Date: Tue, 30 Jun 2015 23:40:15 +0000
From: Bruce Demosthenes <sourceskid@hotmail.com>
Subject: Can i fuck you 27

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****

I thought about making arrangements to meet Randy that day when I saw his
text.  There was something appealing about getting another load in my ass,
especially since I had just sadly expelled three loads moments ago.  I also
liked the idea of having another cock in my ass that was bigger than these
boys'.  In fact, getting systematically bigger, from 4" to just under 5"
probably more than 5" to Randy's which had to be at least 7" (it looked
even bigger because of the big head and the fact he shaved off his pubes)
all in one day would be an amazing experience.  But that would mean my two
worlds would overlap and I want to keep Randy separated from the school
(well at least as separate as possible given his friendship with boys at
the school).

When I checked my schedule I decided the best options the next day were
during my free period which was right before lunch (I could also skip
lunch), or alternatively, after classes as I could probably ditch
supervising sports (and I could also skip dinner).  So I texted him with
the best two times I could arrive, either 11am or 4:15pm, allowing for the
15-20 minutes to walk down the hill, so he would have a choice in case he
was working or busy.

When he texted me back the word "BOTH" in caps a few seconds later, before
I had time to get my stuff from the office for my afternoon classes, my
cock got hard.

I sat down behind my desk.  It felt like the wind had been knocked out of
me (and I also needed to sit down to adjust my now hard cock and wait until
it deflated).

While I waited for my cock to go down I wondered if Randy had messaged me
before today and proposed multiple fuck sessions in one day or even in one
week if I would have told Alec about Liam and Justin and gotten him to
orchestrate their fucking me.  Probably.

I had begun thinking about Liam and Justin fucking me on Sunday and Randy
had fucked me that very morning.  In fact his fucking me had left me very
horned (though maybe I am just always horned).

Horny as I was I didn't jack off then or that day or the following morning.
I just forced myself to think of anything other than sex (difficult to do
when surrounded by hot boys in their school uniforms or gym kit or in their
underwear on the flats, including several who fucked me).  It helped a bit
that I considered Randy in a category different than these high school
boys.

At 10:45, I headed down the hill.  There wasn't sufficient time to change
out of my tie and jacket and dress pants.  I wanted to be back for lunch.
While I had considered skipping lunch as either an alterative time slot (if
Randy had not been fine with the two I proposed) or in case our fucking
went long, I would have to make an excuse for why I was not at the head
table and as it was I would not have to make an excuse for why I wasn't
able to supervise sports in order to go back to Randy's so that was just
too many excuses.  So I went straight to Randy's without changing.

I arrived at Randy's at just after 11.  He buzzed me into what was a pretty
standard small apartment building in a neighbourhood which was not known
for any nice buildings as it was the lower income area of city, ironically
just down the hill from the richest neighbourhood where the school was
located.

After I was buzzed in I climbed the stairs (there was no elevator) to the
second floor and found his unit and knocked.  Randy opened the door just
wide enough for me to squeeze in and closed the door.

A quick look around the apartment revealed a small bed, a table with two
metal kitchen chairs and a small glass computer table (which I recognized
from Structube as I had one in college) and a computer chair in front of
it. It reminded me of the apartment I had when I did my undergrad and
teacher's college.  In fact, it was about the same as my room on the flat
(though in my flat, since I had use of the on-duty office (which was mostly
mine as I was on duty every night and long weekend as well as one weekend a
month), I had essentially two rooms.

After looking around the apartment I turned around to the door and found
Randy leaning against the door.  He was wearing only what I thought was a
pair of briefs.  They were very sexy briefs.  They were grey with a fairly
wide waistband, which is now standard on designer briefs, but these didn't
have a designer name in large letters all the way around, like Calvin
Klein, Diesel and other designers do.  The waistband was simply black with
a small 'body aware' logo in the front above the pouch.  The solid black
waistband was very dramatic against the grey.  The leg elastic band was
light blue and had the same mottling pattern on it that made it also look
exactly like the cotton or linen of the brief (even though it had to be
elastic).  This same strip ran up either side of the pouch (there was no
fly) perfectly framing the pouch.

And what a pouch!  His cock filled it so full that the blue elastic around
his legs were pushed out slightly in the front on both sides of the pouch.
Randy's cock, which was soft, was pointed down in the pouch, though the
head was visible, it being so much bigger than the shaft.

