Stewart's Best Week Ever: Wednesday

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

Be sure to read the first two parts (Monday and Tuesday) of Stewart’s Best Week

Ever before venturing into this one.

Stewart Lewis has had a crazy week so far. A week that is probably every teenage boy’s dream. At least the sexual part of it – sex with four different women in two days. Prior to that, Stewart had a rough life of being bullied, but once Nancy, the head cheerleader discovered what was hidden inside Stewart’s jeans, the 18-year old’s life completely changed.

~~~

Stewart woke up an hour early on Wednesday morning, well before his alarm was set to go off. He couldn’t help but smile thinking about the previous evening spent with Chrissy. He expected to help her study and then go home. He certainly didn’t expect to have sex with her and then fall asleep on the floor until she woke him up in a panic at 1 a.m. He called his parents and told them that the he had fallen asleep studying, but there was something in his mom’s voice that told him that she didn’t totally believe him.

Suddenly, he also remembered that he had made a date with Nancy for Saturday after having performed oral sex on her during gym class. Just then his phone buzzed with a text from Chrissy. “Last night was incredible. I can’t wait to see you at school today.” The reality of the situation sunk in; he was going to have to see both Nancy and Chrissy in school today. Thankfully, the two of them were not in the same classes as him at the same time, but at some point things could get awkward. Stewart knew that there was no point in rolling over and trying to go back to sleep, so he started his day early.

He went into the bathroom and brushed his teeth and was about to go back into his room to change his clothes, when his mother called for him to come into the kitchen. Normally, Stewart’s parents were already out of the house when he got up for breakfast, but since he was up earlier than usual he was already going to have to face his parents about the previous night.

“Good morning,” Stewart said as if nothing was different than any other day. Stewart’s Mom launched immediately.

“Good morning. So, your father and I have been talking about how late you got home last night and how you had us worried sick wondering what happened to you.”

“I know; I’m sorry.”

“Don’t interrupt.”

“Yes, ma’am.”

“We think it’s great that you’re getting out of the house and making new friends, but we are also concerned that you are suddenly getting out of the house and making new friends. Is there anything you want to tell us?”

“Um, not really. It’s just that things have been going better at school this week. Oh, Vice-Principal Mason suspended Brad Wallace for two weeks for what happened on Monday.”

“Really? That’s fantastic. It’s about time. I’ll have to call her and thank her.”

“Oh, you don’t have to. I thanked her already,” Stewart said, not necessarily wanting his Mom and Ali to talk too much.

“I know I don’t have to, but I want to.”

“Okay. Also, I have a date Saturday night with Nancy Richardson.” Stewart’s parents exchanged surprised glances.

“Well, good for you son,” said Stewart’s dad, speaking up for the first time.

“Wait a second,” said Stewart’s mom. “Isn’t she the cheerleader who is always picking on you?”

“Yes, but we had a long talk and she apologized for her behavior. She even cried. We talked for a while and then I asked her out and she said yes.”

“Okay. It’s not a knock against you, but I don’t trust that girl after all she put you through.”

“I know, Mom, but we kind of had a come to Jesus moment.”

“All right, but you be careful.”

“I will. I promise.”

“Oh, one more thing. While you were out last night, Mrs. Wilkins called and asked if you could help her with garden after school today. She said she would pay you and I told her you would be happy to do it for free.”

“Mom! Why did you say yes without asking me first?”

“I tried, but you were unavailable. Besides, some physical labor will do you good. And, you don’t need money to help a sweet old lady.”

“Yes, ma’am.”

“Now, go get ready for school.” Stewart slinked out of the room knowing full well which bush of Mrs. Wilkins’ needed tending to.

Stewart wasn’t used to juggling things in his life. His days were usually spent avoiding assholes and going to class. He realized he needed to just accept the changes in his life and try to push himself to come out of his shell. When the school bus arrived on Wednesday morning, he said hello to several of the kids on the bus and sat down next to someone halfway to the back of the bus. It was a freshman boy who looked very confused.

“Hey, I’m Stewart. What’s your name?”

“Alex,” said the shy, befuddled first-year high schooler.

“Nice to meet you Alex.” Probably for the first time since he moved to California, Stewart was excited to see what the day would bring. He stepped off the bus with a big smile on his face. Then he saw Chrissy getting out of her ride and Nancy standing on the pathway to the entrance. If he didn’t know better, he would have thought she was waiting for him to arrive. In a panic, Stewart quickly cut across the lawn before Chrissy could see him and stepped on to the main path to the building. His instincts were right; Nancy was waiting for him.

“Good morning, Stewart,” Nancy said with a big smile on her face.

“Hi, Nancy,” Stewart replied and kept up his quick pace.

Hey wait up. What’s your hurry?”

“I really have to use the boys’ room before class. Sorry.”

“No problem…see ya later,” Nancy said to Stewart’s back as he hurried into the building.

“Hey Nancy,” said a voice from behind. Nancy turned to see Chrissy standing there.

“Hey Chrissy, what’s up?”

“Beautiful morning, isn’t it?”

“Yeah, it is.” The two smiled and walked into the building together.

