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The Vice Principal


Dan prepared for the evening with an air of confidence and
arrogance about him. He was nearing the end of his last year
in high school and, as with many of his fellow classmates,
he was feeling nearly bullet-proof. He was already accepted
to college and knew that virtually nothing academically,
short of actually failing a class, could have any impact
on him.

Oddly, as he seemed to care less and less about classes his
grades stayed the same or seemed to almost improve. It was
almost as if he had relaxed just enough to not get too nervous
for tests or too worried of failure. As the year progressed
he also had been getting rowdier and rowdier outside of
classes. His fellow senior team-mates on the football
team and he had started acting up more and more in school.
Nothing ever that would get them in serious trouble, but
certainly trouble enough that they were becoming an irritation
to some of the teachers and administrators.

The person they enjoyed bothering the most was Ms. Melissa
Hayden. Ms. Hayden was the newly appointed vice-principal
of the school. It seemed she loved going out of her way to
be a bitch or a bother to some of the students. At times she
seemed to unnecessarily come down on a student in what looked
like nothing more than an effort to try and prove to everyone
how tough she could be.

The feelings of Dan and his friends were no doubt amplified
by the sexual tension they all felt toward Ms. Hayden. They
all unanimously hated her, but there was no denying that
she was completely hot. She couldn't have been anything
beyond 35 but her soft, wrinkle free skin made her face look
much younger. She was taller than many of the boys in school
and probably would have been around 6' in bare feet.
It was hard to judge her height because Dan had never seen
her wearing anything other than tall, spike heeled shoes.

He and his friends suspected she wore the shoes to add to
her height advantage over the students, but there was no
doubt that the shoes added to her sexy appearance. She always
wore very appropriate looking skirts that came down to
her knees. They were never too tight, but were just snug
enough to show off the perfect swaying of her ass and hips
as she strutted down the halls looking for someone to bust.

Her tops were never very revealing, but she tended to wear
silk tops that buttoned up the front. The way her top clung
to her smallish tits and lean waist never failed to cause
a reaction in Dan's cock despite his hatred of her.
On many nights Dan stroked his cock thinking about how he
would love to get under Ms. Hayden's skirt and fuck
her until she begged for him to stop.

A few months earlier a rumour had run wild through school
that Ms. Hayden only acquired her job by sleeping with various
members of the school board. Dan was sure that it was a rumour
as it seemed the story grew and changed every time he heard
it. At first the rumour was that she had fucked the head of
the school board, but by the time the rumour had grown she
had let four of the members of the school board gangbang
her until they agreed to give her the job.

Some of his friends had become regulars at Ms. Hayden's
office after having been sent there either by another teacher
or by the "queen bitch" herself after she spotted
them doing something in the halls. There were a couple of
guys that had so often been in trouble that she had made them
her "assistants" after school as a form of detention.
She usually had them emptying garbage cans or collating
papers or other mind numbing tasks. Dan knew they only caused
trouble so they could be with her after school. It was true
they hated her, but the lust of an 18-year-old boy is far
stronger than his feelings of like or dislike.

Dan himself had a few run ins with Ms. Hayden. Once, he had
tried to sneak out of school one class early only to be caught
by her. She had scolded him severely and kept him very late
after school doing busy work as a form of punishment, but
Dan didn't really mind as he took every opportunity
to watch her walk or stare wantonly at her when she wasn't

Now it was a Friday night and there were only two weeks of
school left. He drove to school to attend what would be his
final high school dance. The truth was that the dances themselves
were usually pretty lame, but he and his friends often used
them as a meeting point from which to start the night.

He parked his car and noticed that the light was on in Ms.
Hayden's office. He wasn't surprised as she seemed
to live at the school. She was at every dance and would often
be seen on stage censuring the DJ's selections in music
or out in the crowd separating couples who she thought were
getting too "intimate".

This dance was perhaps even more lame than usual as hardly
anyone actually showed up. The beautiful night combined
with the end of school being so near apparently had everyone
thinking of things other than school dances. Dan was getting
ready to join some of his friends and leave when he made his
way to the restroom.

