Date: Thu, 10 Dec 2015 07:02:29 +0000 (UTC)
From: Jack Notmyrealname <jacksta@ymail.com>
Subject: Perfectly, Beautifully Unapproachable (1)

Hey readers!  My name is John, if you're my parents or teachers.  If you're
my friend, I'm Jack.  This story is true up until the day where I lose my
virginity (yeah, I'm still a virgin).  Everything after that is just one of
my recent jerk-off fantasies.  I was describing it to my friend a while ago
and he said I should write it into a full story.  So here it is!

If you want me to write a sequel to this story, or write another one, or
tell you more about myself, or just want to talk, email me at
jacksta@ymail.com.

Perfectly, beautifully unapproachable
Samantha

There she stood.  Long, flowing blonde hair.  Perfect symmetric face.
Lovely pink lipstick.  Firm high tits.  Thin white blouse showing just a
bit of her stomach.  Tight white short shorts showing off a gorgeous ass.
Perfect, beautiful Samantha.  Talking and laughing beside her locker with
some other girls on the cheerleading squad.  Perfectly, beautifully
unapproachable.

I know she's not nice.  She spits on twerps like me.  Slaps us if she
catches us even glancing at her chest.  That's why I can never look long.
And I really shouldn't like her.  But I can't forget about her physical
perfection.  I should just call her a bitch, but instead I think I'd do
anything she asked.  If she told me to come to school naked to embarrass
me, not only would I do it, but I'd do naked jumping jacks in front of the
entire school.  Sometimes I hate myself more than I hate her... but those
tits...

Shit.  I thought about her tits too long and now my dick's hard.  And you
know, getting a boner in school is hard enough, but getting one when your
dick one of the longest and thickest out there just fucking sucks!  I can't
just hide it by putting it down a pant leg and carrying some books around.
Managing a hardon takes work!

And I'm sure I know what you're thinking!  What right do I have to
complain, the boy with the massive cock?  Well, if you must know, I'm still
a virgin.  I don't think a girl has ever seen my dick!  Not since puberty
started anyway.  In my mind I've fucked the entire cheerleading squad, but
in real life, having a big dick doesn't make jerking off all that much more
fun.  And the looks on my friends' faces when I change clothes facing them
on sleepovers is priceless... but that's still not good enough.  Right now
it's a nuisance.  Maybe someday in college I'll be the big man on campus
and the girls will all line up to take a turn riding the monster, but I'm
15 now.  No good thinking about things still years away.  Especially when
I'm trying to lose my erection during school hours!

Too late.  It's not going away on its own now.  I need to take care of it.
The boy's bathroom on the upper floor has the least traffic this period.
If I can cum in under 5 minutes, I can usually get out before any other boy
walks in.  That's really important because, if you hadn't guessed it
already, I jerk off at the urinals, not in the stalls like most boys!  I
check under the stall doors for unwanted company, then walk to the far
urinal and pull my dick out.  Already hard, I start stroking fast right
away.  No easing into this jerk off session!

I try to keep my mind off her, and on more sensible fantasies.  But I
can't.  I can't think about anything but ripping her top off and sucking on
her nipples.  Licking on down to her totally shaved pussy.  Rubbing my rock
hard cock over her pussy lips as she moans.  Pushing it inside
until... Shit!  Footsteps.  I freeze as another boy walks in and starts
peeing a couple urinals down.  Shit Shit Shit!  I know him!  It's Chris.  I
can't just wait for him to walk out because he might figure out what I'm up
to.  So I do the only thing I can do... I quickly tuck my dick up and
button my pants over it.  I really hate doing that, but it's the only way
to hide it when it's that hard.  At least I remembered to wear a longer
shirt that day!

So... I guess I'm off to the bathroom on the main floor!  This time I have
this!  The bathroom is empty and I'm only a few strokes away from cumming.
One more thought about her pussy and... mmmm yeahhhhhh.  Even the quicker
orgasms still feel amazing!  Six shots of cum dribble off my dick and land
in the bottom of the urinal.  Thirty seconds later, I'm shoving my
softening cock back in my pants, and I stroll out of the bathroom with a
sigh of relief.

