Date: Tue, 7 Jul 2015 05:20:48 +0000
From: Bruce Demosthenes <sourceskid@hotmail.com>
Subject: Can I Fuck You 30

Remember to give money to Nifty!  Support the publishing of these stories.

****

Just as prep was finishing I checked myself out one last time in the
mirror.  The way the peach almost matched my skin made me feel naked even
if I wasn't completely naked except in the back where my hairless ass was
sticking out through the opening.  I loved the way the leg straps in the
back were low, as low as a jock strap (settling into where my ass tucked
and met the top of my legs), which accentuated my perky round ass.

I pulled on thin beige slacks tempting the fates that some boy would make
out the lines of the ass-less briefs.  If I had white I would have worn
them in the hopes some boy would see the thick black waistband of my briefs
or even the light grey linen piping around the legs, around my exposed ass
and up and down the sides of my pouch through the white fabric.

I had to admit that the contoured pouch did look pretty impressive even
though I knew I only had an average size cock.  Even with my slacks on, it
pushed my package out more than typical underwear and I looked like
something was going on down there.

Throwing on a polo shirt, thinking of how sexy Randy had looked in his
white pants and polo-style shirt, I was now ready to meet students (even
though I had never dressed this casually before for my office hours).

Before I began my office hours I went down the hall to Taylor's room.  I
had been meaning to talk to him about the length of his hair since Sunday
night's chapel.  I don't know why I felt the urge to talk to him about this
right then.  OK, I do know.  I was feeling sex and hoping maybe Liam and
Justin would glance at my crotch or ass and begin to wonder what I was up
to and they were fellow servers with him in chapel (so there was a stream
of consciousness) and their room was across the hall from him.

He was in is room but so was his roommate, so I asked him to step outside.
Reminding him to cut his hair was not something I needed to do in private
but his roommate looked like he was doing homework at his desk, even though
prep was over and the boys in my charge do it downstairs in a classroom.

"I have been meaning to talk to you about your hair," I said when we were
in the hall and had closed the door so as not to disturb his roommate.

"It is off the collar in the back and over my ears," he said, clearly
anticipating what I was going to say.

Taylor's hair was a dirty blond.  It wasn't exactly curly.  It was frizzy.
So while it was technically off his collar and not significantly over his
ears it was a mess.  Like it had on Sunday it reminded me of what a
stereotypical blond California surfer, who spent his days out on the water
with mist and spray and probably never owned or comb or a brush as his
subculture is about rejecting convention and being free, looked like.

"You look like a surfer," I said.

This caused him to break into a big grin.  Maybe that was the look he was
going for but he was missing my point.

"The length rules are so every boy looks presentable and not dishevelled,"
I said, "just like a school uniform, you look like you have never run a
comb through your hair."

This didn't stop him still grinning.

"Look, I want you to, when you fill out your weekend chit tonight, to take
out money for a haircut," which caused him to stop grinning, "and you tell
whoever cuts your hair it is to be no longer than two fingers width," which
wiped the any hint of a smile off his face.

"But the rules.." he started and I cut him off.  "We are talking about the
spirit of the rules and not the letter and you know that young man."

Just then Liam and Justin came up onto the flat and as they passed us they
smiled and nodded to me.  I wondered if they could tell my ass was exposed
in the back or make out any of the details of my new underwear.  I smiled
and nodded back as they went into their room.

Turning back to Taylor he was watching me intently but any notion he had of
arguing was clearly gone.

"Do you understand me," I said, perhaps too sternly as we were simply
talking about a haircut.

"Yes sir," he said respectfully and as I turned to head back to my office
for my office hours he went across the hall into Liam and Justin's room.

My office hours on a Thursday are always busy because I have to deal with
sign-outs for the weekend and requests for spending money so all students
file in.  They complete the chits for money on Thursday so I can get cash
for Friday which I give out after school if I don't have enough in my petty
cash.  For the younger boys sign-out sheets on Thursday allows me to check
they are invited and will be chaperoned on the weekend.

In addition I had to spend time with students who wanted help their
homework, listen to their issues (such as problems with a roommate or
someone in their grade) and let them use the phone.  As the files in and
out I was constantly aware of the ass-less underwear I had on under my
slacks and of how I was devoid of hair on my crotch and ass.  I wondered
how they would react if they knew.

When Alec came to use the phone to call his parents I suddenly got nervous
he wouldn't like me devoid of hair.  But as he just used the phone and left
I didn't have to confront that issue today.  That was also a good thing
because if he had wanted to fuck me (though admittedly the day was not yet
over) he would discover I was also stretched back there.  Not only would
there be questions about why I was hairless there would be questions about
who had fucked me (and I didn't want him to know about Randy).

Liam and Justin came in together, which was unusual, and they giggled as
they filled in their weekend money chits and I gave them cash.  I wondered
what these two 'tikes' (which is how now I constantly thought of them) were
up to.

