A Slave to Pleasure Pt. 04

I steeled myself--afraid or not, I had opened Pandora's Box. There was no going back, and this man had plenty of ammunition to ruin my life if I tried to blow him off. I thought back to the surveillance video he'd shown me three days before during our first session, a video of me being forced to suck dick in my driveway. He had footage of my every misdeed and he had plainly told me that he would involve my parents out of "neighborly concern" if I ever attempted to disobey him. I had to choice but to pick up my phone and unsteadily navigate to the text thread with Mr. Robertson's protected number:

Private, 8:27am: Headed out to pick up your gifts now. See you at 10. If I'm not home by the time you get there, let yourself in--the door's open.

Private, 8:27am: Don't forget the cucumber.

As per usual, Mr. Robertson's texts made it clear that he was monitoring my activities in my own home. I nervously glanced around for what felt like the hundredth time in the last three days: while I was horny, I found the surveillance to be incredibly kinky, but when my head was clear, the knowledge that my master was always watching was starting to gnaw at my psyche. I looked down at my omelette, suddenly disgusted by the food before me. A sudden flush of heat hit my face as anger rose in my belly. I wanted to cook for once, and he can't even leave me alone to enjoy it. "Fucker," I said aloud, sharper than I had intended. I waited tensely for several minutes, anticipating a scolding or promise of punishment to flash onto my phone's screen, but it never came. Emboldened by the fact that my master hadn't responded to my outburst via text, I picked up the worn ceramic dish that held what should have been my breakfast. I stormed into the kitchen and threw the omelette and its plate into our metal garbage can; the ceramic dish shattered on impact with a satisfying, splintery sound. Destroying the plate was immature, even for me, but the lack of control over my own life was really starting to bother me. I'd just wanted a fucking omelette, but he couldn't even let me have that. Instead, I thought, I get to eat my dildo cucumber.

I pivoted to the fringe and retrieved the vegetable, slamming the fridge door with enough force to rattle the bottles and jars inside. I chopped it up roughly and brought it back to the dining table, not even bothering to transfer the cucumber from the cutting board to a plate. I picked up a slice and contemplated it closely; I'd washed it thoroughly, but the knowledge that it had been inside me was humiliating to say the least. What kind of whore fucks themselves with a cucumber--that's fucking humiliating. Mr. Robertson had told me to do it, but when I was horny, I submitted so willingly to his perverted whims. I'd double penetrated myself with zero hesitation, on camera, just because an old man told me to do it. And now, that same old man was going to watch me eat the cucumber that I'd desperately used to quell my lust just a few hours before. I popped the cucumber into my mouth, chewed hesitantly, and swallowed. It didn't taste off or funny, but a blush rose to my face at the shame and depravity of the situation. What was this man doing to me?

As I worked my way through slice after slice, my anxiety slowly melted away and I let myself regress into the uncomplicated, submissive headspace that I usually reserved for my in-person sessions with my master. As logic gave way to my primal urges, I felt my nipples stiffen against the pink cotton of my pajama top. My knees clenched together as a spasm of arousal shot through my belly, and I felt a wetness forming between my legs. He wants me to be a slut, I though, so I might as well try to enjoy it.

I mindlessly ate the entire cucumber, and by the time I was done, it was almost time for me to report to Mr. Robertson's house to receive my "toys." I'd never owned a sex toy before, and I had no idea what to expect from this morning's session. I cleaned up the dining table and made my way to my room to freshen up. I doubted that I would stay clothed for long, so I didn't even bother with underwear. I gingerly pulled on a pair of running shorts, trying to avoid the worst of my welts and bruises, and threw on Mr. Robertson's oversized t-shirt, which still lay puddled on my bathroom floor. This time, I did bring my phone with me as I walked out the front door into the brisk morning light. 9:58, I thought. If he wants me to be in time, I'll be exactly fucking on time.

Mr. Robertson's grey Audi was nowhere to be seen, but I remembered his instructions and the consequences of not obeying my master. I walked to the front door and watched the final minute tick past on my phone's clock. It was exactly 10:00am when I turned the doorknob and gingerly stepped through the front door unaccompanied for the first time. Despite our sexual exploits, it felt strangely intimate to let myself into my master's house. I felt awkward, like a kid in an art museum, and I knew that Mr. Robertson was probably watching me. If he had cameras in my house, I'm sure his house had an even more robust security system. I walked to the familiar leather chaise lounge where my master had claimed my virginity and sat down demurely, crossing my legs and sitting politely in anticipation of Mr. Robertson's arrival. It was a matter of minutes before I saw the grey shadow of the old man's car pull up into the driveway.

