Date: Sun, 31 Mar 2019 19:27:24 +0000
From: Stu Hadley <stuhadley77@gmail.com>
Subject: First Hand School Chapter 6

Day 6. A new experience

Themes include fucking, double penetration, exhibitionism, bondage, butt
plugs, dildos and domination. Average reading time: 20 minutes.

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every contribution is welcome. Thank you.

------

Fucking hell. Words fail me. I'm honestly not sure that I can do true
justice to what happened yesterday after seeing Trent... I know that I came
to the School as a complete sexual novice (and I know I've experienced a
hell of a lot in a very short amount of time) but even so I could never
have dreamt that sex could be as hot as last night.

So after the session with Trent I came back to the room, got undressed,
unlocked and wrote my diary. Jay then told me it was exercise time. I don't
know why but I was expecting he'd have a private gym off his rooms, but no,
apparently we were going to go to the School's public facilities.

I was a bit nervous about this if I'm honest... I know that almost the entire
school has seen me on stage, but somehow doing such a mundane activity -
weight training - really bought it home that I'm being held against my will
in a captive environment.

Of course, there was nothing really normal about the situation. Carl wanted
me to wear my powder blue `BOBBY KUNT' tank top and nothing else!
Seriously, no jock, no cock cage, no tan shorts. Fucking nothing. I
protested but he made it very clear that I didn't have a choice and that
loads of other guys at the gym would be tackle out so I shouldn't take it
personally. If anything I should be glad of the freedom of having my dick
uncaged outside of his room. I guess so.

The gym itself was fucking massive and insanely well equipped. Carl started
me on circuit training that completely demolished me. My first time
exercising with him and it was almost impossible to keep up. He said that
the program wasn't just aiming to craft my cunt but my body as well. Dear
god. What made it tougher was the sheer volume of hot men exercising
alongside us. It didn't matter where I looked, the gym was full of guys in
different states of undress - some tutors like Jay, some obviously pupils
like me. Except they weren't like me. Yes, some were naked from the waist
down and others were wearing a jock or shorts (lucky bastards!) but it was
more that every pupil had a different t-shirt on... Over there was a hot
black guy with a cute bubble butt. His tank was powder blue too but his
said `JIMMY the HOLE' on it. And there was a young and hairy middle Eastern
boy walk with `KOCKSUCKER KARIO' emblazoned on his sandy orange coloured
top. The degrading names and boys kept on coming. However, it was one
particular lad I saw only once - walking bowlegged and who could barely sit
down on any of the machinery - that I felt really sorry for. His red tee
said in gold letters `MALCOLM MANHOLE'. Jesus! My mind boggled.

All the while Carl and I exercised harder and harder, drips of sweat
running down our bodies. He was wearing a more regular gym top and loose
high-cut track shorts that revealed everything. I'm pretty sure he was
trying to keep me lusting for his dick, as his cockhead sure did keep
falling out of the leg holes a lot.

The combination of the other tutors, Jay's close proximity, the smell of
his sweat, his cock nearly always on full view (somehow just seeing the tip
of his fat dick was fantastically erotic) and the other guys around me was
intoxicating. Jay had told me I wasn't expected to stay erect - in fact
with all the exercise the blood should be pumping to other parts of the
body - but I couldn't help myself. I was so turned on. Even then I could
feel myself being embarrassed by my dick - Christ, I was leaking precum
everywhere!

As we continued our circuit we moved on to some mats to do some punishing
burpees, my least favourite exercise. I was so engrossed (and exhausted) by
the hard work that I failed to notice that the man working out next to us
was Carl. Carl!

Even though the last time I had seen him I had been massively humiliated
and covered in piss - somewhat at his instigation I thought - I couldn't
help but feel excited. I wanted to get closer, to smell his musk and see
the sweat rolling down his muscles. I couldn't help myself, if anything my
dick started leaking even more.

Jay kept me focused on those damn burpees though, putting me through my
paces. He seemed determined to completely exhaust me... and when Carl finally
decided to come over to us I could barely speak, I was that tired. He was
dressed in long grey sweat shorts with FHS on one side and a dark, closely
fitted navy t-shirt. You could see the trail of sweat soaking through his
clothes, especially around his crotch and ass. He looked stunning.

