Date: Wed, 19 May 2021 14:58:38 +0100
From: Ant XXX <ant90xxx@gmail.com>
Subject: Deputy Headteacher - Chapter 1 (Gay > Adult-Youth)

Pete Roughley was the deputy headteacher of a large secondary school in
the north of England. He had been teaching for nearly fifteen years
before being promoted to deputy headteacher last year, and was widely
respected around the school for his strict, no-nonsense approach to
dealing with teenagers.

As he was getting dressed for school one morning in early October, Pete
stopped and admired himself in the mirror. His subject area was PE and so
his body was firm, though the light coverage of dark hair over his body
softened the view. He ran his fingers through his short brown hair and
looked over at his wife asleep on the bed, their two young children
sprawled across her. He loved his wife very much but since their second
child came along their sex life was a thing of the past.

Pete's hand strayed down to his cock and he began to absent-mindedly
play with it, the five inches when flaccid quickly growing to a thick
seven-inch erection nestled among a thick bush of pubic hair. He wondered
if he had time for a quick wank in the bathroom and checked his watch.
No, he was already running late so quickly pulled his clothes on, gently
kissed his wife and children and made his way out to the car.

*

At 38, Pete was by no means the youngest member of staff, but he was
certainly the one most of his colleagues (and a lot of pupils) had a big
crush on. He still taught a few lessons on PE here and there so rather
than a suit and tie, he usually wore a white T-shirt and a pair of black
shorts that reached about halfway down his thigh.

As he walked down the corridor towards his office, a group of Year 10
girls turned their heads to watch him walk away from them, admiring the
way his shorts hugged his well-shaped bum. Although he was a handsome
man, Pete's bum was definitely his best feature and most of the gay
teenage boys who had passed through the school had spent hours wanking,
dreaming of burying their face in their teacher's pert backside.

He stepped into his office and closed the door behind him, not wanting to
be disturbed unless it was absolutely necessary. He threw his bag into
the corner then sat down behind his desk to log on. The school's
computers were slow and as he was waiting his hand once again wandered
down to his cock, squeezing it through the black shorts and the tight
white Calvin Klein boxer briefs underneath.

He looked over to the small couch by the door where parents would sit
when they came in to discuss their kids' behaviour and remembered the
time he had fucked a fit supply teacher on there last year. It was the
first time he had been unfaithful to his wife with another woman but by
that point he had gone without sex for over a year and was fit to burst.
He had felt horribly guilty afterwards though and promised himself that
he would never cheat on his wife with another woman again.

That didn't mean he couldn't think about it though, and he slipped his
hand inside his boxer briefs, closed his eyes and began to gently stroke
his under-appreciated cock, but he was almost immediately interrupted by
the bell signalling the start of the day.

Pete tucked his erection under the waistband of his shorts and went out
onto the corridor to usher pupils to their form rooms quickly and to nip
any potential poor behaviour in the bud before it got out of hand.

*

As the last few pupils trickled into their form rooms, Pete spotted three
Year 10 lads making their way slowly down the corridor.

"Hurry up lads!" he shouted, but they didn't pick up their pace.

Pete was confused. All three of the boys were in his GCSE PE class and
they had a good relationship, although they could cheeky at times and
were often in detention for not doing their homework. Jamie was on the
left of the three, his mid-length blond hair framing a handsome face with
big blue eyes. Billy was on the right, and while both he and Jamie were
very skinny, Billy was much taller and seemed somewhat lanky. Handsome
like Jamie, his head was topped with a mop of sandy brown hair that he
never brushed.

Pete rolled his eyes when he saw what was going on with the third boy,
Lewis Matthews. Jamie and Billy were almost dragging him down the
corridor, but Lewis's head was lolling from side to side. He was clearly
drunk and almost unconscious from it.

"What the hell is going on here?" he asked, sternly.

Jamie and Billy both looked sheepish but they knew better than to lie to
their teacher.

"He's pissed, sir," admitted Jamie.

"But we're not!" added Billy, quickly, eager not to get in trouble.

Pete rolled his eyes.

"Give him to me," he said to the two sober boys, "I'll deal with
this. Now get to class!"

The boys handed Lewis over to Pete and ran off down the corridor while
Pete hoisted Lewis over his shoulder and headed back towards his office.
Not only was Lewis drunk, but -- judging by the smell of his crotch
resting on Pete's shoulder -- he hadn't showered since football
training last night. Pete had spent enough time in teenage boys' locker
rooms to recognise the smell of sweat. He actually quite liked the smell
as it reminded him of good times when he used to play football with his
mates as a lad, but he was also not impressed that the boy had come to
school without washing.

He flung Lewis, now totally out of it and breathing heavily, onto the
couch in his office, closed the door and picked up the phone to call his
dad.

*

Lewis's dad was a builder who worked locally and had told Pete that he
couldn't get into school to pick his son up until that afternoon so Pete
had had to arrange cover for his lessons that morning so that he could
babysit the drunken lad.

He was secretly quite glad about this. Lewis was still out cold, which
meant he would have a good few hours of peace before he had do his lunch
duty.

Pete looked over at the boy sleeping on the sofa. Lewis had short blond
spiky hair and a freckly face that, although not as good-looking as Jamie
and Billy's, nevertheless attracted a lot of the girls. He was as skinny
as his friends but was significantly shorter, which obviously meant that
he was twice as loud and could get very annoying in class. Pete liked him
though, and was disappointed that he had fucked up so much by coming into
school pissed out of his face.

Lewis had gotten himself into an interesting position on the sofa, face
down with his knees tucked under himself and his bum in the air.

