Stewart's Best Week Ever: Monday

Literotic asexstories – Stewart's Best Week Ever: Monday by jrydher1,jrydher1
©️ JRydher, JRydher1 2023

Everyone in this story engaging in sex is at least 18 years of age.

This is part one of a multi-part story. The first part has a good amount of background info before getting to “the action”. I hope you enjoy!

Stewart Lewis was born in a multi-generation family in a small town in Wisconsin. It was a factory town where all the families were close and the kids all grew up together. Both of Stewart’s parents worked at the factory as did one or both of just about every child’s parents in the town. It was a tight knit community, where everyone knew everyone…and their business…but it was idyllic. There were 4th of July picnics, Christmas caroling, Memorial Day parades, etc. It was small town America to a tee. But, it was also one of those towns that relied solely on the ups and downs of the factory.

Rumors began to circulate that the parent company was having financial issues. People were worried, but there had been similar rumors before and each time the factory survived. But, one winter’s day, when Stewart was 12, the rumors came true. The factory closed down and with it hundreds of jobs. It didn’t take long for the town to become a ghost town. With so many jobs reliant on the factory, people moved out in droves. Stewart’s mom and Dad, Jim and Shirley, eventually found jobs at an automaker in Southern California. It was a big move, but the thought of no more hard winters appealed to the family. Pre-teen Stewart was sad to lose all his friends, but his sunny outlook on life and his parent’s words of encouragement gave him the confidence that he would do well in his new school and environment. They couldn’t have been further from the truth.

Things were great at first; they had a small house in a decent neighborhood. It kind of reminded the Lewis family of their town back in Wisconsin. But, the biggest differences between their old home and their new town of Los Marquez, was that they lived on the proverbial other side of the tracks. It was considered to be the poor side of town and the wealthier families looked down their noses at those who lived there. It was a shock to the system of the entire family, but especially to the intelligent, sensitive newly minted teenager. The difference between his “true home” and his new home were felt immediately.

From day one of middle school, other kids teased Stewart mercilessly. They made fun of his name, “Oh Stewie Lewie”, his clothing, his hair, his lack of coordination…just about anything they could think of. The treatment only got worse as Stewart got older. Kids resented Stewart’s brilliance. They gave him swirlies in the toilet, stuffed him in his locker, stole his lunch and/or lunch money, and poured paint, mustard, ketchup and everything else on him. They did everything they could to cause him embarrassment and indignity. At first, there were many nights when Stewart cried himself to sleep and complained to his parents about wanting to go back Wisconsin. It didn’t help that the school administration usually punished those responsible with nothing more than a slap on the wrist. Like most places, money talked and the majority of the kids picking on Stewart came from wealthy families.

The worst abuser of all was Brad Wallace, a football player and a grade ‘A’ asshole. The star running back was a leader on the football field, and unfortunately for Stewart, a leader of bad behavior off the field. The team followed Brad’s lead in heaping abuse on Stewart. As if things weren’t bad enough, they had a showing of the 1999 film “Stuart Little” at school. After that, Brad and company started calling him “Stewart little dick”. The girls were no better, especially those in the popular crowd of cheerleaders and self-professed beauty queens. They were sometimes worse at shoveled loads of crap on Stewart.

Stewart desperately missed his old classmates. They were able to zoom and text message, but it wasn’t the same, and, as you would expect, many of them drifted apart after leaving Wisconsin. He led a very lonely life. Sunday nights were stressful for Stewart and he often had trouble falling asleep. He used to look forward to going to school. Now, he hoped to get through the day without being bullied. He still loved to learn, he just wished he could be home schooled or go to a private school, but neither one of those was in the cards. Stewart couldn’t wait to go off to college and never ever come back to Los Marquez again.

Then one week in April of his senior year, Stewart’s life changed. No one saw it coming and the week certainly didn’t start out that way. On Monday morning the school bus pulled up as usual. Stewart sat in the back as always and was last off the bus after it arrived at school. He looked on as the students met up with their cliques and entered Los Marquez High School. As usual, Stewart walked in alone. By the time the afternoon rolled around, Stewart had given the day a B-. That’s how he made it through his days, by assessing each of them and writing about his experiences in his journal. There, he could vent his spleen about his anger, his frustration, and his loneliness and sadness. Stewart loved the end of the day, but he also dreaded it. That’s because his last class of the day was the one that Stewart hated the most…Phys Ed.