He stepped out of the restroom and was immediately greeted
by her overly stern voice saying, "Mr. Jenkins. I'd
like to see you in my office." He stared at Ms. Hayden,
dressed as crisply as if it was 8:30AM rather than 8:30PM
on a warm, Friday night. He felt the familiar jump of his
cock from his own lust.

"I, um, was just leaving, " he offered in response
as he tried to turn and leave.

"Now!" she commanded in a tone that made Dan
stop and meekly follow her down the hallway toward her office.
In the deserted hallway her tall heels made a loud click
that echoed off the lockers. He tried to figure out what
the hell she was doing and he couldn't help but stare
at her ass.

"Sit down, " she commanded after they stepped
into her office and she shut the door behind them. Dan looked
and saw one chair sitting in front of her desk and took a seat.
He looked straight ahead at the closed blinds as Ms. Hayden
began pacing and lecturing him. "Mr. Jenkins, "
she started, "I suppose you think I haven't noticed
all the crap that you have been pulling lately."

Dan stopped listening to her and merely stared straight
ahead as she continued her lecture. It was a couple of minutes
later when he became aware of her presence directly behind
him. The whole time she had been talking she had stayed either
to his side or behind him so he hadn't really been able
to look at her.

"Mr. Jenkins, " she said leaning over close
to his ear, "are you even listening to me?"

"Uh, yes, " Dan answered unconvincingly.

"Really?" she replied. "Well then, why
don't you tell me what I was just saying?"

" don't know, " Dan

"Typical, " she shot back. "You boys
only know how to think with one thing. If you spent half as
much time using your brains as you do worrying about your
dicks you'd be brilliant."

Dan jumped and spun around to stare at her. Did she just say
dick? His mind briefly fluttered with the various types
of trouble he could cause for her because of her saying that.

She remained silent and stared into his eyes with a stern
expression. She let him stare at her for a few seconds in
silence before she said, "Oh, did that excite you?
Did you like hearing me say dick?" She stared at him
as if she expected an answer. Dan didn't speak so she
repeated, "Did it excite you to hear me say dick?"

Her tone made it clear that he was to answer and he cleared
his throat slightly before whispering, "Yes."

"Typical, " she repeated before continuing,
"turn around and face front, Mr. Jenkins. I didn't
say you could look at me." Dan turned around and stared
at the closed blinds again unsuccessfully trying to keep
his cock from growing hard in his pants.

She remained behind him as she resumed her lecture, "I
know how you boys think. I know that all you think about is
fucking and getting in girl's pants. You'd be
shocked if you knew how much I knew about you all."
She paused and let Dan's mind spin as he tried to understand
what the hell was happening. "Hell, " she continued
as she leaned slightly closer to Dan, "I bet you even
dream about fucking me. Put your hands behind your back."

Her last two sentences were so shocking and had been spoken
so quickly that Dan wasn't initially able to comprehend
them and follow her directions. "Put your hands behind
your back, " she ordered again as he this time meekly
followed her instructions.

By now Dan was so confused and excited he could hardly think.
Was she coming on to him? Was he in trouble? What the hell
was going on?

He jumped at the touch of her hands on his forearms. She nimbly
manoeuvred his arms behind him and the next thing Dan knew
his wrists were locked in some sort of handcuffs behind
him. In his shock he briefly struggled against them only
to realize that not only were his wrists bound together
but that he was also bound to the back of the chair. He heard
Ms. Hayden laugh wickedly as he struggled.

The next thing he knew she was tying some sort of cloth around
his head and his vision was totally blocked. She let him
sit for a few minutes as she seemed to pace slowly around
the room. He could only hear the click of her heels on the
hard floor above his own excited breathing.

He heard her walk over in front of him and stop and he guessed
she was standing directly in front of him. He gasped when
he felt her hands at his feet. With the same quickness she
had shown on his arms she moved both of his legs and Dan heard
two quick clicks as his ankles were now cuffed similar to
his wrists. He wriggled briefly but immediately found
that his feet where tightly secured to the chair and he was
totally trapped.