Carl nodded at me but directed of all his attention at Jay, asking how my
training was progressing. Jay replied that I had my first day with Trent
and things had seemed to start off on the right foot. Carl then asked about
my CiS scans.

"Hmm, could be better if I'm honest" said Jay. "I think this little one
could be cursed with an elastic sphincter that is going to keep on snapping
back no matter how wide we stretch him." What the fuck? I was there when
Trent showed my hole images to Jay. Snapped back? I was fucking gaping!

"Yeah, that could be a problem..." Carl replied. "I can't help but think
we're doing young Bobby a pretty big favour here. I mean he seemed to find
my cherrybuster pretty hard going. I reckon that if we weren't taking
direct action it could take him hundreds of punishing fucks before he'd get
truly comfortable with dicks my size. He's lucky he's here!"

Jay nodded as I looked on in disbelief. He suggestively grabbed his crotch
and then asked Carl whether `he wanted to give the young cunt a bit of a
kick-start?' Carl didn't hesitate for a moment. "Sure thing! I'd love to
tap Bobby's hole again" he answered.

Fuck, they were going to tag team my hole, right here in the gym? Even
though part of me couldn't resist the idea of being fucked again by Carl,
the larger part of me couldn't believe it. I cried out "please guys,
please... my hole simply can't take it! I've only just finished with Trent,
my ass has never been so tender--"

"Bullshit!" interrupted Jay. "Your hole may be tender, but I bet you're
hungry for dick, you little slut. In fact, I bet the more you think about
it the more you realise your twat is feeling empty and incomplete, like it
needs to be filled? Right?"

He could see the confusion in my eyes. Now he said it, it did feel empty...
The feeling of the phantom dong filling my hole from Trent's session had
slowly disappeared and now I was wondering what was next...

Both men took advantage of the moment. An unspoken language passed between
them as they seemed to know exactly what to do. They walked me over to a
weight bench and then both of them pulled their shorts down and threw them
aside. The thickness of Jay's fireplug dick still intimidated me, but to be
honest it was Carl's that really surprised me. Had I really let something
that big inside of me? It was fucking huge.

Carl sat halfway down the weight bench, his legs facing away from the
barbell. He then leaned backwards as if he were about to lift, but no
weightlifter had ever sat down with 11" of prick meat proudly rising from
their naked crotch.

Jay told me to straddle Carl's chest back to front, like I was about to do
a reverse cowboy fuck (something I'd learnt from the 24/7 porn in my room).
I didn't hesitate - sure, I could ride Carls' cock from behind. It was
exceptionally fat and long, but I wanted it...

However, it was then that Jay joined us and sat on the empty end of the
weight bench. Suddenly things got very crowded. I was squatting over Carl's
cock and he was facing my back. Seconds later Jay had leaned back onto the
bench so his slightly shorter fireplug cock was standing up from his sweaty
groin too. He inched his body closer to Carl's and in moments their dicks
were touching...

It was then that I worked out just what the fuck was about to happen! Carl
reached around with one hand to line up both dicks... I tried to climb off
but Jay grabbed me under my arms to secure me. In a stunning show of
strength he lifted me a few inches in the air and positioned me perfectly
over the tower of dick.

Carl's other hand quickly reached up to spread my hole as wide as possible
with his finger tips, allowing Jay to lower my body down and literally feed
my pussy with double dick.

I begged and pleaded for them to stop, the combined girth of their massive
schlongs felt as if they were ripping me apart, but Jay kept on lowering
me. The tips of my toes then touched the ground and I precariously
balanced. It was agony - the entire weight of my body was impaled on the
tips of two giant dicks and my toes. My legs shook and I struggled to keep
my balance. I knew that both Carl and Jay's cock increased in girth down
their shafts, but there was no way that I could fit any more dick inside of
me, no way!

Carl and Jay weren't having any of it though. Now that they'd opened me up
with their cock tips they could use their hands for other purposes... From
either side each one put a hand on my shoulders and started firmly pushing
me down onto them. Fuck! With gravity and brute strength I was being forced
to impale myself on their thick cocks, inch by inch of double dickmeat
plunging up inside of me. The pain was extreme, but nothing stopped them
from their hole goal... An agonising eternity later it was achieved - I had
bottomed out, my hole spilt wide to unbelievable proportions.

