The Janitor and the Cheerleader

"I shouldn't be doing this."

The thought kept bouncing around 18 year old high school senior Erin's head.

She knew she should stop thinking about him. It didn't make any sense at all. He was many levels beneath the type of guy she "should" want to be with.

She was arguably the prettiest girl in school. As the captain of the cheerleading squad, she was front and center at Park Prairie High School events.

Her radiant smile, long and thick brunette hair that danced all the way down her back, ample natural cleavage and ass were always a center of attention in the school's red, white and blue cheerleading outfits.

She should have wanted to continue dating her high school boyfriend. The one who took her virginity. But there was something so incredibly cliche about what they did after their junior year dance.

The pressure of not only being beautiful but also maintaining a high GPA for her demanding parents was also a factor in her liking someone she wasn't supposed to.

The plans made for her: to be beautiful, go to college, marry a successful young man, carry a career, and be at the top of whatever social structure she interacted with dragged on Erin.

She had grown to hate the pressure and feeling of her own elitism. Granted, it was high school but everyone in the school wanted to be around her. She set fashion trends and while she was nice to pretty much everyone there was still a requirement to be mean at times to those viewed as lesser than the ruling class of the school.

She contemplated all of the options in her head and she knew that involving herself with the guy she shouldn't like was a bad option on paper for a long list of reasons.

If it got out that she liked him...her life in high school would be ruined.

Her parents would disown her.

Her friends would absolve themselves from her.

Her social credibility would be zero.

Yet losing everything felt more freeing than anything.

That's what she loved about him.

How he took the overt scorn and disdain from students.

How he knew teachers and staff looked down on him and yet still did his work.

How his real world sensibility and sense of humor popped through what should have been a sad existence by other's standards.

The anxiousness she felt when she saw him in the last month was extreme. Her heart would skip a beat. She wore cute outfits even more often. She took a different route to her classes to walk by him. She made sure her hair was perfect everyday.

It was stupid but she couldn't help it.

She was in love with the school janitor.

Harvey, as his name tag on his uniform body proclaimed in red cursive writing, was the object of Erin's attention.

He was the personification of a school janitor. The 45 year old stood at just over six feet tall, had some thinning up top mixed in with some flecks of grey in his light brown hair. The dark brown eyes and wry smile he seemed to wear as a badge of honor were only matched with his wit and charm. He had a barrel chest upper body from years of working on plumbing problems, maintenance issues, and physical labor at the school.

The thing that did it for her though was how he seemed to never mind the silliness of the high school culture.

His janitorial office was located underneath the cafeteria, in the bowels of the basement of the school. The area was set apart from where any students bothered to go. The poorly lit hallway filled with random odds and ends from projects all over the school grounds were a seeming barrier he had erected to keep students and faculty out.

The office, and everything about it, was almost a magnet for her. She had asked around as conspicuously as possible and the answer was always generally the same that Harvey was a guy left best on his own to do whatever it was that a janitor was asked to do.

She had overheard a conversation between Harvey and a teacher a couple of days earlier where the teacher wished him a happy early birthday for the upcoming Friday. He thanked the teacher for the birthday wish and went on his way to his next task.

Erin filed away the date and spent the next couple of days thinking about what she was willing to do.

She had thought about Harvey a lot as her crush blossomed throughout the school year.

She had little pregnancy concern as she had been on the pill since she had been with her ex-boyfriend.

The high stakes gamble of just exploring what it would be like to take her high status place in high school and toss it at the feet of the arguably the least regarded man in the building was a desire that was too strong for her to overcome.

She knew the risks. That made it more fun.

She got up extra early on that Friday morning to make sure her dark brown, naturally curly hair had extra attention. She had gone to the store to buy pink lingerie for the day. The lacy bra and panties she wore hugged her body tightly.

The school dress code was always an annoyance but one she enjoyed maneuvering around. Up until that day, it was the closest she had ever gotten to rule breaking in her pristinely planned and executed life.

