Slave to the Man

Part 2: Personal Assistant

I stood there for a few moments, eyes searching the room for my clothes.

"Don't worry. You'll get them back." said Jim "Once I've finished with you."

He must have seen the glimpse of resentment and confusion in my eyes. Hadn't I just got on my knees and sucked his cock? Hadn't I repaid the debt? Couldn't I just go now?

"Oh you thought that I'd already finished with you, huh?" Jim laughed, echoing my thoughts. "Ha! I've only just started! Besides which, with the amount you owe me, that blowjob would make you the most expensive cocksucker I've ever rented, and I've rented a few in my time. Particularly considering you were hardly expert at it! No, you can sit down there on the end of the bed until I've decided how else you need punishing. Oh and drop that towel."

I reluctantly did as I was told, the towel hitting the floor as I sat down. I didn't bother trying to hide myself this time, just leaning back on my hands, my thighs open, cock drooling some late juices at it lay across my thigh. After being seen my Jim as I just had, simply being naked in front of him no longer held any shame, any more than if I'd been sitting in a sauna or getting changed at the gym.

Jim ignored me for about five minutes as he drank his scotch and finished off the cigar, leafing through some paperwork on his desk. Then getting up he walked across to the bedside table and picked up the remote to the TV. The large flat screen flickered on and he immediately selected the adult content and started scrolling through the selection available. A gallery of DVD covers featuring women with varying sized tits slid across the screen, with titles like Bad Girl's Dorm and Girls that Love It!, after a while I looked away, trying to spot where Jim might have put my clothes.

"Ah, now this will do." said Jim with some relish, as he made his selection. It seemed to be called Bottoms Up! and featured a clothed and seated, silver bearded, older man, his hand raised in the air, seemingly in the process of spanking the pair of smooth buttocks of a figure bent over his lap, whose head and shoulders were out of the frame.

"Yes, this seems most appropriate." Jim smirked.

I felt a quiver of fear run through me, realizing what the next part of my punishment would entail, but also slight relief. I wasn't ready to face sucking on his cock again just yet, and considering how Jim could have punished me, I guess I had to think myself lucky. After all, it was a more... conventional form of punishment.

Jim threw the remote down on the end of the bed and then sat heavily at the head end in the center, his back resting against a pillow. He loosened the front of his robe and pulled it open, then patted his thigh just by his cock, which like mine was lying almost flaccid there, the tip resting in a small drip of juices.

"Come here then. You know what you've got to do."

I stood up and walked around to the side of the bed, before getting on all fours and crawling across to him. As I neared him he reached forward and grabbed me by my hips, hauling me across his lap so that I felt his cock against my belly, and my own hung down to rest against the outside of his thigh. My cheek and palms rested on the mattress, my head turned to the side, watching the TV screen as the film opened and the credits appeared.

Jim's hand ran firmly up the inside of my thigh, his fingertips brushing against my balls, before moving over my ass. He hand roamed, squeezing and groping each cheek in turn, and then he paused, palm resting on one as he spoke to me.

"Now I'd be surprised if you hadn't had at least one spanking in your life before, so I'm presuming you know what to expect. Don't worry, I'm not going to torture you, just redden those ass cheeks enough for it to sting and for you to know that you're being punished, and for it to make you think about what you've done. I'm not going to stop until I think that you've learned your lesson. Ready?"

I nodded meekly.

He brought his hand down on my right cheek first. I felt the flesh quiver and the sharp sting of contact, making me draw in my breath sharply. Another, this time on the left, then back to the right. He alternated between them, the blows landing about every couple of seconds. I could feel his cock getting progressively, almost imperceptibly harder beneath me, and as my ass cheeks started to warm and smart, the strokes became more punishing, until finally I whimpered each time a blow landed and my hips involuntarily bucked slightly. After another five strokes or so, I gave a small cry, my hands trying to move to cover my ass from his hand. Immediately my wrists were clamped in a vice-like grip of one hand, and he held them there, pinned firmly to the small of my back, as he continued my spanking, freely laying on the strokes on either and then both buttocks together, and I whimpered, cried and moaned, tears welling up in my eyes as my ass smarted and my shame mounted, and my hips bucked and rocked, my back arching, which only made my ass push out even more and present itself as a better target.

