Date: Thu, 12 Apr 2007 19:25:41 -0400
From: bigassfkstick@aol.com
Subject: Pembroke Academy

The following work is pure fiction. It does not in any way depict actual
occurrences nor are any characters based on any persons, living or
deceased, and any similarities to any real life events are purely
coincidental. In addition the material contained within is of a sexual
nature. If viewing such material offends or is illegal in your country or
community please exit this page immediately. That said, if you enjoy this
work I?d love to hear your comments and/or suggestions for future stories
or installments. Please forward any remarks to bigassfkstick@aol.com with
the title of the story in the message header. Thank you and enjoy!

The Pembroke Academy ? The Precursor Story
by Daddy ?Mac? McKenzie

The Pembroke Academy or more precisely Miss Pembroke?s Academy for Wayward
Girls would later be founded in 1987 by myself and named in honor of great
friend and colleague of mine, Mistress Maxine Pembroke. I was introduced to
Mistress Pembroke some several years prior when another good friend and
sexual partner of mine, Jack Richardson called in hopes I would join him
and another for an evening of erotic pleasures. How could I refuse such a
tempting proposal? Unfortunately I was busy but my friend wished my
presence so arrangements were made for the same time the following
week. Here is the story of how I first encountered Mistress Pembroke.

I arrived at the address Jack gave me almost an hour late as I had to stay
late at work to take care of a few last minute details. I rang the bell and
moments later the door swung open and there was my friend, Jack kneeling in
the entryway in a French Maid?s uniform, complete with garters and hosiery,
a blonde wig and full makeup. I almost broke out in laughter at the
spectacle having never seen this side of my friend before. I also took
notice that my cock became instantly aroused. A deep yet feminine voice
from the other room came. ?Jacqueline, has our guest finally arrived??
?Please take his coat and the two of you come join me in the parlor.? I
handed ?her? my coat, snickering as I watched my friend attempt to navigate
down the hallway walking on ?her? knees. I entered the room and stood
before an older but very attractive ?woman? and Jacqueline, still kneeling
and two steps behind me introduced me to Mistress Maxine Pembroke. Mistress
indicated I should be seated on the couch beside her while Jacqueline was
to stand up and go bend over a small bench on my left with her upturned
bottom facing towards the two of us. As it turns out Mistress Maxine
Pembroke was better known as Mr. Maximilian Donovan, a wealthy and
respected business owner from our community. I recognized the name right
away having seen it mentioned many times before in the weekly business
section of our local newspaper. Mistress Maxine poured us both some coffee
while we chatted awhile, both of us ignoring Jacqueline and her cute
derriere on display sticking out so provocatively. The conversation was
just small talk, nothing in particular, its only purpose to make
Jacqueline?s wait that much more intolerable then after twenty minutes or
so the topic of our verbal repartee turned to Jack/Jacqueline and our
encounters prior to that night and the various bondage and discipline games
we?ve played out in the past. After almost an hour discussing our periled
heroine we set down our empty cups on the serving tray and approached the
firm ass flesh on display framed so picturesquely by the delicate black
skirt with its white lace trim and a pair of very feminine pink satin
panties pulled down just below Jacqueline?s exposed boy parts. Getting down
to the business at hand, Mistress asked that I assist her affixing the
leather straps anchored to the bench around Jacqueline?s ankles, thighs and
wrists leaving the lovely ivory globes perched before us that much more
vulnerable and exposed. Mistress Pembroke then opened a small wardrobe to
the left of the whipping bench and removed a bright red rubber ball gag
with black patent leather straps and with one hand she reached behind
Jacqueline and pinched her bottom hard eliciting a little yelp from the
hapless slut, opening her lips wide enough for Mistress to properly place
the gag and affix it into place. Returning to wardrobe this time she took
out a wood handled hairbrush and stepped into Jacqueline?s view tapping her
left palm with the flat side. Mistress Pembroke?s hairbrush was of fine
quality with a nice hardwood handle about an inch thick with a comfortable
contoured handle which fit the hand quite nicely with an oval face about
four inches wide and six or seven inches long before it tapered to the
handle. ?Would you be so kind as to have the honor?? Mistress Pembroke
asked as she handed me the brush. ?Why certainly ma?am, I?d be delighted.?
I quickly replied. ?Give her bottom a good warming, twenty minutes should
suffice.? Mistress Pembroke added ?And be firm but not so hard just yet,
we?ll be giving her a good caning in a bit and I?d hate for the lovely
welts it produces to not be clearly visible.? At that last remark I heard a
little muffled moan come from Jacqueline?s gagged lips. ?You may begin
now.? Exclaimed the Mistress as she glanced at her watch ?I?ll tell you
when to stop.? I quickly found a nice steady rhythm, alternating left to
right as the pale ivory flesh turned slowly crimson, occasionally landing a
good swat between the twin globes upon the twitching brown flower at its
center, each time eliciting a delicious whimper from poor bound
Jacqueline. Again glancing at her watch Mistress indicated to me to stop,
landing one more blow delivered purposely with considerable more force than
the other to the tender swollen anus before handing the hairbrush back to
Mistress Pembroke to place back within the wardrobe cabinet. Mistress then
excused herself and walked from the parlor down the hall into another room
somewhere in the back of the residence.

