I had been dominating Samantha for about two weeks when the time came to punish John. As instructed, John had requested three weeks vacation from work, although he was blissfully unaware that it was to be used to recover physically from his upcoming ordeal. I gave Samantha specific instructions about how I wanted John's punishment to unfurl. I wanted us both to fuck his ass, then I planned to administer a thorough beat-down with the rattan cane. Once we had broken him, I wanted to make him watch Samantha and I have sex.
Samantha planned to confront John about his inadvertent fuck-up, the commingling of funds, and offer him the option to resign or be punished.
I knew that he wouldn't resign. John had been awarded a very competitive salary and benefits package, and quite frankly didn't have the requisite knowledge or experience to be considered for a comparable position at another law firm. I had carried John through Law School, and there were gaping holes in his understanding of the legal field. When Samantha accosted him regarding his accidental commingling of funds, John was at first apologetic. However, as he was apprised of the potential consequences, John's remorse turned to abject terror, particularly when Samantha informed him that he faced disbarment and possible incarceration. John didn't possess the intelligence or curiosity to establish whether the blame fell entirely on his shoulders, so he folded like a pack of cards, verbalizing his intent to take his punishment like a man.
John had been pegged by Samantha before, although the first time was an exercise in control, rather than a punitive measure. At the appointed time, John entered Samantha's office, his head hung low out of respect. I was waiting in the bathroom that adjoined her spacious office, and emerged only after John had disrobed, and was securely tied across Samantha's huge mahogany desk.
I had waited close to a decade for retribution, and the look on John's face was priceless as he absorbed the fact that I was complicit in his punishment. John was a powerfully-built man, large in stature and extremely athletic, thanks to years of martial-arts training. However, even as he struggled in futility against his bonds, he seemed incapable of understanding that I had secured the upper hand.
John had a look of horror on his face as I approached Samantha and we shared a tender kiss. Resting my hand possessively on her ass, I posed the question.
"Do you want first crack at him, Samantha?" I asked, barely able to suppress my thirst for revenge. "Or shall I sodomize him while you fuck his mouth with your strap-on phallus?"
John struggled in vain against his bonds that day. Part of me felt sorry for him, but once I stuck my Vaseline-coated finger through his sphincter, thereby greasing his asshole, any concern I had for his well-being evaporated.
John's ass was tight, which was to be expected since he had only been penetrated anally on one previous occasion. Samantha had pegged John when they were lovers, but that had been a tender moment in comparison to what was unfurling today.
"This is going to be all about me, John," I said coldly. "I am finally going to make you my bitch. A true pump and dump ass-fucking."
Paying no attention to John's needs, I simply eased inside his tight ass, until I was buried balls-deep. I grabbed a handful of his hair, and pulled his head back so that Samantha could fuck his face with her phallus. Once we had John in the classic 'spit-roast' position, I pounded his anal-cavity relentlessly, as my nemesis' muffled cries for mercy reverberated around Samantha's office. I don't harbor any homosexual tendencies so it took me several minutes to reach my climax. In fact, it wasn't until Samantha removed her strap-on from John's mouth, and came round to where I was standing, that I knew that I was going to blow my load.
John cried like a little girl as I forcibly sodomized him. Samantha stood right next to me, nibbling my earlobe and whispering words of encouragement, as I butt-fucked my nemesis.
"Go on, Mark," Samantha cheered, "Make John your bitch. You own his ass now. Any time you feel like busting a nut between his sweet cheeks, just let me know. I always knew that you would get the last laugh, Mark."
It was years in the making, and finally as I listened to the heavenly combination of John's cries and Samantha's encouragement, I pounded John's asshole with a fury, until I ejaculated between his muscular buttocks.
It was never about sex. I wasn't physically attracted to John but nonetheless it was sweet revenge to forcibly butt-fuck that prick. After I climaxed I withdrew my cock from his gaping anus.
"Stick it between his lips," Samantha encouraged me. "Make John suffer the indignity of ass to mouth."
Following Samantha's instructions, I went around the edge of the desk and presented my cock to John, as he lay naked and tightly bound. When John woke up this morning he had no idea that he was going to get anally-raped, so I assume that he had not used an enema when he showered.
My suspicions were confirmed when I placed the tip of my cock against John's lips. My nemesis recoiled at the unappetizing odor, and then retched. John let out an anguished howl as Samantha grabbed his testicles and gave them a tight squeeze.
"Open up, John," Samantha ordered. "Time to clean Mark's cock."
John reluctantly parted his lips and resigned himself to the disgusting task at hand. While John licked my cock clean, Samantha placed her hands on his buttocks and pulled them apart. Then, using my ejaculate as lubrication, Samantha forced her strap-on phallus deep inside John's anal-cavity.
