Date: Mon, 15 Jan 2024 11:28:21 -0500
From: Storm Cleaver <thestormcleaver@gmail.com>
Subject: Jock Fitting

The noise of adolescent boys chatting and laughing reverberated off the
walls of the locker room, each one patiently waiting their turn. Paul
Grider, the newest teacher responsible for Physical Education and Sports
Medicine at the school, had set up an improvised assessment area in the
communal showers. While the real coaches took care of helmets and pads,
Paul was in charge of properly fitting the boys with their proper
protective equipment. That meant thirty four incoming freshmen would need
to be fitted with their own personal cups and jocks before the final bell
rang.

In a show of solidarity, Mr. Grider discreetly wore his own jock to
school that day, if only for the purpose of keeping his manhood
contained. He had been an athlete throughout his life, starting with club
soccer before transitioning to football in high school. After college, he
continued to stay fit through running and strength training, resulting in
a toned physique that he could be proud of. After three hours of watching
young men strip and play around with their crotches however, Paul's own
jock was being pushed to its limit. His manhood was thickened and
strained against the black fabric of his athletic shorts. To avoid any
embarrassing situations, the teacher was forced to remain seated for a
majority of the time. He couldn't help but laugh at himself, a
twenty-seven-year-old man stuck in the same awkward spot he had been
twelve years ago, trying desperately to hide his erections in the boy's
locker room.

Daniel, a large boy who would almost certainly be a starting offensive
lineman, finished pulling his shirt over his head and grabbed his new
jock and cup before leaving.

"Go ahead and send the next one in," Seth told him as the young man
exited the showers and rounded the corner. His voice echoed off the
cement tile walls. Paul took advantage of the small break and reached
down to adjust himself, pulling his erection up and to the side so as to
remain inconspicuous. It throbbed in his hand, a dull ache forming that
would require attention sooner than later.

His ears perked up at the scuff of shuffled footsteps growing louder and
he looked up to see a young man round the corner.

He was shorter than most, standing eye to eye with Mr. Grider, who sat in
an aluminum folding chair.

The boy seemed to be in good health, and he had the potential to develop
a strong and attractive physique. With his handsome features and dirty
blonde curls, he would only become more appealing as he grew older,
making him desirable to both men and women. Paul had seen him in the
halls before but could not quite recall his name.

"Hey Mr. Grider," the boy said nervously, catching the teacher's eye
before quickly turning his gaze to the tile floor.

Paul met him with a smile. "Hey bud, nice to meet ya. What's your name,"
he asked.

"Seth Witfield, sir."

His groin ached at being called sir.

"Well Seth, you know why you're here right?"

The man kept his eyes fixed to the ground as he muttered, "Yes sir. The
other guys said we're getting a cup and a jockstrap."

"That's right," Paul replied. "My job is to make sure everything fits
properly so you can play without getting injured. Are you ready?"

Seth's nod was almost imperceptible.

"Excellent. Why don't you take off your shorts for me," Paul said,
gesturing towards a folding chair placed against the wall below a shower
head.

His pale cheeks flushed with embarrassment, but he complied with Paul's
request anyway. He made his way to the chair, slipped off his red
sneakers, and tucked them under the seat. Seth deftly slipped his shirt
over his head and, keeping his back to Paul, used his thumbs to pull down
the waistband of his shorts, revealing a pair of tight white briefs that
hugged his plump buttocks. They looked just small enough to fit in Paul's
hands. The fabric stretched as he bent over to remove the shorts
completely, wrapping around Seth's thighs. They were thick, larger than
most boys his age, and nearly covered with a light dusting of blonde hair
that thinned as it rose from feet to waist.

Paul watched intently as the young man slipped his right foot out of the
shorts quickly followed by the left before setting them on the seat. His
breath caught as Seth turned around to reveal the hefty bulge of his
crotch; apparently the boy was developing faster than his peers in more
ways than one. It looked like it still had room to grow, and was
certainly nothing compared to Seth's, but it would certainly serve the
young man well in the coming years.

"Alright come on over here now. I'll have to measure your waist to get
the right size," Paul said, reaching down to retrieve the tape measure
off the ground.

Seth hesitated, then walked to stand at attention in front of his
teacher. Standing a half step away, he now stood slightly taller than his
teacher, bare chest at eye level and he looked down into Paul's eyes. As
he stood before his teacher, he quickly shielded his crotch with his
hands. Was it out of modesty or embarrassment, the man wondered.

