Date: Fri, 24 Jan 2014 12:07:55 +0800
From: Matt Loh <matt.loh.83@gmail.com>
Subject: The Headmaster (scat)

 This story involves caning, spanking, breback anal sex and scat action.
Feedback and emails are welcome!
matt.loh.83@gmail.com

*The Headmaster*

  I stared at the door in front of my Headmaster's door, feeling a lump in
my throat. My heart was pounding in my chest, not knowing what to expect,
and my cock was rock hard by now, straining against the gym shorts that I
was wearing, in anticipation of what I hoped was to come....

  Thinking back on what led up to today, my mind drifted back to my younger
days; when I was in high school and in my early teens. Caning was a very
common occurrence in schools and homes here, and there were strict rules
for boys that we had to follow. Serious offences in school were punishable
by public canings, and these were commonplace. I remember clearly watching
the first public caning when I was 12 or 13 or so, being slightly in awe
and fearful, at the same time being strangely aroused. Watching a bigger
boy spread his legs and bend over, and crying out in pain as the strokes
landed deliberately, slowly and painfully on his barely protected buttocks
had a very dramatic effect on my groin and cock. I remember going off to
the toilet after and jerking off vigorously with the image of the boy and
the sound of the rattan cane on his buttocks fresh in my mind. Being that
young and horny, I blew not one, not two, but three loads over the toilet
seat till my cock was dry.

  I had gotten my first caning when I was 13 or 14. Back then, school
canings were all no-nonsense, serious affairs. I remember being marched
down to the Headmaster's office for an offence that I don't remember
anymore now. That same feeling was there again; the lump in my throat, the
pounding in my chest as I stood there in my shorts. The Headmaster's words
were a fuzz in my brain as I struggled between the fear and how
outrageously horned up I was. I was sure I was stiff as a rod in my shorts,
and it already started to hurt. Then all of a sudden, I was made to bend
over, over his large wooden desk. I spread my legs apart in a bid to give
my cock more room to expand, and pushed my bum out; it felt good, sticking
out like that. I remember him tapping my buttocks with the cane for aim,
and then the first loud swich and thwack. The sting and pain was
tremendous, it felt like my whole backside was on fire, I cried out once
but didn't straighten up, and I could literally feel the welt form, my
heartbeat throbbing along it. My hardon immediately vanished, but was not
slow to reappear as I squirmed against his desk. The caning was slow and
deliberate, as they often are, so the punished boy has time to think upon
his wrongdoings (or so they say) and for the full sting of the strokes to
set in. I was originally supposed to receive 6 strokes, but for
straightening up and rubbing my buttocks, I received 2 extras. This was
followed by corner time with my legs open and hands behind my head,
humiliating, but extremely arousing as both my cock and the welts on my
buttocks throbbed in unison.

  Following that first caning, I remember hurrying off to the toilet,
locking myself in one of the cubicles and stripping off my shorts, getting
naked waist down as my steel hard cock sprang free. I spread my legs wide
and squatted down, vigorously pumping my cock with my fist. I came within 2
strokes, blowing a huge load against the toilet bowl in front of me and
also onto the floor. I was still insanely horny even after, thankfully it
was after school hours by then, and I remained squatting there, my asshole
spasming as my orgasm came down, and I continued stroking my still hard
cock. I placed a finger from my other hand back against my own asshole,
which was by now lubed from the cum running down my asscrack. Opening my
legs wider, I pushed my finger deep in, feeling my cock twitch in pleasure
as I anally penetrated myself. Instinctively, I started fingering my
asshole, feeling how the penetration intensified the sensations as I jerked
off. I pulled my finger out intermittently as I fisted my cock, and ran it
along the fresh welts on my buttocks, feeling the warmth. I contiinued
jerking off furiously, cumming hard another 2 times before I grew tired and
my legs started to really ache. Not bothering to clean up the cum, I got
dressed and got home.

  Once home, in the privacy of my own room, I stripped off again after a
bath, and admired the thick red welts in the mirror, getting hard once
again. The welts were livid and thick, running nearly perfectly parellel
across my buttocks, even through my shorts, I could see that the
Headmaster's aim was nearly perfect, nearly placing all the strokes
directly on top of each other, maximising the sting and pain for the boy.
As I admired the welts, I stroked my rapidly hardening cock, which was by
now, aching quite a bit from the constant arousal.

  From them on, caning became quite an obsession. The internet was readily
available, and porn with caning, particularly on males, became an
addiction. After school, I would spend hours scouring the web and
downloading videos, keeping them stored away, masturbating while watching
them countless times over. It was quite mesmerising, watching teenage
looking guys to grown buff men taking canings. Some were quite severe, in
particular I remember watching one with a very buff bottom guy with a
shaved head bending over without restraints, taking a really severe caning
by an even more buff, bigger black guy. He trembled and moaned, and took in
excess of 100 strokes, getting and losing his erection a few times through
the caning. He was bleeding quite a bit by the end of it, but he looked far
from being spent yet. The black guy cleaned him up and the bottom quickly
spread open his asscheeks as his Dom jerked his cock to full hardness. I
had never seen a bigger cock than that, and I was extremely turned on, and
jerked myself off, as I watched the black man lube his cock up lightly,
then push his entire length up the bottom's asshole. The fucking was hard
and relentless. Without even touching his own cock, then bottom spewed a
load of cum, as the black guy kept up his fucking, only blowing his load
over the other guy's face after a further 10 minutes or so.

  In school, I was in a way, sometimes fixated on getting caned. Like
earlier mentioned, canings remained very commonplace even for minor
offences sometimes, and were dished out fairly liberally. For recalcitrant
offenders, expecially, the canings would get progressively more severe. I
would often find myself on the receiving end of canings, for offences done
on purpose, and without fail, was already extremely turned on. However,
canings in school were always no-nonsense affairs, and they were not
delivered bare bottomed, which I so craved after awhile, nowhere near as
explicit as what I would watch online and jerk off to, and fantasise about
having done on myself. Regardless, they were always quite severe, and the
Headmaster, after awhile I think, got rather annoyed at having to see me
repeatedly for punishments. He caned even harder and did not have any
qualms increasing the number of strokes or giving me extra through the
canings. Little did he know that after awhile, I guess I too developed a
higher tolerance for the pain and sting, and progressively, I could stay
aroused and hard throughout the whole caning without even losing my hardon.

  Near the end of high school, when I was about 16 or so, I remember
vividly one encounter with the Headmaster. I was just caned the day before,
a good number of strokes, and the welts were still very fresh. Working
myself up into a frenzy later at home with a good round of porn and
numerous jerking offs, I got into trouble again (on purpose) the day after
and was promptly marched back to the Headmaster's office. I could see he
was visibly annoyed at having to see me again so soon, and I was hard by
then. Bending over again, I opened my legs, my cock straining against my
shorts.

  He said in a business like tone, cane in hand, "Matt, I'm sick and tired
of having to deal with your nonsense, 24 strokes today."

  I gulped in anticipation, I had never received this many strokes before.
My cock throbbed as he lined up the cane against my buttocks. He stepped
back so he would have more room to swing the cane, tilting back slightly
then swinging his arm down hard, his first stroke showed me he really meant
business this time. The thwack was one of the loudest and the sting was
immense, upon my already welted buttocks, I started squirming immediately,
crying out once (rare on the first stroke since by then I was a very
seasoned recipient of canings). He gave time in between strokes for the
burning and pain to build up until it was at its climax, which he timed
perfectly, before he lay another vicious stroke down. The pain built up
immensely, but I guess the masochist and submissive in me got the better of
me. I was squirming in both immense pain and that same strange arousal as
well, my cock remained hard and strained, and I got extremely close to
cumming by the time he was at 15 strokes.

  I kept my legs apart, they were quivering somewhat, both in pain and the
heightened arousal was in. My cock was still straining and it was starting
to hurt. I could feel the Headmaster rap my buttocks with the cane a few
times in warning for the next stroke.

  "Keep your buttocks out Matt," he said in a matter of fact voice.

  A loud swing, smack, and and excruciating sting followed almost
imemdiately. The stroke landed probably perfectly right over some of my
existing welts, really causing the pain to reach a peak. Coupled my
extremely aoursed state, and my exposed, embarrassing position with my
buttocks stuck out, I came immediately in my shorts. I moaned and cried out
loudly, shuddering, my legs immediately turned to jelly and I thrust my
hips out a bit as my cock and asshole spasmed in unison as I came probably
with the hardest orgasm of my life. The Headmaster could probably not
differentiate it between the reaction from a boy in a lot of pain, but I
was cumming harder than I could ever imagine. I could feel the cum flood my
undies and I'm sure a big wet spot formed immediately on my shorts.

  My legs continued trembling as the Headmaster paused in between strokes.
Meanwhile I was trying to ride out my orgasm, as I was sure I pumped a
gallon of spunk in my shorts. My orgasm slowly came down, and so did my
hardon. I was still breathing heavy but the intense orgasm took to edge off
my horniness.

  "I don't want to tell you again Matt, buttocks out, legs apart." the
Headmaster's voice boomed from behind.

  The cane came up again and the sting from the next stroke was a million
times worse now that I had cum. I immediately straightened up and cried
out, reaching behind and clutching my buttocks with both hands. The
Headmaster did not say anything till I bent over again, clutching the edge
of his table.

  "That just earned you another 2 strokes, I advise you to stay bent over
until I tell you to straighten up. Now buttocks out," he said again.

  There were 8 or 9 strokes to follow, each of which were pure agony. I was
quivering in fear as each one passed, my legs were jelly, and my buttocks
were on fire. The pleasure and arousal had completely gone now and my
knuckles were white from gripping the table edge so hard and also from
sheer terror. I was sobbing slightly now, deeply regretting getting into
this situation, as the sting of each stroke brought my attention back to my
badly bruised and welted buttocks.

  I breathed heavily as I rode out the pain from the last stroke. I stayed
bent over, not daring to move till I was told to do so. I could feel the
cum running down the inside of my thighs now, hoping that the Headmaster
would not notice.

  "Now straighten up and get out of my office Matt," the Headmaster said in
a stern voice behind me.

  Not daring to turn around immediately lest he noticed the big wet patch
in front of my shorts, I waited till he had moved to return his cane to the
cabinet before I straightened up and walked quickly towards the door. I
left his office and quickly made my way to the toilet. I was lucky it was
already after class hours and there weren't many teachers or students
around. I managed to get to the toilet without any incident and quickly
locked the door behind me. Stripping off my shorts and undies quickly, I
stood with my buttocks facing the mirror and turned around. I was slightly
aghast at what I saw. The caning was surely the most severe I had up till
this point, and coupled with yesterday's, had left my entire buttocks
covered with livid welts. I had already started to bleed a bit from at
least 5 to 6 different areas. Looking at the inside of my shorts, I was
filled with a large pool of cum, it was a bit of a mess. The entire
situation started to arouse the horniness in me again. I felt my cock
quickly rise, imagining bending over again for the Headmaster, and
submitting my buttocks to another good caning with a raging hardon.
Stroking myself off again, I spread my legs apart, as I admired the angry
red welts, and slipped a finger that I had dipped in my own cum, right up
my tight asshole. My cock twitched in my fist as I felt my finger go in and
I moaned a bit in pleasure. I couldn't squat as I normally liked to do when
I masturbated and fingered my ass (squatting always really opens my hole
up), because I wanted a good view of the welts as I jerked off. So I
remained standing as I bent my knees slightly so my finger could get in
deeper. Then started thrusting hard and jerking off feverishly till I
spunked hard and satisfyingly again, all over the floor.

  Following that day, I grew a bit frustrated. I still throughly enjoyed
the deeply erotic feelings from a school caning, but I yearned for the
absolute nastiness and outright kink that I watched on my regular daily
porn sessions. I guess there was always that slut in me. Canings in school
were always pretty no-nonsense and delivered on a covered ass. This always
left me intensely horny after, and to my own devices to finish myself off
with a good wank in private after. I then started joining porn sites with
gay / bi guys who were into kink and caning or spanking, and visited chat
channels with a similar profile of guys. In my area, well, as I have
mentioned before, caning is pretty common, both in schools and at home. And
as a direct result, I think, it turns out that there are many (if not a
whole lot) of guys that are into this exact kind of kink. It was easy
finding guys who were into caning. I started with chatting and exchanging
emails, and it wasn't long before I plucked up the courage to meet one.

  I remember the first time meeting some random guy off the net to be
caned. I felt the same way as I did during canings, the excitement and
anticipation in my chest. He claimed to be an experienced older guy and he
had delivered numerous canings to other subs. I made it clear what I wanted
and that I wanted to be fucked, or basically, do whatever he wanted
sexually. I met him at his own home, and he opened the door bare chested,
with a long, medium thickness cane in his hand. He was a pretty big guy,
and I could see that he liked what he saw.I was pretty active in sports in
school, I swam, did gym and basically was pretty fit and had a bit of a
tan. The sports and workouts basically kept my testosterone levels pretty
high all the time I think, and kept me constantly horny. My buttocks were
definitely a good target I thought, not flabby at all, but definitely a
good, pert, toned set.

  He groped a bit at my buttocks and I did not object at all, standing
still for him. I got horny quickly and started getting a raging hard on,
and so did he, judging by how he tented his shorts. We didn't speak much
but knew what each other wanted. I quickly stripped off my shorts. I was
wearing a feminine slutty yellow thong as he had wanted, and it was quickly
shucked off, my cock springing free immediately. I was already rock hard,
as I removed my shirt, now totally naked. Wordlessly, I walked into the
living room and bent over his sofa fully. I pressed my chest down against
the seat of the sofa, keeping my stomach down low and this had the effect
of really sticking my buttocks out for him. I'm sure it was quite a sight.
I had "saved up" for him, also at his request. Meaning that I hadn't gotten
a caning in at least 2 weeks now and had not masturbated for an equally
long time. As a result, you can imagine I was pretty darn horny and needing
release now. He picked up the thong from the floor and brought it up to my
mouth. I knew what he wanted and opened my mouth as he gagged me with my
own slutty thong, keeping my position. I could hear him remove his own
shorts and could imagine he was jerking off now. I spread my legs apart
now, and bent my knees slightly, feeling my asscheeks start to pull open
and expose my asshole to him. This was really getting me hot now.

  I couldn't take it anymore, and reached into my mouth, ungagging myself
for a short while, my cock still throbbing.

  I looked back at him, my eyes glazed with pure lust . "You like this
position? Want me to spread a bit wider for you? I want you to cane my
buttocks as hard as you can, any number of strokes till you are satisfied,"
I pleaded.

  "Fuck, that's hot. Yes, open up some more for me," he replied, stroking
his cock.

  I spread even wider for him, keeping my buttocks as high up and out for
him as possible. My asshole seemed to twitch as I readied myself for him. I
put the thong gag back in my mouth and waited in anticipation.

  He didn't waste much time as he lined the cane up, pulled his arm back
and took a good swing. The cane landed squarely across my bared buttocks
with a sharp thwack. This was the first stroke I received on my bare
buttocks and the sting was much more pronounced. It was much more painful
but I had been on the receiving end numerous times and I had no problem
with maintaining position. The intense sexual energy of the entire
situation, the fact that I was naked, my legs apart and in such a lewd
position, getting a stinging caning on my bared buttocks by a hot muscular
guy, and the fact that I was starved of a caning and a good wank for the
past 2 weeks made me mad and absolutely pent up with pure horniness. I
practically moaned in pleasure through the gag as I felt the sting in my
buttocks start to build up. Opening up my legs even wider, I made sure he
got a good view of my shithole, and my muscular toned thighs strained a
bit, I kept my chest pushed down into his sofa so my buttocks remained way
up and out to give him a good target.

  He groped my right asscheek after the first stroke, feeling the warmth
his first stroke generated. His pulled my asscheek hard to the side,
exposing my hole further and making me even harder, and I felt his thumb
press right up against my tight shitter. I bet he could feel it twitch.

  He moved back again and followed up with an equally vicious swipe with
his cane upon my unprotected buttocks. I could literally feel the welts
start to form now, and I was rightly impressed with his accuracy and skill
as a caner as the strokes were really painful and stinging. He took his
time, like the school Headmaster does. probably enjoying the view in
between strokes and masturbating himself. I moaned into the thong gag in my
mouth, which was probably soaked by now from my drool. I counted the
strokes in my head, keeping still and making sure my position was
satisfactory, spread open, like a slut. When he got to 12 strokes he walked
back up to me, cane still in hand, as my buttocks pretty much trembled. I
was definitely in a lot of pain, my backside felt like it was on fire, and
I was still horny as fuck, my cock was throbbing and harder than ever
before. He reached into my mouth and pulled out the gag, leaving me free to
talk and moan out loud now. I knew what he wanted me to do without even him
asking.

  I turned my head to the side so I could look back at him as he stood
behind me. "Cane me harder, please, more, give me another 24 at least," I
pleaded and begged him. I was literally drooling in lust

  He smirked at me as he stroked his own cock, and I could see that he was
definitely fully hard by now. I kept my buttocks out high as he raised the
cane again. The strokes came steadily, the pace very much controlled by
him. I continued moaning loudly with each stroke. Though the pain was
immense, I felt immeasurably pleasured and aroused, and I remained fully
hard throughout.