He heard her stand up and she quietly, but sternly said,
"Now I expect you to remain silent. If you call out
I will swear that I had no knowledge of this and it will be
your word against mine. I will suggest that you and your
friends were playing a cruel joke on me and you and your friends
will be expelled. None of you will graduate and you will
all have to delay college. Do you understand me?"

Dan nodded dumbly and then heard her footsteps move away
from him and out of her office. He listened as they moved
down the hall becoming softer and softer until he couldn't
hear them any longer. In the silence of the office he again
struggled to free himself but couldn't.

Dan had no idea how long he was alone in the office but guessed
it was nearly 20 minutes before the clicking of her heels
let him know she was on her way back to him. She entered the
office and didn't say a word before she took hold of
the front of his jeans. She deftly unbuttoned and unzipped
his pants and, before Dan could really comprehend what
had just happened, she pulled his pants and boxers off together
in one motion. She rocked Dan from side to side working his
pants off until she had them pushed down around the cuffs
at his ankles.

Without a word or another touch she turned and left the office.
He again listened to her heels clicking down the hall until
she was so far away he couldn't hear them any longer.
He was vaguely aware that they sounded different this time
but figured that was due to his own heightened excitement
and anxiousness.

He sat now with his heart pounding in his chest and his cock
exposed to anyone who might wander by. What the fuck was
happening? What was she doing?

When he heard the voices from outside in the hall he froze
in fear. He could hear his friends walking toward the office
talking about where he had gone. "Shit, look at this, "
his friend Mark said, "fucking Ms. Hayden left her
door wide open."

Dan gasped in horror and he could feel his heart jump into
his throat. That bitch left him like this and then left her
door wide open! If his friends caught him like this there
would be no living it down.

"We should go in and trash the place, " Mark
said. Dan knew that Mark often liked to talk big like this
and he grew terrified when he heard someone, he guessed
it was Mark, start to walk into the office.

"What do you think you are doing?" Ms. Hayden's
harsh voice called out from the hallway. Whoever had been
walking in froze and immediately turned and retreated
to the hall.

Mark then weakly stammered, "I was just, I thought
maybe Dan..."

"You thought maybe Dan what?" Ms. Hayden sternly
said. "You thought Dan was hanging out in my office.
You never, under any circumstances, have the permission
to enter my office without my consent. Do you understand

"Yes, " Mark meekly answered.

"Good, " Ms. Hayden said, "now as far
as Mr. Jenkins. I don't know that it is any of your business
but I saw him leaving a while ago with another group. Now,
get away from my office."

Dan listened to his friends walking away quickly. How could
they buy the story that he left with someone else? Hell,
there wasn't anyone else there to leave with. Surely
they would see his car in the lot and know he was still inside.

Several minutes after they left he heard Ms. Hayden enter
the room again. This time she shut the door behind her and
said, "Your little friend almost had quite the surprise."

She moved around her desk and Dan could hear some rattling.
He heard her punch some buttons on the phone and sat listening
to her side of the conversation. "Hi hun...Sorry
about this but I'm going to be late...I know...I've
just got a project I need to finish...I'll make it up
to you...Love you."

Her footsteps moved around her desk and again stopped in
front of him. She pulled off his blindfold and tossed it
aside as he blinked a few times to get his bearings. When
his eyes focused on her again she was sitting on the edge
of her desk watching him closely.

He watched her pick up something off the desk and felt his
eyes widen in shock at the sight of what she held. It was a
fur covered paddle. The paddle itself was like one of the
old fashioned ones with the short handle and flat end that
teachers used to terrorize kids with in the old days. The
thing that made this one different is that it was coated
in a light brown fur.

She slipped off the desk and stepped close to him until his
bare knee was between her legs. She reached out with the
paddle and started rubbing the soft fur up and down his inner
thighs slowly. Dan gasped and stared at her still unable
to believe or understand what was happening.