It was at this point that I noticed the crowd of men that had gathered
around us. I had been so focused on my own personal pain then it was only
when they started hollering and cheering as I plummeted the full length of
both cock stalks down to the base that I noticed they were there. I have to
say that after the fuck train and the public exhibitionism on stage, being
watched was beginning to turn me on.

It was then that Jay told me to fuck myself on their enormous cocks. His
serious facial expression - looking directly into mine - and the crowd of
tutors and boys surrounding me compelled me to do it. I rose up slightly
and slowly, (ever so slowly!) and started riding their dicks.

I couldn't believe it. Despite how big they must have been and my pussy
clearly overstretched with dick, the sensations were amazing. It felt like
I was fucking myself on a tower of power, and that if I could do this I
could achieve anything in life. I wanted this, I needed this... I started
crying out in pleasure and pain as my strokes up and down got bigger.

Jay totally misunderstood the noises I was making though. Even though we
were facing each other, he chose to read my expression as grimaces of pain.
He tried to spur me on... "Take it bitch! You've taken rubber dicks this size
today, don't tell me that real mancock isn't good enough for you anymore!"

The perceived slight on himself and Carl seemed to offend him, even though
he had totally imagined it. The truth was far removed: I was having the
time of my life. I couldn't believe the stretch and the feeling of being
full... gently riding up and down their combined poles. This obviously wasn't
enough for Jay though as he signalled a couple of the tutors to come close.
Within seconds two burly guys had grabbed an arm and a leg each and had
yanked me nearly a foot off the ground. I say nearly a foot, how did I
know? I could still feel the tips of the double dick tower at the entrance
to my pussy.

It was then that the two tutors started brutally fucking me on Carl and
Jay's dicks. Up and down as if all I was was a living fleshlight for their
dicks. The pace got faster and faster (and the cheering from the crowd
louder and louder). The angle and the sensations in my hole were amazing,
despite the pain. My unlocked dick was rock hard and I really felt I was
going to shoot... however, before I got there Carl and Jay couldn't take
anymore and they both came with a roar, gushing cum up my arse, so much
that I could soon feel it leaking down the sides of their shafts and onto
their groins. I couldn't believe how close I'd come to cumming only for it
to be snatched away.

The two tutors lifted me high in the air, cum leaking out of my stretched
ass and precum dripping from my dick. They lowered me straight onto the
floor, like a crab. My head hung low, I felt both desperate and humiliated.
I knew the rules though, there was no way I was going to touch my dick
again to help me cum.

It was then that I saw and felt some very familiar fingers at the entrance
to my hole! I looked up. Carl was kneeling on the floor in front of me, one
arm outstretched, his fingers entering my pussy. My god, it felt so good!
And his fingers seemed to be sliding into me so deep! His fingers moved
faster, pounding the nubbin in my hole that was obviously my prostate!

It was amazing, in fact so good I can't begin to describe just how it felt.
Time seemed to stand still and yet before I knew it I was shooting my load
high in the air, the longest and most intense orgasm of my life, spraying
my cum over Carl's navy blue vest! And all from having my hole worked over.
Fuck!

It was then that the full enormity of the situation hit me. I had just
sprayed my junk over a tutor. There was bound to be a rule against that!
Carl saw the flicker of worry in my face and smiled, saying "don't worry
about it kid." He winked and stood up, looking around the room for
something.

He saw it. A tall lanky guy wearing a white tank top that had `JERRY
JIZZEATER' on it. Carl snapped his fingers at Jerry and then pointed
straight towards his chest. Within moments Jerry was licking the remnants
of my load off Carl's vest, leaving not a trace behind.

And so that's the story of my first double penetration. I never knew that
sex could be that way. I wanted it so badly, no matter how much I knew the
damage that such big cocks must have been doing to my insides. Christ, who
cares though, my hole is `elastic', right? I bet it's always going to snap
back.

I am worried slightly that I'm getting addicted to cock though. I mean, I
really wanted it in the gym. As we exercised it seemed as if all I could
see was cock in front of my face... it was all I could think of. Is this what
being a pussyboicunt means?

After the gym Jay let me sleep normally on the bed next to him, though I
was back in my cock cage so I couldn't touch myself. This morning was a bit
of a surprise as he didn't fuck me, just telling me to do some cardio
before writing this. In fact, I should be at a lesson with Trent now, but
Jay says that as important as my training is, cataloguing my progression
towards being a pussyboicunt is just as important, so here I am...

