Stewarts Best Week Ever Tuesday

© 2023 JRydher, JRydher1

It's best to read

Stewart's Best Week Ever: Monday

prior to reading this chapter.

All those engaging in sex are at least 18 years of age.

~~~

Stewart Lewis started his week off on Monday by being bullied, but the day eventually did a 180 degree turn. He lost his virginity to the head cheerleader and then had sex with both the vice-principal and her secretary. This chapter picks things up Tuesday morning.

~~~

Tuesday morning arrived like every other morning. Except, Stewart for the first time in a long time felt some hope. But, despite Monday's unexpected loss of his virginity and some orgasmic revelations, Stewart's hope soon turned to dread when the school bus came into view. Stewart hopped on the bus, which was mainly filled with underclassmen, and took his lonely seat at the back of the bus. The other students either ignored him or talked behind his back, completely clueless of Stewart's amazing start to the week.

As they got closer to school, Stewart started to worry about the retribution Brad Wallace and his buddies might exact from him for having sex with Nancy and being humiliated in front of Stewart. A panic started to creep into his body as the bus pulled up in front of the high school. Stewart's legs felt heavy as walked down the aisle of the bus and down the steps to the sidewalk.

Just as he began to walk towards the entrance, a Rolls Royce pulled up. The chauffer scurried around to the passenger side back door and quickly opened it. Out stepped the queen of Los Marquez High herself, Chrissy Vanderhoof. She was the hottest girl in the school and she knew it. She was also the meanest girl in school and she knew that too. You didn't talk to Chrissy Vanderhoof unless spoken to and if you weren't in her inner circle, you most certainly didn't make eye contact with her. Legend had it that students mysteriously disappeared after having made such a mistake.

Chrissy's minions ran over to her. They complimented her outfit, her hair, her shoes, etc. Then they fell in behind her; after all the queen must always go first. The exception was for one of them to open the school door for her. A task they would shove each other out of the way to do.

The Vanderhoofs were the wealthiest family in Los Marquez and one of the wealthiest in California. Chrissy's Mom, Emilia, was an executive at Warner Brothers. Her father, Everett III, was a mover and shaker on the New York Stock Exchange. He split his time between the two coasts, which meant that Chrissy, an only child, spent much of her time by herself. Well, her and the servants that ran the mansion the Vanderhoofs lived in.

Chrissy truly had it all, brains included. She was extremely bright and was in many of the same advanced classes that Stewart was in. But, the two had never spoken, nor had their eyes ever met. So, it came as a huge surprise when after Tuesday's AP Physics class, Chrissy approached Stewart Lewis.

"Stewart," began Chrissy. Stewart was confused. Is she talking to me? He didn't dare look at her, choosing to stare out the classroom window instead. "Stewart...Lewis...I'm talking to you." Stewart apprehensively turned his head and faced Chrissy. He kept his eyes lowered, however.

"Ye...yes, Chri...Chrissy."

"Would you relax. I'm not going to bite. And, for Pete's sake look at me." Stewart looked up and for the first time truly saw Chrissy's beautiful light hazel eyes. They contrasted magnificently with her dark brown hair.

"Stewart, I need your help with next week's exam." Stewart had a puzzled look on his face. He was the only one standing in the way of Chrissy being class valedictorian. Suddenly, a cold shiver went down his spine. Was she going to kill him? Clearly, he had seen too many movies and TV shows. Chrissy's words snapped him back to reality.

"Stewart, are you listening to me? I said I need your help with next week's exam. I've fallen behind in class."

"Oh, um, what can I do to help?"

"I need your brain." Oh God, she is going to kill me, Stewart thought. "I need your brain to help me with the areas I'm having trouble with. Are you busy tonight?"

"Tonight, er, no."

"Good. The sooner the better. Can you drive to my house or do I need to send our chauffer to pick you up?"

"No, I can drive. I can borrow my Mom's car."

"Good. What's your cellphone number?"

"555-183-3040." Chrissy punched the digits into her phone and texted Stewart with her address.

"I'll see you tonight at 7. Don't worry about dinner. I'll have our cook make something for us." And, just like that she was gone, leaving Stewart stupefied. But, he was snapped out of his mental haze when he stepped out into the hallway. Before Stewart knew what hit him, he was shoved into a row of lockers. His books and papers went flying everywhere. Brad was in his face in seconds and a bunch of his teammates surrounded him.

