Chapter 6: Tiffany has some questions

After Ashley was gone and Tiffany was left alone in the classroom with you, Tiffany grinned. “Okay, my little ass passenger… I mean, ASSenger…” You were still trying to twist your face from this girl’s asshole as Tiffany giggled at her own stupid joke, “I need to go get a drink of water, and then we can chat a bit before gym class starts. So just hang on!” Tiffany giggled again as she began to saunter out of the room, knowing you had no choice but to come along with her. Tiffany considered that she basically controlled your fate with her butt, and smiled at the thought. Tiffany walked over to a water fountain, and bent over to get some water. Tiffany felt you begin to struggle as her buttocks spread slightly, despite being pressed together by her tight dress. Tiffany shifted her weight on and off each foot as she drank, unmindfully causing her butt cheeks to chew your face up as they ground together. You groaned in pain, which Tiffany felt as she finally stood up, but didn’t bother to acknowledge except by saying, “Alright, wasn’t that refreshing? Now, time for gym.” She headed for the locker rooms, enjoying every step she took as you were continually smushed between her shaking ass cheeks.

Tiffany reached the locker rooms, grabbed her gym outfit (a skirt and small top) and headed to a private changing room. She undressed, finally releasing her large rear from the incredibly tight confines of her stretchy clothing. Tiffany turned her back to the wall length mirror on one side of the changing room, and looked over her shoulder into it. Without pulling her buttocks apart, she couldn’t see you at all. Tiffany smiled, and shook her hips just slightly, sending her buttocks slamming into your back. “Hey little guy, are you still in there? How come I can’t see you?” Tiffany asked, fully aware that you were still caught in her ass but wanting to tease you. You shouted up at her angrily, but Tiffany only smiled and played dumb, “Oh! That’s right. You’re stuck waaaaay up my gorgeous butt.” Then Tiffany peeled her enormous ass apart, finally revealing your tiny body, stuffed all the way between her ass cheeks. The giantess giggled when she saw her first personal glimpse of the tiny man trapped by her butt; you were even more pitiful than she had imagined. Tiffany smiled and bit her lip to keep from laughing as she studied the way your body was tightly wedged between her colossal butt cheeks, with your arms practically pinned at your sides.

Tiffany’s smile grew even wider and crueler when she saw how your torso was held right next to her hole, with your head almost disappearing inside of her tight pink anus. “Wow.” The giant girl stated, examining your helpless form. “I really hope for your sake that you’re an ass man, or this must be just awful!” Tiffany then pushed her butt cheeks together a bit, laughing at how easily you were squished between them over and over. Tiffany kept teasing you as you disappeared and reappeared in view from her ass cheeks, “Of course you’re an ass man! Why else would you have your head stuck up my beautiful behind? Unless, of course… I sat on you or something by accident.” Tiffany thought to herself for a second, thinking about how easily she could have dropped her ass on top of you without even noticing. “Well, however you got in there, you’re getting a real faceful of my ass now, huh?” Tiffany smiled as she examined your predicament: you were trapped by your face in an ass dozens if not hundreds of times your size. Tiffany couldn’t stop giggling as she imagined your helpless little body being sandwiched between her two gargantuan butt cheeks as she walked around, or sat down at a chair. Tiffany began shifting her weight from side to side, letting her ass cheeks slide back and forth or bounce up and down, just to see what would happen to you. Of course, you were continually battered and ground between her huge masses of flesh at your sides, much to Tiffany’s amusement. You tried to scream for her to stop, but Tiffany only giggled, teasing, “Whats wrong? Is my big butt just too much for you, little man?” Then she gave her ass a slap, causing you to jiggle around as her buttocks quivered left and right.

Tiffany bent over, causing her butt to spread apart enough to reveal most of your body, though her ass cheeks still held you firmly in place. “Well, I can tell by your constant struggling and screaming that you’re probably not enjoying your up close and personal look at my ass. Am I right?” Tiffany smirked when she felt and barely heard a muffled, “NNNFFF” come from her butt. “Well then, my unlucky little friend, how DID you get wedged so far up my ass?” You couldn’t believe how many strange, demeaning questions this girl was asking. You took another stale, sweaty breath from her bowels and shouted up at this uncaring girl as loudly as you could, explaining your predicament to her, despite her asshole pinching your face together like a vice. After you finished explaining what happened, Tiffany only laughed and said, “Sorry, tiny, but I didn’t catch any of that. My big ol’ butt was in the way, hahaha!” Tiffany only laughed further when she felt an angry buzzing against her asshole, as you began screaming up at her. How could she be so stupid and mean? Did she not realize she was making you breathe in the air from her ass every time you wanted to speak? Tiffany only howled with laughter as she watched you began banging your fists against the pink walls of her anus, furiously trying to get back at her.

Tiffany, still bent over, wiped a tear from her eye and said, “Okay, okay. Enough fooling around, I’ll help you out.” Then, the giant girl reached back and easily plucked your head from her tight asshole (though she left your lower body pinched between her large butt cheeks). Tiffany watched you coughing and hastily breathing in as much fresh air as possible, before smiling, thinking that her ass really did a number on you. “So, tiny…” Tiffany began, “How did you get, like, stuck in my butt or whatever?” You took a deep breath, trying to keep from berating at the giant girl who’s ass you were still being pressed against for leaving you there so long, and disclosed everything again. You revealed how her friend Olivia had shoved you between her cheeks and everything, but before you could finish Tiffany interrupted, “Haha, so when Olivia slapped my ass, she was really just shoving you in? That’s so awesome. I can’t believe I didn’t figure that out on my own!”

You weren’t happy about how well Tiffany was taking all of this, and you said, “How is that awesome? I was being crushed by your ass the whole time!”

Tiffany chuckled again, “Oh, well, I guess I meant it was awesome for ME. Sorry tiny, I should have clarified, but I’ve really been enjoying all this. That’s why I didn’t let Ashley help you earlier.” The way Tiffany spoke so carelessly about trapping another person in her anus was making you angry, but she was still holding you inches away from her butt crack, so there wasn’t much for you to do.

You shouted up, “Can you please stop calling me tiny!?”

Tiffany teased, “Well, I mean, you ARE tiny, though! My big gorgeous ass is like a hundred times your size. Here, I bet I can push you back into my butthole with just one finger!” You tried to scream up at the giant girl to stop, but she placed her index finger against the back of your head and began to push. You braced your arms against her anus to resist, but she effortlessly forced your face towards her pink and sweaty anus. From up above you heard Tiffany mocking you and giggling, “Uh oh, you’re getting closer, tiny!” Your cries soon became quickly muffled as your mouth made contact with Tiffany’s warm flesh. You continued trying to scream, but Tiffany only laughed and pushed harder, burying your face into her butthole. Tiffany twisted her finger a bit, making sure to really jam your face into her ass tightly, before she pulled her hand away. You were once more left with your face stuck up this giant bimbo’s asshole. Tiffany wiggled her rump in the mirror, ensuring you were really stuck, and said, “See? I told you, tiny! I win the bet.” Then Tiffany clenched her anus victoriously, making her asshole chew your screaming face up as it pulsated, while your limbs thrashed wildly but ineffectively against her anus.

What happens next?