I probably should fill you in on some details I left out about Samantha.
About why I spend so much time fantasizing about her, and not any of the
other equally pretty cheerleaders.  It's hard to picture sex when you've
never had it, especially with a girl you've ever seen naked.  Try to
fantasize about it, and you just end up picturing the last porno you
watched!  What makes Samantha different is that I've seen her naked.  Not
in person, of course, but in cell phone pics.  See, at the beginning of the
year, one of us twerps stole James's phone during a game.  Yeah... that's
her boyfriend, and yeah, he plays football.  Typical!!

But what we found on his phone was not typical.  Seriously, this guy must
want to be a porn star!  He had naked pictures of himself from every angle,
and maybe a dozen videos of him jerking off and cumming.  But that wasn't
the real jackpot we found!  Amongst the hundreds of pics of him naked, we
found a couple of her.  Tits, pussy, everything!  That moment was one of
the most magical in my life.  Seeing a girl you know naked for the first
time isn't something you forget!  And what's more, we found in their text
messages everything about their sex life.  They were discussing positions
and schedules and even the possibility of a sex tape.  So they were
fucking!  We weren't sure we believed they really were until we read in her
own words that she preferred reverse cowgirl over forwards cowgirl and that
missionary was getting boring.  Who knew!!

The last time we took his phone, we even found a couple pics of his dick
inside her pussy!  Every time we kept hoping for that sex tape, but it
hasn't happened yet.  But we keep checking.  We even took to calling
ourselves the Boys Under the Bleachers.  That name stuck even though we
don't actually steal phones by hiding under the bleachers.  We get them
from the lockerroom during the game.  Fortunately, their coach makes them
leave their phones in their lockers, and fortunately, he left his lock's
combo sticker on the lock, and fortunately, one of us spied on James to get
his phone password.  We basically have the whole game to look through his
phone.  We could even have a circle jerk in there, if only so many of them
weren't afraid of getting caught.  So we just pass his phone around and
remember what we saw for later.

So that's why I can't stop thinking about her when I'm jerking off... I can
picture her naked so easily.  Some day maybe I'll find naked pics of a girl
who isn't a total bitch.  But then I guess I'd feel guilty about it.  At
least with Sam, I want to punch her almost as much as I want to stick my
dick in her.  I want to slap her boyfriend too.  He's as much of an asshole
jock as she is a bitch cheerleader.  But I guess I don't want to stick my
dick in him as much, haha!

I really should get my mind off them.  It's late now, and I still need to
jerk off before bed.  Fortunately, tonight I can distract myself with porn.
My current favorite: those Russian porn videos where a guy rents his
girlfriend to pay his own rent, and has to watch a pretty rich boy bang his
girlfriend in his own bed.  I have no idea whether they're real, but it's
pretty hot assuming that they are.  Ten minutes later, I'm catching five
shots of cum in my hand.  A minuter after that, I'm wiping the sixth shot
up off the floor.  Two minutes later, I'm crashing naked on my bed.

The next morning felt very normal.  I should have guessed that it would be
a special day, but I didn't.  Morning routine was normal.  Squeezed in a
quick jerk off session in the shower.  Normal horseplay on the schoolbus,
uneventful classes.  But at the end of science class... there was a hand on
my shoulder as I was getting up to leave.  Of course, I knew who it was.
She sits in the row behind me, two desks to the right.  But I didn't
believe it till I saw her looking straight at me.  And she had a worried
look on her face.

"You're good at science, right?  You know all this stuff?"  It was weird to
see her talk to me, instead of looking down on me disdainfully.

"Uhh..." was all I could get out.

"I really need a tutor.  Do you think you could help me out?"  This was
surreal!

"Well... I guess..." I wasn't getting more coherent.

"Thanks!  Meet me in the cafeteria after school!"  She touched my nose for
a moment before walking out.

