public, showing off pull-ups that I was now wearing, was enough to give me pause. That, and arguing would no doubt just draw this process out.
As always, the best option was to just act like none of this bothered me.
Resisting the urge to sigh, I opened the pack of pull-ups. Knowing that any hesitation would only result in potential teasing, I wasted no time taking one of the bulky pairs out. The light pink made me reflexively cringe, as I had given up the color years ago. For a redhead my size, pink wasn’t the most flattering color. Thankfully, the childish underwear would be under my skirt. Unfolding the pull-up, vaguely familiar with the material from my babysitting days, I adjusted my weight so I could step into the first leg hole without inadvertently flashing my sister.
“Annelise, what are you doing?” Kate asked.
“What does it look like I’m doing?” I was actually a bit surprised she interrupted, considering how I could still change my mind at any second. I definitely caught how quickly she turned my question around on me.
She just sighed. “You don’t wear pull-ups over regular underwear. What if you have an accident? That would be a total nightmare to deal with!”
“Why does it matter? It’s just a stupid dare.”
“Then do your stupid dare properly. Otherwise, it doesn’t count.”
For a few long moments, I just stared Kate down. Was she really going to insist on this? It was bad enough that I was letting her watch me put on pull-ups, but low key stripping in front of my sister was uncomfortable too. That same small voice in the back of my head was telling me to just throw the recently purchased underwear into the bathroom trash can and walk away, but I was mentally committed now that we had circled around promises and deals for so long already.
Without much bravado, I simply reached under my skirt to get a decent grip on my underwear. The entire time, I kept a close eye on Kate, still suspicious that she might try to catch some of this on camera. She didn’t, thankfully, and it didn’t take long for me to tug my panties down my slim thighs. It was wearing a boring white pair of underwear, and I was immediately tempted to explain to my fashionable sister that I had only chosen such a set since we were on the way to visit our cousins; the last place nice underwear really mattered.
Kate didn’t tease me, surprisingly, though I guess she was already pushing her luck with everything else. I let the underwear drop to my ankles and I stepped out of the leg holes as gracefully as I could manage; not only was the light breeze underneath my skirt embarrassing, but I also didn’t exactly know what to do with the underwear now in my hand. Putting them in my purse seemed a little gross, so I ultimately decided to tuck them into the open pack of pull-ups.
“Happy?” I muttered.
“Now put on your pull-ups, Annelise,” she simply said in response.
Now that we weren’t in public any more, I could be more vocal about my distaste for that particular phrase. “They’re not mine, Kate.”
“Oh, I’m sorry, sis. Did we buy them for someone else? Or did we buy them for you?”
“You know what I mean.”
As usual, it wasn’t worth trying to deal with my younger sister’s ‘logic.’ Instead, the best play at this point was to just get it over with. Letting Kate get a rise out of me would only enable her. Her size advantage and her teasing would always bother me; I just had to get better at not letting it show.
Taking the partially unfolded pull-up I had temporarily set aside, I got to work. Trying my very hardest to pretend Kate wasn’t watching me with an amused grin, I stepped one foot after another into the leg holes. ‘Please don’t fit, please don’t fit.’ I quietly prayed as I slid the childish underwear up my legs. They were designed for tweens, and I was a nineteen year old college girl. Admittedly, my legs were pretty twig-like and my lower curves were even less impressive than the upper ones, but still. I was an adult.
Then again, what would happen if they didn’t fit? Technically I made an attempt to try them on, which was kind of the dare. But if I couldn’t wear them for the whole car ride, which was definitely Kate’s stipulation in regards to calling me ‘Annelise’ once we arrived, would she claim my efforts didn’t count for anything?
I didn’t have to wonder for too long. When I reached my thighs, the pull-ups didn’t resist in the slightest. Unable to help my blush the farther upwards I went, I soon found the waistband of the padded underwear wrapped snugly around my hips. When I felt the slight bulk between my thighs, and the padding against my ass, I was immediately tempted to just yank the embarrassing thing all the way back down my legs. But if it was sunk cost fallacy before, I was definitely in too deep at this point. There was no way I was going to give Kate the satisfaction of putting on pull-ups and letting her screw up my name on purpose because I bailed so soon.
“Well? Do they fit?” Kate asked. She gazed at me with curiosity as I removed my hands from underneath my skirt and adjusted my outfit to make sure nothing looked out of place after changing underwear. My expression must have said everything, because she smiled widely at my awkward silence, “Oh my God, I knew it!”
“Let’s just go,” I muttered. The longer we were in the gas station bathroom, the more strongly I’d consider just calling this whole thing off.
“Not yet,” she said. She grabbed the pack of pull-ups and pulled out another one. Holding it out with an expectant expression, she explained herself when I glanced back in confusion.
Your dare was to put on pull-ups, Annie. As in, more than one.”
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Stories of Age/Time Transformation