Making The Grade

"Happens to be the best of us. I've forgotten how many trips to the pharmacist I've had to make to get a morning after pill," Marissa took a step back and stared up and down at her friend, double checking that nothing had been missed. "I think that's everything. I know this isn't the best time to say it, but you look pretty hot. When this is all over, you should consider making this look permanent."

"I wouldn't count on it," Lucy decided to peek at the hall beyond, seeing the shadow dancing under around under the door crack. "This is it then, no turning back now."

"Just don't worry, I'll be waiting right here until it's over," Marissa reassured her, watching Lucy inch herself towards the corner turn, taking staggered breaths as she urged her legs to move. "Keep your head high and don't let him see your fear."

Lucy felt her legs turn to lead, refusing to shift in any way from the space of the hall she had rooted herself to. Closing her eyes, she finally sent one leg out in front of the other, uncomfortable with the sharp click the heel produced as it struck the floor. Like a fawn, she stumbled her way along the hall, resisting her natural urge to turn around and flee, aware that it was unlikely she would ever make it so far again. She walked with a nervous gait, wondering how likely it was that she would pass out before making it anywhere near her intended destination.

However, reminding herself about the reason for her presence there was enough motive to keep her moving, especially when thoughts of acceptance letters swirled in her mind. She kept going, focusing on each footstep that brought her one step closer to her destiny, turning only once to look back, finding Marissa giving her a somewhat encouraging thumbs up. Soon, there was nowhere else left to turn, with the brunette finding her eyes coming level with the taped-on plaque that had started to peel away from the worn wood, dangling from what little tape still clung on.

Lucy clutched her stomach, holding on tightly to her last nerve, dearly hoping it would hold together long enough for the deed to be done. Closing her eyes and holding in a breath, Lucy lifted her hand and brought it to the worn surface of the door, giving it a gentle tap with her knuckles. She jumped when she heard the clattering of objects inside, shortly followed by a few expletives as they came crashing down, hitting the floor with some force.

"Who the hell is it?" a heavy smoker's voice barked. "If this is about the lights in the auditorium not working it ain't my problem! Tell that cheapskate principal to fork out for an electrician, no way am I about to fuck around with a fuse box when it's on the fritz."

"I'm not here about that, Mr Barker," Lucy spoke up, making her voice sound far braver than she truly felt. "I just needed to ask you about something."

Lucy listened as the janitor hastily tried to pick up the objects scattering the ground, resorting to kicking them away as his heavy boots thudded up to the door. He pulled back a set of bolts and chains, throwing the door open quickly enough to create a brief gust that struck the incredibly nervous girl, sending a miasma of cheap tobacco towards her. Lucy stopped breathing for a short time, waiting for the corridor to suck out the pungent scent of tobacco from the room, unwilling to breathe in too much of the overpowering smoke.

Mr Barker stood in the doorway, surprised to find a student standing before him rather than one of the teachers he despised so much. His eyes blatantly travelled over Lucy's form, picking up every detail from her shortened pleated skirt to the heels shaping her already enticing figure. A disturbing grin stretched across his ugly face, displaying rows of teeth that had yellowed after years of chain-smoking and liquor drinking, staring unwaveringly at the beautiful face of the terrified cheerleader.

"Well, what do we have here? It's a bit late for you to still be hanging around this place, even the faculty bolted as soon as the bell rang, except for the pencil-necks that is," Mr Barker coughed into his fist, still not averting his gaze, unconcerned whether Lucy caught his eyes wandering. "So what are you doing here then, missy? Something you need?"

"Actually, there was something I needed to discuss with you," Lucy kept her voice as steady as achievable, conscious of the janitor turning his eyes to her cleavage, visibly impressed by the size of her bust. It was precisely the sort of behaviour she expected from a man who spent much of his time at the school leering at the seniors and cheerleaders. "Would it be alright if I could come in? I wouldn't want anyone eavesdropping on us."

"Sure, step into my humble abode," Mr Barker stepped to the side, but not enough to prevent Lucy from having to brush up against him as she swept inside, ensuring she felt his burgeoning hard-on as she passed by. "Make yourself at home. And don't mind the mess, I wasn't expecting visitors."