All the while the noises in the room were being echoed by the film on the TV. I could hear the steady slap of skin on skin, interspersed by a whimpering moan. My eyes flickered open as I realized that although the moans I could hear sounded quite feminine, they seemed actually to be coming from a male. Sure enough, on the screen was the same older guy from the DVD cover, but it appeared the ass over his knee belonged to a younger man, perhaps in his 20s, who like me was receiving a thorough ass warming, his cheeks red, his hands pinned by the wrists behind his back.

I let my eyes drift close again and tried to control myself as the blows continued to rain down. Just as I thought I was going to cry out and start begging Jim for mercy, Jim stopped. I felt him lean to the side of the bed to retrieve something from the bedside drawer as I lay there, my ass stinging and hot. There was a small pause, during which time I opened my eyes slightly and saw on the screen that the spanking there had ended too, and the older guy was sitting back with a pleased expression on his face, with the younger guy on all fours, his red ass to the camera, his head bobbing up and down on the old guy's cock. I hoped that Jim wasn't going to make me suck his cock again.

Actually the next sensation was rather pleasant as Jim squeezed a large amount of what felt like a cool cream or lotion onto my stinging, reddened cheeks. I practically moaned with the soothing sensation it gave me. I heard a top being snapped back on a bottle or tube and then both his hands started to rub and knead the lotion into my cheeks, being almost delicate and caring in the application, as though he genuinely wanted me to be soothed. His hands gently squeezed and rubbed, massaging my soft cheeks. Occasionally his fingertips brushed incredibly close to my anus, which I thought it was unintentional, that is until a finger started tracing a circular pattern on it, gently massaging a blob of cream into the puckered flesh of my opening.

For a moment I didn't move, not certain that I was feeling what was actually happening, and then the tip of the finger wriggled against and then pushed past my tight opening. I immediately tried to rise off his lap, simply shaking my head and saying one word: "No". But Jim immediately clamped his arm down fast on my hips and started spanking me again, hard. This time I couldn't help but cry out, pleading with him to stop.

"Well you've got a choice Jamie," he said, pausing for an moment. "Either let me do what I want or I'll get a belt and thrash you until you won't be able to sit down at the conference tomorrow. And then I'll do it anyway."

There was some more pitiful begging, some more hard spanks, and then I was broken, lying there submissively as both hands returned to my ass, but this time not being slow or surreptitious, and certainly not being gentle and caring, roughly gripping and splaying my buttocks as I felt a spatter of spittle being drooled between them. The finger return, rubbing the saliva mixed with lotion all around my opening, before quickly and forcefully being pushed inside. I whimpered as the digit was pushed up to the knuckle before being extracted, rubbed around my hole, and then pushed back in again. This happened four or five times and then it was joined by another, and the process repeated, each time another finger being added, the only pause being for more lubricant, either from lotion or saliva.

I'd experienced a finger in my ass before, both medically, experimentally during masturbation and from an enthusiastic and sexually liberated ex-girlfriend, but nothing like this, and never by more than one digit. Not even a thumb. There wasn't a great amount of discomfort due to the liberal applications of lubricant, but these sensations were unfamiliar, uncomfortable and humiliating, which I supposed was the reasons for Jim doing it.

As what felt like four fingers were inserted I let out a long whimpering moan and bit down on the mattress. My eyes flickered open and I saw on the screen the young man suffering a similar indignity to me, except he was still on all fours with the older guy crouched next to him, pulling apart his cheeks for the camera and licking and fingering his hole. Jim seemed to be inspired by this and the fingers were removed and once again my cheeks were spread wide by two strong hands. He managed to dip his face to my rear and I felt his hot, wet tongue squirm and probe at me as I moaned and whimpered, trying to escape the fact that it actually felt surprisingly good, and that my cock was thickening against Jim's thigh. I could feel his own cock starting to press hard against my belly and wondered how long it would be before he was pushing my mouth down onto it once again, although somehow I didn't mind the thought of it quite so much now.

