Scott blinked groggily, realizing he had more or less lost consciousness as his body, warm and plastered with a light, sticky layer of Carolyn’s foot sweat, was able to freely move again as the woman’s heavy, wrinkled sole gingerly lifted itself off of him, arching in the heel.
“Oh, my God, Carolyn,” giggled a voice that Scott recognized as Nancy’s. “You must have the magic touch.” Blinking a few more times and rubbing his eyes, Scott looked up out of the shoe to find all of the women crowded around Carolyn’s leg, staring down at the tiny naked teen laying in the base of her shoe. He blushed, quickly placing his hands over his crotch, watching the gigantic circle of women all snicker at his modesty far above him. His eyes followed up along Carolyn’s smooth leg, past her knee, and up to her face, where he made eye contact with her. She grinned sheepishly at him: the only one not rude enough to laugh at his misfortune. It was at this moment, then, that Scott realized he had actually fallen asleep in Carolyn’s shoe. Not gone unconscious or been knocked out, but physically soothed into slumber by the comforting touch of her soft skin.
If this had happened in the shoe of anyone but Carolyn, Scott had no doubt that he would’ve burst into tears from sheer embarrassment. As it was, it was mind-blowingly humiliating to stare up at the faces of all these women, them staring down at his fully exposed package and knowing that at some subconscious level, he didn’t truly mind so much being in a woman’s shoe as long as she was gentle with him.
With a cold cringe, Scott had a feeling his mother wouldn’t hesitate to use this as an excuse to implement this particular punishment even more often for his inevitable small-scale crimes. It would be just the sort of thing Judy would relish when calmly depositing her son into her shoe and letting him get tangled up in her toes: to not only force him in such a lowly position, but as well, to berate him constantly with cheerful reminders that no matter how much he tried to deny it, he wasn’t really opposed to participating.
“All right, ladies, we can continue the discussion now… I’m sure my son is suitably embarrassed for the moment, and since he fell asleep, there’s probably only time for one more massage,” winked Judy down at Scott. Bitterly, Scott knew perfectly well that his mother didn’t believe a word of that, and more just wanted to appear as a more loving parent to her subdued son. “Carolyn, would you say you’re about done with your turn?”
“Yes… yes, that’s fine,” answered Carolyn softly, looking down at Scott regrettably, as if trying to apologize on behalf of the women for what he was having to go through. Scott smiled up at her as if in thanks. “Thank you, Scott,” she said quietly.
“Sure thing,” mumbled the boy, clambering out of the shoe and back onto the carpet. Gulping, he turned toward Judy as she took her seat again, who extended a long pointer finger far above his head, pointing with a smile to the other side of the room. Scott turned hesitantly around to find himself facing Nancy and Susan, both of whom were wearing devilish grins across their supple, plumped lips, their perfectly white teeth glistening with delight. His eyes traveling downward, Scott watched as both women made their right feet writhe against the leather heels they were both wearing, squirming until they could wrestle their heel out and slide the rest of their peachy appendages out, leaving both of their shoes open.
“Susan, would you like to take a turn?” asked Nancy sweetly, turning to look at her friend. Scott flinched, feeling even more driven down than before. He wasn’t even being directly spoken to anymore; it was as if he was being passed around the room like a peace pipe. A fun object these aging beauty queens could toy with with zero consequence and absolutely no regret on their part at the expense of a teenager’s damaged emotions.
“That’s nice of you, Nance, but…” drawled Susan, pressing a pointer finger against her chin, obviously trying to concoct the most humiliating possible way this task could be performed in as she studied Scott like a customer might study a piece of meat at the butcher shop window. “…we’ve had our fun. Let’s give little Scott here some say in it, hmm?”
“Um… okay, I guess…” sighed Nancy dejectedly, clearly disappointed with such a prospect, but she shrugged. “What do you mean?”
“I mean, let’s let Scott decide. He thinks he’s man enough to drink alcohol, endangering himself and shaming his poor mother? Surely, then, he has to think himself man enough to make a choice about the consequences.”
At this, Nancy’s gleeful smile returned, and she looked back hungrily at Scott, rubbing her hands together greedily. She smirked victoriously down at him. “All right, babe, you heard the lady. Which one of us do you like better? We’ll let you pick this time.”
Scott fought back a groan with all his might. He turned and looked pleadingly at his mother, who, as he expected, simply raised her eyebrows at him, as if telling him to get a move-on. Quivering with adrenaline, Scott turned back to the women, swallowing hard and trying to make a hasty decision. It was essentially like picking his poison, but somehow Scott knew there was an objectively better choice here. Nancy was a bit creepy with her overt seductiveness to basically any man over the age of sixteen, and he had no doubt she would enjoy her turn with gut-wrenching enthusiasm, but at the same time, he knew it would be infinitely preferable to being under the vengeful foot of Susan, whom he was positive would make him feel her hatred of men deep in his bones as she mashed him into her sole flesh to within an inch of his life.
“Mrs. D-D-Dugan,” he mumbled, trying to keep it together, as he ambled forward. The women all chuckled a little as Scott got closer and closer to his chosen punisher’s titanic shoe.
“C’mon, babe, let’s pick up the pace…” giggled Nancy girlishly. “We only have a few minutes left before the club ends, and I want to make sure I get my full turn with you.” At these words, she began to clench her toes into the fabric of the carpet, scrunching her sole down against it. Probably in preparation for whatever she had in store for the teen. Scott trembled painfully.
Reaching her shoe, Scott sighed heavily, staring into the velvety, dark abyss of the thing. Despite the fact that Nancy would probably be a little less painfully harsh on Scott than Susan potentially would, her shoe, unfortunately, was a different story. With a thick velvet-lined exterior, a healthy padded leather exterior, no open toes, and a raised heel, it ensured the shoe was almost definitely going to provide little-to-no air. Swallowing hard, Scott blinked a few times, getting mentally prepped.
