The Head Mistress

head mistress sitting with a crop

The young man strolled down the hallway of his college with a smirk of self-
assuredness and confidence. That was on the outside, inside he
quivered in excitement. He went into the office of the Head Mistress
of the small college he attended. He reported to the lady at the
front desk and leered at her openly. She was not impressed. She
showed him into the Head Mistress’s office and shut the door. Once
inside, he saw her seated behind her huge Oak desk, looking at what
he presumed was his file. He stood cockily, hands behind his back.


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She said, “Sit down. I’ll be with you in a moment.”

He sat in front of her and put his hands in his lap nonchalantly. He
did this to hide the nervousness excitement that he knew would show
if he didn’t cleverly disguise it. He could never tell what she was
thinking, and it excited him to no end. She was always so
unpredictable, always so stimulating…

She finally spoke in that calm, collected silky manner, “So Mr.
Skipworth, you grace my office once again.”
She said patiently, her eyes reading his latest infraction.

He licked his lips nervously in great anticipation. She came around
the desk and perched on the edge, and as always ignored him as she
read. She wore black slacks and a very sheer white silk blouse with a
black bra under it. It did nothing to hide those marvelous round
titties.

She finally looked up and took off her glasses. She looked at him
with those emerald eyes that never failed to send shivers all through
him and made his cock stir in his jeans. He knew it was coming, and
that it would be delicious. He could tell by the look in her eyes.
“Selling Scantrons to other students, and in Math no less. What do
you have to say for yourself this time?”
She said in that voice that made his heart skip a beat.

He faked indifference and folding his hands behind his head
retorted, “I wanted to make some money. Sue me”

His heartbeat quickened, for there it was…that slight flicker of
the danger in her eyes and in that minute’ cat-like smile.
She rose to walk over to him and he stood up, looking down on her.
He could have easily done her harm for she was so damn petite and
little, but he would never dream of that. She was just so damn
exciting.

She said in a flat voice, “Sit down Boy”
He sat without hesitation, and she walked around behind him. His cock
was beginning to grow harder in his jeans.

She dug her long nails across his neck and said as he
shivered, “What am I going to do with you, Young Man? You don’t seem
to wish to do what is right; you constantly disobey, and are a
perpetual problem.”
She came around the front to stare down at him.

Her green eyes narrowed and she said in that hypnotic voice, “You
like to think that you are in complete control, don’t you, Boy? You
like making people think that you are a strong individual and that
you are always in charge of your life”

As she said these things she was moving closer and closer to him
until she was mere inches away from his face, and he could see the
gold flecks in her eyes. She smelled so damn good, too! She bent as
if to kiss him, so he put his mouth up to meet hers. She swiftly
pulled his head back by his long hair and gazed into his startled
brown eyes.
“Well. We are going to see just how much control you Really have, Big
Man. We’ll see if you have what it takes”

She licked up the side of his face with that marvelous tongue then
threw his head forward. “Now get up”
She pushed him over to the high open window that overlooked the
campus. This window was about mid-sternum to him.

“Do not move until I tell you that you may, do you understand? I want
you to face your peers. You are always in the limelight, and in full
control. I want you to remain that way that you are now. You will
wave to your peers, you will smile and don’t you Dare once falter.
Do you hear me, Boy. Answer now!”
She said in that low calm voice.

He panted, “Yes Head Mistress, I hear you”

Oh God, what did she have up her sleeves? He wondered. His cock was
rock hard in readiness, and throbbed painfully to his heartbeat.

She stood behind him where no one else could see her slight form. She
squeezed his ass cheeks roughly. “Don’t you dare change expression,
or your looks, not once, or it shall be extremely painful I assure
you!”
She then reached under him to fondle his cock and balls. She made him
put his hands on the sill then kicked his feet apart so that he
stood firmly planted, but slightly off-balance if he didn’t remain
so. She reached down and unbuckled his belt, and unzipped his jeans,
pulling them down over his hips. No one from down below could see any
of this happening. All they could see was the boy leaning on the sill
looking outside. She bit his ass sharply, hearing his intake of
breath. She slipped down onto the floor to stroke his hardened Man
Meat. He was rock hard for her. She could see his face from her
vantage. He was handling this well…thus far.
She rose up a little and began licking his throbbing cock. He twitched and
drew in breath over his teeth as she nipped his balls hard enough to
make them sting.
“Wave to all those that you know, Mr. In Control”
She commanded as she slipped her mouth over his large cock, swallowing as much as she could take it.

