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The Cheerleader [F20/M53] [oral] [rough] [big tits] [age gap]
Author Summary
cringyexperience is in Age Gap
Post Body

Kylie’s footsteps echoed through the empty, granite-tiled corridors of Thompson Hall. With the exception of the Union and the Library, students typically wouldn’t be found in any of the campus buildings this late at night, especially after such a big football game. But Kylie’s situation was…different. Earlier in the day, Kylie and the rest of the Tech cheer squad were roaming campus, spreading spirit and hype throughout the mass of tailgates as they always do in anticipation of the big matchup against their biggest rival, State. As the festivities continued, the Tech girls eventually found themselves face to face with their equals from State, the captain of which was formerly Kylie’s high school bestie, Taylor. It didn’t take long for the formalities to give way to shit-talking, with Kylie and Taylor being the main perpetrators. Eventually Taylor upped the stakes.

“Wanna bet?” She asked. “Absolutely. Tech wins big tonight. And when we do, you and have to run a naked lap around the freshman dorm.” Kylie retorted. “Okay, and if State wins?” Taylor said, crossing her arms. Kylie gave it some thought for a moment. Of course she didn’t want to incriminate herself too much, but if she really expected Taylor to embarrass herself like that, then she knew she would have to offer up something spicy as well. “If State somehow wins, then I’ll sneak into the business school and get copies of the midterm for the marketing class” Kylie offered. It was definitely a tall order. Professor Michaels’ marketing exams were considered some of the toughest in the business school. Procuring copies would mean a major shakeup for many students that would otherwise fail. Taylor eventually agreed that it was a worthwhile bet, and with both of their teams watching, they shook hands and went their separate ways.

The game was a bloodbath. Not even 10 minutes in, Tech’s starting QB took a massive hit and had to be carted off the field. Then in the second quarter, their star wide receiver suffered a concussion and had to be benched as well. Kylie watched from the sidelines in disbelief as the clock ran to zero and cemented State’s massive win.

….which leads her back to now, wandering the halls in an empty school building. Taylor and her cohorts didn’t even give Kylie the chance to change out of her cheer uniform. Normally, aside from the current circumstances, Kylie took any opportunity to don her uniform, and her confidence wasn’t misplaced. She looked fucking hot in it. The skirt was bright red with black trim. It barely reached the halfway point of her thighs, showing off her long, toned legs. Its pleated stitch caused it to bounce playfully with each step, constantly coming tantalizing close to revealing just a little too much. The top was a cropped, long-sleeved, dri fit style. The white, red, and black fabric fit snuggly to her torso, highlighting her remarkable chest, despite her wearing her best sports bra. Her long, dirty blonde hair was pulled into a tight high ponytail that seemed to dance around as she walked. Her white sneakers causing the occasional squeak in the pristine floors.

She finally rounded the corner to the professors’ offices, and spotted Professor Michaels’ door. As she neared the old wooden and glass door, she was topped dead in her tracks by sounds coming from another office a few doors down. As her eyes adjusted to the darker hallway, she made out the outline of a custodial cart parked outside of another door. Just a janitor, gotta be quick. she thought. She slowly opened the door to the office and made her way over to the desk. Fortunately, by some stroke of luck, her target lay right there on top of the desk: copies of the upcoming marketing midterm. She quickly pulled out her phone and prepared to snap her pictures, when suddenly, the lights to the office illuminated. Startled, Kylie let out a yelp and looked up to see a stocky man in a dirty, dark blue uniform staring angrily at her.

“The fuck are you doing in here? This is a private office.” He said, his scratchy voice booming in the quiet room.

Kylie stammered awkwardly as she tried to explain herself. As she struggled, the janitor looked down and noticed the tests laid out, and the phone in her hand. He let out an annoyed sigh.

“Alright girl, I see what’s going on here. Unfortunately I’m gonna have to call campus security.” He said as he fished out his old flip phone.

Kylie began to panic. She could be expelled for this. She would certainly be kicked off the cheer squad, which would likely mean she’d lose all her scholarships, her life here at Tech would effectively be over.

“Oh no, please don’t! I’m so sorry it was just a stupid dare! Please is there any way you could just let me off with like a warning or something! Here, look I’ll even show you me deleting the pictures!” Kylie begged, genuinely terrified of the repercussions.

The janitor paused, looked down at his phone, and looked back at Kylie. As his eyes lingered on her for an extended time, she suddenly became aware of just how much her cheer uniform didn’t cover. The janitor’s gaze appeared to move from her face down to her body, hesitating a second longer on her chest. The janitor closed his old phone and slid it back into his pocket. He closed the door behind and stepped forward as he began to speak.

“Well uh, I’m sure there’s something you could do for me that could convince me not to rat.” He said with a wink.

Kylie tried to hide her secondhand embarrassment at the man’s attempt at being suave, especially given the situation. She knew what the man was implying, and her mind began to race trying to think of a way out of this.

