Pajama Day

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Friday was Pajama Day; the last day of Spirit Week. Some boys like to make various bets or dares about what they could get away with wearing on Pajama Day. The reason being that several years ago one kid’s mom sued the school after they tried to say she can’t send her son to school wearing nothing but his briefs. She said she could not afford to buy him pajamas. She argued that it wasn’t any different than the swim team wearing their speedos all day for School Pride Day. School Pride Day is the first day of Spirit Week. You are supposed wear the school colors, or if you participate in a sport you just wear your uniform. The boy’s mom won the lawsuit, now kids are allowed to wear their underwear on Pajama Day.

Allowed being the key word. Most kids don’t want to go to school in their underwear. Most kids only do it if their parents make them. Every year more and more parents force their kids to participate. This leads to more and more kids rebelling by doing whatever they can to test the limits of Pajama Day.

16 year old Ryan was walking to the bus stop wearing nothing but plaid boxers, socks, shoes, and backpack. His 10 year old brother Cody was walking with him wearing nothing but flip-flops, black Batman themed briefs, and his backpack. Their parents are making them participate in Pajama Day as punishment for not keeping the room they share clean. Ryan had a dare going with his best friend Sean. They would each bring a pair of underwear for the other to wear and they would trade on the bus. Ryan brought a pair of his little brother’s cartoon briefs to give Sean. They were “The Flash” themed, red with a lightning logo on the crotch.

At the bus stop Ryan started to wonder if his crush Vanessa would be wearing her underwear. Just the idea of it was enough to make his dick twitch. That’s when his friend Sean showed up with his little sister. Sean was wearing nothing but blue briefs that had a white waistband, sandals and his backpack. Sean’s little sister was 7 years old. She was wearing nothing but My Little Pony panties and pink slippers. Being a little girl she didn’t actually need or own any bras. Ryan knew it was unlikely she wouldn’t wear a bra, but he imagined his crush Vanessa wearing nothing but panties to school. The thought of it made him rock hard. His cock tented up his boxers. He looked down to make sure it wasn’t poking out of his fly for everyone to see. At 16 his body was almost fully mature and his cock was biggest of all of his friends, 8 and half inches. There was no hiding his huge boner while he was wearing nothing but boxers.

“I see you are excited about today”, his friend joked while pointing at his boner. Thus calling attention to it for all the kids at the bus stop.

Sean was his best friend since elementary school. Sean came out of the closet a couple years ago and Ryan didn’t care at all. Even though Ryan is completely straight, the two of them sometimes jack off together. It was something they started doing when they both joined the baseball team when they were 12; after the entire team had a circle jerking competition.

Once they were sitting on the bus, Ryan took out the underwear he brought for Sean to wear, his little brother’s “The Flash” briefs. Sean smiled, he took off his own briefs and threw them out of the window of the bus. Then he put on the underwear that belonged to Cody. He was just barely able to squeeze them on, the 10 year old kids underwear looked both tiny and ridiculous on him. Without even waiting to receive the underwear his friend brought; Ryan took off his boxers and threw them out the window. He was now sitting on the bus completely naked except for his shoes and socks.

“I can’t find them”, Sean lied while rummaging through his backpack. Ryan trusted his friend completely; but considered that Sean may have accidentally forgot the underwear and that he was stuck naked, the idea made his dick twitch. Ryan imagined still being naked when the bus stopped at the next bus stop. The other kids would board the bus and see him, including his crush Vanessa. Once again he fantasized about her boarding the bus wearing nothing but a pair of panties, and him being naked. The idea made his cock rock hard. Sean smiled and then he finally pulled the underwear out of his backpack. It was a jockstrap.

Neither boy knew if Ryan would get in trouble for wearing a jockstrap to school. The whole purpose of their dare was to test the rules about wearing underwear to school. Ryan took the jock strap and held it up in front of his erection. The pouch was maybe 4 inches, and the waistband another 2. Thus leaving two and half inches of cock still poking out past the waistband.