It was basketball day, which meant one of the teams would be “stuck” with Stewart. He would never touch the ball, because no one on his team would ever pass it to him. But, on this particular Monday, Stewart decided he would get the ball and shoot no matter where on the court he was. Unfortunately, Stewart was on Brad’s team. It was like having a nightmare, waking up, and realizing you were still in another nightmare.

The game began and midway through, Stewart seized his moment. He ran up under the basket and stole the ball from Brad, his own teammate. He quickly shot the ball…and it went in. Stewart began to celebrate until he realized everyone was laughing at him. He had shot the ball into the wrong team’s basket.

While most of his classmates laughed hysterically, Brad freaked out. “You’re a dead man Lewis. What kind of a fucking idiot are you?”

“It’s just a game,” was Stewart’s unfortunate reply.

“Oh yeah, well this is just my fist,” Brad retorted. Thankfully for Stewart’s sake, the gym teacher stepped in just in time and told Brad to “Take a seat and cool off”. But, the fuming Brad was not going to cool off. When class ended, everyone poured into the boys’ locker room. It was always Stewart’s goal to change and get out of the locker room as quickly as he could. Since gym was the last class of the day, Stewart skipped the showers at school for his own safety and would shower at home later. But, on this particular Monday, Stewart wasn’t fast enough.

Wearing just his underwear and about to put on his jeans, Stewart was grabbed by Brad and a couple of his buddies. Stewart kicked and punched, but the stronger boys pulled off his underwear, and tossed the completely naked Stewart into the gym and locked the doors behind him.

“What the fuck?” screamed Nancy Richardson. The head cheerleader was one of Stewart’s biggest tormentor’s and Brad’s girlfriend. “What the fuck do you think you’re doing, you fucking pervert.”

“Gross,” added Lisa Michaels, another cheerleader and Nancy’s best friend.

“They threw me out of the locker room. I can’t get back in,” said Stewart as he cupped his groin area with his hands and kept his back to the cheerleaders.

“I said get out here, you perv,” Nancy shrieked. After a brief standoff, Nancy told Lisa to “Go get Mrs. Mason”, referring to the school’s vice-principal.

“No, don’t do that. I don’t want any trouble.”

“Well, you’re already in trouble, Stewart little dick.” The two girls started chanting “Stewart little dick” over and over again.

That’s when something inside of Stewart snapped. He dropped his hands to his sides and turned around and shouted, “I don’t have a little dick.” There hanging between his legs was a behemoth of a dick.

“Gross,” yelled Lisa once again. But, Nancy’s mouth was wide open, though no words escaped her lips. Her eyes were fixated on Stewart’s cock. “I’m going to get Mrs. Mason,” said Lisa and she ran out of the gymnasium.

“Quick, come with me,” said Nancy. “We need to hide you.” Stewart stood his ground until Nancy ran to him and grabbed him by the wrist. “Let’s go, she’ll be here any second.” She pulled Stewart with her as she ran to the girls’ locker room. Her eyes widened as she watched Stewart’s cock bounce and swing.

When the two got into the locker room, Nancy said, “Quick, get in the locker.”

“No way, you’re not doing that to me again,” Stewart replied.

“I won’t lock you in. I promise.” Stewart’s mind was made up for him when they heard Mrs. Mason and Lisa approaching. Stewart jumped in the locker and Nancy whispered to him, “Be very quiet.”

Mrs. Mason entered the locker room and looked around until she saw Nancy. “Miss Richardson, where is he?”

“Where’s who, Mrs. Mason?”

“Stewart Lewis. Miss Michaels said he was naked in the gym.”

“What? Gross.”

“So, where is he?”

“I haven’t seen him. Believe me I wouldn’t forget something as disgusting as that.”

“Nancy what are you talking about?” queried Lisa. Nancy shot an unspoken look to her friend, who knew that meant she had better shut up.

“I don’t know what Lisa saw, but I’ve been in here the whole time.”

“Just great,” said a skeptical Mrs. Mason. “If he comes back, one of you girls come get me.

“Yes, ma’am,” Nancy replied. When she was out of earshot and before Lisa could say anything, Nancy told her BFF to not say a word and go home. Lisa left without a protest. Nancy waited a few minutes to be sure Mrs. Mason wasn’t coming back and then opened the locker door.

“Okay Stewart, come out of there.”

“Thank you, but why of all people did you help me?”

Nancy pointed at Stewart’s cock and said, “Because of that. I’ve never seen anything like that.”

