Family Business Ch. 08

I was pleasantly satisfied to see him blink in surprise, then that smile tugged at his lips again. I had impressed him I thought as a warm feeling spread through me.

"An interesting move Ashley, now how many times should I spank you for what you did? If I am not satisfied with your answer, I will double it."

I had been considering this as well. "I am 22 years old, that should have been enough time to learn respect. I think you should hit me for each year that I have failed to do so."

He walked over to where I was restrained, on hand sliding down my back and over my ass. I shivered at his touch and steeled myself for the spanking I had negotiated. His hand slid over the curve of my ass, gently caressing the smooth sensitive skin. I felt his fingers slide between my legs and squirmed as he probed my pussy lips. He said nothing but I knew he could feel how wet I was already.

"Your terms are acceptable; you will count the strokes." He said, then I yelped as the first blow landed.

"One!" I called out, then "Two, three, four." As he continued. He paused at five, his hand gently stroking my sore butt cheek. I heard him move around and he took up position on my other side, one hand firmly in the small of my back as he continued the punishment.

"Thirteen, fourteen, fifteen." I whimpered, my voice no longer clear and firm. My ass burned, every blow like a nail being driven into my flesh and the pauses in between just made the pain of the next blow worse. I was biting my lip, tears oozing from beneath my clenched eyes.

"Do you want me to stop?"

I took a shuddering breath. "No, no, this is what I chose. I will take my punishment."

Dan moved around where I could see him and crouched down so he could look me in the eye. "You have never really been treated like this, haven't you?"

I shook my head, I couldn't remember the last time I had been in this much pain. Even after what I had gone through over the last month, this deliberate and measured application of suffering was more than I could take.

He took my chin, lifting my head so I was looking at him. "Abiding by your agreement is admirable, but not when it isn't the only option. Do you want to re-negotiate the deal?"

A flash of hope, then I paused. This had been my idea and I didn't want him to think I was weak especially now that I had just started to earn his respect, but I had not realized just how much this was going to hurt. I closed my eyes and nodded, a feeling of shame bringing the tears now.

I felt his hand stroke my cheek, his thumb wiping away a tear and I looked up to see him crouching in front of me again. Strangely, he was smiling with that same look that he had given me when I showed him the video, a mix of pride and approval.

"Learning to accept that you made the wrong choice is actually more important than making the right one. You will be wrong more than you are right and accepting that before you get too committed is a skill that not many people have."

I nodded dumbly, barely hearing his words as I was lost in his eyes. Their normal ice grey had somehow melted and they were actually warm and welcoming, wrinkling at the edges with the rare and priceless smile of approval he was giving me. I took a deep breath, my breasts pushing into the leather of the bench as I fought to hold back the tears I felt. This monster, this animal who had abused me and my mother for the last month and a half was actually human.

Then the moment was lost, he stood and stepped back crossing his arms in the businesslike pose I was so used to. "Well, what is your counterproposal?"

I gulped to get myself under control but I was still nervous that my voice would crack with emotion. A couple of breaths and I said in a voice full of confidence I didn't feel "The last time I sucked your cock was when Claire was here, and she did most of the work. I propose that I show you what I have learned since then. Instead of punishment, I will pay my debt with pleasure."

He paused, then nodded "I accept your terms, but you remain tied. I like it." Soon I was unstrapped from the bench and tottering on unsteady legs as my ass throbbed with each movement. He walked past me, ignoring my struggles as he moved to the chair. His pants fell to his ankles and he stepped out of them before seating himself comfortably. I noticed with satisfaction that cock was already semi-hard but I still shuddered at the sheer immensity of it. I gulped and steeled myself, I wouldn't fail twice.

I gritted my teeth and slowly walked the short distance to where he sat. Ignoring the pain I crossed my legs in front of each other as I tried to achieve the same sensual swaying strut that Clair pulled off so naturally. When I reached him, I paused, legs slightly apart and one hip thrust out. If my hands were free, one of them would be on my hip while the other would trace the line of my cleavage above the white leather bustier of my corset. Instead, I took a breath to thrust my chest out and softly ran my tongue over my lips.