“Dude, this is never going to fit me while I have a boner.” said Ryan before placing the jockstrap down on the seat.

“Are you backing out?”, asked Sean as he pointed out the window reminding him that his boxers were long gone.

“No, don’t worry.” said Ryan as he grabbed his hard cock and starting jacking off right there on the bus.

He imagined jacking off with Vanessa watching. She might like watching and get so turned on that when he came, she would offer to help him clean up by eating his cum.

“Do you ever jack off in front of your little brother?” Sean asked, knowing that they shared a bedroom.

“Yeah man, all the time”, Ryan answered honestly.

“Do you like my little brother?”, asked Ryan.

“What?”, Sean blushed.

“Do you want to fuck my little brother?”, Ryan asked bluntly.

“It’s cool with me if you want to fuck him. I think he is gay too and he is always asking me if you have a boyfriend.”

Sean didn’t answer, he began to fantasize about playing video games with his Ryan while his little brother Cody sucked his cock. The idea made him hard and his cock poked out from the briefs he was wearing; which belonged to the same ten year old. Sean pushed the front of the briefs down and pulled out his cock; and started jacking off along with his friend. Sean’s cock was not as big as Ryan’s but at 7 inches it was still above average.

“You think he is gay?”, Sean asked.

“Yeah, he loves watching me jack off. He always asks me when I’m going to do it again and begs me to wait until he gets home from school.” Ryan admitted.

This wasn’t the first time Ryan jacked off on the bus ride to school. However, he usually just pulled his cock out of the fly of his pants. Somehow, sitting there wearing nothing but shoes and socks made it even more enjoyable than usual.

At the moment, they were sitting in the back seats and nobody was sitting in the seat next to them. Ryan was trying to hold out. He didn’t want to cum until he got to see what Vanessa was wearing. He was hoping she might come to the back of the bus, that she might see how big his dick is and beg him to fuck her. The bus stopped. Sean tried to shove his cock back into the briefs; but they were way too small and his cock continued to poke out. Ryan stopped jerking off but made no attempt to hide his nudity. He leaned his head into the middle of the isle to watch for Vanessa.

Vanessa got on the bus. Ryan was disappointed that she was wearing pajamas; and not her underwear like he had been hoping.

“Vanessa!”, Ryan shouted while pointing to the empty seat next to him at the back of the bus.

His desire to see girls naked was equal to his desire to be seen naked by girls. He reasoned that if girls could just see that he had a big dick; that they would want it inside of them and he would finally lose his virginity. Vanessa waved at him but pointed at her sister, letting him know she intended to sit with her.

“You are so lucky you are gay. It’s so much harder to get with girls.” Ryan complained to his friend as he resumed jerking off.

Sean followed his friend’s lead and started jacking off again too. He needed to get rid of his erection before they got to school. There was no possible way to hide his boner fit in these tiny cartoon briefs.

Ryan was getting close to cumming. He realized he didn’t have anything to clean up his cum with. Normally he would just smear it all over his chest and let it dry. His shirt would hide it and then he could wash it off in the shower after P.E. Ryan fantasized about Vanessa watching him cum. He imagined making a big mess and then her politely offering to remove her pajamas and offer them to him to use as cum rags.

“I’m cumming”, Ryan announced loud enough that kids could hear 3 seats away.

One shot of cum landed on his shoulder. Then he shot another 4 big loads on his chest. Another 2 landed on his abs. After that; cum continued to leak out of his cock over his fist and down his shaft. That was one of the best orgasms he ever had. He would definitely get naked and jack off on the bus again in the future. He picked up the jockstrap and wiped the cum on his hand into it. The pouch was so small there was no way he could use it to clean up the rest of the cum.

Having heard Ryan announce his orgasm, a boy sitting in the seat in front of him turned around to see. The boy was 14, he was wearing boxer briefs and a t-shirt. Ryan looked up and made eye contact with the boy. Then he looked back down and scooped the cum running down the shaft of his cock and began smearing it over his chest with the rest of the cum.