Paul stole glances of the boy's body as he wrapped the measuring tape
around Seth's waist. His chest was completely hairless still but starting
to show a little muscle development, most likely due to the summer
training program all Freshmen were required to attend. He was lean, with
his upper abs showing and a small trail of body hair disappearing below
his waistband. Paul's pulse quickened as his gaze travelled further
south, trying to peek behind the boy's hands. His thoughts were clouded
by the throbbing of his own crotch.

"Can you move your hands for me," Paul asked, "I'll need to get a good
measure of your waist." He sensed hesitation from the boy, but waited
patiently until Seth raised his arms just enough to expose his crotch.

Paul couldn't help but stare in awe at the stunning image before him.
Through the sheer fabric of Seth's tight white underwear, the clear
outline of his manhood was unmistakable. The head was protruding through
the briefs, it even seemed to pulse under the fluorescent lighting, while
the rest of its girth was impressive. Even in its softened state, it
seemed to strain towards Paul, begging for release like a caged animal.

Paul's breath shallowed as he brought both ends of the tape together,
conveniently allowing the back of his hands to rest against the boy's
crotch. He took his time, relishing the feeling of the young man's member
pulsing against his skin.

Paul reluctantly let go of the measuring tape, which read twenty nine
inches. He heard a quiet sigh from Seth, who quickly recovered his groin.

Paul turned to a nearby tub filled with neat stacks of protective cups
arranged by size, from extra small to extra large.

"Based on your waist size, you should be able to fit into a small," he
said with a frown. "We can try it out, but I have a feeling you might
need a bigger size." Paul looked pointedly at Seth's groin, causing the
boy to turn red with embarrassment again.

Before Seth could say anything else, Paul stopped him. "It's okay, bud.
Everyone has a different body, there's nothing to be ashamed of here.
It's just you and me, so there's nothing to worry about."

He reached into the bag of pre-folded jock straps and pulled out a small
one then handed it to Seth.

"What if the other guys make fun of me," the boy asked quietly into his
chest.

"Then they're just jealous," Paul told him with a smile, "Trust me, in a
couple of years you are going to be very, very glad you have to go up a
couple of sizes."

Seth giggled at that and Paul could see the tension in his shoulders
relax.

"Here, let me show you how to put it on," Paul said as he held out his
hand. Seth passed the jock back and Paul unfolded it and slipped the cup
inside the waiting pouch, shifting it around until it was seated
appropriately. He held it up before the two of them, cup facing Seth, and
handed the completed piece back. The Freshman slipped his legs through
the appropriate holes and pulled the waistband up and over his briefs
with a snap.

Paul ultimately found himself dissatisfied with the view, wishing he
could see more. His eyes brightened as an idea formed.

"Seth, your underwear seems to be getting in the way. It might be
difficult to get an accurate measurement with them on."

The boy's brow furrowed at first, then his eyes widened as he finally
understood what his teacher was saying.

"Wait, you mean I have to take them off?" he asked softly.

Paul nodded. "Yeah, I think that would be best buddy. We want to make
sure you have a good fit so you don't get hurt."

Seth's pleading gaze bore into Paul's, begging him to take the words
back, to save him the embarrassment.

Paul held his ground and cocked an eyebrow; as the adult and experienced
physician, they both knew it was his teacher's responsibility to make the
call.

Seth relented. He slipped the thick waistband of the jock over his hips
and handed it back to Paul, who snatched it eagerly, and walked back to
the chair holding the rest of his wardrobe.

With his back to Paul, the boy grabbed the waistband of his underwear and
pulled them down, bending over to pick them up from the floor. His
exposed buttocks were soft and smooth, creamy white with no trace of
hair. They were paler than the rest of his body, a tell-tale sign of how
often they remained covered from the summer sun.

Paul's cock throbbed between his legs, it begged to be freed from his
jockstrap. It wanted to stretch the boy's hole and coat his insides with
its seed. Paul wanted, needed, to breed him. The man's face darkened with
lust as he imagined the boy shedding tears as he struggled to take what
Paul so desperately wanted to give him.

Ignorant of his effect on his teacher, Seth turned around. The head of
the boy's cock was round and swollen, a pretty shade of pink that
contrasted against the rest of his skin. The shaft was just as thick as
Paul assumed with a robust vein meandering up its center. It was slightly
darker than the rest of his body, a deeper shade of tan that made it
appear even more pronounced against the boy's alabaster lap.

Paul watched it sway from side to side as Seth stepped back in front of
him. The powerful scent of the boy's body wash hung in the air as it
washed over Paul; underneath it all, a hint of musk and sweat.