Pete's eyes rested on Lewis's bum. The trousers of his school uniform
were just getting too small for him and they hugged his teenage arse
tightly, so much so that you could see the outline of his briefs
underneath.

Pete smiled to himself; he had always had Lewis down as a boxer briefs
kind of guy like himself and was surprised that he hadn't seen him in
briefs when he was supervising the lads getting changed in the locker
room. His mind wondered, trying to remember what type of underwear the
other boys in his Year 10 GCSE PE class wore. Jamie always had tight
black boxers, whereas Billy seemed to prefer a looser boxer short. One
lad, Kian, had once come in wearing a pink thong as a joke, showing off
his pale white bum cheeks and stuffing all of his junk into a pouch at
the front.

His gaze shifted back to Lewis's bum sticking up in the air, his school
trousers so tight they looked like they were going to rip at the seams at
some point in the near future. As he continued to look at the
14-year-old's arse he was surprised to feel a familiar stirring in his
groin as blood rushed into his cock and it began to thicken and lengthen.
He had never thought about teenage boys sexually before, but it had been
two weeks since he'd last had a chance to wank at home and nearly two
years since he last had sex with his wife so anything and everything was
making him horny at the moment.

He turned to his computer to check his emails, trying to shake these new
lustful feelings for Lewis from his mind, but he kept finding his eyes
drawn back to the unconscious teenage boy lying a few feet away from him.

`I'd better check he's still breathing,' he told himself, well aware
that he was just giving himself an excuse to touch the boy.

He crossed the room and put his hand on Lewis's shoulder, shaking him
firmly. The only response he got was a loud snore before he went back to
sleeping peacefully.

Unable to help himself, Pete allowed his hand to slowly run down the back
of Lewis's blazer until it came to rest on the tight trousers clinging
to the boy's bum. He ran his hand around the edges of the teenager's
arse and then traced the visible line of his briefs with his finger
before giving each cheek a slow but firm squeeze. Lewis was so skinny
that there wasn't much to feel, but the mere fact that he had a
14-year-old boy's bum in his hand made Pete's cock feel harder than it
ever had before.

He slipped his left hand into his shorts and began to pull on his own
nine inches as he continued to run his right hand across Lewis's bum,
examining every inch by rubbing, squeezing and poking. As he poked the
area where he thought the boy's hole might be his previous thought
became reality as the back trouser seam split and Pete's finger pushed
into Lewis's crack through his newly exposed briefs.

From the little he could see of them, the teenager's briefs looked old
and well-used, and judging by the colour of them and the smell of crotch
reaching Pete's nose, Lewis clearly hadn't changed them in a few days.
As he started to jerk himself harder and harder, Pete bent down and
placed his nose into the rip in the trousers, inhaling deeply and
enjoying the musky scent of an unwashed teenager.

Pushing all feelings of guilt aside, Pete took both hands and in one move
he ripped Lewis's trousers even more, revealing his tiny backside and
stained white briefs. In his next move he pulled the fabric of Lewis's
briefs so hard that they ripped as well, revealing the boy's smooth
white cheeks either side of his crack.

He bent down to sniff again but couldn't stop himself from sticking his
tongue out and gently running it along the crack, then pulled the cheeks
apart to get a taste of his hole. As he slowly pushed his tongue into the
14-year-old's tight anus his own cock felt like it was about to explode.
He pushed his tongue in deeper and deeper, savouring the taste of teenage
sweat and the feel of the boy's arse pushing against his face.

Lewis's hole was now nicely lubricated by Pete's saliva and the teacher
looked up to check that the boy was still asleep before sucking his right
index finger and pushing it firmly inside the teenage asshole in front of
him. Lewis didn't even flinch as Pete moved his finger in and out of the
tight hole, before adding his middle finger to fuck the boy with two
fingers, whilst furiously wanking his own cock in his shorts with his
other hand.

Pete was confident that his pupil was pretty much comatose at this point
and, with two fingers still inside the boy, he slid his other arm
underneath him and carried him over to the desk, lying his torso on the
top and letting his legs and down. He undid Lewis's trousers and the
front and pulled them down his skinny legs along with his tattered briefs
so they hung around his ankles.

The deputy headteacher pulled the waistband of his shorts and boxer
briefs down so his fat balls and even fatter cock sat above them. He spat
on his hand and rubbed it into his thick seven-inch dick. A small voice
in the back of his head was telling him to stop, that this was wrong and
that he should end it now, but at this point Pete was not thinking with
his head.

Using his left hand to pull Lewis's cheeks slightly apart, Pete then
used his right hand to guide his cock to the boy's anus, rubbing it
gently on the opening. He slowly began to push it in, enjoying the
resistance the teenager's tight hole was giving and the warmth of the
boy's insides that were gradually enveloping his cock. He pushed in
deeper and deeper until his big balls slapped again Lewis's small ones
and he could push no further.

Lewis still did not make a move and Pete lifted his arm up to check
whether he was awake, getting his answer when it fell straight back to
the desk again. Fucking a teenage boy was one thing, but when that
teenage boy was drunk and asleep it was a whole new level of horny.

Realising that nothing could wake the boy at this point, Paul picked up
the speed and fucked the fourteen-year-old hard and fast, grabbing onto
his waist so he could bury his dick as deep as possible inside him. He
slowed the pace a little, not wanting to climax too soon and waste an
opportunity that might never come along again, though he continued to
fuck the teenager hard and deep.

Just as he was considering picking up the pace again, he had a horrible
feeling that he was being watched. He turned to the door and saw Lewis's
dad standing there, watching the deputy headteacher fuck his Year 10 son.

Pete froze, his dick still deep inside Lewis and met the boy's father's
angry gaze just as a small voice whispered "please don't stop."

***

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