Truth or Dare - Chapter 9a (Patreon)

“Good morning, sleepyhead!”

Ted was only half awake when he heard Abby’s greeting, but was brought back to full consciousness when she slung her shorts onto his face. He groggily pushed them away, in time to watch her lean over him with a giddy smile. “Morning,” he yawned, snuggling deeper into his covers.

“You got three options for the day,” she said. “A, B, or C.”

“Which… what?” he asked, still tired and confused. “Uh, B I guess.”

“So between Ass, Boots, and Collar, you picked Boots? Huh, didn’t realize my roommate was gonna be such a foot freak.” She was only teasing of course, but her quip struck a chord with Ted. As he obediently got on the floor and slid his back into her unzipped, knee-high leather boot, his mind was elsewhere. ‘My roommate, my roommate,’ he kept repeating in his head. After the lengths they’d gone to, it practically seemed unfair. But in fairness, he hadn’t actually popped the question to Abby yet, not officially. So maybe he should.

“Hey Abby, do you wanna be my girlfriend?”

Towering over the little man, about to slip her foot on top of his body and zip the boot up, Abby paused, her large, pink sole hovering above Ted’s face. “Girlfriend?” she mused, her foot blocking out the boy’s ability to see her expression. “Do I wanna be your girlfriend? Hm… quite the bold question to ask a girl before she’s about to step on you, isn’t it?” Her toes wiggled teasingly above, as if mocking him for asking that a strong, gorgeous woman three times his size would want a scrawny guy like him as a romantic partner. “I’ll have to think about it,” she cooed, and resumed in sliding her foot atop him, bending his legs upwards behind her heel, and zipping it all together so that he was firmly and thoroughly trapped beneath her foot. “But in the meantime, if you’re looking for some girlfriends, then I know my toes are all single and would love to spend some time getting to know a guy their size. So feel free to show them some affection while I think about your offer.” Although it was a little demeaning, Ted knew that playing along would help his chances more than hurt them, so from within the dark, increasingly warm confines of his roommate’s boot, he gingerly started to kiss her pudgy digits that danced across his face, while she finished getting ready for her day.

Although he generally enjoyed being dominated by women, most of all a girl like Abby who he’d quickly developed a strange kind of bond with, being turned into a human insole was never exactly fun. It was like with people who are into BDSM: the pain doesn’t go away the more they get slapped or whipped or choked—it’s that they enjoy the experience despite the pain, if not because of it. And as the fiery, Amazon-sized 18 year old above him walked to her classes, each step causing her heel to squish his dick and the ball of her foot to crush his chest, Ted couldn’t say that the experience wasn’t a bit painful. And yet it was despite the pain that the endeavor electrified him and sent an addictive cocktail of adrenaline and endorphins throughout his body. Because he was treated as an object. Not metaphorically, but literally, a mere shoe for this beautiful college freshman. Though it was clear that she was constantly aware of his presence, whether due to her ever-wiggling toes, or the way she’d tap her boots against the ground during class as if mocking his inability to escape or complain, or the period that she put her feet up on a table and drummed the heels against its edge as if hammering Ted’s dick into the worn-out rubber insole to keep it from growing erect.

After a handful of classes, and several hours of confinement to Abby’s boots, she finally let Ted out to have a break and stretch his limbs. “You got about ten minutes to stretch, drink some water, and have a snack,” she informed him, handing him a pre-made sandwich from the cafeteria and a mini bottle of water. “Then we gotta head to the gym.”

He didn't waste time scarfing down the food, even though he technically hadn’t actually done any physical activity, confusing bodily soreness with tiredness. But before he was even done eating, he was up on his feet and struggling to keep up with Abby as she walked to one of the university’s on-campus gyms. “In here,” she told him when they were less than a minute away, ducking into a family bathroom off to the side.

“I wanna try something new for my workout,” she said as she took off her shirt. “Arms to the side.”

Ted didn’t know where this was heading, but he played along and became still as a statue, allowing Abby to pick him up and turn him sort of upside-down. He watched as his field of view was raised higher, until he was positioned above her cleavage. “Um—” was all he managed to say, and then his head was being plunged between her breasts.

Giggling at his reaction, Abby reached up beneath her sports bra and used her hand to guide Ted’s head to the side, squishing and sliding him across her boob fat—and her nipple—until he reached a nesting spot just beyond the edge of her breast, where his head became basically squished against her sideboob by the bra. Then she laid out the rest of his body beneath the rest of her tits, so that he wasn’t quite in front of them but wasn’t hung entirely beneath them either. His body basically acted as a kind of extra-thick padding for her breasts, and because he was so light, it didn’t even weigh the bra down very much. Satisfied with the results, Abby put her shirt back on, and headed back out to make her way into the gym, determined to see if she could comfortably complete a full workout with her shrunken little roommate trapped inside her bra.

For Ted, the ensuing exercise session was still a bit uncomfortable, but a whole lot less painful than the time spent in her boot. Although Abby’s boobs were heavy and he was compressed between them and the bra, it was a lot less heavy than the weight of her entire body stomping on his face. And of course, as a straight man, he much preferred getting to cozy up with the girl’s boobs instead of her feet. Although they smelled worse, ironically enough. But that was to be expected from an hour-long workout. After swinging around and battering into his body thousands of times, the girl had worked up a copious amount of sweat, and Ted was left to deal with it all as it drenched his poor body and coated him without any remorse.

Upon finishing her time at the gym, Abby took Ted back to the family restroom to retrieve him from her bra. “I expected you’d leave me in there until we got home,” he said after she set him down, using a paper towel to wipe off his face.

“Well I felt a little bad with how slick things were getting down there,” the reddened, sweat-laden teenager confessed. “So I figured I’d stop beating around the bush and just tell you. I accept your proposal to be my boyfriend,” she beamed, giggling at how quickly his face lit up. “As long as it doesn’t interfere with our little, you know, arrangement here. I don’t want you saying, like, ‘Oh, you’ve kept me on a collar all day and walked me around like a dog, why won’t you just take me out like a normal couple.’ I don’t want that. If I wanna treat you like a puppy then I’ll treat you like a puppy, and if you’ve been a good puppy, then I’ll let you be a regular boyfriend every so often.”

Ted didn’t even hesitate, so much as he probably should’ve, and immediately nodded in compliance with her demands. “That’s okay with me, no problem.”

“Great!” she grinned. “Then as my new boyfriend, I want you to climb back into my other boot so I can trample all over your face on the walk back home.” Wasting no time, and honestly with a little too much pep in his step, Ted got down on the floor, and before Abby could even take her shoes off herself, he was unzipping the one he hadn’t ridden in that day and sliding into it in preparation. Abby smirked, “Wow, going above any beyond. I might just have to reward you later tonight.” Hearing such a salacious promise, Ted’s dick stirred a bit at the thought, before the giant girl unceremoniously stomped it right back down as she put her shoe on, zipping everything up like before, and then headed back out onto campus to make her way home.

~

P.S. there was supposed to be one more scene, but i have to send my laptop off to get fixed so i don't have time today to finish it and figured it'd be best to just publish what i have atm. will include it in chapter 10!