Who's The Boss? Ch. 10byJs_Keeper©
Author's Note: Although you can enjoy the story as a stand-alone, I recommend reading the earlier chapters in order to get the context of this story.
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When I awoke with the early light of dawn on Friday morning, it took me a few startled seconds to realize where I was. Despite having fucked my boss every way possible since taking her as my submissive pet several weeks prior, I’d had yet to actually sleep with Adrienne. For me, spending the night with a woman always represented a significant step forward in the relationship, and one that I never took lightly. But as I gazed down at her, sleeping soundly with her head resting on my stomach facing away from me, I felt no doubts about my decision to stay the night.
Sentimental significance aside, there was also the risk that her husband could have returned home unexpectedly, but neither of us seemed to give that possibility much thought as we tumbled into her bed the night before, exhausted and exhilarated after hours of incredible sex, culminating in my taking her anal cherry. As I watched her bare back rise and fall with her deep breathing, I lightly touched the soft dark blonde curls where they brushed my abdomen. As much as I wanted to let my little slut sleep, my cock began to stir when I recalled the amazing middle-of-the-night blowjob she’d woken me with. It looked to me like she’d barely moved since sucking me dry.
Without so much as a stretch or a yawn or a murmur, I suddenly felt Adrienne’s hand on my semi-hard manhood, stroking me toward full mast. Relentless slut! She slipped her head beneath the sheet and drew me into her warm, wet mouth, tongue swirling madly about my shaft as I moaned my encouragement. Soon my cockhead was poking against the back of her throat.
“Good morning little slut,” I sighed.
She didn’t respond with more than a muffled moan, but kept up her oral assault by sliding her mouth fully on and fully off my pole, stroking my balls and shaft all the while. I peeled the sheet down a little further so I could access her better and ran my hands over her perfect little ass. Eventually I worked a finger down the crack and into her well-used yet still lubricated rear hole. She gladly opened herself up to the invasion, relaxing her anal muscles and allowing me to add a second finger, while never missing a beat with her mouth.
“I think my little slut wants my cock in her ass again already. I thought you might be worn out back there after last night.”
Without a word she slipped my hard shaft from between her lips, pushed down the covers, and swung her leg over to straddle me. Reaching behind her she positioned the tip of my cock at the entrance to her ass.
“Please, Sir. Will you fuck my ass again?” she pleaded lustily, leaning down to give me a hot, open-mouthed kiss.
“Lube?” I asked.
“How about this kind?” she said, redirecting my cock to the entrance of her pussy and plunging her body down onto me all the way. She was certainly wet enough to do the trick, I thought.
“I think you are plenty lubed up now, Sir” she cooed as she rode up and down the entire length of my shaft repeatedly, the copious cunt juices evident by the loud sloshing sounds emanating from our nether regions. She rose up all the way, releasing my soggy shaft from her pussy, and shifting her body slightly forward, lowered herself slowly, gradually impaling her ass with my cock.
We both grunted with delight as my girth stretched her ass open. Inch by glorious inch she offered me her forbidden hole until coming to rest with me balls-deep inside her. Her eyes drifted shut as she relished the feeling of fullness, using her muscles down there to squeeze my cock tightly. My hands moved to her chest, firmly cupping her wonderful breasts and massaging her stiff nipples with my thumbs.
“I want to watch you come for me, little slut,” I instructed her.
She stuck the index finger of her right hand into her mouth and sucked it seductively for a few seconds before drawing it out slowly between her moist lips.
“May I?” she asked as she slipped that finger down between us and between her pussy lips. “I think I’m a little too sore this morning for another anal orgasm.”
“Of course, pleasure yourself in any way you wish. I just want to see your face as you come.”
With one hand on my chest for support and the other hand working over her clitoris and pussy, Adrienne began to rock up and down on my shaft. As her ministrations front and back continued, the look of discomfort shifted gradually to a look of utter pleasure. While she worked over my cock with her sweet ass I kept up my assault on her nipples.
“May I come now for you, Sir?” she asked much sooner than I had expected.
