Who's The Boss? Ch. 09

"And it makes you wet every time, doesn't it?"

"Yes, Sir."

"This morning we'll be adding a new dimension to that memory. When you arrive, step out of your car. Then I want you to unbutton your blouse and leave it hanging open while you crawl on your hands and knees from your car back to the alcove where I violated you last time. Facing the corner, you'll wait for me there on your hands and knees. Do not move or look around unless I explicitly give you permission. Understand?"

"But, Sir, my stockings will be ruined! And what if..." she started to protest before I cut her off.

"Don't question my orders, slut, unless you want me to have you do it naked instead! Now, just do what I say." I hung up without waiting for her reply.

Fifteen minutes later, Adrienne pulled her BMW into the space closest to the stairway alcove that was her destination, leaving her some 30 feet to crawl. I watched from dark shadows behind one of the large concrete pillars as she stepped out of her car. Very slowly she unbuttoned her shirt while craning her neck around, looking for signs of anyone else that might unexpectedly intrude on our escapades. She looked around again, and then dropped to her hands and knees. I watched her ass wriggle as she frantically crawled toward the alcove to which I'd directed her. I gave her a few minutes to contemplate her situation, knowing her nerves would become more frayed with each passing second, and then I strode slowly toward her, making as much noise with my feet as possible.

I rounded the corner behind the stairwell to see my boss kneeling with her head in the corner. She was breathing hard.

"Sir?" She whispered anxiously as I approached. I didn't respond.

"Sir?" She said again, the desperation in her voice clear. I said nothing, yet she obediently stayed in position, as commanded.

I stopped directly behind her, out of her line of sight, and I reached down to lift her skirt and expose her bare backside. I tucked her skirt into her garter belt to keep it up and out of my way for what was to come.

"Mmmm," I sighed, placing my hand on her ass and giving her cheek a squeeze. "Such a good and obedient little slut."

"Oh Sir," she sighed deeply. "I am so freaked out!"

"I know, slut, yet you obeyed. I am proud of you," I said calmly, as I ran my hand over her the exposed flesh of her sexy behind.

"Thank you, Sir."

"Don't thank me yet. We aren't nearly through yet."

Adrienne started to swing her head around toward me. Immediately I slapped her ass hard with my open hand, sending a loud smack echoing through the deserted garage.

"Still!" I said firmly. "You've not been granted permission to move or look around."

"Sorry, Sir," she whimpered, shifting her head back toward the corner again.

I moved next to her and squatted down. With one hand I reached under and grabbed her tit, squeezing it aggressively. With the other I smacked her ass again. She yelped, but said nothing. I gave each of her ass cheeks a few more hard swats.

"Do you know what that was for?" I asked.

"For moving without permission?"

"No, because it's my ass and I can do with it whatever I please, can't I?" I smacked her ass again, harder than I had yet.

"Yes, Sir," she squealed.

"Yes, Sir, what?"

"Yes, Sir. It is your ass to do with as you please." Her voice was shaky. I could tell she was either holding back tears or still scared to death of someone coming upon us.

"I can even fuck it if I want, can't I, slut?"

"Yes, Sir. As you wish."

"Mmm. As tempting as your ass looks to me right now, and as hard as my cock is, your training is not yet complete."

I roughly pulled down the cup of her bra, exposing her left breast, and then cupped it with my hand, gently tweaking her nipple between two fingers. She moaned softly in response. I slipped two fingers of my other hand down over her pussy lips, which I found pouting and swollen and wet.

"You are frightened. You are in pain. Yet you are very aroused. Can you explain this to me?"

"No, Sir."

"Do you not sense your own arousal, slut?" I pushed the two fingers into her cunt.

"No, Sir," she said, squirming back against the intrusion and clenching her muscles around my fingers. I pumped them into her several times, coating them liberally with her juices. I moved them quickly up to her puckered asshole, and I slipped one finger into her forbidden hole without warning. She took it easily and moaned softly in response. I added a second finger, and she only groaned at the increased stretching of her ass.

"The truth is that you like me taking you beyond your limits. You claim not to enjoy pain, yet when I spank you, you become sopping wet. You claim not to enjoy anal stimulation, yet your body betrays your desire for my violation of your ass. You want me to fuck your ass now, don't you slut?"