"You thought I was going to kick your ass yesterday, loser? Well, today they are going to have trouble identifying you when I'm through with you." Just as Brad was about to haul off on him, Nancy and some of her fellow cheerleaders interceded.

"Hold it," said Nancy as she and the cheer squad squeezed between the players and Stewart. "Back off, Brad. You're done picking on Stewart."

"Oh, is he your new boyfriend now? Get out of my way." He started to move Nancy out of the way, but she slapped him in the face. Brad looked like steam was about to blow out of his ears. He looked like he might hit Nancy, but then she shoved her phone in his face. A picture of Brad naked was staring back at him.

In a quiet voice, Nancy said, "You and your goons are going to walk away right now and never pick on Stewart again, or every girl...and guy...in this school is going to see just how tiny your penis is really is. No girl will go near you. You know me well, so you know that I will do it. And, don't bother trying to grab my phone; I have plenty of copies elsewhere. Oh, in case you haven't figured it out already, you and I are through. Bye now." Nancy emphasized her last statement with a little wave.

"Come on guys," Brad grudgingly said, and they all walked away.

"Are you okay, Stewart?" Nancy said.

"Yes. Thank you."

"You're very welcome, Stewart." The cheerleaders helped Stewart pick up his books and schoolwork and walked down the hall with him to his next class. It was like he had his very own sexy Secret Service. Heads turned and jaws dropped to see this very different alliance.

Stewart spent the next 45 minutes in Trigonometry class, but his thoughts were about Nancy. Specifically, her taking his virginity on Monday and then her heroic actions earlier in the day. He was lost in thought when an announcement on the PA system got his immediate attention.

"Stewart Lewis, please come to Vice Principal Mason's office. Stewart Lewis to Vice-Principal Mason's office." The voice was that of Mrs. Wilkins. Clearly the vice-principal had heard about his encounter with the football team.

On his way to the office, Stewart noticed his fellow students looking at him and whispering. Girls that ignored him were suddenly smiling at him. Several members of the boys' basketball team high-fived him as they walked past him. Stewart's mind was racing as he entered Mrs. Mason's office. Mrs. Wilkins looked up from her laptop and smiled. Then she winked at him and said, "You can go right in." She smacked him on the behind as he walked by, causing him to jump.

"Mrs. Mason, you wanted to see me?"

The VP looked up from her paperwork. "Yes, yes Stewart. Please close the door, we don't have much time."

"Time for what?" Stewart said and gulped.

Mrs. Mason walked over to the blinds and quickly closed them. "First off, I wanted to let you know that Brad Wallace has been suspended for 10 days. I don't think he's going bother you any longer. And, I've already spoken with Coach Singer about stopping the rest of the football team from harassing you or I'll be in contact with the schools offering them scholarships. I don't think you will have to worry about them going forward.

"Thank you Mrs. Mason!"

"Ali."

"Right. Thank you, Ali."

Now, that business is taken care of Stewart, take out your cock!"

"But, Ali..."

"Take it out, Stewart. You need to get to class soon.

"Yes, Ali." Rather than protest about it being the middle of the school day, Stewart undid his belt and jeans and let them drop to his ankles. He then slid his underwear down as well. Ali grabbed his cock with her right hand and started pumping furiously. At the same time, she began running her tongue along the edge of the head of his cock. Stewart let out a low moan as his cock responded to Ali's touch. She squeezed his testicles as his head started to bulge.

"This will have to do for now. Give me your cum, baby. Give it to Ali." The excitement of getting a handjob from the vice-principal in a school full of students got Stewart breathing rather heavily in a heartbeat. "That's it Stewart, shoot out all of the creamy cum for me. I want it. Give it to me. Give it to me now. Shoot it out of that big gorgeous cock of yours."

Stewart began grunting as he neared his orgasm. Ali grabbed an empty travel coffee mug from her desk and aimed Stewart's cock head at the inside of it

"That's it my big man. Give Ali something creamy to drink." No sooner had Ali finished her sentence, then Stewart's cock starting blasting the inside of the coffee mug. Shot after shot went into the container, some went over it and on to Ali's desk. She excitedly said, "Yes, yes. That's it. Give it all to me." Her words spurred some extra fluid from Stewart's cock until he grabbed on to the desk for balance and was seemingly out of ammo. But, Ali jammed the head of his cock in her mouth and sucked out a couple more spurts of ejaculate into her wanton mouth.

