By Pixote
Copyright 2025 by Pixote all rights reserved
[4,687 words]
* * * * *SDO Case Files: Humiliating Punishments
Chapter 3: The Masturbator
Dr. Morgan, the school’s disciplinary officer, wasn’t at all surprised.
It had taken a week after the school reopened for the principal to send
him the first student to discipline.
Minor issues were
addressed as usual. Detentions, extra homework assignments, and
parent-teacher conferences. It typically took a week before an SDO
would need to be called upon for assistance.
The honeymoon period was over.
Dr. Morgan had sent two prefects, Bart and Max, both year 12 students,
to the principal’s office to bring fifteen-year-old Troy Davidson to
him for punishment. Troy was caught by his history teacher masturbating
while she was in the middle of an oral presentation.
Troy was
sitting in the back row of the classroom. He thought there was no way
Ms. Fields would be able to see what he was doing under the cover of
his desktop.
Unfortunately for him, Ms. Fields noticed a
student named Heather Meadows kept turning toward Troy to watch his
erotic performance. This led to her discovery of Troy stroking his
penis that he had pulled out of his jeans through his open zipper.
Troy is one of her favorite students. He was always courteous and
well-behaved, and he maintained a 4.0 GPA in her class. Ms. Fields had
always thought the handsome young boy to be incredibly shy. It was
quite a shock and embarrassing for her to see him exposing himself to
Heather.
It was far more humiliating for Troy when, hearing
Ms. Fields admonish him by demanding he “stop playing with his penis,”
his classmates began laughing at him. He wasn’t sure how many saw his
boner when, unable to prevent the inevitable, he fired off streams of
cum that splashed against the bottom of his writing desk.
Ms. Fields tried to de-escalate the situation.
However, when he refused to explain to her or the principal why he was
displaying himself in such a lewd manner, with a female classmate
watching him, they felt Troy had to be sent to the SDO for punishment.
As it turned out, while waiting for his prefects to arrive with Troy,
Ms. Fields came to Dr. Morgan with additional information that would be
a key element in his interrogation of the young boy.
……..
Troy was standing with his shoes on the footprints that were on the
floor, six feet in front of the SDO’s desk. This forced him to stand
with his feet shoulder-width apart. His hands were behind his head with
his fingers interlocked.
“Troy, since this is your first time
visiting my office, there are important rules you need to be aware of.
If you fail to comply with these rules, your punishment will be far
more severe. Do you understand?”
Troy nodded.
“When
asked a yes or no question, you’ll always answer verbally. There are
only two acceptable responses. Yes, sir. No, sir. Do you understand?”
“Yes, sir.”
“When I ask you a question, you’ll answer truthfully without
hesitation. If I instruct you to do something, you’ll do so
immediately. Do you understand?”
“Yes, sir.”
“Every
student who is referred to me for discipline must remove all of their
clothes immediately when I request them to do so. They’ll then stand
exactly as you are now before I begin questioning them. Troy, do you
understand?”
Troy began to feel his penis stiffen. Why was he
getting a boner? He was scared. Shouldn’t it shrink? He began to blush.
His lips began to quiver. His eyes became teary.
“Troy, I asked you a question. Do you understand?”
In a very weak, unsteady voice, he replied, “Yes, sir.”
Then he felt his knees weaken when the SDO continued.
“Troy, please remove your shoes and socks, then your shirt, followed by
your jeans and underwear. Fold your clothes as you take them off and
hand them to one of the prefects. Then return to standing with your
bare feet on the footprints and your hands behind your head.”
Dr. Morgan watched Troy freeze, unable to begin undressing.
The doctor was impressed by his school records. He could sense that
Troy was a great kid who made a foolish mistake, one that was so out of
character for him that it’d never be repeated. The SDO chose to soften
his approach.
“Troy, do you have Mr. Wallace for study hall?”
“No, sir. I have my study hall period in the library with Mrs. Bell.”
“Max. Please show Troy the unique features of Mr. Wallace’s study hall.”
