Jack Part 3

I arrived at Jack's house 15 minutes early, parked in front, and sat waiting in my car for the time to pass. my body odour was noticeable in the confined space of the car, but was overpowered by the heavy fumes rising from between my legs. I looked in the rear view mirror, my hair was matted, dirty, and straggly, unbrushed for 2 days, combined with my heavy makeup it gave me the look of a low rent street whore. Finally it was time, and I got out and walked up to his door and knocked. Jack opened the door, checked his watch and smiled, he was wearing a very expensive grey suit, he bent slightly and kissed my forehead. He led me down the hallway to the living room. We chatted for about 5 minutes, before he announced we should get started. "Have you followed instructions" he asked. I nodded. "Good, take off your dress". I removed it and put it on the sofa, leaving me only in stay up black stockings, and heels. He circled me slowly, taking in my nakedness, inhaling my scent. "This weekend will be a little different Karen, I will be testing your obedience" I nodded, "You are not permitted to speak unless I ask you a direct question. You will address me as Sir anytime you speak, and you will accept all punishments in silence. Is that understood?" I nodded again, already excited. "Hands on your head, and spread your legs shoulder width apart." I did as told, his fingers stroked the short stubble under my arms, it tickled, but I held still, then he sniffed them and smiled. "A slut like you should smell like a slut. Are you a slut Karen?". "Yes Sir" I answered. His fingers slid down my body, between my legs, and 2 fingers rammed deep into my now wet cunt, he moved them around inside me, pulled them back out and held them to his nose, "Yes" he smiled, they were slick, coated with my juices, he wiped them clean on my armpits, and repeated this several times, until my underarms were entirely covered, visibly wet with my cunt juice. "Put your arms down, slut." He pulled a box from under the coffee table, took out and showed me a hand pump, a cylinder about 10" long with a flexible hose attached to the end, and a lever handle, it also had a pressure gauge on top. he took a glass tube, like a small test tube, and attached it to the flexible hose, once again collected some juice from between my legs, and smeared it over my right nipple. then placed the open end of the tube over my nipple, pumping the handle, he pumped slowly, I felt a pleasant sensation, as my nipple was sucked into the tube, the pressure increasing as he continued pumping, soon becoming uncomfortable, then painful as my nipple was sucked deeper into the tube. he checked the gauge, then gave it 2 final pumps, making it almost unbearable. He removed the hose and attached a second tube, repeating the process on my left nipple. I could see both nipples half filling both glass tubes, stretched almost 2". Jack put the pump down and forced 3 fingers roughly into my cunt, I briefly forgot the increasing pressure in my nipples, as his fingers gouged me violently, jerking me around on my heels, It only took a few moments before I was squirting into his cupped palm, he removed his fingers and poured my squirt onto my head, rubbing it into my scraggly hair, then his fingers were back in my cunt, literally digging for more, he was rough, hurting me, and he knew it. I squirted again, and once again he rubbed it into my hair, I could smell it now, strong, a bit pissy. he continued, until after about the 8th time there was no squirt left in me, my cunt felt raw, my hair was dripping, my nipples throbbed. He attached another tube to the pump, knelt in front of me, spread my cuntlips with 2 fingers and placed the tube over my clit, then began pumping, I felt the suction pulling on my clit, already erect and sensitive from the rough fingering, the pressure increasing as it sucked up inside the tube, then the pain starting as it stretched beyond it's limit, and still he pumped, I began to whimper. "Shut up, slut". he hissed at me, giving it a final pump that felt like it might have pulled it off. My thighs were trembling, I didn't dare look down but knew from counting the pumps that my poor clit was being stretched as far as my nipples were. All 3 places were hurting, but I was also experiencing a high state of arousal, as blood rushed to both nipples and clit. Jack turned me around, and pushed me down over the coffee table, resting on my elbows, I heard him unzip his pants, then he spread my cheeks and spat on my arsehole, I screamed as his cock tore my arse open, rising up on my toes, as he drove it balls deep inside me. He grabbed my hair, jerking my head up, then slapped me hard in the face, "Shut up cunt", he yelled in my ear, "Bare it in silence". my face stung, my arse throbbed, full of his massive cock, I gritted my teeth as he fucked it, using it, intentionally hurting me with his cock, his hands found and squeezed my tits, increasing the pain in my nipples, he fucked me hard, grunting as he shot a huge load of hot cum deep inside my arse. He pulled out of me, "Don't you dare fucking move, slut". I heard him walk into the kitchen, open the fridge, then come back, he showed me a glass jar, 3 quarters full, "2 weeks of cum Karen, I wanked 4 times a day into this jar, then froze it, I took it out last night to thaw, but it's still icy cold." I saw him take a plastic funnel from the box, then felt it being pushed deep into my still throbbing arse, then I felt the iciness as he poured the contents of the jar into me. My guts were freezing, it was so cold it physically hurt, he waited until the funnel was empty before removing it, then took the large black buttplug from the box, and forced it roughly into my arse, sealing the freezing cum inside me. He then stood in front of me, " Clean my cock.", I took it into my mouth, sucking and licking the residue from my arse until he was satisfied that it was clean. He pulled me upright by my hair, then reattached the pump to the tube on my right nipple, he pumped it once, almost making me scream, then released the pressure, removing the tube from my nipple, strangely this hurt more. he repeated with the left one, and finally my clit. My blood gorged nipples were more than twice the size they had ever been before, long, thick, puffy, and very pink. Without looking, I knew my clit would be the same, it felt like it had it's own pulse. Despite the overwhelming discomfort in my arse, the painful throbbing, the fullness of the plug and freezing cum, I desperately wanted to be touched, on my nipples, my clit. I knew the slightest touch would produce an explosive orgasm. Jack then went into the room I had slept in on my