Paul begrudgingly handed the jock back to the young man who slipped it on
once again, snapping the waistband against his abdomen. He found it only
slightly easier to focus without the boy's exposed member mere inches
away. With everything in place Seth shifted uncomfortably, doing a
quarter squat to situate his equipment.

"How's that feel," Paul asked, his eyes not leaving the cup.

"It's...alright. I guess."

"It looks a little too small, bud. Is everything fitting in there
comfortably? Remember, you're going to be wearing this for hours at a
time." Seth continued to adjust his hips in an attempt to get comfortable
in the new cup.

Paul reached out, brushing the boy's initial protests aside, and gently
felt around the outside of the pouch. The cup struggled to contain Seth's
manhood, filled so much that it was pushed away from his body. A poor
fit. Paul moved his fingers lower, slipping between Paul's legs until his
hand was resting on the plastic and his fingertips brushed against the
boy's delicate taint. He placed his other hand on Seth's shoulder, trying
to provide support. He felt the young man shudder at the forbidden touch,
but instinctively opened his legs and thrust his hips forward, allowing
the man easier access.

Good boy, Paul thought to himself with satisfaction.

He savored the feeling as his fingers curled around the tip of the cup
and brushed against the softest skin of the boy's sack. The self control
required to pull away was almost impossible for Paul.

"Definitely too small," He said with a quick smile, "let's try the next
size up." He reached back into the plastic tub on the floor and retrieved
a larger cup then continued, "go ahead and take that one off."

Seth did not move.

Paul's head cocked as he asked, "Is everything alright, bud?"

The boy's eyes bore holes into the tile floor, saying nothing. That was
fine for Paul, who had learned to be a patient man. In truth, he even
enjoyed watching the young man squirm a bit.

Eventually Seth broke and stammered, "I can't take it off right now,
I...I just can't."

Confused, Paul asked, "What do you mean you just can't? I just saw you
put it on a second ago."

"No, I know. I mean..." He started to explain, then stopped. He closed
his eyes and took a breath, then blurted, "I'm hard, ok!"

Paul pressed his lips together tightly as he strained to hide his grin.
He let the words hang between the two of them until Seth finally opened
his eyes and met Paul's.

The man patted Seth's shoulder reassuringly and said, "Don't worry about
it, buddy. It happens to everyone, believe me. I've experienced it more
times than I care to admit." He chuckled.

"Really," the Freshman asked, unsure.

"Sure dude," Paul said, then leaned in closer, "to be honest with you,
most of the other guys who came before you had the same problem. It's
totally natural." He allowed the young man a moment to process, then
continued, "How about we get you fitted once it goes back down?"

Seth let out a tentative giggle, less nervous but still uncertain. "That
might take a little while," he said.

Paul chuckled and the boy cracked a lopsided grin.

"If that's the case, then maybe you should just go ahead and take care of
it yourself," Paul suggested, trying for nonchalance.

"What do you mean?" the boy asked, curiosity sparked in his eyes.

"You know, masturbate."

Seth cocked his head to the side and Paul's heart melted.

"You've never jacked off before? When I was your age, I couldn't get
enough of it," Paul chuckled. It was the truth and the man thought back
fondly to the many dry orgasms he'd had at Seth's age.

The boy simply shook his head.

"It feels amazing," he told Seth, "I can show you how if you want."

No words came out of the young man's mouth, but his head bobbed up and
down twice, his complete attention on the teacher.

Paul took his cue and he rose to his feet before the boy, his large frame
looming over him.

As he moved, Paul's growing bulge was conveniently placed at eye level,
making it impossible for Seth to ignore. Despite the jockstrap's attempt
at containing the man's arousal, there was no hiding the obvious bulge
that protruded through the gym shorts and towards Seth.

The boy's eyes widened and Paul watched them linger on his groin. He let
the boy look, to wonder at what might be hiding just below the surface.

Paul hooked the waistband of his shorts and slipped them down in one
fluid motion. They fell to the ground in a puddle of black Polyester,
revealing the thick grey waist and white pouch of the man's jockstrap.

"See bud," Paul asked as he reached out and tapped the boy's cup, "same
as you."

Seth's jaw fell, as if he had been struck dumb by the presence of Paul's
bulging manhood, his eyes drawn to it like a moth to a flame.

Could he see the precum stain, Paul wondered.

"How about we both take them off at the same time," Paul asked. Instead
of waiting for a response this time, he simply tugged on the waistband of
his jock just the same as he did his shorts just a moment ago, exposing a
neatly trimmed patch of hair while allowing the boy to catch up. Seth
followed his teacher's lead.