I sat in stunned silence for a minute.  I managed to reassure myself that
this was reality and not just my mind playing weird tricks on me, and left
the room.  But it was still all I could think about for the rest of the
day.  I couldn't tell you what any of my other classes covered.  And I
think I missed my friend making a joke at my expense at lunch about my dick
or jerking off or something.  When the last bell rang, I went straight to
the cafeteria.  And there she was... sitting totally alone at a table, with
her textbook and notes out.

I walked up behind her, but found it hard to work up the nerve to say
anything.  I probably stood there for five minutes just trying to control
my breathing.  But then she stretched a bit and saw me, and I couldn't
pretend I wasn't there anymore.  So I nervously sat down at the table, and
just let her talk.

"Hi, John."  Of course she called me what the teachers called me.

She rambled on for a couple minutes about how she was headed for an F in
science class and she'd get dropped off the cheerleading squad and could
even be forced to repeat the grade.  I almost smirked at the idea of her
getting the punishment she probably deserves, but then she offered to pay
me money.  Normally the idea of getting paid would be funny.  Most people
have no pity for the boy from a wealthy family who gets basically no
allowance.  But I actually had assumed up until now that she was just gonna
ask me to tutor her for free.  Like it was such a privilege to be around
her.  But no, this was actually serious.  She was in trouble.

At that moment, I had a thought.  And I summoned up all the courage I've
ever had in my life, and told her, "I can tutor you if you pay me, yeah.
But it won't be in money."

"Oh great!  I really need this.  But what do you mean it won't be in money?
It... ohhhhh," it suddenly dawned on her.

My mind was racing.  Did I really just ask her to offer sex for school
help?

After a moment, she continued, "But we can't do it here!  We'd get caught!"

Shit!  My heart skipped a beat as I realized that she accepted my offer!
She was such a slut she had already jumped to the idea of having sex
without even leaving the school!  I should have just fallen apart there,
but I held it together and kept going.

"But the upper floor of the library..." She knew what I was talking about.
The library had more bookshelves on the second floor, and nobody went up
there.  There were no computers, no group tables.  Just rows of books.  And
the librarians didn't watch that floor after school.  I should know... it's
been a last place resort for jerking off on days when the bathrooms were
full and there was a team changing in the lockerroom.

I took her by the hand and led her there.  On the outside I managed to look
calm and serious, but on the inside, I was going nuts.  Was I really just
minutes away from losing my virginity?  Was I gonna pull my dick out at
school so I could put it inside the pussy of the hottest girl I know?  Am I
just going crazy?

Maybe I was going crazy.  When we got behind the last row of books, I
immediately stripped completely naked, head to toe.  I must have totally
forgotten my normal caution, because I only paused to pull the condom out
of my pants pocket before tossing all my clothes aside.  I just stood
there, my 7.6" in length, 6" in girth cock pointing out straight in front
of me, harder than it had ever been.

"Oh... big boy!  You're bigger than him!"  Of course she had never thought
that a skinny guy could have a bigger cock than a football jock.  Typical!

She breathed in sharply as I walked up to her.  She was actually turned on!
I unbuttoned her shirt and attempted to take it off, but she resisted.  Of
course she cared that she could get away quickly if caught, but didn't care
whether I could.  And of course she didn't treat this like it mattered.  I
wanted to be naked because I wanted my first time to be as real as
possible.  But who knows how many times she had been fucked before!

I pushed those thoughts to the side.  I was gonna enjoy this as much as
possible, and I was gonna pretend to be as experienced as I could.  While I
unzipped her pants and pulled them down enough to expose her pussy, she
unhooked her bra.  I started rubbing her pussy with my right hand as I
leaned into her chest and started to suck on her left nipple.  I had no
idea what I was doing really, if you don't count all the porn I've seen,
but she sure liked it!  She started breathing faster and I actually felt
her pussy get wetter.  If it were possible, I would have gotten even
harder!

