Date: Sun, 11 Sep 2016 20:49:24 +0000
From: Andy Brown <andybrown2000@outlook.com>
Subject: Tutoring Dylan - chapter 5

Tutoring Dylan - chapter 5


Disclaimer: The following is a work of fiction which features sexual
activity between a teenage boy and a grown man.  If you do not want to read
such a story, or it is illegal for you to do so because of your age or
where you live, then I recommend you go read something else instead.  The
characters in this story do in fact exist. However, none of the things in
this story have ever happened. Also, clearly to protect the characters, I
have changed their names and some facts about their lives.

This story is property of the author; please do not post it elsewhere
without the author's permission.

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Sorry for the delay, but life unfortunately has gotten in the way of
writing over the past week or so.  Thanks to everyone for the ideas you've
shared with me and the continued feedback, it's a great encouragement!

***

From the end of chapter 4:

"Fucking hell," Dylan exclaimed as he ran his hand through his hair.  "That
was amazing.  You undressing me, touching me, jerking me off.  I don't
think I've ever cum so hard," he said breathlessly.  "And then the
kiss. Woah.  It was like a bolt of electricity shooting through me, but
like, in a good way."

"Yeah, I know what you mean," I told him.  "See you next time."  And with
that I walked out of his bedroom leaving him standing there naked and hard
as a nail.


***


I must have broken the speed limit for most of my journey home, so eager
was I to relieve myself.  Hardly concentrating on the road as I drove, I
kept replaying the sensations of what had just happened in my mind: the
feel of Dylan's skin, his burgeoning scent, the heat that emanated from his
erection, and the sweet taste of his mouth.

As I had done mere days before I stripped my clothes off as soon as I
reached home and laid on my bed.  Replaying in my mind what I'd done with
Dylan, I soon shot ropes of hot cum all over myself, some even hitting my
cheek.

I lay there panting, wallowing in post orgasmic bliss.  But this time there
were no regrets.  No feeling of guilt or shame.  Instead just an
overwhelming sense of happiness.  Dylan had enjoyed what we'd done.  I'd
enjoyed it too.

As I lay there with my cum slowly drying on my chest it struck me how
different my life had turned out to the way I'd hoped it would.  I thought
back to my 21 year old, fresh out of university with little more than a
suitcase of clothes, several boxes of books, an overdraft, and a head full
of dreams.  Ready to take on the world, but with no idea of what to do
next.  I longed to be a writer since I was a young boy, and I'd just spent
the past three years studying English Literature, but my parents had
kyboshed the idea telling me to get a job as they weren't prepared to 'work
themselves to the bone just so you can faff about all day.'  So a job it
was, as a teaching assistant at a secondary school just a short walk from
my parent's house.  Whilst the pay wasn't great I only worked 7 hours a day
and had school holidays free which meant I could do a bit of writing on the
side.

I spent much of my spare time with a pen in my hand (I guess I was old
fashioned in that regard) and managed to complete several stories which I
sent off to various publishers.  One publisher included one of my pieces in
an anthology of other short stories, which I was over the moon about.  At
last I'd fulfilled my dream of being a published author.  But the sales
were low and the royalties I received certainly weren't enough for me to
live off.

However working as a teaching assistant turned out to be quite good fun.  I
tended to spend most of my time working with kids who either had learning
difficulties or behavioural problems.  The former category were easier and
it was quite gratifying to see them slowly improve over the two years I
worked at the school.  Those with behaviour problems were frustrating.  One
minute they'd be getting on with their work okay, the next minute the
slightest thing had set them off, their work was thrown across the desk and
they were charging down the corridor.  Needless to say I spent quite a lot
of my time traipsing down hallways trying to catch them up!

The other issue was the boys.  I'd discovered that I liked looking at other
boys when I was about 10, and realised that I must be gay in my early teens
as I started to jerk off thinking about my male classmates.  As I grew
older my tastes didn't.  Even at aged 18 when I was getting ready to sit my
A levels I still fantasised about the boys in years 8 and 9.  When I went
off to uni I dated and slept with several guys around my own age, but my
thoughts always crept back to boys in the early stages of puberty.