~~~

There was a knock at the door during one of Stewart’s Wednesday afternoon classes. The teacher stepped out to receive a small envelope from someone that Stewart couldn’t see. As she continued her lesson plan, the teacher walked down Stewart’s aisle and handed him the note to him.

He waited for the students on either side of him to look to the front of the classroom before he opened the envelope. Enclosed was a small note card that read, “Stewart, I can’t wait to have your cock in me. Meet me in the teachers’ parking lot 10 minutes after final bell. And, I have a special surprise waiting for you.- Jeri.”

Stewart gulped hard and took a deep breath, exhaling slowly. His focus for the remainder of the class was not about Spanish history, but about keeping his cock at bay.

~~~

Heading to his next to last class, Stewart saw Chrissy standing by the girls’ bathroom with a couple of her minions. “Hi, Stewart; come here,” Chrissy said and motioned with her hand.

“Hi Chrissy.” Before Stewart could say more, one of the minions opened the bathroom door and Chrissy pulled Stewart inside.” The two minions then stood guard.

“Chrissy, this is the girls’ room. I could get into a lot of trouble.”

“Don’t worry, Janice and Tia won’t let anyone in. I can’t stop thinking about last night.” Chrissy put her arms around Stewart’s neck and pulled him into a deeply sensual kiss.

“Wow,” said Stewart as their lips separated. “Last night was amazing. I haven’t been able to stop thinking about it either.”

“Stewart, I have to go to a formal affair Saturday night with my parents, but why don’t we go to the waterpark in the afternoon? Maybe around Noon or 1?”

“I’d love to,” said Stewart, then realizing he had plans with Nancy that night. “I better get going to class.”

“Me too. Talk to you later.” The two quickly kissed again before the minions signaled that the coast was clear and the two exited the bathroom and went their separate ways to class.

Phys Ed was the last class of the day as usual and Stewart, for the first time, was happy to attend because he knew he’d see Nancy. It was coed volleyball day. Stewart dressed quickly and entered the gym with his classmates. He heard a loud whisper and turned to see Nancy standing by the hallway entrance in her gym clothes.

“Stewart, come here,” she said and made a gesture for him to join her.

He quickly exited the gym and said, “What’s up?”

“This.” Nancy pushed Stewart up against the wall and mashed her lips into his. Her tongue slid into his mouth looking for contact. Stewart responded immediately and the two started making out in the hallway. Nancy grabbed Stewart’s cock through his gym shorts and squeezed it as it grew bigger and bigger. Stewart began to moan as he got more and more aroused.

“Nancy, stop or I’m going to cum in my shorts,” he said in a panic.

“That would be a terrible waste of all that beautiful creamy cum.” Just then a whistle blew inside the gym meaning it was time to break into teams and start playing volleyball. Nancy entered the gym in front of Stewart to afford him modesty while he desperately tried to get his cock to calm down.

Whereas Stewart and Nancy were able to easily sneak back into the dodgeball game the day before, Stewart was immediately busted as he strode across the gym. One of the instructors, Miss Cameron, saw that Stewart had an issue of sizeable proportion. “Lewis, in my office, now,” she said loudly.

“Oh shit,” Stewart muttered to himself. Miss Cameron was tough as nails. She had a pretty face that was surrounded by a short blonde bob and beautiful intense blue eyes. But, she had served in the military and had a muscular physique like a female bodybuilder. No one messed with her, not even the football players. She looked like she could snap them in two. No one knew what her sexuality was, not that it mattered to Stewart or most of the other students cared. Of course, there were those students who made fun of her or were disrespectful, but never ever to her face.

When Stewart got into the office, Miss Cameron closed the door and yelled, “Sit down.” Stewart quickly obeyed and sat on the chair facing Miss Cameron’s side of the desk.

“What the hell is wrong with you?” she said in raised tone.

“I don’t know what you mean,” Stewart responded.

“Don’t bullshit me, Lewis. You know I’m talking about you walking around the gym with an erection,” said Miss Cameron rather matter-of-factly. Stewart broke out into a nervous sweat.

“I…I didn’t mean to. I just reacted.”

“Reacted to what?”

“Um, you?” Stewart meekly responded. Miss Cameron stared blankly at Stewart for a few moments and then burst into laughter.