Max led Troy to a door beside the large curtain that covered the wall
opposite Dr. Morgan’s desk. The curtain Troy had been standing in front
of. When Troy entered the study hall, he saw Mr. Wallace at his desk in
the front of the classroom, with doors leading into the hall on both
sides of the front wall.
Mr. Wallace looked up to see Troy
being escorted by the prefect. Troy was concerned when he noticed the
teacher grinning, giving Max a thumbs-up. Troy didn’t see Max returning
the gesture.
In front of Mr. Wallace were students, sitting
at desks, facing towards him, away from the teacher. There were six
rows of five desks, totaling thirty students. This study hall session
included students from years 7 and 8. When the seated students looked
up, they’d see a large picture window on the classroom’s back wall.
Max pointed out the window to Troy, explaining that the curtain they
could see through the window was the one he had been standing in front
of in the SDO’s office. This side of the curtain featured, at its
center, large, life-size caricatures of two blushing teenagers—a boy
and a girl. Both were naked and standing facing each other. The girl
was measuring the boy’s erection with a ruler.
Max noticed how
frightened Troy was. Giving him a friendly elbow, he grinned and then
whispered, “Good thing the doctor doesn’t have girl prefects.”
Troy could only nod in agreement.
“Be sure to do everything you’re asked to do. Answer all of Dr.
Morgan’s questions quickly and honestly. If you don’t, he’ll open the
curtain and everyone sitting in this study hall will see you being
punished.”
Troy blushed, hoping none of the students watching
him as he was led back into the SDO’s office would notice his boner
pushing out the front of his jeans.
Max had Troy resume the position required by the SDO during punishment sessions.
“Troy, when a boy who is sent to me fails to undress immediately, I’d
usually open the curtains and direct him to undress facing the students
in Mr. Wallace’s study hall. If the boy still refuses to obey me, my
prefects would strip him in front of the window.”
Dr. Morgan saw Troy with his head down, beginning to break down and cry.
“Would you like a second chance to undress with the curtain closed?”
Troy quickly looked up to see if the SDO was serious.
“Yes or no?”
Troy nodded, failing to issue the verbal response.
Troy slowly took his clothes off. He was meticulous in folding his
shirt and pants neatly before handing them to Bart and Max. It didn’t
surprise the SDO or prefects when he froze again while standing,
wearing only a pair of white Y-Fronts.
His body language told
the SDO that, as Ms. Fields claimed, Troy was extremely shy. He was
curious as to why Troy would expose himself in a classroom.
“This is really embarrassing for you.”
“Yes, sir.”
“Would you like Bart and Max to help you finish?”
Troy looked at Bart and Max. Both boys were smiling at him. Max winked.
They had been really nice to him since they first met in the
principal’s office. He wished they could be friends, but he thought
seniors wouldn’t want to hang out with a freshman.
“Yes, please.”
Turning to the prefects, the SDO noticed both boys were sexually
aroused as they were checking out the bulge in Troy’s briefs. During
their prefect interview together, they had admitted to Dr. Morgan that
they were gay and had been best mates since entering high school.
Their interview was one that the SDO would never forget. All of his
prefect applicants, except Max and Bart, showed varying degrees of
modesty when told they had to be naked during their interview. He had
no doubt that Max and Bart would attend all of their classes naked if
given the chance.
“Max. Bart.” The prefects, at first, were
looking a bit guilty, having been caught staring at Troy’s crotch. They
then broke out in smiles when they saw the SDO wink at them. “Be
gentle.”
The two senior prefects knelt down, Bart behind Troy, Max in front.
“Troy, just relax. Bart and I will try to make this easier for you.”
“But you’re going to see my boner.”
“Fact of life. Boys get boners. See?”
Troy grinned when he looked down to see both Bart and Max grabbing
their cocks. They were covered by their clothes, but he knew for sure
both prefects had boners just like him.”