While Randy had the confidence and self control to be soft, the sight of
him in these briefs caused me to rapidly expanding in my own briefs.

I could see why he didn't open the door wide.  While he was in underwear
and the grey fabric was thicker material (the mottling made it look linen
but it was thick like cotton) because of that big cockhead you could
definitely make out detail of his cock.

God this guy was sexy.

I had been struck by how tall (around 6 feet) this boy was.  The briefs
suited him because they divided his body.  He looked less skinny, as he had
seemed when he got naked in the back of the book store.  Rather he simply
looked slim and tall.

Randy watched as I looked him up and down.  Then he pushed off of the door
he was leaning against and turned around.

My jaw dropped.

These weren't briefs and they weren't a jock.  They were briefs that had
the back missing.

It wasn't ripped out.  They were designed this way.  There was the same
light blue elastic all the way around his ass, which was totally hanging
out.  Where I had thought the 'briefs' suited his body in the front, they
definitely added to his look in spades in the back.  This design made his
ass look so round and perky, even though he was one of the thinnest young
men I had seen naked or in underwear (and in a private all boy's school I
had seen lots, naked and in jocks and underwear).

The look was truly breathtaking.  So much so that I wanted to compliment
him (he just brought out a need in me to confess unsolicited my feelings
and thoughts).  I just couldn't find the words.

Before I could put together a coherent sentence Randy turned back around
and walked towards me.  I could see his cock was hardening and where the
light blue elastic leg bands had been slightly pushed out before, there was
now a noticeable and growing gap.  His hardening cock was pushing the pouch
of these snug form fitting briefs out from his body and stretching the
fabric.  He made no move to adjust his cock, he just let it strain the
material.

While I was busy admiring his body, his ass-less briefs and his hardening
cock, and thinking of words to describe the combined sight, he simply said
"you look sexy Bruce."

It was still disconcerting that he was calling me by my first name but the
sight of him in those briefs made my brain, which usually was so sharp,
though lately very reflective, self-doubting and analytical, complete mush.

I just nodded.

"I love you dressed up," he said as he came up right in front of me.  "But
I think you are way overdressed for this party."

I just nodded again, speechless.

He unbuttoned my jacket and pushed it off my shoulder as I stood there
dumbstruck.  I couldn't believe that I was about to have sex with this
stunning boy in these ass-less briefs.

Throwing my jacket on his bed, though in way that made it land flat and not
in a pile (something I appreciated as I had to go back to work), Randy then
reached up and pulled my tie apart and undid it and pulled it out of my
collar and threw it too on the bed.  He then undid the top button of my
shirt.

I came out of my stupor and took it upon myself to quickly undo my pants
and push them and my underwear down to the ground.  Unlike Randy, who had
actually taken some care in how he threw my blazer and tie, I just left my
dress pants and briefs down to my ankles.  I didn't bother to pick up my
slacks and fold them, something I would have done diligently in my place, I
just stepped out of them leaving them in a pile on his floor.  I wanted
this, whatever it was we were going to do, to happen as soon as possible.

My cock was already rock hard in excitement.

As he slowly unbuttoned my shirt I hurriedly removed my socks.  The pace he
was unbuttoning my shirt was too slow so I started quickly undoing the
buttons working up and meeting him half way in my urgency (even though he
had started before I had even undone my pants).

I let him, much slower than I would have, push the shirt off me.

Now naked I let him move me, by taking hold of my upper arms, to the
computer chair.  Once he had me sitting there naked, he made some
adjustments to the arms to lower them so they were slightly higher up than
the top my thigh.  Then he spit on his hand he rubbed the spit onto my
cock.  He then spit again on his hand and rubbed it into his hole.

I knew where this was going and while I wanted him to fuck me (I had since
his text yesterday after lunch, as I had since he had done it to me on
Sunday morning) he was too hot to say no to.  In fact, his ass was so hot
in ass-less briefs (did they have an actual name?) I wanted to be inside
it.

Randy, tall as he was, was able to while facing me, straddle me and the arm
rests.  I aimed my cock at his hole and sat down on me.  His legs were
still on the floor which made me wonder if he was actually taller than 6
feet but then I realized the chair was lower than a proper setting for me,
so he must have lowered it to its lowest height before I arrived.

As if he could read my mind, he said "my desk and chair arrived today, so I
though I would use you to break them in."

The idea that he had probably had sex on every piece of furniture in the
apartment was incredibly hot.  This boy was experienced and still
adventurous.