Abbey came by with his and Clifford's sign-out sheets and I just signed
them without question.  He had brought them a day earlier than before but I
had resigned myself that I had lost control of these two (who I technically
wasn't even responsible for, though had made myself by beginning to sign
their weekend forms).  The thought went through my mind if he knew about me
an Randy or if there was anything going on between them but I quickly put
the thought out of my mind as I didn't want know (even if I would have
loved for Abbey or Clifford to see me in just the ass-less underwear I was
now wearing).

At the end of my office hours, which ran late as it often did on
Thursday's, Taylor came in as the last student in line.  He had his iPad so
I thought it was for help with homework (which I dreaded as I was exhausted
and it was beyond my office hours and getting almost time for round), but
he was only looking to use the phone to call his parents.

Before I left him alone to make his call I spoke to him again about his
long hair.  When I confirmed he would, in fact, get his hair cut on the
weekend, he said "Cowabunga, dude!" and then, when I looked disapprovingly,
added "of course sir."  I handed him the chit.  He completed it and as I
was out of petty cash told him to come by the next day right after class.

Was he actually a surfer?  I tried to recall where he was from.  I thought
it was Vancouver, so he could be.  He also could just be pulling my chain
as I had said his hair looked like a surfer's.  Also wasn't that a thing
the surfer character turtle said in 'Teenage Mutant Ninja Turtles'?

I shrugged it off and left him to make his call in my office, telling him
to close my office door when he was done.  I went down the hall and asked
Abbey to check everyone was in bed.  He said 'no problem' and I then went
back into my bedroom.  As soon as I got in I took off my slacks and checked
myself out again in my mirror.  This underwear was so hot.

I was checking myself out in the mirror when I heard a gentle knock on the
door that connected my apartment with the office.  I pulled on my pants and
dreaded finding Alec at the door.  Had Taylor failed to close the door when
he finished using the phone, and I would have to tell him about Randy,
being shaved and fucked by someone he didn't know about?

I opened the door.

To my surprise it was Taylor.

"Was there a problem," I asked suddenly concerned as this student never
really came to me for anything other than to use the phone and he looked so
serious and a bit nervous.

"Is everything OK at home?  Did you get bad news?"

He leaned in to whisper and I bent down and said "can I fuck you sir?"

I was taken aback.

Had Alec given him this password?  More likely it was Liam and Taylor as I
had seen him to their room and they were giggling when signing their money
chits.  Had Alec given the 'tikes' permission to share this, I was pretty
sure he would realize that was dangerous and he didn't seem (as I had
discovered the hard way) like sharing?

Then again I was being fucked by Randy and I gave him the password (and it
wasn't like the password was a real thing).

I was in ass-less briefs and devoid of hair, how would I explain this to a
14yo boy?  And I had been fucked by a pretty big cock so I wasn't that
tight, would he know or care?

As these thoughts raced through my head he pulled out his iPad and showed
me a position called 'surfs-up'.  It involved the bottom (in this case a
young woman) lying on a surfboard and the top (an older teen who actually
seemed younger than he) lying on her back and, balancing on the board, had
sex.  I scrolled through the pictures and read the descriptions.

That I was reading sex instructions from the web on a grade 10 boy's iPad
(who I didn't know that well) and not sending him packing was now my
bizarre life.

The gist of this was the two would be naked and the bottom/girl would lie
on the board and the top/surfer would sit on his/her upper hips and use his
legs and arms to row them out.  Surfer dude would then put his cock in the
ass (or vagina, as it seemed from the pics only an ass would work).

It wasn't clear if the surfer would paddle and then ride a wave or swell or
it was just about balancing as the pics had the top lying on the bottom's
back with feet hooked around the surfboard as the two tried not to fall
off.  It even said part of the fun was trying to balance and not capsize.
And there would be no way to go from paddling to standing so it seemed
about balance on an unstable surface (with probably the edge of being naked
and fucking in the outdoors).

Just looking at the pics and standing in front of this (now my official
term for him) surfer boy had me hard.  Being horny from wearing these
briefs and having been fucked made saying no, if that had been a word in my
vocabulary, impossible.

I loved being fucked face down on the bed, I think it was becoming my
favourite position.  I was also so horny from wearing these ass-less briefs
and having spend all of my office hours thinking of sex, not to mention
having had sex twice with Randy that day (which instead of leaving me
satisfied made me want more).

So I just nodded and he said "hang ten dude" (whatever that meant, I guess
another surfing term, which just made him seem so much hotter) and pushed
past me into my apartment and began to remove his clothes (a move that
pushed me over the top and I no longer cared we might be overheard).

He was surfer!  A 14 year old surfer, but if we were in California wouldn't
there be blond kids skipping school when the waves were (what do waves do,
break, crash, rise? I just knew these boys existed and they probably would
fuck anyone after riding a good wave, that I knew was a thing, and I might
have been able to convince one to fuck me).

