Stewart's Best Wee Ever: Friday

©️ JRydher, JRydher1

Be sure to read the Monday, Tuesday, Wednesday, and Thursday chapters of Stewart's Best Week Ever.

Stewart Lewis had been bullied through all of his teenage years, but the discovery of his large penis turned his world on its head. From being a virgin to having sex with fellow students, a teacher, a school's secretary, the vice-principal and more, turned Stewart from a dud to a stud. But, all of the attention was apparently for one reason and one reason only. And, it was very large reason. Stewart wasn't sure how to handle it.

~~~

Stewart had trouble falling asleep Thursday night. He was happy that he pushed back at people trying to take advantage of him, but part of him felt like he had become the bully. He felt regrets for what he had done to Emmy, despite the fact that she jerked him off in class and showed up at his doorstep uninvited. As for Miss Martinez, Stewart had to admit to himself that he enjoyed having sex with her and taking control of her after she initially held all the cards.

His mind was scrambled thinking about how he went from being a bullied nobody to someone that women desired, or at least they desired his cock anyway. He felt like Nancy and Chrissy genuinely seemed to like him for who he was and he really liked both of them. He had already slept with both of them. And, now he had dates with the duo at different times on Saturday. What the hell was he going to do going forward? At some point, they were going to compare notes, or even worse, Emmy would tell them what was up.

Stewart finally fell asleep around 3 in the morning and immediately had a dream about Nurse Gretchen. She had been so kind in caring for him on Thursday. His dream turned sexual in a hurry; Gretchen was giving him a handjob and a blowjob while Stewart slept in her office. Why was everyone only interested in his dick? Gretchen seemed to be sneaking around in the dream, checking if Stewart was awake. Stewart suddenly woke up in a start and bolted up in bed. Holy shit, he thought he was having an erotic dream while he actually was in the nurses' office, but now he realized it was no dream. Gretchen had blown him and stroked him off for real. It was his cum that he saw in her hair. The dream was just a repeat of what happened for real. Stewart wondered how he could have been so stupid. He tossed and turned the rest of the night until the alarm went off.

~~~

Nancy was once again waiting for him when Stewart arrived at school. She excitedly approached him.

"Good morning, Stewart. Did you hear what happened?"

"No, what?"

"Miss Martinez never showed up for cheerleading practice yesterday. A janitor found her lying naked on her desk. She was babbling incoherently and masturbating. Stewart? Did you hear what I said?"

"Yeah, yeah. That's crazy," said a clearly distracted Stewart.

"She was supposedly put on sabbatical."

"Wow. How did you find about it?"

"I have my ways. How crazy it that though?" Nancy continued to talk, but Stewart heard none of it. He was obsessed with what happened with Miss Martinez on Thursday. Had he caused her some kind of psychotic break? He was brought back to attention by Vice-Principal Mason, who was waiting for him in the school's main hallway.

"Good morning, Stewart. I need you to come to my office, please."

"But, I have to get to homeroom."

"I'll write you a note." Stewart accompanied Mrs. Mason to her office as a puzzled Nancy watched them. The pair entered the main office, walked by a curious Mrs. Wilkins, and stepped into the vice-principal's private office.

"Please shut the door and have a seat, Stewart," said a serious Mrs. Mason. Stewart did as he was told and Mrs. Mason continued. "So, Stewart you may or may not have heard about what happened with Miss Martinez yesterday."

"I heard a rumor," Stewart said nervously.

"Well the plain truth of it was the janitor found her lying naked in her classroom. She was masturbating and was talking, but not making sense. Is that what you heard?"

"Pretty much."

"That's because I made sure one detail didn't make its way around...she was also smearing a large amount of cum all over her body. I only know of one person in this school who could produce that much cum. Is there something you want to tell me?" Stewart sat motionless for several minutes until he finally spoke up.

"Not really."

"Are you sure?"

"Yes, ma'am."

A frustrated Mrs. Mason said, "You know damn well that was your cum, Stewart..."

"So," Stewart nonchalantly replied.

"You can't just go around having sex in the classrooms."

"Oh, so it's only reserved for your office and only you and Jeri can claim my cock?"

"Yes, I mean no. You know what I mean."

"No, I don't. I know that Miss Martinez, and you and Jeri are only interested in me because of my cock."

"That's not true, Stewart."

"Sure it is. Hold on a second." Stewart asked Jeri to step into Ali's office.

"What's up," Jeri said.