Dan looked up at me, his face a mask but I noticed that his cock twitched at my display and a small smile pulled at the corners of my mouth. I was doing it, he couldn't wait for me but I could make him, I was in charge now. I slowly knelt before him, it was awkward with my hands tied but I managed to do it and his eyes followed me with a hint of eagerness. I sensually rolled my shoulders as I settled between his legs, my ass was screaming in pain but I blocked it out. With a toss of my head to get my hair out of my face, I leaned forward to gently kiss the tip of his cock.

"Thank you for agreeing to this, I hope you will find my services satisfactory." I murmured as my lips slid slowly over the thick head of his prick while my tongue gently massaged his piss hole. His cock swelled in my mouth, becoming rigid and even thicker than I remember as I turned my head and kissed my way down the long shaft. I looked up at him through my dark lashes, my eyes as wide as I could make them and I hoped twinkling with the same look of mischief that I had seen in Claire's that night. I saw his hand twitch, as if he was fighting the urge to grab my hair and take control of the situation. I sighed with satisfaction and his cock jumped as my cool breath flowed over it.

I tugged at my bonds, instinctively trying to reach out and cup his balls like Claire had showed me. Instead I leaned down and nuzzled them with my nose, my lips giving them gentle butterfly kisses as my tongue slid up the seam between them. Dan's legs flexed, pressing against my shoulders so I continued, moving from one ball to the other as I listened to his breath speed up. With a final kiss I rose up to lick the underside of his now rock hard cock all of the way to the tip before slowly taking it in my mouth.

I moaned, both for effect and in dirty self-pleasure as his thick shaft filled my mouth. I hated this man, but here, now I was enjoying myself. He groaned as I sucked as much of his shaft in as I could. Nowhere near what Claire or Mom could achieve but I pushed as far down as I could with my tongue sliding around the thick member filling my mouth. I held it there, sucking and licking, twisting my head around his prick in a corkscrew motion all the while moaning quietly in satisfaction.

Out of the corner of my eye I saw Dan's hands clench again, his fingers digging into the plush leather of the armchair. I had done that, I had made him react to me just like he made me react like a programmed machine. I repeated the motion and his hand clenched into a fist while I felt the cock in my mouth throb. He was getting close so I backed off, slowly sliding up until my pink lips were barely kissing the tip.

I looked up at him, his eyes were closed and his head back lost in the sensation. I quickly flicked my tongue up the bottom of his shaft and he jumped with a sharp intake of breath. I could see his eyes clench in pleasurable frustration. I could stop right now, stop and leave him like this. The punishment would be severe but I would have won. I briefly thought about it then slowly slid my mouth back down his cock, the reward was not worth the cost I heard his voice say in my head and he moaned again as I twisted my mouth around his shaft.

I felt his cock throb again, he was going to cum soon and I didn't want to tease him any longer. I bobbed my head up and down like a piston, the head of his prick striking the back of my throat and threatening to gag me. Despite my best efforts, I couldn't get more than a third of his cock in my mouth but that didn't seem to matter. His fingers dug into the arms of the chair as his ass clenched and I felt his body vibrate. I braced myself and soon his cum exploded into my mouth.

It was like a firehose and I struggled to swallow as spurt after hot spurt exploded on my tongue. I kept my lips latched firmly on his shaft, making sure that no jizz leaked out as my throat worked hard to clear my mouth before the next explosion. Finally, after what seemed like a gallon of cum he stopped. With a long sigh he melted back into the chair and I relaxed and took a breath. The smell of leather and cum filled my nostrils as I slowly backed off of the thick penis, my tongue working to catch any last drops.

I leaned back, my sore ass forgotten in the satisfaction of what I had just accomplished. I was kneeling at his feet, in heels and stockings with my arms tied behind my back but I had taken control. I decided when and if he would be satisfied and the feeling of power made me smile as I licked my lips. I looked up at him as he took another deep breath, then his eyes opened and he looked down at me. For a moment we sat there, just watching each other in silence.

"Excellent job, Ashley. Stand up and I will untie you." He said, putting his hands on my shoulders to help me from my knees.

"Wait, what?" I replied in surprise, and he stopped tilting his head like a curious puppy.

"The terms of the agreement have been met, you have apologized to my satisfaction. Stand up and I will remove your bonds and you can go." He replied, a small smile tugging on his lips.

