Date: Sat, 7 Nov 2009 14:21:18 +0000
From: Jake Scott <sexy.arse.man@live.com>
Subject: Persistent Bottom

All characters are above the legal age of consent in their jurisdiction.


Persistent Bottom


I had been put in detention for what the headteacher said was, quote,
"Persistent slutty behaviour". Mr Gilbert was a sour, dour old fat man who
was balding and sported an ugly grey unkempt beard above his ample no
doubt, pork filled belly. How he ever managed to convince the board of
governors that he should become headteacher I should never know.

I went to a posh and exclusive all boys boarding school in Buckinghamshire,
thanks I guess to my father being a bigwig expat banker over in
Singapore. Obviously Singapore was good enough for him and my mother but
not for little old me, for they had shipped me off to this school in the
country to in their minds no doubt 'become a man'. If they knew what was
really going on, they might perhaps have thought twice.

In a boarding school of this nature, homosexual behaviour is not exactly
rare. It's the old prison hypothesis... young men deprived of women will
find other creative ways to fulfill the desires in their loins. So it was
that a prefect had ended up taking a shine to me and one day after we had
had an afternoon of games, he had pulled me aside while I was still in my
rugby shirt and shorts and asked me whether I wanted to have a smoke with
him. I didn't really smoke at that time, but I said OK anyway, more out of
curiosity than anything, and he took me off away from the group behind the
bike sheds which were in a building detched from the main school which
housed the changing rooms.

He had sparked a cigarette and he made idle chat as he dragged on it,
finally giving it to me to try. I had taken brief drags on other people's
fags before but never had a whole cigarette to myself. My head got a little
light after taking a few too many puffs too quickly. The prefect had just
chortled to himself and put his arm round me, telling me to slow down. It
was then that his hand found its way down my back and onto my bottom. To my
surprise he left it there and seemed very interested in it. He told me to
turn round so he could see it a little better. He seemed pleased, groaning
a little bit to himself. He then told me to undo the tied waist band so
that he could pull my shorts down a little. I did, and he pulled my white
shorts down so that he could see my pink round arse more clearly. Then he
bent down and to my surprise started kissing it, and buried his face and
nose between my arse crack. I didn't know why he would want to do this
exactly, but I did know that it felt pretty good, better than smoking on a
cigarette in any case.

After a while of him tonguing, licking and French kissing my bottom, he got
up and undid the belt on his trousers and pulled down his zip. He pulled
out a very fat cock from his underwear, and asked me whether I wanted to
feel really good. As my eyes were transfixed to his massive member which he
wanked slowly as some precum dripped from the end, I mumbled yes I
would. He told me to put it in my mouth and he motioned me with his arm on
my shoulder to get down and lick it. I did so, and so I was sucking another
boy's penis for the first time. I like the way it felt. I felt really good
with my shorts partially down, exposing my round bottom, sucking another
man's cock, with his pubes centimeters away from my nostrils. He kept a
firm hand on my blonde head, motioning me to bob up and down on his
member. And within a few minutes he had become more aggressive, fucking my
mouth quite quickly, before moaning that he was going to cum and pulling
out and telling me hurriedly to get up, turn around and bend over, before
he shot his load all over my arse cheeks. He collapsed his weight somewhat
on top of me, breathing heavy. Then he craned my neck and began kissing me
passionately like a man who had just expunged his energies fucking his
wife. He rubbed his spent and sticky cock between my butt crack as he held
me kissing my face and mouth.

So that was my first sexual encounter at that school. The prefect had been
smarter than average in taking me to a place he knew would be safe from
prying eyes of masters. But when Luke Daniels had come to my room at eleven
at night, he or rather we, were not so smart. He was a semi-friend of mine,
we shared some classes together, and I guess he must have liked something
in me, for he also came to me bearing cigarettes, but seeking much more. I
had opened my window and as we smoked out of it, his hand had also found
its way down to my butt and he began to caress it slowly. When I turned to
face him questioningly, he smiled naughtily and kissed me. Before long, he
had removed my sweater top and was licking at my chest, paying extra
attention to my nipples. He was obviously no stranger to this sort of
thing, and he lifted me and took me over onto my bed. He removed my
trousers and as he snogged my face, he put a couple of fingers into our
mouths. I sucked on them, but not for long, because he took them away and
started fingering my butt as he kissed me. Before long, I had my legs up in
the air as he fingered my hole and pinched my nipples. And then, he climbed
on top of me and tried to put his cock inside my hole. After a few false
starts, his head slipped in, and he managed to get his shaft well up inside
as well. He was still quite passionate, kissing me and playing with my
nipples all the while he was on top of me fucking me. It felt so amazing
and awesome. The bed was a bit rickety though and it squeaked from Luke's
movements pumping up and down. So imagine the shock when the door to my
room was opened and the light switch flicked on. It was Mr Graham the house
master, who also happened to be one tough SOB, an ex army officer. He
caught me with my legs up and Luke on top of me. Mr Graham's eyes were
stern and Luke looked absolutely petrified, as I'm sure did I, being caught
in this awkward and embarrassing situation. Mr Graham didn't even need to
say anything, he just stood there. His stern presence was enough. Luke got
off me, without saying a word, and meekly collected his clothes.