My master walked in the door and smirked at me perched obediently on the sofa. He was back in his usual retiree getup: a large, loud Hawaiian shirt, khaki shorts, and a pair of flip-flops. The suit Mr. Robertson had worn the day before stood out from his usual casual attire, but it was reassuring to see him back to normal. In his hand was a sleek, unmarked black shopping bag. He set the bag down on the chair across from me, then sat down heavily next to me.

"I could get used to this, coming home to you waiting on my couch. I would've preferred that you were naked."

I kept my tone even and playful as I replied: "I wasn't sure what the dress code was, sir. You were dressed so nicely yesterday."

He smirked crookedly at me, dark eyes twinkling with amusement. "Yes, I had a meeting earlier in the day. I'm still on the board of directors at my brother's tech company. It was a happy accident that I had a tie on."

The old man's massive hand moved casually to my thigh, encompassing almost my entire leg as he stroked the smooth skin of my inner thigh. His eyes roved shamelessly over my body as he spoke again:

"I appreciate your promptness today, my dear. I will admit, as happy as I am to see you again so soon, you're here because I have to punish you. You are the most insatiable little slut I've ever worked with--did I not satisfy you enough by taking your pussy and your ass yesterday? You went home and read porn without my permission, and as much as I love watching you skewer yourself like a little whore, I cannot abide by your continued pushing of boundaries. You just can't seem to keep your hands off that greedy little cunt. If you want cum so badly, I'll make sure you have the proper tools for it."

The old man got up and retrieved the black bag, gesturing for me to follow him to the bedroom. He deposited the bag onto the bed before turning to me abruptly, looking up and down my body with an unspoken command for me to strip. I pulled the shirt off without hesitation, letting my heavy breasts bounce as they slipped free from the fabric of my master's shirt. I dropped the shirt and winced as I tried to pull my shorts down; taking them off was proving more painful than putting them on.

"Turn around," the old man instructed me, "I want to see the marks on your ass."

I turned around and continued to pull the shorts down, stretching the waistband as wide as possible to keep pressure off of the welts and bruises that peppered my ass and upper thighs. I'd popped a few more ibuprofen before breakfast, but the pain of the beating was really starting to set in, and I gasped as the fabric brushed against a welt on my inner thigh. I heard Mr. Robertson grumble with satisfaction at my whimper of pain, and as I turned back around, I could see the bold outline of his erection pressing against the khaki of his shorts. This motherfucker is getting off on watching me struggle. He likes it when I'm incapacitated with pain.

Already deep in my sub space, the sight of my master's hard cock concealed within his pants made my knees clench together with arousal and anticipation. I stood completely bare at the foot of his bed while my nipples stiffened under his hungry gaze. He grabbed the bag, dumped its tissue-wrapped contents onto the bed, and unwrapped three objects, never once removing his eyes from my body. I, however, stared openly as he revealed my new toys: a thick, textured pink dildo, a small, slim black butt plug, and a large white body wand with a long cord that plugged directly into the wall.

"Have you ever used any of these before outside of this house?"

I had only ever seen sex toys at the seedy stores in the mall, where Kelli would tease me and point them out while describing their uses to make me blush. It had always made me horny, standing there while she told me about how good it felt to use a vibrator. After our I struggled to keep my mind on my master's words as images of Kelli swirled through my head.

"No, Daddy. I've never used any sex toys, except for over here with you."

"Good. These are yours now, but I think I'd better show you how to use them first." He stood, leaving the toys on the bed as his hands moved to my body. The old man's fingers trailed up my abdomen, grazing lightly over my nipples before winding their way around my throat. He squeezed lightly, but hard enough to show me the power behind his grip--if he wanted to, he could choke me into unconsciousness without a second though. My master must have seen a glimmer of fear in my eye and smirked as he squeezed tighter, bringing his face down to look directly into my eyes:

"You're smart to be afraid. Maybe you'll remember this fear the next time you want to fondle yourself like a slut."