  "17 sir, thank you Sir," I would moan. Each stroke would be clearly
counted.

  "Harder Sir, I want to learn my lesson well Sir," I would beg and plead
in between strokes. I could tell that he was turned on by me asking for
harder strokes and he did his best by progressively taking harder swipes
with the cane.

  "Keep your legs wide apart and your buttocks out boy, make sure you keep
that hole open," he said as he tapped my buttocks with his cane.

  I wasn't sure I could hold out much longer, being in a constant state of
arousal. My cock was throbbing and my balls were aching to bust a load. My
buttocks were, I'm sure, properly welted up by then and he was standing
behind me with his caning arm drawn back. He swung foward forcefully with
really good aim and landed perfectly squarely over the centre of my
buttocks over a series of other welts, and the sting pushed me over the
edge.

  "Oh fuck, I'm cumming!" I yelled out. My cock spasmed and so did my
asshole as I erupted in a huge orgasm. I blew thick ropes of cum over my
own stomach, all over the sofa and on the floor as I shuddered hard. I
struggled to keep my position as I involuntarily thrust my hips forward a
bit, my cock cumming without even being touched. I tried to keep my legs
wide apart as I orgasmed, so he could get a view of my spasming asshole. My
thighs were starting to wobble from the sheer force of the orgasm and I
gripped onto the sofa.

  "Fuck, that's hot boy. You never told me you could cum from being caned,"
he said lustily behind me.

  I continued cumming for what seemed to be at least a minute, my chest
heaving and my eyes closed, until I started to cool down somewhat as I rode
off the remaining of my orgasm. He stook behind me, continuing to jerk off,
till I bent over and pulled me by the hair.

  "Fuckkk, I'm cumming too," he growled. "Open that mouth, I'm going to cum
on your face"

  He yanked my head up slightly by the hair as I opened my mouth, closing
my eyes. He quickly erupted in his own orgasm and I could feel the warm cum
splatter over my face and into my mouth. He came a really huge load and I
was sure it made a hell of a mess over my face, till he finally stopped and
let go of my hair.

  Wordlessly, he walked back to where he was standing and picked up his
cane again.

  "Now, I don't think I even gave you permission to cum, and you've really
dirtied my sofa and my floor," he said matter of factly. "Keep your
buttocks out, open up your legs, you're getting another 24"

  I was still recovering a bit from my orgasm, but was aware enough to know
what was coming up. Though spent, and having most of the edge of my
horniness taken off after that huge cum, I was still ready for more. I
already felt my cock getting hard again at the thought of getting even more
strokes of the cane from this hot caner. I pushed my chest and stomach down
low again, presenting my buttocks lewdly to my caner and kept my legs
spread wide open, bracing myself.

  "Cane me, harder...." I could barely mouth the words, heavy with lust.

  He was as good as his word, and he resumed the caning. The first few
strokes directly after my orgasm were truly agonising, as I felt a trickle
of blood now. The sting was incredible but it didn't take long for me to
really get super horny again. I wanted even more, and he delivered. I
moaned into the sofa like a bitch in heat as he slowly took his time,
giving my buttocks probably the heaviest punishment I'd ever experienced up
till then. Each smack from the cane rang out loudly through the room, even
louder than my cries and moans.

  He reached 24 eventually, finally putting down his cane. I was insanely
aroused again by then, again very close to cumming, my asshole, cock and
balls throbbing in unison as I breathed hard from the pain and arousal. He
was probably as steel hard as I was and quickly came up behind me and
squeezed one of my severely welted buttcheeks. I held still as he groped
me, then heard and felt him spit squarely on my asshole. His saliva ran
down my asscrack and over my asshole, and he ran 2 of his fingers down as
well, rubbing his spit around my tight, as of then virginal fuckhole. I
knew naturally what he wanted, and reached back with both hands and held on
to each asscheek. I could feel the welts and the intense heat from my
buttocks as I held onto them and stretched them apart as wide as I could,
giving him full access to my shithole. I obediently flexed and pouted my
hole open to show him I wanted him inside me. He pushed both his fingers in
firmly and I opened up easily for him, taking both fingers knucke deep. I
moaned loudly as his fingers brushed and pressed against my prostate. He
knew how close I was to the edge from how hard I was panting. He thrust his
fingers in and out in a rough anal fingerfuck and I did my best to loosen
up, as my asshole had tightened up quite a bit from the stinging caning.

  It didn't take very much at all. Within 10 strokes of his fingers or so,
I felt my cock spasm and jerk again as I bit my lip and came like a
firehose. I moaned out loudly and told him I was cumming again, for the
second time, without even touching my cock. I spewed a huge load of cum,
dirtying his sofa even more as my asshole spasmed hard around his fingers.
He continued roughly and firmly fingerfucking my asshole, not even
bothering to give me a reacharound because he knew I didn't even need one.

  He roughly stretched my asshole open with his fingers as I continued
oragasming, before abruptly pulling out as my cock was still spasming. I
was overcome by the strength of the orgasm and kept my legs open and
squatted down to ride it out. I could literally feel how my asshole was
contracting in time with my spurts as well and I reached down to pump my
cock for a few strokes with my hand.

  He pulled me up by the hair and pushed me roughly onto the sofa as I was
trying to pump the last few drops of cum out my cock. I lay back, knowing
what was going to come now. I was in quite a mess, drying cum over my face
and hair from his earlier load and a fresh load I spewed on my own stomach.
I could also feel the warmth of my own cum I just spurted all over the sofa
against my back as I lay down. He cock was hard as he roughly yanked one of
my legs back and pushed it way back beside my ears. I am pretty flexible
from my exercise and sports so that was no problem for me. I used a free
hand to pull my other leg back and open wide as he pumped his own cock,
getting it ready. I was still hard, keeping my legs wide apart as he squat
down a bit and placed his cockhead at the entrance to my shithole. He
didn't bother with a condom and neither did I. He was at least a good thick
7 inches and he definitely was stretching my virginal asshole open. I
relaxed and flexed open my asshole as he pushed and he quickly popped his
head in, filling me up nicely.

  I quickly grew accustomed to the sensation and started jerking myself
off, keeping my other hand holding my legs apart. I moaned in pure lust as
he started pushing, and he was quickly buried in balls deep, officially
taking my anal virginity, using only his own spit for lube. I was in total
ecstacy by then, not knowing that getting my ass fucked could feel so good.

  He started thrusting quickly, turned out that he was a pretty good
assfucker as well as caner. He gave deep, solid thrusts that lodged his
entire cock up my ass with every stroke, and he would pull out till only
just his head was gripped by my sphincter before thrusting in hard again.
His cock rubbed up against my prostate and I knew that coupled with my
jacking off, I wouldn't last very long. The fucking was hard, wet and
really really good. He started leaning over me after awhile, using his
bodyweight and stretching my legs even wider apart with his hand, thrusting
his hips at the same time to try to get in deeper. From the way he was
breathing and sweating, I knew he was close too.

  "Oh fuck, I'm going to cum," he groaned out loud, keeping up a good and
fast pace of assfucking.

  I then felt him pause and tense up. He then used both hands to spread my
legs apart and pressed all the way down till both my thighs were pushed
down hard into the sofa and my ankles near my head. I felt like I was
speared into two, as he thrust his hips inwards and started shuddering. I
could hear his loud moan and could feel his large cock start to spasm and
shoot his big load directly in my shit tunnel. I could literally feel the
warm jets of cum along the insides of my shit chute.

  He panted a bit, his orgasm lasting at least a good long minutre, before
he finally pulled out his softening cock. I felt used, abused, and loved
every single second of it. It seemed like my randiness knew no bounds.

  It was pretty late by then, a Friday night I remember. Good thing there
wasn't any school the next day, and my parents were used to me staying out
late on Fridays. Little did they know their boy was being an anal slut for
this hunk. We stayed naked like that for a bit, but I felt horny again
almost immediately. I still hadn't released my thrid load. I stayed till
about 4am that day, not wearing an inch of clothing, and had anal sex at
least another 5 or 6 times, all bareback, and it seemed I just couldn't get
enough. I sucked him, rimmed him (my first time rimming someone), did ass
to mouth, and he had an equally insatiable appetite for sex. He came
another 3 or 4 times in my asshole, and had a couple more loads blown over
my face and mouth. He was nearly dry orgasming by that time. I came an
equal number of times at least and I knew that from then on I would be
hooked on nasty man to man sex.

  After that incident, I was totally addicted. The internet chat rooms and
hoopup sites served as a convenient portal to meet guys who had similar
interests, and as I had mentioned earlier, that is a lot of guys over here.
The new top I had hooked up with became a regular as well, since that first
encounter, as I knew he could deliver really stinging canings and a good
bareback buttfuck after. I started regularly meeting other tops for caning
and fuck sessions in random hotels, at their houses, and even ended up in a
few group fucks with other bottoms and tops present. It was like after I
started, I couldn't stop. I was pretty reckless as well, I hardly, in fact
never, even cared if the tops used rubbers at all. After a caning, all I
wanted to do was get fucked. I must have taken countless loads in my ass,
down my throat and wherever else on my body the top wanted to cum. There
are some guys who are top, some who are flex, but I was a totally and
completely a 100% bottom slut. I knew it deep down and I couldn't get
enough. I met guys very regularly and apart from getting caned at school I
would regularly get it from random guys off the net. Gradually it became a
weekly affair, sometimes even a few times a week. High school went by like
that over the next 2 years or so, I'm not exactly sure how many but I must
have met over 50 to 60 different guys for caning / sex sessions. I must say
the appeal of a fit, athletic teenager who is a total slut for the cane and
bareback fucking got me many tops who wanted to meet me again and again.
They would introduce other tops, and I sometimes didn't even need to look
for tops over the net, since I also repeatedly went back to those that I
found were really good caners or really good fucks. One thing that I really
wished for though, was that school canings could mirror what happened in my
private sex life. School canings remained very no-nonsense, pants on, and
it grew quite frustrating with my hardon always raging in my shorts. Though
the sexual canings I got from my tops satisfied me in a lot of ways, the
arousal and sexual energy I felt getting caned in school was really quite
different, and in many ways, even though the canings were very
business-like, the sexual tension I felt was always tremendous.

  I went on to college soon enough, and the caning culture there did
continue. though as young adults, corporal punishment was not dished out as
often. But when it was, it was really severe. Minor offences were not
dealth with by canings anymore like it was in high school, but offences
like cheating in an exam, smoking, fighting in school, were all still
punishable by caning, and very severely at that. The headmaster in my
college always had a stern look, and he had a reputation for being really
harsh as a caner. He was a white man, fairly tall and looked very buff for
a guy in his late 40s or 50s. He played squash and tennis a lot,
apparently, and this must have contributed to the ferocity of his cane
strokes. I was still fairly new in college and hadn't got caned by him yet,
though I had received a few canings from other teachers. They were fairly
severe and well delivered but I was very keen to experience one by the
headmaster himself. I had heard rumours that he was gay, but I thought it
was all just idle talk among the boys. Outside of school, I continued
hooking up with new tops and meeting up my old ones very regularly for
canings, if not just for sex. I started developing a taste for orgies and
group fucks and I especially enjoyed those where I was the only bottom guy
and there were 4 or 5 other tops just taking turns having their way with
me. I guess I just enjoyed being very submissive to these guys and please
them sexually.

  There was one particular day that I remember, that I was surfing online
gay personal sites, one in particular I used a lot where I knew a lot of
hardcore tops frequented and were especially into fetish and kink. I had
come across a personal of a white guy that I was interested in. He showed
only body photos and mostly did not include the face except for one shot
where the lower half of his face and jaw were visible. He was really buff
and well built, and it looked like he certainly had a fetish for caning as
he had a very wide variety of canes, according to what I could see in his
pictures. He looked uncannily like my current headmaster though I brushed
it aside. His profile name was "SternCaner" and it read as such:

 "Middle aged dominant white male into corporal punishment and especially
caning. Into sports and fitness. Extremely well-practised with the cane,
has a wide assortment of paddles, straps. Only serious bottom boys to
apply, place available. Fit asian bottoms a big plus."

  I eventually messaged him over the site and sent some pictures of myself
without face pics, but strangely never received any reply. I went on with
meeting my other tops and soon forgot about him.

  Soon after, I got into trouble at school again. I was a bit of a problem
student on and off, and usually would be up to some form of misbehaviour.
This time, I had been caught cheating in a mid-term exam (I did that
sometimes as I really didn't enjoy the books). Needless to say, punishment
was usually swift in coming. Since it wasn't the first time and the exam
was a fairly major one I was marched to the Headmaster's office promptly. I
wasn't too bothered at that time since I was in a way, pretty used to it. I
remember standing with my hands behind my back, looking at the Headmaster
from across the desk. He looked stern as always and very no-nonsense. He
gave me a dressing down the usual spiel about how serious an offence
cheating was. The punishment, he announced, would be the cane, and that I
would be required to report back to his office after school hours the day
after in my gym attire (this was the norm). I guess making the boy wait for
a day before punishment served to make him dread and fear it more and
reflect upon what he did, making the punishment all the more dramatic. It
had that effect on me too, in addition to making my cock extrememly hard.

  The day passed agonizingly slowly. I went to school the next day and the
day too, passed slowly. I could literally feel my heart beating along my
buttcheeks as I anticipated what was to come. Given his reputation for
really severe canings, I wondered how I would fare. The corridors were
pretty much deserted by the time I started walking to his office. I could
hear my footsteps down the cold floor, till I stopped in front of his
office. Now, let's get back to where we left off at the start....

  I stared at the door in front of my Headmaster's door, feeling a lump in
my throat. My heart was pounding in my chest, not knowing what to expect,
and my cock was rock hard by now, straining against the gym shorts that I
was wearing, in anticipation of what I hoped was to come. I knocked on the
door, hearing it echo down the corridor, and I heard his voice clearly
through the layer of wood separating us.

  "Come in," he said.

  I opened the door, walked into his office, and then went up to him,
standing in front of his table, hands behind my back. He continued writing
busily at this desk, appearing to be quite oblivious of me standing there.
My eyes quickly fell upon the cane resting of the front of his desk. This
was a mid thickness cane, and I knew how these felt. Too thick and they
thud hard but don't sting, too thin and they sting a lot but don't leave
very thick welts and they don't give off much of a dramatic sound. Medium
ones however, are used by the ones who truly know about caning, they can
sting like hell and really hurt, and the sound it makes on vulnerable
buttock flesh is loud and emphatic. My heartbeat definitely picked up as I
realised what I was dealing with. I also noticed that he left his cabinet
open, and it showed off a hell of a selection of rattan canes, I estimated
at least 12 to 15 canes. This was a man who knew how to dish out punishment
I was sure.

  Now he looked up at me, removing his glasses and placing them on the
table. "Now, Matt, I hope you have reflected on what you have done and how
serious it is."

  "Yes Sir," I replied, looking at him. I couldn't help but feel how
closely he resembled that guy from the caning website, now that I was so
close to him. My cock continued throbbing, at full attention now. I though,
this could be a chance to take a school caning "to the next level" so to
speak.

  "Cheating has and will always be a serious offence, and the punishment
has to reflect that. You will be caned today, Matt"

  "Yes Sir, I'm sorry Sir." I was insanely worked up and horny now.

  "You will receive 36 strokes of the cane on the buttocks."

  My heart leaped, this was a pretty large number for a school caning. I
gulped, not knowing how to reply, but just nodded my head.

  He slowly got up off his chair and picked up the cane, walking towards
and then behind me. He swished it in the air swiftly and sharply a few
times, and the force in his hand was unimistakable. I could hear the swoosh
of the cane as he stood at the side of me now. I thought to myself, should
I try to "seduce" this guy, and how?

  "I want you to bend over and put your elbows on the table. Buttocks tight
and push them out." he said sternly.

  It was customary that canings were delivered on covered skin. We kept our
shorts on, and the caners, and those receiving, all knew this.

  I decided that it was now or never. I gulped, and hooked both thumbs over
the waistband of my shorts and underwear, and pulled them all the way down
in a single motion down to my ankles. My head was spinning and I couldn't
notice how he reacted to this. All I knew what that my cock sprang free,
and was so hard that it immediately sprang back flush against my stomach,
pointing straight up. I looked down, it was visibly throbbing, and I could
see my cock head was shiny from my pre-cum leaking out. It had to be
obvious to him how insanely aroused I was. Apart from that, I had fading
but still very obvious welts on my buttocks from an earlier session I had
with a top a few days ago. If he noticed them, he didn't say anything.

  I did not turn around to face him, instead looking forward, pretending
nothing happened. I waited awhile, letting him take this in, and then as he
instructed earlier, I bent over slowly. I was familiar with this position,
I placed both elbows on the desk and put my head down. I spread my legs a
bit and pushed my stomach down a bit lower. I pushed my buttocks as I was
told.

  He said nothing for awhile, I'm sure he was processing things and seing
what he should do.

  "Spread your legs wider Matt," I heard him say as he stepped behind me.
He tapped the inside of both my thighs as he said so, adding more empahsis.

