THE HEADMASTER
Well, it was the first `No' on my list. Age play. I was too tall for 12, but
maybe 15. I felt tight and terrified. The cream that Adam had rubbed into me
felt like it was pulling my sex into a new shape. I'd love to know what it was
made with. [Maybe not.] I had schoolbooks in my hand and the basic scenario in
my head. Long braids over my shoulders. White cotton everything. Shirt,
socks, panties, bra. Skirt of plaid in dark colors and black leather shoes
buffed almost patent. I felt young sitting on the bench on the third floor.
Before one of the `Specialty' rooms. The Teacher's Study.
Adam told me that this was Terry's personal room. He rented it and he decorated
it. He also told me that Terry used the other rooms on occasion. That was part
of the deal. I was to call Terry, Mr. Jensen, but I had no idea if that was his
real name or not. I had no real idea what he wanted. The door opened.
"Come in, Miss Hawthorne." That was my name in his crisp British accent. I
stood quickly.
"Yes, Sir." He closed the door behind me as I went to stand before the desk. I
noticed that he was dressed in a dark gray suit with a red tie. The room we
were in was like the movie set of a principal's office in an exclusive boy's
school. Huge dark- wood desk, green blotter, pen set and a small lamp. The
right edge had some type of smooth wooden sculpture at the back edge. A red
leather chair was set before it but I knew better than to sit down. Bookshelves
covered an entire wall. I looked down at his desk when he sat down. Noticing
that he had a report with a large red `F' on it before him. I hung my head.
"This is very disappointing." I kept my head down. "In all my years as
Headmaster here. I have never seen work as ill-prepared as this."
"I'm sorry, Sir."
"I'm afraid that I'm sorry just isn't going to be good enough this time. We've
had this discussion before, Anne." He was very stern and serious.
"Yes sir." I answered the very picture of contrition, but still dry as a bone.
The fear pounding in my chest should have had me dripping in nothing flat.
"Well, I'm afraid that we will have to deal very seriously with this matter. I
will be calling your father too collect you." He was reaching for the phone on
his desk.
"Oh no, sir. Please..." I pleaded, desperately. "Not my father, sir. I'll do
my work from now on..."
"I'm afraid that I cannot believe that, Anne. You've shown a decided lack of
responsibility so far. I feel that I have no recourse." I sat heavily in the
chair, covering my face with my hands, books in my lap.
"If I get expelled again. My father will kill me." I kept my face buried. A
couple of tears magically forming on my lashes, because if Terry thought my
performance was lacking, well... "Daddy" was Jon and I didn't want that to
happen. "Please, Mr. Jensen. Don't send me away from here." I let my braids
fall forward over my face. He was moving now. Coming around behind me. I
could smell his cologne. Light and airy. His hand fell on my shoulder, firmly.
"What would you be willing to do too stay here, Miss Hawthorne?" I looked up at
him through the tears and whispered.
"Anything, sir. Please." I didn't see any change in his expression. His eyes
were still coldly, clinical. Icy blue. His fingers flexing, once on my
shoulder.
"There is some sincerity in your plea." His eyes bored into mine. "Some
corporal punishment and maybe a personal attention for myself." I let my eyes
go wide in innocent shock.
"Personal attention, Sir?" He smiled as he stood over me. One finger going to
the bit of exposed collar bone at the throat of my white shirt. Delicate enough
to make me shiver with fear. His eye went hot.
"You know what I want, Miss Hawthorne." I felt palms start to sweat. I dropped
my eyes.
"But Sir, I've never..."
"All the better..." The hand withdrew.
"I can still call your father." I shook my head, no. "Then please stand." He
went to the door and locked it as I stood. "Now, remove your panties." I felt
my lips start to tremble, but knew that disobedience would not be tolerated. So
I lifted the plaid skirt and slid the white cotton underwear from my newly bare
pubis. The silken folds still dry. I prayed to God that I slicked up quickly.
If he fucked me dry. I'd be sore for a week. Terry was no small hanging man.