"Thank you," Lucy replied politely as one could when entering such a grubby den.

Lucy felt her heart stop for a split second when the door closed with a decisive slam, locking her in with the old man. But she remained calm, distracting herself by examining the expansive closet she found herself in. There was more space than she had envisioned, enough to be able to move around without bumping into the equipment and countless bottles of cleaning liquid stacked on the surrounding shelves. She took a deep breath in, immediately regretting it after being assaulted by a waft of nicotine and traces of chlorine fumes hovering in the air, stagnant due to the lack of windows or air recyclers.

Off to the corner, she found a pile of dirty laundry, mostly consisting of used overalls in need of through cleaning. They were bunched up in a pile beside an old cot, with a mattress that had become threadbare from years of consistent use. Above the cot were a number of provocative posters, each displaying a naked woman posing seductively for the benefit of the viewer. Lucy held back the urge to gag when she spotted a few balled up tissues within a nearby waste basket, leaving her in no doubt about what the owner of the posters used them for.

"Quite the place," Mr Barker grinned, punting a few rolls of toilet paper that had fallen, sending them flying into the cupboard storing the mops and brooms, many of which appeared in need of replacing. "My home away from home. Well, home away from my old lady."

"It's... charming," Lucy lied, disguising the lie behind a small smile. She searched for a place to stand that wasn't completely riddled with some form of grime or sickening stains, but discovered that there was little in the way of cleanliness in a room designed to create that very thing. "Do you sleep here often?"

"All the fucking time," Mr Barker cackled, shuffling over to a makeshift drinks cabinet. "That's the advantage of getting a gig at these private schools, they always keep themselves clean. All I have to do is mop a few floors and spray down the occasional window, then I have the rest of the day to do whatever I want."

"I see," Lucy watched him pour out a liberal amount of bourbon, not sparing a second before taking a large sip. "I always wondered why we've seen you so rarely around the school grounds."

"Do the least work you can and reap the benefits, that's what I say," Mr Barker smacked his lips, turning to face Lucy. "But enough about me. I want to know what a cheerleader like you could want with me? It's not everyday I get one of you beauties knocking at my door. Drink?"

"No thank you. As for my presence here, it's a rather delicate matter," Lucy stared down at the ground, thinking of the various ways she could broach the subject, trying to find the most tactful of the bunch. "I have recently become the recipient of a less than stellar grade, one with far reaching consequences. As it turns out, there's a way for me to alter it without anyone knowing. But to do so, I need the key to get into Mr Sheridan's office."

"Ahhh, I get it. You're looking for that," Mr Barker pointed at a small cork board mounted on the wall, covered with keys of varying shapes and sizes, bringing her attention to the chrome coated key hanging at the centre. "The skeleton key, that thing opens up just about every room in this place. Sheridan tried to get a custom lock put on his door, but I set him straight. So that's your ticket to forging yourself a new grade then?"

"Yes," Lucy answered meekly, rattled by the cunning glimmer that appeared in the eyes of the janitor. "There's no other way of accessing the office without alerting someone."

"Interesting," Mr Barker nodded slowly, swishing his drink around as he stared perversely at Lucy, emboldened by her inability to stop him. "I wouldn't have pegged you as the devious sort, you've got that innocent look about you. Good little plan, get in and out without that stuck up bastard Sheridan finding out. But that's only if you can do it without getting caught, because if you did you would have to explain where you got the key from. I've got a comfy set up here, I don't intend to lose it just to doa cheerleader a favour. What's my incentive?"

"I need to do this, I can't leave this school with that grade. Just name your price," Lucy tried to keep desperation from trickling into her voice, but it was a far harder task than she had anticipated.

"A blank cheque, eh?" Mr Barker licked his lips, taking long strides towards Lucy, still with his glass in hand. "Dangerous thing to give away, I could ask for anything. Do you have anything in particular in mind? Because the little touch ups to your uniform suggests you did."

"Just tell me what you want me to do," Lucy sighed, letting her shoulders slump.

"There are so many things I want to do with a sexy thing like you. Hey, I've got an idea!" Mr Barker tested Lucy's limits, bringing his hand to the side of her thigh, tracing his finger over the floral pattern of her stocking-top, raising the hem of her shortened skirt with his pinky finger. "Why don't you get on your knees and show me exactly how desperate you are to get your hands on that key?"

