Date: Wed, 20 May 2015 12:34:21 +0000
From: Bruce Demosthenes <sourceskid@hotmail.com>
Subject: Can i fuck you? 14

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I had five loads of cum in my belly.  Even when I had sucked guys off
occasionally in public restrooms I had at most sucked two guys off in a
day.  And those were consenting adults.  I had sucked off three underage
boys who, while pretty much in charge, they were only 13 and 14 and not
nearly old enough to consent.

The more I alternated between guilt, regret, longing, lust and denial the
more confused I became.  So I went to my room and turned on the TV to take
my mind off of everything.

It was only midnight when I remembered I was supposed to check to see
Clifford was in his room.  I contemplated not bothering.  He hadn't been on
the flat at the required time the night before but he also felt he didn't
have to and letting him fuck me had hardly been a way to reinforce my
authority.  My ass was still sore from the 'dressing down' I had given him,
thinking of it made me laugh, I had intended to dress him down and I ended
up undressed, him on top of my back and his long uncut cock buried in my
ass.

I decided to check on him anyway.  If he was there maybe it might lead to
sex.  While I had lots of it already that day, I had yet to cum and I
really liked cumming last night by his cock hitting my prostate.

When I got to his room the light was on.  I opened the door and Clifford
was lying on the bed in the black boxerbriefs he likes to wear.  They
really do accentuate his long lean form, though the dark material makes it
harder to make out the details of his cock, which may be why I never
realized he was uncut and quite large.

Clifford glanced at his clock and then said "I don't see why I have to be
back by 11pm if you aren't going to come around until midnight."

"It's not for me, it is the rule," I said, almost apologetically.

"Well I left the 'club' early because of it," he said, putting the word
'club' in air quotes.  I had no idea what that meant but I decided not to
ask.  I already had too many secrets and I didn't want to be in a position
where I was supposed to report a boy for doing something they weren't
allowed to and then couldn't because what I had done with them was much
worse.

Clifford got up and walked over to his closet, reached into the dirty
clothes and pulled out his jockstrap.  He tossed it to me and said "put
this on".

"Pardon," I said, shocked by his brazenness and not entirely sure what was
about to happen.

"Last night you got my sheets wet.  Not only did I have to sleep in your
mess but we don't get new sheets until Wednesday so I have three nights of
crusty sheets thanks to you."

"Sorry," I said meekly.

I began shucking my clothes and once naked I put on his jock.  The leg
straps and waist band were a little tight, but the pouch, even though I was
hard in it, had plenty of room.  I also found it an incredible turn on.  My
cock was where his big uncut cock had been.  When he had tossed it to me I
had been tempted to sniff it and now I regretted not doing that.  Just
knowing my cock was where his ball sweat, piss stains and maybe even some
cum was just added to what had started as a humiliating exercise (I was
wearing his dirty jock because I could stop myself from cumming while he
fucked me, something he clearly planned to do again).

Clifford pointed to the bed.  I didn't need to be told twice.

I lay face down on it like I had the night before.  And Clifford again
reached into the nightstand and pulled out some lube and squeezed it into
the crack of my ass.

It hadn't struck me the night before but that seemed like a waste of lube,
just squeezing it out onto my ass.  I hadn't had much experience and my
teacher for anal was initially a 14 year old kid who was as inexperienced
as I was.  I had also had sex with Abbey but I assumed he was a novice to
anal given interest in girls.  But both of them just applied some, albeit
baby oil, to their hand and then rubbed it into my hole and on their cocks.

Maybe the extra lube made it easier for his uncut cock to enter foreskin
still around the head, which is how I felt it had the night before.  Maybe
he liked it sloppy so he could slip and slide around.  Or maybe he didn't
mind fucking my hole but didn't want to touch it (in which case he could
have handed it to me to apply to myself).

I didn't have much time to think about it as Clifford had mounted the bed,
pushed my legs apart and was lowering himself onto my back, his big cock
sliding into my very slippery hole.

Once the full 7" had been plunged into me I let out a very loud moan.  Once
again it had connected with my prostate.

There was something about lying on this student's bed, barely big enough
for one 17 year old boy so too small for me an adult with his virile body
above me, almost the full weight on top of me.

Clifford began the long slow strokes that I remembered so vividly from the
night before.  He was a methodical lover and his cock going in and out of
my ass was like an oil well steadily pumping the ground trying to bring up
the crude.

While it was mostly hypnotic, it was also incredibly erotic.  I had five
loads of cum in my stomach having sucked three boys cocks without any
release for myself and this boy was hitting my prostate on every down
stroke.  I couldn't help myself and before long I was cumming into the
pouch of this boy's jockstrap.

I tried not to let out a sound.  I don't know if he knew I had cum or if he
cared.  Clifford just kept fucking my ass with long strokes like a piston
in an engine.

He never picked up the pace, he just kept the same rhythm but something in
me knew he was getting close.  Maybe it was his muscles tensing or his
breathing.  I just knew.

When on a down stroke he just stayed inside me I could feel his cock
pulsing in my ass.  I knew he was depositing his load deep in my ass.
Something about that was so exciting and I realized I was once again hard
in his jock.  I was so turned on by feeling this boy cum in my ass.

When he pulled out I got off the bed.  Clifford noticed my hard-on and
asked "I thought I felt you cum."

So much for trying to be quiet.  I guess he felt my ass squeezing his cock
as I came.

"I did," I admitted and then added embarrassedly "I found your cumming
inside me so hot it got me horny again."

"Hmmm," Clifford said.  "Maybe we should invite you to the club."  This
time he didn't use air quotes but I could picture them.  He wasn't talking
about a night club or a bar.  There was definitely something else going on.
Did I want to know what it was?

I pealed off his jock which was soaked with my cum and threw it in his
dirty clothes pile.  Then I put on my clothes.

Clifford pulled on his boxerbriefs and when he went to the bed he looked at
it frowned.

"That didn't entirely work," I walked over and saw a wet spot.  I had cum
so much it had leaked through the rubber material of the jock.

"Sorry," I ventured.

"We will have to come up with a better solution if you are going to do this
again," Clifford said.

As I walked down the stairs back to my room I had two thoughts running
through my head.  First what was the 'club'?  And second 'if you are going
to do this again', who said I wanted to and he fucked me, it wasn't me
using him.  Though maybe it was.  I was the teacher and he had made me cum
both nights.  Maybe he didn't even want to have sex with me, though the
load of cum in my ass that was leaking out into the back of my underwear
suggested otherwise.

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