"I'm tired of the nonsense and charades," Stewart responded. Then he undid his pants and pulled them down. Ali objected, but Stewart yanked his underwear down leaving his semi-erect cock swinging in the breeze. "This is a tremendous blessing and a curse too. Since the discovery of my endowment, all anyone wants to do with me has to do with my cock. Don't get me wrong, I'm enjoying it, but I was ignored up until people started finding out about it

"As I said before, Stewart, that's just not true...," Ali began to protest, but Stewart cut her off. He wasn't having any of it.

"Jeri is getting wet right now staring at my cock. Aren't you, Jen?" Jen shrugged her shoulders and grinned. "And Jeri, what is it with you and this whole get up? Why are you dressing like someone's grandmother every day?"

"Stewart, I know what it's like to feel like a piece of meat. I was treated that way by my ex-husband...I'm not really a widow, by the way...I was treated horribly by bosses, boyfriends...I decided I wanted to be able to live two lives; my public life and my private life and they would be two separate entities."

"Well, no more," Stewart replied. Despite her protests, he grabbed the clips in Jeri's wig and removed them and the hairpiece, and tossed it across the room. He then fluffed up her gorgeous blonde hair. Then he unbuttoned her blouse and removed it with her assistance, and took off the wrap that bound her breasts. "Mrs. Wilkins is gone. Sexy hot Jeri is here from now on. Own it, Jeri. You too, Ali. Get your hair out of that ridiculous bun and get your tits out. I'm going to fuck them in a minute. Jeri smiled as Stewart then knelt down and began sucking on her nipples.

As if she were the pupil and Stewart were the administrator, Ali took her hair out of its usual bun and shook her long dark hair out. She unbuttoned her shirt and removed her bra and tossed it in the pile with Jeri's wig and bandage. She then joined Stewart in sucking on Jeri's nipples. The two removed the rest of Jeri's clothes and Stewart went down on her. Ali stripped completely and straddled Jeri's mouth. Jeri attacked her friend's pussy immediately, alleviating the tension in the room except for the rigidity of Stewart's dick. Now fully engorged, he entered Jeri's vagina. She groaned into Ali's pussy in response. After he brought Jeri to an orgasm, he pulled out, and as promised, started fucking Ali's big tits. Jeri licked his cock head as it popped out between Ali's tits. The trio kept changing positions with Stewart alternately fucking both women and the two women eating each other out and sucking and stroking Stewart's cock. Ali and Jeri enjoyed multiple orgasms and stroked Stewart off until another large load of his cum splattered on their tits and stomachs. Friday really was the best day of the school week. As Stewart dressed, the two women used their tongues to clean each other off.

On his way to class, Stewart decided he was going to make his own sexual destiny, even if it blew up in his face.

~~~

At lunchtime, Stewart decided to test his theory about Nurse Gretchen. He feigned a migraine as an excuse to visit her office for the second straight day.

"Stewart, I didn't expect to see you here again today. Are you all right?"

"No. I've got an awful headache and feel stressed out. Maybe it's a migraine."

"Well, I can't keep doling out medication, but how about you lie down and I try my reflexology again?" Nurse Gretchen was already starting to feel excited at the prospect of seeing Stewart's cock again. Her sex was already beginning to feel moist just from her imagination. Never mind the fact that she masturbated the night before thinking of her encounter with Stewart earlier in the day.

"Okay, I appreciate it." Stewart laid down and Gretchen applied a cold compress to his forehead. She then began to massage the pressure point in his hand to relieve his headache. She spoke to him in soft tones, using visualization to try to help him relieve his headache. Her voice and her touch once again aroused Stewart and his erection started to throb beneath his clothing. Gretchen stole a side-eye glance and could see Stewart's arousal. Just as he had the day before, Stewart nodded off and began to lightly snore. Gretchen immediately jumped into action.

Just as she had Thursday, Gretchen, closed her office door and the curtain over it, and threw the "Be back in 20 minutes sign on the glass. She sat down next to Stewart and very quietly undid his belt and pants, and pulled them down. She wasted no time and removing his underwear as well. And, there was her prize. Bigger than anything that could fit in a Cracker Jacks box. Gretchen repeated her technique from the day before; she slathered her hands with lubricant and started stroking the shaft of Stewart's cock with both hands. Her tongue swirled over the head, suckling up any precum that oozed out until she eventually took the head in her mouth. Stewart began to moan louder than he had the day before. Gretchen turned to check that he was still fast asleep, but Stewart was partially sitting up and staring at her. There was a fire in his eyes. Having been caught she momentarily froze; that gave Stewart the opportunity to sit up further and put his left hand on the back of her head. He then lifted his hips and started fucking Gretchen's mouth.

Gretchen groaned as Stewart's cock repeatedly rammed into the back of her throat. She dropped one hand down to massage his balls as he continued to prevent her from removing her mouth from his dick. Soon, he could feel his balls start to tighten and that familiar feeling that grows right before he ejaculates. Gretchen sensed it too, and try as she might, she couldn't get his cock out of her mouth. He began to grunt and his sperm rocketed out of his cock and into Gretchen's mouth. She swallowed as best she could while gagging on some of the tremendous output from Stewart's monster cock. Stewart finally relented and let go of the nurse's head. She pulled off as more cum shot all over her. The jizz that was log jammed in her throat flowed out of her mouth, covering her blouse and skirt.

Without saying a word, Stewart got up and removed the rest of his clothing. He then helped Gretchen up and began to undress her. In a matter of minutes he had her breasts in his mouth. He licked one nipple while he toyed with the other. His fingers probed Gretchen's wet pussy as she writhed on his digits. He placed her on the bed where he had been lying and got between her legs. His tongue worked over her lips and clit, while he probed her anus with one finger. Gretchen cried tears of pleasure and ecstasy and she felt her own orgasm beginning to build. Just as she went over the edge and started to shake with release, Stewart entered her. She was so wet, his large head and most of his shaft slid into her like two puzzle pieces perfectly fitting together. Unlike with Miss Martinez, Stewart took his time thrusting back and forth. Gretchen wrapped her legs around his waist and pulled him even hard into her. Still reeling from her initial orgasm, she yelped as another wave of climax rolled over her body.

Before she had time to catch her breath, Stewart rolled her over on her side and reinserted himself in her pussy. He also reinserted his finger in her ass and started pumping furiously. Gretchen squeezed her breasts as she received the fucking of a lifetime. Stewart moved with great speed, bringing himself to another ejaculation until his cock let go, filling the nurse's pussy with his cum. The two remained curled together with Stewart's cock still inside of her as they both nodded off.