“Hey kid, can I use your shirt?” Ryan looked back up at the boy and asked.

“Why?”, the boy asked.

“I made a big mess.”, said Ryan.

Without breaking eye contact Ryan reached down and started smearing around the cum on his abs. The boy took off his shirt and gave it to Ryan. He had wanted to wear just his boxer briefs anyway. He only wore the shirt because he wasn’t sure how many other kids would participate in Pajama Day in their underwear.

Ryan thanked the boy and started using the shirt to wipe up the cum off his body. He was relieved. He already might get in trouble for showing up to school wearing a jockstrap, he would really be asking for trouble if he was walking around covered in cum too. He just wished he didn’t already use the jockstrap to clean some of it up. Now he was stuck wearing a cum stained jockstrap all day.

Sean was still jacking off. He imagined spending the night at Ryan’s house during the summer. He would be sitting on the couch watching T.V. with Ryan and Cody, the three of them would be in their underwear. After their parents left, 10 year old Cody would come sit on his lap and the two of them would start making out. He would yank off the little boy’s underwear and then shove his tongue into the boy’s mouth. As they kissed he would pull his own cock out of the fly in his briefs.

Then he would turn Cody around and have him slowly sit down on his cock. The 10 year old boy would start to cry and say Sean’s 7 inch dick is too big for him. Ryan would would get angry and tell his little brother to shut up. He would whip out his own dick and start jacking off. Once he was fully hard he would hold it in front of his little brother’s face and remind him that some boys had even bigger cocks. He would tell Cody how lucky he is to be gay and have a boyfriend like Sean. Secretly, Ryan would be jealous that his little brother was losing his virginity before him.

Ryan would continue jacking off and shoot cum all over his little brother’s face and hair. Ryan wouldn’t get any sexual gratification from watching his cum drip down his little brother’s face, he was straight. He would do it simply to humiliate and bully his little brother. He would do it assert his dominance because he was insecure about being a virgin. Sean never came as quickly as Ryan did. He would continue to fuck the little boy for another 20 minutes. By that time Cody would have started getting used to the pain caused by being impaled on Sean’s adult sized cock; but Sean could still make him grunt if he pulled all the way out and let the boy’s sphincter close before shoving his cock back inside him. Sean would cum directly inside the boy’s tight hole. By then, his older brother’s cum would have dried on his hair and face.

After that day, Ryan would trick Cody into being his slave all summer. He would threaten to tell their mom and dad about how he was having sex with his boyfriend while they were gone at work. Being the goody goody he was, Cody would actually be worried about getting in trouble for having sex with Sean. Cody would clean their room for him, bring him snacks, etc.

Back in reality though, Sean was just jacking off on the bus. Ryan’s cock had finally got soft enough that he could put on the jockstrap. Sean imagined making Ryan’s little brother wear a jockstrap so he could fuck the kid without even having to take his underwear off. The idea thought was enough to make him start cumming. Just in time too; the bus was pulling up to the next stop and more kids would be getting on the bus. Sean used the same shirt Ryan did to clean up his cum and then he tossed it out the window.

As the day went on, more and more boys were walking around with erections. There was no way to hide them when they were wearing just their underwear and shoes around school. Altogether, the first half of the day was pretty uneventful. Ryan didn’t get in trouble for wearing a jockstrap. A kid named Carl lost a bet with his girlfriend, he was wearing his girlfriend’s panties and continues to be the center of attention.

Lunch time was the first chance any of them had to jack off. There was a line to use the bathroom stalls. After the toilet paper ran out some guys started coming out with obvious cum stains on their underwear or just leaving the cum to dry on their chests and stomachs. One boy who was wearing plain white boxers pretended to “accidentally” pour a bottle of water onto his crotch. Causing the fabric of his boxers to become almost completely transparent. All his friends thought it was hilarious.

