Date: Sun, 4 Sep 2016 13:48:29 +0000
From: Andy Brown <andybrown2000@outlook.com>
Subject: Tutoring Dylan - chapter 4

Tutoring Dylan - chapter 4


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.

Please support Nifty with a financial donation - whatever you can afford -
so that this archive of stories can remain free and available.  Just go to
http://donate.nifty.org/

Thanks to everyone for the continued feedback, it's a great encouragement!
Although I've already planned what the 30 items on Dylan and Andy's list
are, I am open to suggestions of adding in some other activities for them
to try.

***

From the end of chapter 3:

"Now who's the dirty little sod!" he joked, throwing my words back at me.
I pulled him to me and hugged him close feeling the warmth of his body.  I
could still smell the remnants of his cum and my dick throbbed.  I was
pretty sure Dylan felt it, but I'm sure he didn't mind.  I then let go of
him, and as I did so I lowered my head and pressed my lips against his.
They were soft and warm.  It was like an electric shock passing between us
and both of our eyes went wide from the sensation.  We stood there for what
seemed like an eternity with our lips just touching, savouring the moment
of our first proper contact.

"See you next time," I said as I pulled away from him and opened the front
door.


***


The drive home from Dylan's house felt painfully slow although traffic was
fairly light for a Saturday morning.  I was eager to return to my house and
watch the show that Dylan had put on for me.

Once home I raced to my bedroom, shucked off my clothes and watched the
video on my phone.  I daren't touch my dick for fear I would blow too
early.  As I saw Dylan shoot his load on screen, I began to stroke my
nearly 7 inch boner.  I was so worked up that it only took a dozen or so
strokes to bring me over the edge as I exploded all over my chest and
stomach.

I lay there for a few moments contemplating what I'd done.  A feeling of
guilt began to wash over me.  I'd just jerked off to a video of a 13 year
old boy!  Surely, this is wrong?  If anyone found out I'd be arrested.

Disgusted with myself I turned my phone off and grabbed yesterday's
underwear out of the laundry basket to clean myself up with.  Once cleaned
up, I redressed and went downstairs to make some lunch.

As I sat munching a cheese and pickle sandwich I couldn't shake off the
disgusted feeling I had with myself.  What I'd just done was illegal and
immoral.  I picked up my phone, ready to delete the video.  But as I turned
the phone back on the screen returned to where the video had paused with a
screenshot of Dylan.  Naked and still hard.  Cum visible on his chest and
abs.  And a great big smile plastered on his face.

Yes it may be illegal.  And maybe it was immoral.  But he wanted it.  My
Dylan wanted it to happen.  He'd been wanting it for weeks, months, maybe
even years.  How could I deny him the experiences he so desperately longed
for?  After all, it had been clear from the conversation I'd had with his
parents that Dylan would make this happen one way or another.  If not with
me, then with some stranger off the internet, and who knows what trouble
that might lead him into.

I steeled myself.  I had to do this, for Dylan's sake if nothing else.  I
had to put the illegality of the situation to one side and focus on doing
my best to give Dylan the pleasure and the experiences he so desperately
yearned for.  We'd have to be careful, of course, and make sure nobody
outside his parents and his sister found out what was going on.  I
certainly wasn't going to tell anyone.  And I trusted Dylan wouldn't
either.  His parents had guaranteed their silence and I only hoped that
they'd made Imogen aware of what the repercussions would be for all of us
if she let anything slip to her friends at school.

The moral side of things was more difficult.  I'd been with younger guys
before.  Heck I'd dated a 19 year old uni student just a couple of years
ago.  But Dylan was much younger than 19.  Was it right for me to do the
things with him that I was planning on doing?