In the end, we ended up in front of Gilbert, the headmaster. He gave us
some silly punishment and that was the end of the "sordid little matter",
in his words. So a few months later, when I was down on my knees between
the legs of Mr Matthews, the 35 year old biology teacher lapping at his 7
inch cock, and Mr Gilbert had entered the room, he was again not best
pleased. I guess Mr Matthews, who was dark haired and actually kind of good
looking, he kept his body in shape anyway, had heard about me from Gilbert
or Graham, because he requested I stay after class to discuss something. He
had told me that he was very pleased with my work and the progress I was
making in his class, but that he was concerned that I was OK with
everything else. He said he had noticed some of the other guys picking on
me and he wanted to make sure everything was fine with me. Well, they were
teasing me that particular day pretty mercilessly, but to be honest it
didn't bother me very much. I mean, everyone gets ribbed a bit every now
and again. I didn't mind. I therefore told Mr Matthews that I was fine. He
had replied OK, but he put his arm on my shoulder, and said if I ever
needed to come to talk to him about anything, absolutely anything at all,
it was OK with him. At that point I had looked up into his eyes, and he had
gazed back into mine, and despite the age difference, the air was electric
with male on male lust, and out of my own volition, I had started
unbuttoning his trousers. He didn't stop me, and soon I had his girthy cock
out wanking and sucking off my biology teacher. I was really enjoying this,
even more than my previous sexcapades, perhaps because of the forbidden
nature of what was occuring, when old Gilbert burst through the door. He
was furious. Unfortunately Mr Matthews took most of the blame, him being
the one with a position of responsibility over me. But Gilbert sounded off
at me also: "You, again!" he had hissed at me angrily.

Mr Matthews didn't lose his job immediately. But he was gone a few months
afterwards. I was really scared and felt really bad that he had been sacked
on my account, and one afternoon I sheepishly knocked on old Gilbert's door
and I asked what had happened to Mr Matthews. I told him what had happened
was totally my fault and that it wasn't right he should be made to lose his
job. Gilbert seemed very unimpressed with me (but then he seemed
unimpressed with the world as a whole), and told me to stop blubbering,
that Mr Matthews had been scheduled to take a year teaching abroad in New
Zealand, and that after our little "escapade", they had decided that it
would be appropriate to bring that forward a little. He assured me that Mr
Matthews was fine and would be returning to teach here after some time. But
he also warned me that he didn't want to see me here over matters of this
nature again. He said he had been looking through my records and that I was
a good student, so why I got into these situations, he did not know...

I thought about telling him that they made me feel fucking amazing, having
another man's cock inside me, but somehow that might not have been most
appropriate...

So things died down for a while for me. But one day after swimming, in the
changing rooms, a guy named Joey Douglas got a hardon. He tried to hide it
but it was quite obvious his engorged member trying to break through the
flimsy Speedo holding it back. Some of the guys noticed and started to
tease him mercilessly, even pulling down his trunks to mock him further,
letting his erection spring out visible to all. I was sat at the other
corner of the changing room, and I started to get a major boner at all that
was going on. When the teasing got too much for Joey, he told the other
guys firmly to fuck off and moved to another area of the vast locker area
to change alone. I tried to move off without anyone noticing I was gone,
and certainly without anyone noticing the hard boner I was also now trying
to hide. I found Joey in the remotest corner of the locker rooms, and at
the sight of him and his wood, I... well, I just walked up to him and
pulled my trunks down, bent over and offered my bottom up for him. And he
took his opportunity, he fucked me quickly using spit for lube and came
within me in less than a minute. It was very horny and very exciting. From
that day on Joey and I became fuck buddies in school. He always fucked me
and I always loved it.