It was becoming hard (in more than one sense of the word) to be faced with
this temptation day after day at the school.  So it was a relief when my
parents told me it was time for me to 'get a proper job now.'  I decided I
may as well stick with what I knew best - the world of education - and
train to be a teacher.  But to avoid the temptations I'd faced (and just
about managed to control myself from succumbing to) I decided it would be
best to drop down the age range and train to be a primary school teacher.

The training year was incredibly tiring but it gave me the qualification I
needed, and I managed to land a job teaching in an inner city school for a
year.  With a proper wage now guaranteed I moved out of my parent's place
and rented a small flat.  The following year flew by as I learnt what it
takes to control and teach a classroom of 10 year olds with their myriad of
challenging backgrounds.  Shortly after Christmas I was told that despite
doing an excellent job so far my contract wouldn't be renewed due to budget
constraints.  Thankfully I managed to secure a position at a leafy lane
school in a small village, initially in year 4 before being moved up to
year 6 after a year.

The year training and the year in the inner city gave me a break from
temptation.  Whilst there were a few boys in my classes who were cute, none
of them particularly turned me on.  I must have made the right choice, or
so I thought.  But then at the new school there was Dylan.  In year 4 he
was probably the cutest boy I'd ever seen but still not sexually appealing;
my tastes had never gone quite that young.  But by year 6 I don't know how
I managed to keep my hands off him!  Somehow I did, except of course for
the costume measuring.

Dylan then left to go to high school along with the rest of his class.  I
got a new cohort of children but none of the boys came anywhere near the
appeal of Dylan.  In all honesty, it was a tough year.  I missed Dylan,
this new class weren't the smartest, the head teacher had discovered an
obsession with performance data and observations, we'd had a less than
brilliant visit from Ofsted, and I'd broken up with my boyfriend just
before Christmas.  By the time we'd got to the SATs in May I'd had enough.
I needed a break.  I handed in my resignation letter and by the middle of
July I had left the school and left teaching too, at least temporarily.

I hadn't been sure what to do next.  I'd never intended to go into teaching
in the first place, it had just sort of happened.  I applied for various
things, none of which I especially wanted to do, but all would pay a decent
wage and keep a roof over my head.  In the end I'd been offered a job at a
call centre working for an online bank.  The pay was respectable though
less than my salary as a teacher, but my colleagues were friendly, and with
no paperwork to take home at the end of a shift I had spare time on my
hands again for the first time in many years.  I threw myself back into my
writing.  I also had time to take up swimming and cycling again, and even
managed to spend a few hours each week decorating the house I'd bought a
couple of years earlier.

In many ways the phone call from Mrs Williams had been a great
inconvenience.  Whilst tutoring would bring in some useful extra money, I
had got used to having extra time on my hands and had no great desire to
give that up even if it was to tutor a good looking 13 year old boy.

My view obviously changed considerably once I learnt the exact nature of
the assignment she was offering, and I knew I was going to really enjoy the
next few months with Dylan.  Although I wasn't the professional writer I'd
dreamed of for so long, my life wasn't going too badly.


***


Unfortunately a combination of my shift pattern at the call centre and
Dylan's gymnastics practices prevented me from scheduling another session
with Dylan as quickly as I'd have liked.  But almost a week after our last
meeting, I was once again sat with Dylan in his bedroom.  He was occupying
the bed again leaving me relegated to his swivel chair.

We'd spent quite some time discussing what we had done last time: me
undressing him, then jerking him off, followed by our first proper kiss.
Dylan told me how strange it had felt to have someone else undress him, an
experience he hadn't had since he was a small child.  But he also found it
a real turn on, the thought that someone - me - wanted so badly to see him
naked.  He was still a little uncomfortable with me seeing him naked, he
told me, but it was beginning to feel a bit easier.  Apparently he'd been
fantasising about it for the past couple of years, even before the
measuring session, and was amazed that he'd finally managed to have it
happen.

"So what else have you been fantasising about?" I asked him.

Dylan raised an eyebrow and a cheeky grin spread across his face.  "You
really want to know?  It might shock you," he replied.

"Dylan," I hit back with a similar grin on my face, "this might come as a
great surprise to you but despite having been your teacher, I've been
around a bit.  I hardly think you're gonna shock me."

"Oh yeah," he said.  "You don't really think about teachers having a sex
life, but I suppose you must do.  I mean I've imagined you and me doing
things together but..."