She picked her favorite school appropriate cream colored turtleneck. The sweater had thick material and was almost one size too small. While it did cover her entire chest, her natural D cup breasts were on prominent display with the push up bra she had on underneath.

Added was her favorite black pleated skirt.

The skirt ended just below the knee.

To be in compliance with school dress code rules, she wore black tights underneath the flirty skirt.

Two inch wedge heels completed the flirty ensemble.

She knew her plan. It was relatively simple but still felt dangerous.

Erin had acquired a birthday card. In it, she wrote the words, "I will be your birthday gift. Leave your door unlocked if you want to unwrap me in your office after school today. I will be waiting for you. Xoxo."

She kissed the card instead of writing her signature. Her soft pink lips gave a teasing hint as to who would be waiting for him.

She arrived early to school that day and calmly walked downstairs to the quiet hallway where Harvey's office was located.

She double checked to make sure no one was paying attention to where she was going. The dark corner of the school didn't even have any security cameras mounted as no one bothered to go there other than the janitor she had a massive crush on.

She nervously stepped into the janitor hallway and saw the old, heavy wooden door. The small sign on the door read "Janitorial."

Her heart was beating furiously in her chest. She looked under the door and saw there wasn't a light on inside. She very gently touched the door handle and tugged on it very slightly to find that the door was locked. She breathed a sigh of relief.

She removed the sealed envelope from her bag and stared at her gold glitter handwritten "Harvey."

She closed her eyes for a moment and resolved to go for it. Quickly, she slid the card under the door and scurried away from the door and hallway to go back upstairs into the general student population.

The next few hours were agony for Erin. She went back and forth on whether or not she would actually go through with it. She wanted to but the risk felt massive. What if someone saw her? What would she say? What if he didn't show up?

In between her classes, she scurried through the hallways to her next classroom. She didn't want to see him in the hallways in the worry that she would convince herself to not go down and offer herself to him.

She resolved as her last class before her lunch period at noon was to arrive that she simply needed to find out if all of the pressure she felt from her life could potentially be unwound by doing something that was so against the norm. The butterflies in her stomach were the kind of nerves she wanted to feel.

She had decided to go through with it.

The bell ending the period before noon rang and every student hurried themselves out of their classrooms.

Erin made her way to get lunch with her friends. She tried to act as normally as possible as the hustle and bustle of the busy lunch period overtook the cafeteria.

Her mind did wander to thoughts about the room just underneath the cafeteria, tucked away and hidden from plain sight. She wondered if he had read the card yet? If the door would be unlocked? If he would be waiting for her?

Her mind raced with what she would say? What would she do if it went wrong?

She snapped out of her train of thought as a friend chatted her up about her latest outfit.

Out of the corner of her eye, she noticed him standing at the far end of the cafeteria.

Her heart skipped a beat for multiple reasons.

She snuck a glance at him but was quite subconscious about the soft pink lipstick she was wearing matching the kiss signature she left on the card in his basement office.

She was sure he hadn't noticed her and was saved by the bell to exit the lunchroom and head to her next class.

The afternoon zoomed by as Erin continued to think about what she might do with Harvey.

All of her thoughts revolved around how much she wanted to hand over her stress and need to conform. He represented the most rebellious way that she could do that and the thought drove her wild with anticipation.

The final bell rang for the end of day and the hallways of the high school flooded with students making their quick escapes to head into the weekend.

Erin had told her Mom she was going to study and to not expect her home until later. Her Mom, ever demanding as ever, told her to take as much time as she needed.

Erin lingered at her locker and then made her way to the back end of the school where the lonely staircase went down to the quiet area where the janitor area was.

Each step down the old vinyl covered staircase made her feel the anticipation more.

Her pussy tingled with electricity.

She could feel her breathing get deeper as she swayed her hips slightly with each step as walked down the dark and dingy hallway to the door marked "Janitorial."

Erin knew she was in the process of leaving behind all of the expectations, pressure, and demands she and others had put on herself.