“Hold off for a minute. When you feel me filling your ass, you can come too.”
“Yes, Sir, as you wish.”
She soon was panting heavily both with sexual excitement and the physical exertion required to raise her body weight up and down on me. Truthfully I could have come any time, but I wanted her to work for my pleasure and for her own, to push herself physically to the limit of her ability, before finding relief.
“That’s a good little slut,” I exclaimed, finding my own difficulty in holding back. “Milk my cock with your ass.”
Despite her obvious exhaustion, her tempo quickened on me, raping her own ass with my hardness. Sweat formed on her brow and her breathing grew shallow and rapid. Her face reddened with exertion and restraint as the desperation for release grew almost uncontainable.
“Please,” she managed to groan. “I can’t’…” Her voice trailed off.
“Look into my eyes little slut and take my come,” I exclaimed loudly.
Her pleading eyes opened just as my cock began to pulse in her ass, and as her own climax erupted they widened with delight, betraying her surprise at the intensity of her own pleasure. As we came together, Adrienne never slackened her fucking motion in the least until at last I rolled her off of me and onto the bed next to me, my manhood slipping from her anal passage.
I pulled my body up over her; holding myself up on my hands as I peered down at her beneath me, limp with so much bliss, and strikingly beautiful.
“You are getting me addicted to you, Adrienne.” I surprised myself that I had used her real name for the first time since I could remember.
“Is that a good thing or a bad thing?” she asked coyly.
I leaned down and planted a soft, gentle kiss on her lips before I answered.
“Don’t you see? I’m falling in love with you.”
She smiled gleefully up at me and threw her arms around my neck, pulling me to her forcefully and giving me a passionate kiss that told me just how happy she was to hear those words at last.
Our sweaty, sated bodies lay intertwined, kissing and nuzzling for another thirty minutes before I reluctantly decided I needed to head home and quickly get ready for work. Once dressed, I leaned down and kissed Adrienne’s cute little ass where it was sticking out from beneath the sheet. I then gave her cheek a little smack, right where I had been kissing. She barely moved.
“Better get up soon, little slut. It wouldn’t do for us to both stroll in late wearing the silly, satisfied grins that we’ll more than likely be wearing today.”
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I sprinted through my morning routine and ended up being only ten minutes late for work. My morning was crammed full of meetings and phone calls, and I barely had a minute to breath until mid-afternoon. It was then that I first realized that Nikki had not sent me the required cell phone photo of her lingerie choice for the day. I sent her a text message to meet me in the media lab at 4:30, feeling certain that it wouldn’t be in use so late on a Friday afternoon.
I was waiting for her when she walked in.
“Lock the door cunt,” I said sternly.
“Do you think it’s safe for us to meet here like this?” she asked nervously.
“Lock the door cunt,” I repeated in a more harsh tone.
“What if someone should want to use the lab for…” I slammed my hand down loudly on the top of the table I’d been leaning against.
“Now, cunt!” I said angrily. She quickly locked the door and turned back toward me, looking a little fearful.
“You are pushing me aren’t you cunt?” She looked at me sheepishly, feigning confusion and shrugged slightly.
“Take off your shirt and your skirt,” I said firmly. “Show me now what you were supposed to have shown me this morning.”
Her fingers went to work, frantically undoing her buttons, revealing the black corset underneath her sweater. She quickly unzipped and slid her skirt down and off her legs, exposing the matching thong.
“Turn slowly for me.” I ordered. She revolved slowly in her low heels, allowing me to inspect her gorgeous body. Her long brown hair cascaded gently over her bare shoulders, stopping just above where the corset began. Her full, firm breasts were nicely presented by the cleavage-enhancing cut of the corset, which also nipped her waist alluringly. Below, the satiny black thong set off her creamy white buttocks in stark contrast.
“It’s a good thing you are so sexy,” I said after taking a nice long gander at my second sex slave.
“Why is that, Sir?” she asked demurely.
“Because I have a mind to take back all the sexy things I bought for you as a response to your blatant disregard for my instructions. You did disobey me on purpose this morning, didn’t you?”
“I wondered how long it would take you to break.”
