Wayside Ep. 03

Monday Message Mystery

All characters are 18 years of age or older

A week had passed since Brandon agreed to help Ms. Carrera with her Ipad, a meeting which devolved into rough sex and multiple orgasms. After losing his virginity to his Biology teacher, then hooking up with the sexy Spanish teacher twice, Brandon felt like a new man.

The school week had passed uneventfully enough, with no further chance encounters with either teacher. By the time the weekend rolled around, Brandon's positive outlook began to dim. His nerdy social circle and lack of interaction with most girls his age left him with no plans. The weekend ran its lame course, passing like many others.

He tried to remain optimistic as another Monday morning greeted him, but he felt inexplicably ominous. Brandon usually either caught a ride to school with Steve or one of his other friends with a car, but Steve's beater was in the shop. Brandon's mom, Cathy, had offered to drive him. Naturally, Steve would need a ride as well.

As they climbed into the car, Cathy turned to Brandon. "Honey, why don't you sit in the back? It's the polite thing to do," she said gently.

Brandon huffed and moved his was to the back passenger-side seat. He knew Steve (and all of Brandon's other friends) really liked his mom, a fact that he hated. Steve had even teased him about how hot Cathy was, bragging that he'd jerked off thinking about her. None of Brandon's other friends had been so bold.

Steve and Brandon had grown up close. Cathy almost considered him as another son, as they were thick as thieves in middle school. She still thought of Steve as the proper young man she'd known him as before puberty really hit.

As they pulled up to Steve's house, Brandon took a deep breath and tried not to let his obnoxious friend's (frenemy's) comments sour his mood any further. He considered telling his mother about the obscene remarks, but he was not eager to discuss masturbation with his own mom.

Steve strode out of his house confidently. He stepped up to the car and opened the passenger side to Mrs. Burley's smiling face. She looked sexy as ever to Steve.

Cathy Burley was in her late 30s, but did her best to stay fit and trim. She typically kept her thick chestnut hair in a mid-length bob with bangs. This was how she wore it today. She had on dark sunglasses and she smiled at Steve with pink, glossy lips. He was also wearing sunglasses, so he shamelessly gazed to her chest. Cathy was wearing a ribbed grey button up sweater that clung to her perky C-cups. In fact, Steve knew her exact bra size, 34C, as he had explored her drawer of undergarments several times.

"Hi Mrs. B," he said familiarly, climbing into the car with a smile. He studied her sweater-covered tits, trying to discern if she was wearing a bra. Maybe even one he'd handled personally.

"Hi Steve, did you have a nice weekend?" Cathy said as she pulled away.

In the front seat, the conversation flowed freely between Cathy and Steve. Brandon grumbled to himself in the back seat. From where he sat behind Steve, whenever he'd turn his head to look at his mom, he could see Steve's eyes lower to her body, not her face. Brandon gritted his teeth.

They pulled up to the school. "You boys have a great day," she said cheerfully, giving Steve's knee an amicable squeeze.

Brandon jumped out of the car and slammed the door loudly, not waiting for his friend. Steve was a step behind, but closed the distance quickly with his longer strides.

"I love your mom's sweaters. Do you think she was wearing a bra?" Steve chided.

"Shut the fuck up, douchebag," Brandon said, shouldering his backpack more firmly and trying to pick up his pace.

"Jeeze, lighten up, Burley. I was only kidding. What has gotten into you today? You were floating on air last week."

"Yeah well not everyone has three dates every weekend," Brandon said grimly.

"Look, you know I was at my Dad's house all weekend. I haven't locked down any of that out-of-town pussy yet," Steve said lewdly.

They entered the school and moved together through the Monday morning hallway bustle. Some of the tension between them dissolved as their discussion turned to one of their only remaining common interests: comic-book movies.

Steve was pontificating about which female super-hero he'd want to hook up with. "Yeah, Black Widow is the obvious choice, but I'd go for Agent Maria Hill. Someone has to break her, ya know?"

Brandon grunted in agreement.

"I bet you just need to get laid, Burley," Steve chuckled. They turned a corner hallway. "Speaking of which..."

Standing next to her open classroom door was Mrs. Fletcher. She wore a knee-length plum pencil skirt with pantyhose and matching plum heels. Her glossy white blouse was fully buttoned all the way to the collar. It was fairly tight and the short sleeves displayed her pale, freckled, feminine arms. Her shiny russet hair hung in loose bouncy curls that fell over the broad curve of her chest. She was talking to a student as she turned her head to noticed them.

