Flagpole Fun

Meryl cringed at the feel of the gusset of her panties stretched taut against her pussy. Far below her, Kayla was waving her arms frantically and trying to release the flag pole's mechanism, to little avail. Although she was currently hoisted high above the ground, the waistband of her panties thoroughly stuck on a large hook attached to the flagpole, she wasn't in all that much discomfort down below, on account of how oversized Cheryl's underwear was on her. This was one saving grace in yet another of what was now firmly established as a growing series of searingly embarrassing scenarios; she shifted slightly to rid herself of a bit of chafing, and groaned inwardly as she instead simply made the panties slide further into place in the cleft of her arse crack, intensifying the humiliating wedgie she'd managed to get trapped in five minutes prior. Kayla was yelling something up at her, but the distance between them was great enough that the words were snatched away before they ever reached Meryl's ears. She sighed in frustration, giving herself a pseudo-reach around in an attempt to pick the panties out of her backside, plucking daintily at the material of the gusset and shivering every time her nails pricked at the delicate skin of her vulva. Unbeknownst to Meryl, this small action seemed to put a bit too much stress on the panties, and on a micro-level, threads within the undies started undoing and tearing as she hung there. Meryl quickly desisted, figuring she'd accomplished nothing save deepening her wedgie, and focusing instead on trying to grab the flag pole behind her, bracing herself against it with her feet.

The pole creaked loudly, and Meryl looked around anxiously. After a second or two, when it became apparent that the sound wasn't going to continue, she kept on as before, her fingers scrabbling against the pole's smooth surface. The pole was cold against her legs, though her skirt covered what lay above them, which provided at least a bit of sensory relief from the relentless train of humiliation she'd been stuck on all day. With a triumphant grunt, she managed to grip the pole with both hands, simultaneously wrapping her legs around it, making her shiver again as the cold began to spread onto her calves, and a little ways up her thighs. This was working, she might actually be able to get herself out of this! She felt a lightness in her chest — pride, maybe — things were finally starting to look up! At that exact moment, the stitching on her panties finally gave out, and with a loud tearing sound, they tore in half at the gusset, the front and back of them dividing and splitting away from each other. Meryl felt a note of shock run through her as she realised what that meant, looking up at the hook above her, the hook that was the only thing keeping her...up...here...

A half-second before she began to fall, Meryl let out a pathetic little whimper, and then gravity did its work, and down the pole she went.

*

Five Minutes Earlier

Meryl speed-walked through hallways and courtyards, hurrying to the flagpole she and Kayla had agreed to meet by. While she walked, flashes of her previous humiliations came to her, and her jaw clenched a tad more with each new recollection: Kayla wrenching the purple g-string up into her crotch as Coach Merryweather walked in, flashing her arse and singing her top in the middle of Science, feeling Cheryl's fingers probing up into her butthole, feeling that Workman's dick wedged between her butt cheeks, the dream of hot dogs worming up into and past her butt cheeks. There was a disturbing pattern of...butt stuff, the worst kind of stuff, in Meryl's estimations. It was made worse by the deviant twitching her butthole had taken to engaging in ever since Cheryl's probing, the apparent...desire, for it to receive something long and stiff and—and hard. Meryl shook her head, she didn't want that, of course. That was a strange, uncontrollable desire her body seemed to hold, something wholly divorced from her conscious mind. Of course that was it. It couldn't be anything else. She walked on, trying not to dwell too much on that last thing.

The outside of the Campus was fairly populated, isolated pockets of people and individuals walking in one direction or the other as Meryl approached the flag pole, seeing it coming up across the last courtyard she emerged into and weaving between little knots of crowds as she drew closer to it. She thought she saw the figure of Kayla standing on the other side of it. Meryl couldn't help but smile, and as she came within spitting distance of the pole, she stepped around it to reach Kayla, and tapped her on the shoulder.

Kayla turned, her neutral expression immediately turning to genial smile. "Mer Bear!" She greeted Meryl warmly, and stepped up to hug her friend...but Meryl faltered. There was something stuck to her back, near her—

She grabbed at something that was caught just above her thighs, her eyes widening as she felt a...hook? A hook that seemed to have pierced a stretchy bit of fabric—a waistband? But not her skirt's, it was lighter than that, thinner. It felt like...

Her panties! She went to warn Kayla of what she'd discovered, but before she could, she was yanked suddenly up and off her feet, borne aloft quite literally by the seat of her pants. Meryl shrieked as she was whisked upwards, travelling up the flag pole in a matter of seconds while being subjected to the most horrific wedgie.

*

Now

Meryl held on for dear life in that awkward, backwards pose with her arms pinned behind her back, and her legs tucked round the pole along with them. The fall made her skirt fly up around her, and she soon felt a chafing...behind. Her face screwed up, the expression clearly pained as her undefended buttocks grinded against the pole's metal surface. Below, Kayla's mouth fell open in shock as she watched her friend rocket toward the ground, tastefully trimmed fanny fully on display for half the campus, undies slowly, very slowly fluttering to the ground in two torn halves far behind her. If she'd seen what was happening to Meryl's rear end, she might have made a sympathetic face while sucking in air through her teeth. The rubbing was, needless to say, quite intense. Meryl's poor posterior had been through a fair bit already, and now it was being subjected to intense friction as she slid back-first down the long, metal pole, quickly reddening during the journey down. Meryl's eyes were watering, her hair flying all about her face, the whole thing was so disorienting any notion of covering her pussy was out the window. For once, she was in blissful ignorance that her pussy was uncovered at all, so singular was her focus on the ordeal her arse was being **** to endure. She felt her calves starting to tire, and shifted her legs a little to try and preserve their strength, unknowingly causing her labia to open a little, a strip of pink within contrasting starkly against her skin as the folds of her inner labia became visible.

"Holy shit!" Kayla exclaimed, placing her hands over her mouth. Did Meryl even know what she was doing? Was she aware she'd just made things worse, spreading her pussy lips wide enough to give any stray observer a good look at what lay inside?

Meryl had almost reached the end, her arse by now resembling that of a baboon's more than its usual pale, caucasian hue, with its delicate flecks of rosy pink. Below her waist, she finally felt her legs give out, coming away from the pole and causing her lower half to swing forward, her legs spreading wide. Between them, most of her genitalia was visible, that strip of pink had become impossibly, luridly vivid, widening into an oval-shaped gap within which the innermost cavity of her vagina was incredibly eye-catching. Reaching the bottom of the pole, she landed hard on her arse, bouncing forward, squeezing her eyes shut and crying out as pain washed over her buttocks, legs still spread to their widest possible extent, her skirt tangled and wrapped up around her waist.

Meryl sat there, her buns sizzling, and her mouth hanging open in shock. Then, in slow stages, the reality of what she'd just been through fully hit her. She blinked twice, then opened her mouth and, in a loud voice that echoed throughout the campus, bawled "KAYLAAAAA! IT...IT HURTS!" Her tone was pitiable, almost childlike. Kayla was snapped out of her stupour by Meryl's cries for help, and she rushed over to her, hushing and cooing her as she crouched down to help her, trying first to get her to close her legs, then resorting to dragging her up and away from the slowly-gathering crowd before they caught too good a look at Meryl's face.