The tongue pushed at my opening with a steady rhythm, and then his fingers were once again inside me, the four digits entering me much more easily this time, pushing quickly up to the knuckle. This time they weren't removed, just pulled out a couple of inches, before being pushed home again... and again... and again.

The speed and force of this manual rape of my anus increased, the fingers now easily penetrating and widening me, his knuckles banging against me each time he buried his fingers to the hilt. His other hand had a firm grip on one of my ass cheeks, pulling it to one side to allow him better access.

"Arch your back. Push that ass out" Jim commanded breathlessly.

I did as I was told and he groaned slightly with obvious pleasure.

"Fuck that's a great ass. You've almost got a girl's ass... fucking hot." S

trangely I was flattered. I'd had girls compliment me on my ass before, but I'd never felt as though it was the object of unbridled lust. I felt that now as Jim lost himself in it... tonguing me, fingering me, spanking the cheeks, groaning as he lusted and examined every inch of my rear, and all the while my cock thickened and pressed up against his thigh, almost painfully.

I could hear steady rhythmic slapping and groans and moans from the TV and knew before I'd even opened by eyes what I was going to see. Sure enough, the younger man was still on all fours, but the older man was crouched above him, gripping his shoulders and pistoning his cock wildly. The scene switched to a close-up of the thick member sliding in and out. The hole it fucked was stretched wide, the young man's limp cock and balls swinging back and forth as the older guy fucked him, the latter's own nuts squeezing and slapping up against the lad's butt.

Suddenly Jim was pushing me back off his lap, manhandling me, keeping me face down, and then his weight was on top of me, his hands pushing down on my shoulders to keep me still and his knees forcing my legs apart. Jim was going to fuck me, and I realized that after his tongue and his fingers, and the eventual pleasure that they'd brought, that I almost wanted him to. But my pride and shame conflicted with me and I struggled against him, looking back over my shoulder to make pathetic whimpered pleas for him to stop.

Jim didn't reply, but just moved a hand to my neck and rammed my face into the mattress, gripping my wrists and pinning them either side of my head. His knees had spread my thighs wide and I immediately felt the heat and then pressure of his swollen cockhead as it slithered and pushed its way between my buttocks, searching for entry. My hole had already been well and truly loosened and lubricated by his previous attentions, and as soon as the tip was seated against me he pushed the entire length inside me in one long, slow thrust until it dug uncomfortably in my innards, and I felt his pubic hair tickle against the stretched flesh surrounding his substantial girth.

I let out an agonized cry and whimpered that it was too deep, but Jim just held it there, gyrating his hips and grinding his cock inside me, his whole weight pressed on me. His lips were by my ear, his breathing heavy and ragged with lust.

"You'll get used to it, faggot." he growled into my ear.

Then pushing himself up again, he gripped my wrists tight and started to fuck me, starting slow by pulling his cock almost out, with just the cockhead remaining inside, before sliding it back in again, but in no time at all the tempo had risen to the point that he was pounding away at me, his hips thudding against my ass cheeks, making them shake.

His cock felt immense inside me. My hole had been relaxed enough beforehand to take him without tearing me apart, but it still felt as though it was being stretched to the limit, and his cock just seemed to fill my insides. I was gasping with each thrust, my head spinning as I hyperventilated. All the while, over and over in my head, I just kept thinking "Oh my god, I'm being fucked in the ass. I'm being raped."

Keeping his cock inside me, he moved his knees to outside of my thighs, clamping them together. Then he released my wrists and slid his hands down my body until he reached my waist, which he gripped each side like a vice and continued to fuck me mercilessly.

Eventually he stood up on the bed and placed his feet either side of me, hauling my hips upwards until I was on my knees, with my forearms and face still flat against the mattress so that my ass was high in the air, and then reached down to place his hands on my ass cheeks, spreading them wide with his weight as he dipped his cock back into me, crouching over me and pumping his hips and cock, his balls swinging forward with each thrust to slap against me. "

"Yeah... that's it... you feel that bitch?" Jim asked breathlessly "That's what a real man's dick feels like. How does it feel to be a real man's sissy huh?"

He paused long enough to grip my shoulders and haul me into a position on all fours, never taking his cock from me, and then lazily continued to fuck me, one hand resting on the small of my back, the other occasionally slapping at whichever of my ass cheeks took his fancy.