“Oh that’s a good one, Lewis. I’ll give you credit for that one.” Her serious face quickly returned. “Whatever the reason, you need to cut that crap out.”

“Yes, ma’am.”

“One other thing, Lewis.”

“Yes, Miss Cameron?”

“How big is that thing?” Stewart hadn’t been able to get used to all of the attention being paid to him and his cock or his cock and him, and turned red.

“I said how big is your cock?”

Stewart figured, screw it and said, “11.5 inches.”

Bullshit. There’s no way.” Stewart remained silent, but the discussion got his cock growing again. Miss Cameron finally broke the silence. “You’re serious, aren’t you?” she continued. “Let me see it.”

“What?”

“Don’t make me repeat myself, Lewis.”

“I’m not showing you my penis.”

“It wasn’t a request.”

While he was still shocked and taken aback, Stewart figured fuck it. He was so hard at the moment, it was going to be pretty obvious any way. So, he simply stood up and yanked down his shorts and underwear. His cock smacked against his stomach and pointed straight up towards the ceiling. It was already throbbing and precum was leaking out in anticipation of what might happen next.

“Holy fuck; you weren’t kidding, Lewis. Look at the fucking monster…and it’s thick too. I’ve got an idea.” Miss Cameron had a mischievous grin on her face as she grabbed a tube of hand lotion off her desk. She then unlocked one of her desk drawers and he could the hear sound of the hand lotion being squeezed out of the tube.

“Sit down, Lewis and take off your shirt,” Miss Cameron demanded. A puzzled Stewart sat back down and removed his shirt. He watched as Miss Cameron stood up, holding a cylindrical object in her hand.

“What the hell is that?” a wide-eyed Stewart said loudly.

“You’ve never seen a Fleshlight? It’s a toy I picked up recently. Just sit back and enjoy; it’s not gonna bite.”

“I…I don’t know about this, Miss Cameron.”

“Again, I didn’t say you had a choice.” The gym teacher squatted down next to Stewart and placed her left hand on Stewart’s bare chest. Her strong arm wasn’t going to let him go anywhere. Then she slowly slid the Fleshlight over the head of Stewart’s cock and down the shaft. Stewart responded to the sensation with a satisfied moan.

Miss Cameron had a shit-eating grin on her face as she started edging the rim of the head of Stewart’s cock. He probably would have fallen out of his chair if not for Miss Cameron holding him in place. At times, Miss Cameron would quicken the pace of her manual fucking and then slow down again. The back and forth timing drove Stewart wild. His legs were kicking out as he neared an orgasm. But, each time he did, Miss Cameron would slow things down again until the feeling subsided.

Finally, the teacher looked up at the clock and realized she needed to get back to the gym. She immediately started pumping the Fleshlight on Stewart’s cock with a rapid fire pace. Stewart let out a loud groan causing Miss Cameron to remove the Fleslight and pump Stewart’s cock by hand. The teenager’s emptied his cock all over his chest and stomach. Some even hit the underside of his chin. When he was done, cum started sliding down his body on to balls, the chair, and the floor.

Miss Cameron finally broke the silence. “That was fucking awesome, Lewis. We’ll have to do it again some time. Here’s a roll of paper towel. Clean up and get out of my office.”

“Yes, Denise.”

“What did you say?” shouted Miss Cameron.

“Miss Cameron, I said Miss Cameron.” Stewart cleaned up as quickly as he could and rejoined the others in the gym. Nancy immediately ran over to him.

“Are you all right? You were in there a long time and you look flush.”

“Yeah. She saw my erection when we came into the gym and she really handed my head to me because of it.”

“I’m so sorry. It’s all my fault. I shouldn’t have gotten you all aroused.”

“It’s okay. I promised her it will never happen again and it’s all cool now.”

“Good,” Nancy said, giving Stewart a quick peck on the cheek before returning to her volleyball team.

The rest of the gym class went by quickly and Stewart knew he had to go meet up with Mrs. Wilkins. After the surprise of what just happened, Stewart couldn’t imagine the surprise that Mrs. Wilkins said she had in store for him.

~~~

Mrs. Wilkins met up with Stewart in the teacher’s parking lot and quickly drove off of school property. They made small talk in the car while listening to a classic rock station on the radio. Mrs. Wilkins didn’t make any sexual overtures towards Stewart and Stewart’s cock obeyed itself. They actually had a pleasant time talking to one another.