"Okay."

The singular word departed Lucy's lips as little more than a whisper, one that was barely audible. But the old janitor heard it as clearly as if she had screamed it at the top of her lungs, his eyes lit up as if all his greatest dream had come true at once. It took some time before Lucy could find the courage to move, still unsure whether she had the courage needed to debase herself. However, Mr Barker decided to speed up the process himself, grasping her narrow waist, applying enough pressure to cause her knees to buckle under her, sending her gradually sinking to the dirty ground.

"That's it," Mr Barker let go of her, satisfied to see her falling of her own accord, coming to rest on her knees at his feet. "You look perfect in that position, it's about time that one of you rich girls was humbled. Now, why don't you get those manicured nails to work getting my fly undone? My cock's aching for some relief."

Lucy blinked rapidly, still struggling to come to terms with the reality she found herself in. Her fingers shook as they rose up to the brass zip running down the groin area of the dirty overalls, jerking the tab down until both flaps were separated. Without warning, Mr Barker's member sprang from the void, almost smacking Lucy's face as it emerged. It was more substantial than Lucy had expected from the old man, reaching almost eight inches with a circumference thicker than anything the brunette had ever seen in person. The purple head pulsated mere inches from Lucy's lips, dribbling a slow flow of pre-cum.

"Surprised? What, did you think I was only packing a one-incher?" Mr Barker brushed his hand over his greasy comb comb, trying to keep his heart from beating out of his chest as he watched the cheerleader's eyes focus on his exposed organ. "I'm not one of those roided-up jocks you lot love to fawn over, I'm all natural. Tell you what, if you don't believe what you're seeing, then give it a little kiss."

Lucy reluctantly curled her nimble fingers around the thick shaft, only just able to get her hand across it fully. She could feel it beating against her palm, generating a heat that made it almost scorching hot, but not enough to make Lucy release it. As nervous as she was, Lucy found herself admiring the sheer power pulsing through the old janitor's cock, displaying a virility that dwarfed that of the boys she had fooled around with. It was an impressive appendage, attached to a less than impressive man.

Carefully, Lucy slid her hand along the length, shocked to find that it only became thicker as her fingers moved towards the base, bringing her attention to the pair of cum-laden testicles dangling beneath it. She pumped the cock slowly with her fist, hoping that she could at least familiarise herself with it before going any further. But the old janitor wasn't in the mood for simple foreplay, not wanting to waste his one opportunity to desecrate one of the famed beauties of St. Margo's.

"If I wanted to be jerked-off then I would have done it myself off to a picture of those lovely ladies behind me," Mr Barker gruffly interrupted Lucy's tentative stroking, impatiently pushing his manhood closer to her lips. "It'll take more than a handjob to get that key, rich girl."

Lucy brought her stroking to a halt, understanding that the man wouldn't be satisfied with being stroked to completion. Holding the quivering cock in one hand, Lucy moved in and guided the domed head to her soft lips, squeezing her eyes shut when the tangy pre-cum began to smear them. A few prods from the spongy head coaxed Lucy into separating her lips, an action that was immediately seized upon by the janitor when he drove his cock into her mouth, bumping it against the back of her throat.

"Hmmmffff!" Lucy's cry was muffled by the organ that threatened to clog her throat. Even just halfway down, it was buried deeper than she was comfortable with, forcing her to open her jaw as wide as it could go. She tried to push herself away, but she felt Mr Barker's hands land on the back of her head, grabbing her tousled hair to prevent her from breaking free.

"Jesus, I haven't been throated like this in years!" the janitor let his head fall back, groaning as Lucy's tongue involuntarily rubbed against the underside of his manhood. "I always knew you cheerleaders were a sordid bunch, no matter how innocent you all act. That's it, get that tongue working."

Lucy wondered if the old man would ever relent, or if he was intent on holding her in place until she passed out. He shifted around and tickled her throat, coming perilously close to slamming forth to send his member slithering down to the depths of her gullet. Fortunately, he retracted far enough to let her suck in a vital breath of barely fresh air, sending strings of saliva flooding down her chin and neck. The cheerleader blinked her watery eyes, still able to feel the top of the massive shaft balancing against her bottom lip. She sent a glare towards the gleeful janitor, but it wasn't enough to prevent him from forcing himself back into her mouth and pistoning it in and out without any regard for Lucy.