The first time the soft fur rubbed against his cock and balls
he involuntarily let out a moan. Ms. Hayden smiled wickedly
at the sound and continued to tease his cock and balls until
he was rock hard.

From seemingly out of nowhere Dan felt his cum exploding
out of his cock as she rubbed the fur up and down his shaft.
He stared wildly as his cum surged out and coated the paddle
in addition to his own cock and balls. "What the fuck
is going on?" Dan thought to himself. Had he really
just been aroused by the idea of Mark sucking his cock? No,
surely it was only made to feel exciting by his particular
situation and by the touch of the fur on him.

Before he could think about it any longer Ms. Hayden said,
"That was your free pass. If that happens again before
you are instructed there will be hell to pay, do I make myself
clear?" As she spoke she firmly whacked the padded
against his outer thigh leaving a wet spot from his cum on
his red skin as she pulled the paddle away. She made it clear
to Dan that she intended to use the paddle if he didn't
obey her. For a moment he envisioned himself bent, bare
assed, over her knee as she paddled him.

She set the paddle down on her desk and began to untuck her
shirt. Slowly, and with a crooked smile on her face, she
began to unbutton her top. She pulled her top off and revealed
her cream coloured bra to Dan's excited, confused
stare. The smallish cups had lace accents at their top and
he stared wildly at her tits. He gasped in lust as she next
reached behind her and opened her bra before tossing it
behind her.

Her nipples seemed to immediately grow stiff once exposed
to the air and quickly stood out tall and tight on her tits.
They were definitely smaller than average given her height
but their shape was intoxicating. Dan wished he could reach
out and touch them but was quickly reminded of his helpless
state. She smiled at his obvious lust and took a few moments
to fondle her own tits teasingly. She pinched and rolled
her nipples between her fingers until they stood out amazingly

She reached up under her skirt and first pulled off her stockings
before doing the same to her panties. Dan knew she was now
naked with the exception of her skirt and his cock had already
started to rise. Ms. Hayden stared at his growing cock,
still coated in his own cum, and mused, "Ah, so predicable
but so wonderful."

With that she stepped even closer and lifted her skirt as
she lowered herself down until she was sitting on his thigh.
She was straddling his left thigh and immediately started
to grind her hips back and forth rubbing her excited pussy
over his leg. Dan groaned when he felt the wetness from her

She continued to slowly "hump" his leg until
his cock was absolutely rock hard and his leg was getting
wet from her juices. When she stood she looked at him as if
she was deciding what to do next. Suddenly she put her foot
on his chest and slowly began to push him backwards until
the chair was leaning back on only two legs.

Dan stared at her long legs and excited tits until he felt
the chair go past the point of balance and he started to fall
over backwards. Fortunately the one carpeted part of her
office was behind him. The thick throw rug did help cushion
the blow on his head but it still hurt quite a bit as he came
crashing down on his back. "What the fuck?"
he said as the chair came to rest.

"Don't you swear at me, young man, " Ms.
Hayden scolded. "If you would prefer I could leave
you like this all night. She waited to see if he would protest
and when he didn't she walked over to him and then straddled
his head. He lay looking straight up her skirt but he couldn't
see her pussy under its shadow. As she knelt down on top of
him she lifted her skirt so that by the time he felt her wet
pussy pressing on his face her skirt was up around her waist.

He tried to lick and kiss her pussy but she initially didn't
seem very interested in that as she instead began grinding
her pussy all over his face. She shifted her hips and gyrated
all over until his face was coated with a heavy layer of her
juices and Dan was gasping for air.

He had seen pictures of "smothering" on the
internet but hadn't ever given much thought to it.
Now he knew exactly how the guys in those photos felt as Ms.
Hayden pushed her pussy wildly all over his face only letting
him gasp for air occasionally. The act was so exciting,
so nasty, and so erotic that Dan was wildly excited. Coupled
with that was the intense frustration Dan felt at having
no control over what was happening. Somehow the frustration
only seemed to heighten his arousal.