One of his hands suddenly released my throat and shot down to my nipple, pinching and twisting with a severity that made me shriek out in pain. The old man's other hand, still on my throat, latched down with equal fervor at my outburst. He maintained the pressure on both my neck and my nipple, but after a few seconds, I didn't even notice the pain on my breast; my vision spotted and I reflexively began to struggle against the old man's iron grip, but to no avail. After what felt like an eternity (but was probably only a few seconds), air flooded back into my lungs and I gasped at the euphoric head rush that came along with the flood of oxygen. Mr. Robertson released me abruptly, letting me fall to my knees on the floor as he turned towards his closet. I ignored his retreat and attempted to control my frantic breathing. I put my hands on the carpet in front of me, panting on all fours--the fall to my knees had put pressure on my ass, and while all fours was...undignified, it alleviated the pressure on my sore, throbbing backside while I tried to catch my breath.

Just as I managed to even out my ragged breathing, Mr. Robertson's feet stepped into my view. I leaned back, getting to my knees with a wince of pain; he wanted to see me hurting, so I intended to make it difficult to get another reaction out of me. I looked up to meet his gaze, trying not to let my eyes snag on his hands, which held a wicked-looking pair of clamps connected by a slim metal chain. He ordered me to stand and I obliged, leaning heavily on the bed to alleviate some of the pain from my bruises. I stood, slightly unsteadily before him and once again met his gaze. Mr. Robertson's stare simmered down on me with something that looked like admiration, then his eyed dipped to my breasts.

"I'm going to clamp your nipples. This will keep them hard, and it will hurt worse than those clothes pins."

I nod, keeping my eyes fixed on his as his fingers moved up to fondle my right nipple. When it hardened under his touch, I felt the silicone-tipped prongs of the clamp close slowly around the hard bud at the tip of my breast. My mouth opened to gasp at the pressure and pain, but I held my tongue, forcing my mouth closed as I stared unrelenting at Mr. Robertson's eyes. He smirked wickedly and released his grip on the first clamp, allowing the weight of the chain to tug my nipple gently downward. I swallowed and gripped my hands hard at my sides--the sensation was an intense combination of pleasure and pain, my nipple erect and throbbing under the firm pinch of the clamp. The old man's fingers found my other nipple, teasing it out before closing the matching clamp around the sensitive bud. He released it slowly, allowing the weight of the chain to settle on my tortured nipples, and I couldn't contain the fluttery moan that escaped from my lips. My master grinned openly at my reaction as his hand tugged gently at the chain; the sudden pressure tipped my breasts with a pain that melted into pleasure as my nipples stiffened even more against the added weight.

"Lets get you on the bed, my dear. Get up there and lay on your back." Mr. Robertson grabbed a metal bar that I hadn't noticed before--I assumed he retrieved it from that mysterious closet while I was kneeling on the floor, half-choked. He broke out a bunch of tools today, I though, how much kinky shit does this guy have stashed away in that closet?

I hesitated before climbing onto the bed: "My... um, my ass..." It was going to hurt to lay on my back, but that I could deal with, just to spite him. He clearly hadn't forgotten how much pain his beating was causing me throughout this entire session, but I was determined to beat him at his game. When in doubt, break out the good manners: "I don't want to bleed on your duvet."

The old man chuckled at me, but turned wordlessly to get a towel from the bathroom. He placed the towel, then turned to peer down at me with that same infuriating look of bemusement.

"Anything else I can get you?"

I shook my head and climbed gingerly onto the bed, positioning the worst of my welts so that they were well within the boundaries of the towel. I gritted my teeth and lowered myself slowly onto the bed. The pain of laying on my back was bad, but bearable just to see the look of appreciation that crossed Mr. Robertson's face as I stretched my hands above my head. The motion pulled my breasts upwards slightly, tugging at the chain and reminding me of the firm pressure on my nipples. The clamps kept them half-hard at all times, but if I was focused on other pain, I could almost forget about them--when my nipples hardened fully, though, the pressure of the clamps was enough to make me tremble.

Mr. Robertson reached above my head and produced one of the straps from his bed frame. As the old man secured the cuff snugly around my wrist, I tugged gently to test my bonds. Just as they had been before, the straps held me firmly in place. No getting away now.

"Now I'm going to put these cuffs on your ankles. They clip into this bar, you see, and it will keep your legs apart for me while we work, but I can still move you around a bit."

