School Over-nighter

[RlAcct]

Prologue:

Stephanie was a quiet 18 year old and a typical nerd, glasses, blonde hair tied in a ponytail and dressed extremely conservatively. However, unlike her outward appearance, she had a wild mind with an obsession of seeing someone of the opposite gender naked. Due to her quiet demeanour she has not had much luck interacting with any boys her age, at 18 boy are more focused on girls who are less intelligent and show more skin, or so she tells herself.

Like most Fridays she was staying late after school, today she was helping the new gym teacher, Ms. Graham, a young and athletic woman clean her office for extra credit. As always, Stephanie was early, so she was waiting outside her teacher's door which was across the hall from the boys locker room. However, unlike every other time she's had to wait there, today the door to the boys locker room was ajar and she could hear a shower running. Intrigued, she approached the open door and, much to her amazement, she was able to catch a glimpse into the changing area from where she was standing. As if someone else was controlling her body, she quietly poked her head into the locker room and she could now see a boy in the showers, a naked boy! Granted, he seemed to be a bit younger than her, probably around 16, but she wasn't going to complain about that. Unfortunately for Stephanie, the boy, Tom, was standing behind a 3 foot tall privacy wall which covered the parts she wanted to see most.

Tom seemed athletic, however he was short and very skinny, he was a late bloomer and part of the cross country team which is why he was showering after classes were over. He was also extremely shy which is why he was alone in the locker room, he got permission from his coach to shower after the rest the team had finished changing as he didn't want to be seen in any state of undress by his peers. He would always ensure the door closed behind him after entering the locker room however today the door didn't click shut and he didn't notice as he was in a rush. He quickly got undressed as the door crept open, leaving his towel on a hook on the wall across from the showers and hurriedly started shampooing his hair.

Stephanie was staring in awe and wished the wall was a foot shorter but she would take what she could get. Tom had his eyes closed so he did not notice Stephanie and, almost reflexively, Stephanie pulled out her phone and took some pictures. She got some pictures of him rinsing off from the hips up and much to her luck, he only opened his eyes after he turned away from the door, allowing her peep show to go on longer. Having finished showering, Tom turned off the water and walked towards his towel to dry off, meaning he was no longer behind the privacy wall. Stephanie almost let out an audible gasp, she was able to get a few pictures of him fully naked from behind. She was silently hoping that Tom would turn around and she would have pictures to commemorate the first naked boy she had seen, however, she heard Ms. Graham’s keys jingling from around the corner which she took as a cue to put her phone away and run back across the hall. Ms. Graham breathlessly ran over to Stephanie and apologized for being late, as she always did, and as they begun chatting, Stephanie caught a glimpse of Tom rushing to slam the locker room door shut as to maintain his privacy causing her to smile at the futility of his actions.

Over the next few days, Stephanie shared the pictures she took with her three closest (and only) friends, hoping one of them would recognize him so they could find him and try to encourage (blackmail) him into showing more. Unfortunately for them, seeing as they are a quiet group of nerds, Tom is a loner, and they are two grades apart, they hadn't been able to located him. With the thought of finding this mysterious naked boy pushed to the back of their minds, they signed up for the school over-nighter which occurs every year before spring break. This event allows students to bond outside school hours or, in the girls' case, get to spend all night in the library reading and gossiping. Little did they know that the sleepover this year would be for more eventful for them than it has ever been in the past.



Chapter 1: Crime and Punishment


Tom was excitedly getting ready for school today, it was the night of the school over-nighter, which means a full night access to the school's gym. He quickly got dressed, sporting his new pair of boxers that he finally convinced his mom to get him, packed his sleeping bag and backpack and left for the day.

After an uneventful day of classes, he rushed to his locker as soon as the bell rang to grab his sleeping bag and pyjamas to set up his sleeping quarters in the weight room. Unsurprisingly, to avoid any mischievous activities, the boys and girls had to sleep separately in the weight room and library respectively, which made no difference to Tom as he was too shy to talk to girls anyway. Once his sleeping bag was set up, wanting to save time later, he changed into his pyjamas now, baggy flannel pants that he wore over his boxers, comfy socks and an oversized T shirt which came down to about mid thigh, and headed back to his locker to put away his clothes.

After dropping off his belongings, he started running towards the gym to get an early start on training, as he rounded the corner he ran head first into something soft which made him stumble backwards. This something just happened to be the chest of an older girl at his school, a girl named Stephanie, who was heading towards the library with her friends. Tom began to get up, flustered and blushing at the events that just transpired, apologizing profusely, where as Stephanie was too busy analyzing the boy before her. Tom started to head off once again before he was stopped.