~~~

A knock at the door finally roused Gretchen and Stewart from their sleep. An hour had gone by since they nodded off post-sex. The voice on the other side of the door was Vice-Principal Mason.

"Oh shit, Stewart. Grab your clothes and go in the bathroom. I'll tell her you were ill. Be right there. Just a moment."

"Don't worry, about it. I've got this." Gretchen threw on her clothes sans underwear, which she threw under the cot. She hurried over to the door as her boss knocked on the door again.

"Hi Vice-Principal Mason. I'm sorry for the delay, but I was with an ill student and didn't hear you right away."

"I was wondering if you were here, Gretchen. I passed this door 40 minutes ago and saw the "Be Back in 20 minutes" sign on your door. And, yet the sign was still in the window."

"Hi Vice-Principal Mason," said Stewart. I had a bad migraine and was throwing up. Nurse Gretchen really helped me.

"That doesn't look vomit on her face and clothes," Mrs. Mason said sternly. It was then that Gretchen realized that she hadn't cleaned up the cum that Stewart had deposited on her earlier.

"Oh that...that's from my lunch. I had soup and got a little sloppy."

"So sloppy it got in your hair?" Gretchen could do nothing but turn beat red.

"Why are you picking on her? She was a lifesaver. She relieved me of my headache."

"We'll see if that's all she relieved. Gretchen, I'll talk with you about this more later."

"Well, I have to get to class. Thanks again, Nurse Gretchen."

"Let me walk with you, Stewart," Mrs. Mason answered. As they walked, she quietly said, "It's obvious you fucked her. I know after this morning, I sound like a hypocrite, but you can't just go fucking everyone in the school...especially IN the school." Mrs. Mason wanted to say more, but she noticed Stewart getting hard again.

"For God's sake, Stewart. Can't you keep that thing calm?"

"Not around you, I can't. Come here." Stewart grabbed Mrs. Mason by the hand and pulled her inside the custodian's closet. Suck my dick Ali. You know you want to."

"Fuck you, Stewart, you bastard," Ali replied, but she dropped to her knees and had Stewart's cock out in no time. Short on time, she bobbed up and down on it as Stewart kept both hands on her head. While she stroked his cock with her right hand, her left hand massaged Stewart's balls, feeling them fill up with more of his seemingly endless supply of cum. A couple of minutes later that cum was making its way into her mouth and down her throat. She kept sucking until she had drawn out every drop and until Stewart stopped moaning from his climax.

"Now, I really do have to get to class, Ali. But, maybe, just maybe, I'll fuck you again before I go home." Ali could do nothing but stand there with her mouth slightly agape in reaction to the suddenly aggressive Stewart.

