Tricking the Cheerleader

Despite references to high school, all characters involved are in their final year and are aged at least 18 or over. This story contains some questionable elements of consent. If you are uncomfortable with the idea of a gullible person being tricked into sexual acts, then do not read this story. Otherwise, enjoy.

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Colin Pinkitt knew that this was a bad idea, but he had always been a bad-idea kind of guy. He quickly looked around to check that nobody was watching, and then swiftly entered the women's changing rooms.

Colin cursed his so called 'friends' for putting him up to this. All over a stupid bet he had lost. Colin had tried to reason with them, but Fred and Seb were not in the mood to be reasoned with and wanted some lunch-time entertainment. So, here Colin was, attempting to steal clothing from the girl's lockers. Preferably a piece of their underwear. Colin cursed this stupid school and everyone in it.

Yet, that was simply the way of life in Foxtown High.

The request for a girl's panties seemed immature, but that was Colin's friend group for you. They referred to themselves as unique intellectuals, but to the rest of the class they were commonly regarded as nerds and losers; The very bottom of the social pecking order. They had little to no contact with girls and were undisputedly virgins (and probably would remain that way long after their school days were over). Thus, they relied on small, perverted activities to sate their hormonal lust. Upskirt photos, 'accidental' brushes against passing girls and, you guessed it, stealing underwear. They were deviants, but they didn't care. The way they saw it, society had made them this way, the same way it had made jocks, popular kids, cheerleaders, hipsters, goths and the entire social hierarchy across all schools everywhere. Foxtown High truly was sin and debauchery incarnate, and they were merely playing their part.

Colin wasn't concerned with the social hierarchy right now though. He had an important mission. Operation: Find and Retrieve Panties.

The changing room was separated into two sections separated by a wall which ran the length of most of the room. On one side was the lockers and on the other the showers. He ignored the hot, damp area of the showers and began to search the floor and around the benches next to the lockers. He figured it was better to check there before he started breaking into lockers and increasing the severity of his crime.

Colin felt more and more uneasy with each passing second. He knew what he was doing was wrong, but he wasn't troubled by any kind of moral compass, he was simply terrified of being caught. He had timed his entrance well, having waited for the cheerleading squad to finish showering after practise before attempting to sneak in, so he should have plenty of time before anyone would need the changing rooms again. Still, every footstep he heard in the outside hall sent shivers down his spine. He was not a big guy, 5-foot and 2 inches the last time last he checked, and he was not intimidating-looking in the slightest. Apart from the small mop of messy hair on his head he was completely hairless, with a feminine face, slender body and little to no muscle definition (he was really hoping the tail end of puberty would hit him like a truck). He would likely not be able to defend himself, even against a girl, especially not a group of angry girls. Not to mention the incredible trouble he'd be in when the teachers found out. Or even worse, Coach Kelly.

Coach Kelly was the head of physical education at Foxtown High and she supervised the school's cheer squad. She loved her precious cheerleaders and her favouritism was very clear. Some of the best and sluttiest cheerleaders were often kept behind for special one-on-one 'practice sessions' with the coach. However, she hated everyone else in the school. Not only was she known for her strict training regiment for gym class, many also feared her famously cruel punishments for rule-breakers. Quite a few students had gone to her office to be 'punished' and had their asses spanked so bad they couldn't sit down in class for weeks. Rumour had it that she kept two strap-on dildos in her office, a gentle pink vibrating one for her cheerleading lesbian lovers and bigger, more vicious, studded black one to punish the naughtiest students.

Colin's ass clenched at the thought. He hadn't found anything yet, and decided he had to try the lockers. He couldn't risk being caught and he simply had to move quick. The sooner he violated some girl's privacy and stole her precious undies, the sooner he could save his own hide and escape to the relative safety of the rest of the school. Despite always considering himself a 'nice guy', it was a wonder Colin never reflected on this questionable assessment when thoughts such as these entered his head.

He started on the lockers at the far end of the room. He immediately started to find cheerleader's uniforms. Made sense, this was their locker room and they had just come in from practise. The thought that many of the young, nubile bodies of the Foxtown High Cheer Squad had occupied these skimpy uniforms mere moments ago gave Colin a perverted sense of pleasure.