He waved at a couple of guys from his Gym Class. Lord, if they only
knew what was happening to him right now. Damn her mouth felt
marvelous! She too him in deep just for a moment, then moved back
again, just placing his cock head between her lips. She sucked and
lapped at all of the pre-cum just like a kid would lick an ice cream
cone. He shivered in delight. She sucked him hard for a few moments
and he was having a hard time concentrating on his task. A couple of
times she pinched his balls sharply.
He squirmed and managed to wave to the Dean of the College with
slight difficulty. How much more of this could he stand? She mused
with a grin.
She moved easily out from under him and removed an object from
inside her desk.
“Stand fast, don’t move” she ordered.

His legs were getting tired, but he would not disobey her. He could
hear her behind him, and curiosity was killing him. God, what was she
doing back there!?
He felt her fingers on his ass once more. Oh, how he loved this.
Her small fingers were warm and soft, but strong and firm. She put
her full, soft breasts up against his back, rubbing them
slightly. “Do you feel like you have full control now, Little Man?”
She purred.

Faking bravado he answered, “Sure. I’m always in control. That’s how
I win” He smirked.
“Goood” She answered quietly, “I’m glad you feel that way”

She tugged his jeans down until they were around his ankles, then
made him back up a tad, and lean further on the sill, bracing himself
on his elbows. It was a relaxed-looking gesture to anyone seeing him
from the quad below. She stepped back then was quiet for a few scant
moments. She then reached under him and caressed his cock until he
felt that he was going to burst. He then heard the “Swish” sound well
before he felt the white-hot lash fall upon his naked ass. It was the
sound of a Mini Cat of 9 tails as it struck sweet virgin man flesh.
The blow wasn’t meant to hurt, but it took the boy off guard, and was
so unexpected that he cried out lightly. He started to turn, but
found her at his back, hands again gracing his ass cheeks. It tingled
where the rawhide had struck, and he had felt it throughout his whole
body! It felt so wonderful–what had she done to him?

She said quietly, “Remember, control at all times My Boy. We shall
see how much restraint you have. Don’t you dare move, don’t you
dare react any differently than you have been”

She disappeared briefly, then he felt her hands underneath him again.
Shivers ran his entire body. She was sitting under him again. He
sucked in a breath as he felt something wrap around his cum filled
balls. She had wrapped one of the rawhide tendrils around his cock
and balls and was now pulling it off slowly. The sensation made him
want to gasp or moan, but he looked down to see her face. She seemed
as if she were taking great pleasure in this.
His hands dug into the sill as her hot moist mouth touched his
swollen member once again. He gritted his teeth so hard that it could
be heard. Her mouth was like hot silk. He closed his eyes for a
second and moaned slightly. That was a large mistake.

So swiftly that he had no time to think, the lashes caught him from
beneath him, and the exquisite sting traveled from his ass up to his
back! He bit his lips as she did this several times in sharp
succession, all the while sucking on his blood-engorged cock. He
quivered, thinking that he was going to explode all down the back of
her throat at any second now. She suddenly brought the whip up
sharply, and it struck him on the buttocks hard! He nearly passed out
from the feeling this created, for he had never felt anything so
good. He nearly collapsed on top of her. He felt her move again to
come up behind him again.

Once again she brought the whip down, again in a rhythmically erotic
cadence, until he just knew he was going to cum all over the wall in
front of him.

She stopped. She knew he was close for his head was thrown back in
pure pleasure. She ordered him to close the window, then turn to face
her.
There was something in her eyes that he had never seen before. She
spoke calmly, “Now Skip. We’re going to see how much restraint you
actually have”

She bade him come closer and as he shuffled close, she reached back
and freed her Platinum white hair. It touched her shoulders
beautifully. This took him totally by surprise. She removed her high heels, then undid her slacks. She lay her slacks on the chair. She had on white silk thongs that showed off her magnificent little ass. She unbuttoned her shirt, revealing her black bra and soft, milky breasts.
He couldn’t believe this, the Head Mistress standing there before him
in this manner!?