For a moment I cast my mind back to when I was his age.  At 13 I was dating
a girl called Jennifer: my attempt to fit in with the rest of my friends
who talked almost incessantly about which girl in our year had the nicest
tits and which pop star they'd most like to shag - yeah boy's, in your
dreams!  The 90s wasn't known for its tolerance and so I remained firmly in
the closet until I was 18 and had gone to uni.  Not that I hadn't managed
to mess around with a few friends during my teenage years mind you.  In
many ways I was jealous of Dylan growing up as a teenager today.  Although
he'd been outed as gay on Facebook, his friends at school had been
incredibly supportive and accepting by the sounds of it.  I envied him that
freedom.  He was going to have those teenage years - that time when you're
at your horniest, wanting to explore everything and having no concern for
risk - being out as gay and noone really seeming to batter much of an
eyelid.  What I wouldn't have given for that!  Instead my teenage years
were filled with lust filled fantasies of my classmates, slowly downloaded
pornography, and the occasional fumble with a friend.  If I were in his
shoes now, I'd jump at the chance to do what he's doing.

My mind was made up.  If this is what Dylan wants, then this is what Dylan
will get.  At 13 he's old enough to decide that for himself, I reasoned.
I'll make sure he's happy with what we are doing each time, and if he's
happy then why shouldn't I be?


***


I drove over to Dylan's house again the following Thursday evening, having
already arranged for his parents to take Imogen and Tommy out for the
evening.

Walking up to the door I felt far more relaxed than I had done on my
previous visit, with my mind now more at ease with what I was doing with
Dylan.  I rang the doorbell, this time Dylan wasn't nervously looking out
for me.

After a few moments the door opened and I was once again treated to the
delightful sight of the beauty that is Dylan, his hair styled in the way I
was getting quite used to seeing.  Today he wore a tight fitting white
t-shirt with short green sleeves which showed off his chest and his
developing arm muscles nicely.  It was a warm evening, so Dylan had opted
for blue jeans cut-off just below the knee.  His feet were bare.  We
greeted each other with a quick hug.

"Back in the lounge again tonight?" Dylan asked me.

"Ummm, no," I pondered.  "I think for today's session we'll head up to your
room."

Dylan's eyes lit up, clearly thinking we must be taking things up a notch.
"Excellent!" he said excitedly, and grabbing my hand he pulled me up to his
room.  Once there he launched himself onto his bed, bouncing a couple of
times as he did so.  His bed covers were once again a mess and I noticed a
few clothes scattered on his floor that obviously hadn't made it into his
laundry basket yet, as well as a bowl and an empty bottle sitting on his
desk.  That's teenage boys for you, I smiled to myself.

As Dylan had spread himself out on the bed, I sat myself on the swivel
chair that was parked next to his desk.  "So, what are we doing today?"
Dylan asked enthusiastically.

"Well I thought we'd have a chat," I told him.  He looked slightly forlorn,
obviously hoping to experience more of what we'd done last time.  "Don't
worry," I added giving him a reassuring wink, "that's not all we're going
to do today.  But part of what I see my role is as your 'gay sex tutor'"
making speech marks in the air with my fingers as I said this and causing
him to chuckle, obviously remembering our many SPaG lessons on punctuation
marks, "is to learn more about you and help you learn more about yourself."

"But why do you need to learn more about me?" he asked.  "Didn't you find
out enough about me when you taught me for two years?"

"Well obviously I found out some things about you," I said.  "Like how you
write 'are' instead of 'our', that you can never remember what 7x8 is, and
that you can do cartwheels better than anyone else I know."  He smiled.
"But as your teacher I never really knew you.  And there's so much more I
want to find out.  What do you fantasise about when you lay in bed at
night?  Is there anyone at school that you fancy?  How are you feeling
about life?  Have you enjoyed what we've done together so far?  Is there
anything you haven't enjoyed?  Which things are you most looking forward to
trying?  Which things are you a little nervous about?  Is there anything
you wanted to find out about on the internet but couldn't?  You see,
there's so much I want to find out about you Dylan Williams."

"Sheesh.  So what do you wanna know first?" he asked.