"Hey wait, you look familiar, do you have any siblings in my grade?" Stephanie inquired.

"N-no, I don't have any siblings" Tom managed to stutter out.

Stephanie continued to stare at him then something clicked. Her eyes went wide and she began to blush, "Hold on a second, l want to show you something". She pulled out her phone and opened her camera roll, scrolled a couple times and turned the screen towards Tom. "Does this boy look familiar to you?" she asked while grinning widely.

Tom looked at the phone then back to Stephanie and he went pale, it was a picture of him, but not a picture he thought even existed, a picture of him completely naked from behind, towelling off his hair, in the school showers. "Wha.. where, how-" Tom was cut off.

"That doesn't really matter right now, does it? The only thing that you need to care about is what I want, and what that is, is more. I was nice enough to keep this to myself and my friends here, you're welcome, and if you want it to stay that way you need to do something nice for me." Stephanie informed Tom.

Tom just stared at Stephanie, his throat too dry to respond.

"It's quite simple really, all I need you to do is to pull down your pants and underwear, pull up your shirt, and let me get a picture of what's between your legs. Because I'm so nice I won't even get your face in the picture so it will be anonymous, only I will know who's boy parts are in the pic."

"There's no wa-" Tom began to protest.

"Or I could get my friends here to help me strip you, take all the pictures we want and send them to anyone we please, the choice is yours. Also, if you run I'll send the pictures I already have to everyone I know."

"...ok, I'll do it"

"Amazing, go ahead whenever you're ready" Stephanie said as she took a knee and opened the camera on her phone.

Tom slowly pulled down his loose pyjama bottoms to his mid thigh, about where his shirt ended and looked down at Stephanie who gave him a thumbs up while her friends behind her let out a small laugh.

"You promise you'll keep this to yourself?" Tom asked, his voice quivering slightly.

"Absolutely" reassured Stephanie as she put her phone closer to Tom's pelvis.

Tom began to lift his shirt, bringing his boxers into view and he heard a click from Stephanie's phone, he swallowed hard and hooked one thumb into his boxers as he kept his other hand on his shirt to keep in from falling. Stephanie and her friends who stood behind her were all entranced staring at Tom, they were so focused you could hear a pin drop. Stephanie absentmindedly moved her phone even closer and that's when Tom made his move, he let go of his shirt letting it fall into place and used that hand to grab Stephanie's phone, pulling up his pants with his other hand as he turned to run. He sprinted down the hall much too quickly for the girls to keep up with him, the first time all his practice for track came in handy, around the corner, past a few older boys and made it all the way to the weight room, where he hoped he would be safe from the girls while he deleted the pictures of himself.

Unfortunately, with his hasty movements, Tom had locked Stephanie's phone when he was trying to make his get away, at a loss of what to do, he stood there trying to guess her passcode, after several unsuccessful attempts he locked the phone for a minute. While he was waiting for the phone to unlock he felt a pair of hands grab the back of his shirt and pull it over his head, obstructing his view and then taking the phone from his hand. Immediately after, someone hit him in the gut causing him to double over right as a third person put him in a head lock. Before he could say or do anything Tom heard an older boy's voice.

"Trying to steal Stephanie's phone, eh?" the boy said. "Not the brightest idea with so many witnesses around." he continued.

"I wasn't, I-I didn't-" Tom managed to stammer out.

"Oh so this is your phone in the pink case with a picture of Stephanie and her friend's as the lock screen then?" The unknown assailant retorted, "I think you need to pay for your crime" the boy said as he started dragging the blindfolded Tom forward.

After a few steps, what little Tom could see though the fabric of his shirt got brighter, meaning they probably went though the doors of the weight room and were now in the hall.

"I believe this is yours" one of the other boys said.

"Oh my god, thank you so much." Stephanie said, her voice quaking as though she had been crying.

Right after Tom took off, Stephanie gave chase for a bit but quickly realized that catching him was a lost cause. She started panicking because he now had proof that she blackmailed him. She stood there thinking a moment before she heard her saviour speak up.

"Yo, you alright?" Alex, a jock from one of her classes asked.

Using her quick wits, Stephanie knew how to turn this situation around, "That boy just stole my phone" she cried out and, on cue, tears began running down her cheeks.

"Damn, well he couldn't have gotten far, we'll catch him don't worry" Alex said, who then took off followed by his two friends as Stephanie grinned to herself and followed along slowly.