Stewart’s cock started to expand from seeing Nancy gaze at it in wonder. Simultaneously, he grew more erect as Nancy’s eyes opened wider. She finally grabbed the huge appendage with both hands and started licking the shaft and head as if it were the world’s largest ice cream cone. It caused Stewart’s wonder cock to get thicker and redder. Nancy, sucked on his balls, put part of the head in her mouth and stroked it furiously. She was like a kid on Christmas morning. The difference being her lips were shiny with precum.

“I need to have this in me Stewart. I need it now.” The cheerleaders discarded her cheer outfit, bra and panties and laid down on the bench in front of the locker. Stewart’s cock bobbed and dripped precum as he stared at the gorgeous Nancy lay splayed out before him. Though he was a virgin, Stewart was a quick study, even when it came to sex. He had read several books on sexuality and watched an educational “how-to” film. Nervously, he slowly started to push the head of his cock past Nancy’s outer lips. The further pushed into Nancy’s vagina, the more she thrashed on the bench.

“Oh my God. It’s so fucking big.”

Worried he was hurting her, Stewart stopped and asked, “Are you okay? I don’t want to hurt you.”

“It hurts, but in a good way…now keep going and fuck me hard,” Nancy implored. Stewart pushed on.

Nancy’s pussy was incredibly tight and it took some time for her to adjust to the large invader entering her body. As he got further inside of her, Stewart grabbed Nancy’s by the ankles and raised her legs high up for support. And, then he pulled his cock back and slammed it forward.

“Oh shit, yes” Nancy pleaded. Though his cock was barely halfway inside her, Stewart wasted no time and started pounding Nancy with his cock. Nancy was almost delirious from the fucking she was receiving. She was so turned on that when she played with her clit she brought herself to an orgasm in record time. And, that’s when Brad showed up. Apparently, Lisa had her suspicions about Nancy and had ratted her out to Brad.

“You son of a bitch, what the fuck do you think you’re doing with my girl?” an enraged and red-faced Brad screamed at Stewart.

Fearing for his life, Stewart jumped back, and in doing so, pulled his cock out of Nancy. That’s when she spoke up.

“You see that cock. That’s a real man, Brad. Now take your micro dick and get out of here, you asshole.”

“What, but Nancy…”

“I said take your pygmy penis and get out.” In a shocking display of emotion, Brad burst into tears and ran from the locker room. A stunned Stewart stood frozen for a moment, before Nancy spoke calmly to him.

“It’s okay, Stewart. The asshole is out of here and will never bother you again. Now, put that big boy back in me and ram me again like it’s your last day on earth.” Stewart snapped out of his of trance and reinserted his cock into Nancy’s even wetter pussy. He wasted no time and started rapidly slamming his cock inside of her. Being a first-timer, Stewart couldn’t hold out long. Within a couple of minutes, he suddenly grunted and his cock unleashed several loads of cum inside of Nancy. Still in the midst of ejaculation, he continued to thrust not realizing his cock had popped out of Nancy’s pussy. Soon, the cheer captain’s stomach, tits, pubic hair, and face were splattered with cum.

Stewart felt amazing. He was no longer a virgin and on top of that, he lost his virginity to one of the hottest and most popular girls in school. And, the pièce de résistance was Brad Wallace was left in tears like the many times Stewart had been.

A breathless, smiling Nancy sat up and said, “That was amazing, Stewart. Fucking amazing. Your cock is amazing. There’s so much cum. Holy shit.” Then she grabbed a towel and started wiping herself off as best she could.

“That…that was my first time.”

“Really? With me? That is so cool, I…,” Nancy stopped abruptly when she heard a voice. “Oh shit, it’s Mrs. Mason,” Nancy whispered. She grabbed her cheer outfit and bra and quickly ducked into a locker. Stewart panicked, grabbed Nancy’s forgotten panties and ran out of the girls’ locker and back into the gym. He started to sprint towards the boys’ locker room when he heard her.

“Hold it right there, young man.” Stewart turned his head to see Mrs. Mason, the school’s vice-principal. “Just what do you think…,” Mrs. Mason said before she saw Stewart’s penis draped over his hands and Nancy’s panties in an attempt to hide his monster cock. “You…you…n…n…need,” Mrs. Mason sputtered. Stewart turned beet red and quickly turned around to slip on Nancy’s panties. It was a ridiculous fit. His ass was hanging out the back and even sideways, most of his cock was spilling out of the front.

His attempt at modesty gave Mrs. Mason time to get some composure back. “Mr. Lewis to my office, NOW! And, take my blazer.” Mrs. Mason looked away, but out of the corner of her eye she could see Stewart’s cock spilling out of the panties as he put the blazer around his waist.