Ali wiped her lips and laughed as she looked in her coffee mug. "My God, Stewart you filled up half this mug. Plenty for me to mix in with my coffee now and more for later," she said with a lascivious grin. "You best get dressed and get to your next class. Please show yourself out while I clean up in here.

And just like that, Stewart got dressed and left Mrs. Mason's office. He was glad that Mrs. Wilkins wasn't in the outer office as he attempted to get to his next class unnoticed. There was still two more hours of school. Surely, nothing else crazy could happen today. But, so far it had been no ordinary week.

English Lit was next and Stewart couldn't help but think about the last two days and how his life had changed. Had he gone from being ignored to, should he even think of it that way, a stud? No, no...that's a ridiculous thought. Or was it? Stewart's mind couldn't help but wander during class. He replayed Ali's handjob in his mind and soon he had a large bulge in his jeans. That's when he heard a gasp to his left.

It came from a very cute girl named Emmy. She was transfixed staring at Stewart's bulge. Stewart turned red with embarrassment as did Emmy. They both tried to focus on the lesson but kept glancing over at each other. When class was over, Stewart was finally deflated and hurriedly left the room so as not to have any further contact with Emmy.

Finally, the last class, which once again meant Phys Ed. Stewart was hoping it was less eventful than Monday's class. Stewart grudgingly got changed and headed outside. Tuesday was co-ed kickball day. The uncoordinated senior took his usual position in right field, but instead of no one standing anywhere near him as usual, Nancy came sauntering over.

"Hi Stewart," Nancy said in a surprisingly shy tone.

Stewart smiled and replied, "Hi Nancy. How are you?"

"I'm good, thanks. Kind of boring out here, ya know?"

"Yeah, I guess so."

"So, here's the plan. The next time the ball is kicked over to that side of the field, run to the field house and don't look back."

"What?"

"There it goes. Now, run." Nancy took off with tremendous speed, with Stewart running as fast as he could to try to catch up to her." They ran behind the field house that was adjacent to the football stadium and leaned up against the wall.

"What's going on?" Stewart asked. Nancy answered him by putting her arms around his neck and initiated a deep and sensual kiss.

"That's what's going on. Come on." Nancy pulled a key chain out of her pocket and opened the locked field house door.

"How did you get the key?"

"It's a master key I stole from one of the custodians a couple of years ago. I know I can trust you not to tell anyone."

"I won't."

"Yesterday was so unbelievable. I need you inside me again."

"I'm actually a little sore right today. Would you mind if I ate you instead?" Nancy's eyes widened in surprise and laughed.

"You're volunteering to go down on me?"

"Yes. Is that strange or something?"

"Brad hated doing it. He's more of the wham bam, thank you ma'am type. He thought performing oral sex on me was gross."

"Why would he think something as beautiful as a woman's vagina was gross?

Nancy smiled widely and took no time at all to drop her shorts and panties, and laid down on a weight bench. "Have at it, Stewart." Stewart kneeled down on the concrete floor and moved Nancy's legs further apart. He remembered everything he did to Mrs. Wilkins on Monday and proceeded in the same fashion. Before long he had Nancy groaning, moaning, and repeating "Yes" over and over again. Nancy gripped the sides of the weight bench and wrapped her legs around Stewart's sides as she screamed out as the first orgasm hit her. Stewart continued his oral assault on Nancy's clit, while he used two or three fingers to fuck Nancy's increasingly wet vagina. He squeezed Nancy's breasts through her t-shirt and bra. Her nipples stabbed at his palms as she arched her back and came once again.

"Oh please, please don't stop." Stewart continued on with his fingers while he began to tongue the outer rim of her anus. It sent Nancy over the edge for a third and final time. Suddenly, she burst into tears and Stewart instinctively put his arms around her.

"Did I hurt you? Are you okay?"

Through tears, Nancy said, "A boy has never made me orgasm before."

"But didn't you have a lot of sex with Brad."

"Brad is only concerned with Brad. I always ended up bringing myself to orgasm afterwards." There was an awkward silence and then through tears Nancy's next words stunned Stewart.

"Stewart, I am so sorry and ashamed for how horribly I've treated you for so many years. Early on, when I knew it was wrong, I was too chicken shit to not go along with Brad and others. I was so desperate to be popular and to be liked. You're a dear sweet boy and I promise you, I will always have your back from now on no matter what."

"Thanks, Nancy, I appreciate that. Apology accepted on one condition."

"Anything."

" Um, would you like to go on a date with me sometime?" Stewart asked while looking down at the floor.