Bart ran the palm of
his hand gently over Troy’s back, allowing it to move down to his
bottom covered by the soft cotton briefs. He then caught Troy by
surprise by inching his way inside his briefs to rub his bare butt
cheeks.
While Bart was teasing Troy’s bottom, Max was running
his hand over Troy’s chest. He felt Troy gasp for air when, after
playing with his nipples and innie, he slipped his hand inside Troy’s
briefs to cop a feel of his cock and balls.
If you asked Troy,
he’d do a pinky swear that the prefects teased him for several minutes.
In reality, the prefects spent less than thirty seconds prepping him
before Max broke the silence.
“Ready?”
Out of options, Troy nodded, while feeling unsteady and light-headed.
Bart sat back to watch Max lower Troy’s briefs.
Then, time froze once again.
As Troy stood rigid with his eyes squeezed shut, Dr. Morgan and his
prefects finally had a chance to admire the naked boy standing before
them.
Troy was a handsome fourteen-year-old. Yet, looking at
him, one would consider him to be average. He was of average height.
Average weight. His brown hair was cut short to conform to the school’s
appearance codes. So, unless you saw him naked, he was simply …
average.
However, when you saw Troy naked, you’d never describe him as an average boy.
Troy had just started puberty. The doctor suspected his maturation had begun nine to twelve months before this session.
There was a small amount of short brown hair beginning to grow in
Troy’s armpits and above his cock. Other than that, there was only
peach fuzz here and there. Troy’s upper lip, his forearms, and his
shins. Troy’s testicles hung in a loose scrotum. The hairless sack held
balls that were certainly no longer prepubescent.
Troy had an
impressive penis for a boy his age. Without measuring, the doctor would
guess his erection was between four and a half to five inches long and
had begun to thicken. His foreskin was on the short side, as in his
erect state, it only managed to cover the corona of his glans. This
allowed them to see the small drop of precum that had formed on the tip
of his cock.
Bart was the only one of the three who currently
had a view of Troy’s bottom. Smooth. Firm. Showing dimples when Troy
flexed his body. Now that Bart could see the lovely buttocks he had
fondled just a minute ago, he was struggling to keep from reaching out
again.
“Troy.”
Dr. Morgan watched as Troy was standing with his briefs just below his knees. Failing to respond, he spoke again.
“Troy. I need you to step out of your briefs. Because you’re positioned
with your feet spread apart, Bart and Max can’t take them off unless
you help them.”
Troy opened his eyes and looked down to see
Bart and Max still kneeling, both now in front of him. He laughed when
the prefects opened their eyes wide while staring at his erection. They
were sticking out their tongues to tease him, acting as if they wanted
to lick his cock.
Truth be known, Bart and Max were acting, but if allowed, would have enjoyed tasting Troy’s cock.
After stepping out of his Y-Fronts, Troy resumed standing as the SDO
had initially positioned him. The difference being he was now naked
with his cock screaming for release as it pointed upward toward the
ceiling, and a bead of precum was beginning to make its way down the
underbelly of his cock shaft.
With the prefects now standing beside Dr. Morgan, the punishment session continued.
“Troy, it is obvious to me that Ms. Fields’ intuition is correct. That
you’re extremely body-shy. So I have to ask. What the hell were you
thinking? Why were you jerking off in her class? Why would you allow
Heather Morrison to watch you masturbate? Is Heather your girlfriend?”
“NO! NO! Heather isn’t my girlfriend!”
“Then why were you allowing her to see you stroke your cock?”
Troy stood silent, hoping the SDO would continue without repeating the question.
“Troy. You know you’d better not lie to me.”
“Yes, sir. But I’m telling you the truth. I don’t have a girlfriend.
Heather sits two rows in front of me. She was supposed to be facing
forward. I sit in the back row of the classroom. I didn’t think any
student would risk upsetting Ms. Fields by turning their back to her
while she was talking to us.”
Troy knew Heather was watching, but hoped the SDO wouldn’t find out.
“What about the students sitting beside you?”