"How about telling me about our session on Saturday," I suggested.  "Did
you enjoy it?  Actually, before you tell me, I need you to promise me
something."

"What?" Dylan asked, sitting up on the bed.

"Please tell me if we do anything you're not comfortable with.  If there
is, tell me to stop.  Immediately," I said firmly.  "I don't mean if you're
a bit nervous - nerves are only to be expected when you do some things for
the first time - but tell me to stop if something hurts too much, or if you
really don't like something, or if you just don't feel ready to do it yet.
I won't be upset.  And I won't get mad at you.  But I need to know.  I need
to know you're happy.  Happy with what we're doing."  I could feel my voice
crack a bit as I said these things, the emotions that had been racing round
my head since Saturday coming to the fore.

"I promise," Dylan said softly.  As he did so, he placed his hand on my
knee.

"Thanks," I replied as I tried to compose myself again.  "So, did you enjoy
what we did on Saturday?"

"It was awesome!" he said with a beaming smile on his face.  "At first it
felt a bit weird taking my clothes off in front of you.  But then I thought
it's only like when we used to get changed in the classroom and you'd leer
at me..."

"Hey!" I protested.  "You make me sound like a dirty old pervert."  Dylan
smirked.  "Okay, so I suppose I am a pervert.  And dirty.  But I'm not that
old!"

"Only teasing," he giggled.  "But it was just like been back in the
classroom.  And it was kind of exciting knowing you were watching me and I
got a hardon.  And then I got down to my boxers and I got a bit nervous.
No one's seen me properly naked for a few years, and I didn't know what
you'd think..."

"Well, except your mum," I reminded him, causing him to blush.

"Thanks!  Oh, and I suppose Luke too," he added.  "But no one else.  I
thought maybe you'd laugh or just walk out once you saw it.  But you
didn't.  You said I was incredible.  No one's ever said anything like that
to me before.  Well my mum tells me how handsome I am, but it's not the
same.  You had this look in your eyes.  You looked sort of...hungry.  And
then when you told me to have a wank in front of you, I thought you were
joking.  I was really nervous at first.  I couldn't even look at you, and I
could feel my hands shaking.  But once I started to get into it, I sort of
forgot you were there, and then I looked up, and you were staring at me
with that hungry look in your eyes again and a great big smile on your
face.  You were obviously enjoying watching me, and I got a tingly feeling
in my stomach.  So I thought I'd put on a bit of a show for you, especially
when you started videoing me.  And when I came it was magnificent.  It was
like, really powerful."

"Thanks Dylan.  I'm really pleased you enjoyed yourself."

"And do I get to see the video now?" Dylan asked.

"Oh...yeah...nearly forgot about that," I said.  "Pass me your iPad and
I'll transfer it from my phone."  Dylan handed over his iPad and the cable
we needed, and within moments the video was safely stored on the device.
"Just remember to make sure no one else sees it," I told him.

"Of course I won't.  I don't want that being shared all over school."  He
laughed nervously, thinking about what could happen.

"And how are things between you and Luke now?" I asked, remembering what
he'd told me about their sleepover.

"I think he hates me," Dylan said sadly.  "He keeps ignoring me.  He even
asked to be moved in history, telling the teacher that he couldn't see the
board properly at the back.  But I know that he just doesn't want to sit
next to me anymore.  He's being such a wanker about it all."

"Give it time," I advised, placing my hand on his knee whilst smiling
inwardly about his choice of phrase.  "And maybe talk to him.  Just the two
of you.  I think you maybe just scared him when you put your hand on his
dick like that.  One thing you learn with relationships is its best to talk
to each other, to find out if you're both thinking and wanting the same
things."

"I suppose you're right," Dylan mumbled sounding unconvinced.

"Now before we get on to today's activities, I want to talk a bit more
about this list of ours."  Dylan's eyes lit up.  I'd clearly peaked his
interest once more.  "What are you most looking forward to doing?"

