Who's The Boss? Ch. 09

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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Enjoy!

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My initial plan had been to punish my two inter-office submissive playthings in the same manner and at the same time. But after further consideration, it dawned on me that my boss, Adrienne, and her secretary, Nikki, would require distinctly different approaches to the punishment they both had coming as a result of the "orgasm race" I'd staged in Adrienne's office. As I intended, Nikki had lost the contest by coming first and thus was due to receive the punishment. But Adrienne, my greedy little slut boss, in exchange for a single post-victory orgasm, had agreed to receive punishment also. Foolish woman, she had no idea what it was she had traded for that fleeting bit of pleasure.

I decided to make Nikki wait a while before revealing the consequences of her defeat. I knew this would add greatly to her anticipation and intensify her focus on the coming punishment, although at the time I didn't realize the extent of the impact this would eventually have on her.

So, Thursday morning, the day after the race, I informed Nikki by email of the delay in her punishment. For now she was to simply continue to adhere to my standing order restricting her orgasms and continue with her daily writing assignments: the chain story of debauchery between the three of us aboard a cruise ship, and a twice-daily selection of a picture depicting a FMF three-way scene, including a description of exactly what drove the particular choice. These simple orders would serve to continue the priming of Nikki's sexual pump.

After sending the email to Nikki, I turned my attention to Adrienne's punishment, which I felt needed to start immediately. As I sat at my desk pondering my options, I suddenly remembered the gift I'd purchased for her at the adult toyshop on Tuesday of that week. The startling events of the day, Nikki's entrée into my domination, had caused me to forget all about it. I pulled open my bottom desk drawer, withdrew a plain paper bag hidden toward the back, and peered inside. As I stared down at the black anal plug set I'd purchased, I knew exactly how to proceed with my little slut's consequences.

I was going to fuck my boss's ass.

The immediacy with which I would carry out Adrienne's sentence would serve several purposes. First of all, as Nikki observed her boss's punishment, it would fuel her imagination as to what I might have in store for her. Second, it would allow me to further test the waters of jealousy between my two women, to see how they withstood the temptation to draw conclusions and make judgments when treated differently. Finally, the sooner we started anal training, the sooner I would get to take possession of Adrienne's virgin ass.

I quickly phoned Nikki to request a meeting at my boss's first available time. When she asked the subject, I ambiguously informed her that was a meeting about training. Five minutes later I got a text from Adrienne on my cell phone, "Training?" I simply shot back, "Yes."

I purposefully arrived at Adrienne's office a few minutes before our scheduled meeting time and took a seat across from Nikki's desk in the executive office waiting area. From the comfortable over-stuffed leather chair I had a pleasant view of Adrienne's gorgeous young assistant as she sat at her desk working diligently on some correspondence. Damn she was beautiful. I pulled up the photo on my phone of her in the dressing room where she'd modeled for me the dainty sheer blue bra and panty set that she now wore as she sat before me in her otherwise conservative business attire.

We exchanged a few knowing glances, and I wondered if she had checked her personal email and learned of the delay in her punishment. If she had, she seemed not to show any sign of it. She maintained a strict business façade, such that no one could have guessed that she was my kinky sex slave. I briefly pondered what people in our office would say if they knew that earlier that morning she had messaged me a photo of her in her lingerie selection of the day, as I had ordered her to do daily after I'd replaced every piece of her underwear collection two nights earlier. I glanced at the picture on my phone again, and it made my cock begin to stiffen. I playfully flashed it in her direction, giving her a lascivious look, but I decided that before we got too carried away I needed to distract myself, so I pulled some papers from my briefcase and pretended to read them.

No matter how I tried, though, my mind kept wondering back to the night Nikki and I shared as we shopped for her new wardrobe of bras, panties, corsets, garter belts and stockings. In the middle of my erotic reminiscing, the door to Adrienne's office opened and she stepped out, and asked me in. As I walked past I was certain that Nikki could see the lust behind my eyes, if not the bulge in my pants, as she smiled sweetly at me. So as not to raise any interoffice suspicions, I decided to leave the door to my boss's office open. Too many closed-door meetings would be too dangerous to our little arrangement.