  I spread my legs apart wider, I could feel my asscheeks pull apart now,
as my cock continued to throb.

  He tapped my buttocks with the cane now. "Buttocks out."

  I pushed them out for him.

  From the corner of my eye, I saw him step slightly back, cocking his
right arm fully back, then unleashing a full blooded stroke. I knew
immediately I was in for a serious caning. The crack of the cane was
tremendous, it must have been heard through all the empty hallways. The
pain was immediate and incredible and I cried out once, trying immediately
to stifle it. My buttocks felt like they were on fire and I straightened up
immediately, going up on my tiptoes, my hands shot back and I clutched at
my buttocks in pain.

  I knew I could take a lot of punishment from all the canings I took over
time but this was on a completely different level entirely. I kept my mouth
shut, biting my lower lip as the pain reached its crescendo. My breathing
was ragged and heavy, and this was stroke one.

  "Now you will get back into position. You just earned yourself an extra 3
strokes for that." the Headmaster said.

  "I'm sorry Sir, I will do better."

  I bent back over the table and tried to regain composure as he once again
positioned my buttocks with the cane.

  The next stroke was just as painful, for each stroke he would lean back
and use body weight, momentum and his formidable arm strengh to really lay
it across my buttocks. The pain was even worse now but I managed to
maintain position, even as I squirmed and my buttocks quivered.

  "Two Sir, thank you Sir,"

  He knew exactly what he was doing. His strokes were "followed through",
as if he were caning "through" my buttocks. This gave each stroke more
power, instead of caners who would lift the cane off the buttocks after
impact. His technique and aim, I could tell painfully, was extremely
polished. He could deliver each stroke nearly one on top of the other if he
wanted, and he knew exactly how long to wait in between strokes, allowing
the pain to reach it's peak before immediately unleashing the next vicious
stroke

  Even though I was a seasoned recipient, I whimpered quite a bit. My cock
would normally stay steel hard through a caning but the pain killed off my
erection after the fourth stroke. I squirmed as I could barely count now.

  "Four Sir, thank you Sir." I said as I bit my lower lip.

  The fifth stroke definitely drew blood as he laid on a really hard one
across my already welted flesh. This was the fastest anyone had ever drawn
blood from caning me. He stopped awhile and let the pain sink in. I was
breathing hard as I struggled hard to keep my position. It must have been
quite a sight for him. I knew I was in good shape, and my tops mostly
comment I have a great set of buttocks for caning, toned, muscular and yet
just enough of a bubble butt to give the caner a good target. And here I
was, naked from waist down, bent over, my legs spread open and my buttocks
pushed out and presented for this tough disciplinarian. Now having put
livid welts on my flesh, and him having a view of my asshole as well, must
have been extremely satisfying for him. And inside, I started feeling,
that's what I wanted to do, to satisfy this guy, sexually.

  Despite the pain that he reminded me of with each stroke, I started
feeling horny once again. I could feel my cock start to stiffen again,
getting hard pretty quickly as I remained bent over, feeling much like a 2
dollar whore, naked from waist down and my cock throbbing. He reminded me
of the pain with another stroke that quickly followed, and my buttocks were
once again, lit on fire. This time though, I remained absolutely hard. I
kept my elbows and palms on the desk and turned my head to the side,
pressing my cheek against the desk, so I could actually watch him give me
the caning. I pushed my stomach down low and spread my legs apart some
more, as he waited in between strokes. He could see me adjust and I'm sure
he got a better view from it. I started to sweat a bit from the exertion,
pain and also from the mounting sexual excitement and I could feel a drop
of sweat flow down my lower back, down my asscrack and deliciously over my
asshole.

  He lifted up his arm and followed up with another stinging stroke. This
time I moaned audibly as the pain seared through my bum, and I got up on my
tiptoes. My cock throbbed and my asshole twitched as I worked felt my mind
absolutely clouded by lust. My first bare bum caning in school was turning
out to be an absolutely erotic and painful experience.

  He reached 12 strokes, and there were 27 more to go. By now I was sure my
buttocks were already a mess of welts but I was even hornier now than when
I started. I gulped as he cocked his arm again, the next stroke landed just
above the crease between my buttocks and upper thigh. This one stung a lot
and I cried out, both in pain and pleasure.

  "Thirteen Sir, thank you Sir."

  He continued with 2 well placed strokes just above this one that nearly
had me hopping. The loud, crisp smack of the cane on my bared buttocks
continued to ring very loudly. I moaned again after the next stroke, and
deliberately pushed out my buttocks even more as my lust grew. He must have
gotten the sense that I had started to enjoy the caning a bit too much now.
I thought I saw what was a bulge on the front of his pants, as I looked at
him from the side, in my near nakedness. His next stroke showed me he
continued to mean business, as I clenched my teeth in pain as my buttcheeks
continued to burn.

  "Seventeen Sir, thank you Sir." my breathing was ragged now.

  He paused a bit, before placing another stroke squarely in the centre of
my quivering buttocks. This one hurt especially bad as my buttocks were
already badly welted in this area. I immediately straightened up, and
clutched at my buttocks again.

  "OOOWWWWWW!!!" I yelled, squeezing my buttcheeks hard, I could feel the
welts, and where skin had been broken and I was cut. The pain was really
intense this time. I took awhile to regain composure as the Headmaster
waited.

  "And that, young man, has earned you yet another 3." he announced. I
could sense he was really starting to enjoy this caning. Suprisingly, my
cock didn't really show signs of letting up as I quickly regained my
erection, displaying it proudly as I was clutching my buttcheeks. This was
really quite lewd, though he didn't make any comment at all.

  I was somewhere in between insanely horny and insanely in pain, but as
the sting died down I just wanted more.

  "Please Sir, may I bend over your sofa for the rest of my caning?" I
asked.

  There was a wide leather sofa in the corner of his room that had a pretty
low seat. I imagined bending over it and pressing my chest down on the seat
would stick my buttocks out nicely and give him an even better view and
target. He seemed to know what this request meant, and he nodded his head,
motioning to the sofa with his cane.

  I walked over to the sofa, my heart beating hard against my chest, and my
cock was visibly erect still, which I am sure he had totally noticed. I
bent over and pressed my chest down against the seat, keeping my elbows
close together, this served to stick my rump out, and I bent my knees a
bit, pushing out some more, keeping my buttocks tight, though opening up my
thighs to give him a good view. This must have drove him wild, because he
very quickly lined the cane up against my welted cheeks, tapping lightly
for aim, then unleashing a mind-numbingly painful stroke.

  I grit my teeth down hard. "Yearrrrghhhh," I cried out, but still
managing to keep my position. My thighs trembled in pain as I tried to
ignore the pain from my 20th stroke. I still had not even reached the
halfway mark taking into account the 6 extras I had earned.

  "Twenty Sir, thank you Sir,' I could barely even manage.

  The next 6 strokes were slow, deliberate and found their mark
excellently, leaving my buttocks an even more heavily welted, quivering
mess. He landed them low initially, starting over the lower buttocks just
above my thighs then worked his way up, eventually hitting just above
centre on the 6th stroke. I was in absolute agony, constantly shifting my
feet and squirming, but kept my buttocks pushed out at all times, I was
definitely breaking a sweat, and I think so was he. It couldn't have been
too easy delivering every stroke like that, though I'm sure he enjoyed it.
The scene could probably have been in a porno. Fit, toned, horny boy in his
late teens naked from waist down, covered in a sheen of sweat, bent over
with his bum stuck all the way out, covered in welts, his cock hard and
dripping pre-cum, and a middle aged, muscular, white male standing behind
him, a hardon tenting his business trousers, and wielding a nasty looking
cane in his arm.

  He continued his slow, painful, yet insanely hot caning. Each stroke
really stung like hell, but through the pain the sexual energy of the whole
situation kept me horny and on edge.

  "Thwack!" My buttocks quivered as a new welt formed right smack across
the centre.

  "Thwack!" This stroke fell diagonally across. The pain was tremendous and
had my knees shaking.

  "Thwack!" This one striped the upper part. I kept my bum pushed out,
waiting for the next one. My cock was steel hard, throbbing and oozing
precum relentlessly.

  "Crackkk!" The cane marked me deepy just between my upper thighs and
buttocks.

  As the strokes came slowly and consistently, I felt my balls swell up as
if till bursting, my cock straining and ready to spew. Though my asscheeks
were positively on fire, welted up and bleeding, I never felt hornier, and
I was sure I was going to bust a huge load. I stayed bent over, presenting
myself lewdly to this man, opening my thighs to show him my eager fuckhole.

  He lined his cane up against my buttocks again, tapping lightly a few
times, steadying his stance, then leaning back a good bit, then lashing out
full strength with his powerful arm. This stroke cracked viciously with the
loudest smack up till that point, possibly drawing some blood as well. The
sting and burn was increadible as I cried out loudly, partly moaning as
well, then I felt my cock spasm and finally explode in a huge orgasm.

  "Oh fuckkkk.... I'm cumminggg!!" I moaned out. I felt the warm cum
splatter against my stomach as I started spewing my load. Ropes of cum
landed over his sofa as well as I exploded in an orgasm larger than I had
ever felt before. My thighs and legs were shaking from the intensity of the
orgasm as the Headmaster moved beside me so he could watch my cock spew its
load. I was moaning loudly as the waves of my powerful orgasm raced through
my body. Feeling incredibly horny still I squatted down as I continued
cumming, spreading my legs wide apart and leaning back, thrusting my hips
forward and I started openly masturbating and jerking my cock further as it
continued pumping an immense cum-load. My cock was slick with precum and
cum and i slid my hand easily over its shaft. I could feel my asshole
twitch and spasm in time with my cock as well, as I closed my eyes and
swallowed, trying to ride out my orgasm. I was still spurting hard, ropes
of cum messing up the Headmaster's sofa and the floor. All the while, he
watched wordlessly, and I'm sure all the concealed sexual undertones this
caning had up till now, were by this act, completely out in the open.

  I shuddered as I came down from the really hard orgasm, still pumping my
twitching cock, squeezing it dry as the last few drops of cum oozed out. I
realised that I had been holding my breath up till this point, finally
exhaling, and breathing a bit more regularly now.

  "Now, I didn't give you permission to cum now did I, look at the mess you
made." I heard him say, standing beside me now, watching me fist my cock.

  I suddenly felt sheepish and realised how inappropriate this looked if he
seriously meant business and wasn't interested at all in the sexual part of
this whole situation, though unlikely.

  I quickly pulled my hand away from my cock, leaving it still throbbing
and at attention, and got up from my lewd, open legged squat.

  "I'm sorry Sir, I will bend over again." I said softly.

  I kept my legs open and once again pressed my chest down low, this time
feeling my warm cum against my own body, this was hot. I was still hard and
throbbing, still feeling horny and not satisfied yet though I had cum hard.
The edge had been taken off by the intense orgasm but I think I was used to
being fucked after canings and that was what I wanted now.

  "For that shameless display, I am adding another 12 strokes to your
punishment. That means there are another 23 strokes to go boy," the
Headmaster said.

  I remained bent over, getting myself ready for the next stroke, trying
hard to compose myself. The Headmaster didn't show any signs of letting up
with the next stroke. The sting was incredible as he lashed my buttocks,
and having just orgasmed, the pain was much harder to bear. I quivered as I
waited for him to continue. Surprisingly, the next stroke did not come when
I expected it to.

  The Headmaster walked up behind me, and I felt one of his hands grab my
heavily welted right buttcheek. He squeezed firmly, and I half wainced in
pain, half moaned in pleasure. I knew now that at this point, the caning
has crossed the line between strictly business and pure sexual lust. I
remained still and did not protest as he no doubt admired his handiwork
with the cane and kneaded one asscheek. I practically felt my asshole
twitch in anticipation.

  "You enjoy this more than you feel the pain don't you boy?" he said.
There was a noticeable change in the tone of his voice.

  "Yes Sir," I shamefully, my voice choked up with lust.

  "We're going to have to do something about that now don't we then?"

  I could hear his footsteps as he walked away. I heard him opening a
drawer, and I turned my head to the side to look behind me, my bum still
thrust up and out for him. I saw him pull out what looked like a paddle. I
got a closer look as he walked back, turned it that was a leather paddle,
and apprently quite well worn. I had been on the business end of leather
paddles before. The flexibility of the leather made for a much more painful
smack and a good loud satisfying sound for the top, and for those who
really were experiences, they would know that it was much more painful than
plastic paddles.

  "Buttocks out boy, open up your legs further."

  I eagerly obeyed him, sticking out some more and even getting up on my
tiptoes, bracing myself as I spread my thighs apart.

  "Thwack!" the pain was excruciating on my already thoroughly punished
buttocks. Instead of a sharp sting, I felt the pain like a deep aching
bruise, and subsequently like my whole buttcheek was set on fire. It was a
sharp contrast to the cane but given how hard it was delivered by the
Headmaster's strong arm, the pain was equally bad.

  What followed was a relentless assault on my buttocks with the paddle. He
followed each whack very soon with another, punishing my asscheeks
severely, alternating each smack on both my buttcheeks, giving them an
equal number of smacks. They were delivered with such force I felt my face
and chest being pushed down into the worn leather of his sofa. I moaned out
loud and then started cyring out in pain after about 12 to 15 smacks. The
pain was incredible as I squirmed and struggled to maintain position, my
erection vanished quickly and my cries became louder, though I was
determined not to cry. The smacks rang loudly through the room, mixed in
with my cries of pain. After about 30 vicious smacks, he lay the paddle
down beside me and bent down to pick up my underwear from the ground beside
his table. He walked back to me and roughly opened my mouth, forcing my own
underwear in and effectively gagging me. He then picked up the paddle again
and continued his punishment, giving me another 12 to 15 resounding smacks.
My cried were muffled by the gag as my backside screamed out in pain. He
was nearly bringing me to the brink of tears, before he put down the paddle
and walked up behind me again. My mind was spinning and numb with the pain
I felt in my buttocks, I could almost feel my heartbeat throb all over both
my buttcheeks and I was sure they were completely red and angry from the
paddling, and not to mention with a mess of welts covering it from the
earlier caning. This was by far one of the most intense caning / paddling
sessions I'd ever had, and I had the feeling it was far from over.

  He stood beside me now, and pulled out the underwear gag from my mouth.
My chest heaved with relief as I breathed heavily, trying to focus on
something apart from the pain. He grabbed my asscheek again roughly and I
immediately winced, this was much worse after the paddling, and I could
feel the heat coming off the surface of my punished buttock. He loosened
his grip, then I felt his thumb come up right beside my pouting asshole,
and the rest of his fingers gripping my asscheek, before he tightened his
grip, effectively pulling my asscheek wider apart. No doubt he wanted a
good look at my tight teen fuckhole, and I wanted him to see it.

  I could hear him unbuckle his belt now, and I watched him as I lay bent
over, my head turned to the side. He pulled his zipper down, as I gulped in
anticipation. He must have been in a whole lot of discomfort I realised,
when I saw the huge erection that immediately tented his boxers as his
pants dropped to his ankles and he stepped out of them. His other hand
remained firmly planted on my asscheek as I remained submissively in my
position. He shrugged off his boxers and my jaw nearly dropped as I saw his
cock spring free. I had been used to the size of other Asian guys and
though I'd been fucked by white guys before, this guy was huge. His cock
was steel hard, and it curved upwards slighty, his cockhead was swollen and
shiny, also glistening with precum and by far the biggest I'd seen (and I'd
spread my asscheeks for plenty of guys by then). What impressed me most was
his length and girth, he was thick as hell and the veins ran along
his entire shaft. I'd never been fucked by anything that thick, even when
taking toys and dildos into account, and his length was equally impressive,
I'd estimated 9 inches easily, given that he must be at full hardness now.

  I watched him as he spread his legs slightly, his hips slightly thrusted
out, and he slowly fisted his hard cock. coating it with the abundant
precum seeping from his cockhead. He then let go, his cock throbbing as he
gripped my arsecheek harder, then giving it a firm spank with his hand,
which gave me a jolt of pain not far inferior to a smack of his paddle.

  I knew he wanted to take my hole, and I reached back now with my own
hands, one hand on each asscheek, feeling how intensely warm they were from
the caning / paddling. Spreading my legs some more, I stuck out my bum as
far as I could and stretched my asscheeks apart as wide as I could get
them, till it actually started to hurt a bit. My hole now lewdly exposed, I
proceeded to relax my shitter, then flex and pout it open, as he watched me
intently, still fisting his cock.

  My hardon returned quickly, in full force, and I felt my arousal more
intensely than ever before. I kept my asscheeks sluttishly apart for him,
waiting for his next move. He moved his hand and I could feel him pressing
against my pouting asshole with his thumb, I relaxed and opened it up
further for him. He could feel my shitter open up and he started rubbing
it, applying a bit of pressure. I moaned and pushed my bum out some more,
keeping my asscheeks wide apart. He removed his thumb, and I heard him spit
once, and soon after felt his spit squarely over my asshole.

  "You're a slut for cock aren't you, and you've been getting canings for a
long time now I suppose?"

  "Yes Sir, I am"

  "Who gave you those welts before today's caning?"