I rolled the condom onto my cock before leaning in to kiss her.  This was
the second time I kissed a girl, but it was way better this time, with my
cock just grazing her pussy!  She broke the kiss as I started to push it
into her.  She moaned a little each inch that went in.  My pubic hair
touched her shaved pussy lips, and I could only say "Wow..."

To our right came an angry whisper, "What the fuck!?!!"

James had caught us.  An angry jock was staring down at me, with my dick
visibly inside his girlfriend.  Now, you'd think that I'd panic.  But I had
never felt braver and more masculine.

"Sup, dude?"  I asked casually, while slowly withdrawing my dick.

He looked even most pissed, but turned to her.  "What the fucking jesus
christ are you doing with this little bitch??"  I wasn't really offended by
the little bitch comment because I had pulled my cock all the way out, to
rest against her pussy entrance, so he could clearly see that I was bigger
than him.

They had an angry whisper fight for another minute while I stood there
naked except for a condom.  He lost the fight the moment she threatened to
skip their sex night that weekend.  She told him to go stand guard, and he
reluctantly did so.

Wait.  If she normally manipulated him with sex... did she think she was
manipulating me into giving her free tutoring?  What a ridiculous thought!
But no time to think that through.

I started to push my dick back in her.  I paused for a moment when I was
fully inside her again to enjoy her pussy squeezing the entire length of my
dick, then I started to thrust.  And with every thrust, I got faster.  The
warm insides of her pussy rubbed against every inch of my cock as I reached
the deepest point, then I would pull out so just the head was inside, then
slam it back in.  I was in heaven the whole time, my dick exploding with
some of the greatest preorgasmic pleasure I had ever felt.  After just over
5 minutes of pounding her, my orgasm rolled over me.  I moaned at full
volume as the feeling increased to one of the longest and hardest cums I've
ever had.  My god, that felt amazing!  And I was enjoying losing my
virginity the way I always meant to.  Even if it had to be standing up!

I looked over at James.  Sam and I were sweaty and breathing hard, and
James had an obvious hardon that he was trying not to play with.  My
bravery keeping up, I slipped my cock out of his girlfriend, and walked up
to him.  I ostentatiously removed the condom in front of him, took his hand
and folded the condom into it, and touched him on the nose the way she had
touched me earlier.  He glared at me, but did nothing.

As I went to get dressed from my clothes on the floor, he dutifully knelt
down in front of her to bring her to orgasm.  Fifteen minutes later, he was
gone, and she joined me at a study table on the lower floor.  I held up my
end of the bargain, reteaching her the material she needed to know.
Honestly, I'm probably not the best tutor she could get here, and it's
really good for me that she doesn't know that.  Because we both knew that
me fucking her was the cost for *every* session.  Maybe it was even good
that I was only okay at teaching, because that meant I'd be tutoring her
for a very long time.  Tutoring her in her bed... in her boyfriend's
bed... maybe even at school again!

As she was packing up her books, I got a text message, "yo dude this
sux. usualy i get to blow my load b4 i gotta eat her out!  wtf shud i do?"
I had no idea how James even got my phone number.

I took that to mean that he didn't bring her to orgasm while fucking her
either.  That was a relief!  I didn't want him to be superior to me in any
way today.  But I held back on taunting him, and just texted back a jokey
offer to give him a handjob the next time i saw him.  He probably didn't
even realize what was in store for him.  Of course I was gonna make him
watch next time.  Make him watch my giant cock stretch her pussy more than
he could stretch it.  Make him watch my ass flex as I push into her.  Make
him listen to me moan loudly in orgasmic ecstasy while pumping cum out.

And you know what?  One of these days I'm gonna make him film it on his
phone.  Maybe after I get some more practice fucking.  Then someday the
boys who have never seen a girl naked in person will borrow his phone and
see what's recorded on there.  And I'll be fucking the hottest girl in
school, rubbing it in the nose of the jock we hate the most, and I'll be a
sex god to all the Boys Under the Bleachers.

So yeah, there ya go, my first story ever.  If you want to see more, let me
know at jacksta@ymail.com.