"I'm really glad that we're on the same page about the MLS project, Adrienne," I said casually as I took a seat in front of her desk, using the "MLS" name as code for My Little Slut.

"Me too, Jason," her voice was business-like, but the look in here eyes definitely betrayed the sensual heat that burned inside her.

"But if we're going to take this all the way I think we're going to need to explore some other avenues, open things up a little, take some risks explore the boundaries of convention. You know what I mean?"

"Well, not exactly. But I'm open to hearing what you think. It sounds like you've got some ideas, and I'd like to hear them."

"First of all, there are some holes in the MLS deal that need to be plugged." I reached into my briefcase and pulled the small plain paper bag, which I placed in front of her on her desk. She scooted up to the desk and eagerly peered into the sack. Her eyes widened as she stared down at the black anal plug inside. I wasn't sure she'd know what it was, but clearly she did.

"I suppose you've got some ideas of how we should going about filling in the holes?" she asked inquisitively as she whisked the bag with the sex toy into her desk.

"Oh most certainly."

A wicked grin spread across my face, as I handed her a sheet of paper with some typewritten instructions on it. "This is the first and least difficult idea. Let's start with that. Bigger, more significant ideas will come later." As she read the page over carefully her expression was ambiguous, and I couldn't tell if she was excited, worried, mad or indifferent.

The instructions started with an explanation that she was to begin anal training immediately, with the goal of me fucking her ass at the end of the training period , claiming her anal cherry. I'd learned from her that she considered anal sex to be strictly taboo -- a taboo that I intended to help her overcome. I explained that inside the bag was an anal plug in a size suitable for the first stage in her training. The dice, which were included in the bag with the plug, were to be immediately rolled each morning after arriving at work. She would then go to the ladies restroom, lube and insert the plug and return to her desk, where she was to leave it in her ass for the time indicated by the dice. To begin with, the time would be determined by forming a two-digit number, putting the smaller die roll first. For example, a roll of a five and a two meant mean twenty-five minutes.

Since I knew her husband was out of town again, and would be gone for the next ten days, I explained in my instructions that she was to repeat this procedure when she arrived home from work each evening. While the plug was in she was to think about what it was going to belike to have her ass ravaged by my hard cock. She was not to masturbate to alleviate the discomfort or to fuel her desire or to touch herself in any pleasurable way. All orgasms would continue to be strictly forbidden until further notice.

Adrienne stared blankly at the page for a few seconds, then ran it through her shredder. Without a word, she opened her desk, pulled the dice from the bag and rolled them quietly onto the writing pad in front of her. She picked them up and held the resulting roll toward me. Fourteen minutes. She discretely transferred the anal plug and small tube of lube to her purse.

"Are we finished here for now, Jason?"

"For now."

"I want to get started on this right away. If you'll excuse me, I need to go to the ladies room." She sounded genuinely eager.

"Great."

We exited her office together, me heading for my office, her heading off to plug her ass as instructed.

I watched for her as she returned to the restroom. It was clear to me that her gate was a bit awkward, and I wondered if anyone else would notice. I chuckled to myself at the thought. Shortly after lunch I sent her a text message: "immediately text me the results of each roll." She texted back, "Yes, Sir."

We had no further contact the rest of the day until I received a text message at 6:40 pm that simply said, "34!" I was desperately curious about what was going through her mind during the time during which her ass was obediently filled. Was she offended or excited? Was she humiliated or turned on or both? I wanted to call or text her, but I wanted to minimize contact in order maximize her mental preoccupation with the anal training. So, instead I waited patiently for her journal entry to appear. I was surprised when my computer dinged in the email notification a new entry, even before the time had elapsed.

>> Wow! This is hard for me! >> >> I'm sitting here with a thick black anal plug shoved into my ass. I try to sit gingerly to keep it from forcing its way further into me, but there's not any way to avoid the discomfort of it. And maybe the shame of it is worse than the physical unease. When it comes to anal play, I've never been one for receiving or giving. The funny thing is, when I revealed my revulsion to anal sex to Sir, I knew immediately that he would use it to push me, to test me, to stretch me (pardon the pun!). It was just a matter of when, not if. >> >> What bothers me the most is that I'm sitting here completely turned on - with an incredible fire burning in my pussy. I want to play with myself, but Sir won't allow it. He says I am to simply ponder that ass-fucking he'll be giving me at the end of my training. Truthfully, I can think of nothing else. >> >> HLS

I smiled to myself as I rubbed my cock, stirring from reading her entry. This is precisely the affect I'd hoped for. I added a one-word comment to her blog, "Perfect."