Finally, Ms. Hayden settled her pussy over Dan's mouth
and he eagerly started licking and sucking at her. In truth,
Dan had very little clue what to do when sucking a pussy but
he was so excited that he simply began to lick and suck at
her with a wild abandon. For a while he didn't know if
she was enjoying it as she was completely silent but then
he suddenly felt her body tense as she pressed down on him
very hard.

Her pussy started to quake around his tongue and she began
grinding her hips roughly on his mouth as she moaned a long,
lusty sound. She stayed over his face just until she finished
cumming and then immediately stood up and looked down at
him wickedly.

"Well, Daniel. It seems you are quite the eager student, "
she said.

She lifted the chair off the ground until he was again in
the sitting position and then finally unzipped and removed
her skirt exposing herself completely to Dan's gaze.
He had never imagined that her body would be this hot even
in his fantasies. She clearly worked out regularly as her
body was toned and lean with strong looking arms and legs.
Despite the fact that she was now naked she still wore the
high heeled shoes further adding to her sexy appearance.

She looked down at his hard cock and then moved close to him
straddling his legs between hers. For the first time she
lightly touched his cock as she held it while she lowered
herself down. When she came to rest on his lap she released
his cock and he could feel it brushing against her periodically
as she sat looking at him.

He tried to lean forward and kiss her but she leaned away
until his restraints prevented him from going any farther.
For a while she teased him by acting as if she was going to
kiss him only to pull her mouth away at the last minute. This
was driving Dan crazy and she knew it. She shifted her position
and began to similarly tease him with her small, perky tits.
She held them just in front of his mouth but whenever he tried
to kiss, lick, or initiate any contact with them she pulled

He was so preoccupied with her teasing tits that he didn't
even realize her slight movements. Before he even realized
that she had moved he felt the tip of his cock brushing against
her dark pussy hair. He let out a long, deep moan when she
lowered herself engulfing his hard cock in her wet pussy.

When he was fully inside her she leaned over and put her mouth
right next to his ear. "Remember, " she said
softly but sternly, "if you finish before I give my
permission you will be punished." She stressed the
work "will" in a way that was simultaneously
exciting and a little scary. As soon as she uttered the last
word she slowly began fucking him causing Dan to let out
a deep moan.

As Dan was still moaning Ms. Hayden stopped fucking him
and gave him a stern look. "I am not kidding young man, "
she said. "You either control yourself our I will
really have my way with you." She grasped his chin
and lifted it so he was looking directly into her eyes. His
eyes were filled with lust and some confusion, but her eyes
were cold, calm, and steely as she looked down at him. "Do
you understand me?" she concluded.

"Yes, " he whispered.

"Good, " she said as she smiled at him wickedly.
"Now you be a good boy and do as I say." She resumed
her teasingly slow fuck as she lifted her hands up and put
them on either side of his face. She ran her hands slowly
up and down his cheeks before letting them slide down off
his face and onto his shoulders.

Dan let a soft moan escape his lips despite his trying to
stay silent. The way her pussy felt around his cock was beyond
anything he could ever have dreamed. Her touch was stern
but wildly exciting. He felt jolts of excitement surging
through him starting at the points where her fingertips
dragged over his skin.

She smiled devilishly and let her fingertips move down
to his nipples. She circled them a few times and Dan became
aware that his own nipples had become stiff. They certainly
weren't stiff like the women he had watched in porno
movies, but they were definitely tighter than he could
ever remember them being before.

Her fingertips slowly flicked the points of his nipples
and then her smile grew even wider as she grasped his nipples
between her thumbs and index fingers. Dan began to moan
but then quickly gasped in shock and pain as Ms. Hayden pinched
his nipples roughly. He stared at her with wild eyes as she
pinched him tightly and continued her slow fuck.

Dan yelped in pain again as she began pulling and twisting
his nipples. Hearing his reaction almost seemed to encourage
her and she began fucking him a little faster as she continued
pinching and twisting his nipples.