"Fantasised about the two of us together have you?" I questioned him
teasingly.  "So what are these fantasies where you and me 'do things
together', eh?"

Dylan blushed.  Geez, I love it when he does that.  "Well... you know..."
he stuttered.  "Look, you know pretty much all of them already... they were
on that list you got me to write."

"You mean, you've fantasised about doing all of those things with me?" I
asked.

He rolled his eyes at me.  "Bit slow to catch on, aren't you?"

"Woah," I said, almost stunned into silence.  I knew he trusted me.  That
he found me attractive, maybe had a bit of a crush on me even.  That, in a
way, he looked up to me and wanted my approval.  But it had never crossed
my mind that he'd had the same kind of fantasies about me as I'd had about
him.  It took me a few moments to compose myself.  "Okay so apart from
those things that you want to happen, what else do you fantasise about?"
He looked blankly at me clearly wondering why I was asking something he
thought he'd already answered.  "What I mean is what else happens in these
fantasies of yours?  Where are we?  What's going on around us?  How are we
dressed?  Is there anyone else involved?"

Dylan grimaced, obviously a little wary of opening up his most secret
desires before me.  "Well, one of them has to do with that day you measured
me for that Tarzan costume," he began.  "And you're measuring me again,
just like you did then.  But instead of wearing your normal clothes, you're
dressed like a doctor with a white coat and a stethoscope and stuff.  And
when I get down to my boxers you insist that I take them off as you need to
measure me 'down there'.  And you touch me and measure me everywhere.  And
I spring a boner and you're down on your knees and you start licking it and
then you take it in your mouth and suck me off and I shoot inside your
mouth... and you swallow it."

"Shall I tell you something Dylan?" I asked.

"What?"

"I have that fantasy too," I said.  "Though in mine I'm not dressed like a
doctor, but the rest happens just like yours.  Except..."

"Except what?" he asked eagerly.

"We kiss.  And I share your cum with you."

"Ewww, that's gross!" he protested.  "But kinda hot at the same time."

I smiled at his remark.  "Any others you'd like to share?" I asked.

"There's another one that happens in school too.  I've been naughty in
class and you tell me to stay behind afterwards.  I do.  You start telling
me off and tell me I've got to be punished.  So you pull me over your knee
and start smacking me.  Then you pull down my trousers and smack me again.
And then you peel my boxers down and keep on smacking me until my bum's
bright red.  You tell me I've still not been punished enough so you undo
your trousers and pull out your dick and make me suck it."

Wow, I thought to myself.  That's one maybe we'll have to try out.  "So you
enjoy getting a good spanking do you?" I asked him with a sly grin.

"I don't know.  Dad's not spanked me since I was little," he told me.  "But
I like watching videos of boys been spanked.  It looks really hot."  He
paused.  "In another one I'm in a room with another boy and we're laying on
a bed.  I don't know where we are, but we've got our tops off and our
shorts and pants are down by our ankles.  We're both having a wank and then
he reaches out and starts jerking me off.  So I reach out and jerk him off
too.  And then the door opens and you walk in and we panic and try to cover
up.  But you tell us to carry on, so we do.  And then you pull out your
dick and start wanking too.  Me and my friend both start to shoot and you
walk over to us and then you shoot all over us."

"Jeez, that is just... wow!" I said struggling for words.  A hundred
different thoughts ran through my head.  I didn't know whether to be happy
or shocked, proud or disturbed.  In the end, turned on won the day as my
cock strained against the confines of my underwear and copious amounts of
precum leaked out of the end.

"There's one more," Dylan continued.  "It involves Charlie from Imogen's
class."  Now that was interesting.  I knew Dylan's parents had talked to
Charlie about doing all of this with Dylan instead of me, but I hadn't
figured that Dylan was fantasising about him.  "We're in a changing room,
just me and him, and we go into the showers.  I look at him and I get hard.
He notices and asks me if I like what I see.  I don't know what to say.  He
grabs my boner and tells me it looks like I do.  I then notice that he's
hard too.  He pushes me down to my knees and tells me to suck him off.  I
begin by licking him and then I take his big hard dick into my mouth and
start sucking it.  He begins moaning.  Then I hear a voice asking what's
going on.  I look around and see you standing at the edge of the showers
just in a pair of shorts with a big bulge in the front.  I let go of
Charlie's dick.  You then slide your shorts down and walk over.  You stick
your dick in my face and I start sucking you instead.  Charlie then says
that if you're taking that end, he'll take the other.  He walks around me
and then spits on my arse.  He uses a finger to spread his spit all around
my hole and then he slides his finger into me.  Then he shoves another
finger in.  He pulls them both out and then shoves his hard dick in.  I try
to scream but I can't cos I'm still sucking you.  The two of you keep doing
it, you with your dick in my mouth, Charlie with his dick up my bum.  Then
you squirt in my mouth and Charlie squirts in my arse and then you both
pull out and I collapse on the shower floor."

