Date: Fri, 17 Feb 2017 14:45:51 +0000
From: Andy Brown <andybrown2000@outlook.com>
Subject: Tutoring Dylan - chapter 15

Tutoring Dylan - chapter 15


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***

From the end of chapter 14:

I opened the box again.

"Is there another one?" Dylan asked.

"Aha."

"Is it bigger?"  His voice trembled nervously.

I didn't reply.  Instead I ran the six inch, black, silicon shaft along his
crack, allowing him to feel the size for himself.  Although not as big as
my own cock, it wasn't far off.

"Oooohhhhhh!" he shivered.  I looked into his eyes.  They blazed with
excitement.


***


I pressed the dildo against his crack and started rubbing it around.
Lining the head up with his rosebud, I began to push.  Dylan gasped.

I pushed a little more, judging that a little force would be needed to get
it inside Dylan.  I knew I'd obviously pushed too hard as he let out a cry
of pain.  His hole closed tight and the toy was promptly expelled.

Putting the silicon implement to one side, I pulled the rope slightly,
bringing his bottom higher.  I worked his arse with one, then two, and
finally three fingers, taking care to try and stretch his opening.  Dylan
visibly relaxed beneath me.  As my fingertip massaged his prostate, Dylan
gasped, another drop of precum leaking out and dribbling onto his lips.  I
continued probing inside him, working my fingers around.

Anxious to try the dildo again, I pulled out and lined the head up.  Ever
so slowly, I pushed at his hole.  With my spare hand, I rubbed his lower
stomach, running my digits through his crop of pubic hair and along his
shaft.  This time, with his mind momentarily distracted, the head of the
toy slid in.  Dylan gasped as his hole stretched to accept it.  More precum
leaked out of the head of his twitching cock, landing in his now open
mouth.  With my spare hand, I grasped his hard member.  I slowly jacked it
a little, Dylan cooing in response.

I pushed the dildo in another inch.  Dylan gasped.  I leaned over and
lapped at his balls.  As I added a further inch, Dylan wriggled his arse as
if thirsting for more.

Another inch.  Dylan moaned with pleasure as the dildo rubbed his
boy-button.  With a final push, all six inches were embedded in his
boy-chute.  Dylan was panting, his forehead moist.  Yet his cock continued
to drip into his waiting mouth.  Despite the effort, he was enjoying it.

After giving the boy a few moments to rest, I drew the toy back slowly.
With just the head remaining inside, I pushed it back in, a little quicker
this time.  Dylan groaned again as I worked it past his sex-gland.  Once it
was it to the hilt, I again withdrew it.  I moved my hand away from his
dick, not wanting him to blow too soon.

Instinctively, Dylan started rocking his hips as I worked the dildo in and
out of him.  Louder and louder came his moans.  Sweat continued to bead on
his forehead as I pistoned the dildo into him.

"Faster, Andy!  Faster!" he instructed.

Not wanting to disappoint my teenage stud, I duly obliged, picking up the
pace of my thrusting.  Pre-jizz continued to flow into his waiting mouth as
the toy stroked his boy-button.  I could have carried on like this all day,
but I sensed that Dylan was needing release.  I grasped his shaft again.  A
few gentle pumps was all it took.

"Oh Andy!" Dylan cried out.  "I think I'm gonna..."

Warm jizz fired out of his member.  It looked so hot, seeing this young
stud's cum filling his own mouth.  He swallowed what he could, although a
final spurt from his cock dropped onto his lips.  Reaching out with his
tongue, he gathered it in.  As his orgasm enveloped him, I slowed my
assault on his boy-hole, before I began to pull the dildo back.  With a
sigh and a twitch, it popped out.

Reaching over, I untied the rope around Dylan's feet and gently lowered his
legs.  He grimaced slightly as his arse made contact with the bed.

Pulling off my damp underwear, I released my straining erection.  I
straddled Dylan and began to jerk off.  I knew, after watching that
scintillatingly hot scene, it wouldn't take long.  And it didn't.  As my
orgasm hit, I thrust my cock into Dylan's mouth.  Dutifully, he swallowed
every last drop, giving my head a final lick for good measure.

Sliding off, I lay down next to him.  Leaning over, we shared a long,
sensuous kiss, our arms enveloping each other.