  "One of my tops Sir, I meet him regularly for caning and sex."

  "How often does he cane you?"

  "He canes me once every few weeks, but I meet other tops regularly for
caning Sir. I get weekly or sometimes twice or thrice weekly canings when
I'm more horny Sir"

  "Slut, how many was the most you had in a week?"

  "I received 9 canings in a week once Sir. They were mostly different
guys."

  "Do you always get fucked after?"

  "Yes Sir, mostly. I enjoy anal sex after caning, or even just assfucking
alone."

  "How many cocks have you had in your boycunt, slut?"

  I thought for a moment before replying, knowing how much I opened my legs
and asscheeks for random cock. I didn't want to deter him from fucking my
needy shithole.

  "About 25, Sir." I knew full well I had been fucked bareback by at least
twice that number.

  "Hot, you're a teenage slut aren't you, for cock, and for the cane."

  "Yes Sir."

  He started using his thumb to rub the spit over my asshole, applying more
pressure as I relaxed my sphincter for him, allowing his thumb to slip
easily into my fuckchute. Renewing my grip on my asscheeks, I pulled myself
further apart as his thumb worked its way fully in, up to his knuckle. He
then pulled out and pushed one finger in fully, then added in a second. I
stretched easily and both fingers went in deep. I was even harder then I
was before my orgasm by now, I moaned out loudly and my cock was twitching,
jerking and oozing precum, as he deeply fingered my asshole deeply.

  "Fuck, that feels good, fuck my asshole hard." I groaned as his fingers
slipped in deep and thrusted firmly.

  He fingerfucked my shitchute as he caned me, roughly and firmly, only
considering his own perverse sexual pleasures, and I loved it. I kept my
ass spread wide, thrust out and started slowly fucking back against his
fingers. He thrust hard and fast, going knuckle deep each time and my cock
practically throbbed with arousal. I grunted and panted as his pace built
up. I did not need much lube apart from his spit, being seasoned at taking
deep assfucks, and he penetrated me easily. I felt him withdraw abruptly,
and I felt the sudden void as his fingers left my hole. He resinerted them
quickly, and then I felt him squeeze in a third. I relaxed, and his finger
entered fairly easily, my crapper feeling instantly tighter. I was swooning
with lust now as he roughly manhandled my boyhole.

  "Slut, you are enjoying this too much aren't you?"

  I gulped with lust and nodded, my head still turned the side. He was
fisting his impressive cock with his free hand as he continued his
relentless assault on my tight backdoor. He seemed to have grown even
harder, his head swelling up even more as he occasionally used his finger
to smear the precum around the tip of his cock. He let go of his cock, and
I watched it spring up against his stomach, rigid, ready to fuck.

  He then reached down and wrapped his hand around my cock now, his other
hand continually penetrating my hole, stimulating. He pumped my hardness a
few times, and I literally nearly immediately exploded in another orgasm as
my asshole spasmed. He seemed to notice this, and let go of my pulsating
cock, continuing to finger me hard. Even though he wasn't jerking me off, I
felt another orgasm beginning to build up and my sphincter start to spasm
around his fingers.

  "Ohh.. fuckk... I'm going to cum again." I moaned out loudly.

  The headmaster immediately pulled his fingers out of my asshole, leaving
my hole gaping for a bit as I felt my impending orgasm ebb away. My balls
were literally aching to cum and my cock strained, throbbing as he left me
high and dry. He watched as I squirmed, and I begged him, "Please, let me
cum, finger my fuckhole so I can cum, Sir."

  I kept my thighs apart and stretched my asscheeks even wider, I
winked open my tight anal orifice and tried to open it up to entice him.

  "Slut, you really want it don't you."

  "Yes Sir, please," I begged.

  I watched him as he fisted his slick, hard cock again, and he walked
towards the sofa beside where I was bent over, and sat down, speading his
legs apart. His cock throbbed, fully erect, his cockhead glistened with
precum, as he slowly started to wank himself, looking at this horny, fit
teenager bent over his sofa waiting to be sodomised.

  I knew what he wanted before him even asking. I got up from my bent over
position and got on my knees, shuffling over till I was kneeling in betwen
his legs. He let go of his cock, and it sprang backwards, throbbing, hard,
bigger than any other I had had in my mouth till then. I knew how to suck
cock, I'd had plenty by then. I wrapped my fingers around the base of his
cock, giving it a few strokes, it was absolutely steel hard. He looked down
at me as I looked up at him lustily, then I opened my mouth and started
licking around his huge cockhead, lapping and flicking my tongue over his
pee slit, which was oozing precum still. It made for a good mouthful even
as I swallowed his precum and continued my tonguework over his cockhead. He
moaned out loudly as I tongued his cock, I slid my mouth and tongue down
his immense shaft, leaving a trail of spit on his already slick cock. His
cockhead filled up most of my mouth even before I could get much of his
shaft down. I could feel him thrusting his hips, trying to get it down my
throat and I gagged a bit, trying to get as much in my mouth as possible. I
slobbered as I sucked on his hard cock, the spit running out the corners of
my mouth and down my chin as I gave him as wet and sloppy and messy a
blowjob as I could.

  He moaned out in satisfaction as I started bobbing my head back and
forth, moving my lips and tongue up and down his slick shaft, maintaining a
steady suction. I still couldn't get much of him down my throat so most of
his cock was still outside my mouth, so I alternated giving him a good
sucking and allowing him to skullfuck me, and pulling out his cock to jerk
him off while I serviced his balls with my tongue and ran my tongue up and
down the rest of his cock that I couldn't suck. He grabbed me roughly by
the back of my head and hair, thrusting his hips out. I was determined to
deepthroat him, take him balls deep in my mouth. I was pretty experienced
at doing that as well, and could take a pretty big cock down my throat, but
right now I was still working on suppressing my gag reflex to allow more of
him into my mouth. I bent forwards and let the shaft slide down till it was
pressing against the back of my throat, then relaxed the muscles at the
back of my throat and forced my head down further, pushing his cockhead
down into my throat as I stopped myself from gagging. He slipped in and I
felt my neck bulge, spit running out my mouth and down his shaft.

  He moaned out loudly as he felt his cock slip into my throat. After the
initial part, it was easier keeping my gag suppressed and letting his
entire shaft slide in, though I literally felt the breath being forced from
my lungs.

  "Ah fuckk, that feels good, you're a little cocksucking slut aren't you?"
the headmaster groaned out loudly as I expertly deepthroated him.

  I didn't reply, instead concentrating on allowing him to fuck mythroat
with deep thrusting strokes. I slobbered over his shaft as he skullfucked
me, and sucked hard, my cheeks hollowing in. I ran my tongue along the
underside of his shaft and licked at his balls when he bottomed out on my
throat. He moaned out in approval as I did so.

  Once I had established a steady rhythmn and my throat had adjusted well
to his large girth and length down my throat, I started giving him the
blowjob of his life. I slid my hands down his inner thighs and pushed them
apart, getting up into a squat with my thighs wide apart, and adjusted my
position and roughly fucked my own throat down on his cock. My asshole
pulsated in anticipation of having his huge fuckpole up my shitter. I kept
up the pace, bobbing my head up and down energetically, the room filled
with the disgusting squelching and slurping sounds of my blowjob. He lay
back and enjoyed it, but showed no signs of being close to cumming. I guess
he was used to getting hot sleazy blowjobs from sluts like me.

  I would come up for air every once in a while and fist his sloppy, spit
slicked shaft and lick at his balls as I took a break from deepthroating
him. I kept up at it for a good 20minutes, not rushing at all, making sure
he had full satisfaction. Moving downwards with my mouth, I licked at his
huge hanging balls, as I stroked his hard shaft, then moved down further. I
was well used to giving random guys deep rimjobs and was about to show the
Headmaster I kneww how to be a proper slut and eat ass. I placed both my
hands at the backs of his knees and pushed them upwards and back, spreading
them apart as I slid my tongue downwards to the area between his balls and
asshole, tongueing the sensitive area. He reached down to hold his legs
apart and I used my hands to spread apart his asscheeks before tongueing
his shithole directly, flicking my tongue over it and sliding it around the
rim. He moaned out loud again and relaxed his hole. My tongue sensed the
give as he relaxed his sphincter and I pushed it firmly inwards, stiffening
my tongue and pushing it deep inside, giving him a good, deep rimjob. He
certainly appreciated the rimming, and I could feel his cock twitch in
pleasure as I tongued him deeply. I knew how to eat ass properly and
alternated flicking my tongue around the edge of his shithole, and applying
pressure and tonguing around and on his asshole firmly, then pushing my
tongue up his hole, flicking it around as i did.

  I kept rimming him, watching him moan and writhe in pleasure, my own cock
throbbing at this lewd shameless act. Tasting his ass on my tongue gave me
a heady, drugged sensation. I reached down, pumped my already hard shaft,
using a finger to gather up some of my precum dripping off my cockhead,
then reached down between my own widespread legs and lubed up my tight,
pouting shithole. The rimjob I was giving him was wet and sloppy as hell,
and I stopped awhile, spitting in my own hand rubbing my spit over my
asshole, then thrust 2 fingers in easily and started fucking it hard,
feeling my cock throb even more as I penetrated myself.

  "You fucking your own shithole boy?" he asked, looking down at me between
his legs as I continued eating his asshole.

  "MMphh," I replied, nodding my head, not even stopping as I continued
rimming him.

  After a rough fingerfucking off my own ass, I pulled my fingers out and
pushed his legs further back and got my face deeper in his ass, giving him
long wet strokes with my tongue along the length of his asscrack and kept
working my tongue, lapping at his shitter and tasting him. I sensed him
getting even harder and more aroused. I reached up and as I rimmed him
deeply, started fisting and pumping his slick, hard shaft. I was literally
trembling in anticipation as I felt how thick and long he was, wondering
how it would feel taking his entire impressive length deep up my fuckhole.
His cock was still wet and slick from my earlier sloppy blowjob, as I
pumped him with my hand, getting him even harder, if that was even
physically possible. I could tell he was close judging by the way he was
breathing, and I desperately wanted to get him off properly.

  I took my tongue off his asshole and quickly wrapped my lips around his
cock again. He put his legs down now and kept them apart as I resumed my
blowjob again, thrusting his hips upwards to fuck his cock back into my
mouth and throat. His shaft still felt immense in my mouth and down my
throat even though it had just been stretching it open. I held his thighs
down with my hands so that I could control the pace but quickly built up a
good rhythmn, relaxing my throat and getting his shaft down all the way,
slobbering all over his cock and balls. I bobbed my head up and down
quickly, hearing his breathing get faster and more shallow, and allowed him
to skullfuck me now, and he brought one hand down to grab a my hair and
pull down at it roughly . I enjoyed it when my top gets rough and allowed
him to treat me however he wished. He brought his feet up on the sofa, his
legs still spread apart, and used them as leverage to thrust upwards,
fucking my mouth. I saw him reach a finger beneath him and between his
asscheeks, and push it up into his own asshole. This was extremely hot, I
thought. As dominant and undoubtedly top he was, he wasn't averse to a bit
of ass play himself. He thrust his finger in deep and fucked it in and out
of his own hole.

  I stopped my blowjob for awhile and looked up at him. "Let me do that for
you, Sir." I begged.

  He smiled knowingly and pulled out his finger. "Have a taste boy." he
said. I immediately opened my mouth and allowed him to slip his finger in,
swirling my tongue around his soiled finger, tasting his bowels.

  I replaced his finger with my own, as I felt him relax his asshole for
me. I knew instinctively what to do as I hooked my finger upwards towards
his prostate and started rubbing at it, stimulating him even more. I
alternated rubbing his prostate with long, deep and slow strokes with my
finger up his ass, all the while keeping up the messy blowjob I was giving
his cock. I was frankly quite impressed with his staying power, as most
other guys would have blown a huge load long ago. "This guy is probably
going to be quite the stud when it comes to fucking later." I thought.

  Before long, I felt his balls tense up and his cock start to twitch in my
mouth as he muttered, "Fuckkkk boy, I'm cumming,"

  Immediately, I relaxed my throat and took him balls deep all the way
down, and added a second finger as soon as I felt his asshole start to
clench and then relax. Instead, he reached down with his hand and applied
pressure against the base of his cock to stop his orgasm and got up quickly
onto both feet, standing up on the sofa and pulling his cock out of my
mouth. "I'm going to cum in your mouth and all over that fucking face boy!"
he growled.

  He then spread his legs wide apart and got down into a squat, so his cock
was back at my face level as I kneeled before him. Then he yanked me
forward by the hair and thrust his cock back into my mouth. Reaching down
and behind him, he pulled one asscheek to the side. "Put your fingers back
in there cunt" he said.

 Hot, really hot, I though. I reached back and slid 2 fingers back into his
asshole as he squat down lower. He undoubtedly enjoyed anal play himself,
and I pushed in deep, rubbing forwards against his prostate. I gave his
cock a few strokes with my mouth and he immediately exploded in an immense
orgasm.

 "Arggghh fuck, bitch!" he shouted out.

  He shuddered and I could immediately feel his spincter muscles spasm and
convulse so hard around my fingers I thought he would break them. His
cumload was huge as I felt him nearly fill up my mouth within the first 2
spurts. His cock twitched as it spunked hard into my mouth and I could soon
feel some cum dribble and leak out the side and down my chin. He
immediately pulled out when he saw my mouth was filling up and he
masturbated himself over my face as he spewed even more ropes of cum
straight over my face, hair and eyes. It was the most impressive load I had
ever dealt with and my face was soon criss-crossed with his load and I
could tell he was hardly even done, as he continued stroking his cock,
pumping more cum out as he squat down lower over my penetrating fingers. I
rubbed at his prostate harder trying to milk more of his cum out as he now
aimed back into my mouth and shot some more into me.

  "Fuck..... you're such a fucking cum slut." he moaned, shuddering as he
rode out his orgasm. I could see his muscular thighs straining to keep his
balance as he milked up the remaning drops of cum into my mouth.

  I was breathing hard myself, my own cock still hard, realising that in
the heat and intensity of the moment I'd had pushed 3 fingers from my free
hand deep up my asshole as he'd erupted in his orgasm. I must have looked
quite the slut, kneeling before this stud, his cum all over my face and in
my mouth, my cock hard and my own fingers up my butthole.

  Looking straight into his eyes, as he looked down at me lustily, I kept
my mouth open, so he could see exactly how much of his cum I had in my
mouth, then slowly and deliberately, I swallowed once, feeling the huge
load quickly move down my throat. As he fisted his slowly softening, but
still immense, cock, he slapped my face with it, then used it to push the
ropes of cum he'd shot over my face, into my mouth, then slid his cock back
into my mouth and slowly started pumping again.

  "Mmmmmm, very very good, boy," he groaned. "And I still haven't even
fucked your asshole yet."

  I allowed him to continue fucking my mouth, feeling his cum and my tongue
swirl around his now softer shaft.

  "You want to feel that cock up your ass boy?" he asked.

  I pulled my mouth off his cock and eagerly nodded. Opening my mouth
again, I looked at hime as I swallowed again, making sure he saw that when
I opened my mouth again, that it was completely empty.

  "Very good then, now you have to make me hard again." he said, rather
matter of factly.

  I was so in heat now I would have done anything to get him hard so we
could have anal sex, and I got up quickly, knowing what we could do next. I
walked over to the cabinet where I knew he kept his canes. He had a wide
assortment for sure, there were at least 12 to 15 different canes of
different lengths and thickness, but one immediately caught my attention. I
didn't notice it before, it was definitely a lexan cane (acrylic / plastic)
and from personal experience I knew these hurt a hell lot more than rattan
and were yet whippy and flexible. It was black in colour, and medium
thickness like the one that was being used on me earlier. And in addition,
the shaft was not totally smooth, it was kind of ribbed or segmented like a
length of bamboo. It sure as hell looked more sinister and wicked than any
other cane I had laid my eyes on. I immediately picked it up and walked
back over to the Headmaster, who was now laid back, naked, against the
leather back of his sofa, looking at me as I chose my implement of pain and
his pleasure, and stroked his cock slowly back to hardness.

  " I see you have found my favorite cane, boy. This one is not for
amateurs, but I'm sure you will manage, being the cane slut you are," he
remarked.

  I handed him the cane, my cock sticking out shamelessly. "I know this
definitely will get you hard again, and you are far from finished with my
caning Sir. I can't remember where we stopped Sir, so I think zero is a
good place to start again." I sluttishly told him.

  "You will regret this boy." he said as he took hold of the cane and stood
up. "Bend over, show me that ass."

  Bending over again on the sofa, I felt my cock so hard it was flush
against my stomach. Again, I spread my legs wide apart and sluttishly
presented my buttocks to him, which were criss-crossed with the welts he so
deliciously laid on just earlier. I pushed my ass buttocks back out towards
him, and bent my knees, going up on my toes. I could sense him approaching
me from behind.

  "Spread yourself open boy," he said.