For several moments I just sat there, staring at Dylan.  How I managed not
to cum whilst he was telling his story I'll never know.  I breathed out
heavily.  "Dylan," I told him, "that has to be one of the hottest things
I've ever heard."  If there was any way of making this happen I would make
sure it did.

"So what're we doing today?" he asked, almost as if the past ten minutes
hadn't happened.

"Oh," I replied, not fully taking in what he'd just had.  "Today's session?
Well we're going to do exactly the same as we did last session."  He looked
puzzled and a frown began to appear on his forehead.  "But this time, roles
reversed.  You're going to strip me.  Then jerk me off.  Sound good?"

His big brown eyes lit up and he burst into a great big smile.  "It sounds
awesome!" he replied.

Pushing my chair under the desk, I stood in front of Dylan.  "I'm all
yours!" I told him.

Dylan hopped off the bed and stood facing me, our bodies mere inches apart.
The look on his face was hard to read.  He seemed both excited at the
prospect of fulfilling a long held desire, yet at the same time nervous
about what he was about to do.

I could see him physically take a deep breath as his chest expanded and
then I felt his sweet vanilla breath as he exhaled.  For a moment I caught
myself wondering what he'd had for dinner.  He paused for a second before
extending his hands towards my body.  He reached upwards and began to
unbutton my shirt, starting at the top and working his way downwards.
Little by little I could feel first my chest and then my abdomen becoming
gradually more exposed.  Eventually he finished unbuttoning the shirt.  He
reached up once more, pulling the material over my shoulders and letting it
slide down my arms.  With a small wriggle from myself the garment soon
landed on the floor.

"Can you sit back on the chair Andy?" Dylan asked.  "It'll be easier to
take your socks off that way."

I did as he asked.  Dylan leant down and grabbed my left leg by the heel so
he could lift it upwards.  He rolled my trouser leg up slightly, exposing
part of my hairy shin.  As he pulled the sock off my foot, his fingers
stroked along my sole causing me to shiver slightly.  Dylan lifted my sock
to his nose and took a sniff.  I could hear him moan quietly as he took in
the smell.  Carefully he dropped my left leg to the ground and then
proceeded to remove the sock from my right foot.  Again he sniffed my sock
before discarding it.

I thought I heard a knock coming from downstairs, but I ignored it.  Dylan
didn't react either so either he hadn't heard anything or he was ignoring
it too.

"Shall I stand up again now?"  I asked.  He nodded.  As I stood before him,
Dylan tentatively reached out and unbuckled my belt.  Moving his hands to
the top of my black jeans he popped the button open.  Again he took a deep
breath steeling himself for the next reveal.  Ever so slowly, almost as if
worried something was about to leap out at him, he pulled the zipper down
giving him his first glimpse of my bright yellow underwear.  I knew that
there would be a sizeable bulge in my tight boxer briefs and by the look on
Dylan's face, he had noticed it too.  With another deep breath he grabbed
the waistband of my jeans and began to pull them: down my thighs, over my
knees, and finally pooled around my ankles.  I lifted my legs up, one at a
time, and stepped out of them.  Dylan reached down to pick them up, placing
them on top of the rest of my discarded clothing.

Moving back around, Dylan hooked his thumbs into the top of my underwear.
Time seemed to stand still.  For what felt like an eternity Dylan paused.
I waited.  Dylan didn't move.  I noticed his hands had begun to tremble.
Slowly I reached over and placed my hands on top of his.  I pushed down
gently helping Dylan to slide my final piece of clothing down my legs.