No! Focus, Colin. You're on an important mission with a strict time limit. This was not the time for your sick urges to make an appearance. You could jerk off to this moment later.

He continued through the lockers with no luck, until he reached one with no cheerleader uniform in it. He recognised the pink backpack inside it though. This was the locker of head cheerleader Daisy Docherty.

Oh, Daisy. Every teenage boy's sweetheart crush and lusty wet dream all rolled into one. She was a beautiful paradox. She was the most innocent girl-next-door type, her grades weren't the best but with sports she was a little overachiever, being proficient in various extra-curricular activities such as swimming, gymnastics and tennis and rising to the top in her favourite, varsity cheerleading. She was the nicest, most polite person to anyone she spoke to, and despite her trusting nature and complete disregard for the social politics of Foxtown High she was rather popular. She was currently dating Johnny Strong, the quarterback of the Foxtown High football team, and by all accounts she seemed like the perfect pretty girl, sweet and innocent in every way.

On the other hand, she was the hottest little sex kitten you'd ever fucking seen. She was gorgeous, with beach-blonde hair and a slim but toned form complimented by a miraculous set of D cup breasts and bubbliest butt to ever exist. When she wasn't wearing her trademark cheerleader's uniform, she was still showing off skin without even trying as none of her tops could seem to contain her big boobs and none of her skirts could properly cover her heart-shaped ass. Her look, her actions, her voice, all of it simply oozed sex without her even trying, even her simplest actions such as sucking on a lollipop with her big pink lips were enough to send guys into a horny frenzy. Every straight boy in the school had jerked off to her, and most had fallen in love with her. The cherry on the cake was that she seemed entirely innocent and unaware of her extremely powerful sexual appeal, leaving the boys of Foxtown High to helplessly wonder as to whether she really was the image of the pure virginity, or whether she was secretly a complete nymphomaniac. Rumours surrounded her, but nobody had anything concrete. Even Coach Kelly, who had deemed Daisy one of her 'top girls', hadn't seemed to get to her yet.

Colin had rubbed out many an orgasm over sweet Daisy the cheerleader, and his cock stiffened in his pants a little as her locker reminded him of her insanely fuckable energy.

Hang on, this didn't make any sense. As far as Colin could tell, cheerleading practise was over. Everyone else's uniforms were in their lockers. Why was Daisy's empty? Unless she hadn't been to the changing rooms yet, and was still...

Oh fuck!

"Erm, excuse me?" The soft voice came from behind him.

Colin tried his best to fight the paralysing fear that had struck him and slowly turned his head to the sound of the voice.

There she was. Daisy Docherty, in the flesh. She stood at the entrance, dressed in her painfully sexy cheerleading outfit which was skin-tight and barely covered her impressive tits and ass. Any of her tan skin left bare was covered with a thin layer of sweat, her brilliant beach blonde hair was plastered around her shoulders in a cute kind of way and her hefty chest rose and fell as she breathed quickly. She had clearly finished her cheerleading practise and had just returned to the changing rooms. So why hadn't she come with everyone else?

Colin had to stop himself from ogling Daisy's pristine body. This was very bad. He'd been caught red-handed in the women's changing rooms by none other than the head cheerleader. He could picture Coach Kelly's evil grin as she lubed up her Weapon Of Ass Destruction for his punishment.

"Umm, this is odd." Daisy tilted her head to the side in confusion. "This is definitely the women's changing rooms, the one sacred place of privacy a woman has in this school, but you're a boy. What are you doing here?" It hurt even more than Daisy didn't seem to be sarcastic, she genuinely couldn't comprehend the perverted nature of Colin's situation.

"Uhh... erm... Well, you see...Err..." Colin stammered. He was a tongue-tied mess. He was completely cornered with no logical explanation for his actions and was simultaneously breathless from being in such close proximity to Daisy, who had been the subject of so many of his sordid masturbation fantasies. Now here she was, not only near him but talking to him as well. This was crazy! Admittedly, not under the best circumstances, but Colin had to take what he could get.

More importantly, what on earth was Colin going to do? Part of him wanted to spill his guts, tell all of the horrible truth to Daisy and hope she would find some shred of sympathy for him. Maybe she wouldn't even report him to Coach Kelly? No, Daisy was too much of a goodie two-shoes, she simply had to abide by the rules. He might as well walk into Kelly's office and bend over for her at that point. Without a doubt, telling the truth was to sign his own death warrant.