Troy shrugged again, not wanting to answer.
“If she were sitting beside you when you jerked off, would she have been able to watch you without Ms. Fields noticing her?”
Troy struggled to do so but answered. “I guess so.”
It was time for the SDO to set the trap. He whispered instructions to
Bart, who then immediately left the SDO’s office. Max took the
opportunity to take some tissue and wipe the precum from Troy’s cock,
causing him to rise to his toes, trying to prevent himself from cumming.
“Sorry, sir.” Max blushed when he noticed the SDO was waiting for him
to finish. “He was dripping. I didn’t want him to make a mess on your
floor.”
A grinning Dr. Morgan gave Max a reassuring nod,
causing the prefect to realize the SDO wasn’t upset at his feeble
excuse to grope Troy’s cock. Max mouthed the words” Thank You” before
returning to stand next to the SDO.
“Troy, do you know Scotty Connors?”
The SDO had to ask him again before he admitted he knew Scotty.
“Scotty was in Mr. Johns’ Algebra classroom when he found out that you
were caught masturbating in class and were being sent to me to be
punished. He was so upset that he got himself into trouble when
demanding to speak to Ms. Fields. Would you like to tell me why he was
so upset that he managed to be given a week of detentions?”
Before Troy could answer, Bart had returned from the administrative
offices, escorting Scotty into the room. The SDO was surprised when he
noticed Scotty, a fourteen-year-old ninth grader, appeared several
years younger.
Scotty was upset when he saw his friend being punished. He began to run over to him, but Bart was quick enough to restrain him.
“I should be the one who’s punished. Not Troy. He was only trying to protect me!”
Max took a chance that the SDO would not object if he made a suggestion.
“If you really feel that you should be the one to be punished, maybe you should prove it by taking off your clothes.”
Everyone immediately looked at Max, who shrugged while displaying a
mischievous grin. When the SDO looked back at Scotty to see what his
response would be, he was surprised to see clothes scattered all about
the floor. Scotty was now wearing only a pair of pink bikini panties
with lace trim.
Blushing, Scotty was covering himself the
best he could while explaining, “I didn’t have any clean boxers to put
on when I got dressed this morning and had to borrow my sister’s
underwear.”
Troy grinned at his friend, mouthing silently “Sexy!”
The SDO decided he might as well go along with his prefect’s scheme to see Scotty naked.
“Well, are you going to finish so we can continue?”
Scotty’s blush intensified as he struggled to respond to the SDO.
When he hesitated, Bart teased him as he patted Scotty’s bottom, “You
might as well drop them so you can stand beside your buddy. Or would
you prefer to watch him being punished while wearing your girly
panties?”
When Scotty finally gave in, stepping out of his
panties, Bart took the opportunity to cup his hand over one of his
unblemished butt cheeks to cop a feel before giving them a soft spank,
encouraging him to join his friend.
The doctor and two
prefects watched as the two boys hugged, hands moving over each other’s
bodies, making it obvious to everyone they were far more than just
school buddies.
It was actually Troy who told Scotty how to stand, just as he himself had been instructed by the SDO.
Scotty was every bit as cute as his friend, the main difference being
that he was in the very early stages of puberty. His
three-and-a-half-inch circumcised erection had begun to thicken. His
small testicles had dropped into a loose scrotum. Half a dozen wispy
hairs above his cock. Peach fuzz in all the expected places.
“Okay, Scotty. You tell me it’s you who should be punished. That Troy
was trying to protect you. I need to know how jerking off in a
classroom was protecting you. You have two minutes to tell me the
truth, or you’ll both be in serious trouble.”
Scotty quickly
responded, “This morning, after our homeroom teacher took attendance
and dismissed us, Butch Davis and his friend Jose Santiago cornered me
and Troy as we stopped to use the restroom. Butch told Troy that unless
he did exactly as he was told, he’d hold me down after he finished with
me while Jose tapped my ass.”
