Date: Sun, 9 Mar 2014 15:07:44 +0000
From: Bruce Demosthenes <sourceskid@hotmail.com>
Subject: Becoming Brian's Bitch 5

I did laundry on Sunday.  The laundrymat was down the hill in the poorer
area of town, so usually a group of us would go to laundry together.  The
group I usually went with included Robert and some of my younger friends as
most of the friends I had made as a boarder were younger than me.  I
actually looked forward to doing laundry with them as I could check out
their dirty briefs in their laundry pile when they weren't looking.  Hell,
I had even on a few occasions stolen a pair to sniff as I jacked off at
night thinking about my friends' cocks and balls that filled them out as I
inhaled the smell.  I had even lucked out once and stolen a pair of dirty
briefs from my friend Stephane that he must have jacked off into recently
and I got to relive my night in the library with him in my mind (see
Roxbury College story line).

But now that I had to wash my small dirty jockstrap I opted to sneak off
and do laundry by myself.  Besides, I had an additional task today and that
was to purchase an enema.  After doing laundry I returned my clean clothes
to my room and set out for downtown.  I chose a drugstore that was out of
the way and after much searching I found where they kept the enemas.  I
grabbed that but also grabbed bandages, a package of tampons and a straight
porn magazine.  I guess I figured the salesperson would believe I was
buying things for my parents or would be so distracted by an underage boy
trying to buy a porn mag he wouldn't think twice about the enema, and it
being straight porn he wouldn't possibly think the enema was for me.  In
the end the salesclerk didn't seem to even care what I was buying, so I
wasted a lot of money for no reason.

My next mission was to talk to Brian about Robert.

I tried all week to get a moment with Brian alone but it was like he
intentionally was avoiding me.  Finally on Thursday I got to sit next to
him in English class and, when no one was looking, I wrote in his notebook
"David and his younger brother saw my ass last weekend and figured it out."

"Figured out what," wrote Brian who now seemed to relish my writing out the
obvious.

"They I had been fucked," I wrote.

"Lots of people get fucked," Brian wrote being intentionally obtuse.

"Fucked in the ass," I wrote.  "They saw the belt and zipper marks."

"Did they out you," he wrote.

"They seem to want me to service Robert," I wrote and then quickly added
"but I told them I needed to check with you."

"So what do I tell Robert," I wrote.

"Just show-up Saturday," wrote Brian. "Did you get the enema."

"Yes," I wrote.

"Be clean and be on time," he wrote and then he closed his notebook so I
couldn't write anything else.

Throughout the week I had done as I was instructed and I had the tight
jockstrap on every day and night and as I was increasingly horny both
because of Brian having fucked and dominated me and the prospect of maybe
doing something with Rob I jacked off in the jock every night.  I wanted to
do it more but I was worried the wet stain on the jock would show through
my pants so I just did it when my roommate went to sleep and during the day
suffered with periodic hard-ons (which I discovered the tight jock would
hide under my grey flannel dress trousers, or at least I thought it did and
no one pointed out my frequent hard-ons).

On Saturday morning I went to the bathroom in the locker-room.  As it was a
Saturday no one goes into the locker-room unless there is a sports game
against another school that is visiting, or at least I hoped, and I opened
the enema box (which had been hidden in my underwear drawer all week) and
read the instructions.

Filling it with warm water, I went into the last stall and locked the door.
I stripped off all my clothes but the jockstrap (I felt obligated to wear
that while I did this) and I put the hose in my ass.  Filling myself with
the warm water I then sat on the toilet and released.

I actually found it exhilarating and, without putting my clothes on, I left
the stall in my jock and refilled the enema bag with more warm water and
then returned and washed myself out again.

I realized as I was doing it how much of a bottom I had become at only 17
but I didn't care, I found just preparing to meet Brian by cleaning myself
was very sexual.  And I hoped like hell he was going to be willing to fuck
me after all this work when I went to his place at 2pm.

Once I was sure I was clean, I put my clothes back on (thankful no one had
come into the locker-room and caught me) and went upstairs.  I stowed the
enema bag in my bottom dresser drawer where I kept my underwear and left
for downtown to kill time while I waited until 2pm.

As had become my practice I was in front of Brian's house before 2, but
waited until my watch hit 2 before letting myself in and climbing the two
flights of stairs to the attic.  Brian was not there but I knew what was
expected of me so I stripped down to the jockstrap and stood in the middle
of the TV room with my hands on my head.

I don't know how much time passed.  Unlike the previous times, I was not
filled with panic at being caught by Brian's mom or brother.  It hadn't
happed to date and while I knew it was a possibility, I was where I was
supposed to be and I just waited dutifully.

Eventually Brian came upstairs.

He walked over to me and knelt down and opened my ass cheeks to inspect my
hole.

"Did you get an enema," he asked.

"Yes sir," I responded.