Mrs. Fletcher made eye contact with Brandon. He met her bluish-grey eyes behind her dark framed glasses. She turned slightly toward him, her thick russet hair falling behind her shoulders. The swell of her breasts seemed to silently invite him to them, bulging against her collared blouse.

At the sight, Brandon flushed, a normal reaction for him. His adventures with Mrs. Fletcher had led him to a blowjob for both him and Steve, as well as losing his virginity to her. She'd inadvertently hooked him up with the Spanish teacher. Neither of the two teachers were aware, however, of their indiscretions with the young man. Brandon obviously knew, but had no idea what kind of discussion occurred between the two teachers.

Mrs. Fletcher was his first crush and his perfect MILF fantasy. He felt his balls churn as they their eye contact lingered.

Brandon told Steve, "Hey man, give me a minute, ok?" He crossed the surging hallway to Mrs. Fletcher, leaving Steve to gawk at them from the far bank of lockers.

Steve was also a bit awestruck by her radiance. His hand dipped into his left pocket, where he kept Mrs. Fletcher's panties. He'd acquired them after their tryst in the janitor's closet. The gorgeous Biology teacher had no idea that it was Steve who had given her a sloppy facial finish in that dark room. Since only Brandon had gotten to fuck her, he figured it was only fair that Steve got to keep her panties.

Brandon reached Mrs. Fletcher just as the other student she was talking to left.

"Oh, Brandon," she touched his arm. "Did you have a nice weekend?"

"Um, sure," Brandon said sheepishly.

"Well, I wanted to tell you that I thought your essay on evergreen photosynthesis was amazing," she smiled down at him, her golden red hair rippling. She gave his arm a gentle squeeze. "That's thesis-level writing, Brandon."

He smiled back, meeting her intense gaze, but fighting the urge to look down at her boobs. He could sense another student behind him, in line for Mrs. Fletcher's attention. Brandon started to shuffle away.

"Oh, I almost forgot. They delivered my new projector over the weekend." She produced a key labelled 'Audio/Video' on the ring. "Would you mind getting it out of the A/V room for me?"

"Sh-sure," Brandon managed, looking slightly up into the pale blue eyes of his Biology teacher through her dark-framed glasses.

She pressed the key into his palm and closed her hand over his. Brandon fought to steady his hand in her warm grasp. His cock thickened, snug in his tighty whiteys inside his jeans.

"Thank you, Brandon."

Brandon crossed back to where Steve was waiting.

"You are such a teacher's pet, Burley," Steve teased.

Seeing, smelling, and touching Mrs. Fletcher had raised Brandon's spirits significantly.

"Dude, seriously?" he retorted. "My relationship with her is what got you into that Janitor's close in the first place..." he leaned in close so passerbys couldn't hear, then continued in a whisper, "...you still have her panties..."

Steve absently played with the silky garment in his pocket. Brandon had a point.

On their way to retrieve the projector, Brandon realized they were near Ms. Carrera's room. If she was in, he could drop off her Ipad. He originally met with her to help her fix it, but ended up taking it home since they spent that lunch period fucking and barely got cleaned up in time for the next class.

Brandon thought maybe she'd thank him in a similar manner. He smiled broadly.

"Hey, I just remembered I gotta drop something off for Ms. Carrera," he said to Steve.

"Let me guess, another load in her pussy?"

"Steve!" Brandon punched his arm. "That's a secret!" he said in a whisper. "But maybe," Brandon added, smiling. "I fixed her Ipad and want to return it. But I also want to deliver the projector to Mrs. Fletcher."

Brandon paused, trying to improvise an ideal scenario where he might encounter both hot teachers. He figured he wouldn't have time for both and they were right by Ms. Carrera's room.

"Tell you what," Brandon said, retrieving the key for the A/V room. "Go grab the projector and I'll meet you there. If I don't make it by the end of McNeal's dumb Monday Message, then just head to Mrs. Fletcher's without me. I might be occupied."

Steve took the key from him with mixed feelings. His nerdy friend sure was getting a lot of tail these days. Even more than he was. Maybe Brandon could somehow hook him up with one of the gorgeous teachers.

"Try to get pictures?" was all Steve could come up with.

Brandon turned and left without responding. He seemed to be in a hurry.