Even though we were only using spit for lube Randy slid down onto me fairly
easily.

I was struck again by how warm and wet and tight his ass felt around my
cock.  It really did feel like a velvet glove wrapped around my cock.

He immediately began to move.  His legs over the arms of the computer chair
gave him leverage and soon he was moving up and down on my cock.  I was too
inexperienced to know that this was actually a rare thing.  In this
position the bottom sitting in the top's lap usually moved only an inch or
two.  He was able to use the arms of the chair to move up and down and
seriously fuck himself on my cock.

The feeling was even more erotic than the sight of him wearing sexy
ass-less briefs.  I found myself reaching over and running my hands over
his back as he moved up and down.  Then I found my hands going to his ass
and feeling the cotton of the briefs on his hips and the big opening in the
back and his ass cheeks which I began to instinctively squeeze before
moving my hands up and down his back.  I also once or twice reached down
and felt my cock and his asshole and picture what it looked like
disappearing into his hole.

He was so gorgeous sitting in my lap facing me.  I alternated between
looking up and staring into his eyes (which I found to be bottomless pools
of cool water) and then hug him close as he was in my lap and next to me in
between him riding my cock.

He was fucking himself on my cock and while I knew I should be doing more
it was just so pleasurable.

I was not a top (or was I?).  I just knew this was fucking hot and I was
fucking? well being fucked or being used by him to fuck himself (I had no
idea what I was actually doing).

The only thing missing was a mirror on the wall so I could see my cock
disappearing into this tight ass (maybe I would offer to get one).

Before I could finish thought he changed movements.  Up until then he had
mostly been moving up and down on my shaft but not really touching my hips.
I hadn't had a lot of experience with positions as a top but my most,
though still meager, experience as a bottom had shown my that different
position mean different levels of body contact.  Though in every one I had
been subjected to involved hips hitting my ass on the down stroke.  In this
position he only moved on my shaft (he made sure, by using the arms of the
chair, not to sit down fully in my lap).

Then suddenly he was sitting in my lap and moving his ass back and forth.
He was, I think it is called, twerking!  His hips kept moving so quick in
my lap the sensation was mind blowing.

I couldn't help myself, I started to cum

He didn't stop.

His ass kept rapidly moving on my cock as he twerked in my lap.

I came and came and came!

Since we weren't likely to be heard I cried out "oh fuck Randy" "fuck fuck
fuck" "god-damnit" as I came in his ass, which wouldn't stop moving, "I am
cumming in your ass".

The more verbal I got the more he moved and the more I came.

When he finally pulled off at me I was spend.  I looked at my watch.  I had
only been here for 20 minutes.  I had more time though I should clean up as
I was wearing dress clothes.

"That was amazing," I said.

"Do you think you might like to top or be versatile," he asked.

"Hot as that was I know I prefer being fucked," I said truthfully.  "OK,
when I saw you from the back in this underwear I couldn't stop looking at
your ass and I was totally happy to be inside you.  But I also want a pair
of these for myself.

Always the salesman, Randy said "we have them in green, grey, peach, yellow
and charcoal."

"One of each," I said without any hesitation.

"I will go by the store and get you one of each this afternoon," he said as
he laughed at my eagerness.  "But when I fuck you after school I want you
naked."

"On the desk," I asked seriously, thinking he wanted to christen both new
pieces of furniture.

"No, I want to fuck you properly on my bed," he said.

I smiled happily.  I loved this idea which sounded romantic, though I now
knew from experience that you can be fucked may different ways on a bed
that has no romance or affection.

"Can I clean up," I asked.

"Help yourself," he said.

I went to his washroom and used a facecloth to clean off my cock.  As we
hadn't used lube and he was so clean (I wondered what his trick was because
when I cleaned the boys' cocks they were never this clean) the facecloth
was relatively unused so I put it over the rack to use again when I came
back (I didn't want to make this young man to have to do laundry).

I got dressed and Randy followed me to the door.  Before letting me out, he
leaned in and kissed me.  I had only been kissed by Alec so was taken by
surprise.  It wasn't overly aggressive or sexual.  It was just
affectionate.  When he broke away he smiled and said "see you after school
teach."

Where earlier I had felt uncomfortable at this young man knowing I was a
teacher, being friends with boys in the school and calling my by my first
name, I found myself grinning uncontrollably as I walked up the hill to the
school.

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