Cheryl's Mishap

Cheryl's Mishap
By an unknown author

It all happened that fateful Friday evening.

With yet another typically stressful day at one of Singapore's top junior colleges, young 19-year old Cheryl had gone to the school's running track for a relaxing jog. It helped to clear her mind of all the things that worried her; from her boyfriend problems to her slipping grades, she needed an escape from it all. The only daughter of a wealthy local businessman who worked in the telecoms industry, she had lived a life of privilege, with the recent setbacks being the worst that she had ever experienced.

The run itself had been relatively uneventful. Six laps round the JC's regulation track had left her with a slight burning ache in her muscles; a good ache, the type that meant that indicated that you had gone through a solid exhaustive workout. As she walked away from the track, she stopped by the side to pick up her duffle bag and towel, using the latter to wipe a streak of sweat off her forehead as she walked towards the main building.

Cheryl's thirst diverted her to the canteen. The open-air place was mostly empty, with only a few students hanging around after the various CCAs held in the afternoon. Dropping her bag on a wooden bench near the side, she walked across the room to buy a chilled can of 100 Plus from the drinks auntie. She popped open the can and poured a stream of icy isotonic drink down her throat. It felt heavenly after the long run had left her throat feeling parched.

She returned to her table and sat down, slowly sipping away at her drink. Out of the corner of her eye, she noticed a trio of guys sitting at an adjacent table peering at her. Cheryl tugged at the collar of her sweat-soaked PE shirt, realising for the first time that it had been a bad idea to have worn a black sports bra underneath, for its outlines were quite apparent under the clinging white shirt. She felt uneasy, nervously tucking a few strands of her shoulder-length black hair behind her right ear as she hurriedly finished her drink.

In her days back in a local chinese girls school, she had been mildly embarrassed of her mildly endowed chest. She had hated the blue sleeveless dresses, for they had shown how underdeveloped she had been in her chest region. Sure, she had grown to a modestly average cup size since her secondary school days, but she had always been self conscious about it.

Now, with all the undue attention being paid to her by the guys at the other table, Cheryl wanted nothing more than to get away from the place. So she did, as she stuffed her wet towel into her bag, slinging over her shoulder as she got up and walked out. As she stepped into the JC building's concourse area, she peered nervously behind her to see if anybody was following. To her relief, she was alone as she walked to the toilet near the recessed seating area in the middle of the concourse to change out of her PE gear.

The girls toilet was old, but clean and empty of people. The school's administration had not bothered to renovate it, seeing as how the JC was moving to newer premises in Bishan in two years. She laid her bag down on the floor as she unzipped it to pull out her change of clothes - a dark blue spaghetti strap top, a pair of jeans shorts and a beige bra and panties set. Cheryl walked over to the sink, splashing the cool water over her face. She looked at herself in the mirror, taking a moment to admire her reflected image. Her face was still tinged with a hint of red from the earlier exertion, but it did nothing to mar her looks. She wasn't that tall; standing about 1.65m. High cheekbones and doe-like black eyes drew attention from the boys in school, but her slim figure and tanned skin - all from months of wakeboarding - made her the complete package.

Abruptly, she noticed a face appear in the mirror. The door had been wedged open by the cleaning lady, so she hadn't noticed anybody entering the room till then. She assumed it was another student till she took a closer look and recognised one of the guys from the canteen. In fact, it wasn't just him, for all three of his kakis had somehow found it in themselves to enter the female toilet. The guy in the lead she recognised vaguely as one of her boyfriend's classmates, a rugby player named Jonathan. Beside him was a tall, muscular guy who looked like he came from the basketball team, while the third was a plumpish guy with thick-rimmed glasses. In fact, had he not been in that situation, she would have laughed him off as one of the poor nerds she kept turning away.

Jonathan looked up at the tall guy with a wicked smile on his face and nodded towards her.

"Come on Wei, she's ours," Jonathan said as the two strode quickly to her.

At that point, Cheryl was completely taken aback by their appearance to do anything other than open her mouth and scream for help. But her cry for help was cut short as Wei slapped her across the face before Jonathan took a filthy rag from his pocket - probably used to clean up the classrooms - and jammed it straight into her mouth. Before she could even reach to remove the makeshift gag, Jonathan had grabbed hold of her wrists and twisted her arms behind her back in a modified wrestling hold.

"Kai, pass Wei the string," commanded Jon as he pushed her down against the cold tile floor, using the sheer strength of his arm muscles to keep her from freeing her arms as she struggled to break free. The bookworm-lookalike handed Wei the ball of raffia that he'd been holding before standing back as the tall boy reached down to bind Cheryl's wrists together in a dead knot. No matter how hard she tried to scream, her efforts came out as nothing more than muffled grunts as her arms were tied behind her back.

When Wei was done with the raffia, Jonathan finally let go of her arms while using his knees to pin her legs to the floor. Cheryl flailed her bound arms, twisting wildly as she fought to be let loose. Wei reached over and flipped her onto her back while Jon grabbed her legs to prevent her from kicking or getting up.

Cheryl had known what they were planning to do right from the moment the three had stepped into the bathroom. In the canteen, they had been admiring her taut body from afar and now they were intent on getting their grubby hands on it. Wei took over the duty of holding her legs down as Jonathan stepped over to squat beside her.

"If it isn't our dear Cheryl stuck in a bit of a problem," grinned Jon as he ran a hand down the side of her face, caressing her right cheek. "You know, I've always wondered what fun Kenneth had with you, and I'm about to find out for myself."