  I reached back with both hands and once again pulled my welted asscheeks
apart for him. Relaxing my spincter I pouted my fuckhole for him, flexing
it open, knowing how slick my asshole was with my spit and how inviting it
must look. He bent down and spit over my asshole, then I felt his thumb
press against it, slipping in easily. A few strokes with his thumb to
stretch me open a bit, then he pulled it out, one finger went in deep, then
two. I moaned in absolute pleasure as he anally penetrated me. He started
fucking my asshole harder with his fingers, spreading them apart inside me
to stretch my hole wider, then I felt his other hand reach around and his
fingers wrap around my throbbing, erect cock. He started pumping with his
fist, and it felt incredible. His fingers deep in my shithole fucking me,
and him masturbating me, got me right on the brink of an orgasm pretty
quickly. I kept my legs and assceeks spread, my eyes rolled backwards in
pleasure, a lump forming in my throat from my impending orgasm, and my
thighs tense and straining. Just then, he pressed in a third finger, and
started rubbing forwards against my prostate. My asshole had gotten tighter
since I was close to cumming now, and coupled with him jerking me off,
pushed me over the edge quickly, for the second time of the night.

  "Fuckkk, I'm cumming again!" I yelled.

  My body started shuddering hard as my cock erupted in another
mind-blowing orgasm. I spread my legs wider still to keep balance, and kept
my buttcheeks open as I violently spewed my cumload all over the
Headmaster's sofa again. Even though I'd already cum once, this load was so
pent up it seemed as large as the first, as my cock spasmed hard and
spurted rope after rope of boiling cum.

  I was struggling to keep myself from falling down, my shitter spasming
hard and squeezing the fingers still lodged deep within my fuck chute.

  "Ohh shittt.... just keep fucking my hole!" I cried out.

  I squirmed about, my head on the sofa, as I came so hard I nearly passed
out, my chest heaving. The Headmaster continued wanking me hard, my cock
now ultra-sensitive, and he pressed and rubbed against my prostate firmly,
milking me out as I had done for him earlier. I even caught my own face
with a few ropes of cum. I bent and straightened my knees, working my ass
up and down his fingers in unison with his fuck strokes, as I finally
started cooling down from the intense orgasm.

  "Shit, fuck, that felt really good, Sir. Thank you Sir" I moaned, barely
intelligibly.

  "Get up boy, keep my fingers in your asshole and squat up on the sofa."
he ordered

  His let go of my cock as I straightened up partially, enough to get my
aching legs up on the sofa, my asshole now more slack and relaxed after the
huge cum. I could feel my own cum under my feet and toes as I squatted on
the sofa, the whole room smelling of sex and ass play, wondering what he
had in store next. My cock was softening but still throbbing, aroused.

  "Tighten up your asshole," he ordered tersely.

  I did as he said, tightening my sphincter around his fingers, and he
pulled one out, the remaining 2 fingers still deep inside me. I pushed my
feet wider apart and spread my thighs open all the way, till they were
splayed open as wide as they could go. Shameless position, I thought, and
thrust my hips slightly forward and leaned back slightly, supporting my
weight with one hand. He then pressed his fingers in deeper still, getting
as deep as he could up my asshole, then again started applying pressure
against my prostate. He knew exactly how to push my buttons, as my cock
responded eagerly, regaining its hardness barely a minute after my most
recent cum. It was aching slightly from being so hard, for such a prolonged
period of time, but I was still itching for more action, having not been
fucked yet. He reached around once again and wrapped his fingers round my
cock and started stroking me to full hardness. The sensations were divine.

  "Tighten up as much as you can boy, it feels better," he said in my ear.
"And this big orgasm is just going to make your caning that much more
painful."

  I moaned and did as he said, keeping my asshole as tight as I could as he
continued rubbing at my prostate from inside, and alternating this with
long slow strokes in and out. Indeed the anal penetration felt more intense
and pleasurable the tighter I kept my hole.

  My cock was caught in between pleasure and a deep ache, but I stayed
painfully hard in spite of myself. "I want to see your cock hard for your
caning boy," he hissed in my ear.

  After another few minutes of delightful torture and stimulation, he
pulled out his fingers, leaving me thirsty and lustier then ever before. He
yanked my head back by the hair and thrust his fingers in front of me.
"Clean up the mess you made, cunt,"

  I was slightly taken aback not by him offering me his fingers, but the
state they were in. The huge orgasms and incessant anal stimulation must
have pushed my shit down really low and 3 of his fingers were deeply
streaked and smeared in a rich brown. The smell of my shit was strong and
heady, but I was so aroused and horny I didn't hesitate opening my mouth
and letting him push his fingers right in. I wanted him to know as I was
nasty enough that nothing was out of bounds. The taste of my shit was
acrid, not strong tasting, but the smell permeated my nostrils. I gagged
only very slighty at first but started sliding my tongue around his
fingers, cleaning them, as the Headmaster looked at his latest bitch
performing this shameless act.

  I used my tongue to clean them as best as I could, getting in between his
fingers and feeling the muck against my tongue. It was not unpleasant
definitely and after I'd gotten used to the smell, I found the act erotic
and submissive as hell. I pulled my mouth away, and, opening up, showed him
what must have been a nasty, filthy, shit coated tongue, before I swallowed
once, and showed him that everything went down. Swallowing was not a
problem, given that it was only a small amount, and he definitely got
turned on watching me.

 "Nasty, you're absolutely shameless aren't you. Bend over again, slut." he
ordered again.

  Again, thoroughly horned up now, my asshole aching and begging for
action, I bent over his sofa. I turned my head towards him, watching him as
he walked over to his desk and opened a drawer and reached in. He then
pulled out a string of anal beads and a large buttplug. The beads were
huge, the biggest I'd seen up till now, each one roughly the size of a ping
pong ball, numbering 5 in total and the buttplug was definitely generously
sized, very wide at the thickest portion and fairly long as well. I
immediately knew he wanted to stretch me out properly. Eagerly, I did what
I knew best, opening up my thighs as wide as I did before, I reached back
to once again stretch my asscheeks open as far apart as I could and pushed
my bum out, immediately I flexed open my shithole, just as he came up
behind me.

  "Good, very good, you better get used to this position," he said. "Tell
me how much you want it."

  "Please Sir, stretch my asshole open with your toys, open me up for your
cock." I pleaded, at the same time flexing and pouting my rosebud open.

  He spit on my asshole, making it even more slick, and I felt him press
the first anal bead against my opening, I relaxed and allowed it to slip
in, grunting a bit at the size of it, my asshole closing up after the bead.
He advanced the string quickly and inserted 2 fingers in, pushing the bead
in deep and then started with the second bead. I kept my asscheeks wide
apart, helping him get better access at my asshole and relaxed each time he
pushed a bed in. After he inserted one bead, he'd pull back and apply
tension to the string, halfway pulling out at the freshly inserted bead, so
that I felt my asshole stretch mightily around it. After a while, he'd
pushed all 5 beads deep up my ass, and left me with my cock absolutely
throbbing and me begging for more.

  Next came the buttplug. My asshole was warmed up now and I easily allowed
the tip of the buttplug in once I felt him applying pressure against my
shitter. He reached down once again and I felt his fingers again wrapped
around my cock. Aching, throbbing, but hopelessly aroused, he stroked me
till I was so hard I couldnt believe it, at the same time advancing the
buttplug slowly but incesantly deep up my ass. I could feel the anal beads
being pushed in even deeper, and the widest part of the plug now stretching
my shithole wide open. All the while he was masturbating me, I was moaning
like a bitch in heat. He eased the widest part in and my ass quickly
swallowed the rest of the huge plug. I don't think I'd ever been this full
before.

  He kept up the stroking and now started fucking my ass with the plug. It
was delightful torture again as my cock and balls ached, and his plug
slowing raping my asshole. He pulled out till it was nearly fully out, then
reinserted it deep in, my sphincter contracting and relaxing as he slowly
fucked me with his large toy. Finally, as I lay bent over, panting and
hopelessly aroused, he stopped, inserting the plug fully once again, and he
released my cock. Without saying in word, he walked back to his table and
brought back something. He came back up behing me and I soon felt a firm
strap being pulled around the base of my cock and balls. Looking down
between my legs, I realised he'd fastened a leather cock ring and started
tightening it firmly. My cock throbbed, steel hard, sticking straight out,
and my balls ached as the leather strap pulled tightly around them.

  "This is going to keep you hard for me through your caning, and I want
you to stay that way until I allow you to cum," the Headmaster said.

  This would be crazy, this would be torture, I thought to myself. My cock
hard, bound firmly in a leather cock ring, a string of huge anal beads and
a large butt plug in my ass, my legs wide open, ass sticking out and
getting ready for a caning by a naked, muscular white hunk and a good round
of ass fucking after, this almost seemed like a scene out of a hardcore
porn flick and was to me a dream come true. I remained in my position,
swallowing hard, the taste of my shit still in my mouth, waiting, waiting
for him.

  He picked up the wicked looking lexan cane from the floor and once again
lined himself up behind me, though this time naked, his cock, like mine,
totally hard again. He started with a bit of a tease, using the tip of the
cane, running it up along my asscrack, nudging at the flange of the
buttplug wedged deep in my ass. He then bent over the suddenly started
pulling on the buttplug hard. I gasped as he pulled it completely out,
gaping me and leaving me feeling suddenly empty. Then once again, he ran
the cane tip along my asscrack, this time pausing with the tip against my
butthole. I relaxed and pouted, and I felt him push in the tip, sliding the
cane into my asshole.

  "MMmmm..." I moaned out loud.

  Then he pulled it out, extending his arm, pushing the tip of the cane
towards my mouth, as he once again inserted the buttplug fully. I grunted
as the plug forced its way in, stretching me open, at the same time opening
my mouth and licked and sucked at the tip of the cane pulled freshly from
my ass. Then he pulled the cane away from my mouth and I braced myself for
what was to come. He lined himself up again, legs slightly apart for
balance and leverage, then, as he did the first time, tapped firmly a few
times against my welted buttcheeks.

  "Buttocks out boy," he commanded.

  I obeyed, bending my knees and arching my back further to push out my
buttcheeks. There was a loud swish and a resounding crack as the cane
landed full force against my welted flesh.

  "Yeowwchh!" I cried out loudly, my legs and buttocks immediately started
squirming at the sting and intense pain the lexan cane brought forth. I'm
sure the pain would have been excruciating even on fresh skin but my
buttocks were already reddened and severely welted by his earlier
punishment and even though I enjoyed the pain from canings so much, the
pain I felt this time was nearly completely unbearable. I felt a trickle of
blood quickly form on my bruised flesh. The Headmaster must have enjoyed
the view trememdously as he lined up his second stroke, the cane once again
resting against my flesh.

  "I'm starting from zero again given that you have forgotten to count,
boy," I heard him say

  Obediently, I once again pushed out my buttocks for him, getting ready
for the next stroke and balled up my hands into fists, bracing for the pain
to come.

  "Crackkkk!" this stroke stung even harder than the first. I yelled out
again, gritting my teeth. he was definitely not holding back. This stroke
was aimed perfectly, landing across the flange of the buttplug, pushing it
deeper in my asshole. The combination of pain and the stimulation I felt as
the plug was thrust deeper and rubbed against my prostate was strange yet
pleasurable. My cock twitched noticeably.

  "One, Sir. Thank you Sir," I could barely manage saying. I could
literally feel my heart throbbing across each new welt he lay across my
buttocks. The pain was incredible, but in spite of myself and because of
the tight leather strap around my cock, I remained absolutely erect,
showing off my arousal shamelessly.

  The caning was slow, steady and relentless. Each stroke was carefully
weighted, delivered at full strength, timed perfectly such that the next
stroke followed the previous just as the pain reached it's crescendo. It
was extremely clear how experienced the Headmaster was at maximising the
pain of each stroke. I remained as still as I could, presenting my buttocks
to him in a lewd a fashion as I could, legs spread, ass pushed out. The
room was filled with the smell of sex, cum, sweat, and the sounds of me
moaning and yelling in between the pain and pleasure, and the spine
chilling crack of each cane stroke delivered mercilessly over my thoroughly
thrashed buttocks. Each time I moved too much, didn't count promptly, or
straightened up from my position, the stroke would not count, and another
stroke was added onto the punishment. Numerous times, his good aim would
land a stroke over the butt plug and I would have that pleasurable
sensation of being fucked and caned at the same time.

  "Thwackk!"

  "Crackkk!"

  The sound of the lexan cane on my buttocks rang out crisp and loud
through the empty corridor outside his office. I heaved and panted loudly,
crying out with each stroke. I counted at least 14 or 15 strokes now, the
searing pain in my buttocks now nearly unbearable.

  "Five Sir," I counted. The numerous strokes that did not count kept the
number low even though my flesh was already burning in pain. With twenty
more strokes to go, I was sure I couldn't take so many. I was bleeding
again, yet I was immensely hard still.

  He put down his cane, reaching down to pump his hard cock with his fist.
"Straighten up boy, come over here, put your mouth to good use," he said
with authority.

  Grateful for the break from the excruciating pain, I straightened up and
squatted in front of him again. His impressive length and girth was in
front of my face again, and he was as hard as he was even before he came.
Lifting one leg up onto his sofa, he thrust his hips forward and I
immediately opened my mouth and took his cock in, allowing it to slide all
the way to the back of my throat. It took me awhile before my spit started
runnig freely again and I started sucking him eagerly. He reached one hand
behind him to once again slide one finger up his asshole, his other hand
grabbing the back of my head to skullfuck me deep. I felt his cock twitch
in my mouth as he got even harder from the anal penetration and my sloppy
blowjob. I came up for air gasping after a stretch of very forceful skull
fucking, my face was a complete mess from my own spit, tears and his
precum. He then forced my head under his ballsac and I went to work again,
sucking at his huge, heavy balls and then as he pulled out his finger, I
reached up to pull his asscheeks apart and went to work immediately with my
tongue on his shithole. I rimmed him deep, as best as I could from this
position, then decided to move behind him for better access. He bent
forward obligingly and I stretched open his asscheeks and dove in deep,
tongueing his asscrack, his shithole and inserting my tongue in deep, past
his sphincter, to really taste him.

  He moaned out his approval before pulling me by the hair and bringing me
to the front to work on his cock some more. I continued my sloppy blowjob
for another good 10 minutes before he had enough and pulled me to my feet.

  "Bend over, cunt, there are still 20 strokes to go,"

  I got up, my legs positively wobbling, my ass on fire and my rectum
completely stuffed and full, and I was absolutely cock drunk and horny for
more now. Quickly bending over again, I splaed my thighs open and awaited
my punishment.

  "You can have me in your office to cane and fuck any time you wish Sir,"
I lustily said.

  He smirked, and replied, "I knew that the moment you took your shorts off
and showed me your bare ass and hard cock, boy."

  He didn't waste any more time, lifting the cane up high and delivering an
extra vicious, stinging stroke, immediately setting my ass on fire, as if
to highlight his statement. I clenched my buttocks in pain as I felt the
heat and an immediate new welt form.

  "Six Sir, thank you Sir," I uttered.

  "Swish, crackkk..." the cane again broke skin, my buttocks trembling.

  "Swish, crackkkkkk!' this stroke was even more painful, and my cock
twitched and strained against the leather strap around it.

  I started sobbing now, tears finally flowing because of the pain. But I
dared not move or straighten up. Each stroke was more painful than the
last. It felt as if the Headmaster was increasingly turned on as the caning
progresed, and as he got even hornier, he caned even harder.

  "Crackkkk!" the sound of my beating resounded through the room.

  "Arggghhhh, fuckkk!" I cried out loudly, and promptly earned an extra
stroke.

  After he crossed 24 strokes delivered, the count was still at 10, and I
was writhing in pain on his couch, still pushing my buttocks out high and
keeping my legs open, my hole stuffed full with anal beads and his huge
buttplug. He decided he'd had enough and reached down, picking up my
underwear again and gagging me with it.

  "I'm giving you another 20 strokes, and that will be it boy. Now spread
yourself properly and push your buttocks out some more, up high." he
ordered again.

  I trembled as I obeyed him, my bum out high and my legs spread wide. At
least the gag would prevent me from screaming out too loudly, and he could
finish his caning as he pleased. But I knew another 20 strokes would be a
killer. He took his time delivering the rest of his punishment, enjoying
and savouring lining my buttcheeks with fresh. livid welts. My thighs
bruned with pain from the strain of holding position, spread open, and my
buttocks were seared red hot with every vicious stroke he lashed out with
the cane.

  "Swish.... crackkkkk!" Another welt formed over my arse cheeks.

  "Gnnnnmmphhh," I yelled into the gag.

  "Smackkkkkk!" This one was particularly stinging and had me up on my
toes, squirming in absolute agony.

  "Crackkkkkk!" Again and again the cane cut against my sore flesh, my
asscheeks by now absolutely covered and marked with welts, by far the most
painful, brutal caning I've had. I stayed hard, my cock throbbing against
the firm restraint of the leather ring around it, and also because of the
butt plug pushed deep into my ass each time a well placed stroke struck
against it.

  I counted out 10 strokes, with another 10 more to go, when he suddenly
stopped the caning. He came up behind me again and I felt both his hands on
my arsecheeks, and they felt like fire burning into my skin. I was
undoubtedly sore and bleeding as I felt him pry me apart wide with his
hands. My asshole clenched involuntarily around the plug, sending a much
appreciated wave of pleasure down my spine as he held my asscheeks open.
Then I felt him release his grip on me and tug at the butt plug lodged in
my rectum.