He shoved a finger into my hole and moved it around and pulled it out and
inspected it.

"Good boy," he said.

Like the week before I could hear him undoing his pants and, instead of
sending my for lotion I heard him spit.  I realized I was going to only
have his spit for lube.

Before I could think long about it, his cockhead was against my hole and he
was shoving in.  Lotion makes a big difference I discovered.  With only
spit it felt like his cock was tearing my hole as he forced his big tool
into my hole unlubed.

I did not cry out or flinch, I just stood there as he kept pushing (and he
had to push hard to get it into my without lube) until he was all the way
inside.  Again I could feel his belt and zipper against my ass and upper
thigh.

It seems this was my new lot in life.  Brian would bother to even push his
pants down or get lotion.  When I was there stripped to my jock willing to
take his cock he would just undo his pants and shove into me.

Realizing how hard my cock was in my jock I had to admit I liked my new lot
in life.  This is where I deserved to be, where I wanted to be.  I was
Brian's bitch with my clean ass being filled by his mammoth cock, which
deserved to be worshiped the way I wanted to and did in my mind every night
I jacked off in my jock.

The first dozen strokes were excruciating without any lube beyond his spit,
but before long it got better.  I don't know if my ass was sweating or I
was getting used to it but from feeling like he was tearing my anus apart
it quickly transformed to my being able to feel far more intently the
details of his cock as he slid in and out of me.  I actually found myself
preferring that he had only used spit because I could feel his cock so much
better.

The digging in of his belt buckle and zipper still hurt when he thrust into
me, and I missed feeling his balls against my ass, but I was his bitch boy
and I was just lucky he was willing to put his cock in my ass.

Brian seemed even more than the previous week to just get this over with
and he was quickly pounding my ass like there was no tomorrow.  I knew it
wouldn't take him long.

I knew it wouldn't take me long either, as I found myself loving him using
me to just get off quick.

As Brian's breathing got quicker, mine did too.  As his thrusts got more
intense I could feel my orgasm approaching.

As Brian began to tense and shove in deep to shoot his first strands of cum
I felt myself do the same into my jock.

Every thrust after that first spurt of cum, made me cum in my jock as he
did the same deep in my ass.

I guess this is what in the porn mags they talked about the pleasure of
cumming together but it was amazing.  Each spurt he unloaded deep in my ass
triggered my cock to explode.  It was like his cum was forcing my cum out
of me.

I also discovered that day I cum longer than Brian.  When he pulled out of
me, I was still cumming in my jock, and I stood there with my hands on my
head experiencing my cock continuing to spasm inside my already soaked
jockstrap.

While I was sad my ass was suddenly empty, I was still in the throes of my
orgasm.

I was so consumed by my own feelings I didn't notice that Brian had gone
into his bedroom and returned with something in his hand.

Once I returned to my own body and could focus my eyes, I looked at what
Brian had in his hand and a quizzical expression must have appeared on my
face.  It was a small rubber object, too small to be a dildo.

"It's a butt plug," said Brian.

I am sure my eyes must have looked like saucers when he said that.

"Don't worry, you won't have to wear it all the time," Brian said as he
moved in behind me and began to put it into my hole.  It slid in easily,
which is not surprising given the fact that he just had fucked me with
something probably six times bigger.

Just then the doorbell went.

"That will be Robert," Brian said.

Brian, who had done up his pants, went down the stairs and I stood there
with my hands on my head and this plug in my ass wondering what he and
Robert could have possible discussed.

When Brian returned with Robert in tow, I braced myself for Robert to burst
out laughing at the sight of me in a jock that I had so clearly cum in, the
marks again on my ass he had seen the week before and now a plastic plug
clearly visible between my ass cheeks.

But the look I got from Robert exuded sympathy.  It was like he felt bad
for me.  Then again, he was here in Brian's house on a Saturday which is
when I was now getting fucked so he had obviously agreed to participate in
some fashion.

Before Brian could say anything Robert ventured "the only way Brian would
let you do anything with me is if he could watch."

Brian clearly didn't appreciate the apologetic tone and snapped "your ass
is my property which is why you have a plug in it" at which it turned
bright red.  I knew Robert knew what I had been up to and the way I looked
left nothing to the imagination but for Brian to say it in front of him was
humiliating.

Robert didn't seem fazed and turned to Brian and said "you just get to
watch, you can't talk."

Brian seemed actually chastened.

I knew Brian had a thing for younger guys.  He had always tried to strike
up conversations with my friends, but they all gave him the cold shoulder.
I never understood why none of them liked him.  Maybe it was because he was
not actually interested in them (what they were up to, how they were, what
they were going through? actual friendship) and simply interested in being
around them (cause I guess he found them hot).

So this must have been the deal Brian struck with Robert.  Robert would
have never fooled around with Brian but he would let Brian watch us.  Plus
Robert and I were boarders so fooling around at the boarding school was
difficult (though not impossible) to do.