At first Dan couldn't feel anything except the pain
of her hands on his nipples. Slowly, however, that sensation
dulled a little and he became very aware again of her slick
pussy moving on him. As the sensation of their fucking came
back into his consciousness he became very aware that it
felt even better than before. She had changed her tempo
but he knew that wasn't the reason it felt so much better.
No, he knew that somehow the pain he felt seemed to amplify
the pleasure.

After a short while longer she released his nipples and
moved her hands up and over his shoulders until they were
resting on his upper back. Dan realized that he might be
able to reach her tits like this so he leaned his head forward
and tried to reach her nipple. Before he could reach it,
however, he became aware of sharp pains on his back.

He immediately forgot about her tits and groaned as he screwed
up his face in the wake of this new pain. He looked up at her
face but she seemed to be looking over his shoulder at her
hands. Her long nails continued to slowly rake across his
skin leaving long, red lines in their wake as she scratched

Dan again was flooded with the sensation of this new pain
but as that subsided he again became aware of the intense
pleasure of her pussy around his cock. As with before the
shocking mixture of pleasure and pain seemingly intensified
the sensation of their fuck.

Ms. Hayden continued raking across his back and Dan stared
wildly into her face and at her lean body as it rode up and
down on him. Before he even became aware of it, Dan felt his
cum start to rise out of his balls. He groaned and struggled
to control himself even though he knew it was hopeless.

He let out a loud moan as he started to fill her pussy with
cum. Ms. Hayden looked surprised at first as his cum exploded
into her pussy and then her expression quickly became stern
and harsh. It was amazing to Dan how much different this
expression looked on her face now. It was similar to the
look he had seen from her dozens of times before when she
was really pissed off about something. This time, however,
that same expression smouldered with lust and sexuality.
Dan stared excitedly into her face as he continued cumming.

When he finished cumming Ms. Hayden sat still for a brief
moment and then said, "Are you all finished now, Mr.

"Yes, " Dan answered quietly.

"You didn't wait for my approval, did you? Well, "
she said as she got up off his lap and stood tall before him,
"now I get to have a little fun." She moved around
behind the chair and Dan felt her unfasten his wrists from
the chair. They were still cuffed together but he was now
able to stand up when she took hold of his shoulders and pulled
him up. She repeated this with his ankles and left them cuffed
together as she released him from the chair.

She roughly twisted him around so he was facing the couch
and, before Dan could really get a feel for balancing in
his ankle cuffs, she pushed him forward roughly toward
the couch. Dan immediately fell to his knees and his chest
came crashing down hard on the couch cushions. His instincts
told him to try and break the fall but with his wrists and
ankles bound there was nothing he could do other than yell,
"Fuck!" when he hit the couch.

"Mr. Jenkins!" Ms. Hayden called out sharply.
She didn't need to say anything else as it was clear
from her tone that she was not pleased with his language.
Immediately afterward he felt the sharp crack of her hand
hitting his ass with surprising force. He cried out as the
stinging and burning on his ass almost seemed to intensify
as she pulled her hand away. "Anymore of that and you'll
be sorry."

Dan tried to turn around and see what she was doing but he
couldn't twist around far enough to see her. Judging
from the clicking of her tall heels he guessed she had moved
back over to her desk. He heard her open a drawer and then
heard her rustling around. He tried to shift his weight
so he could turn around even further, but before he could
turn his head around she sternly said, "Mr. Jenkins,
turn back around. You will turn around when and if I say so."

Dan did as instructed and stared straight ahead at the back
of the couch waiting for his punishment. His heart was racing
and he could feel the knot in his stomach as he waited for
her. He could hear her moving around behind him and eventually
he heard her footsteps move close to him and stop directly
behind him.

He expected to feel the harsh smacking of the paddle on his
ass at any moment. He fully expected that would be his punishment
after her earlier teasing of him with the fur lined paddle.
Or perhaps she would simply give him a bare handed spanking.
His ass was still stinging sharply from her single smack
and he wondered what it was going to feel like when she finished
with him.

Instead he felt her hands brush against his ass before she
reached between his ass cheeks toward his asshole. When
her fingertips made contact with his asshole he immediately
noticed the feeling of something cold and slick on his tight
hole. Her fingers worked up and down over his asshole and
Dan's mind raced with what was happening.