When I received the text "24" Friday morning, I immediately texted her back. "Sorry little slut, big number goes first from now on. 42." I got no reply, but she shot me a nasty glance as she walked toward the restroom past my office.

I was little surprised that Nikki had not commented at all on Adrienne's blog entry regarding her initial reaction to her anal training, nor had she mentioned it to me in her daily writing assignments or our other email and IM exchanges. I decided to interject her more directly in a manner she could not ignore. While Adrienne was in the restroom stuffing her ass with rubber, I hurried to Nikki's desk. I handed her another brown paper bag, which contained the next larger size anal plug.

"Look inside," I said quietly.

She opened the bag and peered in, then looked back at me questioningly, as if unclear as to why I had given this to her.

"Is this for me?" she asked, almost hopefully.

"Would you like it to be?" I asked, teasing her purposefully.

She leaned toward me and whispered in a barely audible voice, "All of me belongs to you to use as you wish, Sir."

She was doing her best to remain submissive, but the look in her eyes begged me for her punishment.

"It is for you." I paused just long enough for my statement to register; just long enough for a slight smile to come to her lips. "It is for you to give to Adrienne sometime this afternoon. Tell her I wanted to scale up the training immediately."

I felt a little pang of guilt as the look of disappointment spread over her face. My decision to use her to further Adrienne's training was perhaps cruel, but despite appearances, this was an intentional part of Nikki's punishment.

Friday night my little slut rolled for an incredible 53 minutes worth of anal stimulation using the medium-sized plug. Despite the new plug and her unfortunate roll, her journal entry that night seemed to indicate a growing physical and emotional comfort level with her training, so after receiving the text "31" Saturday morning, I decided to move to the next stage of her preparation: mental preparation.

I sent her an email late in the morning instructing to come online at 7 pm that night, before making her evening roll. I told her to have the dice, plug and lube handy.

She logged in to IM at 6:59.

*slut* Good evening, Sir

*Sir* Good evening little slut. Do you have what you were instructed to have?

*slut* Yes, Sir. All ready.

*Sir* Good girl. Are you naked?

*slut* Was I supposed to be? Did I miss that?

*Sir* You didn't miss anything. I'm adding it as a new requirement for any plug time while you are at home. Now strip.

It took less than a minute for her to return.

*slut* Naked, Sir.

*Sir* Good girl. How are you enjoying the new size?

*slut* Ummm. Enjoying?

*Sir* Enduring?

*slut* The 31 this morning was definitely easier than the 53 last night, but I think I'm learning to accommodate its girth alright.

*Sir* It is supposed to be punishment after all.

*slut* Oh it certainly fits in that category.

*Sir* Well, physical training is only part of the equation. Mental training is also important. So we will begin taking that to the next level as well tonight.

*slut* Yes, Sir.

*Sir* Do you know why I want to fuck your ass, little slut?

*slut* Besides the good tight feeling around your hard cock? (smile)

*Sir* Besides that.

*slut* Because it's something you know I have an aversion to and you want to use that to punish me?

*Sir* Partly. But it's more than that. This is something that I want you to give me that no one else has ever had. It means more because it's something I know that is hard for you to give. It requires you to yield yourself to me beyond your comfort zone.

*slut* It makes me more owned, more owned that I have been by anyone else before.

*Sir* Exactly. You understand well. Good slut. Now roll the dice, please.

*slut* 22. Phew!

*Sir* Lucky little slut. Stand up, legs spread.

*slut* Standing and spread as directed, Sir

*Sir* Ask me for permission to fill your ass with the plug.

*slut* Please, Sir, may your little slut fuck her ass with your plug?

*Sir* Tug your nipples until they burn. Do it until I tell you to stop.

I waited thirty seconds or so.