“Break, Sir? I don’t understand.”
“I knew that if I withheld your punishment long enough, if I completely ignored you sexually, eventually you would deliberately do something to anger me, in hopes of inducing your punishment. You actually lasted longer than I thought you would, especially given the way I interjected you into Adrienne’s own punishment.”
“And now that you’ve broken me?”
“Truthfully, it will make no difference in the timeline or severity of your punishment, cunt. To do otherwise would positively reinforce the weakness you have shown. It would reward your disobedience and disrespect. That wouldn’t do, now would it?”
“No, Sir.” Nikki looked visibly disappointed.
“Tonight, in addition to your other writing assignments, you will write me a formal letter of apology for your actions.”
“Yes, Sir. I will.”
“Now get dressed and return to your desk. I expect that we won’t have to deal with this kind of defiance again. If you cannot wait patiently for your punishment to be meted out at the time of my choosing, it will only serve to delay it. Now go.”
I don’t know if she realized how sexually charged I was at the moment or if she saw the bulge in my pants that her sexy body and lingerie had created. It took every ounce of self-control I had to not throw her up on the table and fuck her bald cunt like a madman.
I watched lasciviously as Nikki dressed herself quickly. She unlocked the door and then turned to me before opening it.
“I’m sorry, Sir,” she said sincerely. “I didn’t mean to anger you so.”
“I know, cunt. Just go. And when you get back to your desk, send your boss down here immediately. I need to fuck something badly.”
I could see the jealous irritation on her face. Sometimes I could be such a brutal bastard.
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I slept in a little later than usual on Saturday morning, so it was nearly 10 am by the time I sat down at the computer in my guest room, which doubled as a home office. As I sipped a strong cup of black Jamaican coffee, I was pleased to see five new emails from my two subs, despite the fact that I had checked email right before turning in at midnight the previous night. One was from Adrienne, and four were from Nikki. I decided to open them in the order they were sent.
Adrienne’s was first, and it contained her picture assignment for the night before. It actually contained two pictures, each with a corresponding reason behind the selection. She explained in the email that her husband had returned home early from his trip that afternoon, noting how close a call we’d had with me spending the night before. She also said that he seemed to be hovering around more than usual, which she laughingly speculated was due to the amazing and uncharacteristic blowjob she’d given him the week prior. Therefore, she had slipped silently out of bed at 2 am to send the picture assignment from Friday night and the one for Saturday morning, fearing that she might not have a chance to do so otherwise.
The first picture showed two topless women, one blonde, one brunette, kneeling in front of a man in a business suit with his fly undone. The two women faced each other and had their bright red lips pressed tightly to either side of the man’s bulging member, their lips barely touching together around him. The next picture, obviously a later shot from the same scene, depicted the same two women, now completely naked, still kneeling in front of the man, who remained fully clothed. Facing one another, their mouths were locked in a passionate kiss as he emptied his balls over their sweet faces. Adrienne wrote that what attracted her to these two pictures was the way it displayed the women’s adoration of the man’s cock, while also clearly portraying their enjoyment of each other. Very hot. Such a good little slut.
I moved on to the first email from Nikki, which I noted with surprise was sent at 5:50 am. Here’s what it said.
>>> Sir, here it is Saturday morning and my chance to sleep in, but I’ve been awake and restless since 5:15. I finally decided to get out of bed and write. As I told you in my letter of apology last night, I’ve been unable to think of anything but my pending punishment ever since you and Adrienne wrenched that fantastic orgasm from me, causing me to lose the challenge and acquire the consequence, which so far remains a complete mystery to me.
>>> I suppose that you are intentionally delaying the pronouncement of sentence. I suppose that you have purposefully made me aware of and even used me in Adrienne’s punishment. I have learned that everything you do is for a purpose, Sir. Still, my mind and body have been continually on edge, preoccupied with fantasies of what I might be forced to do as retribution for failing to withhold my own orgasm against the merciless onslaught of pleasure you and Adrienne subject my body to. Of course you knew this kind of preoccupation would be my natural reaction. Of course you knew that the panties you bought for me would be constantly wet, just as they are now. Of course that is why you wait. You are bringing out my inner whore, aren’t you?
