Re: School Over-nighter
Posted: Sun Jul 20, 2025 4:31 pm
Chapter 5: Appropriate attire
A couple days had passed after the incident at the over-nighter, Tom had barely left his room, and hadn't spoken to anyone besides his parents, too traumatized by what had happened. That was until he heard his phone ding, he had received a text from an unknown number.
"Hey buddy! How's it going?" the text read.
Tom didn't respond. Two minutes later, his phone went off again
"I wouldn't ignore me if I were you" he received, followed by a picture of him, naked with his boxers over his head and Stepahnie holding his thigh off to the side.
"How did you get my number" Tom replied.
"Being a teacher's pet has it's advantages, I told Ms. Graham I had heard what happened at the over nighter and that I wanted to see if you're ok because we're such good friends that go way back."
Tom stared at his screen as another text came in.
"Anyway, I volunteered to clean the gym during the break for extra credit and I need help. Meet me at the school yard in 30 minutes, or else..." Stephanie texted, followed by another picture of Tom, naked on his back, with his knees pulled up to his chest.
Not seeing what else he could do, Tom got out of bed and started getting dressed, having to wear briefs again after his only pair of boxers had gone "missing", then putting on a pair of basketball shorts and a t-shirt. Tom made the walk over to school, about 15 minutes and saw Stepahnie waiting out there for him wearing a floral summer dress.
"Hey Tom!" she said as he approached.
Once he got close enough she pulled him in for a hug, confusing him, on one hand he hated Stephanie for what she had done to him, but on the other, having her body pressed up against him made his hormones rage.
"I love what you're wearing," Stephanie said sarcastically "But I brought you a more appropriate outfit for cleaning." as she threw some clothes at him.
Tom held up what she wanted him to wear, a pair of short shorts that seem a few sizes too big for him and a tank top that looked to be too small. Knowing who was in charge, Tom agreed.
"Ok, i'll put this on when we get inside" he said as he started walking towards the building.
"Nah, I want you to put it on now" Stephanie replied, smirking at Tom.
"Please, I can't out here, what if someone sees me?" Tom asked desperately.
"Just be quick about it" Stephanie said.
Knowing he was just wasting his breath, Tom nervously looked around then took off his shirt. As he went to put on the tank top Stephanie stopped him.
"Give me your shirt and shorts before you get dressed" she said, renewing Tom's panic.
He then untied his shorts and slid them down and off, shakily handing his clothes to Stephanie.
"Oh I love your little panties! Give me a spin would you" Stephanie said, full of glee.
Tom obliged and quickly spun around then pulled on the shorts Stephanie had provided, much to his chagrin the inseam was about two inches while the leg holes were about twice the size of his thighs, making it almost look like he was wearing a skirt. He then pulled on the top and it stopped about two inches above the waistband for his shorts not allowing him to cover. Tom felt the shorts beginning to sag slightly so he tied the drawstring tightly and with that he turned to look at Stepahnie.
"Looks good, just one thing, you have a panty line which is very embarassing" she said mockingly, "Luckily for you I have a solution she said as she rummaging around in her bag with one hand as she turned Tom to face away from her with the other. Once the sound of russling stopped, Tom felt Stephanie pull the back of the shorts away from his body and slide something cold and metallic between his underwear and his right hip then she pulled it out. He then felt her repeat the same action on the left side. Once she was done she turned him to face her and grabbed the front of his shorts pulling them open. Tom knew better by this point then to fight it. Stephanie then grabbed the fron of his briefs and pulled upwards, Tom braced for a painful wedgie but his undewear offered no resistance. Stephanie had cut both sides of his underwear and then simply pulled them right off of him. With Tom's butchered underwear in her hand, Stepahnie smiled.
"There, no more panty line, give me one more spin."
Once again Tom spun around quickly, making the the side of his shorts flip up slightly, giving Stephanie a side view of his butt from both sides.
"You look great! Let's get to cleaning" Stephanie said as she tossed Tom's underwear into a nearby bin.
Tom could feel the thin fabric of the shorts rubbing against his bare skin which was both a good, and bad feeling as they entered the school.
As they made this way down the hall, they could hear some chitter chatter though the gym doors. Upon entering, Tom and Stephanie saw Ms. Graham as well as eight freshmen tallking amongst themselves.