Her fingers moved away from his asshole and he immediately
felt her move closely behind him. It was like she was getting
ready to fuck him doggie style and then Dan realized that
might be exactly what she was intending. He gasped in shock
at the thought.

The next thing Dan knew he felt something else pressing
against his tight asshole. He was about to open his mouth
to ask her something, anything, but before he could say
anything she pressed whatever it was firmly against his

Dan felt his virgin asshole fight the intrusion for a few
moments before Ms. Hayden increased the pressure and finally
pushed the tip past his tight ring. Dan cried out in surprise
and discomfort as Ms. Hayden continued her slow but steady
penetration until she drove the full length of whatever
she had into him. He could feel her thighs pressing tightly
against the back of his legs after she finished filling
his asshole. Dan had no idea what she had just shoved up his
ass but it felt like he was about to be split in two.

After the initial penetration, the sensation wasn't
quite painful but it certainly was uncomfortable as his
ass was being stretched beyond any limits it had previously
known. Just when it seemed like she would pause so he could
adjust to the sensation she pulled nearly all the way out
of him and then started to fuck his ass at a firm, steady pace.

"Ohhh God!" Dan gasped as the discomfort became
more and more like pain again. He pushed his face into the
couch and was overwhelmed by the sensation of her fucking
his asshole. It seemed like his gasping and squirming only
egged her on and she continued fucking him even a bit harder.

Ms. Hayden let her fingers drag over his lower back and ass
as she continued to fuck him with the strap on dildo. She
fucked him long and hard not really too concerned about
his comfort or pleasure. She knew that he was young and would
quickly adjust so she focused on the amazing feeling of
control and power she felt as she reamed his virgin asshole.

It took a long while for Dan to get even remotely comfortable
with his new situation. He gasped and groaned in discomfort
over and over as she continued vigorously fucking his ass.
It was only after what felt like a near eternity that he began
to get adjusted to the feeling. Oddly, as the discomfort
went away he realized that he found the penetration enjoyable.

He had never even thought of his ass as anything erotic before
and never guessed it could be exciting. Slowly, his moans
became less and less out of discomfort and quickly grew
more lustful and excited. Ms. Hayden seemed to sense the
shift also as she asked, "So, Daniel, do you like this?"

"Ugh, yes, " Dan gasped in between her solid

She didn't say anything but began to fuck him even faster
and harder. Dan groaned and then gasped in shock when he
felt her hand coming down roughly on his ass. She continued
spanking him with her bare hand as she wildly fucked his
asshole. Again, the mixture of the stinging pain on his
ass with the oddly satisfying pleasure of whatever she
had shoved up his ass was amazing.

After a few minutes of this Dan again felt the painful raking
of her nails across his back. This time she slowly drew her
nails over his lower back and ass. Dan cried out as she raked
her nails over him. She continued alternating between
smacking his ass and scratching him with her long nails
for a while as she continued to thoroughly fuck his ass.

"Ohh, " Ms. Hayden moaned in what sounded like
pleasure, "Mr. Jenkins I could keep fucking your
sweet ass all night. Would you like that Daniel?"

"Yes, " he answered excitedly.

Time blurred for Dan from that point on. He had no idea how
long she continued to fuck him, but he did know that she had
to stop two times to reapply the lubricant. By the time she
got done fucking him it felt like it might have been hours
later. His asshole had now become completely adjusted
to the situation and he eagerly and excitedly was able to
relax and receive her fucking with growing pleasure.

Once he had time to adjust he couldn't believe how much
he started to enjoy being fucked like this. The feeling
of being completely controlled by her and being at her mercy
further stoked his desire. She again started spanking
him as they fucked and didn't stop until she was pumping
his ass roughly and his ass was bright red and stinging him
in pain.