So, the only other option was to lie. But what kind of crazy lie could he tell that would excuse this kind of behaviour?

Daisy was looking at him expectantly, waiting for his ironclad argument as to why he was trespassing in the room where the girls of Foxtown High were often found naked. He needed to think of something quick, her blue eyes seemed to be staring into his soul. God, her eyes were so beautiful...

Colin took a deep breath. Here goes nothing.

"God, Daisy, I guess Coach Kelly didn't tell you..." He tried to flash a nonchalant smile, but instead he gave a somewhat creepy grin. "I'm Colin. I'm here to collect the... uh, the uniforms. Yep, all the cheer uniforms, for the um... the wash. Laundry. Laundry wash, all the uniforms... me. Yep."

Fucking hell. Colin let out a deep sigh. He couldn't have sounded any more unconvincing if he had tried.

Daisy processed this information and seemed to take a little while to assess it. With every second of silence that passed between them, Colin's heart sunk a little lower. School life as he knew it was about to come to an end. He had never had much dignity to begin with, but for the rest of his time at Foxtown High he would be branded as a pervert as well as a loser.

Colin was mere seconds away from dropping to his knees, apologising for his lie and begging for mercy when Daisy responded.

"Oh, of course. Thanks, Colin, sorry for asking!" She giggled and returned to her usual bubbly self, practically bounding away from the door.

Huh? Colin must have misheard. Had she actually... bought that ridiculous lie? Daisy walked right up to him and Colin could smell her intoxicating perfume. Or was that just her natural scent?

"You'll have to forgive me, Colin. I was so confused. Coach Kelly normally does it herself, but obviously she's very busy, so this makes sense. Also, I'd never seen you before, so I was a little alarmed to see you by the girl's lockers." Daisy pushed her messy hair behind her ears. "So, are you new here, then?"

Colin could not believe what he was hearing. He felt a little bad that Daisy was gullible enough to believe his crazy story, but he mostly just felt relieved that his lie had worked. It likely wouldn't even have been considered by anybody with even an iota more cynicism than Daisy. He was a little hurt that she didn't know who he was, considering he was ready to worship the ground she walked on if she asked, but he couldn't blame her. He was a nobody after all.

"Sure, I guess you could say I'm new." Colin didn't want her to feel bad for not knowing him, but there was still one thing he wanted to know. "I tried my best to avoid you girls, I'm not a pervert or anything so I obviously wouldn't want to accidentally walk in on anything, erm, like that.' It was a white lie. Colin had hoped to avoid them, but not for the noble reasons he suggested.

"Aww, you're such a gentleman, Colin." Daisy smiled at Colin like he was a cute dog. He felt a little emasculated, but Daisy's immaculate smile sent him blushing nonetheless.

"Erm, well, perhaps but... why are you here? I waited for the cheer squad to leave after practise so I wouldn't be caugh- erm, catching any of you unawares."

"Oh, I was just helping Coach Kelly pack everything away from cheer practise." Daisy lightly pushed past him to her locker and started reaching around in her backpack. "Responsibilities of being head cheerleader, I guess. You know, Coach Kelly is so nice! She kept telling me how much potential I had, and even offered to give me private one-on-one tutoring every weekend. I don't know how one-on-one cheerleading practise would even work, but Coach Kelly must know what she's doing. She said we wouldn't even have to leave her office!" Daisy eventually pulled her phone out of the bag and unlocked it to hundreds of notifications. She was a very popular girl after all.

Colin sighed. There had been no way to predict her staying behind to help pack away. He figured that he must be the unluckiest guy ever. Which was a weird thought to have considering the lie he had just gotten away with.

"You've joined Foxtown High at such an interesting time, Colin." Daisy practically skipped up and down the changing room while she checked through her phone. "I mean, there's always something bizarre going on, that's kind of our thing. But get this, our school's star line-backer has just been accused of taking steroids! God, isn't that crazy? I never really spoke much to Adam, but Johnny knows him quite well and he said..."