Still holding her phone, Kylie pulled out her Photos app and scrolled to a rather suggestive section. “I um, I have these pictures that I think you’d like.” She suggested.

The man took another step closer to her. “I’m sure they’re lovely. But I was thinking of something a little more…physical.”

Kylie again scrambled to think of something else. Before she could, she found herself face to face with the old janitor. He had stopped just a couple inches in front of her, his eyes traveling downward and locking onto her breasts. Kylie stood there frozen as the man’s cold hands made contact with her sides, sending a shiver down her spine. His grip moved up until his fingers began to hook under her top. He pulled up, having to shimmy a bit as he pulled the hem over her massive mounds. After stopping just below her neckline, he then began pulling up on her sports bra. The janitor seemed to do so in an intentionally slow manner, allowing each of her tits to pop out dramatically. He was instantly grinning at the sight of her incredible breasts, like a 12 year old boy seeing them for the first time. Immediately his hands went to work exploring them, massaging and kneading, grunting in excitement

“Ahh god damn. How big are these puppies?” He asked in a hushed tone. “Um. Th-thirty-two G” Kylie responded. “Fuckin hell, these are great tits.” The janitor exclaimed as he continued to manhandle them.

After a few more minutes, he let go. Kylie, thinking he was satisfied, began to reach for her top hoping to put it back into place. He spoke before she could, “take it off all the way”. Kylie sighed again before removing her shirt and bra entirely. The janitor stepped back to take in the sight of her standing there with nothing but her cheer skirt and sneakers left on. Her bare tits on full display, her small nipples hardened from his hands and the cool air in the office. He stepped back in closer, placing his hands on her shoulders, pushing down.

“On your knees baby.” He commanded.

After resisting a moment, Kylie gave in and sank to the floor, her bare knees making a light thud against the cold tile. The janitor began fumbling with his belt and trousers, eventually shaking them to his ankles. Kylie found herself now face to face with his bulging tighty whities, the smell of his musk starting to lightly penetrate her nostrils.

“Pull it out” he barked.

Kylie gingerly reached up to the elastic waistband of his underwear and began to pull. His rock hard cock finally sprung free, seemingly staring her directly in the face, a small head of precum already waiting. She had little time to prepare herself, as she suddenly felt his hand on the back of her head. With his free hand, he gripped the base of his cock and began guiding the two together. The rounded tip of his dick made contact with her plump lips, parting them and allowing him to fully enter her mouth. He grunted with pleasure as he began to bob her head back and forth on his cock. He gradually released his hand from the back of her head, allowing her to take over. Kylie was no stranger to sucking dick, her ex-boyfriend often said she was one of the best he had ever had. She maintained the same rhythm the janitor had started with, hoping to finish him off quickly and get this whole mess over with.

“Ahh yeah you’re a good little cocksucker aren’t you?” The man said under his breath.

He let her nurse his erection a few minutes more, before he decided it was time for a change of pace. Kylie once again felt his grip on the back of her head as he wrapped his hand around the base of her ponytail. She was caught off guard though when he forcibly pushed her head into his pelvis, ramming his cock into the back of her throat. Kylie gagged loudly and clinched his thighs as he held her there. The man pulled her off slightly allowing her to briefly recompose herself, before promptly pushing his cock back into her. Kylie gagged once more as his pushed himself as far as she could take, only this time instead of pulling her off, he continued to push. The busty cheerleader gagged and croaked once more as his hard cock finally slid into her throat. The janitor let out a low guttural groan as her throat convulsed and constricted around his member.

Kylie did her best to keep it together, trying to control what little breathing she had, resisting the urge to vomit as he held himself deep inside her throat. The man’s finally began to pull himself out, but not before immediately ramming himself back once more. He repeated this again, and again, and again, with increasing pace. The normally quiet professorial office, where students often came to ask questions about their failing grades, was now filled with the sounds of a hearty throatfucking. And ear pressed to the door would yield a repetitive wet “gluck gluck” sound, percolated by the janitor’s grunts of bliss and the occasional whimper from Kylie.

As he wildly continued bucking his hips and yanking Kylie’s head around in unison, the janitor craned his neck to side in an attempt to admire his work. The sight of this blonde, big-titted college cheerleader throating his cock was the stuff of pornos. Her massive tits, covered in the saliva that cascaded off her chin, bounced wildly with each thrust. I’m that moment the janitor knew that he was about to blow a load bigger than he had ever experienced. With a few more thrusts and a Herculean grunt, he was finally there. He slammed Kylie’s head into his pelvis, his cock thrust as deep as physically possible as he exploded into her throat. Rope after rope of hot cum had nowhere to go but down, as Kylie did her best to swallow all of it.

After holding her there a few more moments, the janitor finally released his grip, Kylie shot off his cock, sucking in air as if she had been underwater for far too long. The janitor stumbled backwards and leaned against a nearby chair. The duo sat there for a moment, both catching their breath. Finally, the janitor spoke up.

“I didn’t see nothin’”.

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3 days ago