He didn’t have long for this, though, as he found a strong, meaty big toe gently tapping itself against his rear end. Blushing and cringing at the same time, Scott took a step forward and a moment later found the big toe sliding itself down the side of his body, Nancy’s second toe snaking its way around his other hip. Gripping him tightly into her toe crevice, Nancy then raised her foot up over the shoe. Scott’s blood turned to ice, his legs dangling precariously over the drop, and with no other safety option, he gripped the forty-nine-year-old’s meticulously pedicured toes as if his life depended fully on it. This didn’t last for long, though, as Nancy jammed her foot roughly into the heel while still gripping Scott’s body between her squirming toes, pressing it firmly down against the pointed toe section.
Scott almost began hyperventilating, the muggy area instantly overtaking him and making him sweat. His body was pinned hard against the wall of the shoe, and as he struggled, trying to wrestle free from the grip of Nancy’s toes, he felt a painful twinge in his groin and stopped moving instantly, lest he injure himself. Despite the darkness of the shoe, the extremely thin crack of light finding its way into the depths of Nancy’s heel allowed him to realize that although he was partially wriggled out of the grip of Nancy’s toes, most of his waist was still entrenched in the crevice, and worse, his dick was pinched firmly between Nancy’s squirming digits. He sighed with fear, terrified that the woman would unknowingly squeeze her toes and snap off his member.
As usual, Scott’s fears were not only realized but brought to a far worse form than he could’ve dreamed up in his worst nightmares.
“What do you think, Nance?” came the muffled voice of Susan through the leather walls of the heel.
“Oh, it’s fantastic…” chuckled Nancy with pleasure just a little too close for comfort to sounding like arousal. “You know, it’s… it’s funny, but… my ex, Tom, and I used to play these little games with each other once I got my license to use the ray. He was… quite a bit younger than me, you know, only about 28, I think, and… well, he still had that youthful energy I love so much. He always had a thing for… well, my feet, I guess. He was one of those people. Not that I minded, of course, since he was pretty good in the sack too, but the thing is, he had this weird little… kink, I guess you could say… where he wanted me to use the ray on him and play with him a bit… down there,” she whispered naughtily, much to the giggling of the book club and Scott’s chagrin. “This is basically what he used to have me do with him. I wouldn’t walk anywhere, of course, but once I had him in the shoe, I’d just…”
“Oh, Nancy, you sly little bitch,” chuckled Susan playfully.
“You should’ve seen me in high school, honey,” said Nancy as an aside. “But, anyway, I’d get him in there, right where I wanted him. I was pretty good at it after a while, too, and I’d just…”
“Nancy, Nancy, Nancy… you be careful,” said Judy jokingly. “Scott’s just a little bit below the age range… even for you.”
“What, are you implying I’m too… old?” snickered Nancy, and at that moment, her toes clamped around Scott’s member. He winced, gasping for breath and tightening his muscles for impact, until he realized there was no pain, the pressure had simply increased greatly. His dick was now firmly locked in the thick embrace of this cougar’s toes, and it wasn’t going anywhere until Nancy wanted. Then, slowly, Scott could feel motion in her flesh. It was subtle: a simple grinding together of her toes, but it quickly picked up the pace, and in no time at all, Scot could feel a familiar, warm feeling rushing through him: pleasure, ecstasy, hotness. His brain rattling around confusedly, his heart rate increasing. His member beginning to enlarge as the gargantuan toes of Nancy continued squirming, still wrapped firmly around Scott’s dick, with the obvious intention of reliving a game she used to play with a man in a past relationship.
Jesus Christ, thought Scott. What the fuck is wrong with me?
Seriously, what the fuck?
He couldn’t handle it. The warm, soft skin of her toes. The powerful, rhythmic pumping motion. The unbearably oppressive heat clouding his thinking. The slick lubricant of foot sweat helping Nancy’s toes glide with practiced caution around Scott’s miniscule package, her obvious experience in this type of foreplay given away by her absolute carefulness. Scott felt no pain, only insane, embarrassing pleasure rushing through him as he was forcibly jacked off by the monstrous foot of this overly eager family friend. Each squeeze of her toes brought even more intensity, until Scott realized he was moaning with pleasure, his body shaking in preparation for what was inevitably to come. Literally.
“Nancy, this has got to be some kind of all-time low for you,” laughed Jill.
“What are you talking about? He LOVES this!” snickered Nancy. “DON’T ya, babe?” she called down toward her foot. Scott felt the pumping of her toes cease for a moment as her foot flexed, pinning him harder against the velvet wall. He groaned, his body clearly annoyed at the interruption so close to climax, but soon found Nancy’s toes easily gripping his package and getting right back to business. All Scott could do was moan loudly in response, despite the humiliation he was feeling. He couldn’t help it. It might’ve been disgusting, and mentally, one of the least arousing situations he’d ever been in, and yet he couldn’t deny the sheer, unbelievable experience of Nancy. She knew the motion perfectly. She knew exactly how to push all of Scott’s biological buttons, even if he didn’t want her to, forcing a reaction out of him by taking advantage of the simple fact that he was a teenage boy.
“I’ll take that as a yes,” she sighed with pleasure, and with a final, powerful jerk of her toes, Nancy gripped her foot over Scott more tightly as the shivering teen gasped and reached the single most embarrassing orgasm of his entire life. Shivering and struggling for breath, the spent teen collapsed on top of Nancy’s fleshy toes, tears of humiliation flowing down his face.