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!