Dylan blushed a little before replying.  "Getting to touch you.  Down
there."  He cast his eyes down towards my crotch.

I chuckled to myself about his eagerness.  "And are there any you're
worried about?" I asked him.

"A few," he said nervously.  "I'm sort of worried that some...might hurt."

"I think some of them are meant to hurt," I replied.

"I know," he cringed, obviously embarrassed that I knew which ones he was
referring to.  "But you won't really hurt me, will you?  That's why I chose
you.  Because I trust you."

My heart melted.  "Of course I won't hurt you.  At least not too much,
anyway."  We both giggled.

"So are you going to tell me what else you added to the list.  I presume
we've done some of them already.  Taking off my clothes and wanking in
front of you.  Neither of those were on my list!" he said incredulously.

"And only one of them was on mine.  Taking off your clothes."  A sly grin
appeared on Dylan's face.  "The wanking sort of came to me once I'd seen
how hard you were.  I thought it would be rude of me not to let you!" I
smirked.

Dylan smiled.  "I knew you were a dirty old perv," he said.  "So another 9
left on your list then.  You gonna tell me what they are?"

"Not a chance," I replied.  "But I can tell you that both things we're
gonna do today are from your list."  His eyes widened at this.  "First, I
think it's time I got my hands on you."

If it were possible, I think Dylan's eyes widened even more.  I could sense
his brain was working overtime as he considered the possibilities.

"Stand up," I instructed.

Dylan hopped off the bed and stood in front of me.  As he did so I stood up
too, pushing the chair back under the desk and closing the blind at his
window.  I faced this beautiful creature and then leant in, bringing our
lips into contact with each other.  With our lips pushing ever tighter
together I grabbed the bottom of his t-shirt pulling it up to firstly
expose his belly button, then his abs, and finally his chest.  Dylan
naturally lifted his arms as I did so.  I broke the kiss to allow me to
pull the top over his head and off his body.  I tossed the garment onto the
floor.  I put my hands on his shoulders, feeling the softness of his skin.
Slowly I moved my hands down his body running my hands over the definition
in his chest and grazing his erect nipples with my thumbs as they passed.
I carried on further down enthralled by the way his abdominal area felt
hard yet soft at the same time.

I dropped to my knees and moved my hands to the top of his jeans, the black
waistband of his underwear peaking out of the top.  Bringing my hands
downwards and outwards I used my thumbs to circle around his crotch,
drawing a moan of pleasure from Dylan.  Going down I felt the firmness of
his thighs and as I reached his knees I let my hands fall down to my sides.
I looked up to see Dylan's torso moving in and out as his breath quickened.

My hands moved back up to his jeans, quickly undoing his button and then
sliding down his zipper.  Not giving him chance to react I pulled his jeans
down, letting them pool around his ankles.  I looked up to see an obvious
bulge in Dylan's black boxer briefs.  I leant in closer and inhaled.  Pure
boy - sweet yet a little tangy.  The tightness of his pants accentuated the
shape of his erection.  Carefully I placed my thumb at its base and slowly
stroked up his shaft, feeling the ridge on my way to his tip.  Dylan gasped
with pleasure and a small wet spot emerged under my thumb.

"Enjoying this?" I asked him.

"Yeah," came the reply, his voice shaking with excitement.

Once again I took my hands away from this enthralling contact and hooked my
thumbs into his waistband.  Pushing down, the beauty of his erection
emerged as it sprang back into place, having been pushed downwards with his
boxers.  Slowly I reached out my hand and stroked down his dick using just
a finger, feeling the smoothness of his skin and the heat emanating from
it.  Dylan visibly shivered.  A bead of precum emerged at the tip and using
my thumb I rubbed this over the head of his erection, eliciting another
gasp of pleasure from him.

"You okay?" I asked.  Lost for words, Dylan simply nodded.  "Good.  Then
get yourself on the bed."