Robert took me by the hand and led me into Brian's bedroom.

When Robert had approached me the previous Saturday I had figured he just
wanted to use my mouth and ass to get off the way he used his 'bitches' and
the way Brian used me.  But Robert clearly had something more in mind.

Robert quickly stripped and his hard cock made it clear that he was looking
forward to what was about to transpire.  He was about 6 1/2" cut, but the
head of his cock was like a big mushroom.  His blond pubes made that red
cock head seem even more menacing.  The rest of his compact body was
entirely smooth.

Rob took off my jock, revealing my hard cock which was equally anticipating
what was going to unfold.  When he went to take out the butt plug Brain,
who had taken a seat in a chair across from the bed, said "that stays in."

Taking my hand again, Robert lay down on the bed and pulled me so I was
next to him.  To my surprise he leaned into me and kissed me.

This was definitely not what I had expected from Robert.  In my wildest
dreams I had thought I would end up in a bathroom stall at school on my
knees sucking his cock with him barely talking to me ever again once our
relationship had changed to include sex.

As Robert gently kissed me and then opened his mouth, with me
reciprocating, to French kiss me as his hands explored my body and I did
the same with his.  Before long our explorations with our hands had honed
in on each other's cock and balls and, without having to say a word, we
both moved so we were in a position so we could 69.

Taking the mushroom head in my mouth I actually moaned from pleasure.  I
couldn't believe I had this grade 9's cock in my mouth, a cock I had
surreptitiously checked out when given a chance since I first met him when
he was in grade 8.

I could feel Robert's mouth tentatively exploring my cock, which I knew
must have tasted like cum.  If he was deterred by the taste of cum or by
the idea of sucking a cock it didn't show and he was soon going to town on
my cock, taking it all down his throat and his little blond head bobbing up
and down eagerly.

I didn't need any more encouragement at my end I was soon doing the same,
taking his entire cock down my throat (which was challenging due to the
large cockhead), bobbing my head up and down and trying every trick I could
think of to bring him the pleasure he was giving me between my legs.

My hands played with his body while I continued to suck on his hard cock
which was now oozing precum that tasted so sweet and made me long for his
load which I knew couldn't be far behind.

Rob began to move his hips and I responded to his rhythm so soon he was
half-fucking my mouth and half being sucked by me.  I could feel his balls
tighten up close to his body and knew he was close.  And knowing he was
close brought me to the edge.

Suddenly he tensed and as he did I could feel his cock expand in my mouth.
I quickly moved my mouth up it so I could catch most of his load in my
mouth.  Just as I did I felt Rob take his hand and slide it between my butt
cheeks and push on the butt plug, triggering my orgasm in his mouth.
Clever Robert, he had figured a way to break Brian's rule about my ass
being his.  This made my orgasm so much more intense.  In fact, I had to
force myself to stop thinking about my own orgasm and remember to swallow.

Rob and I lay like that, with his cock in my mouth and mine in his, his
fingers pressing against my butt plug until both our cocks went soft.  Then
Rob scooted around and lay on top of me and kissed me deeply.

Looking in my eyes he said "that was everything I hoped for" then looking
over at Brian added "present company excluded."

Rob then jumped off me and put on his clothes.  Saying to me "see you at
school" and to Brian "thanks for the use of your place" he was out the
bedroom door and down the stairs.

I don't know if Brian found the experience a turn on.  He got to see a
grade 9 naked and hard - a boy he had tried to make friends with and who
had no interest in spending a minute with him.  And he got to watch two
people having sex.  Though on the other hand he had to watch his property -
me - making love to someone else and that someone else even, almost
tauntingly, touched the ass he had declared was his property and used the
butt plug he had put in my to protect his property to sort of fuck me.

Whether it was horniness from the former or anger from the latter, Brian
was over at the bed before Rob was probably out the front door and had
moved me around so I was knees on the floor bent over the bed.  He removed
the butt plug with one hand and undid his pants with the other, a quick
spit on his cock and was entering me hard.

Brian then proceeded to fuck my ass hard.  Holding on to my hips he pounded
his big cock mercilessly into my ass.  I don't know if it was anger or he
was simply turned on, but all I could think about was having made love to
Robert, the taste of his sweet cum on my tongue and his sweet kisses.

Even Brian's big cock pounding into my ass reminded me of Robert's little
hand pressing on that butt plug in my ass.

It must have been at least partially Brian was turned on watching Rob and
me because in what was for him the shortest time ever he was tensing up and
shooting another load into my ass.

Realizing I was rock hard and about to cum again I reached for my jock that
was next to the bed where Rob had dropped it and I put it under the head of
my cock.

Focussing not on Rob, but on Brian cumming in my ass, it only took the last
couple thrusts of his cock as he finished unloading into my ass that
triggered my orgasm and I was soon shooting into the jock in my hand.

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