Moments later Mistress Pembroke returned with a large 2 quart enema bag
filled to the brim with a mixture of mineral oil, liquid soap and glycerin,
warmed to approximately 110 degrees Fahrenheit. Mistress quickly fitted the
nozzle into Jacqueline?s rectum and released the clamp from the hose
allowing the warm liquid to flow into the sore red paddled rump. The bag
emptied after only a few moments and Mistress removed the nozzle and
whispered into Jacqueline?s ear ?You had better not spill a drop on my
beautiful floor my dear or I will take my cane to your nice big ?clit? as
well as that naughty promiscuous ass.? Mistress then released poor
Jacqueline from her bonds at a very leisurely pace. Jacqueline shifted her
weight nervously from foot to foot, the look of concentration on her face
as she struggled with all her might to contain the fluid within. Jacqueline
stood with sweat pouring from her brow, finally relaxing when Mistress
finally said she may go use the upstairs toilet with a sharp smack to her
right bottom cheek. ?I?ll be up in a moment to check on you and I?ll be
examining my floor so you had better be careful or those marbles in your
sac will be the size of bowling balls when I?m through!? ?Mr. McKenzie, if
you would be so kind as to wait here. We?ll return in just a few moments.?

Shortly they both returned from upstairs to the parlor as I joined them and
followed Mistress Pembroke as she pushed Jacqueline down the hallway ahead
of us. Jacqueline is now wearing only a skimpy pair of pink silk ladies
panties, her big clit almost bursting the front seams. At the end of the
hall Mistress instructed Jacqueline to open the door on the left and walk
inside. I grinned at the Mistress as she turned on the light and I spied
all the wonders within. It was a rather large room with three plastered
walls painted a beige color and the back exterior wall was unfinished
stone. Two large columns supported the vaulted ceiling and there were
several hooks imbedded in the columns where ropes or chains could easily be
attached. Mistress fetched leather bracelets and anklets and deftly affixed
them to the alluring Miss Jacqueline then chained her spread eagle between
the two columns. First Mistress retrieved a rather flimsy tawse, similar to
others I?ve seen except this one was made of soft deerskin. In my mind I
was confused by this choice knowing from my experience such an implement
would not cause much sting or impact. I thought otherwise as the Mistress
walked in front of poor Jacqueline, pulling down her panties just below her
rising organ. Once freed from the confines of the thin material Mistress
Pembroke expertly manipulated Jacqueline?s dangling bits until it stood out
nice and proud then cinched a leather band tightly about the base of the
sex causing it to swell a bit more and ensuring it would stay erect as long
as she desired it to. Mistress then raised the strap over her shoulder and
brought it crashing down with all her might upon the tender, defenseless
cock. Had Jacqueline not been gagged the screams would?ve been deafening
and tears began to well up almost immediately. The next swing was
underhanded catching the poor dear square across the marbles and again the
look of anguish & terror in Jacqueline?s tear streaked face was
exquisite. For five minutes this stern looking ?woman? beat the cock and
balls hanging so provocatively before us unmercifully. When she had
finished Jacqueline was dripping with sweat and her color turned somewhat
pale. Mistress meanwhile replaced the deerskin tawse on the wall and
exchanged it for a senior rattan cane, slicing through the air with it a
few times so all could hear its evil swish. Mistress handed me the cane and
asked I deliver sixty strokes, taking a short break after every
dozen. Before I was allowed to begin however, Mistress took down a small
bowl from a nearby shelf containing a peeled finger of ginger, carefully
cut and shaped to resemble a butt plug soaking in some ice water. She
inserted the ginger into Jacqueline?s lovely, tight anus. After a minute or
two more had passed I was told to begin by the Mistress so I lowered the
cane upon the upturned flanks that met my gaze with all my might. A
considerable moan escaped my friend?s gagged lips as the cane hissed
through the air again, this time catching the unsuspecting bottom just
below the cheeks. The ginger was also working its magic as was quite
visible as Jacqueline would tense the muscles thus tightening about the fig
causing more of the oils of the ginger to contact the tender flesh inside
which burns unimaginably in such a spot forcing her to relax the
muscles. At that very moment I would strike so the feeling from the blow
would be intensified. I stopped as instructed after the first twelve blows
had been delivered and gazed as deep dark red welts formed in dark contrast
to the remaining areas of milk white flesh. Taking the cane in hand again,
I began to further torment the buttocks before me wide eyed and with a
sinister sneer as the cane bit those ass cheeks again and again.