In P.E. all the girls were swooning over the P.E. teacher Mr. Conner. He was one of the few teachers brave enough to participate in Pajama Day wearing his underwear. Which wasn’t surprising at all because he had an amazing physique. Even when he was wearing a shirt you could see his chest muscles. Today he was wearing nothing except sunglasses, shoes, and microfiber white briefs. They had no fly, they would look like speedos if not for the silver waistband. The material however was much thinner than speedos. Even though he was completely soft you could see the outline of his dick through them.

Today, the class was going outside to the football field to do stretches and warmups.

“Ryan!” Mr. Conner pointed and called him to the front of the class.

“What’s that stain?”, Mr. Conner asked while pointing at his jockstrap.

“It’s cum”, Ryan answered honestly and loud enough for the entire class to hear.

“Lead the class in warmups”, Mr. Conner instructed.

Ryan was happy to oblige, he loved being the center of attention. He was also happy because it meant he could better watch the girls boobs bounce up and down while they did jumping jacks in their underwear. Unfortunately, Ryan enjoyed it too much. Jacking off on the bus helped prevent him from getting an embarrassing erection all day until now. He could feel the blood pushing into his dick. Once his 8 and a half inch cock was fully hard, There was literally no way to contain it within the tiny pouch of his jockstrap. In the middle of doing jumping jacks, his cock pushed its way out of the pouch of his jockstrap and began to bounce up and down, making an audible sound as it slapped against his abs and thighs.

Once half the class and started laughing Mr. Conner appeared at his side looking straight down at his bouncing cock. Ryan wondered whether or not he was about to get in trouble for having an erection. He saw guys all over school with boners and they didn’t get in trouble. Then again, their dicks were not physically sticking out of their underwear like his was. It wasn’t his fault his cock was so big it couldn’t fit inside his jockstrap. He secretly hoped that Mr. Conner would tell him that his boner poking out in front of the girls was obscene and demand Ryan get rid of it. Ryan would love nothing more then to be forced to jack off in front of the entire class.

Mr. Conner honestly had no idea how to handle the situation. Like all the other teachers the principal warned him not to do anything that would get the school sued again.

Mr. Conner lifted up his sunglasses, pointed straight at his cock and asked, “Ryan, Would you like a bathroom pass to go take care of that.”

Ryan realized that his teacher was giving him permission to go jack off in the bathroom, not make him do it in front of the class like he hoped. He decided however, that he would rather keep his hard cock exposed for all the girls to see. Maybe one of them would tell his crush Vanessa how big it was.

“No thanks.”, Ryan responded.

It wasn’t until now he realized his teacher had a boner too. It was pointing sideways along his hip. His microfiber briefs were so thin that you could actually see the veins on his shaft and the fact he was circumcised. He wondered who had a bigger cock, him or his teacher. They looked about the same length but his teachers cock looked monstrously thicker. He considered that if he were to hold the shaft; it would be too thick for him to be able to close his palm around it.

He felt compelled to take out his teacher’s dick and hold it next to his own. Not because he was gay. It was because his own dick was a source of great pride for him and he was extremely competitive. He wanted to be able to prove he had a bigger cock, or at least a longer one.

Mr. Conner decided not to push Ryan. He could only imagine the trouble he might get in if he tried to force a student to go masturbate. What Ryan didn’t know is that Mr. Conner is bisexual. Although he was fully able to enjoy the girls boobs bouncing up and down during the jumping jacks; most of the time he prefered boys. Boys were so much easier than girls. Plus he could fuck boys without worrying about getting them pregnant. As the P.E. teacher he had the added benefit of being able to watch all the boys get naked and shower after class. Mr. Conner knew that Ryan’s best friend Sean was gay. He secretly hoped that Ryan was bisexual like himself and that maybe the two boy’s sucked each other’s cocks.

Mr. Conner wanted to keep the girls boobs and the boy’s cocks bouncing. So for their first exercise he instructed everyone to run up and down the steps on the bleachers. The stairs wouldn’t fit all the students so he made the girls go first. By the time it was the boy’s turn, most of them had boners. The boys who were wearing boxers couldn’t do anything to prevent their boners from popping out of the fly as they run up and down steps.