"Ah there you are" Ms. Graham said "I'll set you two up for cleaning and then I'm going to take the cheer team out for practice. How are you, Tom, you know after last Friday's ...events".
"G-good!, I'm fine thanks!" Tom's voice cracked as he quickly responded, not wanting her to go into any more detail.
"Ok then, come with me" Ms. Graham said as Tom and Stephanie followed her to the other side of the gym towards a ladder. "Bascially, all I need from you two is to wash the windows in here and in the locker rooms, the ones in here are quite high so I took out this ladder, one of you should go up while the other holds the bottom."
While Ms Graham was explaining, Tom couldn't help but feel like he was being watched, he turned to look at the girls and saw them whispering amongst themselves while one of them pointed at Tom. He recognized that girl from the over- nighter, he had to push her out the way to get into the weight room. His face flushed as he turned his attention back to Ms. Graham.
"For the locker rooms, the girl's room is currently undergoing renos so you only need to clean in the boys'. The ladder in there is shorter so no need to worry about holding it in place. Any questions?"
"No miss." Tom and Stephanie both said in unison.
"Perfect, I'm going to talk to the girls a bit them were going outside, you can get started right away if you'd like." Ms. Graham said as she walked back towards the other side of the gym.
Tom and Stepahnie stared at eachoteher for a moment before Stephanie spoke up.
"Alright, get on up there" she said pointing at the ladder
" What? Why me? I don't like heights. Can you go?"
"Oh, so you can peek up my dress while I'm up there? Yeah right" She said as she handed him a bucket and a cloth.
Resigned to his fate, Tom sighed and shakily climbed the ladder while Stepahnie stayed at the bottom. Once at the appropirate height, Tom hooked the bucket on the ladder and began washing the windows. After a few seconds Tom looked down and saw that Stephanie was puttng her phone away and grinning. Confused, Tom looked back ahead and finished up washing the windows he could reach, then climbed down.
They moved the ladder to wash the windows above the door and Tom climbed back up. Once at the top, the ladder settled slgihtly, causing Tom to adjust his standing position into a slight lunge, with one foot on a higher rung to stabilize himslef.
"Sorry about that!" Stephanie yelled out from the bottom as Tom started washing the windows, half believing her apology.
Just then, Ms. Graham finished speaking witht he girls and headed out the door Tom was standing over, the girls were a bit delayed as they gathered their things. As they approached the door in single file, Stephanie gestured to them, silently pointing up towards Tom, who was focused on cleaning the windows. The first girl didn't understand and walked under the ladder and out the door, Stephanie stopped the second girl, the one had Tom recognized from the over-nighter, once she was under the ladder and once again pointed up.
The girl understood what Stephanie was trying to tell her and looked up. She immediately covered her mouth in shock and stared at the sight above her. Due to the large leg holes in the shorts Tom was wearing and his lack of underwear, anyone standing under him could see everything he had to offer, which is why Stephanie was smiling earlier. The lunge position he was in now simply opened up the leg holes event more giving the girls a fully unobstructed view. The girl moved slightly forward leaving room for the next one, who had the same reaction. As a third girl tried to squeeze in under the ladder, she bumped it making Tom look down to see what was happeneing, as he did, he noticed this girls under him.
"A bit breezy today eh?" the girl Tom recognized earlier called out.
Confused, Tom replied "I don't thinnk it's too bad" giving the time for a fourth girl to slip under the ladder.
"OMG he's not wearing underwear!" the girl cried out.
This caused all the blood to drain from Tom's face and him to immediately clamp his knees together and start descensing the ladder.
"Awe no fair, I didn't get to see yet!" the next girl in line cried out as she shook the ladder angrily.
This Caused Tom to lose his footing and fall a few feet onto his back with his knees bent and his groin pointed at the girl who shook the ladder, giving her a great view oh his genitals poking out of left leg hole of his shorts. Ms. Graham called out from the hall for the girls to hurry up and, not wanting the coach to come back and see what they were up to, the girls hurredly left the gym, giggling about what most of them had just seen.
"Alright Tom, almost there, you just gotta get up the ladder a few more times and we can go clean the boys locker room after this." Stephanie said, looking down at Tom's crotch and offering him a hand up.
Upset, Tom didn't take her hand, he got up and climbed the ladder, being sure to keep his legs closed and continued washing the windows this way until they were done.