She signed the email “cunt cum whore.” I was immediately struck by her keen intelligence and sharp wit in cleverly using the dual meaning of “cum.” Most obviously, it is commonly found in erotica as the word used for orgasm, or for male ejaculate, especially when cum and whore are used together to mean a woman who lives her life in pursuit of said ejaculate. More subtly however, cum is the Latin preposition indicating that something has a dual role, or more to the point, something that is being changed from one thing into another. Hence, cunt (her former slave name) cum (being change into) whore (what her Master desires her to become). Simply brilliant.
Before replying I decided to finish reading all her emails. Next was her morning 3-way picture assignment, which depicted a woman bound tightly to a chair and gagged with her panties. Behind the bound woman, out of her line of sight and just slightly out of the camera’s focus, you could see a man and woman, whose naked bodies were entwined together in passionate lovemaking. She explained the dual purpose of her selection. First, of course, the bound woman reminded her of the orgasm race she’d endured in Adrienne’s office a few days prior. Second, she said that the idea of only being able to listen as Adrienne and I made love in the same room was titillating to her. She didn’t really know why, but she went on to describe in detail what the woman in the chair heard, smelled, and thought as the couple behind her fucked with abandon. She explained how breathlessly she’d waited for Adrienne to return from the media lab the night before, freshly fucked and dripping with my come. She said that her hurt feelings melted into fervent desire as she sat at her desk imagining me brutally fucking our boss.
The next email from Nikki was a story continuation. In a previous email, Adrienne had set up the scene, now four days into the seven-day cruise we were enjoying together in the story. The three of us were in the aft “adults only section” of the ship, enjoying a bottle of wine in the hot tub. As Adrienne described it, the girls were in their skimpiest white bikinis, which had become almost transparent when wet, and I sat between them with a raging hard on. Nikki took over from there, describing how the girls took turns riding my cock right out in plain view of a dozen or more other people. Doing their best to keep their movements subtle, they simply moved their bikini bottoms to one side and impaled themselves on my stiff cock, squeezing me with their pussy walls instead of riding up and down on me. The thought of publicly fucking these two gorgeous women was fascinating and exciting to me, but I decided to write my addition to the story later.
On to Nikki’s last email, written less than thirty minutes prior. It simply read, “I know I’m not supposed to beg, but punish me, PLEASE, Sir.” She signed it the same way as she had each of the others: “cunt cum whore.”
I smiled to myself and sat back in my desk chair while I continue to sip my coffee.
I thought a brief minute, and then pushed myself back up to my computer. I typed an email to both women. “Nikki’s punishment starts tomorrow. Both of you be sure to check you email before 10 am for further instructions.”
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I awoke Sunday morning with an eager sense of anticipation. I went immediately to my bedroom window to discover that the weatherman had, for once, gotten it right. It was a cloudy, drizzly, grey morning – perfect for the start of Nikki’s punishment.
After making my usual strong pot of coffee and stuffing down a bagel with extra cream cheese, I went to my computer to compose my instructions to my two sexy subs.
>> Good Morning Cunt and My Little Slut,
>> I hope you are ready for our little adventure. I’ll remind you that you are to follow these instructions precisely. You may find them challenging, but you will find disobedience brings severe consequences. I rather suggest that you not test me in this.
>> Each of you will find a large zip-lock bag beneath the front seat of your cars containing the supplies necessary for today’s adventure. At exactly 10 am, without looking at the bag or its contents, you will drive to Seven Lakes Park. Use the small parking lot off of 8th Avenue (Google Map link is shown below, it if you need it.) I’ll be there waiting for you. Park on either side of my car. Once parked, you may remove the bag from beneath your seat. You will find further instruction there.
>> Please note that I am simply there to observe your obedience; so do not acknowledge my presence in any manner unless directed to do so. Follow the instructions exactly.
My heart beat hard in anticipation of the girls’ reactions to my message; even more so in anticipation of the evil adventure I had planned.