"Good posture, child. Hold the skirt up nicely. Eyes front." I let my chin
start to quiver. "Naughty girl, you did agree to anything that I wished, didn't
you?" I nodded.
"I just... didn't think..." I stammered in a pretty good parody of the nervous
young virgin that I was portraying.
"I will admit to taking advantage of your untenable situation, my dear. You
want to stay and I want to deflower you." He circled me checking my body over.
"It has been some time since I have had any sport or anyone in as desperate a
predicament as you." He ran his fingers lightly over my ribs until I quivered.
Tears threatening. "So, put your hands flat on my desk. I feel the need to
examine the well to which I will soon dip." I bent slowly at the waist to place
my hands on his desk. Letting him nudge my legs apart. His spread hand on my
lower back tracing the line of my hip to my buttock through the rough fabric,
squeezing. "You are so afraid of me, without reason. I like virgins, Anne."
One finger moved to my sex. He had to force it past the dryness. "What a
lovely honey-pink your young flower is. Dry with fear, which will only make it
harder for me to break. Try pretending that I'm the young gym teacher. Maybe
that will wetten your little pussy." I gasped at his crudity, quaking.
"Sir, please. Just get it over with. This is... embarrassing." A cane came
across my buttocks with sharp force. Moving me forward.
"I do not like impertinence." His finger circled my puckered nether opening,
which tightened involuntarily. "There are other ways for me to take you, bear
that in mind."
"Yes, Sir. I'm sorry, sir." I spoke quickly. No need to fake tears now.
"You paper was ten pages, so ten little strokes with my cane. If you are very
good for me. No moving or screaming. I'll pop your proper cherry. If you
resist, I use the less accessible opening. Do you understand?" I nodded,
energetically.
"Yes, sir." I heard the whistle and felt the fire spreading over my skin.
Cutting blows that I knew would bruise, but by Jon's rule, couldn't break the
skin. I wanted to move. Wanted to scream, but didn't, by some superhuman act
of self-control. I let the flow from my eyes fall unchecked for all ten blows
of the cane. Sobbing quietly when he was finished.
"Say thank you."
"Thank you, Mr. Jensen." He chuckled when I whimpered softly with misery. He
stood me up straight and moved me to the short couch. Sitting me down on the
leather, making sure my skirt was bunched up above my waist. Terry stood over
me and opened his pants. Letting his organ stand by itself from the hole in the
dark wool. He rolled a dry condom over the thick organ.
"Open your legs." I did and he touched my dry flower. "I have no desire to make
you bleed because of your fear. Take my penis into your mouth and wet it." I
shook my head, causing him to grab my braids with his fists. "If I fuck you
dry. You won't walk for a week, so open your mouth." I felt him pull me up
hard. His cock pushing roughly at my lips until I opened them.
Terry pushed his dick as far into my throat as it would go. I was so hot I felt
that I as going to come right there, but I was bone-dry. `How could I still be
dry?' It hit me abruptly and I knew the game then. I started to wet that condom
with as much saliva as I could produce.
Whatever Adam had rubbed into me had dried me up for awhile. The only lube that
I was going to get would be what I put on that rubber before he fucked me. I
got it good and damp. As much as I could before he pulled away from me.
Letting him lay me back with my head on the arm of the couch and my arms above
me. He spit into his fingers and rubbed the outer folds with the small wetness.
Not near enough. Coming up above me he rested the head of his penis against me
and thrust it in about an inch. It moved with a thick scraping feel into my
cavern. It hurt for the first time in a long time, having a cock go into me. I
didn't like the way it felt, not at all.
I arched up, trying to push him off me. The parched tunnel clenching against
his invasion. My clit swelled with pleasure, but I felt like I was being torn
in two by his organ. He murmured against my hair, but I couldn't make it out.
It was too low. I pushed harder and felt him take my hands into his left fist.
Covering my mouth with his other hand. I screamed freely then and it was
comfortably muffled.