Paul's jock hit the floor just before Seth's and the boy's eyes widened
as he took in the sight of his teacher's cock finally revealed.

Paul may have been the same length as Seth when he was younger, measuring
just a hand's width at the advent of puberty, but what set the boy apart
was his girth. While it may have appeared average on the body of an adult
man, it looked impossibly thick hanging between the freshman's legs.

As Paul had matured, his own member retained its girth but grew an
additional two inches before reaching a bulbous head the size of a plum.
Grown men had gawked at their first sight of Paul and Seth was no
exception.

The man confidently reached down and grasped his cock, a familiar weight
in his hands. His eyes returned to the boy's and he raised his eyebrows.
He watched Seth mimic, taking more time than Paul in his hesitancy, but
he eventually wrapped his fingers around his erection. The boy's hips
dipped as his knees buckled at the sensation.

Once Seth's gaze returned to him, Paul spit a thick drop of saliva into
his cupped palm and waited, once again cocking an eyebrow and waiting for
the boy to follow suit. Seth recognized the signal and mimicked, though
it was less graceful in execution.

With deliberate movements, Paul spread the thick saliva over his shaft,
demonstrating for the younger man. After a few moments of observation,
Seth followed suit and began working on himself in a similar manner,
alternating between stroking the shaft and rubbing the head as he had
been shown. Within a minute of practice, he had mastered the motions,
just as young men had done since the beginning of time.

"It looks a little dry down there," Paul said, nodding towards Seth's
erection.

The boy laughed nervously and slowed his pace as he replied, "Yeah, I...I
didn't have enough spit I guess."

"Here," Paul said, pulling his hand away from his own cock and spitting
directly into the palm. He stepped forward and closed the gap between
them. His other hand found Seth's shoulder and he held the boy steady.
The crackle of anticipation and the sound of their shared breaths was
nearly drowned out by the cacophony of voices echoing from the locker
room. Seth let out a sharp gasp as he felt the man's fingers close around
his erection and he instinctively thrust into Paul's hand.

The man had to nearly hold Seth upright as he stroked the young cock. The
boy's breaths were sharp as he was expertly worked by a man who knew
plenty about pleasuring other men. Paul moved his other hand from the
boy's shoulder to the small of his back, providing more support and
allowing Seth to thrust himself into Paul's hand, matching his pace. He
watched those bright green eyes roll back in ecstasy.

In no time Paul felt the boy's abdomen tighten, his movements becoming
more erratic; he was close. He craved more though, and he wasn't done
with the boy just yet.

Paul released Seth's cock from his grasp and lowered himself onto his
knees before the boy. He could clearly tell the boy's confusion but
wasted no time in showing him why he had gotten down there. Paul gently
placed his hand at the base of the boy's erection as he kissed the very
tip. Seth's breathing was shallow, curious and expecting. Paul's lips
parted around the pulsing head and he used his tongue to pull it deep
into his mouth, pleasantly surprised at how much his jaw had to stretch
to accommodate the freshman's cock.

It didn't take long for Paul to swallow it in its entirety. The boy
stretched Paul's throat and the man let out a muffled moan as his nose
pressed into the boy's groin. Up to the hilt, the man swallowed to stroke
the boy's length. The smell of the boy's pure essence mixed with the
taste of his cock was euphoric and almost brought Paul to orgasm, though
he had stopped stroking himself.

With a faint, high-pitched gasp from Seth, Paul felt a hand in his hair
then sharp pain as it grasped a handful.

With his cock deep in the man's throat, Seth's balls drew tighter to his
body, almost ascending completely inside. His knees completely buckled
forcing Paul to catch him. He grabbed the boy by his ass cheeks and
pulled him closer, forcing every inch of the adolescent cock down his
throat.

The boy's first orgasm flooded Paul's mouth, who swallowed it hungrily.
There wasn't much so the man savored every drop.

Paul allowed the boy to enjoy his release before pulling back and letting
the erection slip from his mouth. Seth dropped to his knees before the
man, unable to support his weight any longer. He gasped for air in front
of Paul as he knelt on the cold tiles of the shower floor with his
teacher.

Paul rose to his feet and observed the boy's trembling figure, remnant
shudders still coursing through his small body from experiencing his
first orgasm. He allowed the boy a few moments before clearing his
throat. Seth looked up from his kneeling position. The fog that clouded
his vision seemed to fade as he noticed the bulbous head of Paul's cock
dangling before him. His eyes sought Paul's, pleading.

Paul cock an eyebrow and waited.


Thank you for reading. If you would like to hear more of the story,
please let me know.

-Storm Cleaver