Untangling his feet from his jeans and underwear, Dylan moved over towards
the bed.  Meanwhile I opened his desk drawer and grabbed his tube of lube.

I turned around and there he was, this naked beauty laid spread out on the
bed, one hand behind his head showing off the sparse hair in his pit, his
erection throbbing with anticipation.  Slowly I walked over to where he
lay.  Taking the cap off the lube I squeezed several blobs onto his dick
and watched him squeam with shock as the cold liquid landed on his organ.

I sat down on the edge of the bed and reached out, slowly wrapping a couple
of fingers around his shaft.  Gently I stroked them up his hot dick,
spreading the lube over his glans and back down his shaft.  Dylan moaned as
my thumb circled round his glans.  I repeated the motion just under his
ridge.  Dylan moaned louder as I hit what was clearly a sensitive spot.
Gradually I worked my hand up and down his shaft, occasionally using my
thumb to circle his head or ridge, causing him to gasp loudly each time I
did so.

My other hand worked its way up his body, stroking first his abdomen and
then his chest.  I spent some time rubbing first one nipple, then the
other, causing yelps of joy from my beautiful boy.  I moved my hand back
down, sliding over his pubic area and rubbing the small patch of soft downy
hair he had there.  My index finger grazed the base of his penis and Dylan
mewed in delight.  I could sense he wouldn't last much longer so as I
continued to wank him, I reached my left hand down and started to stroke
his cum filled balls, feeling the smoothness of his sac and causing him to
gasp once more.

This sent him closer to the edge.  I sped up my pace, causing Dylan to
begin gasping louder and for his chest to expand quicker.  With a final
gasp, Dylan's dick seemed to become even harder and his hole opened
shooting a streamer of cum up onto his chest.  His first shot hit him right
between his nipples before he shot another 3 watery squirts over his abs,
gradually tapering off and leaking over my hand.  I continued to stroke him
slowly while he basked in his orgasm.  Soon he started to squirm, telling
me that it was clearly becoming uncomfortable for him.

I was so, so tempted to lick my hand clean of his sweet boy cum, but I
reminded myself that that treat was reserved for another day.  I leaned
forward and gave my sweaty and satisfied boy a quick kiss on the lips.

After a few moments I climbed off the bed and grabbed his cum rag from his
desk drawer.  I wiped the dribbles of cum that had landed on my fingers,
then handed it to Dylan so he could clean himself up too.

Once the remnants of his orgasm had been cleaned up, Dylan swung his legs
over the side of the bed and made to grab his underwear.  "Not yet," I
said, stopping him in his tracks.  "There's something else we've got to do
first."

And with that I put one arm around his back and pulled him up off the bed
and towards me.  Turning him towards me I peered into his warm brown eyes.
I placed my hand gently under his chin, lifting his face close to mine.  I
felt the muscles in Dylan's back tense up, anxious about what was about to
happen but longing for it at the same time.  Looking down at him I moved my
head forward and our lips touched.  Eventually he relaxed into the kiss and
he pressed his lips more firmly against mine.  I could smell the sweetness
of his breath and the heat from him as he pressed himself against me.
Slowly I opened my lips allowing my tongue to hesitantly lick his lips.
Dylan opened his mouth and our tongues touched for the first time.  I felt
a spark shoot through my body.  The taste of him was overpowering and the
heat from his mouth was unbelievable.  It was like nothing I'd ever
experienced before.  As we sank into our feelings we continued to kiss, our
tongues wrestling with each other, our bodies pulled so close it was as if
we were one.  Dylan was hard again and I could feel his erection pressing
against my thigh.  No doubt he could feel mine against his abdomen.
Remembering the promise I had made myself to take things slowly I gently
withdrew the kiss and peered back down at Dylan's lust filled eyes.

"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.


***

End of chapter 4.  Hope you all enjoyed it!  Things are looking busy at
work over the next couple of weeks so it may be a little bit of a wait
until chapter 5 is posted, so please bear with me.

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