A couple days had passed after the incident at the over-nighter, Tom had barely left his room, and hadn't spoken to anyone besides his parents, too traumatized by what had happened. That was until he heard his phone ding, he had received a text from an unknown number.
"Hey buddy! How's it going?" the text read.
Tom didn't respond. Two minutes later, his phone went off again
"I wouldn't ignore me if I were you" he received, followed by a picture of him, naked with his boxers over his head and Stepahnie holding his thigh off to the side.
"How did you get my number" Tom replied.
"Being a teacher's pet has it's advantages, I told Ms. Graham I had heard what happened at the over nighter and that I wanted to see if you're ok because we're such good friends that go way back."
Tom stared at his screen as another text came in.
"Anyway, I volunteered to clean the gym during the break for extra credit and I need help. Meet me at the school yard in 30 minutes, or else..." Stephanie texted, followed by another picture of Tom, naked on his back, with his knees pulled up to his chest.
Not seeing what else he could do, Tom got out of bed and started getting dressed, having to wear briefs again after his only pair of boxers had gone "missing", then putting on a pair of basketball shorts and a t-shirt. Tom made the walk over to school, about 15 minutes and saw Stepahnie waiting out there for him wearing a floral summer dress.
"Hey Tom!" she said as he approached.
Once he got close enough she pulled him in for a hug, confusing him, on one hand he hated Stephanie for what she had done to him, but on the other, having her body pressed up against him made his hormones rage.
"I love what you're wearing," Stephanie said sarcastically "But I brought you a more appropriate outfit for cleaning." as she threw some clothes at him.
Tom held up what she wanted him to wear, a pair of short shorts that seem a few sizes too big for him and a tank top that looked to be too small. Knowing who was in charge, Tom agreed.
"Ok, i'll put this on when we get inside" he said as he started walking towards the building.
"Nah, I want you to put it on now" Stephanie replied, smirking at Tom.
"Please, I can't out here, what if someone sees me?" Tom asked desperately.
"Just be quick about it" Stephanie said.
Knowing he was just wasting his breath, Tom nervously looked around then took off his shirt. As he went to put on the tank top Stephanie stopped him.
"Give me your shirt and shorts before you get dressed" she said, renewing Tom's panic.
He then untied his shorts and slid them down and off, shakily handing his clothes to Stephanie.
"Oh I love your little panties! Give me a spin would you" Stephanie said, full of glee.
Tom obliged and quickly spun around then pulled on the shorts Stephanie had provided, much to his chagrin the inseam was about two inches while the leg holes were about twice the size of his thighs, making it almost look like he was wearing a skirt. He then pulled on the top and it stopped about two inches above the waistband for his shorts not allowing him to cover. Tom felt the shorts beginning to sag slightly so he tied the drawstring tightly and with that he turned to look at Stepahnie.
"Looks good, just one thing, you have a panty line which is very embarassing" she said mockingly, "Luckily for you I have a solution she said as she rummaging around in her bag with one hand as she turned Tom to face away from her with the other. Once the sound of russling stopped, Tom felt Stephanie pull the back of the shorts away from his body and slide something cold and metallic between his underwear and his right hip then she pulled it out. He then felt her repeat the same action on the left side. Once she was done she turned him to face her and grabbed the front of his shorts pulling them open. Tom knew better by this point then to fight it. Stephanie then grabbed the fron of his briefs and pulled upwards, Tom braced for a painful wedgie but his undewear offered no resistance. Stephanie had cut both sides of his underwear and then simply pulled them right off of him. With Tom's butchered underwear in her hand, Stepahnie smiled.
"There, no more panty line, give me one more spin."
Once again Tom spun around quickly, making the the side of his shorts flip up slightly, giving Stephanie a side view of his butt from both sides.
"You look great! Let's get to cleaning" Stephanie said as she tossed Tom's underwear into a nearby bin.
Tom could feel the thin fabric of the shorts rubbing against his bare skin which was both a good, and bad feeling as they entered the school.
As they made this way down the hall, they could hear some chitter chatter though the gym doors. Upon entering, Tom and Stephanie saw Ms. Graham as well as eight freshmen tallking amongst themselves.