I gasped and groaned, whimpered and moaned, my whole being dominated by the cock invading me. Like the lad in the DVD, my own cock swung about between my thighs and up against my belly as each thrust was pumped home, and I could feel it spattering them with the precum that was evidently oozing from the tip.

I was only semi-erect despite this reluctant arousal, as though my cock knew it wasn't going to see any use, but the sensation of my cockhead slapping against me, combined with Jim's relentless pounding against what must have been my prostate gland, started to build a familiar orgasmic sensation within me. The sensation built and built in pressure, each thrust from Jim and each inadvertent slap of my cockhead against me bringing me closer and closer to the point of no return. I'd never felt an orgasm build up like it before, and when I finally came the climax washed over me in huge waves.

"Ohhhhh fuuuuck... yesssssssss" was all I could manage in a falsetto, almost feminine whimper as my poor semi-limp cock twitched and drooled a stream of cum onto the bed beneath me, my anus twitching with each pulse of pleasure that coursed through me. This was Jim's signal for a last frantic hammering against me before blissfully gasping as his cock twitched and spasmed, his balls no doubt tight as they emptied their load deep inside me.

My arms collapsed under me, my face hitting the mattress as I lay there gasping, the aftershocks of my massive orgasm flickering through me as Jim slowed his thrusts, giving one last deep thrust before finally stopping, pausing for a while as his breathing slowed and I felt his cock begin to start losing its erection. I felt beads of his sweat drip onto my back, as he took a deep satisfied breath and then pulled his cock from me.

As he withdrew I whimpered again at the gut-lurching sensation, and then felt the warm flow of his semen following his cock out of my ravaged hole and oozing down my balls and inner thigh. He gripped my ass cheeks and spread them wide, evidently watching as my anus twitched again and squeezed out more of his hot seed.

"Fuck, look at that." he murmured. "I've fucked your asshole so wide it looks like some whore's pussy. Still," he remarked, giving my ass a last slap before climbing off the bed "I guess that's what you are now: a whore. Selling your ass to pay your debts. Fuck, I'd rather take my chances in prison than just agree to a buggering, but you... fuck, boy... you didn't even put up much of a fight, did you?"

I just lay there, small pinpricks of light across my closed lids as my own breathing began to slow somewhat.

"Fucking sissy. You know your place is taking a real man's dick don't you, faggot? Well that cum dripping out of you marks you as my bitch now, and I'm going to be turning that ass into a pussy whenever the fuck I feel like it. My very own personal assistant for the week!" he laughed cruelly. "I tell you boy, I'm going to be needing a lot of assistance."

I just lay there as he sauntered off to the bathroom, my ass still high in the air, gasping for breath, barely aware of anything except the empty feeling inside me now that Jim's cock was gone, and the occasional warm trickle of sperm seeping out of me.

Jim's words were no doubt meant to humiliate me further, but after having my mouth and ass raped, there seemed really no greater thing Jim could do to show my submission and his dominance. He had forced me to submit in the ultimate way that one guy can to another, and to be honest most of what he said was true anyway. I had whored myself, and I hadn't really put up any sort of resistance to the rape I'd been subjected to. And the orgasm. God, I'd never felt anything like it. I'd loved it. Maybe I was a faggot? Maybe Jim was right and my sexual place was with a cock in my ass? My knees finally gave out and I collapsed onto the bed into the small puddle of my own cum, my breathing slowly coming back under control but my eyes still seeing tiny stars. All my energy seemed to be drained out of me. I was still laying there when Jim emerged after taking a shower. He ignored me and continued drying himself off.

I slowly stood and then walked tentatively to the bathroom, once again stepping into the shower and letting the water wash over me and hopefully take some of my shame with it. I reached down behind me and touched myself with a trembling hand. My hole still felt stretched and loose, and I whimpered slightly as I stood with my back to the shower and pulled my cheeks apart, letting the water splash down between them, as I forced what I hoped was the last of Jim's ejaculation from inside me, grateful that at least it was a second, lesser load, and that the immense one over my face hadn't been the one injected deep inside me.