"That's what I like to hear, Jake. Well for starters I have something stuck deep in my boots and I just can't seem to get it out. You wouldn't mind helping me out would you?" Kimberly said down to you. She leaned forward as she finished her sentence, almost blocking out the light coming from the lights in the ceiling. Kimberly's mannerisms combined with her incredibly tall stature and threatening confidence terrified you. As much as you wanted to say no to this task you knew that would only lead to more trouble. And as you thought back to how dirty the soles of her flip flops were earlier, you had a bad feeling about the boots that you would need to deal with now.
"No sweat at all, Miss Smalls, I'm sure I can feel around there and pull out whatever has been bothering you!" You attempted to feign both confidence and enthusiasm. Kimberly clearly didn't buy it but your agreement was good enough for her.
"Wonderful, stay here I'll go get it" Kimberly said with a wicked smile. She exited the room, closing the door behind her before coming back momentarily with the aforementioned boot. For some reason when she mentioned this pair of footwear you first assumed it would be a simple pair of short boots that the average person would wear. However what you saw in her hands induced much more anxiety than you had before. The boots must have reached at least her knees, perhaps even her massive thighs, as the scuffed, worn brown leather seemed to go on for miles. Shutting the door once again and locking you two in her office, her flip flops slapped closer and closer to you as her right foot briefly hovered right where your body was. You gave out a scream, "WAIT" and dove out of the way as she stomped down in the exact moment you were a brief second before. Kimberly paused on that step and looked down to see your body lying flat on the ground, safe for the time being, but mere inches away from her foot.
"Oh, I assumed you would have climbed up on the desk to wait for me at least. You know it's very dangerous for someone of your stature to simply stand around on the ground while us normal sized girls in the house are walking. You should be more careful next time." Kimberly didn't even attempt to sound apologetic as she criticized your position after nearly squashing you flat for the second time today. Before you could muster a response she dropped the boot down on the other side of you. Its sole stamped down into the floor roughly and she grabbed the leather at the top, holding the boot up to its maximum height. It towered over your one foot tall frame, dwarfing you by over double your height. Your ego took a hit to see how much taller this boot was than you, but once again Kimberly spoke before you could even have a second thought.
"Well, are you ready? I figured I could just hold you by your legs and lower you in while you grab whatever is in there. It's somewhere near the toes of the insole." Kimberly lined out your tasks as if she was simply asking you to do a simple task like take out the trash, not even pretending to care that she was asking you to go cave spelunking in her massive, clearly worn out boots.
"Umm, I guess that makes sen..." you were cut off as Kimberly bent over, flashing you the briefest view of her cleavage before grabbing both of your feet together in one massive hand. Immediately you felt your world turn upside down as she swung you into the air and hovered you over the boot opening like some sort of portal to hell. Without saying another word, Kimberly lowered your body into her shoe as carelessly as one would lower a plunger into a toilet. Sadly at this point you felt like you were nothing more than a tool to your (hopefully) future mother-in-law and you were too worried about winning her approval to say otherwise.
Immediately upon entering the boot you felt the warmth of its leather walls emanating powerfully. And as you were lowered deeper and deeper it only continued to heat up. Even worse, along with the heat came an awful odor coming up from the depths. It smelled like the natural nice scent of the shoe's leather was actively battling against years of built up foot sweat, and the leather was losing badly. As you got lower and lower the space you were filling got tighter as well. Even though you were incredibly small by normal human standards, you were still big enough to feel cramped being shoved into a woman's boot. Luckily, or you might say unluckily, thanks to the myriad of previous situations in your life similar to this you had overcome any feelings of claustrophobia from these tight spaces. A second later you felt your head hit the bottom, a slight warm and damp insole that had clearly seen years of use. You paused momentarily before Kimberly began to shimmy your body now forwards into the toe section of the shoe. At this point the smell was practically unbearable, and almost all of the light had been blocked out as well. You couldn't believe that she would ask you to do something like this, but there was no turning back now.
"I hope they don't smell bad, Jake. I was just wearing them for hours before you and Cassie arrived. I probably should have told you that beforehand but I'm sure you don't mind." Kimberly said, then continued, "Just tell me when you're deep enough in and I'll stop pushing." In reality you could barely hear her voice, and she couldn't hear yours at all. The thick walls of leather muffled any sound you attempted to make. As your head hit the toe end of the shoe you felt Kimberly continue to press your legs forward. With nowhere else to go your body's squishy characteristics started to kick in and you already start to feel yourself become compressed.
At this rate Kimberly was going to just squash you flat into the front end of her boot and you would be incapable of even completing your task. You could only pray that this wouldn't happen as the only thing you feared more than being in this dank, sweaty cave of a boot was failing to complete Kimberly's task.
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