The Bully Pt. 17

"My office, now," Samantha barked, as the line went dead.

When I reached the open door of her opulent corner office, Samantha was on the phone with her feet up on the desk. Out of respect for the fact that she was my boss, I knocked prior to entry. Samantha looked up from her conversation, and with a motion of her raised index finger, beckoned me in. I tried to enter the office like a composed, confident attorney. However, as Samantha seemed to mock me with her eyes, I suddenly felt insecure, and lowered my gaze as I shuffled nervously towards her desk. Samantha kept me waiting for a full fifteen minutes, as she logged another billable hour.

Samantha still had her feet on her desk, the red soles of her Louboutins reminding me of the gulf in our financial status. I tried not to focus on her physicality. However, as her toned legs rested upon the leather-topped desk, and her skirt rode up her thighs as she reclined in her huge chair, I caught a glimpse of her garter-belt strap. I was already under a lot of sexual provocation between the visual of the photos and the titillation that I felt when booking a hotel for Lela's latest fuck-buddy. So, it was no surprise when my cock twitched in response to my glimpse of Samantha's garter-belt strap. I tried to fight it, but I had a lot of sexual history with this woman. In addition, I deeply regretted leaving her for the CumSlut, so I knew that I was fighting a losing battle.

Finally, after what seemed like an eternity, her conversation reached its natural conclusion, and Samantha hung up the phone. As I stood at the edge of her desk, trying in vain to suppress my arousal, she took her sweet time to acknowledge me, glossing her lips in a beautiful shade of pink, before spritzing herself with her trademark perfume.

And just like that, despite my efforts to fight it, I was fully erect.

"I am very disappointed in you, Mark," Samantha began, setting the tone for a thorough dressing-down. "I had hoped that we could have an adult conversation about your misdeeds, but it appears that you have once again succumbed to your base desires. I refuse to engage you when you are in such an elevated state of arousal. The sexual tension is disrespectful and counterproductive to our end-goal. Take care of it before we continue."

"Take care of it?" I stammered as I struggled to process exactly what she was saying.

"Don't be coy, Mark," Samantha instructed me. "You come into my office under suspicion of theft of my intimates, and inexplicably you decide to enter with a boner? Your judgment is clearly impaired and I need to talk to you when you have a clear mind. So, clear it. Jerk off."

As I stood before my ex-lover and current boss, Samantha's request seemed surreal to me, and it was this that caused my hesitation. Samantha was not in the mood for any bullshit delay-tactics, and with a bored look on her face, reached into her desk drawer and emerged with a small plastic container of Vaseline. I found her look of contempt arousing even as she tossed the Vaseline in my general direction.

"Drop your pants, Mark. Jerk off for me," Samantha said with an air of finality. "I won't ask you again."

Driven by my desires, and in an effort to placate Samantha, I picked up the small tub of Vaseline and started to unzip my flies. It wasn't until I lowered my tailored suit pants that I remembered that I was wearing a light-blue pair of my ex-girlfriend's underwear. By this time it was too late, and as Samantha processed my embarrassment, I coated my erect cock with a copious amount of the petroleum-based jelly.

I knew I wouldn't last long under the circumstances, but as I felt my nuts constrict, Samantha upped the ante. Slipping her perfectly-manicured hands under the hem of her skirt, she slowly lowered her panties to her knees. I believed that she was getting off on dominating me, and as the crotch of her silky g-string underwear came into view, my suspicions were confirmed. Slick with her vaginal secretions, there was no longer any questions about Samantha's arousal, but she seemed intent on accelerating my orgasm. Samantha slid her panties down her toned calves, before tossing them onto the leather topped desk.

"Sniff," she said with a giggle. "I know you like my scent."

I lifted the scented intimates to my nose and inhaled deeply. Predictably, I buckled under the additional stimulation of Samantha's aromatic panties, blowing my load across the top of her desk a few seconds later. I was still in love with this spectacular woman, and felt our chemistry every time that I was in her presence. Out of respect for Samantha, and due to the expectations in the workplace, I suppressed my feelings for her, but as soon as she ordered me to jerk off I knew it would be over quickly.

Samantha extended her dainty hand to retrieve her panties, and instructed me to clean up my mess. I had a cursory look around her work-space for some paper towels or tissues, in order to return her desk to an unsullied state. As I flashed her a confused look, Samantha crystallized her expectations.