Steve let his thoughts focus on Mrs. Fletcher. He brought her panties from his pocket to his face and inhaled deeply. The scent was beyond intoxicating, reminding him of how he'd just seen her moments ago in the hallway, and how he'd groped and sucked on those massive tits straining inside her sleeveless blouse. The tiny pink panties smelled like her pussy, as the janitor's closet had after their encounter, but it also just smelled like her.

His other hand gripped his semi-hard cock through his pocket. He played with himself as he made his way to the A/V area, careful to stash the panties any time a passing student got close. He didn't want anyone seeing the auspicious lacy garment. By the time he had to fumble for the key, he was at full mast, tenting his jeans.

Perhaps he'd take the opportunity to jerk off inside behind the locked door.

The Audio/Video area was comprised of two large rooms. The first was a storage area with shelves of equipment, where Mrs. Fletcher's projector sat, shiny and new. This area was dark, and as Steve entered, his attention was drawn to the second room, even larger than the storage area. This was the production studio and the lights were shining brightly.

"Fuck," he swore to himself.

He thought he'd have the space to himself and have the chance to rub one out. Unfortunately, the studio was all set to broadcast Principal McNeal's Monday Message to TV monitors throughout the school. It was separated from the storage area by a half-wall with soundproof glass to the ceiling. He could see the large camera, with the blinking red light aimed at the fake desk, complete with steaming cup of coffee. That's where McNeal would sit for the address.

He crossed the room so he could peer into the control room behind the production studio. Steve could see Principal McNeal with her back toward him. She was sitting on the counter in the control room, facing away from Steve and the studio. Usually, her sycophant vice principal, Bill Withers, was right by her side, especially for her little broadcast. Steve found it curious that he was nowhere in sight.

Steve's heart was pounding but he hated Principal McNeal and something didn't seem right to him. He crouched and slowly turned the handle on the door separating the dark storage area from the brightly lit production studio.

Principal McNeal's voice became audible through the cracked door immediately as she spoke in a commanding tone.

"Yes, Bill. Harder, mmmm. Oh, yes, its going to be even better than last week..."

Steve could see that she was distracted, so he pulled the door open enough that he could get a better view. He could see the Principal with her back to him. As he got closer, he could see two whitish shapes on either side of her.

"Right there, Bill," she said flatly, almost calmly.

Steve could see over her a little better. Those white shapes were her knees, spread wide and encased in white pantyhose.

"You have five minutes before we broadcast," Principal McNeal said menacingly. "I want at least two more orgasms before then. This is going to be one for the ages, Bill."

Steve heard the VP's muffled voice. "Yes, ma'am." Then Steve heard a regular, wet grinding sound, populated by the Principal's moans and grunts.

And he had an idea.

----------------

Brandon reached Ms. Carrera's room in a rush. He took a moment to catch his breath before knocking loudly.

"Hola!" came that bright, familiar voice. "Come eeennnn!"

He pushed the door open, entering the sunny classroom. Brandon saw the petite Latina sitting at her desk. Her silky brown hair was weaved into an intricate braid. She was wearing a yellow cowl neck sweater dress, belted at the waist with a black belt, with matching high heels.

"Brandon!" Nina Carrera said with a friendly smile. She stood and shuffled toward him excitedly, her heels clacking. She pressed against him in a hug, her shorter body warm against his even through her thin dress.

"Mm-Miss Carrera, hi," Brandon stammered caught off guard. Her breasts squished pleasantly against his chest and he found himself squeezing her tighter than he realized. Was she braless?

As they broke the hug, Brandon noted that she was indeed braless. Her tidy stiff nipples protruded prominently inside her thin dress. It made him want to grab them over the tight garment.

Nina smiled up at Brandon, but he only looked to her chest. Young men were so clueless. She gently used her finger on his chin to turn his eyes up to hers. Brandon blushed furiously.

"Mi chico," she said sweetly, "you have to at least pretend."

"Sorry," Brandon shrugged.

"Esta bien," Nina assured him. "It's flattering, but don't make it a habit, ok?"

Brandon nodded.

"Now, do you have a present for me?" Nina said, her eyebrows raising.

She looked very young to Brandon in that moment, almost like a young woman his age, asking for trouble. He considered unzipping and producing his semi-hard cock for her. Maybe they would get to that. Reluctantly, he unshouldered his backpack onto her desk and rooted around. Instead of presenting her with his dick, he offered her the repaired and fully charged Ipad.