Knowing that it was unlikely that the old janitor would do anything to make things easier for her, Lucy forced herself to clear her mind and focus on her task. With her mouth wide open, she flattened her tongue and allowed him to glide along her tongue, relaxing her throat to make the process of exiting and entering a more fluid effort. A lack of experience put her on the back foot, but Lucy was just able to take the brutal attack, becoming little more than a toy for Mr Barker to thrash around.

"I've always dreamed of doing this. To tell you the truth, I've finished myself enough times this year with the image of you in my head," the janitor sped up, clumsily plunging into Lucy's sore mouth without any pause between thrusts. "I've seen you out on the field during those practice sessions, moving your tight body for everyone to enjoy. It's just as perfect as I hoped."

He continued to saw into Lucy's throat, moving until her muscles burned. Sure that she would pass out, Lucy was surprised to feel an abrupt vacancy in her mouth, enabling her to breathe without restriction. She dropped her head and fell on all fours, coughing harshly as she recovered. But her recovery was only short lived, and ended when Lucy felt herself being plucked from the ground and lifted into the arms of the burly janitor.

Her initial confusion was corroded when she watched the old man turn in the direction of his stained cot, shuffling as he carried her bridal style towards it. Lucy found herself dumped unceremoniously onto the bed, ending up flat on her stomach. She felt her skirt being shoved up to her hips, cringing when the sound of fabric being shredded marked the moment when her expensive thong was torn from her body, taking with it the last barrier between her sacred spot and the greasy janitor.

"What a beautiful pussy, the tightest I've ever seen. Hell, I might actually be convinced that you're still a virgin, but not for long," Mr Barker climbed onto his cot, barging Lucy's legs apart with his knees, massaging her stocking-clad thighs as he lowered into position. "I've been waiting decades for a moment like this, gettin' to bag me a cheerleader. Let's see if you can handle me."

"Wait!" Lucy finally found her voice, just when she could feel a pressure forming against her tight slit. She twisted her arm around, struggling with the limited space she had between her and the dirty mattress. Reaching into the breast pocket of her blouse, Lucy pinched one of the foil packets between her fingers, snapping her arm back to deliver it to janitor. "I haven't been on the pill in a few weeks. You have to wear this!"

"Seriously? You waited until the last second to tell me that?" Mr Barker grumbled, glaring hatefully at the foil as it shone in the dim light pouring from the single lightbulb illuminating the room. "It's not even an XL, you have to be stupid if you think this rubber is gonna fit."

"I don't care! Either you put it on or the deal's off!" Lucy replied firmly, glad to discover that she still had some sense of reason left in her.

"I preferred it when you were too full to speak," the janitor fiddled with the package, forced to tear the strip off with his teeth when he became too frustrated with the strength of the material. He finally pulled the condom free, hesitantly rolling the ring down his swollen member, watching as it stretched to its limit to accommodate his full size. It was an incredibly tight fit, but Mr Barker didn't care as long as could bury himself deep inside the beautiful cheerleader's tunnel. "There, it's wrapped up. Still don't get why I have to do it, you can get the morning after pill over the counter these days."

"I won't take the risk," Lucy stated, gripping the loose threads of the mattress when she again felt the old man propping his member up against her entrance, this time digging between her labia. "Just please be gentle."

"Little chance of that, sweetheart. This is prime pussy, and I'm going to enjoy it until it gives me a stroke!" the janitor dropped his weight and fell heavily onto Lucy, shoving his large organ into her sex in one go.

"Ahhhgg! Too deep! You're going too deep!" Lucy cried, burying her face in the grimy mattress to muffle her agonized screaming. Her legs kicked back, arching her feet to the point where her borrowed heels tumbled down to the dirty floor, but Mr Barker was quick to pin her legs back down with his knees.

"That's right, I'm all the way inside. Jesus, keep squeezing me like this and you might end up cutting off my blood flow," Mr Barker laughed cruelly, swirling his hips around to try and stretch Lucy's walls out. "So fucking good!"