Anyway, I've finished now so it's onto my next lesson. The cardio made me
realise just how much of a beating my hole has taken over the last few days
(bike saddle anyone? ouch!). I'm not sure just how much more stretching my
poor hole can take.

Later. More toys, plugged

God, how things can change in 24 hours. Yesterday? Sexual nirvana. Today?
I'm fucked. Jay is furious with me and yet I haven't done anything wrong.
In fact, all I've done is do what I've been told to do with the body that I
have. After all, it's not my fault I've got an elastic hole. Why the fuck
should I be punished for my own biology? IT'S NOT MY FUCKING FAULT. I'm
being held responsible for something I can't possible be accountable for,
as if I'm personally to blame for my hole snapping back into shape. What's
worse, Jay seems determined to change the course of nature forever.

Fuck. I'm beginning to realise just how dramatic the consequences of my
time here is going to be.

So, my second lesson with Trent started okay. I was led to the classroom
and immediately restrained to the stirrups chair again. I told Trent that
he didn't need to restrain me, that I would have done it willingly, but he
said it was always best to take precautions. What?! Was he suddenly
expecting me to up sticks and rebel? To kick up a fight and try to escape?
I'm torn between loving every moment and regretting every moment of this
program. I'm literally in a sex prison.

This time looking around I could see a small platform next to the chair
where Trent had laid out a pre-selection of toys. I don't know whether he
was doing it to intentionally freak me out, but they were lined up in size
order, with the small toy I had chosen as my first at the beginning.
However, if I thought we had gone big yesterday I was truly mistaken as the
line of toys just kept on going. Fatter, fuller, more gnarly.

Trent picked up a comfortable sized toy (maybe halfway between my 8" toy
and the 13" toy I had maxed out on yesterday?) and started lubing it up. He
was just about to start the lesson when he took one look at my ass and said
"woah, someone's been busy!" He immediately returned the toy in his hand to
the tray and picked up a dildo much bigger. Out of the corner of my eye I
could see it was just a size just below yesterday's personal best.

He lubed the toy up and then started pressing it against my pussy. I wanted
to resist, I wanted to deny what they were inexorably doing to me, but I
couldn't fight it for long. The combination of Trent's firm grip, the
slippery lube and the damaged gates to my hole were simply too great. The
giant toy slid inside.

"Fucking hell dude! What happened to you yesterday? Did you get fucked by a
truck?! Your hole is a fucking tunnel this morning!" he asked with obvious
glee. All the while he was talking he was sliding the imitation cock in and
out of my hole, getting deeper with every stroke. For all that had happened
yesterday, and even though I knew the toy wasn't my personal best the
stretch and feeling of fullness still felt very real.

I told Trent what had happened last night. The gym session with Jay. The
double dicking with him and Carl. Being force-fucked on their double dicks
by some of the other tutors. The lust and shame that I had felt...

Trent wasn't having any of it though. "Shame? Jesus Christ, you should be
proud of how much your hole has opened up! Sure, your pussy seems to be
recovering some of its clutch but it's pretty clear that it's stretching
nicely too. Look down boy."

I did and was shocked to see that Trent had seamlessly swapped dildos and
was now fucking my hole with Thor, the 13.5" toy I had ended yesterday's
session on. Fuck. 5 minutes in the stirrups and I was already wide open.
Yesterday's double really had done some damage.

Trent told me how proud he was of me, that not many guys could take what I
was taking. (I guess that's why I had been selected as a pussyboicunt?
Maybe. I don't know... as I write this I'm feeling pretty confused about all
of this). Trent said at this stage of my pussy development that it was
important not to rush things too quick, not to overstretch: the focus of
today's lesson was all about making a resilient hole.

And so that's how the lesson went. The toys didn't seem to get that much
bigger than Thor, but the shape and texture did. Flared heads, gnarly
shafts, soft accommodating toys to super hard inflexible dildos that my
hole could barely accommodate. All the while - if he wasn't concentrating
on an increase in size - he was increasing the speed and tempo at which I
could take the toys. It amazed me that his arms had the strength to keep on
relentlessly attacking my hole.

Wait, that's not true... Mid afternoon, towards the end of the session, he
held up a huge flesh coloured toy and showed it to me. "This is Choad by Mr
Hankey... See the hyper realistic uncut head and then the thick veins running
down the shaft? You're going to feel them it all - it starts out thick and
then thick, thick and thicker - slowly widening down to the base to keep
the stretch going all the way."