Nina's large eyes turned into upward crescents as she beamed with happiness. She took it from him and unlocked it, swiping around the features with ease.

"Gracias!" she cheered, now almost jumping into his arms for another hug. She reached her arms up and wrapped them around his neck, bringing him down toward her.

Brandon hesitated for a moment, feeling almost as if they would kiss. His dark brown eyes met hers in a strange reflection. He felt his lips drawn to hers. At the last second, she turned her head, kissed him on the cheek, and pulled his head down into her bosom. He relished the heat of her body again through the thin material of the dress. One hand was on the small of her back and the other held her by her ribs, just under her perky boobs. He would only need to shift his hand a few inches to grab her pert, grapefruit-shaped breasts.

Brandon fought the urge, instead contenting himself to squeeze her slight body between his hands, almost around her waist. Nina gasped excitedly, feeling not only her stiff nipples respond, but also her throbbing pussy. If she was with the right man, she loved being handled roughly. And she knew Brandon could handle her.

Over his shoulder, Nina noticed the large wall clock. It was only ten minutes until students would begin arriving. She sighed, knowing she would need more time with the virile young man to sate her hunger. Her Toto would have to wait.

She pulled him away, out of the hug, fearing that he would only grope her more boldly and she would succumb. Instead, she thanked him again.

"And is there..." Brandon raised an eyebrow suggestively, "... a reward?"

Ms. Carrera placed her hands on his bulge, one hand landing right on his cock head, the other cupped at his balls. Her hands were met with throbbing movement beneath the denim.

"I'm afraid the reward will have to wait," she sighed, teasing and squeezing him. With a sigh, she stepped away. "You know how Principal McNeal is..." Nina said, her voice thick with sarcasm. "We can't miss El Mensaje," she added dramatically.

She went to the TV and flipped it on. Brandon had no intention of making a point to watch the broadcast. He'd hear all about it eventually. As he shouldered his backpack, he noticed something strange on the screen.

The muted image showed the brightly lit stage desk. The desk itself was vacant, with a short stack of papers and a steaming cup of coffee off to one side. As Brandon watched, a hooded figure entered the frame, as if coming from behind the camera, instead of from the side as the Principal always did.

"Who is that?" Ms. Carrera said absently.

They watched as the hunched, hooded figure approached the desk. He kept his back to the camera and the hood cast a shadow over his face. His right arm was moving as if he was shaking something. Suddenly, he jerked slightly to the side and the image showed him holding something long and pinkish, near his waist.

"DIOS MIO!" Nina cried, her hands clapping over her mouth.

He was holding his cock. Or a fake cock. But it was definitely intended to look like a long, stiff dick. Brandon stepped closer to the screen, looking into the hooded shadow of his face. As he studied it, Brandon saw a pink blob move out of the hooded area, disappearing into the man's pocket.

It was Brandon's turn to gasp. Mrs. Fletcher's panties. Was that Steve?!

As Brandon and Ms. Carrera and everyone else in the school watched on, the hooded figure squared up beside the coffee cup. The jerking motion stopped and a visible white stream leapt from his cock onto the rim and side of the coffee cup. The figure resumed jerking and adjusted his aim He stopped again and another white burst flashed from his tip, this time disappearing inside the cup. As the entire school watched awestruck, the hooded figure blasted several more streams of fresh cum into the Principal's coffee from the shadows. Then he was gone.

Brandon and Nina looked at each other wide-eyed. What the had just happened?

"I cannot believe what I'm seeing," Ms. Carrera gasped, stifling a smile.

Brandon's mind raced. That must have been Steve. But Mrs. Fletcher had given HIM the key, not Steve. Mrs. Fletcher would think HE had her panties, not Steve. If she had seen this, she would think it was Brandon.

Before he could process his thoughts, the screeching sound of a chair sliding sounded from the TV. On screen, Principal McNeal was taking her seat at the desk. She had a smug, satisfied look on her face. Brandon could only see her upper body, as she was seated at the desk. She wore a deep red U-neck blouse, and though she had every button fastened, a good portion of her chest and neck was visible. Somehow, she still managed not to show any cleavage.

Her ink black hair ruffled slightly as she reached for the cup and brought it to her thick red lips. She took a loud sip, then swallowed.

Janet noticed a slightly strange tang to her coffee, causing her to pause. She cleared her throat, stacked the papers for show, and began.