"You rich little bitches are all alike. Come here and expect to be treated like
goddesses. Well, this is what you really deserve." His face had changed and
his penis had enlarged. Tearing forcefully into me. Rough as rape. My grotto
rent by his body. "You deserve to be underneath me." I nodded, hoping that he
would hurry.
Terry caught my chin. His fingers tight enough to get my full attention. He
leaned on me heavily and fucked me raw. Ignoring my tears, my pleas and my
struggling. Making no attempt to make it good for me. Not even seeing me,
using me for some fantasy release that only he was enjoying. I moaned and
cried, begging him to let me up, I'd be good. All to no avail, he was
relentless is his use of me.
When he finally came, bucking against my clit. I sobbed with pain. Exhausted,
yet grateful, when the last of his spasms shook him and he pulled out of me with
a brisk jerk. His shoulders stiffly erect. Leaving me in a pile on the couch as
he cleaned up. He came back to stand over me and order.
"On your feet, Anne." I stood up shakily. "I've got some oil to make you less
sore." He started walking towards another door. "Follow me." I did and he led
me to a bedroom. This room was done in the same masculine tones as the other,
but this was his room. The bed was your standard bondage four-poster. Two
fluffy pillows in the middle of it. "Up in the middle, face down, hips on the
pillows." I went stiffly and did as he asked of me. Sore in places that had
long ago ceased to ache after sex. I half watched him undo his tie. He removed
his jacket, and then rolled up his sleeves. Taking a big jar from the shelf
before coming to the bed. I twitched nervously. "Relax. This will feel good.
Just some nice cooling oil in your sore little flower." He tied me down and put
a silk hanky between my lips, rolling the skirt to my waist. "Just so you don't
embarrass yourself, by crying out as the pleasure comes over you. Then, if you
like, we can talk." I nodded my head. The first touch of the cool oil against
the lightly abraded flesh felt like heaven. His fingers gentle, kind almost. I
moaned into the silk hanky, a small sound of complete and total relaxation.
Easing into the feel of the bondage and the slickness of his fingers. Loosening
up because I could do nothing else.
This was heaven. Terry had the fingers of a pianist, molding, stroking the
edges. Pushing into the crevices. Pressing the G-spot deep inside me. The room
warm and my body relaxed.
"It takes a good girl to allow tears to flow when being taken that way. Your
little sex is red and swollen. No blood just abraded tissues. You'll be sore
in class for a day or so." He kept stroking me, avoiding my clit. "I've tied
you down to make it easy for to enjoy my attendance." He kept talking in a low
voice. "Sweet, bare. Tight. You have to know the ways of pleasure, because
you will be back into my bed whenever I want you." I shook my head, no. He
laughed. "Oh yes, I have you now. I can still call your father." I hung my
head. "I mentioned that I worked at a boy's school?" I nodded, feeling the
warmth spread with the path of his fingers to my ass. "I have a desire to open
that little butt of yours." I shook my head. "You have no choice, child, but
not, I think, today." Another prod. "Are you blue?" I shook my head and he
went back to playing with my sex. His fingers covered with a rubber glove.
"Wider legs and hold it that way." I put my body into the position that he
wanted. "You have to pee now, don't you?" I nodded and freaked when he laughed.
"I wouldn't." I shook my head vigorously. No, I won't. It would be much
easier if he would stop putting all that pressure on me up there with his
probing fingers. I rested, trying to get some of my strength back. Breathing
deeply in acquiescence. Submitting myself to his attentions. Deep gentle
strokes from his hand. Feeling the welcome wetness starting to flow, getting
slippery. Lovely. "Nice depth." He was talking to himself, not even thinking
of me beyond the fact that I was willing flesh welcoming his ministrations.
Then the unexpected happened. My vagina swallowed his hand, without pain or
pressure, or any resistance. My flesh merely accepted his. I held still in
surprise. My legs tightened into rigid blocks. I was awake now. The pressure
was incredible. Terry laughed, deep, richly resonant in the room. I heard a
knock on the door.