"Lick it up, Mark," she whispered softly. "Good boy."

I hadn't experienced this side of Samantha, although after hearing about John's ordeal at her hands, I knew full well that it existed. My face reddened as I bent forward hesitantly to clean my ejaculate from her desk top.

"Kneel," Samantha ordered. "And eat."

As Samantha watched on intently, I lowered myself to my knees and began to tentatively lick up my load. I had hoped that her unnecessarily humiliating display of control would end as soon as I lapped up the first traces of my semen, but she kept me on my knees licking the leather topped desk for several minutes, until she was certain that I had ingested the entire load. Samantha never invited me to stand, so I remained kneeling the entire time that she addressed me.

After a thorough admonishment for my intrusion into her bedroom and closet, she moved on to the more egregious act, namely the theft of multiple items of her intimate wear. Labeling it an act of betrayal, a perverse and despicable lack of respect for her boundaries, and evidence of my overall contempt for women, Samantha even tried to frame the event as an assault.

"Do you have anything to say, Mark?" she asked in exasperation as I remained silent. "Any other misdeeds you would like to confess to, as I contemplate your punishment."

"I looked on your laptop, Samantha," I said quietly, hoping that my honesty might earn me some respite from her constant barrage.

"I know," Samantha responded firmly. "On your wedding night you were in my pages folders for seven minutes. Snooping around in my conquests file."

"How do....?" I began as she quickly cut me off.

"It's a collaborative file, Mark, you dumb fuck," Samantha started aggressively. "Working files are designed to allow multiple people to work on a joint task, but if you log-on, your contribution is noted. I was able to see that you viewed the file on my computer. How do you feel about the fact that I have pegged some of your co-workers, for much less egregious offenses than yours, by the way?"

I swallowed hard as Samantha made no bones about the fact that she viewed anal-penetration as an acceptable form of punishment and control within her work place.

"Well?" Samantha asked as she drummed her manicured nails on the top of her desk. "Any thoughts? I pegged Stan for persistent tardiness, and since that day he is always early to work. I bent Pete over my desk because he messed up his billable hours. He cried like a little girl when I butt-fucked him, but ever since that encounter Pete's accounting skills have improved immensely."

"Samantha, please," I begged.

"Quiet, Mark," she said firmly. "You will get your chance to speak. As you are undoubtedly aware, having viewed my desk immediately after it occurred, I recently pegged Danny Marshall. I followed my usual disciplinary process, allowing him the option to resign his position which I knew he would never do. That arrogant asshole makes forty thousand dollars per month, an amount which most people would agree allows the company to own his ass."

Samantha paused for dramatic effect, and I swallowed hard as I processed her words.

"My heart soared when Danny elected to take his punishment rather than quit," Samantha continued, apparently relishing the memories of that encounter. "He really deserved his though, for what he put Lela through. I had to gag that pussy to stop him from begging for mercy. He almost crapped himself when I ripped his underwear from him. Then after I had taken his ass he slinked off down the long hallway, without his underwear, commando style."

"Samantha, please," I began as stress enveloped my body. "I know I invaded your privacy. I am so sorry."

"Silence," Samantha barked at me, her dominant side quickly emerging. "I often wondered how you would react to being pegged. I have wanted to sodomize you since the day that we first hooked-up. You are the one that got away, Mark. The only man that I have kissed, whose ass I haven't taken. I am going to right that wrong today. I am also going to get my revenge for your sexual assault of me. I haven't forgotten how unnecessarily rough you were with me that day."

"Samantha, may I speak?" I asked respectfully.

"Say one more uninvited word and I will gag you," Samantha barked, thoroughly enjoying the control she had over me. "You should have let me fuck your ass when we were lovers, Mark. It would have been a very different experience, believe me."

As I fell silent, Samantha apparently decided to elevate my stress level.

"Stand up, Mark," she ordered me. "Bend over my desk. I wonder if you will beg like Danny or cry like Pete?"

Samantha's tone left no room for discussion, and I shuffled to the edge of the desk and bent forward until my upper body was laying flat across the large, leather-topped, mahogany furniture. I had lowered my head in submission by now, faced with the inevitability of getting pegged by my boss and former partner. Inexplicably, the only thought running through my head was whether Samantha's entry into her conquest file would record my violation as a "Work-related" or "Personal" punishment.