I didn't want to get caught again, so we used to go to the deserted
clubhouse which used to be the rowing club. Now it was just filled with
cobwebs and dust. But it was private. We'd go there three or four times a
week and fuck. Usually we wouldn't bother getting out of our clothes, just
unbutton our trousers and a few buttons on our shirts as I wantonly
bottomed for Joey's cock. But again, one day we were stupid and our
passions got the better of our brains. We had been sent to get a new set of
textbooks from the science store room, and figuring we were alone, we took
this opportunity to get up to some fun. We started out by kissing and Joey
undid my pants and fumbled around my arse, eventually a couple of his
fingers finding their way up inside me. He kissed my neck as he fingered my
butt and and then brought his fingers up to my nostrils for me to sniff. I
did and gasped at the smell of him mixed with my sweat and arse. As I
gasped he shoved those fingers into my mouth and told me to suck on them. I
closed my eyes and sucked on his fingers imagining it were a fat cock,
savouring the taste of arse on skin. Joey smiled loving this, and he would
continue with this cycle of fingering my bottom and making me suck on
them. All the while he talked dirty to me, telling me what a fucking hot
little whore I was, asking me if I liked sucking his dirty fingers and
telling me I liked the taste of my own arse, didn't I?

In the process of all this horniness, we managed to lose most of our
clothes. I lost my shirt and had my trousers down by my ankles so that I
was just wearing the school red and yellow tie loosely around my bare neck
and chest; while Joey took his trousers off completely and stood in front
of me in a masterful pose in just his shirt with three top buttons undone,
a tie and his grey socks. At this point, he told me that I liked the taste
of fingers and arse so much I should finger my own butt and taste them and
tell him how they tasted. So I squatted before him, fingering my own sloppy
arse looking at Joey staring down at me with his steely dark eyes as he
jerked his own cock and slapped my face a bit with it. He'd tell me to suck
on his cock while I fingered myself and then pull his cock out and tell me
to suck on my dirty fingers and tell him how he tasted. This was the most
fucking horny experience of my life, and Joey was loving it with a sinister
smile on his impish face. He told me I was a real bottom boy, and that I
probably needed something more than just a few fingers up my arse.

At that point, he told me to get up and take my trousers over my polished
black boots. I struggled to do so without tripping up, all the while he
pinched and twisted my nipples, knowing that I liked that. Then he told me
I was such a big bottom boy that I needed to get fucked so that anyone
outside could see. He told me to get up onto the table which was located on
front of a large window overlooking the playing fields. He told me to bend
over on my hands and knees like a dog and hold open my butt for him. I
looked over my shoulder as he masterfully gobbed a long drop of spit so
that it landed around my already well fingered hole, and then he guided his
cock to its target. He entered me without much resistance, and began
fucking me with long slow strokes, so that his cock would enter completely
up to his balls, and then he'd pull right out, so that my hole would stay
open for a second, and then clench shut. He did this over and over again,
it obviously fascinating him as he told me how it was "Fucking sweet". Then
he grabbed me and lifted me up onto my feet, and he fucked me with my
entire body exposed to the window, so that anyone who might have been
walking below might have been able to see.

Joey was grunting and I was moaning in ecstasy. He lost his remaining
clothes, and he grabbed the tie around my neck and used it like a dog chain
to pull on as he fucked my bottom hard. I had arched my back and was
grunting, moaning and making way too much noise. And Joey was fucking me so
ruthlessly I thought the table we were on might break and we might even
fall through the floor beneath us. All the while, Joey was enjoying being
in masterful mood, telling me to tell him what a bottom boy whore I was and
how much I loved what he was doing to me. I in turn was telling him to keep
on fucking me, because I was his bottom boy who loved his big cock up my
shute. I guess we were making far too much noise because that is when the
door flung open and we were caught. But by this point, I was pretty much in
my own world of ecstasy and so although I was aware the door had been
opened I kept on pushing my arse back and forth onto Joey's cock, and he
must have cum at the situation and being caught because he shot a load into
and over my arse.

Mrs Wilson, whose English class was directly below us, and who came up to
see what all the noise was above her room, didn't know what to make of what
she had walked in on. She stood there, flabergasted, before she picked up a
pretty thick science text book and whacked me with it. "You dirty, filthy
boys! Put your clothes on at once!" She tried to whack Joey with it too,
but he was agile enough to leap out of her way. She actually tried to catch
him by running round the table, wielding the textbook like it were an axe,
swinging it at him. All the while she was screaming obscenities at us over
what she had just witnessed. Eventually catching him in the corner where we
had dropped most of our clothes, and whacking him pretty hard around the
buttocks and thighs. And me, on my hands and knees on the table watching
what was going on with Joey's fresh white cum dripping from my hole all
over my crack and onto my hairy balls. It must have been quite a scene.
Truth be told, it was probably the most exciting thing the middle aged lady
had seen in a while, but of course she couldn't admit that could she?
Inevitably of course we ended up in front of Mr Gilbert again. Joey
complained of being hit by Mrs Wilson, but I was more quiet having been
here before. It was here that I was blasted for my "persistent slutty
behaviour" and I was given two weeks detention from four until seven each
day. Joey was given a similar punishment, but we were kept apart so that
there could not be a repeat of our antics.