Mr. Conner thought back to lunch time, he asked the Principal in the break room what to do about the boys walking around with boners, dry cum on their chests, and wet transparent underwear. The Principal said was that he was on thin ice with the Superintendent and that he couldn’t suspend kids for getting erections, being dirty (refering to the cum), or accidentally spilling water.

Mr. Conner casually mentioned how hot it was outside before picking up a bottle of water and pouring it over his face, then his chest. Most of it ran down his body soaking his briefs. The thin white material became completely see-through. Ryan became jealous of the attention his teacher was stealing from him.

On some boy’s underwear, you could see wet spots from the boys who were leaking pre-cum. Most of the class waiting for waiting for one boy to come back with the bathroom pass so they could have a turn to go masturbate. Having realized what was happening, Mr. Conner released the class 20 minutes early so everyone would have a chance to relieve themselves.

In the locker room some boys were jacking off while sitting down on the benches by the lockers. Ryan again decided not to masturbate. He wanted to keep his boner as long as possible so all the girls in school could see it, or more importantly, how big it was. He put his jockstrap and shoes in his locker and went to the showers.

The showers were the kind where there is a pole in the center with 6 nozzles at the top. This meant all the boys would be facing each other with no privacy. Ryan was the only one not jacking off. He was reminded of when the baseball team had a circle jerk and how happy he was to find out he had a big dick. Even when he was 12 he was bigger than most of the older boys on the team. His teammates nicknamed him bat boy. Sometimes the team has him take his cock out and make it hard, then they throw stuff and he would swing his cock at it as if it was a baseball bat. Sean has a video on his cell phone of him doing it in his baseball uniform that he shows guys around school all the time.

As he was about to finish his shower, Mr. Conner approached him and told him to follow him. Ryan was nervous he was in trouble. His teacher led him to his locker and told him to put on his shoes and socks. As he sat on the bench naked ties his shoes, Mr. Conner explained that he Principal wanted to see him in the auditorium.

“Am I in trouble?”, Ryan asked.

“Not exactly.”, Mr. Conner explained, the Principal was having a special gathering in the auditorium to get a picture for the school year book. The Principal wanted to humiliate the boys who were testing the rules. He hoped to make example out of their embarrassment that would stop anyone from “testing” the rules next year.

Mr. Conner explained that he knew a secret, there was only one rule the Principal could legally enforce, and he was scared one of the boys would figure it out. That rule was that underwear must be worn on the genital region. The legal wording was to prevent kids from going naked by wearing their underwear on their head. As he explained this, Mr. Conner took Ryan’s jockstrap out of his locker and hung it by one strap over his hard cock. Then he held Ryan’s shoulder and led him out of the locker room. He gave the boy a hard spank on his bare ass and told him to go to the auditorium.

Ryan entered the auditorium with his jockstrap simply hanging from his hard cock and told the Principal he was ready for his picture. The other boys were laughing and the Principal turned red with anger knowing Ryan was not breaking the rules.

Ryan and all the other boys the Principal called posed together for a picture for the yearbook. Knowing Ryan didn’t get in trouble; other boys around school took off their underwear and let them hang from their boners. Ryan became very popular and that same day Vanessa asked him if he wanted to be her girlfriend on the bus ride home from school.

10 year old Cody came out of the closet when he got home from school. Telling his parents all about how much he liked seeing other boys in their underwear at school and how he had a crush on Ryan’s best friend Sean. His parents were thrilled, they always liked Sean. They told Ryan to invite him over that same night so Cody could tell him. Sean said he liked Cody too.

They asked Cody if he wanted to have sex with Sean and he said yes. Their mom asked if she could record it so the whole family could watch Cody lose his virginity. Their dad told their mom that she was embarrassing him, they should wait until Cody can deep throat Sean’s cock first so it looks more impressive on video. Their mom asked Sean if he wanted lubricant. Their dad said, no lubricant, Cody was still in trouble for not keeping his room clean.

(End of File)