"Uhhhh.." I mumbled as my brain went into overload.

I was done, he was going to let me go, why was I hesitating I asked myself.

'Because you are horny as hell and had been waiting for this moment for the last 24 hours dumbass.' Another part of my brain answered. Well, I don't think it was my brain as I felt the dampness on the back of my legs from where my pussy had been pressed.

This man had forced himself on me, threatened my mother if I didn't do what he wanted. He shared me with his psychopath of a son and has stolen your family inheritance. You hate him!!

This man is an incredible fuck, he has taught you things about your body that you would have never learned. He introduced you to the most incredible woman you know and showed you that you could love your mother in ways you never thought possible.

This man is an animal, a monster. He has kept you prisoner here and turned you into his personal sex slave. He humiliated you, abused you, tortured you and you just sucked his cock to keep him from beating you. Get the fuck out you stupid bitch!

This was all your idea, you chose the punishment and the alternative when he gave you the chance. He has taught you more about being an adult, a woman, than you ever learned in school. He could take you right now without a fight, but he is offering to let you go because you met the terms that you agreed to.

"Well?" I heard, and started a bit in surprise. I looked up at him, that cocky smile on his face but somehow his eyes were pleasant, even mischievous.

Fuck, fuck, fuck, fuck. My pussy was soaked, my tits ached despite the silk lining of the cups of my corset. I flexed my hands and tugged at whatever was binding my elbows together, the feeling of helplessness and submission flowing over me like a warm bath.

"I want you to fuck me." I blurted out before I could stop myself.

Dan leaned back in the chair, his eyes twinkling but the rest of his face impassive as always. "I don't respond well to demands, especially from bound women kneeling at my feet."

I took a deep breath "Please, please fuck me, sir." I said in a soft voice, part of me still screaming to stop.

"Earlier I used a word to describe what I wanted to do to you. You were standing over there and I whispered it in your ear, what was it?" He replied in a soft but firm voice.

My mind raced, what had he said? He was talking about how I was dressed in white, innocent, pure... "Please sir, please defile me."

God that word, what was it that send a shiver up my spine. "Please, defile me." I repeated, looking up at him.

It was like a dam had broken, or a wall had gone up in my mind and the voice that was screaming at me to stop was suddenly silenced.

"Defile me, fuck me, take me please. Shove that cock in my cunt and make me your whore!" I blurted out, each word louder until I shouted 'Whore' to the world.

Dan smiled that confident contented smile that had always set me on edge, but now it just made me want him more. Here was a man who could take me whenever he wanted, but instead he was making me beg him to fuck me. How he had done it I had no idea, I was just desperate for his cock inside me and my deep gasping breaths punctuated my words as my chest heaved with arousal.

He leaned back in his chair, gesturing to his now semi hard cock that was rapidly deflating. "My dear, I would love to but I am afraid that I am in no position to accept your proposal."

I dove forward, my mouth wrapping around the head as I shoved my face down towards his pelvis. There was no seduction, no teasing this time. I whimpered in frustration as my lips, teeth and tongue worked desperately to revive the object of my now burning desire. I licked and sucked like never before, managing to get his cock even deeper into my mouth as I felt it inflate again. Please, please get hard, oh god please I cried to myself, the sounds coming out like desperate whimpers and groans around the shaft filling my mouth.

After what seemed like forever his prick started to respond. Encouraged, I worked even harder and finally it was as thick and rigid as I could make it. I backed off, looking up at him with pleading eyes.

"Please, please fuck me. Shove that prick inside me, treat me like the slut I am." I whimpered.

"Well, I had no idea you had such a dirty mouth girl. Have to do something about that, can't have you screaming whatever you want you know." He chuckled as he pulled a gag out from somewhere. It was not the usual ball or bit gag, instead this looked like a strip of white vinyl with a big knot tied in the center.

I opened my mouth, leaning forward as he pushed the thick knot between my teeth. I ducked my head so he could tie the material behind my neck and moaned in pleasure as the gag tugged against the side of my mouth. The taste was surprisingly good, I couldn't describe it as I ran my tongue over the folds as I chewed at the lump. It stretched and I assumed it was the same material that he used to bind my wrists and elbows.

After tightening the knot, he leaned back in the chair and gestured to his cock. "Well, this is what you wanted so climb on."