The time went by quickly and before they knew it Mrs. Wilkins pulled into her driveway. As they entered the front door, she said, “I’m going to go upstairs to change. Why don’t you go out into the backyard. Just go straight through to the French doors at the back of the house.

Stewart said, “Okay” and headed to the glass enclosed porch in the rear. As he neared it, he heard some type of machinery running. He opened the doors and stepped out to find a Jacuzzi in the yard. A Jacuzzi with an obviously naked Mrs. Mason sitting in it. Her large breasts bobbed up and down on the water; her nipples clearly visible. She was also clearly playing with herself. Her left hand was under the water while her right hand squeezed and toyed with her right nipple. Just then loudly said, “Ohhhhhhhhh” as she get herself off.

As she caught her breath, she realized she wasn’t alone. She looked over to see Stewart standing there gob smacked. “Surprise!” she shouted. He also figured that’s why he didn’t get called to the vice-principal’s office earlier in the day.

“Come join me in the water, baby,” Ali said and then took a long drag on a joint. Stewart stood motionless and transfixed for what seemed like an eternity until he heard the French doors open behind him. Out walked Jeri completely naked.

“Stewart, you are overdressed. Get naked and join Ali and me in the water,” Jeri said. The sexy school secretary climbed into the hot tub and took the joint from Ali and took a long drag of her own. Then she and the vice-principal engaged in an open mouthed kiss that stunned and aroused the hell out of Stewart. He quickly discarded his clothes and climbed in the tub. Jeri handed Stewart the joint and went back to her tongue dance with Ali.

Stewart took a drag of the joint and nearly coughed his head off. “Easy, easy,” Ali said. Here let me show you how. The school disciplinarian showed her student how to slowly work the blunt to inhale from it without coughing. She handed it back to Stewart, who like everything else he did, picked up on it quickly. He sucked on the tip and inhaled, then exhaled calmly. “You are a wunderkind, Stewart,” Ali said. “And, good Good, looking fucking big and hard your cock is. You best get ready to use that thing in a minute, but first Jeri is going to eat my pussy.”

Stewart stood transfixed as Jeri grabbed one of Ali’s largest breasts in each hand. She squeezed them and ran her tongue over the nipples. She nibbled and bit them with her teeth. She used her mouth to suck on Ali’s nipples, stretching them to their max. She used her tongue to encircle them and lick the areolas. Ali was moaning and groaning until she finally slid up on to the seat of the Jacuzzi to give Jeri easy access to her pussy.

Jeri wasted no time using her tongue on Ali’s lips and clit. Stewart started to stroke himself as he watched Jeri put one and then two fingers inside of Ali’s pussy. First she gently probed Ali’s interior and then started fucking her with them. Ali looked over at Stewart and said, “Don’t waste that erection. Bring it to me.”

Stewart waded through the Jacuzzi and stood on the seat next to Ali’s. The vice-principal grabbed Stewart’s massive shaft in her hand and started sucking on the head with an incredible hunger. Jeri’s handiwork made Ali moan and hum on Stewart’s dick. The sensation was driving him wild. The feeling intensified when Ali started rubbing and squeezing his balls. Then Jeri interrupted them.

“Take his cock out of your mouth,” she said.

Looking puzzled, Ali did so and said, “Why?” Just then Jeri slid her middle finger into Ali’s ass.

“Ohhhhh fuccccccck,” Ali screamed as an overwhelming orgasm seared through her body. Jeri went back at Ali’s clit with her tongue, extending the orgasm. “Fuck fuck, oh fuck,” Ali kept yelling. “Stop, stop please stop. Oh my God. Holy shit.” Jeri winked at Stewart, who grinned from ear to ear.

“She’s ready for you now, Stewart,” Jeri said and motioned for Stewart to get back into the Jacuzzi. Still catching her breath, Ali got back in the tub as well and turned around. She grabbed hold of the side of the tub and stuck her gorgeous ass and drenched pussy into the air. Stewart got behind her and Jeri guided his cock into her waiting pussy. Stewart was moving slowly at first, but Jeri put her hand on his ass and basically jammed him quickly into Ali’s hot spot. Amazingly, her pussy swallowed up even more of his cock then when he had fucked her on Monday. Both participants let out a loud groan. As he was ramming into her, Stewart couldn’t get over the fact that he was fucking his vice-principal, one that had the body of a Sports Illustrated bathing suit model.

“Fuck her like there’s no tomorrow, Stewart,” said Jeri. The teenager heeded her words and started pounding Ali with tremendous force. Jeri put her hand between Stewart’s legs and rubbed his balls as he cock plowed the inside of Ali’s pussy. Still on edge from Jeri working on her, Ali came quickly, covering Stewart’s cock with her juices.