"No, Sir. I mean, yes, Sir. I mean, it is yours to do with as you wish."

"Good slut! You are getting it. That's really what it's all about isn't it. Being taken completely. Being totally consumed. Being owned entirely."

"Yes, Sir, I want you to have everything. I want to hold nothing back."

I withdrew my fingers and released her tit from my grasp. From the pocket of my sport coat I took out the third and largest size anal plug.

"Open your mouth, slut," I commanded.

She opened her mouth and I forced the large plug in, stretching her jaw to open wide to accommodate its width. I left it there until drool began oozing from around the corners of her mouth and dripping onto the pavement beneath her. I removed the plug and shoved it unceremoniously into her pussy. She squealed and sighed.

"Hold it there, slut, while I prepare your ass to accept my final plug."

I took a small tube of lubricant from my pocket and drizzled over the crack of her ass. I worked it into her anal passage, first with one, then with two, and then with three fingers. By the time all three fingers were stuffed deeply into her ass, she was panting and groaning.

"I think you are ready. Do you?" I asked.

"Yes, Sir," she gasped.

"Beg me for it then. Beg for my plug."

"Please, Sir, will you put your big fat plug into my slut ass?"

I yanked the thick black rubber toy from her pussy and pressed the tip in past her sphincter. She took the first inch almost without notice. The next inch of the quickly thickening toy met with some resistance and extracted hard sigh from her. The third inch stretched her open wide and she began breathing deeply, grunting with each exhale.

"More, slut?"

"Yes, Sir. I want it all," she groaned forcefully, willing herself to accept whatever I would give her.

With that I gave a final push and the widest part of the toy passed into her, her anal ring closing around the narrower base, as the flange came to rest against her cheeks.

"Good little slut. All in."

"Thank you, Sir," she sighed in relief.

"Now, you'll count to fifty while I go, and then you will crawl back to you car, just like this. Skirt up, shirt open and tit hanging out of your bra, ass stuffed full of my plug. You'll have to go home and clean yourself up, of course, because you are a total mess."

"Yes, Sir. Thank you, Sir."

I left, having never once made eye contact with my little slut.

I went to my office reveling in the ravishment of my slave, my boss. I could tell that physically and mentally I'd stretched her as far as she'd ever been stretched before. I also knew that she accepted it willingly, but not without struggle. I knew a sense of pride would be welling up along with the abject humiliation of it all.

I sent her a short text message. "Well done, little slut. Bring me your tattered stockings as a memento of our morning and a symbol of your total surrender."

- - - - - - - - - - - - - - - - - - - - - - -

Ninety minutes later Adrienne came to my office door and knocked softly.

"Come in, Adrienne."

She stepped inside and greeted me pleasantly. "Good morning, Jason."

I looked at my watch. "Rough time getting started this Monday morning?" I jested.

"You might say that," she replied almost playfully. She opened her purse and tossed a wadded up pair of ripped stockings onto my desk before gingerly shuffling off toward her office, doing her best to mask any sign that her ass was stuffed with a two and a half inch thick anal plug.

As soon as I saw her log into her computer, I sent her an instant message informing her that Nikki would be in shortly to remove the plug from her ass. I got no reply.

That afternoon I arranged a meeting with Adrienne through Nikki using the MLS guise.

"I think the holes are filling in rather nicely with MLS, don't you?" I asked, sitting across from her and smiling broadly, her office door open again.

"Yes. I'd say things are progressing well. I must say I'm looking forward to see how it all concludes."

"If you don't mind, I've had a few thoughts on how to help things along to that end."

"Sure. Whatcha' got for me?"

"This," I said as I handed her another written instruction. This sheet explained that she would receive at her home in the mail that day a life-sized replica of my fully erect cock, made for her by me personally using one of the clone-a-dick kits. I explained that I made myself hard by stroking my cock while imagining it poised at her quivering asshole, ready to take it for the first time, to savagely claim it as my own. That night, my instructions continued, she was to kneel on all fours, naked, on her bedroom floor as she had for the previous sessions. For a full thirty minutes, every five minutes she was to slap her tits and pinch her nipples, as before, and to beg out loud for my cock to take her ass. This time, however, she was not to put anything in her ass or even touch it. Rather, she was to simply stare at the fake cock lying before her on the floor and imagine it plundering her back door.