“I tried to convince Troy to
ignore them. Troy was worried about what would happen to me if he
refused to follow Butch’s instructions. I shouldn’t have told him about
what happened yesterday.”
“What happened yesterday?”
Scotty didn’t want to answer. Instead, he repeated, “I swear, I tried
to tell Troy to ignore Butch. I just knew he’d get caught.”
The SDO was furious. “Let me guess. Troy was told he had to masturbate
in Ms. Fields’ history class and that if he refused, he and his cronies
would gang up on Scotty.”
Both boys responded, “Yes, sir.”
“Dr. Morgan. Max and I have a history with Butch from our junior year,
when we served as hall monitors. He’s a freshman, but already has a rep
as a bully who targets any boy he feels he can physically intimidate.”
Bart added, “Jose seems to me to be a good kid. I’m surprised he’s hanging out with Butch.”
Troy nodded, “Jose seemed upset. He began to question Butch, asking him
why he was doing this, before he was told to shut the fuck up.”
Dr. Morgan decided to finish up so he could address the real issue. Butch Davis and his accomplice, Jose Santiago.
“Scotty, you’re obviously not going to be punished. I appreciate that
you wanted to help your friend. I’ll get the incident removed from your
records. You won’t need to serve the detentions. You can go ahead and
get dressed.”
“Troy doesn’t deserve to be punished for trying to protect me. Let him go, and I’ll take his place.”
“Scotty, if you want to stay in support of Troy, then you’ll be given the same punishment as Troy. Is that what you want?”
“Yes, sir.”
“Okay, as you wish.”
Turning to Troy, “You know I need to punish you for masturbating in Ms.
Fields’ classroom. If I don’t and the other students find out, God
knows how many more boys will try to get away with jerking off during
classes when they get bored.”
“You’re a victim of being
bullied. But that doesn’t excuse you for what you did. This could’ve
been avoided if you had come to me or one of the other teachers and
reported Butch’s threats.”
Turning toward his two playful
prefects, he was curious what they were thinking. “Any suggestions on
what his punishment should be?”
The SDO huddled with Max and
Bart while Troy and Scotty, both now with flaccid penises, waited to
find out what their decision would be. Dr. Morgan felt bad for Troy. He
told the prefects he had to punish Troy, but at the same time, he
wanted to go easy on him. Well, easy when compared to what he would
typically do to humiliate him.
With the prefects huddled with
Dr. Morgan as he accessed school schedules on his laptop, a plan was
formulated. Max and Bart left the SDO’s office.
“Troy, I
believe in the principle of proportional justice. An eye for an eye. In
this case, you’re being punished for masturbating in class, taking the
chance of being seen by students and your teacher.”
Dr. Morgan
circled behind the two boys before warning them, “Be sure to keep
looking forward. Don’t turn to look behind you. Do you understand?”
Both boys replied, “Yes, sir.”
“I’m going to open the curtain. If you keep looking forward, with your
hands behind your head, the students in Mr. Wallace’s study hall will
only be able to see your backside.”
Troy and Scotty heard the
curtain being pulled open. Then they listened to the cheers and
laughter of thirty boys and girls in the study hall who were now
looking at their bare bottoms.
Dr. Morgan returned to stand
before Troy and Scotty. Just as he had suspected, the penis of both
boys were rising to the occasion.
“As long as you do exactly as you’re told, I will not make you turn around to allow the students to see you jerk off.”
.… For the next few minutes, the blushing boys stood still, not daring to move ….
Troy
wanted to look behind him to see the students who were looking at his
naked butt. Were they the same students who were there when Max took
him into Mr. Wallace’s study hall? Could they see his balls hanging
between his legs because of the way he was standing?
Scotty
was confused and nervous. He had no idea about the window behind the
curtain and the adjacent room. He wanted to ask questions, but didn’t
dare to upset the SDO.
…. Then, just when they thought things couldn’t be more humiliating ….
Max
and Bart knocked on the SDO’s door but didn’t wait for a response.
Instead, they rushed into the office. Troy and Scotty noticed the
prefects were grinning at the SDO as they whispered to him.