Predictably, within moments he was fast asleep.  Time to enact my plan.  I
unwrapped myself from him and fetched what I needed from downstairs.  While
my boy slept I prepared him for when he woke up.  Even though it was a
complex procedure, involving me handling both his cock and his balls, he
didn't wake up.  His mum had once told me that he was such a heavy sleeper,
he'd once slept through their back yard being dug up by a pneumatic drill.
I laid down next to him again, pulling a sheet over us both.


***


I woke up early the following morning, needing to be in work by nine
o'clock.  I'd already had a quick shave and shower, thrown on some clothes,
and gone downstairs to grab a bowl of cereal.

"What the fuck!" I heard from upstairs.  "What have you done to me!?"

Putting my now empty bowl in the dishwasher, I raced back upstairs.  Dylan
was stood by our bed, naked as the day he was born, with a look on his face
that could have turned milk sour.  Encased around his penis was a cage,
padlocked carefully onto him, trapping his cock and balls inside.

"Dylan, I'm afraid I have some bad news," I told him.  "I've got to work
for most of the next week."  He looked indignant.  "I'm not sure I can
trust a teenage boy not to waste the whole of his time just watching porn
and masturbating."  He stared down at his encased cock again.  "It won't
intefere with your life too much," I continued.  "But you won't be able to
get hard or have a wank.  The hole at the end is so you can piss.  Oh, and
you can keep it on when you shower."

"But what if I need to take it off?" he asked in shock.

I pulled some keys out of my pocket and waved them at him.  "These are the
only keys to that padlock and I'll be looking after them."  I put them back
in my pocket.  "I'll pick you up from gymnastics this afternoon," I told
him.  "There's money on the kitchen table for the bus fare.  And help
yourself to whatever you want for breakfast and lunch."

I knew that this was going to be a hellish week for my teen boy, unable to
satisfy his natural desires, but I also knew that it would be worth it.
From previous discussions we'd had, I was aware that he usually jerked off
two or three times a day.  A week without unloading would help him learn
the joys of delayed gratification.

I watched as he pulled his boxers over his encaged genitals and slipped a
t-shirt over his head.  I pulled him towards me and kissed him, Dylan
grinding his body into me as I did so.  I could feel the cage pressing
against me and then there was a groan from Dylan.

"I see what you mean about not getting hard" he murmured.  Predictably,
kissing me had caused him to start chubbing up, but the restraint had put
an end to that.


***


Walking towards the bus stop, I stopped as I came to a post box.  Pulling a
pre-addressed envelope out of my bag, I slipped the keys into it.  After
licking the flap, I sealed it and popped it into the post box.

The bus ride into work was largely uneventful.  As usual, I spent the
journey people watching.  It had become a bit of a ritual of mine on my
commute.  It particularly amused me to watch fellow passengers talking on
their phone.  I often found myself imagining what the other side of the
conversation must be like.

This morning was no exception.  Third stop along, a young, blonde haired
woman took the seat in front of me.  I guessed she was either late teens or
early 20s.  Casually dressed.  A student perhaps?  Though why would she
still be around in August?

She unlocked her phone and started to phone someone.  "Hi Nat.  How's
things?"

Nat.  Interesting.  Probably a girl - Natalie.  But then again, could be a
boy - Nathan.  Friend?  Partner?  Sibling?  My brain began to whirr.

"Yeah, not bad.  Feel a bit rough after last night."

Okay.  Probably drinking.  Could have been drugs.  Although a good, hard
fucking could also be the cause.

"I know.  Really shouldn't have done those flaming sambucas."  She laughed.

Definitely the drink then.  Probably at a bar rather than at a party, I
reckoned.

"So what happened with you and that guy who was chatting you up?"

Still no clearer.

"So did you two...?"

Right.  Sounds like Nat and this mystery man may have got it on.

"And did you do him as well?"

Nat definitely got lucky!

"Me?  Nah.  Gary tried, as usual."

So blondie was less lucky.

"Stayed over, yeah.  Kim was just getting up as I left."

Maybe it was a party then.

"I mean, I would have.  But I've got this bloody dissertation to finish."

Ah.  I was right.  She is a student.  Must be doing a masters though.

"Yeah, I'm sure she will.  Otherwise her landlord'll kill her!"

Sounds like they might have made a bit of a mess last night.

"Hey.  Did you hear about Lisa?"

