Patreon Story: The Road Trip, Part Five

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Part Five

Unbelievable.

As if one pull-up wasn’t enough. Ever the one to push her luck, Kate seemed intent on doubling up the bulky underwear that I’d be wearing for the rest of the drive. I knew exactly what she was doing, and yet it was working anyway. Now that I was already wearing one pull-up, I was stuck with the choice of either putting on another one or calling this off and getting nothing for my troubles.

At this point, I was in too deep. What’s an extra layer? Either way, the underwear is embarrassing. It’s not like a second was going to make a difference in that regard.

“Fine.” Not wanting to argue this time around, especially since every minute wasted was going to require some bullshit explanation to our parents who were no doubt impatiently waiting in the car, I just pulled out a second pair from the pack.

Kate just gave me a warm smile. “What a good little sister!”

I just gave her a look, then got to work putting on the second pull-up. Like usual, there wasn’t any point trying to get on her case. If I snapped that I was the older sister, or demanded that she not call me that, it would only enable her. I’d also have to deal with her roundabout logic about how my size somehow makes me younger, or maybe just her classic claim that she was only teasing while telling me to ‘stop freaking out over nothing.’

The second pair of pull-ups slid up my legs just as easily as the first, until they reached the padded underwear already on me. Blushing as I dealt with the bulky resistance, it took a good amount of tugging and squirming to work the double pull-ups into place. It was like trying to put on jeans that were fresh out of the dryer, only worse due to my hands being under my skirt and my sister watching with an amused giggle or two.

I managed to get them fully on, but it was tight. And, worse than the padding that was now so snugly wrapped around me, the bulk between my thighs was more noticeable. I couldn’t fully close my legs. Not the end of the world with a long skirt, but definitely not a sensation I was used to after exclusively wearing mature underwear for so many years.

“Took you long enough, Annie,” Kate said, “Now let’s go. You’re making all of us late.” She tossed the rest of the pull-ups into her purse, ‘just in case,’ then opened the bathroom door for me.

It was now or never. I was either about to walk out into public while wearing pretty much the most embarrassing underwear imaginable, or I was going to panic and call this whole thing off.

Against my more mature instincts, I left the safety of the bathroom in the pink pull-ups Kate dared me to put on for the drive. It was going to be worth it. Now that I had put them on, my younger sister already had new ammo to tease me with. A few more hours wouldn’t make a difference in that regard, so it was better to just suck it up and see this through so I could at least be called ‘Annelise’ for the weekend. Kate may be a brat, but she still kept her promises.

I was hoping to just get in the car and finish the drive as quickly as possible, but of course Kate volunteered us to clean out the trash in the back seat before we got on the road again. There wasn’t anything telling on her face, but I was pretty sure the goal was just to make me walk around in pull-ups for another few minutes. I waited impatiently as she shifted a few of the bags and moved things from here to there in the trunk, and eventually let her hand me a few things to throw away with her.

Just as we reached the bins around the corner, I felt Kate’s hands shifting the waistband of my skirt. “Oh, Annie! Make sure your pull-ups don’t poke out of your skirt,” she said. No boundaries, like usual.

I was about to correct her on my name, before remembering that I had agreed to let her keep calling me the immature nickname as long as this dare was happening. And, while I was tempted to push back on the possessive word yet again, the bigger issue at the moment was my personal space. “Kate, I can do it myself,” I said.

“It’s fine, sis. I’m almost done . . . Wait, Annie! Are you wetting yourself??” Kate gasped.

I barely registered the words as I felt Kate’s fingers slip between my skin and the waistband of the pull-ups. Both my skirt and underwear were swiftly pulled away from my body, and I suddenly felt cold liquid running down my ass less than a second later.

It was like nothing I had ever experienced. The cold drink flowed down my crack and pooled at the base of my ass, but it didn’t continue its journey down my legs. Instead, the innermost pull-up absorbed the liquid and the crinkly material clung to my skin. “Kate!” I exclaimed. Her hand slipped away as quickly as it had arrived, but the damage was done. I spun around to see my sister smirking with her yellow gatorade bottle half empty. “What the actual fuck, Kate?! That isn’t funny!”

Enough was enough. This wasn’t worth the deal; I couldn’t just let Kate push this dare further and further. No way in hell was I about to wear wet pull-ups for a multi-hour drive. Ugh, I was just going to have to strip and wash the sticky drink off myself, and then go commando for the rest of the ride. Going back to the car for my regular underwear first was going to waste more time, and then Kate would have the chance to blame me for our lateness.

“No way, little sis.” Kate took a sideways step to block me from making any progress forward. “Go get in the car, or I tell our parents that you wet your pull-ups.”

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