I heard Samantha unlock a file cabinet, and after rooting through one of the drawers, she laid several strap-on dildos on the desk in front of me. Initially they were in a pile but Samantha took the time to sort and arrange them by their girth. The smallest one was about the size of a woman's little finger and would have been very easily accommodated by even the tightest of virgin assholes. I found myself assessing each phallus and questioning whether or not I could have taken it in my anal-passage. The last three or four, which incidentally were jet-black in color, would have definitely torn me a new asshole. Samantha placed the jar of Vaseline next to the line of strap-ons, the inference being that it would provide the necessary lubrication for my punishment.

I heard the sound of a buckle being secured and then Samantha reached for one of the mid-sized dildos, snapping it into place with an ominous click. There was a tense silence in the room as she reached across my back and picked up the jar of Vaseline. A few moments later, after Samantha had apparently greased the tip of her strap-on, the Vaseline container rolled across the desk. I felt her manicured nails rake across my lower back, until they came to rest at the top of my silky panties. Then with a single motion, Samantha ripped the delicate light-blue intimates from me, before discarding them on the desk right under my nose.

I felt her lean over me, the tip of the phallus resting at the top of my butt-crack as she positioned her lips on my earlobe. After a long pause Samantha began to lecture me on the inequalities that pervaded the work environment of the legal profession.

"Our chosen vocation is a male-dominated field," she began, the vitriol evident in her tone. "Ever since College I had to work harder than the men in order to prove that I was worthy of admission into Law School. Two of my law professors offered me enhanced grades in exchange for sex. I turned them down, reported them to the school administration, and still graduated right at the top of my class. Even after I joined this prestigious law firm, it was immediately apparent that it was a fighting pit for Alpha Males. Danny Marshall ran the office back then, and it was a total boys club. They had hookers in the office regularly, and there was rampant use of recreational drugs. It was a dick-swinging contest and I wanted in, except I never had a dick. Well, guess what," Samantha added ominously. "I do have a dick now, and I intend to punish any man who disrespects me."

"Samantha, please," I begged, fearful of quite where this was heading. "I have always treated you with respect."

"Ha," Samantha exclaimed indignantly. "You objectify me the same way that all men try to. You just stole my soiled undies, for fuck's sake. How is that respectful?"

As I lay bent over the desk with the strap-on phallus resting on top of my bare buttocks, Samantha continued her line of questioning.

"Do you still have the rest of my intimates, Mark?" she whispered into my ear. "Think carefully before you answer. Do not lie to me."

"Yes, Samantha," I responded quietly. "I still have everything of yours."

"At the office?" she asked.

"Christ, no, Samantha," I said reflexively. "At my house."

"Is Lela aware that you snuck into my closet and stole my soiled panties from my laundry hamper, Mark?" Samantha continued. "I may need to talk to her about your actions."

"Please Samantha," I begged. "Don't involve Lela. I never told her about it. It will kill her if she learns that I still have feelings for you. You know how emotionally fragile she is. This revelation will break her."

"Well we don't want that to happen, do we?" Samantha intoned sarcastically. "Don't you think your wife has a right to know that you couldn't resist stealing my dirty panties, Mark? I would want to know if the roles were reversed and I was in her shoes. In fact, I would want to punish you for such an act of indiscretion. Do you agree that you need to be punished, Mark?"

My boss and former lover was wearing me down, and I said what Samantha needed to hear, in order to avoid Lela's involvement.

"Yes, Samantha, I agree that my actions warrant some punishment," I said meekly.

"Good boy," Samantha said condescendingly. "I am going to call Lela myself and let her know."

"Samantha, please," I cried. "Anything but that. Plus," I added, "Lela isn't going to be home tonight."

"Is she working tonight?" Samantha asked mischievously. "As the CumSlut? In some fancy hotel suite, on all fours being dragged around on the end of a dog leash?"

"Yes, Lela is entertaining a high-roller tonight in the Honeymoon Suite of the Hilton. She won't be back until the morning," I squeaked, my voice cracking under the stress.

"Maybe I should just punish you myself? Would you prefer that to Lela's involvement?" Samantha said, sensing that she had worn the resistance out of me.