Goosebumps raised on my skin at his words, and he rubbed them admiringly as he slid the cuffs around my ankles. The metal bar clipped into the cuffs, and then the old man extended the bar, roughly shoving my feet even wider apart. I heard the bar click into place, and suddenly I was completely immobilized. The bar kept my legs spread wide no matter how I twisted my hips or knees, and given how much the hand restraints already limited my range of motion, I could do nothing but lay flat on the bed as my ass and nipples throbbed with pain.

"Now isn't that a pretty sight? Let's fill those holes of yours, little one." My master retrieved the butt plug, trailing it up my body slowly before he pressed it into my mouth. "The more you lube it up, the less it will hurt going in, my dear."

I sucked on the plug, rolling the smooth, soft silicone around on my tongue. The old man chuckled again at my feigned enthusiasm, slowly withdrawing the plug from my mouth and moving downwards. I felt the toy dip into my pussy, which was absolutely soaked--I hadn't realized how wet I'd become as my master strapped me to his bed. Then, suddenly, the toy was prodding at the entrance to my rear. The tip slid slowly in and out as Mr. Robertson patiently stretched the tight ring of my ass. After a few moments of teasing, the old man applied a steady, relentless pressure. When the widest part of the plug entered me, the tightness of my hole sucked the tapered toy snugly into place, lodging it deep inside of me. I groaned as my ass spasmed pleasantly around the plug: the shape of the plug fit perfectly, providing just the right amount of pressure without overwhelming my inexperienced hole. Mr. Robertson stroked between my legs, his fingers lingering over the flared base of the plug and pushing it slightly deeper into me. I moaned again at his touch, unconsciously bucking my hips into the gentle thrusting of the toy in my ass.

"Starting to enjoy anal, are you? I'm surprised--most women take some persuading, and even the best anal slaves usually take some time to get used to the sensation. Looks like you're a natural... or maybe just a fucking slut. I'll be filling your ass with cum in no time, little one. Now let's get that pussy taken care of--you're absolutely soaked."

Mr. Robertson climbed onto the mattress, moving over me to straddle my body just above the knees. The old man's eyes raked over my body: my hands, which I'm sure were reddening from the pressure of the cuffs; my face, probably also red from exertion, contorted in an a mix of ecstasy and pain; my heaving, clamped tits, soaked in a sheen of sweat; the base of the anal plug pulsing gently in my tight hole. He put a hand possessively over my soaked sex, stroking my clit with his thumb in slow, tantalizing circles. I shuddered under his caress: he could be so gentle when he wanted to be, teasing the most sensitive areas of my body with expert precision and control. The dildo entered me with agonizing slowness as he maintained the steady rhythm of strokes on my engorged clit. The combination of sensations was enough to have me moaning and squirming beneath him as the dildo continued its unrelenting advance. Finally, the toy bottomed out inside of me, and Mr. Robertson released it and moved his hand up to the chain that connected my nipple clamps. He tugged the chain firmly upward, sending a wave of stimulation through my nipples and into my core, causing my pussy and ass to pulse and clench around the toys lodged inside me. He knows how to hurt me, but holy fuck, he makes me feel so good, too.

I closed my eyes, focusing every bit of my concentration on controlling the spasms of pleasure that rolled through my core. I was desperate to cum, but I knew the old man would be furious if I took my pleasure without permission right in front of him. I was so focused on the endeavor that I barely registered as Mr. Robertson dismounted me and climbed from the bed.

"Do you like that, you fucking whore? You enjoying having your tight little holes filled?," the old man reproached.

"Yes" I sighed, replying automatically with my eyes still closed. My body clenched around the toys again, harder this time, and a moan escaped my lips as I willed myself not to orgasm right then and there.

"Have you forgotten? You're here to be punished."

Out of nowhere, a dozen individual points of blinding pain erupted across the top of my right breast. My eyes flew open as I cried out in surprise and torment. Holy shit, that wasn't a crop or a belt. In my master's hands was another new toy: a whip-like object crowned with a cluster of knotted leather strips. My eyes widened as the old man cocked back his arm and brought the cords down across my left breast: the cruel leather slashed across my chest, my areola, and even my clamped nipple. I arched my back and screamed in earnest this time, thrashing hard against my bound hands as tears streamed down my cheeks.