  "Turn over boy, lie back now,"

  Grateful for the temporary respite from the caning, I quickly obeyed and
turned over, lying down on the couch, awaiting his next move. I was covered
in sweat still, heaving and breathing hard. "Pull your legs back, spread
them wide," he said. I got my legs back to my chest and held them wide
apart with my hands, giving him full access to my stuffed hole and hard
cock. He squatted in front of me and spit once over my cock, and started
pumping it slowly with his hand, and with his other, pulled firmly on the
plug in my ass.

  "Mmmmphh, gnhhhh" I moaned, keeping myself wide open for him. He expertly
stroked my cock, and it felt absolutely great, even though it was still
aching. My shitter dilated then quickly allowed the plug to pop out my ass
after the widest part had passed, clenching quickly as he pulled out
completely. He gave me a few more firm strokes with his hand before I felt
the firm pressure of the tip of the plug against my ass again, I relaxed
and allowed him to penetrate my hole again. The pleasure was immense, him
stroking my cock and now inserting the plug deep in. Then he pulled out
again, and got into a steadier rhythmn, pulling out the plug and fucking it
in deep, my asshole repeatedly dilating and clenching as he fucked me
slowly with it. I looked down as he fucked me with the plug, the smell of
my shit permeated the room, and I could see the plug was definitely deeply
and thickly smeared in a layer of brown. He increased the pace as my moans
got louder and he stroked me faster, my cock now aching for yet another
release.

  My thighs were shaking as I was quickly approaching an orgasm. He looked
up at me and smirked, sensing my impending cum, "You wanna cum, boy?" he
asked

  I nodded my head eagerly, the gag still in my mouth. The tightness of the
leather band around my cock effectively prevented me from blowing my load
as he pushed me to my limit of endurance and continued his relentless dual
stimulation, penetrating my ass deep and jerking me off. My cock was now
spasming and straining against the ring and I was sure I would have blown a
huge load by now if not for it. I was struggling at trying to keep my
thighs apart with my hands and I was now shaking all over, needing
desperately to cum.

 Abruptly, he stopped and pulled away, pushing the plug back in fully with
authority, then stood up again. My body was screaming for another cum, and
I remained as I was, spread eagled, hoping he would fuck me, jerk me off,
anything, so I could blow my load.

  "Get up, boy, you have another 10 strokes to go," he said cruelly.

  I groaned into the gag, absolutely frustratingly horny. My cock throbbed
obscenely in front of him, but I knew there would be no way out of this
apart from finishing up my caning and waiting for him to thrust his cock up
my shithole. Slowly I got up and once again bent over his sofa. Pressing my
chest down low, I once again stuck my arse out for him, he way I knew he
liked it, and waited. He picked up the cane once again and a split second
later I heard the crack of the lexan cane once again breaking skin, and my
buttocks burned with white hot pain.

  I screamed out loud, but it was muffled by the gag, and I flexed and
straightened my knees repeatedly, trying to get rid of the pain. But this
was quickly followed by a second stroke, equally stinging as the one before
it. I squirmed again, taking a while before regaining my composure and
spreading my legs apart, both for more balance and for his viewing
pleasure.

 "Crackkkkkk!"

  "Thwackkkkk!"

  "Crackkkkk!" I counted each terrible stroke in my head, my arse throbbing
as hard as my cock now, my flesh no doubt broken and bruised. The only
consolation would be the strokes that hit squarely against the butt plug
and each time remind me of what was to come soon, punctuated with the plug
forced deeper in my asshole, and sending a strange wave of pleasure into my
spine. As he always did, he timed each stroke perfectly, and now started
paying a lot of attention to the area right between my lower buttcheek and
upper thigh.

  "Crackkkk!"

  I felt like I was about to pass out now. The pain was incredible and I
couldn't hold back the tears. I was groaning, moaning and screaming out
into the gag. Another 3 strokes added to the excruciating pain, as I felt a
few more drops of blood trickle down my welted asscheeks.

  "Crackkkk!"

  "Thwackkkk!' The last stroke landed emphatically once again over the butt
plug, leaving me a trembling, shaking mess at the end of my punishment. Not
daring to move yet, I remained spread wide and bent over on his couch, I
kept my arse up high and waited for his next move.

 I felt his hand yanking me up by the hair again, straightening me up
before turning me towards him. His cock was as hard as mine and throbbing
as well, and I automatically knew what he wanted. I squatted in front of
him, my legs apart and pulled out the gag, opened my mouth again, and took
his cock in deep. Immediately I tried to relax my throat and deep throat
him, feeling his thickness stretching my throat, gagging me as my spit
started to flow freely. Once again he raised one leg up on his sofa and
started to fuck my throat hard and fast. He held my head down hard, his
cock buried all the way and balls deep, till my face and eyes were deep red
and I was struggling for air, before he released me, then continued
facefucking me. It was rough and hard, hardly giving me time to breathe,
but I wanted this man to be pleasured as much as he could be. I sensed he
got quite close to cumming, as he slowed down his pace, fucking my mouth in
long, slow strokes now. I knew what he liked, and slid my tongue over his
shaft as my cheeks hollowed out and I sucked hard, and then took him balls
deep into my throat. I suppressed the gag as my spit ran down the length of
his cock and my chin, and I reached up between his legs, rubbing my fingers
along his asscrack then against the rim of his asshole.

  "Yes that's right, slide it in, boy," he moaned in approval as I
deepthroated him expertly. I slid one finger in, then quickly added a
second easily. I felt him squat lower and wider to get my finger in deep,
as he continued thrusting his hips forward and fucking my mouth. I rubbed
at his prostate as I finger fucked his asshole and once again felt him
getting close. I felt his shaft start to twitch in my mouth, then he
abruptly pulled out, gasping slightly.

  "Fuck, you nearly made me cum, slut." he said as I wiped some of the spit
from my chin, still squatting sluttishly, wide open legged in front of him,
my own cock sticking out, showing off how turned on I was.

  "Get up on my desk boy, then squat down, back facing me," he ordered me.

  I was not sure what he wanted to do next, but I didn't hesitate obeying
him. I got up quickly onto his desk after clearing away some of his papers,
then squat down in the centre.

  "Legs open boy, push your ass out towards me," he said.

  I did as I was told, opening my thighs, feeling the strain as he stood
behind me, watching. I felt him tug at the plug in my ass now.

  "Shit it out, push it our for me," he said, from behind.

  The plug was fairly large and wide, I got up on my tiptoes and started
straining, bearing down. It must have been quite a sight, my asshole
dilating and flexing, trying to expel the large plug in my ass. I grunted a
little as I felt my hole stretch wide, then the plug slowly start to inch
its way out. In a way it felt like I was taking a massive shit, but more
pleasurable. I reached down and stretched my asscheeks apart, trying to
shit the plug out, my hands feeling like a red hot iron on my bruised
flesh. Just as the widest part was about to push past my sphincter, I felt
his hand on the plug, firmly pushing the plug deep in, all the way up
inside me again. The sensation was strange yet extremely intense.

  "Ugghhhh," I grunted, and my cock immediately twitched noticeably. If not
for the cock ring, I was sure I would have blown my load.

  "Now shit it out again boy," the Headmaster said.

  I repeated the action, straining and pushing the plug out, this time more
easily. The widest part was right at my sphincter again and it was starting
to feel really good getting stretched out like that. He then reached down
and held the plug right where it was, not pushing in, but not letting it
pop out either. He held it there, the wide part of the plug keeping me
stretched open and at the same time, I was straining to push it out. It
sent waves of pleasure through my groin and cock, and right at that moment,
he reached around and started stroking me again. I wasn't sure how much
more of this I could take before my cock would burst right through the
ring. Finally, he let go of the plug and I pushed it right out, suddenly
leaving me feeling quite empty.

  I looked down. The plug lay on the table, filthier than before and coated
thickly in shit. I had no doubt what he would want me to do next. He picked
it up and shoved it towards my mouth.

  "Suck this, and clean it up properly, then shit those beads out your ass."

  I opened my mouth, now pretty much used to the strong smell of my own
shit. I suppressed the gag sensation quickly and allowed him to push the
whole plug in my mouth. Its length quickly made me gag and I tried to slide
my tongue around it to clean the muck off its surface. I quickly felt the
dirt come off and fill my mouth and it felt nasty as hell. Hot as hell too,
doing this for the man who just caned me. He pulled out the plug, which was
now only semi-cleaned and waited while I caught my breath. I knew what he
wanted, and looked at him as I closed my mouth and swallowed, retching only
slightly as I felt the bitter shit make its way down my throat. He held the
plug in front of me and I started licking at it, cleaning it as he watched
me and fisted his own cock. I had no doubt he would want to go much further
with regards to scat play as time passed.

  He then pushed the plug back in my mouth and I ran my tongue around it.
Leaving it there, he looked beneath me again, I was still holding my
asscheeks apart and straining hard, trying to expel the large beads from my
asshole, distracted by the task he was having me perform with my mouth.
Grunting, I felt the first bead start to really stretch me and with a
slight tug from him, it popped out and my shitter quickly closed around the
string. He continued pulling lightly but firmly against the string and soon
the second bead was at the entrance of my shitter and I had to keep
straining hard, feeling the stretch. I pushed my buttocks upwards and
backwards slightly to give him better access to the string, and also a
better view. The room started smelling even more strongly of shit and I
knew the beads would be much more heavily soiled than the plug, given they
were lodged much deeper up my rectum. The second bead popped out, and then
followed by the third, each one sending a ripple of pleasure through my
anal passage and it stretched me open deliciously before my sphincter
clenched again.

  I was achingly close to orgasm as the last 2 beads stretched me open and
the string of beads dropped onto the Headmaster's desk, my mouth still
filled with the heady taste and aroma of my own filth. I released one hand
from beneath me and brought it up to the plug, fucking my own mouth,
cleaning it at the same time with my tongue.

  My ass now awkwardly empty and asshole still slightly gaping, I remained
squatting on his desk with the plug still in my mouth. He came up to me
again and I pulled the plug out, now completely clean. Once again, I closed
my mouth and swallowed obediently as he watched me.

  "Good," he said. "Now get back down and back here."

  I clambered off his table just as he reached out and pulled me by the
hair back to the couch. Roughly manhandling me, he pushed me forward.

  "Show me your hole, and open wide," he said as he shoved me onto his
couch, stroking his hard, slick shaft.

  Finally, after all that torment, he would be fucking me with that cock. I
hurriedly bent over, not holding back, and shamelessly spread myself wide
for him. As I had bent over for his cane, I know adopted the same position
for his cock. Naked, bent over, my chest pressed against the cool leather
of his couch, legs apart, wide apart, knees bent, welted arse thrust out
backwards, my hands reaching back, pulling myself open till it hurt.

  I could almost feel his eyes fixated on my shithole, and as a final
silent act of submission, I relaxed and opened up my rosebud for him,
flexing it open, shamelessly. I was up on my toes now, presenting my hole
to him.

  "I don't use condoms boy, you take my cock bareback in your ass," he said
matter-of-factly as he stroked his cock.

  I nodded in reply, "Yes Sir, please fuck my asshole however you want it,
you don't have to use a rubber."

  I was sure my asshole was a mess and shit smeared and slick with spit,
and equally sure I could take him without additional lube. He thought the
same, as I soon felt the tip of his cockhead pressing against my shitter.

  "Open up for me boy" I heard him say.

  I didn't know if it was possible, but I tried to open my hole up some
more, and he eased his cock past my sphincter and in a long steady stroke,
pushing firmly. I moaned out loudly in pure pleasure now as I felt his cock
go in deeper than any other before him, and fill me up deliciously. He
pushed steadily and buried himself balls deep, and I could feel his thighs
against my burning asscheeks. The stimulation was more intense than
anything I'd felt before and I felt my cock stiffen and the cum literally
forcing it's way out.

  "Ugghhhh, fuckkk, Sir, I'm cumming!" I shouted out. I felt my asshole and
cock spasm rhythmically but my cum was kept firmly in place by the tight
cock ring. I'd never felt anything like this before, and it was positively
driving me crazy. Physically I was experiencing orgasm as all the muscles
in my body tightened, but I couldn't spurt my load.

  "Fuckkk.... please, Sir," I croaked in the throes of my climax. "Please
take the ring off, let me cum."

  I couldn't see him, but heard him behind me, "No slut, I get my pleasure
first, you cum only when I allow it."

  With that, he started pumping his cock in and out of my asshole as my
cock throbbed and spasmed. My sphincter rhythmically tightened around his
cock as I came, no doubt intensifying his pleasure as he fucked me, as I
tried to ride out my frustrating dry orgasm. It stung and hurt as his
thighs slapped against my welted asscheeks, but he didn't care, fucking me
deeper and harder. I tried my best to maintain my position, keeping myself
spread wide open, as he sodomised me roughly. I couldn't make out when the
orgasm subsided since I couldn't blow my load, giving me an aching
sensation in my balls as his shaft kept me stretched open and well fucked.
But his steady thrusting and his cock fucking me deep in my ass kept me on
edge. I started moaning out loud, and started thrusting my hips backwards
towards him, timing it with his strokes.

  "MMmmmm, fuck, fuck, fuck me harder," I pleaded.

  Instead of the sharp crack of the cane against my buttocks, the room was
now filled with the sounds of steady slapping of flesh against flesh as he
pounded my ass deep and hard. I wanted to show him I knew how to get my man
off, and I knew how to pleasure someone with my asshole. I tightened up my
hole around his cock, milking him firmly with my sphincter muscles. I would
relax more as he thrusted in deep, then milk him hard as he pulled out.
Before long, he was moaning out loud as well.

  "Fuck, slut, I'm going to cum soon," he said, trying to slow down the
pace. I felt him shudder slightly and his muscles tightened and then he
pulled out his cock, throbbing and twitching, as he breathed hard. He then
walked back towards his desk, opening his drawer again and pulled out a
tube of what seemed like some kind of cream or lube. I was still bent over
and turned to look at him, my eyes glazed over with lust.

  "You don't need any lube, Sir. I'm wide open for you." I said.

  "This isn't lube, boy." he retorted.

  He uncapped the tube, then picked up the soiled anal beads from his desk
and walked back towards me. His cock was visibly shit stained as well, I
could make out as soon as he was back in front of me.

  "Straighten up and suck me clean boy."

  I got up from my bent over position and took his cock back in my mouth,
it wasn't as thickly coated as the butt plug he'd had me clean, and
definitely wasn't as filthy as the string of anal beads he was now
carrying. I made quick work of it, wanting to get back to the real action
quickly, and polished off his shaft and cockhead with a good, few
practised, deep strokes with my mouth, getting him down my throat once
again. He pulled out, satisfied I'd done a good enough job as he cooled
off, and again yanked my head backwards by the hair. I had a good look at
the string of beads now, and I could hardly even recongise them. I'd not
prepared for anal sex prior to this caning and I'd been relatively full
back door, and I hadn't taken any enemas or used any suppositories to clear
out my ass. It was definitely messy. The beds deepest in my ass were
completely covered in my shit, not just smeared, but it looked as if I took
a shit and pushed out a big turd and the beds were buried in it. Even the
fourth and fifth beads were heavily caked in filth. I gulped, not knowing
if I could manage this.

  "Open your mouth boy," the Headmaster snarled. He remained as hard as
ever, and he didn't flinch at the smell of the beads, as he lifted them up
over my open mouth. I gagged a little as the heavy smell hit my nostrils
hard, and he placed the first bead, or at least what was visible of it, and
the large piece of shit right in my mouth. I closed my lips around it and
immediately my mouth was completely filled with my own turd and the large
bead. The smell was heavy and slightly overpowering and I retched two or
three times, nearly throwing up. Having such a large piece in my mouth was
vastly different from doing dirty ass to mouth or cleaning a soiled butt
plug from my asshole. He let go off the string of beads and let the other
four dangle outside of my mouth.

 He then squeezed the content of the uncapped tube in his palm. It was a
white cream like substance, and he squeezed a good liberal amount out, then
lathered his cock with it, spreading it and stroking it along his massive
shaft.

  "This isn't lube, slut. This is a desensitising cream. Numbs my dick a
bit when hot sluts like you are making me cum too soon, so I can fuck your
asshole for longer." he said to me, fisting his cock and covering it with
the cream. It soon turned colourless after a good few strokes, and he added
some more, pumping his cock again after.

  "Mmmmphhh," I mumbled like a fool with the anal beads still in my mouth.

  He squatted a little with his legs apart and squeezed some more cream in
his palm, then reached down and slathered it into his asscrack and pushed
some in his asshole with his finger. I watched his cock twitch as he did
this.

  The stench and heavy aroma around my face and mouth was quite intense,
and I reached up to pull the bead out of my mouth, then took a breath of
fresh air, and lowered it back in. I slowly bit off a large part of the
turd and pulled the bead out again. I was seriously gagging now, and looked
pleadingly at the Headmaster who was still masturbating himself whole
watching me.