I rose to my feet, unsteady because of how long I had been kneeling. His offer to help had apparently expired and he just sat there as I staggered for balance. Dan pressed his legs together then with a gesture of his hand said "Well?"

My eyes fixed on the giant redwood sticking up and gingerly shuffled forward so I could climb onto the chair. The silky material of my stockings slid easily between his legs and the leather arm of the chair and soon I was in position. I squirmed, trying to line up my pussy with the bulbous head of his cock and with a groan of satisfaction slowly slid down on him. Between the saliva on his prick and how wet I was, he went in effortlessly and I bit down on the gag as he filled me. I savored the slight feeling of discomfort as his massive cock slid into my body and soon I felt my clit press against his pelvis, he was totally inside me.

"Nnnnnggggghhhhhh." I groaned around the vinyl ball in my mouth as I slowly bounced up and down on his shaft. It was just as I had remembered it, how could I have hated this feeling. I could feel my vaginal walls stretching and contracting as the head of his cock moved like a misshapen piston and I paused at the bottom and top of each movement to savor the sensation. Fuck, it felt like it was going to come out my throat when he was fully inside me, and the flared head of his cock managed to nudge against that magical spot he had showed me as I slid up the length of him.

I felt his hands slide up my thighs, tracing the lacy tops of my stockings before wrapping around to grab my ass cheeks. I flinched in anticipation of pain but instead his fingers gently glided over the sore flesh, lines of sensual fire that sent a shiver up my spine. I leaned forward, pushing my tits into his face, god they were sensitive.

"Mease aab I eets, meeese" I mumbled around the gag. He might not have understood the words but the gesture was clear and he reached up to squeeze my breasts through the corset. Fuck, why hadn't I worn the cupless one I groaned to myself as he teased me. I whimpered in frustration as I shoved myself down on his lap, gyrating my hips to grind my clit against his pelvis. He flexed his legs and ass, shoving his cock even deeper and I squeaked in surprise.

"Like that don't you?" He muttered with a smile, then he reached around to grab my ass and stood up from the chair. I leaned forward instinctively as my legs wrapped around his hips. One hand came up to hold me against his chest while the other kept my crotch firmly pressed against his. He thrust his hips forward, driving his cock deeper each time.

"Mmmhhh, nnngggg, mmppphhh" I grunted, each thrust sending a flash of painful pleasure through my body. God he was big, and this position made me instinctively tighten my legs and hips which made the sheer size of his cock even more pronounced. I bit into the gag and my hands clenched behind me. It felt good but I didn't know how much more I could take and a whimper of discomfort escaped me.

He must have heard it because he started walking across the room until I felt him set me down on the padded bench. He gently helped me lay back and the relief was incredible as we changed position. Almost as if I had been stretched out, his prick felt more natural with almost no discomfort at all now.

"Mmmmmmmm" I moaned, my eyes closing in sensual bliss while he spread my legs. He took me by the ankles pulling my legs out straight and spreading them wide, the gleaming white leather of my shoes shone in the harsh light. I struggled lightly against his grip and he tugged firmly on my legs, asserting his dominance and reminding me that he was in complete control here. I had had my moment, now it was him calling the shots and I sighed with satisfaction at the feeling.

"Is this what you wanted? Should I fuck you hard now?" He asked and I nodded my head, my eyes wide and pleading with lust. He reached down and tugged the gag from my mouth and I gasped for air.

"Yes, oh please yes. Fuck me, shove that cock in me. Oh god it feels incredible!" I babbled. My mind was gone, whatever was left of that voice that had told me to fight this was buried in the sheer lust I was feeling right now. This man, this creature had been all I had thought about for the last 24hours and here he was. I had prepared for this, going through endless outfits hoping to please him, I had sucked his cock until he came in my mouth and how he was fucking me. I had begged for this, pleaded like a teenage girl with a rockstar and I was determined to savor every moment.

He drove his cock forward, sliding me across the slick leather of the bench. "Aaaaahhhhhh" I wailed as the head of his prick thrust against the wall of my cunt. He was like a jackhammer, pounding me hard and fast. His hands let go of my ankles and dug into my thighs, pulling me toward him as he shoved his shaft deep into my body.