By now I was getting pretty good at recognising what a toy was going to do
(and feel like) to my pussy and I knew this one was going to open me up
good. (Good? Fuck! I'm turning into a parody of myself. It's being
surrounded by all this porn 24/7... I'm being changed minute by minute. Get a
grip Bobby!)

What happened next truly surprised me though. Trent grabbed some kind of
leather harness from a rack by the door and stepped into it, securing it
around his waist. Seconds later I realised what it was... a dildo harness for
fucking! Trent had grabbed Choad and locked it to the leather panel
covering up his own sizeable bulge. The gigantic dildo that now stuck out
from his crotch looked both oddly realistic and yet unreal - no cock was
that big! However, after all the dick I had taken recently a part of me
couldn't help but get excited at the thought of being fucked by a prick
that big. Fuck? Was I turning into a size queen?!

Trent used a foot pedal to lower the height of my seat, taking it from the
height of his hands to be perfectly aligned with the height of his groin.
For the first time since coming into Trent's classroom I felt as if his
energy had changed. Up till now he had seemed... professional if that's the
word. Now he seemed manic and full of evil lust.

"Feel it fucker!" he cried out as he lined up the uncut dildo against my
slack pussy and rammed the full length of the toy home in one punishing
stroke. FUCK! It was both an amazing demonstration of his fuck power and a
terrifying display of just how big my pussy had come. I couldn't help but
cry out in shock and awe. (No, pain, it was pain. You cried out in pain...
didn't I? Or was I enjoying it? Did I want it? Did I want to get fucked by
that monster toy? I just don't know anymore...)

Trent continued his power fuck no matter how much I cried out. (Yeah okay,
I may have been urging him on and saying things like `fuck me harder, I
need that rubber dick in my pussy' but I didn't say it all that often... just
once or twice...) He seemed to be intently staring at the thick rubber dildo
sliding in and out of my hole, stretching me out and giving me a `damn fine
set of pussy lips' as he said. (I think he may have actually said "Fuck! I
can see your pussy lips grow as I fuck! You've got real potential boy!" Why
do people keep on saying things I don't understand?!")

Eventually the fuck came to a close. It had to. I was in my cock cage, the
stimulation on my prostate meaning I was leaking precum all the time. (Did
some of my pre leak down and end up being lube for my own dildo fucking? Oh
dear God.) Trent seemed to be superhuman but even he couldn't keep up the
fuck forever. For the first time in forever he withdrew the rubber dick
from my arse, exiting with a soft squelching sound.

All this time Trent's face had been pretty manic, but that was nothing
compared to the dirty leer that came over when it looked down at the
results of his dildo-work. He was evidently very happy with what he saw,
taking the opportunity to feel both my burgeoning pussy lips and the gaping
entrance to my hole. His fingers felt amazing, especially mixed with all
the lube covering my ass. Trent keep on murmuring phrases like `that is
sweet looking pussy' and surveying his hard work from every angle.

Eventually he took off the dildo harness and turned back to the chair
holding some rubber gloves and a large closed container. He told me just
how proud he was of what I achieved in such a short space of time, and just
how amazing my pussy looked. I felt a little bit flushed if I'm honest.
Trent was an experienced anal stretching therapist after all. He must have
done this to countless guys... for me to impress him was a pretty big deal.

It was then that he put a thin black latex glove on his right hand and
scooped a big dollop of cream from the jar. "Now this is going to tingle
Bobby..." he said as he massaged the thick unguent on, around and inside my
pussy. Fuck, it really did! I could feel my hole involuntarily contracting
and squeezing Trent's fingers. It felt good! "That's a good boy! This
tightening cream will help you recover tonight... It might shrink you down a
bit, but that will help your pussy be more robust for the next session.
It's all about developing that resilient pussy we talked about. A
pussyboicunt has got to have stamina!"

I think I'm slowly beginning to understand how all of this is fitting
together...The exposure to big cocks, pulling a train, making my hole bigger,
stamina... Nobody has actually given me a definition of what I'm going to be
though. Maybe some kind of service boy? Like a rent boy for groups maybe?
Trent wouldn't give me any more information, just leading me back to Jay's
room and locking me inside.