  "I don't expect you to clean the whole string and swallow everything boy,
but you will do as you say. If you want to be my boycunt and cane slut long
term, I'm going to expect you to be on the receiving end of some heavy scat
play with me. Now start chewing, and I want you to swallow it," he ordered.
He must have known that by now, I would do anything for him.

  I dared not disobey, knowing full well he could pick up the cane anytime
and go to work again on my tortured buttocks. I started chewing on the big
piece of shit in my mouth and immediately the taste and smell intensified
heavily. I retched hard and felt my stomach heave, nearly throwing up, but
I kept it suppressed. The whole experience felt both surreal but incredibly
arousing. I'd been very submissive as soon as I started fucking, but this
crossed a new level of submissiveness for me. In my mind, I'd thought there
was nothing as submissive as chewing and eating my own shit fresh from my
ass, cleaning my own shit off the cock of the man who would be fucking and
cumming inside my asshole. I wanted to his bitch and scat slut, and I
wanted to start now. I was squatting down now, as I was previously, and as
much as the stench stung at my nostrils and in my mouth, I was extremely
turned on. I spread my thighs and reached down to pump my cock. It was
hard, slick, still wrapped tightly by the cock ring, and I shamelessly
masturbated, my mouth full of my own shit.

  I retched again, as I chewed, and the acrid shit started to sting a bit
on the insides of my mouth. But I was horny, definitely very very horny. I
picked up the string of beads again and lifted it to my mouth. There was
plenty more shit thickly caked over and covering the beads. I opened my
mouth and but off another large piece, adding it to the big load already in
my mouth.

  "Very, very good, boy, you are learning fast. Definitely the biggest slut
I've had from this school so far," he said, as he continued leisurely
masturbating himself.

  My stomach heaved as the taste intensified with this second load. I felt
that I was getting more used to the heavy earthy taste now, and started
salivating quite heavily, involuntarily. I chewed more and realised my
mouth was really really full and my cheeks were slightly bulging. I closed
my eyes and swirled my tongue around in my mouth, chewing some more. I
looked deep into the Headmaster's eyes and slowly swallowed once. At least
half went straight down my throat. I could literally feel my bile
immediately rise up, and had a wave of an uncontrollable urge to vomit.
Despite my arousal, my stomach heaved violently and I let out a loud
sickening retch, fully expecting a torrent of shit to pour out my mouth,
but somehow, I managed to keep it down. My eyes were bloodshot now and
tears ran down my cheeks. There was still a big load in my mouth but the
Headmaster showed me his approval as his cock seemed to get even more
erect, his fist continuing to pump it.

  I knew what he wanted me to do, and I continued chewing at the foul
tasting shit in my mouth. I kept masturbating, wanting to keep myself on
edge and aroused. I slipped a finger down, in between my cheeks and stated
rubbing at my anal ring, then penetrated myself again and started pressing
at my own prostate to keep me hard. Bracing myself, I looked at the
Headmaster again and clamped my lips shut, suppressed my gag reflex as best
as I could and swallowed hard. The second time, it went down much easier
than the first, and though I retched still, I wasn't anywhere near as I was
just now to vomitting. The entire remaining load went straight down and I
kept it down, my stomach heaving only slightly. I then opened my mouth and
showed him that it was completely empty, though I'm sure it was still
deeply brown stained.

  "Very good, cunt. I'm impressed enough. Do you want to eat straight from
my asshole after I train you to, boy?" he asked

  I didn't hesitate and nodded my head, "Yes, Sir, I want you to feed me
your shit and I want to eat it all."

  I couldn't imagine how far this caning had gone, and that I'd just
swallowed a big load of my own shit in front of another man. He pulled me
up by the hair and pushed me back onto the couch.

  "Lie down boy, on your back. I'm going to reward you." he said.

  I settled back down, and laid down on the sofa, as I saw him reach down
for the now clean buttplug that had most recently been deep inside my ass,
and then straddle me, his groin and cock close to my face. I opened my
mouth, as he spread his legs wider for balance, and he squatted down low so
I could suck him easily. He slid his cock right in and I started sucking
him. He thrusted only slowly, sliding his cock with long, leisurely strokes
all the way in, then pulled out till only my lips were wrapped around his
cockhead. He rocked his hips gently back and forth, and it almost felt like
a lover gently fucking my mouth and throat, not a rough, dominating,
raunchy scat top.

  He placed the butt plug in my hand, the flange against my palm as he
stroked his cock in and out of my mouth. I felt him shift a little and
realised he was spreading his thighs wider apart.

  "Push the plug into my asshole, all the way in, and stretch me out," he
said lustily.

  He continued pumping his cock slowly in and out of my mouth, and he
reached back to spread his cheeks apart for me. I was still trying to
orally pleasure him so I fumbled a bit with the plug. I stopped for awhile,
realising the plug was quite dry now, so I put it in my mouth, fucking it,
getting it wet, then spit more on the tip. He leaned forward a bit to give
me better access, and at the same time, slipped his cock back into my wet,
hungry mouth. I slid the plug along his asscrack, and felt him shudder
slightly as the tip brushed against his shitter. I adjusted my hand and
tilted the plug till it was at the proper angle and started applying
pressure.

  "Uggghhh," he grunted.

  He relaxed his sphincter and I felt the give as his asshole allowed the
plug entry. I pressed firmly and he relaxed enough as the plug inched its
way up his ass. I figured that having a plug up his asshole would intensify
the pleasure he felt when he fucked my mouth, and later, my ass. Slowly,
the widest part passed his tight ring, and he grunted as it popped past,
the rest of the plug sliding home, lodged fully inside him.

  Feeling the plug all the way in now, he relased his hold on his asscheeks
and reached down to hold the back of my head with both hands, then started
thrusting harder into my mouth, fucking my skull as he did earlier. I
struggled a bit now as his rhythmn quickened, and tried to relax my throat
as I knew he wanted.

  He started panting a bit as the sensations intensified, then stopped, and
pulled his cock out, which was followed by a long string of spit, and me
gasping desperately for air. He reached out for the tube of desensiting
cream as he got off me, and squeezed out more on his palm, and slathered it
over his cock. He lay back on the floor now, and stroked his hard cock.

  "Get down here, ride my cock, slut," he commanded.

  I clambered off the couch, gathering up the slobber and spit with my
hand, and as I spread my legs to squat ove his hard cock, reached between
my legs and lubricated my hole some more. His cock looked absolutely
menacing, standing straight up, swollen cockhead, throbbing, veiny and
immensely thick. I faced towards his feet, spreading my legs apart on
either side of his thighs, and slowly squatted down, my own cock still tock
hard and bound firmly. I reached down and guided his cock towards my
asshole as I lowered myself down to him. Though relatively loosened now
after all the penetration, his cockhead still felt huge pressing against my
shitter. I relaxed my hole and opened it up, slowly allowing this cock to
penetrate me. I spread my thighs wider open as I moaned in pleasure.

  "Ohhhh, fuck, that feels good," I sighed.

  Slowly I sank my hips lower as I engulfed his entire length with my
practised, well fucked asshole, till he was balls deep in my ass. Feeling
absolutely full, with his cock packing my shit in deep, I started to slowly
fuck myself on his cock. Once again, I wanted to show him that I knew how
to pleasure man-cock with my asshole, and built a slow, steady rhythmn. I
would tighten my asshole hard and squeeze and milk his shaft on each
upstroke as I raised my hips up, till just his cockhead was inside me, then
relax my hole before plunging it all the way in again. After a few strokes,
I felt very close to orgasm again, once again prevented by the cock ring
wrapped tightly around my shaft and balls. I slowed down a little, and got
up on my toes so I could work my hips down lower. He moaned and so did I,
and he started thrusting his hips upwards in unison with me pushing
downwards. I bent slightly forward and rested my hands on his thighs,
feeling my body shudder with pleasure as I sluttishly worked his cock with
m anal muscles.

  Undoubtedly, I knew he would be having an excellent view. He could have a
good look at his handiwork with the cane, my buttocks undoubtedly welted
and still very much stinging with pain each time he reached out to grab and
asscheek. And I'm sure he could see how wide my thighs were spread apart
and my asshole wrapped around his cock. I reached back and spread my
asscheeks for him as I fucked myself on his cock, so he could get an even
better view of his cock sodomising my horny, dirty shithole.

  "Tighten your hole more, slut," he said. "And when you push down on my
cock I want you to bear down like your taking a shit. I want you to push
that shit out, shit on my cock."

  "Fuck, that's hot Sir." I replied.

  I leaned forward again, my hands still spreading my asscheeks open, and
tightened my assring harder as I pulled upwards, milking his cock for all I
was worth. Then as I was pushing down, paused awhile and started bearing
down with my shitting muscles, relaxing as if I was taking a shit. I could
feel the shit move down lower in my rectum, and coating his cock in a thick
layer of filth. At the same time, I fucked down low and engulfed his cock
fully. I repeated this again and again, squeezing hard as I pulled out,
then shitting down oon his cock and I pushed down. After awhile, I could
feel the shit leaking from the rim of my ass, freely flowing down his cock
now. The smell filled the room quickly as I continued impaling myself on
his cock.

  I decided to give him a treat. I pulled up, his cockhead just inside my
anal ring, and I kept it there for a bit, then grunted as I strained hard,
up on my toes, taking a shit right there on his cock. My asshole
relaxed, my fingers still pulling my cheeks open, and the shit slowly
flowed out, first coating his cockhead, then squeezing out from between my
anal ring and his shaft, and slowly inched it's way down, further coating
his already heavily soiled cock. It felt immensely nasty, and dirty, and
ultimately I knew I would be swallowing all of it.

  "Very nice, boy," the Headmaster said.

  I pushed and squeezed my shitting muscles some more, as more of my filth
flowed out, till the smell got too overpowering. Then I lifted my hips and
squeezed my shithole closed, releasing my cheeks and turning around. The
results of my efforts were far messier than what I'd expected in my mind.
There were a few clumps of my shit over his groin the entire shaft of his
cock was completely caked in a thick layer of my filth. HIs cockhead was
thickly smeared and covered in shit and the smell hit my nostrils
immediately even from a distance. He lifted both his legs up and backwards
and held them apart, his knees bent and hands pulling them back. I had a
good look at how filthy it had gotten, my shit even completely covering his
balls and hard flowed downwards even over the flange of the plug sticking
out his asshole.

  "Clean up, boy. Start with the plug, then lick my cock and balls clean."
he ordered.

  I got down on all fours in front of him and bent forward, between his
wide apread thighs, my ass sticking up high. The smell was even stronger
here, but after eating and swallowing and the intense scat play earlier, I
found this much more tolerable. Besides, I was feeling hornier than ever. I
used one hand to pull one asscheek to the side then started licking at the
filth on his balls, and flicking the shit on the buttplug with my tongue,
into my mouth. I could hear him moan in pleasure as he held his legs open
and I performed a good cleanup. I swallowed quickly, in small amounts,
sliding my tongue over his balls, and taking them each into my mouth,
sucking and cleaning them till the thick layer of shit was gone. I tried to
hold some of the shit in my mouth, and swallowed the rest as I worked at
cleaning up. Looking up from between his thighs, I looked at him in and
swallowed hard. This time it was much easier and I could swallow these
small amounts without any difficulty or any retching.

  Then I moved upwards, his balls now clean, and started working on his
cockhead. The smell here was much stronger as I had pushed a fairly large
amount of my shit onto his cockhead.

  I looked him the eye and asked him, "May I suck your cock clean, Sir."

  "Go ahead, slut, put it in your mouth." he replied.

  There was nothing more submissive than asking permission to suck your own
shit off the cock that had just been fucking your asshole, I thought. I
opened my mouth and tried to put his filthy cockhead in my mouth but
immediately gagged from the smell. The layer of shit was very thick and my
mouth immediately was with with the earthy and bitter taste of my own shit.
I struggled slightly to get it in and wrapped my lips around it, then used
my tongue to flick at and scrape the shit off his cockhead, coating my
tongue in a layer of foul smelling, bitter filth. I retched again, but
forced myself to kep going at the task. Once I felt my mouth was pretty
full, I stopped and looked at him and started chewing a bit, then held back
to urge to vomit and swallowed as he watched. It was intense and I felt my
eyes water, and the skin around my lips start to sting a bit. I kept the
shit down in my stomach and went back to work immediately. There was
considerably less shit coating his cockhead now though it was still thickly
covered, and again I placed my mouth over it and continued my shitty
blowjob. I ran my tongue around the whole surface of it and allowed a good
amount of spit to flow freely around his cock.

  The smell in the room now was incredibly heavy as I remained bent over,
sucking on his shit covered cock, as the Headmaster held his legs apart.
"Reach down and start pushing the plug in and out while you suck boy," he
said from above. "Don't pull it all the way out, just halfway, fuck me with
it."

  I reached down and did as he said, pulling against the flange and
stretching his hole slightly as I pulled it halfway out, then pushed it in
again. I continued sucking on him at the same time, my mouth and cheeks
slowly filling with more of my filth, before I felt that his cockhead was
more or less clean now. I came up for air, and pulled his cock out my
mouth. His cockhead was more or less clean now, just smaller bits and
streaks here and there, but my mouth was absolutely full of my filth, a
considerably larger amount than the first one, and the smell and taste very
strong. I was slowly pulling out and fucking inwards with the buttplug, and
I braced myself as I looked at him and swallowed. The wave of nausea
immediately wracked my stomach with a huge heave and my throat clenched and
squeezed, I turned to the side and nearly barfed out everything but once
again, managed to keep everything in my stomach as the bitter, acrid load
travelled the length of my gullet.

  He spread his thighs apart wider, moaning with lust both at the
stimulation from the butt plug moving in and out of his asshole, as well as
the vulgar, shameless display of shit- swallowing his new slut was putting
up. I bent forward now and, with much less obstruction now, engulfed his
cockhead with my lips and mouth and started another sloppy blowjob. There
was still a fairly considerable amount of shit covering his shaft but
lesser than what I had already swallowed, so I built up my rhythmn quickly,
using my tongue to clean him and my throat to fuck his cock. I bobbed my
head energetically back and forth and kept the plug fucking his asshole
firmly. I swallowed as I went along, the mixture of my spit and shit
running down my throat, with help from his cock that was fucking my throat.

  I'm sure the desensitising cream had been doing it's job, and she showed
no sign of being any closer to an orgasm after I had been working on his
cock and shithole vigorously for 15 minutes. The sounds of my disgusting,
squelching blowjob echoed through the room. I then stopped pushing the plug
and briefly came up for air. I looked at his cock, marvelling at how
different it looked compared with it when it just came out my ass. It was
shining in my spit, completely wet and slick, still impossibly hard, and
there was no sign of shit on it's shaft, I'd swallowed the remainder as I
was sucking him off. The only sign left of our filthy scat play were the
clumps of shit left on his groin, which were now slightly smeared around.

  "Fuck, you're a very good cocksucker boy," he growled. "Grab that towel,
towel my cock off and get that tube of cream, I want to fuck that shithole
of yours."

  I did as I was told, and grabbed the towel, drying off the spit from his
cock, and picked up the tube of desensitising cream.

  "Go on," he said. "There is still quite a bit left in there, and I have
plenty more tubes. Squeeze out the remainder and cover my cock with it."

  I swallowed, thinking about how long more he would last with this much
cream numbing his cock, but didn't dare disobey. I squeezed out a liberal
amount in my right palm and wrapped my fingers round his cock, wanking him
and giving it a good rub, working down to his balls as well. Then I
squeezed out the remainder and continued the handjob, covering his cock
well with the cream. I tossed the tube aside, now waiting for his next
move.

  "Ride me boy, this time face me. Squat that asshole over my cock." he
ordered again.

 I got up and straddled him once again, and opened up my legs. My cock was
still throbbing with arousal and anticipation, still bound tighly by the
leather ring, and I slowly lowered myself again on his cock. My asshole had
tightened considerably by now and with his cock dryer than before, I had to
strain a bit a get up on my tiptoes, grunting and really traying to flex my
butthole open as he pushed his cockhead into my bowels again. My sphincter
finally relented and he entered me with a pop. I leaned back with my legs
apart and braced my palms against the floor and slowly started bearing down
and allowing him all the way up my bowels. All the way as he worked his way
in, my cock twitched lewdly in front of him as he fucked me.

  "Fuck, you asian boys are all sluts, and you're the biggest one," he
said. "And that's saying a lot."

  "I've fucked a lot of you horny schoolboys after 5 years at this school,"
he continued. "You know how many?" he asked.

  I shook my head, my mouth and tongue numb with lust and from all the shit
swallowing, and my body covered in sweat as I slowly started fucking my
tightened asshole up and down his massive prick.

  "Twenty-seven, boy," he said. "And only eight of them have since
graduated. So you imagine I get to fuck a lot of ass here every week."

  I was sure that he would have fucked other boys from the school, given
that I knew that there were definitely a few others I knew who immensely
enjoyed canings, but twenty-seven seemed like a pretty large number to me.

  "I've never used a single condom and in fact I dished out an extra 15
strokes on the boy who asked me to use one. He's taken me bareback each and
every time since. I make sure I cum in each one of their tight assholes
too. And the same goes for you." he said.