Nancy shocked him again. "Yes, yes I would. How about a movie on Saturday?"

"I'd like that."

"Me too." The duo snuggled for a few more minutes before they realized the time. They locked up the field house's equipment room door and seamlessly snuck back into right field of the kickball game as if they had never left.

On the bus ride home, Stewart got a text from Chrissy. "Do cheeseburgers, fries, and cokes sound all right for dinner? Also bring your bathing suit in case we have time to use the pool."

Stewart texted back, "Okay" and immediately feeling nervous about going to Chrissy's that night. He also felt excited and began to get hard, which made it awkward when he departed the bus. He kept books in front of his crotch as he exited the vehicles, but he still heard a few laughs, gasps, and saw a few female mouths agape.

~~~

Stewart pulled up to the address that Chrissy texted a few minutes before 7 pm. There was a double iron gate with an intercom speaker on the driver's side of the car. Stewart pushed the button on the speaker and a moment later an elderly sounding gentleman asked Stewart to "State his business."

"My name is Stewart Lewis. I'm here to see Chrissy Vanderhoof."

After a short delay, the man replied, "She's expecting you; please follow the driveway up to the main house." Stewart thought to himself 'The main house'? A buzzer sounded and the gates opened allowing Stewart to drive his mom's 10-year old Ford Escort on to the grounds of the Vanderhoof estate. Five minutes later he pulled up to a giant mansion that looked almost as big as Los Marquez High School. Stewart suddenly felt overwhelmed by his surroundings and was two seconds from pulling away, but Chrissy appeared at the front door.

It was a warm night in the valley and Chrissy was dressed accordingly. She wore a short lightweight dress that had pockets, and a pair of bright purple running shoes. She smiled at Stewart and removed one of her hands from her pockets to wave to him. The gesture eased Stewart's anxious mind and he shut the car off.

As he approached the door, Chrissy said, "Hi Stewart. I'm really glad you're here."

"Thanks, Chrissy. I'm happy to help you out in any way I can." She once again smiled at him and this time Stewart smiled back. Maybe, Chrissy wasn't so bad after all, he thought to himself.

Chrissy led Stewart through the large entryway and into a living room that looked like a grand ballroom. Stewart tried to keep his jaw from dropping to the floor as he took in his surroundings. His house could have fit in the living room. Maybe two of his houses. He stared up at the cathedral ceiling and eyed the handful of impressionist era paintings on the walls. Though he couldn't be sure, Stewart got the feeling they were originals. The pair made their way to the dining room where Chrissy motioned for Stewart to put his backpack on a bench off to the side. They sat down across from each other at the dining room table, which had 10 chairs on each side plus another two on the ends.

"It's nice to have dinner with someone for a change. My parents are never home," began Chrissy

"You don't have any siblings?" Stewart replied.

"No, it's just me. This place might be fantastic to the eye, but it's very lonely." With that, Chrissy looked down at her empty plate. A sad expression came across her face.

"I'm an only child too, but my parents are great. Oh, I'm sorry. I shouldn't have said that."

"No, it's okay. I'm happy they're there for you. I know you haven't had the easiest time though with all the bullying and nonsense."

"It's made for my own type of loneliness." Now it was Stewart's turn to look sad and stare off in the distance.

"I guess we may be very different, but a lot alike too."

"I guess so. You are definitely the smartest person I know."

"Oh, come on. I'm smart, but you're a freaking genius." Stewart turned beet red in response to the comment. "Okay, it's my turn to apologize. I'm sorry. I didn't mean to embarrass you. It's just that I've always really admired your brain."

"Really?"

"Yes, are you kidding me? I'm jealous of how your mind works. Things seem to come to you so easily. I have to work my butt off to get the grades I get."

"I never really thought about it. I study a lot too, but I guess it's always been fairly easy for me to retain information."

The two continued to talk to like old friends, until an older gentleman entered the dining room with a rolling cart topped with dinner. He served each of them cheeseburgers, French fries, pickles, coleslaw and sodas.

"Anything else, Miss Chrissy?" The older man said.

"Yes, George. This is my friend Stewart. Stewart this is George. He's like a grandfather to me." George smirked at the remark and shook Stewart's hand.

"Very nice to meet you Stewart. It's good to see Chrissy have her friends over. Since there's nothing else you need, I'm going to retire for the evening. Have a wonderful night, you two." Chrissy got up and hugged and kissed George.