Oooohhhh.  This sounds intriguing!

"She's pregnant."

Double ooohhhh.  Now this is why I listen in to people's conversations!

"Four months apparently."

This just got better, I thought to myself.

"Course she fucking doesn't.  D'ya know the number of guys she's been
with?"

Okay.  That was telling.

"Dunno.  But she'll need to make her mind up soon."

I guessed that Nat's question was something to do with whether Lisa was
keeping it or not.

"Right, okay... yeah, see you later."

And with that, the conversation came to an end.  I smiled to myself.  Who
needs EastEnders when you can get that sort of entertainment on a simple
bus ride.


***


My phone buzzed just as we approached my stop.  I'll check it when I get
off, I thought to myself.

After thanking the driver, I stepped onto the pavement and made my way
towards the office.  Pulling out my phone, I checked to see who the message
was from.  Dylan.  'Grrrr.  I want to take it off!' read the message.

'Sorry.  Can't.  I don't have the key anymore.' I replied, before pocketing
the device.

Just as I was heading through reception and towards the lift, my phone
pinged again.  'What?  Where is it?'  I joined the other passengers in the
lift, including several of my co-workers.

"Morning Andy," said John, a short, squat man who works in the same
department as myself.  "Not seen you for a few days.  You been away again?"

"With what they pay us here?  Nah.  Just had a few days off.  Catching up
with things, you know how it is."

"Just to warn you," he continued.  "The chief's on the warpath.  Apparently
sales haven't been too good over the first half of the month so she wants
us all to 'up our game'."

"Gee, great.  Just what I want to come back to.  She's bad enough when
things are going well."

"Tell me about it.  I mean, does she think we all ring people up and tell
them that they're far better off with their current energy provider and
definitely shouldn't switch to us."

I chuckled.  "Yeah.  That's obviously what she thinks."

The lift came to a halt and we both stepped out onto our floor.  After
checking our pigeon holes for any post (John's was empty, mine only
contained a leaflet from the Union), we looked up what station we were each
using today - I was on 15, John was over the other side of the department
on 42.  I strolled over to my terminal and logged on.  As I waited for the
system to boot up, I remembered I'd not replied to Dylan.  'Sorry.  That
would be telling.'


***


With my system now up and running, I began making calls to the names and
numbers on my screen.  I managed to convince a couple of people to switch
providers, but most weren't interested.  It was hardly surprising - people
generally aren't concerned about their heating bills in August.

Just after 11 o'clock I went to grab a coffee from the machine.  Just as I
was nestling back down at my station, I got another text from Dylan: 'Where
is it?  I've looked everywhere?  Do you have it?'  I smiled at myself,
sensing his frustration.

'No, I don't.  And make sure you don't leave a mess!' I replied.  I could
only imagine what detritus he'd already made as he searched through my
cupboards and draws trying to find the keys.


***


Five minutes later, I got another text.  'Tell me where it is!'

'Now, now.  Remember your manners.' I replied.

Seconds later, another message.  'Tell me where it is, please!'

'No.'  Message sent, I turned my phone on silent and shoved it in my bag.
If Dylan kept pestering me, I'd definitely not land any more sales.


***


Sat in the 'employee lounge', as it was pompously called, I tucked in to my
lunch.  As I did so, I checked my phone.  14 messages.  All from Dylan, and
getting increasingly desperate.  The last three were a simple '?'

I typed a reply.  'I'm not telling you.  I know you're frustrated but I'm
not changing my mind so stop texting me.  We'll talk later.  Make sure you
get to your gymnastics on time.  Andy xx'

The message may have been harsh, but I had my reasons for doing what I was
doing, and I'd explain them to him later.  For now, I needed to finish my
lunch and then have a productive afternoon of sales.


***


I left work at 4, having managed to rack up 6 sales during the afternoon.
Not bad going, I thought to myself as I headed towards the bus stop.

The bus ride was extremely tedious.  Shockingly no one within earshot was
chatting on their phone, so my entertainment was severely restricted.
Instead I settled for watching people out of the window, but nothing of
note was happening outside either.

After alighting the bus, I picked up my car and set off for the gymnastics
centre.  Time wise, I knew I'd be pushing it.  I had, obviously, considered
driving into work that morning, but my hatred for rush hour traffic and the
city centre one-way system convinced me otherwise.