Troy and Scotty panicked when they saw Ms. Fields standing at the open office door.
“I’m sorry it took so long to join you.” Ms. Fields smiled when she
noticed the two blushing boys struggling to keep their hands behind
their heads. “It took me a few minutes to decide which students I
should bring with me.”
Ms. Fields entered the office, stepping
to the side so that three year 9 girls could enter the room. The girls
ran over to stand in front of their classmates. Excited and clapping
their hands, they could hardly resist the temptation to touch the boys.
Dr. Mason had to warn the boys of the consequences of trying to cover
up with their hands. The boys had no choice but to obey, as they
certainly didn’t want to turn to face the open window to be seen by the
thirty students in the study hall.
Ms. Fields told Alice, Robin, and Violet to sit on the floor in front of Troy and Scotty.
After a quick explanation to the three young girls about why the boys
were being punished, the SDO, flanked by Ms. Fields and the two
prefects, stood before Troy and Scotty.
“Troy. Scotty.
Remember. You were warned before I opened the curtain. I warned you
again when Ms. Fields and the girls arrived. I will not warn you a
third time. Do you know what will happen if you fail to do exactly as I
say?”
They both answered, “Yes, sir.”
“Boys, I want
both of you to masturbate while all of us watch you. You’re to let us
know when you feel you’re about to finish by screaming as loud as you
can, I’M CUMMING! Do you understand?”
Scotty was, if at all possible, even more humiliated when he confessed, “But sir, when I jerk off, nothing comes out.”
“But does your body feel really good when you finish masturbating?”
“Yes, sir. It feels like my body is exploding.”
“That’s fine. You can still announce when you’re having those great
feelings by shouting out for all of us to know you‘re having a dry cum.”
Scotty nodded, trying to ignore his girl classmates’ teasing. Troy was
upset that the girls were making fun of his friend, but he knew he
couldn’t say or do anything. Yet.
“Ms. Fields has a class to
teach in twenty minutes. If you’re not finished by the time she has to
leave, I’ll have you follow her to her classroom and finish in front of
her students.”
Troy and Scotty looked at each other, both
wondering if the SDO would really make them walk down the hall naked
and then jerk off in front of Ms. Fields’ next class.
Leaving one hand behind their head, they used the other to begin stroking their cocks.
The students in the study hall watching through the window could only
see the boys’ naked bottoms, but knew they were jerking off in front of
the girls who sat in front of them. The movements of their arms were a
sure giveaway.
Then, as time progressed, Troy and Scotty
began thrusting their hips as they stroked their cocks. This added to
the excitement building up in Mr. Wallace’s classroom.
Troy and Scotty could hear the students cheering them on.
It wasn’t long before the SDO warned them. “Boys, you only have ten
minutes left before Ms. Fields needs to leave. Take your other hand
from behind your head and play with your chest or balls while you jerk
off to help you finish up.”
With only five minutes left before
Ms. Fields’ departure, Scotty could feel his body begin to tingle. He
started stroking his cock faster, then screamed loud enough for
everyone to hear:
“I’M CUMMING!”
Everyone
noticed there were a few drops of watery discharge from Scotty’s cock,
indicating he was close to having wet orgasms. When Troy saw this, he
was so excited for his friend that it caused him to reach his orgasm.
“I’M CUMMING!”
Remembering
how the girls had been cruel to Scotty because he told the SDO he
didn’t produce cum when he jerked off, Troy got a little revenge. The
girls actually made it easy for him as they had edged closer to Troy to
get a close look at his cock when he shouted he was going to cum.
Troy shot half a dozen streams of cum into the air, making sure to hit
each of the three girls at least once in their face or hair with his
cum shots.
The students in the study hall, now pressed up
close to the window to get a better view, began cheering and laughing
when they saw Troy aim his cum at the girls.
……..
To Be Continued in:
SDO Case Files: Humiliating Punishments
Chapter 4: The Bully