Dylan took a step back and gulped.  His mouth was agape.  He began to look
at me, almost as if noticing for the first time that I was no longer
wearing any clothes.  Looking up he first looked at my head: piercing green
eyes; a clean shaved face; a smattering of freckles across the bridge of my
nose; and topped off with short auburn hair, thinner on top than Dylan's
but with a similar swish to the right.  Looking further down he took in my
torso: the small smooth mounds of my chest topped with erect pink nipples;
tufts of auburn hair visible from my armpits; a flat, tight abdomen honed
from my recent hours in the pool and separated down the middle by a trail
of hair.  As his eyes travelled down my body he took in the sight of my
arms noting the modest size of my biceps and the light coating of hair on
my forearms.  Next his eyes darted down to my feet, size 9 and fairly
hairy.  The hair continued as his gaze travelled up my lower legs and onto
my muscly thighs, sculpted through my love of cycling.  Finally his gaze
rested on the sight he had longed to see for so long.  Hard and throbbing
my penis was just over seven inches in length, the foreskin peeling itself
back to show off the swollen purple glans, a bead of precum dripping from
its tip.  Underneath my two heavy balls lay inside their shaved sack.
Around the base of the pulsating organ was a modest patch of pubic hair,
trimmed short to keep it looking neat.

I suddenly realised that Dylan had not yet touched my body.  I was
confused.  Was he simply enjoying looking for the moment, overawed almost
by the experience?  Or was he too nervous to begin?  Another thought crept
into my head - maybe now he's seen me undressed he doesn't find me
attractive.  What if I actually repel him?  But I pushed that thought away.
After all he'd undressed me fully, if he'd changed his mind about me then
surely he'd have stopped.  Maybe he was waiting for my permission, still
looking upon me as his teacher.  Everything we'd done so far had been at my
instruction.  Was he waiting for me to tell him he could touch me?

"You can touch me, if you like," I suggested to him.  Still he stood there.
Clearly his nerves were getting the better of him and he needed me to take
control.  I grabbed his wrists and pulled him towards me so his hands were
placed on my chest.  He let out a short gasp.  "Touch me Dylan.  Feel my
chest.  Feel my torso."

Dylan held his hands rigidly in place for several moments.  Then he began
to move his hands downwards, grazing my nipples as he did so and causing me
to moan in delight.  His hands moved down my tight abdomen and as they
stroked over the V-lines at my hips I gasped once more with pleasure as
Dylan found one of my sensitive spots.  Next he explored my legs as his
hands worked their way down the outsides of my thighs and carried on until
they reached the floor, stroking the hair as he went.  He then worked his
way back up the inside of my legs sending shudders right through my body as
he stroked the inside of my thighs.  Once more he paused clearly knowing
what his next move would need to be but seemingly unsure of quite how to do
it.

 "Just think of it like your own," I told him reassuringly.  "Feel it.
Stroke it.  And remember with mine you can move the foreskin back and forth
so you won't need any lube."

He licked his lips and reached out with his thumb, tracing his way down my
erection from its tip to the base.  Even this little amount of touch had me
moaning with sheer happiness knowing whose hand it was doing the touching.

Dylan paused again, willing himself to go further.  He reached out again,
this time his fingers wrapped themselves around my shaft, his thumb curled
over the top.  A big grin broke out on his face, clearly delighted to
finally have his hand around what he had lusted after for so long.

Slowly at first, he began to pump his hand up and down my shaft getting
used to the unfamiliar workings of a penis other than his own.  Gradually
his pace began to quicken and he copied my movements from our last
encounter using his thumb to stimulate the head.  And stimulate me he did.
The sensations he was giving me were unbelievable and he soon had me
panting and groaning as his diminutive hand worked its way up and down my
cock.

"Dylan stop," I told him as he brought me close to orgasm.  He looked
disappointed, thinking he must have done something wrong.  "Don't worry," I
said reassuringly, "I just want to lay down on the bed.  It'll stop us from
having to clean your carpet afterwards"

As I laid down Dylan knelt on the bed, straddling my thighs.  Once again he
took hold of my cock and began to work it.  I had been so close before I
stopped him that it only took a minute or so more of him stroking me until
I blew.  I moaned loudly as six ropes of cum flew out of my cock,
splattering onto my chest and abdomen, a few smaller spurts trickling down
onto Dylan's hand.

