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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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.