Stewart was grateful that it was late in the day and the school was relatively empty. Mrs. Mason was happy about it too since her nipples were very erect and pushing the limits of her bra and blouse. The duo entered the VP’s outer office where Mrs. Wilkins, the secretary to the principal and vice-principal, sat typing away on her computer. She raised her eyebrows as the partially clad student walked past her desk.

“Get in here and sit down,” an angry Mrs. Mason said. Stewart sat down, which made his cock slip its way through the VP’s blazer. Mrs. Mason closed the door and then shut the blinds to her office as a more than curious Mrs. Wilkins craned her neck to see in.

Despite his best efforts otherwise, adrenaline and the situation started to stimulate Stewart’s cock. There was nothing he could do about it now. It didn’t help that despite Mrs. Mason’s stern demeanor, her constant scowl and her apparent love of handing out detentions…everyone hated her…Mrs. Mason was a smoke show. She had an hourglass figure that was kept hidden under her endless array of business suits. Her long black hair was usually up in a tight bun, as uptight as she seemingly was, and she had stunningly blue eyes. Many of the male students were driven to distraction by her tits and ass.

Mrs. Mason, looking pensive, sat down and crossed her fingers. Her facial expression was serious, but her thoughts were anything but serious. My God, that’s the biggest cock I’ve ever seen. I need to see it erect. I need to suck it, I need to fuck it, she thought to herself. Her body began to betray her as well. Her large nipples became erect and were clearly visible through her blouse. She could feel a growing dampness between her legs. She began to question Stewart in attempt to maintain her composure.

“Stewart something tells me you weren’t running around naked of your own accord, but why were you in the girls’ locker room?” Waiting for Stewart to answer, Mrs. Mason’s eyes peered over the top of her desk and saw what looked like a cobra coming out of a basket. Nancy’s panties and Mrs. Mason’s blazer didn’t stand a chance in keeping Stewart’s dick at bay. Stewart saw where Mrs. Mason was staring, which only made his cock start to grow more. After a few moments, Mrs. Mason said, “Stewart, I asked you a question.”

Stewart had been stalling for some time. He didn’t want to betray Nancy, so he just started saying whatever he could think of. “I couldn’t get back in to the boys’ locker room, so I just ran into the girls’ locker room to hide.”

“Hide until what?”

“Until I could get back into the boys’ locker room so I could get my clothes.”

“And, so you just decided at that moment was a good time to try? And, where did you get the women’s underwear?”

“I heard you coming and I just panicked. I saw the panties lying on the bench and grabbed them in the hopes I could cover myself up somewhat.”

“Well I have one guess on who is responsible for you ending up this way and they will be dealt with severely. I know you’ve been told that by Principal Moore, but unlike him, I don’t kowtow to the football team. That being said, Stewart you can’t go running into the girls’ locker room like…like that.”

“Well what would you do? I mean look at me.” In that moment, Stewart suddenly found courage and daring, and stood up. His semi-erect penis stood out boldly in front of him as Mrs. Mason’s blazer fell to the floor.

“Stewart. What the hell do you think you are doing?” Mrs. Mason tried to maintain her focus, but it was gone. “Stewart…Oh God, that thing is huge. How big is it?”

“I don’t honestly know. I never measured it.” It was one of the few things in life that Stewart didn’t have an answer to.

Mrs. Mason opened her desk drawer and took out a tape measure. “Let’s see if we can figure this out. Give me my blazer and lose the panties.” She walked around her desk and knelt down. She placed one end of the tape into Stewart’s pubic bone and held the other end at the tip of his cock. “A little over 7-1/2 inches, but you’re not fully erect.” Her words and the feel of her breath on his cock aroused Stewart and his penis even further.

“8 inches…9 inches….10 inches…Oh, my God, it’s still growing. 11 inches…11 1/2 inches. Holy shit, I’ve never seen a cock so big! Let’s see how thick it is.” Mrs. Mason started to wrap the tape measure around Stewart’s cock, but the giant penis started twitching up and down. Mrs. Mason couldn’t take it anymore. She dropped the tape measure and grabbed Stewart’s swollen cock in her right hand…and then with her left hand as well. She started stroking it up and down, then she twisted it in her hands, and licked the large mushroom head. She purred as she lapped up the large amount of precum that had seeped out.

“I need this in me NOW, Stewart!” Mrs. Mason got up, let her hair down out of its confining bun, and quickly removed her skirt and panties. It was clear that her pussy was already very wet. Mrs. Mason rubbed the head of Stewart’s cock against her outer lips, mixing her initial dampness with his precum. “Put that beautiful thing in me, Stewart. And, hurry.”