  I was dizzy with lust hearing him talk trash like that, wondering if I
knew any of these other boys he was caning and having sex with. I slowly
built up the pace, my asshole stretching comfortably now with the girth of
his cock up inside me. I leaned back and rocked my hips up and down,
gripping his hard cock with my practised anal muscles, my own erect prick
bouncing obsecenely in front of him. We were both rapt with pure sexual
pleasure now, and I moaned out loudly. He then leaned forward and wrapped
his fingers around my cock and started pumping his fist, jerking me off as
I fucked myself on his shaft.

  His cock deep up my ass, rubbing my prostate, and his hand wrapped around
my cock, stroking me off, sent waves of pleasure through my body and up my
spine. I kept up the pace, my body and hips bouncing up and down, slapping
against his thighs as I started fucking myself harder, with my thighs still
spread wide open.

  "Uhh, Ughhhhh, fuck, I'm going to cum soon. Please let me cum, Sir," I
begged. I could literally feel a new load of boiling cum start to swell up
my shaft and balls, trying to push past the tight ring wrapped around my
cock to keep it from spurting. My anal muscles started spasming and
clenching around his cock, my orgasm impending. I knew this would be an
equally giant load.

  He sensed my huge orgasm about to tip me over, as my eyes started rolling
back and my back and thighs started trembling, and my sphincter
rhythmically pulsating and gripping at his shaft. He then let go of my cock
and reached out to steady my hips, stopping me from fucking myself further.
Then he started sitting up, all while still keeping his cock lodged deep in
my shitter, then reached forward with both hands and held he by the hips.
He was well built and undoubtedly strong, and he started standing up,
lifting me with him. I reached forward and held onto his shoulders as he
lifted me off the ground, then he let me lean back and lay me back down on
the sofa.

  He roughly manhandled me now, using both his hands to hook them behind my
knees and push them all the way back till I was folded in half. I was quite
flexible and allowed him to push my legs back all the way. He splayed them
apart and pressed them down hard, till my thighs were nearly pressed
against the sofa.

  "You want to cum, boy?" he growled.

  "Fuck, yes! Please let me cum for you Sir!" I cried out loudly.

  I reached down and pulled my asscheeks apart, though I probably didn't
need to do so since I was already so spread eagled. He leaned forward and
leaned his weight into me, grinding his hips down, keeping me spread open
with his hands, then started really hammering me hard. His strokes were
hard, authoritative and forceful, he rammed hard into me, going balls deep
with each stroke, and pulled out nearly completely before plunging again
all the way. Each drive nearly knocking the wind out of me.

  "Uggh, fuck, fuck, Ugggh." I grunted repeatedly as he fucked me hard. My
body was jolted and my cock flailed around with each stroke. His thick,
massive shaft rubbed against my prostate, stimulating me, driving me closer
and closer to my orgasm.

  "Fuck, boy, tighten up your hole, I want to feel that shithole grabbing
my cock," he grunted.

  I tried not to relax my hole so much as he fucked me, instead tightening
it as much as I could. I leaned my head back and closed my eyes as my
orgasm approached. I started shuddering again, my back now arched up high,
and my sphincter muscles once again started spasming hard, gripping his
cock even tighter like a vice. I tried to keep still, my breathing shallow
and rapid, and my body flushed and covered in a sheen of sweat, building up
to my biggest cum yet. My cock twitched and spasmed in readiness to spew
its load.

  The Headmaster could see this, and he reached down and started releasing
the tight leather cock ring. Even before it was released fully, a steady,
heavy stream of thick cum started flowing out freely, a result of my
earlier pent up orgasm that was kept in check by the leather cock ring. He
thrusted even harder, and it instantly pushed me over the edge right as the
cock ring was fully released.

  "Oooohhhhhh, fuuuuccccckkkkkkk! I'm cummminnnggg!" I yelled out.

  My toes curled and I straightened out my legs while still folded in half,
spread eagled. I wasn't even touching my cock, and I released my grip on my
asscheeks, instead trying to grip at the sofa as the biggest orgasm I'd
ever felt rushed through my body, making me flop and spasm uncontrollably.
My cock absolutely erupted with a fountain of cum spewing hard and spraying
me with ropes of cum right over my face and my open mouth. My asshole
spasmed hard around his cock as he continued thrusting and fucking me,
watching as my body jerked as I came hard and violently.

  "Fuckkk, shitt...." I mumbled, hardly managing to even form the words.

  I couldn't understand where all that cum was coming from, after already
having 3 hard orgasms, but it continued spewing. My cock spasmed and shot
thick ropes of cum over my own chest and face. The Headmaster continued
holding my legs apart and vigorously continued thrusting his cock deep and
repeatedly in my shitter as I came hard. He showed no sign of letting up,
no doubt the cream helping a lot with his staying power. He reached down
with one hand and stroked my pulsating cock as it continued to cum hard,
and I moaned as my balls ached deeply.

  I rasped with short, shallow breaths, my whole body responding to the
orgasm, and I slowly regained some composure after a minute or two. All the
while, he remained inside my asshole, pounding me hard and mercilessly. I
swallowed hard, my mouth still a numb pit of fetid bad breath, and kept my
legs open. Finally, I started coming down from my orgasm, my face, chest
and stomach a mess, ropes of cum splattered all over. My asshole relaxed a
bit more, and I started to feel very aware of the Headmaster still pounding
away.

  His thrusts were deep and hard, bottoming out each time, and he
straightened up a bit, Still keeping my legs apart, he pulled out his dick
completely, and I suddenly felt very empty, my asshole no doubt gaping
widely open.

  "Fuck, you should look at yourself boy, your hole is wide open," he
groaned, and reached down to spread my asscheeks with his hands.

  He then aimed his cock at my hole again and pushed it back in just as my
shitter started clenching up more. The fucking continued at a furious pace,
my body being thrown backwards with the force of each thrust from his hips.
I started tightening my hole again, squeezing his cock as hard as I could,
as I looked up at him. He was covered in sweat as well, his body deep in
exertion, breathing hard. Judging by the pace he was going, I knew he was
far from close, but I'd started feeling a deep pleasurable sensation
centred deep in my asshole and spreading through my groin and cock.

  I'd softened considerably after cumming hard, but I reached down and
started stroking myself to hardness again. My eyes were rolled back in
pleasure, and I felt myself slowly getting hard again. He kept up the
fucking like that for a good 15 minutes, till I was noticeably erect again,
then he reached down and pulled me upwards by the hair, and pulled his cock
out of my gaping asshole.

  "Bend over, I'm going to fuck you doggy," he ordered.

  Eager as ever, I got up and got into my favorite position again. Bending
over, splaying my thighs and feet apart, and pushing my arse out, opening
my asscheeks wide with my hands, showing him my well fucked boyhole. He
grabbed onto my waist and pushed home quickly again. I grunted out loudly
as I felt him penetrate me roughly. He thrusted just as hard, fucking me in
my violated asshole as he would any street side hooker. I was slowly being
driven over the edge again by the constant stimulation. I was hard again
and breathing hard, panting. Each time he drove inwards with his cock, my
face was pushed hard into the sofa. My cock throbbed as the minutes passed.
Another 10 minutes, 15 minutes, his fucking was relentless, his stamina in
top form. The room was filled with the sounds of his flesh slapping against
mine, and both our grunts and loud moans.

  He then pulled out again, and quickly sat back on the sofa, fisting his
cock as he sat looking at me, still bent over, breathing hard. I quickly
got up and straddled his cock, facing him, thighs apart and cock erect, and
impaled my shithole once again on his massive shaft. I knew I could control
the pace better like this and placed my hands on his chest as I rode him
more slowly, taking more time with each stroke. Once again, I gripped his
cock tightly with my anal muscles each time I pushed up, milking him hard,
then realxed my hole more as I sat back down. We looked at each other, both
of us breathing hard, and I realised how good his thick cock was making me
feel. He was extremely hard and his cock sprang back flush against his
stomach each time I pulled out. And each time I put it back in to ride him,
his cock rubbed against my prostate as I fucked myself on it, sending waves
of pleasure through me.

  I decided to give him some oral, ass to mouth action, as my asshole
started to feel a little sore from all the fucking. I would ride him for a
good 5 minutes, milking his cock, then get off, and squat in between his
legs, and take him fully in my mouth and throat, giving him a sloppy, wet
deep throat. Suck him for another 5 minutes, then get up and ride him deep
in my shitter again. I was started to get tired but I stayed horny as ever.

  He would moan his approval as I alternated between sucking and riding
him. I must have fucked him like that for another good 20 minutes, and was
now riding him, my thighs splayed open, my hard cock bouncing around, my
hands on his chest and I found myself again breathing hard, my orgasm
close.

  "Oh fuckk.... Sir, I'm cumming again," he cried out, as I felt my cock
start to twitch and spasm.

  "Cum for me boy, cum hard." he said, holding me by my hips.

  I slowed down a bit, and wanted to really enjoy the penetration as I
came. I tightened as hard as I could as I slowly pulled up, then squatted
low as I could go as I pushed down. I felt my breathing turn ragged, and
without touching my cock, a few deep thrusts deep in my ass brought me to
my fifth orgasm of the night. I gulped and shuddered, and spasmed as he
held me firmly by the waist, pulling me all the way down till he was balls
deep up my shithole, and watched as I came.

  My eyes rolled back again and my asshole again milked his cock as I came
hard. My cock spasmed but not much cum was coming out, after the previous
four huge orgasms. The sensations though were not any less pleasurable as I
felt warm and flushed all over as I tried to ride out my orgasm with him
buried deep in my ass. The small amount of clear cum shit from my peehole,
and slowly ran down my cock, which was still absolutely erect and pointing
staright up.

  I tried to compose myself, and felt him starting to thrust again, and he
moved me with his hands on my waist, slowly starting to fuck me again. I
didn't know how much more fucking I could take. My asshole was very well
fucked by now, slightly aching and wide open. My cock and balls were really
aching now, after all the action, and I was in wonder how he could keep
staying hard and fucking me all this while. But I knew I wanted to pleasure
my new stud and get him to get his rocks off and shoot his load.

  He made me continue riding him, and I obeyed. The fucking continued as I
rode him cowgirl, then doggy again, then missonary with my legs foled back
again, then back to cowgirl again. I was so far gone now, totally spent,
sweaty, horny, cock drunk and needing his cum load and quickly. I was
panting again, I was hard again, and I was riding him hard. I could tell he
was definitely getting very close now. His cock was deep in me, and I was
milking him with my tightening ass muscles as hard as I could. My thighs
spread and my cock sluttishly on display again, I reached down to wank
myself as I rode him. I knew his load would be huge as he'd held back for
so long, and before long I felt him tighten his grip on my waist and sit up
a bit more.

  I slowed a bit, and renewed my grip on his cock with my anal ring, I
spread my thighs even wider and fisted my cock slowly. My ass muscles now
as tight as I cold get them, I slowly pulled upwards now, raising my hips
up, then slowly as I had started, I kept my ring tight and squatted back
down fully on his cock. I repeated this once, twice, thrice, and I finally
felt his cock twitch hard inside my ass. I quickly buried him all the way
in.

  He shouted out loud as he reached both hands down to squeeze and pull my
asscheeks open wide, sending a wave of pain through me as they were still
very much welted.

  "Fuckkk..... I'm going to cum!" he cried out.

  "Cum inside me, cum inside my ass," I barely managed to say.

  His cock spasming and jerking and my own hand around my cock pushed me
over the edge right at that second too. We both reached a huge climax, his
being much bigger than mine, at the same time. My cock again spasmed, but
my orgasm was totally dry now, I was completely spent. Six delicious
orgasms, I couldn't believe it, I thought to myself as I shuddered. I could
feel his cock literally erupt a huge load of scalding hot cum deep into my
bowels, my sphincter contracting rhythmically around his cock, no doubt
intensifying his pleasure as he came and emptied his balls into my shit
tunnel.

  I felt his cock pump again and again, sending his seed into my ass, deep
inside it.

  "Fuck, that feels great. Knock me up Sir, make me pregnant with your
cum," I said lustily, trash talking him as he rode out his orgasm.

  He continually came and shot cum deep up my asshole for well over a
minute, breathing hard as I tried to keep all his cum deep inside me. I
kept my anal muscles tight and warpped around him pulsing shaft, my legs
were still spread wide and my hands on his chest. He was still pulling at
my cheeks hard with his hands, and I stayed still, letting him cum as much
as he wanted, bareback, inside my asshole. My orgasm was long over by now,
but all I wanted was for my stud to get as much pleasure as he could.

  Finally, I felt his breathing start to normalise and slow down, and his
cock stop throbbing. His eyes were closed and he was no doubt as satisfied
as he could ever be. All the while, I remained still, keeping my anus
tightly wrapped aorund his cock and my thighs spread apart. I was finally
soft, the first time a few hours, and I knew what I wanted to do for him to
round up our session.

  "I hope you enjoyed that as much as I did Sir," I said as he opened his
eyes.

  "Fuck, that was amazing, slut. I've never cum so hard in my life," he
replied, smiling a bit.

  "I want to show you something, Sir, you just sit back now." I said,
teasingly as I pushed my hand off his muscular sweaty pecs.

  Slowly, keeping my anal muscles tight like a vice, I lifted my hips off
his thighs, his rapidly softening cock sliding out of me very slowly. Just
as I felt his cockhead about to pop out, I clenched my asshole as tight as
I could and pulled his cock out, my ring shutting down tight as he cock
left my bowels. I felt absolutely full of cum, and I could feel it almost
swirling about inside my shit tunnel as I got up off him and cleared a
small area on a non carpeted area in front of him. I turned around so my
back was facing him, and slowly, I spread my legs apart, wide apart. I
reached behind myself and once again spread my welted cheeks apart for him,
putting on a nice show, and realised I was not hard. I wanted to show him I
was turned on, and I wanted to show him my cock was hard as I performed for
him, so I used one hand to slowly jerk myself off, trying to stroke myself
quickly to hardness. I closed my eyes and revisited the lewd, pornographic
images of the intense session we just had and my erection was quick to
come. I felt my shaft quickly stiffen and point straight up. and I released
it, bringing my hand back to once again spread my cheeks open.

  "I'm hard for you Sir, I want you to enjoy watching this." I said.

  I stretched my asscheeks as wide as I could, and showed off my hole,
which he had just spent more than an hour violating and penetrating. I was
sure it would have been pretty swollen and still pouting even though I'd
clenched it tight, keeping his cum inside me. Slowly I squatted down,
getting down low in a wide open legged squat, showing off my hole, my cock
once again throbbing. I felt his cum start to leak out my asshole, and I
slowly relaxed my shitter.

  I couldn't imagine how much he had shot off inside me, but the flow was
incredible. An immediate torrent of warm thick cum started flowing straight
out my asshole onto the floor. I looked down between my legs and was
shocked how much there was. I quickly got up on my toes as the cum flowed
freely out. It was shot so far up inside me, it was stained a deep brown as
it flowed from my asshole. It was followed by disgusting wet farts as the
flow slowly started to slow down and I continued pushing it out. I reached
under me to slip 2 fingers deep up my asshole to try to dig more of his cum
out of me. It was a nasty and disgusting display of whorishness that
immensely turned me on. I looked behind me and saw that he was stroking his
cock again, as he watched me.
  There was now a pretty big pool of cum below me, and I flexed and pushed
my asshole out, getting the last bit of it out of me and onto the floor.
The fucking had push my shit down pretty low as well, and as I shitted out
his cum, a few pieces of my own shit squeezed out of my hole onto the floor
as well. The smell, was once again, overpowering.

  I pumped my cock for a few more strokes with my hand to keep myself hard,
then straightened up and turned around. I looked down at the floor beneath
me. It was an absolute mess. A large puddle of cum lay there, most of it a
deep brown, but areas of white were still seen, and a few small to
moderately sized clumps of shit as well. I slowly got down on all fours,
and bent my head forwards. I'd never done anything as nasty as what I was
about to do, but I was dizzy with lust. I stuck out my tongue and slowly
started lapping at the big pool of cum, it tasted heavily of both cum and
shit. I looked at him as I did so, flicking his shitty cum into my mouth as
I did so. Once I felt I'd got a decent load inside my mouth, I opened my
mouth to show him what was inside it, and swallowed it all, feeling it go
down my throat to my stomach.

  "Fuck.... you're nasty, boy. Eat it all, don't waste it" he growled as he
pumped his dick, watching me.

  I was spurred on knowing that he was enjoying the show, and continued
lapping at the cum over the floor, stopping and swallowing as I went along.
It took me 7 or 8 times, but finally I'd gotten the last bit of cum in my
mouth. The taste was absolutely nasty, but compared to what I had eaten
earlier, it didn't cause any problems when I swallowed. I kept all of down.

  I looked at him, totally spent, sweaty, naked, totally used, humiliated,
and well-fucked, his newest cane slut, and wondered what was next for us.

  "Very good, boy. It's getting late now. You can clean up here and get
dressed." he said.

  "You can give a call home if you want, tell your folks you won't be
coming home tonight. You can spend the night at my place." he winked as he
stood up, walking away.