She had no idea what would happen with Harvey but she felt amazing that she was going to try.

She got in front of the large and thick old wooden door and touched the metal handle.

The door clicked open and she swung it open to reveal a work room. She reached over and turned on the light switch and confidently walked inside.

She turned and closed the door and locked the deadbolt.

The room had cinder block walls and a cold concrete floor that was partially covered with an old rug where the broad desk and chair sat.

A work bench sat on along a wall that had ample shelving filled with supplies needed for Harvey's work.

She took in the slightly dreary room and noticed the opened card envelope and card was on the desk.

A rush of excitement ran over her body as she wondered what it was like for him to open the card. She wondered if he had any idea who had placed the card under his door that morning.

She sat down in his office chair. A well worn black office chair that looked like it had been used by him for a number of years.

She sat down in the chair to wait for the inevitable moment when Harvey would arrive.

She kept waiting and waiting.

The minutes continued to drain by and there was no sign of the janitor that Erin had a massive crush on.

She thought about leaving as perhaps it was his way of saying he wasn't interested.

The thought was dissuaded by the fact the envelope had been opened and the door was unlocked after school. She knew she just had to keep waiting.

The unfinished ceiling featured all sorts of pipes and vents running every which way. She looked and tried to guess what each pipe did and where it went in the building. The sounds they made seemed like the perfect cover for whatever mischief the two of them might get into.

Since she knew she was in deep, she figured she might as well go all of the way.

So, she stood and took off her sweater, bra, leggings, skirt, panties, and boots.

She sat her naked and horny body back in Harvey's chair.

No matter what happened when the door opened, she was going to get a chance to live out her fantasy.

Just as her boredom was about to get the best of her, she looked over to the locked wooden door and saw the crack of light underneath change.

A shadow appeared underneath the door and soon the handle shook but didn't open.

Erin could feel her heart pulsate with a rush of adrenaline. There was no turning back.

Then the deadbolt to the door clicked and the heavy door opened.

There he stood, the birthday boy, and he peered into the basement room he called an office.

His brown eyes popped as he finally made out who was inside his office, "Happy birthday to me. Hello there, Erin."

He stepped inside and closed the door and bolted it shut.

He could feel his cock twitch with excitement as the naked young woman rose from his chair with a smile on her gorgeous face, "Happy birthday, Harvey. I hope you don't mind that I let myself in."

He glanced around the room for any sign of a prank, "This can't be real. Who is setting me up?"

Erin knew the question would be coming and just shook her head no, "No set up. Harvey, I'm not going to lie. I'm very much into you. Something about a man in uniform."

She stepped towards him and threw her hair over her shoulder and it danced down her right side, drawing his eyes to the fact that the most popular girl in the school was naked in his office.

He knew all of the risks if they were caught. He would lose his job and face worse penalties. He also knew that she was the most beautiful woman he had ever seen naked and wasn't going to pass on the chance to be with her.

"I'm going to need you to prove it. Get on your knees and suck my cock."

Her heart fluttered. She was about to give herself as a gift to the man who was the most looked down upon person in her school.

She descended down to the cold concrete floor.

Her nipples stiffened as the arousal surged throughout her body.

She looked up with her ocean blue eyes and slowly shifted her luscious hair to her back.

He unbuckled his work pants and let them fall to the floor, "You can handle the rest, Erin."

She bit her lip as her hands ascended his thick legs up to his grey boxers.

Delicately, the 18 year old high school senior pulled the boxers down and out popped Harvey's erect cock. His seven inch erect cock sat tantalizingly close to the wanting mouth of the girl who wanted to free herself of expectations and stress.

Her mouth hungrily dove onto the erect cock.

He moaned instantly, "Oh, happy birthday to me. You're the best present. Oh fuck yes, Erin."

He gathered her long hair into his hands and took great delight to feel how soft and well maintained it was. He wrapped it around his left hand to give him some semblance of control over the young and eager slutty high school girl.