Jay wasn't there so I followed the rules and took my clothes off and
started flicking through the porn channels. About ten minutes later (and
halfway through one of Ben's special video diaries about his amazingly
detailed (and forced) cock lust), Jay burst into the room. He was clearly
pissed off.

"What's this I hear about the progress you've made with Trent?!" he asked
angrily.

"What do you mean?" I replied defensively. "Trent said I'd made really
excellent progress, that he was happy with what I'd achieved."

"Bullshit! That's not what I've heard! I'll be the judge of progress - bend
over and assume the position, bitch! It's pussy inspection time."

I had seen enough of the fetish porn on the TVs to know exactly what the
position was. I walked towards Jay, turned around and then bent my body
over to touch my toes, my ass pointing at him.

I can feel him peering, prodding and examining my hole. An agonising minute
of silence later I hear him say "You see, this is what exactly the kind of
bullshit I'm talking about... Your hole should be slack and sloppy by now,
but all I'm seeing and feeling is some serious pussy clutch! You're still
plainly an overtight bitch."

I thought that was a bit unfair. One moment I'm praised for being elastic,
the next for taking a giant toy like Choad. And surely Trent's tightening
cream had closed me up? I tried to explain it to Jay and he wasn't having
any of it, shutting me down immediately.

"Don't whine boy. Your pussy development simply isn't good enough and I'm
not nearly satisfied enough with your progress. We got timelines to keep!
Now normally I'd assign some additional training sessions for you - maybe
bunk you up with the black attendants for a few nights of double fuck train
duty - but I think I need to take more direct action... stay there boy."

With that he wandered off, leaving me bent over and my ass high. For all
the momentary excitement I had at the thought of the black attendants, I
still don't understand what Jay is getting so worked up about. I had just
taken a gigantic toy and my hole was totally mashed up, what more could he
possibly want?

Jay came back to me and I quickly felt something pressing on my ass. It
felt round, like the apple shaped head of a big toy. I was wincing (Trent's
cream really seemed to have done the job!) but Jay couldn't see that and he
just kept on shoving. Eventually I can only describe my hole popping open
as whatever it was sunk into my pussy, a cry of shock from me, and then the
realisation that the thing in my ass was deeply flanged. Jay pulled the
object back and forth a bit but it felt secure in my hole, as if pulling it
out would require quite a bit of force. It was then that I felt a thick
leather belt being wrapped around my waist, and then my cock cage and the
thing inside of me being locked to the belt.

"That's it boy, stand up and let me talk to you" said Jay. I did as he
asked and that's when I became aware of the horrifying stretch in my hole.
Whatever was inside of me was made of a super firm rubber that was
painfully holding my hole open and preventing it from closing. Somehow this
was far worse than any of the dildos I had taken so far. It was firm and
unrelenting. There was no give, just a constant pressure that I was sure
was going to feel worse over time.

"I've just inserted a stretching plug in your pussy... yep, you heard me
right. Don't even think of trying to push it out or removing it - it's
locked in place and from now on it's only coming out when you're being
fucked or being trained.

Now a plug may seem like an old-fashioned approach to your dilemma, but I
think it's time to keep you permanently open. Normally we'd let nature take
its course and allow your pussy to take off some of the slack between
sessions, but after viewing your progress today I'm not going to let that
happen. In fact, we're going to reprogram nature. Give you a nice permanent
stretch..."

I can tell what you're thinking" -- really? can you Jay? because it sounds
like you're fucking me up for life -- "surely if my pussy is being trained
to be bigger then I'll need a bigger butt plug over time. You're damn
right!"

With that he opened a cupboard door in front of me and I saw a row of what
must have been twenty identical plugs but in ever expanding sizes. I was
right about just how evil the shape of the toy was - a round head that
flared out wide before aggressively coming into a wide core - the part that
was holding my hole open now. I could already feel my hole twitching and
trying to eject the invader. I could tell it wasn't going to happen.

I tried reasoning with him, trying to explain that I was making good
progress, about Trent's special cream, that I was happy to be fucked every
night, anything but the evil plug inside of me...

Jay was having any of it. "You don't get a choice in this boy. Maybe this
is the push you need to realise just how big we're going to make your hole!
There's plenty more plugs to go before you hit the end of the line." And he
was right. There was a gap six plugs in - obviously the one I had inside of
me now. Christ, there were thirteen more to go and the one at the end was
so big just looking at it made my eyes water.