When it was time for gym class, it was Stewart who went up to Nancy and told her to meet him at the field house. Nancy excitedly agreed and found Stewart waiting for her when she arrived with the key. When they went inside it was Stewart who took control.

"Get naked and on all fours on the weight bench. I'm going to fuck the hell out of you." Nancy threw her clothes off as quickly as she could and got on her hands and knees as Stewart had commanded her. He squatted down behind her and started licking her pussy and shoved two fingers inside me.

"Oh my God, Stewart. Holy fuck."

"You haven't felt anything yet." Stewart continued to probe and tongue Nancy's pussy until she was good and wet, and then he pulled his pants down and slid his cock inside her. He pushed past her normal stopping point, stretching her pussy to the extreme. She cried out in pain and lust as Stewart slid more inches inside her. Finally, he grabbed her by the hips and started pushing and pulling her back into his body. His cock hammered away at her now accommodating vagina. Just as he had watched himself be edged, he now did some of the same to Nancy; slowing down as he felt himself get closer, teasing her pussy in the process.

"Stewart, please finish me off. Do it," Nancy pleaded as she fingered her clit to bring herself to an orgasm. Stewart suddenly sped up, smashing his balls into Nancy's ass as his cock pounded her leaking pussy. Finally, he howled and started firing one blast of cum after another into Nancy's opening. Her previously tight pussy took it in as if it were inhaling his seed. Stewart finally slowed to a trickle and removed his cock from Nancy well-worn pussy. He then commanded her to "Finish the rest." He slid his cock past her lips and deposited the remainder of his cum into her mouth and down her throat. When they returned to gym class, Nancy went into the girls' room to clean up the cum that was leaking down her leg. For Stewart, it was the best gym class ever.

On his way out of school, Stewart stopped by the office to tell Jeri and Ali, "I'll see you both at Jeri's on Sunday. And, you better be naked and wet when I get there." Both women were wide-eyed and open mouth. "Oh, and Ali, this time I'm going to take your ass." Ali felt herself get instantly wet.

As Stewart headed to the school bus, a small sedan pulled up in front of him. It was Emmy. Stewart grimaced at the sight of her.

"Stewart, can we talk?"

"Why?"

"Because, I really want to apologize to you for the way I acted."

"There you go. You just apologized."

"That wasn't a real apology. Could I give you a ride home and we could just talk? I promise I won't do anything stupid." Much to his chagrin, Stewart agreed and got into Emmy's car.

The two talked quite a bit on the ride. Well, mostly Emmy talked and Stewart listened. She talked about how unhappy she was and that she really didn't want to be a ballerina. Her parents wanted her to be. She wanted to be a doctor and had secretly applied to several schools to major in pre-med. Always an empathetic person, Stewart felt differently towards Emmy...more like the way he used to feel about her.

"I'm really sorry you're going through all that, Emmy. Have you tried to explaining your feelings to your parents?"

"I've tried, but I have been too chicken to really tell them the whole truth. I can just image the disappointment on their faces."

"Maybe, but maybe not. Maybe they think you really want to dance and would be ecstatic to know you want to be a doctor. I mean, what parent wouldn't want their child to be a doctor or lawyer? Okay, maybe not a lawyer." The two laughed together.

"Hey, would you like to stop for a burger or something? On me."

"That sounds nice, Emmy. Okay."

The two stopped at a diner and sat in a booth in the back. They ordered some cheeseburgers and fries and talked more while they ate.

"Um, you have some ketchup on the side of your mouth, Em."

"Where?" Stewart was about to point it out, but suddenly felt compulsive and licked it off Emmy's face. Before he could lean back to his seat, Emmy lunged forward and their two locked lips. They tasted the ketchup and salt from the fries on each other's tongue. Stewart got up and came around the booth to sit next to Emmy, where they continued to make out.

Stewart whispered in Emmy's ear, "Take off your panties." Emmy immediately started breathing hard.as she reached under her skirt and pulled her red panties down. As they kissed more, Stewart reached underneath her skirt, and inserted two fingers in Emmy's damp vagina. Emmy gasped in response. His fingers probed inside of her while his thumb began to play with her clit. Emmy kept watch to be sure no one was approaching, but she was having difficulty keeping her eyes open with the sensations that were taking over her body. With his tongue deep inside her mouth, Stewart started to seriously fuck Emmy with his fingers. She bit down on a napkin as her pussy squeezed his fingers in response and she shuddered as she came. Stewart continued to thrust his fingers inside her, extracting all the juice he could. When he finally finished, he pulled his fingers out and inserted them in Emmy's mouth. She sucked his digits like a popsicle, tasting all of her juices. They then kissed and Stewart could taste her on her lips and tongue.