"Come in, Jon." Terry's other hand was resting on the small of my back. "Look
what I have here." I heard him walk over to sit on the edge of the bed.
"I wondered if she could do that."
"Pretty easy, but unplanned. She's a little too full for this." Terry rocked
his hand and I clamped down on the threatening flood. "I'd rather not have the
mess, but you may decide. There are other rooms here." Jon told him to hold on
for a minute and left the room.
When he came back he slid something under my hips and pulled the pillows out.
Wrapping towels around my legs at the knees.
"Nice welts, Terry." Big hands on the marks. "What do you want to do?"
Considerate of Jon to ask me what I wanted, but I knew he wouldn't. He let me
stay there and pant with lust.
"Let's fuck the piss out of her. Make her lose complete control." I rolled my
head trying to convey that I had no desire to make a mess like that in front of
anybody. It would be too humiliating, but they were paying no attention to me
beyond pulling the silk hanky from my lips so I could use my safe word if I
wanted too. "There are some other toys in the cabinet over there. Help
yourself. Nice selection of canes."
"I wanted to let her retain some dignity, but you can make her do whatever you
want her too. She's been a bit too sure of herself so far, so let's see if we
can make it go away." Another low laugh from Terry who rocked his hand. "She'll
do it if she comes, won't she?"
"Yes." It was all very practical sounding. "I know it's not what you planned,
but it could be interesting."
"Nice paradox. Pleasure or punishment." He slid in front of me and took my
face in his hands. "You are going to allow Terry to fuck the piss out of you,
or I won't let you come for a month." I whimpered, but said nothing beyond.
"Yes, Master." I didn't know if I could do it. Some things are too deeply
ingrained to be overcome. I was torn. Not soiling yourself was so intrinsic to
every person over three years old.
Terry had no such qualms. He started using his hand with a vigorous motion that
put more pressure on my insides than I could really stand. Jon sliding down to
play with my clitoris. Well away from the line of fire.
"You're going to do it, Anne. Because I tell you too. You crave the orgasm more
than any other person that I have ever had here before." His words were working
on me. Setting my mind on fire. Galvanizing the lust in my head to the fire in
my sex. I wanted too, but it was so hard. "Come on, baby. Let it go. It's
what we want. Then Adam will come and take you to the basement. Wash you and
dress you for the whip." The whip, that sounded nice. "Only if you do it. Lose
yourself to it. No whip if you don't." I tried then, but only managed to force
a drop from my body. I couldn't.
"Got a penny, Jon." Terry said, I had heard that term before but never as a
good thing. He put his hand under the front of my stomach, pushing from the
front and from deep inside me. Jon pushing on my love-button. I struggled
against it. The rising wash of feeling from my abdomen. So different from the
other pleasures that I had felt in my lifetime. A burning ache from the top of
my pubis to the depths of my bowels. Erotic urgency straining my self-control.
I was losing it and it panicked me.
Then Jon, pinched my clit with insistent rhythmic vigor. I clamped myself down
tightly, but couldn't stop the burning flow from within me as I pushed
insistently against Terry's hand, forcing it out of my vagina the way it had
come into it. Warm moisture flowing into the towels as I came and came and
came. Head up, jaw like iron. Low growls from in me, barely heard. I
collapsed into the mess, not caring about it. Horrified by my actions, however
involuntary.
They left me lying there. Spent with passion and humiliation. Sobbing into the
pillows. Trying to figure out what lesson I had been supposed to learn from
this, but to tired too. To miserable.
Adam came in with a laundry basket. He took the towels from beneath me. Making
me kneel on the floor as he cleaned up.
"Come on, Anne. It's alright. You did alright." I swallowed convulsively,
around the lump in my throat. I felt ashamed and irritated and hurt. It had
shown Jon something about my personality though. The significance of my actions
did not go past him without being noted. He saw quite clearly that I didn't
take humiliation well. I didn't take it well, at all. I struggled to pull
myself back together with tears choking me. Letting Adam take me back to the
bath chamber to clean me up. Once again.
