© 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.
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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.
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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.