As it was, and breaking the speed limit several times, I arrived at the
centre with 2 minutes to spare.  Hurriedly, I made my way to the practice
area.  Just as I was walking through the doors, I heard the head coach
boom, "right guys, good work again today.  See you all on Monday."

As I walked into the room, I spotted Dylan chatting with Noah.  They
appeared to be deep in conversation, although Dylan seemed a little
agitated.  I decided to wait for him rather than interrupting them.  Whilst
waiting, a girl around Dylan's age walked towards me.  She looked sort of
familiar.

"Hi Mr Brown," she said as she came nearer.

"Er, hi... Kate?" I answered, hesitantly.

"Yeah, it's Kate.  I know," she said, her hands out at her sides, "I've
changed a bit since Year 6."

Had she ever.  When I taught her, she was a mere slip of a girl: short,
slim, and with a mop of frizzy red hair.  But now?  Wow!  She was taller
than Dylan, her hair was a lot shorter (and straighter!) than it had been,
and she had a pair of very ample breasts.

"Er... yeah.  It's... good to see you again," I said, regaining my
composure.

"You too," she replied.  "So what brings you here?"

Oh shit!  I needed to think quickly.  Suddenly it dawned on me that Dylan
had told me she was in his gymnastics team when we were out in Bulgaria.  I
really should have seen this one coming!

"Er... well... the thing is..." I mumbled, playing for time.  "I've
been... tutoring Dylan.  And we've got a session this afternoon.  His mum
was busy, so she asked if I could pick him up on my way over."

Phew, I thought.  At least that's dealt with.

"So what are you tutoring him for?" she asked.

Or maybe not.  "Science," I replied.  "Biology mainly."

"Oh.  Cool.  Well, I best go.  My mum's over there with my brother.  I
better go."

As she walked away, I turned in the direction she was heading.  Stood just
as I remember - tall slim, shoulder length red hair - was Kate's mum.  Next
to her was a cute boy with scruffy, brown hair.  I'd never taught the lad,
but had often seen him around school.  He was two years younger than Kate
and Dylan, but he appeared to be ripening nicely.

Just as the trio were heading out of the door, Dylan came over, wearing his
customary gym uniform.  As I looked down, I spotted a distinctly pronounced
bulge in his tight blue shorts.

"Good afternoon Dylan," I said brightly.  "Ready to go?"

"Yeah, I suppose," he replied.  Although he was trying his best not to show
it in front of everyone else, I could tell he was annoyed with me.  We
walked to the car in silence.

"So how was practice?" I asked, as we strapped ourselves in.

"Crap," he shot back, glaring at me.  "And it's all your fault."

I turned on the engine and set off.  "Look, I'd have been there to watch
you if I could, but I do have to work."

"Don't get so full of yourself," he snapped.  "I'm quite used to not having
someone there to watch me.  That wasn't the problem.  This is!"  He pointed
down towards his crotch.

"Oh.  That."

"Yes, that.  Do you know how bloody frustrating it's been, caged up all
day.  It's all I've been able to think about.  I'm a horny thirteen year
old boy, for fucks sake!  It's killing me.  Things just keep popping in to
my head.  You.  Friends from school.  Guys off TV.  And I can feel myself
getting hard, but then this thing, this fucking thing, stops it.  Grrrrr!
And then to top it all off, it's caused this huge lump in my shorts.  And
I'm sure the others were looking at me.  Noah definitely did.  That's what
he was talking to me about at the end.  He asked me who was giving me a
hard-on.  It's driving me insane!  Just get it off me.  Please Andy.  Let
me take it off."

"Dylan," I said calmly.  "Why do you think I'm doing this?"

"How the hell should I know?  Maybe you've fallen out with me!  Maybe you
hate me!  Maybe, now that you've had your wicked way with me, you've
decided to be a complete fuckwit!"

"Really?  Is that what you really think about me?"

"Yes," he snarled.

"Really?" I asked again, placing my hand on his thigh and stroking it.

"Maybe," he muttered.

I continued to rub his leg, working my way up until I got to the hem of his
shorts.  "Really?"

He looked conflicted.  "No.  I suppose not."

"So why do you think I'm doing it?"

Dylan shrugged.

"Okay, let me ask you something else," I said.  "Have you ever heard of
something called delayed gratification?"