He could obviously see the shock and horror in my face but he laughed all
the same. "I'm going to take great pleasure in stretching you out and
turning you into a fully functioning cunt. We're going to remake you to
take anything and everything..." he leered.

"Don't worry though, it's not all old-fashioned brutality though... that's
actually a very high-tech piece of equipment in your ass. Of course it's
got the cunt imaging system installed inside of it - in fact, it's scanning
your ass right now. But that isn't it, oh no. There's also a bunch of
elasticity sensors in the core that's measuring your clutch. If it detects
your clutch is weakening and your hole has got looser it will send out a
signal that it's time for an upgrade! Cool, eh?!"

Jay looked so fucking pleased with himself, whereas I just felt like I was
wilting away. There I was, naked in front of him, and both my dick and hole
locked up.

"Bit of an upgrade for you eh? That reminds me..." he reached behind him to
grab a one of my standard t-shirts that I hadn't noticed lying on the side.
"New uniform for you too..."

And that's how I ended up wearing a powder blue tank top with `BOBBY LOCKED
KUNT' in big gold letters on it to the gym. And how my entire body ached
from the muscle pain of yesterday's gym session combined with the world's
most evil butt plug in my ass.

Bedtime

So the gym was horrific. I felt as if all eyes were on me and yet everyone
was avoiding my eye. Thankfully Carl wasn't around so he didn't get to see
me in my new uniform. Not that it would be a surprise I'm sure... just
another number in a program.

Jay has disappeared and left me in the room writing this. I'm not sure what
the worse punishment is, my hole being stretched open or what he said to me
before he left?

It started off with us getting back to the room and me asking Jay whether
it was time for my nightly clean-out. It had been over 24 hours since my
last fuck and to be honest I was getting a little antsy for cock. I also
thought it would be a good chance for my hole to rest for a bit, even if it
did come with a punishing fuck attached. I asked whether he could unlock my
hole to let me douche.

"No boy, a permanent stretch is a permanent stretch!" he said. With this he
lead me to the bathroom and reached down between my legs. He seemed to be
manipulating the plug somehow as I could feel it moving around slightly in
my hole. Seconds later he held something narrow and cylindrical in front of
my face. "This is the internal centre of the plug in your ass. Oh don't
worry boy, it doesn't affect the structural integrity in any way - don't
think for a moment that removing this will let you clamp down and relieve
the stretch..." (He was right, I couldn't.)

"But what I can do now is attach this hose directly into your ass." He
laughed and bought the inch wide hose up to the plug, inserting it into the
hollow centre and then clipping some external ring over the joint. He
punched a couple of buttons on a control panel above where the hose ran
into the wall. Within seconds I could feel warm water flushing into my hole.

"See? This hose has two modes: pushing water into your asspussy and then
sucking the water and waste out to flush you clean. The machine will let
you know when you're done" he said. With that he left me alone in the
bathroom, locked to a hose automatically cleaning me out like I was
inhuman, nothing more than a hole to be played with. It was humiliating and
exhausting to keep up.

The machine beeped and Jay reappeared to de-hose me (I didn't dare myself).
I followed him back into the bedroom, fully expecting him to unlock my
clean ass so he could fuck me. He obviously saw the intent in my eyes. "Oh
no boy, you may be clean, but I'm going to let that plug work its magic and
hold off fucking you for a couple of days. You stay here and watch porn
whilst I go out and find some pre-slacked pussy to fuck. You're too damn
tight for me!"

With that he fucking left. What a fucking bastard. He gets me addicted to
cock, has my hole stretched to kingdom come and then holds it painfully
open, all the whilst depriving me of the one thing I came to this school in
the first place for: dick!

I was way too worked up to go to sleep, so I'm writing this. I'm worried
that I'm changing. Physically, yes - just how loose is my hole going to be?
- but mentally too. I said that I feel addicted to cock, but it's not just
that. The porn channels no longer seem so twisted, not so hardcore. It all
feels like a sickening part of my life, as if this is my new `normal'
reality. That's fucked up. Where is this all going?

Fuck it, I'm going to bed. Jay hasn't come back.

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Next: Bobby's training gets tough after a cum infraction...

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Comments and suggestions welcome at stuhadley77@gmail.com