"Yes, please, Samantha," I said nervously, unsure of whether I was making the right decision. "Just don't tell my wife. She is too emotionally unstable to process this news."

"Very well, Mark," Samantha said coldly. "As you wish. It appears that you and your slut-wife are both going to get butt-fucked tonight. Unless you would rather offer me your resignation?"

There was no way that I was going to quit this job, so I clammed up. My fearful silence seemed to embolden Samantha, and she adjusted her position and moved the tip of the phallus so that it rested right on the entrance to my anus.

"Samantha, please. Not that. Show me some mercy." I begged, as she rested one hand on the base of my spine to hold me in her desired position, and eased slowly forward.

I certainly was no stranger to receiving anal-sex as John had violated me in this manner on numerous occasions. However, John's primary purpose for sticking his cock in my rectum was for his pleasure and enjoyment, the end goal being for him to bust a nut. Samantha's invasion of my anal-cavity was done solely to punish me, ostensibly for pilfering her intimates, even though I felt that she harbored deeper resentment towards me. I had, after all, broken up with Samantha to get back with Lela, which must have hurt her pride a little.

Moments after she had eased the strap-on all the way inside my rectum, Samantha began to butt-fuck me in earnest. My first clue that her intent was to inflict pain on me, was her choice of lubricant. By eschewing the Anal-Ease, with its analgesic properties, in favor of Vaseline, I was denied the benefit of the numbing agent that the former lubricant provided. Samantha had also elected to forgo the ball-gag, and she seemed emboldened by my unrestricted cries of discomfort.

The pain got progressively worse as my former lover and current boss reamed my ass with her strap-on phallus. I cried like a little girl, begging her for some respite.

"Samantha, please," I pleaded. "You are really hurting me. Stop, I am begging you."

"I am so glad that I didn't gag you," Samantha responded, as she continued to pound away at my asshole. "I am really enjoying hearing your anguished cries. All the staff has left the office and the cleaning crew don't come until 10pm. We can make as much noise as we want."

Fortunately for me, the sustained thrusting motion that my punishment required was extremely physically taxing, and after a few minutes Samantha began to exhibit signs of fatigue. Her cadence slowed and the depth of her penetrative thrusts lessened with each passing moment. As it became less physically overwhelming for me, Samantha grabbed a fistful of my hair, cruelly yanked my head back, and began to verbally berate me as she sodomized me with a little less brutality.

"You will regret leaving me, Mark," Samantha hissed in my ear. "The dirty CumSlut who you chose over me will cause you nothing but pain and suffering. We would have made the perfect couple."

In an attempt to allow Samantha to vent and achieve her cathartic moment, I remained silent and passive, my only sounds being grunts of pain with each continued thrust of her rapidly-tiring hips. Samantha spat a few more pejoratives in my ear, before finally withdrawing her soiled phallus from my gaping asshole.

"Kneel before me," Samantha said, as she rested against the edge of her desk.

At this point my pants were still around my ankles which inhibited my movement somewhat, and I struggled to adopt the kneeling position. Once I was on my knees, Samantha placed one of her hands behind my head and pulled my face towards the strap-on dildo.

"Clean your mess from my cock, Mark," Samantha said spitefully, as the phallus slid between my lips.

When I arose from my peaceful slumber this morning to face my day, I had no clue that I was going to get butt-fucked by my boss. So, I had no reason to take the preparatory steps of an enema-cleanse that would usually precede a pre-planned bout of anal-sex, particularly if the person on the giving end enjoyed the additional humiliating ritual of ass to mouth.

I kept my rectum fastidiously clean during the years that John regularly sodomized me. However, without any warning from Samantha, I found myself in the distinctly unappetizing position of sucking my mess from her large strap-on, as she verbally demeaned me. Samantha kept me on my knees with that soiled phallus in my mouth for way longer than was necessary, just to prove a point.

"Pete. Stan. Danny. John. And now you," Samantha said triumphantly. "I love to watch disrespectful men kneel before me and clean my soiled strap-on with their mouths. You may stand, Mark."

Once I got to my feet Samantha tossed me a packet of wet-wipes. I withdrew two of the moist wipes, and swiped them between my buttocks. I had to suppress my concern as the anti-bacterial cloth emerged with a few blood droplets on it.