Jacqueline nearly passed out twice before reaching the end of those sixty
strokes and appeared quite relived when Mistress removed the ginger fig
from her anus although by this time the ginger had ceased to
burn. Apparently its effects wear off after about twenty minutes or so but
almost forty minutes had elapsed since the caning began. Mistress however
did not put the cane away, merely setting it aside for now by close at hand
so I guessed she may not be thru with it just yet. The Mistress and I had
left dear Jacqueline for a moment so we could strip down and began to
lovingly fondle my member as we did so. I was standing nice and proud at
almost ten inches in length and of considerable girth when fully erect when
Mistress dropped to her knees before me and took my rigid organ deep into
her throat. Her cocksucking felt really great and she took the entire shaft
down without gagging even once, something I?ve always consider quite an
accomplishment. After tending to my engorged cock for a bit she produced a
small piece of black leather I?d guess to be about six to eight inches
square, its surface covered with metal studs, not sharp mind you but round
dome shaped ones and rolled into a tube with some leather lacing between
the two ends. Mistress Pembroke slipped the piece of studded leather over
my erect penis and pulled the laces tight along the underside tightly but
not overly so as to be painful however it did tend to make the size of my
cock head increase to the size of an apple. Mistress also tied a leather
cord about the base of my organ making it impossible to lose my heightened
state of arousal. We returned where Jacqueline awaits, still strung up
between the columns approaching from the rear. Jacqueline turned her head
so she could see us return with Mistress Pembroke walking ahead of me
obscuring my heavily adorned dick from view until I was able to take my
place standing directly behind the savagely abused bottom. Mistress then
placed a blindfold over Jacqueline?s tear streaked eyes, her face a mess
from all the mascara that ran down her cheeks then unchained just her
arms. A padded sawhorse was brought over from the corner of the room and
placed just in front of the tortured Jacqueline and she was bent at the
waist over it and her arms reattached to the front arms close to the floor
forcing the bruised ass to stick out in a most provocative manner. Mistress
took up her cane silently and motioned for me to step back just a
little. Suddenly without any warning she swung the cane vertically and
carefully aimed so the tip would strike between the wounded globes and land
solidly upon the already inflamed anus. Again and again she struck the
swollen portal with all her might. She only struck the tormented rosebud
about a dozen times but the assault was extremely vicious and blood was
oozing from several of the worst wounds. I again took my place, my cock
twitching at the proffered opening, its head a deep shade of purple and
swollen to twice its normal size and the shaft behind in its black leather
sheath looking like its covered with chrome plated warts and quite anxious
to plumb the depths of the splayed rectum before it. Mistress Pembroke took
her place before Jacqueline and removed the ball gag and offered her cock
for the hapless Jacqueline to fellate. From my vantage point I could see
Mistresses cock swell in response to Jacqueline?s caress as I was given my
signal to force my bound pecker up that tight tunnel until I was balls deep
while at the same time Mistress pushed her own deep down her throat. The
two of us pounding our cocks into the respective waiting holes as if we had
never fucked before, not paying any heed to the pleasure of the submissive
but only our own animalistic need to breed this bound masochistic slut. We
were able to keep up our assault for a good half hour before Mistress
Pembroke could contain herself no longer flooding Jacqueline?s mouth with a
copious amount of her thick white cream, a big gob leaking from the corner
of her stuffed lips. As I watched this happen I felt that familiar tug in
my own sac and despite the leather bindings shot a load deep within the
belabored bowels. Spurt after spurt erupted from my big, thick cock more
powerful than any salvo I?d shot in recent memory. With that Mistress and I
got up and left the room as she turned out the light leaving Jacqueline
still bound to the sawhorse where she would remain for the rest of the
evening awaiting her busy day tomorrow... Toilet Traning!