Samantha pegged John with a brutal ferocity that I never even knew she possessed. She harbored a deep-rooted resentment for John in the wake of his monumental screw-up. John's inadvertent commingling of funds had irreparably altered the trajectory of Samantha's life, and she wanted to hurt him for that. After my cock was clean, I moved to one side of the desk and watched on dispassionately as Samantha brutally sodomized my nemesis. John's anguished cries were real now as the latex phallus pounded into his anus.
Samantha butt-fucked John for nearly twenty minutes, her rage finally dissipating as she rained a barrage of insults down on him. Finally, with perspiration visible on her forehead, she removed the strap-on cock and stepped back to admire her handiwork.
John's ass was gaping wide open, and there were droplets of blood visible at the entrance. Traces of my ejaculate leaked from his anal-cavity, further proof that he had been used as a cum-receptacle by another man. Samantha grabbed her iPhone and took a few pictures of her hapless employee in his compromising position.
"Grab that ottoman, Mark," Samantha instructed me. "I want to make John kneel on it."
Her intentions became clear as soon as I dragged the heavy leather foot-stool over to Samantha's desk. It was just the perfect height to support John's lower body without untying him. I simply bent one of his legs at the knee, and slid the ottoman beneath him, before repeating the process with his other leg. Now John was still bound tightly to the desk, but instead of standing to support his weight, he was kneeling on the ottoman.
John was still recovering from his forcible ass-fucking, and whimpered as we moved him into our desired position. As he knelt on the ottoman, my semen leaked from his asshole, which was a satisfying sight. The soles of his feet were now upturned and fully exposed for phase two of his punishment.
Retrieving a rattan cane from Samantha's desk drawer, I laid it on the desk right by John's face, thereby telegraphing my intentions.
"Do you know what Bastinado is, John?" I asked my nemesis, as he renewed his struggle against his bonds. "Or how excruciatingly painful it can be, if applied with sufficient enthusiasm? Which I certainly possess," I added coldly.
I picked up the rattan cane, rounded the desk, and ran the instrument of torture gently across the soles of his upturned feet.
"Mark, Samantha, please," John begged. "I had no clue that I deposited the funds in the wrong account."
"You have been punished for that indiscretion already, John," I informed him calmly. "The Bastinado is revenge for my seven years of sexual enslavement at your hands. I have waited a long time for this."
Feeling as if no further explanation was required, I lifted the cane skyward, and brought it down forcefully upon John's upturned feet. John let out such a cry of anguish, that Samantha reached into her desk and grabbed her ball-gag. I recognized it immediately as being one of the things I noticed after Samantha pegged Danny Marshall.
"Wait just a moment before you gag him, Samantha," I requested. "John and I are going to have a little heart to heart before I whip him into oblivion."
"Mark, please," John begged me. "Show me some mercy."
"Hurts like a motherfucker doesn't it, John?" I exclaimed cheerfully. "I was only able to endure four strokes before I threw in the towel. You are in for a long afternoon. By the way, I know that you fucked Crystal too, John," I added, enjoying the look of fear on his face as he contemplated my additional motivation to hurt him.
"Mark, you guys weren't even an item back then," John pleaded. "There was no way for me to know that she would end up being your girlfriend."
"You knew that Crystal was my girlfriend when you stuck your hand up her skirt and relieved her of her panties, John," I said angrily. "At Stacey's Bukkake party that you willingly participated in, even though you knew that Stacey was my girlfriend too."
John was lost for words, and turned his appeal for clemency to Samantha.
"I am the only one of Mark's girlfriends that you haven't fucked, John," Samantha said coldly. "Why on earth would I show you any mercy?"
"My office is almost soundproof, Mark," Samantha explained, turning her attention to me as she forced the large black latex ball into John's mouth. "However, this bitch is going to squeal like a pig and I don't need any unexpected interruptions."
The ball-gag did an admirable job of suppressing John's pitiful howling, and as he lay bound before me I whipped his feet into oblivion. John took a dozen strokes of the cane on the upturned soles of his feet, before Samantha intervened and suggested we move to a different part of his anatomy to prevent permanent damage. It was a cathartic moment for me, a fitting revenge for all John had put me through.
I ended up administering thirty-six strokes of the rattan cane that afternoon. John took twelve to his feet, twelve to his muscular buttocks, and a further twelve to his shoulder blades, which turned out to be surprisingly painful. Once I was done I was sweating profusely, breathing heavily and pumped full of adrenaline. I dropped the cane on the desk right in front of John's nose, and flopped into Samantha's leather chair.