Now, surrounded by three older boys that towered over him, in a headlock, with his shirt flipped over his head, blinding him, Tom had no recourse. Just as he was about to let out a desperate plea, one of the boys, Max, grabbed the waistband of his boxers and gave him a wedgie. What Tom was gonna say came out as a yelp instead as this was not only unexpected but also the first time in his life someone had given him a wedgie.

Stephanie and her friends were giggling amongst themselves, it was quite a spectacle seeing a boy completely overpowered with part of his butt on display from having his underwear pulled out of his pants. With her phone already in hand, Stephanie began recording the scene unfolding in front of her, which was noted by Mike, the third boy who was not involved in this display thus far. Not wanting to be shown up, he walked over to Tom and in one fell swoop, tugged his pants down to his ankles. This made the girls all gasp and laugh even louder.
"Ok! Ok! Please, I'll never steal again" Tom plead "I've learnt my lesson, I'm sorry!"

"I don't know, the girls don't seem to think your thievery has been atoned for yet" Alex retorted.

"Yeah make 'em pay boys!" one of Stephanie's friends called out.

Just then, Max pulled harder on Tom's waistband, lifting him off the floor and causing Tom's body to tilt forward slightly as his head was firmly held in place by Alex. With this movement, more of his butt came into view making Tom panic profusely, not only is he restrained and unable to see who is looking at his butt, but if this keeps up he feels as though he may fall out of his boxers! Mike joined Max's effort and pulled Tom up even higher while Alex began to slowly walk forwards, putting Tom's full butt and the beginning of his thighs on display. Stephanie got in close with her phone practically sticking it down the back of Tom's pants, filming all that she could, so that she could keep this memory forever.

Tom tried to plead one more time "Please, guys, please, I'm going to fall out of my boxers, please-"

"What the hell is going on here?!" Ms. Graham's voice rang out.

Just then, Tom was dropped by the three boys and he was able to quickly pull up his pants and finally uncover his eyes, catching a glimpse of the boys who carried out his punishment running for the hills, Stephanie and the girls she was with nowhere to be seen as they must've made a break for it earlier hearing the jingle of Ms Graham's keys approaching.

"Are you alright?" Ms. Graham asked.

"Yes... Thank you" Tom said holding back tears.

"I've got to go deal with those boys, go to the gym and wait for me, we can talk about what happened in my office" she said right before taking off after the three boys.

Tom just sat there for a while processing what had just occurred and while he was horrified that an unknown amount of people had just seen his get humiliated, he couldn't help but also be upset that his new boxers had just been fully stretched out and rendered practically unwearable. After taking a moment, Tom got up and slowly headed over towards the gym, this was going to be a long night.

[TeenFan]

This story could go in any direction.
Poor Tom is in trouble with both boys and girls, and he just got there. A long night indeed.

[RlAcct]

Chapter 2:

After getting to the gym, Tom sat down on a bench and just kept going over the events that had just transpired as he blankly stared at the few students that were in the gym playing volleyball across from him. Several minutes went by and Ms. Graham was still no where to be seen while Tom just sat there and continued to wait, he didn't want to risk running into those older boys again, the kids that were playing had slowly trickled out and once the gym was empty three older girls enter the gym, laughing amongst themselves. One of the girls and Tom locked eyes causing her to freeze for a moment before catching up and whispering to her friends causing them the briefly glance towards him, but Tom didn't really notice, he was too distracted by the gym attire these girls chose to wear. The girl he locked eyes with, a red head with curly hair was wearing an oversized sweater and biker shorts, another girl had blonde hair and had great assets, she was sporting leggings and a crop top and the third girl, a petite brunette was wearing a sports bra and short shorts. These clothing choices weren't anything overtly revealing but seeing as Tom didn't normally interact with girls, especially older girls, it was enough to garner his attention and let his mind wander. The girls stretched and warmed up, looking like they were gearing up to play a game of volleyball when one of them beckoned in Tom's direction, snapping him out of his trance.

"Hey, we'd love to play a game but were waiting on one of our friends, could you fill in for the time being?" the ginger girl asked with a bubbly air. With slight apprehension, Tom got up and headed over.

"S-Sure, I can play for a bit" Tom responded hesitantly.

"Amazing! I'm Lisa by the way and those two over there are Anne-" she pointed to the blonde who waved back "and Liz" gesturing to the brunette who smiled at Tom which made his heart flutter. "I'll serve!" Lisa said, and the game began. After a few rallies Tom began to let his guard down, actually having fun and focusing on something besides the humiliation he just endured, after jumping up and spiking the ball over the net Lisa spoke up.