*Sir* Harder slut. Come on. Twist them. Pull them. Pinch them. They are mine and that is how I wish them to be used.

Another thirty seconds passed.

*Sir* Stop.

*slut* Thank you, Sir.

*Sir* You have earned an inch of the plug. Only an inch. First you will put it in your very wet pussy for lube. Hold it there with your pussy muscles.

*slut* Yes Sir. You knew I'd be soaked, didn't you? You know your little slut so well.

*Sir* in?

*slut* Yes, Sir. God that feels so fucking incredible.

*Sir* Your hands will be busy, so no more typing. Keep your eyes on the screen. Do exactly as I say, when I say. When I ask you to say something, say it out loud.

*slut* Yes Sir. Thank you Sir.

*Sir* Fuck your pussy with my plug. Do not touch your clit and do not dare come.

*Sir* Beg me to fuck your ass, slut.

*Sir* I'm not buying it. Beg me. For real.

*Sir* You may have one inch. Not a bit more. Put my plug an inch into your ass, slut.

*Sir* Fuck your ass with that inch. In and out. Fuck it.

*Sir* Good slut.

*Sir* Beg me for another inch, and then take it. That's it. No more than two inches now. Now fuck your ass. Stretch it with my probe.

*Sir* Beg me for the rest, now, slut. Beg me while you slap your tits with your free hand. Hard. Make them sting. Slap them.

*Sir* Stop. Take out the plug and come back to the keyboard.

*cunt* Did I do something wrong, Sir?

*Sir* First, you didn't slap your tits nearly hard enough. Then you took more than the two inches I granted you. Don't deny it, because I know you did. Even as you were begging me for it all, you shoved it into your ass all the way.

*cunt* Yes, Sir. Sorry. You know your slut well.

*Sir* I'm going to go now, but I leave you with these instructions.

*Sir* Your 22 minutes hasn't officially started yet. This was warm-up. I want you to kneel, naked on all fours, and beg out loud for me to fuck your ass. Only you won't be asking for the plug, you'll be asking for my cock. Beg well, little slut, like I know you can. Then fill your ass full with it. Imagine my hard cock entering you, splitting you open. Surrender your virgin ass to me.

*slut* Yes, Sir.

*Sir* Every five minutes, remove the plug, beg me again for my cock. Then fuck your ass hard with it for at least a minute, all the while telling me how good it feels to have your ass filled, how much more you want it, how much harder you want me to fuck your sweet little slut ass. You can rest another four minutes, kneeling and plugged, before repeating this five-minute cycle. Is this all clear to you slut?

*slut* Yes, Sir. Thank you, Sir.

*Sir* Good night, little slut. Use your ass well. Your training will soon be completed, and then you will have the real thing.

*slut* Good night, Sir.

I read later in Adrienne's blog that she had never before believed that anal orgasms were real. She was now a believer. She claimed to have had to slow down her ass-fucking with the probe in order to keep for sending herself over the edge. My cock throbbed at the thought.

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Sunday morning I sent Adrienne a cell phone snapshot of my hard cock, telling her how hard her blog entry made me. I ordered her to lay her phone down in front of her, as she knelt naked on all fours again for her morning training session, and to focus on the picture as she repeated the five-minute ritual from the night before. She rolled a 49. Her ass would be raw!

Sunday night I added tit-slapping and nipple pinching to the ritual. While she begged for my cock, she was to brutalize her tits to the point of pain. I explained that the intent was to remind her that her entire body belongs to me. I can choose to do with it what I will. I knew Adrienne was no pain slut. In fact, I knew that she possessed a rather low pain threshold and gained little erotic pleasure from it beyond the pleasure of submission. I told her that I knew that this, for her, was pure punishment, and I expected it to be viewed as such; part of the cost of the orgasm I granted her after defeating Nikki in the orgasm race. She seemed to except it without argument. She was probably very thankful that she rolled a 21.

I phoned Adrienne on her way into work Monday morning and instructed her to park in the normally deserted lowest level of the underground parking garage to our building.

"I suppose you recall the brutal face fucking I gave you there the day after you agreed to be my little slut," I reminded her.

"I think of it every time I pull into the parking garage."