"Fucking hell," I groaned.  "That was incredible.  Thank you."

Dylan didn't reply.  Instead he pulled his t-shirt over his head and used
it to clean my cum off his fingers.  He then stood up on the bed and
stripped off his shorts, socks and pants.  His body glowed with a thin
sheen of perspiration.  Kneeling back down he dipped two of his fingers
into the cum pooled in my belly button.  I thought for a moment he was
about to taste it, but realised I was wrong as he smeared it over his own
erection.  Using my cum as lubrication he began to jerk off.  Soon his hand
was little more than a blur as he raced towards his own orgasm, grunting
and groaning as he did so.  With a final gasp three squirts of his watery
cum flew out of his dick and joined my own load on my chest.

Exhausted from his experience, Dylan collapsed on top of me and our
combined loads smeared onto his chest as he did so.  I swept his hair
across his damp forehead and then kissed him.  Dylan melted into the kiss,
meeting my tongue with his own.  Wrapping my arms around him, I held him
close as our tongues continued to explore each other's mouths.

As we kissed my hands worked their way down his back and had their first
feel of his arse.  I ran a finger up his crack, extracting a muffled yelp
from Dylan.  After several minutes of passionate kissing, I rolled us onto
our sides and pulled my lips away from his.  We looked dreamily into each
other's eyes, both smiling after what we had done together.  Dylan sank
back into the pillow and soon nodded off to sleep.  I watched him for a
little while, taking in his beauty and thinking to myself how lucky I was.
My own eyelids began to grow heavy and sleep overtook me too.


***


I woke up with a start as I heard a door close downstairs.  "Dylan, are you
upstairs?" a voice called out from below.  "Is Andy still with you?"

Next to me I could feel Dylan stir.  "Hi mum," he called out, his voice a
little groggy.  "Yeah, I'm in my room.  Andy's still with me.  We'll be
down in a minute."

"That's okay," Sandra responded.  "Don't rush."

I clambered off the bed and fished Dylan's towel out of his desk drawer.
Dylan sat up and looked down at his body.  "Shit, it's got everywhere," he
muttered.

Turning around I swept the towel over Dylan's chest and torso, sponging up
the remnants of both of our loads.  Carefully I lifted up his penis,
delicately cleaning its tip.  I noticed a spot of cum had settled in his
sparse pubic hair which I mopped up with the corner of the towel.  As Dylan
began to get dressed I wiped the cum from my own body, sniffed the towel,
and then put my own clothes back on.


***


Once dressed we headed downstairs and met Sandra in the hallway.

"Evening Sandra," I said rather awkwardly.  It felt very strange to be
stood talking to the woman who's son had just jerked me off.

"Hi Andy," she responded.  "Things going well?"

"Yeah... fine," I replied.  I didn't really know what to say to her.  I
doubted she wanted a blow by blow account of what we'd been up to that
evening.  "I've got a couple of days off work this weekend.  Would it be
okay if I took Dylan away?"

She paused, obviously running through in her head any plans they currently
had.  "Well Dylan has his diving lesson on a Saturday morning," she said,
"but I suppose he could miss it this once."  She had obviously seen the
expression of excitement on Dylan's face when I'd mentioned taking him away
for the weekend.  "Where are you thinking of going?" she asked.

"I thought we could go camping," I replied.  "There's a nice little site I
know up in the Lakes.  It should only take us a couple of hours to get
there."

"Well that's fine by me," Sandra said.  "Does that sound okay to you
Dylan?"

"Too right," he said excitedly.  "It sounds awesome!"

"That's settled then," she said.  "What time do you want to pick him up?"

"I'm working the late shift Thursday and Friday," I replied, "so I could
probably do with a lie in Saturday morning.  How about if Dylan still goes
diving and then I pick him up after lunch.  Say half past one?"

"Great.  See you then," Sandra said as she went through to the lounge.

"Well I best be off now," I said to Dylan.  I put an arm around him and
pulled him in close to me.  We kissed.

"Thanks Andy," he said.  "I don't think I'll ever get tired of that."

I smiled to myself as I opened the front door.  "See you on Saturday," I
called out to him.


***

End of chapter 5.  Finally a description of Andy, as a number of you have
requested.

This is my first time writing on Nifty and so any feedback would be greatly
appreciated - andybrown2000@outlook.com