" What's you name by the way?" she asked.

"Tom" he responded.

"You play any sports?

"Just track, you?"

"I'm on the wrestling team. How old are you?"

"Cool, I'm 16, what abou-"

"Wow you can jump pretty high for someone your age, you must have really nice butt muslces" Anne spoke up, this caused the girls to giggle and Tom to blush.

"Yeah, you can jump so high, it almost looks like you're being lifted up by two older boys" Liz chortled. That's a strange thing to say Tom though to himself as he listened to the girls laugh amongst themselves. Just then, it hit him, the odd comments and the all too familiar sounding laughter caused him to make a horrifying realization, these girls that he's been playing with the past few minutes are Stephanie's friends! He had only caught a short glimpse of them during his first encounter with Stephanie as he was too focused on making a break for it as soon as he could, and the second time he encountered them, his eyes were covered. But their laughs, he recognized their laughs from when he was being tormented earlier.

"Wait, are you guys-" was all he managed to get out before having his pants hauled down to his ankles from behind, his boxers came down to his mid thigh too as the elastic was rendered all but useless from the older boy's earlier efforts.

"Ah there you are Steph!" Lisa said "We had to make due with lil' Tommy while you were changing". Tom bent over to pull up his pants but as he did, Stephanie flipped up the back of his shirt and gave him a smack on his bare butt causing him to shoot up straight. While standing Tom noticed that Liz was recording yet another humiliating moment he was experiencing however he was thankful that his shirt was long enough to keep him fully covered.

"That was for not making it easy for everyone and running earlier. Now, I believe you owe me and my friends a viewing and pictures of your boyhood" Stephanie said, relishing the power she has over him. Tom pulled up his boxers and turned to face Stepahnie to tell her off, but as she saw this act of defiance winding up in front of her she simply placed one foot on his pants which were at his ankles and gave him a hard shove causing him to stumble backwards out of his pants. Stephanie picked them up and tossed them onto the volleyball net causing all the girls to errupt into a new fit of laughter while Tom, wasting no time, quickly got up and started to head towards Stephanie and his pants. He didn't make it far however, he was stopped in his tracks when Lisa gave a quick tug on his boxers, taking them partway down, causing him to grab at them to keep them from calling to his ankles. As Tom began pulling desperately to keep his boxers on, he realized that where he stood right now he was surrounded by 4 girls who's collective goal was to see him naked, so he started backing away from the other three while Lisa followed him with a tight grip on his boxers and Liz in toe, not wanting to miss the potential shot of a life time.

While retreating, he actually began making progress in the tug of war for his boxers, however, this victory was short lived as all it did was cause Lisa to change tactics. She quickly released his boxers, allowing Tom to pull them up, but immediately began pulling up the sides of his shirt. Not wanting to be left only in a pair of ill fitting boxers, he switched his focus, grabbing the front of his shirt and pulling it down to keep himself covered. The lack of support of his undewear mixed with the fact that he was walking backwards caused his boxers to slip partailly down his legs but there was nothing he could do now, if he let go of his shirt to pull them up he would be fully exposed to Liz's phone, giving the girls a naked video of him to spread around the school. So, he did the only thing he could think of, he kept walking as his boxers slipped down over his shoes and fully off his legs. This caused all the girls to once again laugh at his misfortune while he maintained the front of his shirt firmly in place. Once again, Lisa took this as a cue to switch up her approach, with both of Tom's hands planted firmly on the front end of his shirt, she reached around, grabbing the back seam of his shirt and pulled it up towards his head, fully exposing him from the back. In a panic, Tom froze allowing Lisa the time to pull his shirt over his head and down his arms, leaving only his crotch covered with his balled up shirt around his hands and wrists.

Wanting to give the girls a good show, Lisa readjusted her grip on Tom shirt and began pulling side to side causing him to have to follow her lest he be exposed, this also had an unintended concequence of her hands grazing Tom's crotch which was not lost on either of them. After having turned enough so that Tom's back was to the others, Lisa paused and looked over Tom's shoulder, giving Liz and her camera a knowing grin which she then oriented towards Tom which petrified him. Expecting Lisa to continue the tug of war towards the left or the right he braced his shirt against his groin but instead she quickly crouched down and began pulling downwards towards the floor. This had her desired effect of making Tom bend over at the waist and sticking his ass out towards the camera, making the girls behind him shriek with laughter but she wasn't done yet, from here she pulled back hard, causing Tom to stumble foward and to fall onto his knees. From here Lisa was able to spin around to get her legs around Tom's neck and pull his head straight down towards the floor nestled between her thighs, putting him in an exceptionally compromising situation with his head and knees on the ground and his butt staight up in the air. This gave Liz an unobstructed view of Tom's ass with him unable to do anything about it as she got in close for a better shot.