As he reached down to her waist to pull her shirt up, she squirmed even harder in anticipation of what was coming. While she had had intimate moments with her boyfriend, they had not gone beyond heavy petting and kissing; her virginity was something that she'd been keeping for marriage. Now, a bunch of ruffians would take that away from her against her will.

But her muffled cries landed on deaf ears as Jon delicately pulled the damp cotton shirt to her chin, revealing the sports bra that had drawn their attention earlier on. He reached below her struggling body in an attempt to unlock the clasp in the back, but was unable to do so as she thrashed about on the floor. Giving up, he grabbed the thin fabric material and pulled hard, the clasp giving way with a loud snap as her modest mounds were revealed. Three pairs of male eyes were focused on her milky white breasts, topped by small pink nipples that were beginning to harden in the cool evening air.

Tears welled in her eyes as she watched Jonathan cup her breasts in his hands, massaging them like a cruel lover. The leader looked over at Kai and waved him over. The plump boy nervously reached for her mammaries, gently touching her left breast like a fragile toy.

"Oi! Forget about the breasts and go for the chee bai lar! If I want to see neh-neh-poks, I rather go to Geylang to see!" exclaimed Wei as he held her legs down.

"Come on Wei, there's plenty of time," uttered Jon, but he did let go of her breasts and reach towards her nether regions. Cheryl's struggles grew more and more intensely as he snagged the elastic waistband and pulled her PE shorts down around her ankles. The sports underpants were next to go, exposing Cheryl's tight cunt. She didn't believe in shaving all the hair off like some of her peers did, but she did trim it enough to leave a neat strip of pussy hair along her slit.

Cheryl bucked and threw her now-exposed body around in a vain attempt to break free of her tormentors' grasp. Her throat was raw from her attempts at screaming and tears flowed freely as she realised that the inevitable was coming to her.

In her struggles, she didn't notice the three boys pulling down their shorts to free their erections. When she looked up through teary eyes, she saw Kai stroking his dick as he admired her naked form.

The other two were a lot less subtle. Wei roughly grabbed her breasts despite his earlier disdain for her boobs, squeezing them tightly and pinching her nipples, sending jolts of intense pain (was there just a bit of pleasure?) through her chest as she muffled pleas through the gag.

Jon, undoubtedly the ringleader, was going to have the first go at her vagina. He positioned himself at her feet, sliding her pants off one foot in order to free her legs before forcing them apart. Cheryl cried out in terror as she fought to bring her knees together, but Jon was too strong and before long had placed his enormous dick at the entrance to her cunt.

"This is for all those months of teasing me, you little slut," sneered Jon as he slowly pushed the head of his dick into the folds of her pussy. The pain was nothing short of incredible and her eyes widened in sheer shock as he pushed against her intact hymen. With a grunt, Jon thrust himself into her, popping her cherry in a brutal fashion as his stiff battering ram broke down the walls to Cheryl's inner sanctum.

When he was about as far in as he could go, he pulled out of her completely before plunging his ramrod-stiff dick into her tight vagina over and over again. Cheryl wriggled desperately as she was violated by the rugby player, but she was powerless with her legs held open and her arms tied beneath her. The pain was so excruciating that she almost passed out, but something kept her mercilessly awake as Jon took great joy in savouring a tight, pristine cunt that he had fantasized about for so long.

The moments seemed to drag on forever as he pushed in and out of her virgin pussy. While the initial response of her body had been one of pain and shock, Cheryl found herself strangely stimulated by the sensation. It almost seemed as if her body had gone against her will and started to... enjoy. Perhaps it was her imagination, but she'd almost caught herself moving her hips in sync with Jon's thrusts.

But it couldn't be! She was being taken against her will, so she couldn't be enjoying it! Yet, wasn't there the saying "the body says yes but the mind says no"? Her mind started to drift...

She was shocked back into reality as Jon pulled back to the entrance of her pussy lips before pushing himself all the way into her in one violent motion. She heard him grunt twice as she felt his dick twitch; the only warning she got before she felt his warm sperm shoot up the entrance to her womb.

"NO!" thought Cheryl as she desperately tried to recall if she had had her period that month, but failed as she felt her own body respond to his ejaculation by squeezing her thighs even tighter, forcing more and more of his cum into the depths of her pussy. It was a reaction that she couldn't stop her body from performing, to her great dismay.

Jon pulled his softening dick out of her sopping wet cunt and knelt near her head, rubbing his cum-covered member against her soft cheek. Thankfully for her, she noticed that Kai had been unable to hold back, the floor below him covered with sticky semen as he put his dick back into his pants. Wei apparently had a similarly low threshold, for he gave his cock one last hard stroke before pushing it into Cheryl's face, unloading a stream of thick white jism onto her pretty face. The disgusting fluid mixed with her tears to form a wet, sticky mess on her face.

And that, apparently, marked the end of the session, for the boys rapidly put their pants back on and scampered from the bathroom, leaving her lying on the floor of the girls' toilet, her shirt pulled up, bra torn away and PE shorts hanging around her left ankle. Her pussy ached from the intrusion, a trickle of cum tinged with virgin blood dripping from her pussy lips. Yet she felt some sort of relief from the fact that only one of them had entered her that way; it could have been a lot worse had they taken their time with her one by one.

But as she laid there on the floor, she realized that she had felt aroused after the initial shock had worn off. Perhaps there was some part of her mind, buried deep behind in her unconsciousness, that had actually enjoyed the sex.

Eventually, Cheryl slipped out of her raffia handcuffs and took a shower. She never reported the incident to the authorities, partly out of shame, but also because the experience had awakened a sexual longing deep within her...