"No."

"Okay.  So delayed gratification is when you resist the temptation for an
immediate reward, and instead wait for a later reward.  Now for a person to
do this, they need patience, self-control and willpower.  You with me so
far?"

"I guess so," Dylan answered.  "Though I don't see what that's got to do
with this."

"Remind me, how often do you jerk off?"

"Two, maybe three times a day.  Why?"

"Each time you jerk off, you have an orgasm, right?"

"Well duh!"  He looked at me incredulously.

"And each time you have an orgasm, you shoot.  And normally you shoot,
what... three, maybe four spurts?"

"Yeah, I suppose.  But I still don't..."

"Now tell me," I said, cutting him off.  "When you have your third wank of
the day, is there as much cum as there is in the first one?"

"I dunno.  Not usually."

"And this is exactly my point.  So what do you think would happen if you
were only jerked off once a day?"

"I'd cum more?" he suggested.

"Yes.  And what if you didn't jerk off for three days?"

"I think I might explode," he chuckled.

I joined in.  "Well, yeah.  But actually when you did cum, it would be like
an explosion!  That's exactly what I was meaning about delayed
gratification.  If you can resist the temptation of wanting to cum, and not
have the reward on the first day, but instead you delay it, then you'll get
a greater reward later.  You'll cum more and it'll probably feel even
better."

"Okay.  I guess I understand that.  But why the cage thing?  Why didn't you
just tell me not to wank for a few days?"

"Ah.  Do you remember what I said earlier about what someone needs to do
this?"

"Something about patience?" he speculated.

"And self-control and willpower," I added.  "Would you say you have all
those things?"

"Maybe," he said, a little defensively.

"Honestly?  Do you really think you have the self-control to stop yourself
from wanking for several days?"

Dylan paused a second, taking time to think about my question.  "Probably
not."

"Of course not," I said, once again stroking his thigh.  "You're a teenage
boy.  You're horny all the time.  There's no way you could stop yourself
doing it.  Heck, I'm not sure I could even at my age, and especially not
with you in my house.  So that's why I put the cage on.  I'm not being
cruel or nasty.  But I do want you to feel what it's like to blow your load
when you've not been able to for a while.  It'll be awesome, trust me."

"So you're just gonna keep it on me for a couple of days?  Then you'll let
me shoot?"

"More than just a couple."

"What, three?"  I shook my head.  "Four?"  I nodded.  "Four days?!  Four
whole days?!  Why?  Why can't it come off after like, two days?  Three
even?  Why does it need to be four?  What difference will it make?"

"Not much," I replied.  "But it'll probably take that long to get the keys
back."

"Back?  What d'ya mean, back?"

"Well, I've sent them somewhere."

"What?  Where?"

"To my uncle.  He lives in Scotland.  I posted them this morning."  Dylan
looked agog.  "They'll arrive back here on Monday, hopefully."

"Fucking hell," Dylan sighed.  "I've not really got much choice then, have
I?"

"No.  But remember what I said: it'll be awesome, trust me."  He looked at
me.  His face was unreadable.

We fell into an easy silence the rest of the way home, Dylan pondering what
I'd said.


***


Once back at home, I instructed Dylan to go grab a shower whilst I made a
start on dinner.  It was another sultry evening so I decided we would have
a BBQ.  As Dylan headed upstairs, I grabbed a bag of charcoal and a box of
matches, and made my way out to the patio.  Once the BBQ was lit, I put
some new potatoes on to boil, marinated some lamb chops, and prepared a
simple green salad.

I went back outside to check if the coals were ready.  Discovering that
they weren't, and knowing that Dylan would be ravenous after his
gymnastics, I put some bread in the toaster.  Moments later Dylan came
down, clad in a white t-shirt with rainbow striped sleeves, and a pair of
blue and white patterned board shorts.

"Is dinner ready yet?" he pined.

"No.  Still waiting for the coals to heat up.  But I've put some toast on."

"Good.  Because..."

"...I'm starving!" I mimicked, finishing his sentence for him.

"Yeah, yeah, very funny," he grinned.  I pulled him into a hug and kissed
his forehead.


***


End of chapter 15.  How will Dylan cope over the next few days?  What
should Andy do to help Dylan build up to his epic release?

As always, feedback is greatly appreciated - andybrown2000@outlook.com