"Ah there you are" Ms. Graham said "I'll set you two up for cleaning and then I'm going to take the cheer team out for practice. How are you, Tom, you know after last Friday's ...events".
"G-good!, I'm fine thanks!" Tom's voice cracked as he quickly responded, not wanting her to go into any more detail.
"Ok then, come with me" Ms. Graham said as Tom and Stephanie followed her to the other side of the gym towards a ladder. "Bascially, all I need from you two is to wash the windows in here and in the locker rooms, the ones in here are quite high so I took out this ladder, one of you should go up while the other holds the bottom."
While Ms Graham was explaining, Tom couldn't help but feel like he was being watched, he turned to look at the girls and saw them whispering amongst themselves while one of them pointed at Tom. He recognized that girl from the over- nighter, he had to push her out the way to get into the weight room. His face flushed as he turned his attention back to Ms. Graham.
"For the locker rooms, the girl's room is currently undergoing renos so you only need to clean in the boys'. The ladder in there is shorter so no need to worry about holding it in place. Any questions?"
"No miss." Tom and Stephanie both said in unison.
"Perfect, I'm going to talk to the girls a bit them were going outside, you can get started right away if you'd like." Ms. Graham said as she walked back towards the other side of the gym.
Tom and Stepahnie stared at eachoteher for a moment before Stephanie spoke up.
"Alright, get on up there" she said pointing at the ladder
" What? Why me? I don't like heights. Can you go?"
"Oh, so you can peek up my dress while I'm up there? Yeah right" She said as she handed him a bucket and a cloth.
Resigned to his fate, Tom sighed and shakily climbed the ladder while Stepahnie stayed at the bottom. Once at the appropirate height, Tom hooked the bucket on the ladder and began washing the windows. After a few seconds Tom looked down and saw that Stephanie was puttng her phone away and grinning. Confused, Tom looked back ahead and finished up washing the windows he could reach, then climbed down.
They moved the ladder to wash the windows above the door and Tom climbed back up. Once at the top, the ladder settled slgihtly, causing Tom to adjust his standing position into a slight lunge, with one foot on a higher rung to stabilize himslef.
"Sorry about that!" Stephanie yelled out from the bottom as Tom started washing the windows, half believing her apology.
Just then, Ms. Graham finished speaking witht he girls and headed out the door Tom was standing over, the girls were a bit delayed as they gathered their things. As they approached the door in single file, Stephanie gestured to them, silently pointing up towards Tom, who was focused on cleaning the windows. The first girl didn't understand and walked under the ladder and out the door, Stephanie stopped the second girl, the one had Tom recognized from the over-nighter, once she was under the ladder and once again pointed up.
The girl understood what Stephanie was trying to tell her and looked up. She immediately covered her mouth in shock and stared at the sight above her. Due to the large leg holes in the shorts Tom was wearing and his lack of underwear, anyone standing under him could see everything he had to offer, which is why Stephanie was smiling earlier. The lunge position he was in now simply opened up the leg holes event more giving the girls a fully unobstructed view. The girl moved slightly forward leaving room for the next one, who had the same reaction. As a third girl tried to squeeze in under the ladder, she bumped it making Tom look down to see what was happeneing, as he did, he noticed this girls under him.
"A bit breezy today eh?" the girl Tom recognized earlier called out.
Confused, Tom replied "I don't thinnk it's too bad" giving the time for a fourth girl to slip under the ladder.
"OMG he's not wearing underwear!" the girl cried out.
This caused all the blood to drain from Tom's face and him to immediately clamp his knees together and start descensing the ladder.
"Awe no fair, I didn't get to see yet!" the next girl in line cried out as she shook the ladder angrily.
This Caused Tom to lose his footing and fall a few feet onto his back with his knees bent and his groin pointed at the girl who shook the ladder, giving her a great view oh his genitals poking out of left leg hole of his shorts. Ms. Graham called out from the hall for the girls to hurry up and, not wanting the coach to come back and see what they were up to, the girls hurredly left the gym, giggling about what most of them had just seen.
"Alright Tom, almost there, you just gotta get up the ladder a few more times and we can go clean the boys locker room after this." Stephanie said, looking down at Tom's crotch and offering him a hand up.
Upset, Tom didn't take her hand, he got up and climbed the ladder, being sure to keep his legs closed and continued washing the windows this way until they were done.