She felt instant relief and a complete resetting of who she was as a person. For the first time, she was doing something that she shouldn't be doing but the fulfillment of her deviance felt even better than she imagined.

The concrete floor was cold but her body and pussy felt warm as her head began to ride his cock up and down.

Delighted moans escaped her mouth as she began the process of giving her pristine teenage body to the man who would most upset those who expected so much more from her.

She wrapped her tongue around his cock and sucked hard as her desire dared him to cum in her moist mouth.

Up and down, more and more, she gave herself to the janitor.

His burly chest began to rise and fall faster and faster as his body wished to cum. He did everything he could to hold back as long as possible to enjoy his first blowjob in multiple decades.

He could barely contain himself any longer and pulled on her hair to quickly remove his cock from her mouth.

"I need to cum on your tits."

He was just barely able to position the busty high school senior under him in time for his cum to shoot out of his cock and onto her perfectly plump natural breasts.

"Ohhh, fuck. Erin!" He moaned as his splooge hit his intended mark.

She could barely contain her excitement as the taste of his cock lingered in her mouth but her breasts had his cum all over.

"Spread it all over you, baby."

She did exactly as she told and used her hands to move his cum onto her nipples and over her soft natural breasts.

She felt like she was his.

He felt like the luckiest man on the planet.

He held out his hand and helped her off the concrete floor, "That was just the start."

She beamed with a radiant smile as he stroked her face and then went in and passionately kissed her.

Their mouths interlocked as their hands explored each other's forbidden bodies.

He unbuttoned his shirt to reveal his broad chest. The blue collar ruggedness made her feel even more attracted to the fit older man she had just given a blowjob to in the high school basement.

Once naked, he went over to his large workbench and meticulously cleared it off.

The all steel table was cleared off. Once cleared, he took a clean towel and laid it over the table.

He turned back around to the young naked teen in his workshop and went and scooped her up in his arms.

She flung her arms around his neck and they caressed in a lovely kiss before he walked her over to the table and laid her on it.

The petite girl had plenty of room to lay down on the table.

Her unshaved pussy gleaned from having been turned on and wet from the blowjob she had given her crush.

Her plump breasts protruded upwards as she stared to the ceiling.

She felt perfectly relaxed. Perfectly horny. No stress, just lust filled her body.

She had taken her chance and the joy of his reciprocation left her with a broad smile.

Her happiness radiated to him as well. He couldn't believe what he was looking at. The hottest girl in the high school wanted him.

"I've worked on a lot of projects down here but you will for sure be my favorite."

He went in between her open legs and stared at her wanting pussy.

"You did such a good job on me, it wouldn't be hospitable of me to not return the favor."

His face went into her crotch and his tongue hungrily found the soft folds of her tight pussy.

Pleasure filled her body as the naked janitor's tongue filled her pussy.

She braced her arms on the table to be able to sit up to watch him work her over.

"Oh my...oh Harvey."

Her words were masked with audible gasps as he explored her pussy with his tongue.

He reached up and clasped his hands on her curvy hips to gain some leverage.

Her toes curled as the much older janitor worked deeper into her high school pussy. The forbidden sex made her feel even more turned on.

An orgasm quickly began to build in her. The sexual shock of his tongue going faster in her pussy sent an orgasm pulsating from her hips all the way up her spine and down to her toes.

She threw her head back and moaned, "Ohhh...ohhhh...fuck....mmmm...Har...vey!"

Her vision went white for a moment as she orgasmed.

She lost her breath as her moan depend, "OHHHH!"

She came.

He could feel her pussy fill with her cum.

He happily licked her pussy to taste her juices.

At that moment, he knew he had fallen in love with her. Regardless of the risk he knew he had to do everything he could to be with her. He felt alive once again. She was a true dream come true.

He realized his cock had twitched back to life.

A second erection was a sensation he hadn't felt in a very long time. He hasn't had a need to and certainly had never been with a woman as beautiful as the one on his work table.