She finished reading and her face flushed red as she looked up at me with a slightly questioning look. It was clear that she wanted to say something but worried about someone hearing through her open office door.

Finally she said straightforwardly, "I think this will work."

"Good. Very good," I replied. "I was hoping you'd feel that way."

I gave her Tuesday morning off from anal training, and then had her repeat Monday night's ritual that evening. Same thing for Wednesday. By Wednesday night, her journal indicated that she was positively desperate to have something in her ass. She found herself completely preoccupied in anticipation of the time when at last she would have the experience she was now longing for: to have her ass fucked by me.

- - - - - - - - - - - - - - - - - - - - - - -

The stage had been perfectly set.

I sent Adrienne a one-word email shortly after lunch on Thursday. "Tonight."

I rang her cell phone a few minutes after I watched her leave the office. Not too surprisingly it was at least an hour earlier than she usually left.

"Eager to get home?" I asked her coyly.

"Very eager, Sir."

"But you don't even know what I have planned."

"I doesn't matter, I couldn't work another minute anyway. I haven't gotten anything done all afternoon."

"You want this that badly do you?"

"Oh yes, Sir. I want it very badly."

"Who would have thought just a week ago that you'd be saying such a thing," I teased.

"Not me, that's for sure," she quipped.

"Well, I'm not going to give you the whole plan just yet, but step one is that you need to stop and get yourself an enema kit on the way home. Strip naked and follow the directions on the kit when you get home. I'll phone you later with more instructions. Don't touch your pussy, no matter how tempted you are."

"Yes, Sir," she replied.

At 7:20. She answered breathlessly on the first ring. "God, Jason, I thought you'd never call."

"Have you done as I instructed so far, my little ass-slut?"

"Yes, Sir. I am all prepared for you. I have been prancing around here stark naked for over an hour. I feel like my mind is going to explode."

"Afraid or excited?" I asked.

She paused to consider the question. "Both."

"Good girl. Are you wet?"

"Yes."

"Let me hear. Two fingers."

She lowered her cell phone down to her sex, and I heard a faint gasp at the obedient insertion of her two fingers into her wet cunt, just before I heard the sloshing of those same fingers as she pounded them in and out of her pussy. I listened to her finger herself furiously for twenty or thirty seconds before returning to the phone, practically gasping for breath.

"Oh fuck, Sir, I almost came. I had to stop. I knew I shouldn't come. But I'm so keyed up!"

"Good girl. You know coming is still not allowed. Yet. You've obeyed me on this matter haven't you? You haven't come since your ass training began have you?"

"No Sir. I haven't. But I have wanted to desperately. My need is so strong."

"I heard the need dripping from your pussy just now, little slut. But it isn't really your need after all, is it?"

"No Sir."

"To whom does the need in your pussy belong?"

"You, Sir."

"And to whom does the need in your ass belong?"

"Every part of my being is yours, including the extreme need my ass has to be filled with your beautiful cock."

"I'm parked up the street from your house right now. I'm stroking my raging hard-on thinking about how good it's going to feel inside your sweet little slut ass. Mmmmmm. It won't be long now."

"Ooooh god, Sir, please come and fuck my ass! Please!"

"As I recall from last year's Christmas party, your front entrance is pretty well hidden from the street and neighbors, so I should be able to use it without being seen, right?"

"That's right, no problem."

"Good. Here's what I want you to do. First, go find something to blindfold yourself with, and get the life-like dildo I made for you. Then I want you to unlock your front door, disable the alarm, dim the lights, and take a seat on the leather loveseat next to the fireplace in the living room and put on the blindfold."

"And where shall I put your cock?" she asked playfully.

"Well, you already know where I'm going to put my cock. But as for the dildo, just set it on the coffee table in front of the loveseat. Now hurry and go do as I said, and I'll be coming in shortly."

"Yes, Sir. I hope you will be coming soon, and right in my ass. I am so desperate for you!"

"One final thing. No speaking or sounds from you unless you are asked a direct question or unless given explicit permission. Understood?

"Yes, Sir."

I have to admit that by the time I slipped through the front door, my heart was pounding with anticipation. The fact that I was about to take my boss's virgin ass right there in her own home was almost more than I could stand. I gave my eyes a minute to adjust and made my way through the dark foyer toward the dim light coming from the living room.