Taylor, his new surfer lingo aside, had a laid back casual attitude ever
time I dealt with him (which wasn't often).  He didn't seem to think twice
about being in my apartment, even though I was his teacher and flat master,
and getting naked.

I went over to him as he was undressing and whispered in his ear "you have
to be very quiet."

"Chilax dude," he whispered back.  "I got your back."

Then he laughed at his own play on words as he was literally going to have
my back. And I couldn't help by smile at his using chilax which also
sounded something a surfer would say.

When he removed his underwear I was struck by how thick his young cock was.
He was only in grade 10 and 14 years old.  It wasn't particularly long
(maybe 5 inches), but it already had a girth on it.  He was probably as
wide across as I was and maybe as wide as the shaft of Randy's.  And as
long as any of his grade 9 and 10s I had let fuck me.

The fact he was blond made his cock look even bigger.  I had figured out
that blonds always look like they have bigger cocks than they do, and now
that I was hairless I knew it was because they light hair colour made the
cock look bigger (which might have encouraged me to shave and not trim).

I stripped too and, while his eyes opened wide when he saw the briefs I was
wearing, he didn't say anything.  I decided to keep the ass-less briefs on
if only to hide the fact I was pube-less.  Plus I liked being fucked with
them on and they would keep my ass snugger and hopefully mask the fact I
had been fucked only a couple hours ago.

I put pillows around the door.  I knew it wouldn't hide the noise if he got
aggressive, though I hoped he wouldn't (I had lost control and I knew it).

I probably shouldn't be doing this now with him.  Even with Alec I waited
until the boys were in their rooms after lights out.  But I wanted his
thick boy cock inside me.  I had only thought about my ass all through my
office hours and now that I saw his and realized it was thick (thick for a
14 year old) I wanted it inside me.

As I was stretched already I didn't get out the lube.  I just spit on my
hand and rubbed some in my ass crack and lay down on the bed.

He climbed on my back, planting a knee on either side of my thighs just
below my ass as though he was straddling and planning to row us out naked
on his surfboard.  He lowered his cock into my hole.  He didn't lean
forward, but stayed sitting on my upper legs and I pictured him paddling
with his cock inside my ass, the two of us completely naked.

Eventually he lowered his upper body onto my back so he was lying on top of
me.  I still imagined him using his hands and legs to propel us forward on
a surfboard.

He then began to move his hips so his cock moved in and out.  He was not
long enough to hit my prostate but he was thick enough I could definitely
feel him fucking my ass.

The way the leg bands of the briefs were so low on my legs in the back I
could feel his balls pressing against my ass cheeks every time he pushed
down (me being so sensitive back there absent any hair made my feel every
little movement - I was loving being shaved back there).

He didn't get aggressive.  He just kept thrusting into me so he was buried
all the way inside me and his balls were nestled against my ass cheeks.

He tucked his arms up along my sides and wrapped his hands up under my
shoulders.  His smaller body on my back seemed to hug me as his hips moved
up and down.  As he thrust into me gripping me like that, my body seemed to
move as he shoved as far into me as he could go.

It didn't take him long before he started to cum.  I wondered if he was
imagining us being on a surfboard as I was because he was so gentle and
steady, like if being too aggressive it might tip us over.

I was so happy to feel him tense and change movements as he shot his load
into my ass.  I had let this boy lose his virginity.  I had gotten another
load in my ass.  And this whole surfer fantasy was incredibly hot (as was
the awareness throughout, boys were within earshot).

That I was getting satisfaction not from having an orgasm or great sex but
simply from giving a 14 year old boy the use of my ass should be disturbing
me.  But this was who I was now.  I wanted to bring boy's pleasure.  And I
loved that too.

I didn't care that word might be getting out that I could be fucked and I
was losing control of the situation.

He whispered in my ear "do I still need a haircut this weekend."

Damn this boy.  His cum was in my ass and his cock still hard inside me.
He knew he had the power.  And I had been fantasizing about him being a
surfer on my back and us on a surfboard.

"You get one more week," I said.  When the words came out of my mouth I
wondered if this was me reasserting some control or negotiating with this
boy.  If he fucked me again in a week's time would I let him have another
week reprieve.

Seemingly fine with the answer he climbed off me and said quietly in my
ear, "aren't you forgetting something".  I didn't even question that he
knew I would lick his cock after he fucked me.  I simply moved around and
licked him clean.

As he got dressed and left I turned on the TV and watched some mindless
reality show in my ass-less briefs, this blond 'surfer' boy's cum leaking
out of my ass and onto my bed.

If only he had sucked it out and fed it to me I thought.

Later, without even realizing I was doing it, I reached down to my hole and
scooped up some of his cum that had leaked out of my hole and brought it to
my lips.

NOTE: Nifty needs donations to provide these stories.
http://donate.nifty.org/donate.html