Cute as she was pacing up and down, Colin wasn't listening. He was trying to assess the situation. He was currently alone in the girl's changing rooms with Daisy Docherty. He had, against all odds, successfully disguised his true intentions. So, what was his next step? Every logical instinct in his body screamed to mumble any kind of excuse and make a hasty exit. Daisy wouldn't question it and to wait any longer was only creating further risks.

But he stopped for a minute and considered this. Daisy really wouldn't question it. It's not like she wasn't smart, she had decent enough grades from what he could tell. However, in order for Colin to get away with his previous lie, it only stood to reason that she must be incredibly gullible. Not dumb, just extremely trusting of others and whatever they say. The concept of lying might not even exist in her innocent mind. It was kind of beautiful really.

So of course, Colin tried to think of how he could exploit it. There was a small chance that he might not only be able to escape, but also accomplish his mission. He might not be able to get any underwear, but surely the freshly used skimpy cheerleader's uniform of the one and only Daisy Docherty would be a sufficient substitute for his deviant friends?

It was a big risk, but Colin banked on Daisy's cluelessness.

He interrupted her rambling. "Erm, Daisy?"

"Huh?" Daisy stopped dead in her tracks and looked up at Colin with a vacant expression, her mouth just a little bit ajar. Somehow, she even made that look sexy.

"I, er, do hate to be so bold but as you know I was sent here to collect all the cheer uniforms. Yet, errm... I can't help but notice that you are still wearing... said uniform." Colin hoped this would be enough for her to get the idea.

He was wrong. "Ok... so, wait, what do you need from me?" Daisy set her phone down as she tried to figure out what Colin wanted.

Colin shifted uncomfortably. He was going to have to spell it out for her.

"Well, I need to to... take off your clothes, your uniform, I need you to... strip for me. So that I can take your clothes to be washed." Strip for me? Strip for me! Why had he used such pervy language?

Once again, he watched her confused expression as she processed this information, praying that she would believe him. She slowly looked at him, then down at her body. Had she clocked on to what he was trying to do?

"Oh, Duh!" Daisy laughed a pure, innocent laugh. "Silly me! You can't exactly take my uniform while I'm still wearing it, can you? I'm so sorry, Colin. You'll have to forgive me, sometimes I have no common sense! Of course, I'll take my clothes off for you now."

Holy shit! He had actually done it! Mission fucking accomplished! There was no way that Fred and Seb could complain about this prize he had scored. All he had to do was play along.

"Brilliant!" said Colin, perhaps with a bit too much enthusiasm. "Right, I'll just err, give you some space and-"

Daisy dismissively laughed Colin off. "Don't be silly, Colin. No need to be shy." She shot him a quick smile, then started to peel her skin-tight uniform off of her slim body. First the top, then the shorts. Before Colin knew what was happening, Daisy was standing before him having stripped herself down to her white, lacy bra and panties.

Oh. My. God. Colin could not believe his eyes, but they weren't lying to him. They were looking at the nearly naked body of Daisy Docherty. Good God, she could have been modelling that underwear. She was athletic and toned, but her skin still looked soft and tan. He looked at her breasts, desperately straining to be free from her bra, the hourglass figure of her stomach, and the long shapely legs. Her body screamed that she was sex personified, but the fact that she was wearing white underwear only further served to support the image of her as a vessel of pure innocence.

Colin was just beginning to think that he should commit as much of this to memory as possible, as this might be the best look he would ever get at Daisy's hot body (Hell, maybe the best look he'd get at any girl's hot body), when he noticed her hands move to her back after leaving her cheer uniform on the bench. Was she fiddling with her bra straps?

"Wh-What are you doing?" Colin stammered.

"I'm going to change for a shower anyway, you might as well take my underwear." Daisy said nonchalantly. Before Colin could react, she had unclasped the straps, and her breasts fell free of her bra.

Colin had never seen something so perfect, not in his entire, sad life. Upon Daisy's now bare chest he could see the two most brilliant boobs he could ever have imagined. He was not a religious man, but Colin believed that these boobs must have been heaven-sent. He had never seen anything as good, not even in the many porno videos he watched and magazines he read. They were big, but not ridiculously so, and they were perky, with perfect pink nipples in their centres. Colin immediately felt an intense desire to worship and play with them, to kiss, lick and suck her pretty nipples. As far as he was concerned, these were the most perfect big boobs to ever exist, and he was getting to see them up close and personal.