I stopped dead in my tracks as soon as I caught sight of her. Suddenly my heart raced with something beyond the exhilaration of what I was about to do. No this was a different feeling, vaguely familiar, but one that had become a distant memory for me. I paused in the arched doorway to gaze at the sight of the beautiful woman sitting naked and blindfolded on the loveseat.

For more than a minute, I stood staring, drinking her in. Candlelight flickered gently off her skin from the candlesticks on the end tables on either side of her. The blindfold she'd chosen, a black silk scarf, could not dim the look of eager surrender on her face. Even her posture, back straight, tits out proudly, hand resting submissively on her thighs spoke of her enthusiastic compliance. I considered in that instant how willingly this woman had embraced all that I had led her into in the short time she'd come under my control. I knew that no matter her own comfort level she would give me anything I desired from her.

Hers was a level of submission that I had never known before, and I found it overwhelmingly beautiful.

At last I spoke, choking back the emotion. "God you are so beautiful sitting there like that. You just might make me fall in love with you after all."

"Sir! At last." Whether she was commenting on my arrival or my previous statement, I did not know.

"Shhh. Quiet, little slut, unless I ask you to speak." Adrienne nodded her head in acknowledgement of my command.

I approached her quietly from behind and dropped my small duffle bag, filled with the night's necessary implements, onto the loveseat next to her. She flinched slightly in surprise. I rested my hands on her bar shoulders. "Easy. You are a bundle of nerves little slut. Relax."

I massaged her shoulders and neck for a minute or so, and I felt the tension ease from her body. I leaned forward and moved my hands down her from neck, slowly down her chest until they came to rest over her breasts. I squeezed them gently and toyed with her nipples a bit. I could tell she was fighting back the expression of her desire, striving to remain silent as commanded. I pinched harder, and she gulped against the yearning to moan. I twisted her nipples, finally evoking a guttural groan.

I slapped both her tits at once. "Silence, slut!" She breathed in suddenly and deeply, fighting off the cry that was trying to force its way from her lungs.

"You like it better when I'm the one doing this, don't you."

She nodded, and I slapped her tits again, harder. "Answer me when I ask you a question!"

"Yes, Sir. I like it better when you slap my breasts and pinch my nipples. When you had me do it to myself, I always imagined it was you doing it to me."

I relented and cupped one of her sweet mounds in each palm. "Mmmm. These are lovely, and I love it that they are mine." I brushed my open palms gently against each nipple as they stiffened proudly. I leaned in closer, inhaling the scent of her perfume, and then kissed her neck softly.

"Suppose I should tell you that I want to pierce your nipples as sign of my ownership of them?" I asked.

"As you wish, Sir. As you say, they belong to you."

"You continually amaze me, my little slut. Your level of surrender is rather astounding to me." I went back to kissing her neck while continuing to gently and playfully stroke her breasts and nipples.

"Are you prepared to accept the conclusion of your training and the culmination of your punishment tonight?"

"Yes, Sir. I have been longing for it all day, all week."

"Longing for what? Tell me."

"Longing for you to fuck my ass, Sir."

"This is what you want then?

"Oh yes, Sir, please. Please fuck my ass, hard and deep; any way you want to. Just let me feel the thickness of your wonderful manhood inside there, filling me and claiming what no man has ever claimed from me."

I came around the loveseat and pulled Adrienne to her feet. I stepped back and drank in her nakedness with my eyes. In that moment an unexpected wave of pure adoration swept over me, causing me to feel positively dizzy with emotion.

"I'm falling for you, little slut. You know that don't you."

"Yes, Sir. I was hoping. I've never stopped hoping."

I stepped toward her and kissed her tenderly as I slid my hands over her shoulders and down her arms until our fingers intertwined. Without a command, she slipped to her knees and deftly removed my cock from my pants, gulping by my hard flesh in mere seconds. She sucked and licked and worshiped my cock with absolute pure desire, as I stood over her watching.

My balls began to well up need, and I found myself suddenly on the brink. I forced myself from her mouth, reluctantly.

"It's time."

I raised her to her feet and led my blindfolded sub to the adjacent dining room. Her hands and body trembled slightly from fear and excitement. I moved the chair from the head of the table and positioned her in front of that end. I had her lean forward slightly so she could place her hands on the table for support.