She walked up to him and rubbed his straining cock while licking her
lips, her lust-filled eyes looking up at him. “Come” she ordered
him and walked over to his desk while firmly pulling on his cock.
She did something that he never expected in a million years– She
handed Him the whip!
She turned around and bent over the big desk, and looked at him over
her shoulder.
“Now Boy, you will use my own toy on Me! You just lay it over your
wrist in a flicking motion, letting it fall on my ass cheeks. How
hard is up to you? How many guts do you have? How much restraint do
you possess? Do it now”

She turned her head and waited; pushing that tight looking little ass
out further. He stood in disbelief. Mar those delicious cheeks!? Oh Lord, he
thought. But…she had commanded him to do so.
He put the whip back as he had seen in the movies, and let fly! It landed much harder than he had planned, but the sound of the leather meeting that unspoiled flesh was wonderful in that tiny room. It hit so hard that it left red
welts all across her tiny ass.
She drew in a breath and he cringed inside, afraid that he had hurt
her. Instead, she curled her slim fingers around the edge of the large
desk and said, “Proceed”

He thought to himself, “Alright. You want it, you’ll get it!”

He flicked it again and watched it redden her skin. The more he did
this the more aroused he became. His member felt like it would bust
every time he lashed her ass.
Not a sound did she make until he began to lash her ass in the same
rhythm that she had used on him. She suddenly let out a strangled
gasp and dropped her head back in ecstasy. He came up behind her
closer and flashed the whip again. Her fingers scraped the top of
the desk, her nails scratching the wood.
Before he knew it he was pressed up against her, his cock against her
right leg. She reached back to take him in her hand and began to jack
him. Ahhh, he moaned in her right ear. His right hand began fondling
her breasts and his left edged down to fondle her pussy in the front.
He rubbed her clit as she jacked his hard cock. He lay the whip down
and used both hands on her pert breasts. She moaned and rested her
head back on his chest. “Ohhh, so good,” he moaned.

This was so forbidden, fondling an Administrator of a College this
way! And her tiny ass against his cock felt so fucking good! He bit
into her neck in bliss and was rewarded with her pushing that ass
back against him. She then moved her ass cheeks against him.

It was then that he felt it! She had grabbed the whip with her left
hand and whipped it around their bodies, lashing both of them with it
as they were pressed together. It slapped against their thighs and it
nearly sent him into fits of passion. He dropped his left hand and
shoved aside the thin material of the thong to diddle her soaked
pussy roughly. She yelped out quietly as his finger slid inside. He
had her steaming pussy in one hand as the other was pinching her
sweet titties. He was in sheer heaven. She arched her back and with
the next blow he dug his fingers into her love hole. She moved her
ass back against him, a cry finally coming from her lips. She
continued to lash them from side to side until he grunted
out, “That’s it Baby, come on, let it go. You don’t have to be in
full control All of the time. Let it go, that’s it.

He said things like this over and over until he couldn’t take it
anymore. He moved in behind her, and yanked on the thin material of
the thong. It ripped away from her body, and he grasped her slender
hips to thrust his big cock into her tiny tight pussy as she
continued to lash them both. She was so tight that it was difficult
to get in all the way, but he shoved in hard and finally buried
himself deep inside of her pussy.
He pumped her pussy, and she kept on swinging the whip; first to one
side, then to the other, He grasped her thin shoulders, then shoved
her down flat on the desk as he pounded his cock into her. He had
her down on top of the desk, helpless under his fucking.

She brought the whip up over her shoulder, and it landed on his left
shoulder. The sting it caused his cock to swell inside of her, and
he bottomed out inside of her purposely. She snarled and lashed
again. He rutted and pounded until she yelled out as her orgasm
racked her small body. The lash still swished on them both. He grit
his teeth, and with one last bone jarring thrust filled her tight
pussy with what felt like buckets of cum…..
He held her so tight that she could hardly breathe. When the spasms
of lust ceased, she lifted her head and chuckled, “Unhand me, Boy”

He let go and stumbled backwards.
With out a word, picked up her clothes and walked to the bathroom. He had pulled up his jeans and sat on the edge of her desk, smiling
at the scratch marks there. Her nails had dug in deep….

She returned fully composed, her hair back in her normal French twist, her slacks and blouse looking untouched as if nothing had transpired.
She put back on her glasses, and wore her normal expression. She
sighed as he started to reach for her.

“No. Do not get used to this, for it won’t happen again. You have a whole summer to contemplate what happened here tonight, Skip. Hopefully it will make you think.
Had it taught you anything at all? Had it taught you restraint, had
it taught you any discipline what so ever? It is now time for us to
go, for both of us must get home, and start our spring break.
What have you got to say for yourself, Boy?”
She asked; eyes cold as usual, but now with a hint of mischief there.

He just grinned and stated, “Next semester is going to be great!”
She laughed for the first time, “Skip, what AM I going to do with
you?”
Take me home with you?” He grinned.

Last Updated on 3 weeks by pseudonymous

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