She pulled out of him so quickly that it took him a few moments
to realize it had happened. He felt her hands on his shoulders
before she pulled him quickly off the couch and dropped
him on his back on the floor. He lay there and gazed up at his
vice-principal as she stared back down at him. From the
way his ass felt he expected to see her holding something
huge, but instead he saw her wearing a strap on dildo. He
stared up at her wildly and couldn't believe how hot
she looked wearing the strap on. What surprised him was
how small the dildo was. It was actually quite thin and probably
no more than four inches long.

"You like that, Mr. Jenkins?" she asked glancing
down at her "cock". He didn't say anything
so she asked him again in a much harsher tone.

"Yes, " he answered.

She dropped to her knees and then brought herself down until
she was sitting on his chest, moved forward and again brought
her pussy down roughly over his mouth. She was again smothering
Dan and he eagerly began sucking and licking at her amazingly
wet pussy. She started grinding her pussy all over his face
roughly and it only took a few more minutes of this before
she groaned loudly in the throes of an intense orgasm.

She stayed over his face for a few minutes just enjoying
the feeling of him squirming under her and the feeling of
his mouth at her pussy. When she finally stood she took off
the strap on dildo and tossed it aside. She looked down at
Dan's naked body and just let her eyes move all over
his helpless form. Her gaze finally stopped at his cock.
Through the excitement of the fuck and then of sucking her
pussy his cock had regained nearly all of its size and he
lay yearning for relief.

"I guess you've been a good boy, " she mused.
"I think I'll reward you." Dan groaned
at the visions of her fucking him or sucking his cock that
danced through his head. Instead she knelt next to him and
took his cock in her hand. She began to stroke him with a tempo
that soon had him going wild. She easily kept him in control
for a while longer and only seemed to let him lose control
when she was ready for it. She cupped his balls with one hand
and pumped his cock rapidly with the other.

It only took a few strokes like that before Dan cried out
and started to cum. His cum flew all over his stomach and
only when he was nearly done did some trickle out and run
down onto her hand. When he was done cumming she lifted her
hand to his mouth and began rubbing his cum on his lips.

"Taste it, " she ordered. "Eat the cum."
He opened his mouth tentatively and she shoved her fingers
inside leaving all the cum that was on her hand inside his
mouth. He swallowed it quickly as she looked down at him
intently. "There now, " she said, "that
wasn't so bad was it? Trust me, the first time is always
the hardest. The next time will be much easier."

She then immediately began to undo the cuffs on his wrists
and ankles. When he was free again he immediately reached
for his stomach as if to wipe off his cum. "No, "
she ordered, "leave it." He looked at her for
a moment as if expecting something but she dismissed him
by saying, "Now, get dressed. I think you know the
way out."

She walked behind her desk and sat down in her oversized
chair watching him get dressed. Before he left he opened
his mouth to say something but couldn't think of what
to say. Instead he simply turned to leave as Ms. Hayden said,
"Have a good night Daniel. By the way, if you're
thinking of telling anyone about this I would advise you
to think twice. Anything you say will be your word against
mine and I think we both know who would win that one. The damage
your false allegations would do would severely hurt your
admission to college, trust me. I would see to that."

He left in a daze and found a note from his friends on his car.
He thought about calling them and trying to hook up with
them but then he felt the wetness from his cum on his stomach
and decided to call it a night. Instead he went straight
home, stripped naked, and crawled into bed.

He could still smell her pussy on his face and could still
taste the remains of her in his mouth. He ran his fingers
lightly through the wet spots on his stomach and then absent
mindedly brought them to his lips to taste them. The taste
wasn't nearly as strong as it had been earlier but it
still sent chills down his spine as it brought back the memory
of her sexy body.

He rolled over to go to sleep and became aware of a dull throbbing
in his ass from the thorough fucking he had received. He
had to remain on his side as the long scratches on his back
hurt whenever they contacted his sheet. Still, the dull
throbbing pain he still felt only reminded him of what had
happened. When he finally did fall asleep it was one of the
deepest, most serene nights of sleep he could ever remember.

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that was quite a turn on!


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Irish Rose


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Way to go. Great story. The only woman in my highschool was
the nurse and the office secretary and she was married to
the "coach".