Tom was in hell, however, he had the silver lining that at least his front was still covered because with all the accidental brushes of Lisa's hands on his penis and the fact that his face is only a couple inches from her crotch he was as hard as he has ever been, a fact that, once again hasn't been lost to Lisa who's head was now place directly under Tom's crotch. Not wasting anytime, she began to turn over onto her side, once again forcing Tom to follow her, falling onto his side unless he wanted to lose his head. She kept this up, having them end up in a final position of Tom on his back, hands firmly covering his erection with his shirt and Lisa on top of him straddling his head.

With the intention on finally uncovering what Tom's been desperately trying to keep hidden, Lisa looked over to Liz who was still filming, then to Anne who was watching in amazement with her hands over her mouth and finally she looked over to... Ms. Graham? Stephanie was no where to be found, replaced instead by an angry looking 28 year old gym teacher running over to help poor Tom who was over powered, out numbered and beyond humiliated. Lisa froze in her tracks, staring at the teacher like a deer in headlights which caused her two friends to look over and have similar reactions. Lisa got off Tom as Ms. Graham got closer to them.

"You three girls, to the library, now. Grab your stuff and call your parents to pick you up. If I see you roaming around the school there will be hell to pay" She shouted. She handed Tom's pants to him "Go get dressed and wait for me in my office, you can tell me what happened after I get back from escorting them to their belongings" she slammed the door behind them and like that, the gym was empty. Tom looked at the clothes in his hands and noticed that his underwear were missing so he began frantically looking around the gym for them while staying covered as best he could. After a few minutes, he concluded that Stephanie must've took them with her before once again eluding punishment, he let out a sigh and walked over towards the gym teacher's door and once inside set down his shirt and pants on the desk to catch his breath. He grabbed his pants and began pulled them on one leg but as he did so the office door swung open and Ms. Graham walked in.

"Ok well now that they've been dealt with..." she trailed off, locking eyes with Tom, then quickly looking over his naked body pausing for a moment on his erection that he had'nt had a chance to cover yet, then going back to making eye contact with him. "Oh...sorry, open the door when you're ready." she said as her eyes lingered a second longer than they should have and she swung the door shut. Tom hurriedly finished dressing as his mind swirled with dread, someone, a woman, just saw him naked, fully naked, and hard too! He was pretty sure he saw a smirk on her face too as she closed the door but he quickly push that thought to the back of his mind as he opened the door anew and let her back in then took a seat.

"Hey so, you want to talk about what happened? I got of got the gist of it from the three girls." Ms Graham asked as she sat down across from Tom.

"I'd rather not, I think I just want to go to sleep for the night, if that's ok with you."

"Yeah that's fine, but just so you know, I'm still looking for one of the boys from earlier, I sent the other two home. I'll come check on check on you in a bit."

"Ok" Tom replied and he got up.

As he headed for for the door he noticed that Ms Graham was staring absent mindedly at his crotch as he walked away which made him pick up the pace and close the door behind him.

[Trundle]

Really promising start to the story here, very much enjoying it.

The mean girls seem determined to embarrass poor Tom and I wonder what their next plan is. Interesting that Ms.Graham seemed to enjoy seeing the boy naked and erect, I take it that she liked what she saw?

Great stuff so far.

[TeenFan]

Hmmmm... the boys who harassed Tom have been sent home.
The girls who just harassed Tom are about to be sent home.
Who is left to harass poor Tom?

We still don't know how big Tom is down there. Only the teacher knows. Will the teacher try to see it again?

[tim409]

Hmmmm... the boys who harassed Tom have been sent home.
The girls who just harassed Tom are about to be sent home.
Who is left to harass poor Tom?

We still don't know how big Tom is down there. Only the teacher knows. Will the teacher try to see it again?

Will she find a way to have him show it to ALL the girls in her class or even the whole school. if he is average or a little larger than average we can only hope so

[NickTwisp]

I like how Tom isn't getting blamed for everything. Yes, Ms. Graham enjoyed seeing his penis.