last visit, before returning with a dress, black, chiffon, spaghetti straps, obviously see through, he folded it carefully, and placed it in a carry bag, then checked his watch. He sat on the sofa, just looking at me, continually checking his watch, several minutes passed, then he picked up the pump again. I realised he had been waiting until he could safely reattach the tubes. he worked quickly, and soon both nipples, and my clit were in agony, as he had added an extra 2 pumps to what he had done before, looking down I saw my nipples had been stretched well over halfway up the tube, at least 2 and a half inches, they, along with my clit, felt like they were being crushed and torn from my body. I had broken out in sweat. Jack placed the pump carefully in the carry bag with the dress. "Time to go Karen", he said as he led me outside and over to his Lexus. I was still naked, as he helped me awkwardly into the passenger seat. He pulled out of his drive and headed into the city. My discomfort increasing, every bump causing stabs of pain. He drove quickly, and efficiently, and 25 minutes later we were parked in Bourke st. He took the pump from the bag, and quickly released the tubes from me, my nipples were huge, throbbing angrily, my clit the same. He reached across me and opened my door, "Get out, and wait for me on the footpath." he ordered. I got out, standing there in only stockings and heels. several people walked past, staring at me, as he took his time getting out and locking the car. he handed me the dress, "Put this on, and stop being such a fucking slut." he said, loud enough for several passers by to hear. My face reddened in pure embarrassment, as I quickly pulled it on. It was very short, showing the tops of my stockings, barely covering my arse cheeks, completely see through, just a diaphanous sheath. my nipples, now huge, clearly visible poking through the sheer material. Jack grabbed my upper arm, squeezing the flesh hard as he dragged me along the street, walking was difficult and I struggled not to stumble, as I tried to keep up. We attracted plenty of attention all along Bourke st. most people turning to stare, then turning into a side street, Jack's pace slowed and he released my arm. We finally arrived at a place called The Winery, a very upmarket restaurant. I was horrified, catching sight of my reflection in the glass door. We entered, and were led to a table that Jack had pre booked, the place was very busy, full of high class patrons, my face bright red, as they openly stared at me. Once seated, he ordered, a salmon dish for himself, a mineral water for me. I was aware of the people at the tables closest to us, wrinkling their noses up in disgust at the way I smelt. ,My shame grew worse, as it became clear Jack was in no hurry to finish his meal. it looked delicious, and I was starving. There were quite a few men ogling my tits, which although causing me to become aroused, also increased the shame I felt. I sat there sipping water until Jack had finished his meal, then he ordered desert. After finishing it, he ordered coffee, he pushed his desert plate across the table to me, " Lick it clean.", I looked around the restaurant, noticed people watching, then obediently bent and began licking his desert residue from the plate, he sat sipping coffee, watching me humiliate myself. He even patted me on the head, like a good dog when i'd finished. Then he called for the check, paid, and it was over. We were standing on the street outside. I felt like crying. Jack noticed, and slapped my face hard, then grabbed my swollen nipple, pinching and twisting it. "Snap out of it slut, the night is just starting." That brought me back to reality, i'd almost cum when he'd twisted my nipple. We walked some more, ending up on Oxford street, well lit, more people, even getting comments as we walked along. "Nice tits", "Look, you can see her cunt.", "What a fucken slut.". things like that. The extra harsh lighting from the shop fronts made me feel completely naked. We'd stopped in front of an adult store, Jack once again grabbed my upper arm and led me inside. The foyer was split into 2 wide staircases, 1 leading up into the store proper, the other leading down into a room filled with video booths. He led me upstairs into the shop, climbing the stairs was very uncomfortable with the plug in my arse. there was a middle aged guy behind the counter, 3 rows of a frame racks containing porn dvd's, one wall covered in vibrators and dildo's, and the far wall lined with glass display cases of leather wear, bondage equipment, whips crops, and canes. There were perhaps 8 men in the store, mainly looking at the dvds, everyone of them turned and began perving on me, including the old guy behind the counter. my nipples still huge, my clit clearly visible, hanging down between my legs, my dress backlit from the lights in the display cases. Jack led me to the bondage section, left me there and went to the counter, returning with the guy. "Can we have a closer look at that carbon fibre cane please." The guy fumbled with a big set of keys, and opened the case, removing it and handing it to Jack, explaining "The handle is moulded hard plastic, dildo shaped, they add sand to the final moulding making it abrasive." he informed, giving me a sleazy wink. I looked around and saw every guy in the shop looking at us, "Can I test it?" Jack asked. The shop guy looked at him, then at me, licking his lips. "Sure, you go ahead and try it." he blabbered. now we definitely had a crowd. Jack leaned close too my ear and whispered, "Not a sound, understand." I nodded slightly, then louder so all could hear, "Take out your right tit, slave." I shuddered, it was the first time he had ever called me slave. I slowly slipped the strap from my right shoulder, and heard mumbling from the men as I pulled my tit out, the nipple still huge and puffy. "Hold it up for me" Jack instructed. I did, and he took aim, then struck it quite hard with the cane, it stung, a bright red stripe appearing instantly across it, seconds later the pain came, a hot burning sensation that grew slowly as the seconds past, Jack struck again, harder this time, I gritted my teeth, my mouth clamped shut, then again, harder still, I moved, but only slightly, got my composure, lifted my tit higher for him. the 3 stripes now burning as one. "Very nice instrument." Jack said, then handed it back to the guy, "Would you like to try it on her?" , the older guy was nodding, but still asking. "Really?" . "Sure, go ahead, give her tit a couple of whacks." Jack answered him. That sleazy old bastard didn't hold back, cracking me hard across the tit 3 times in quick succession. It took all my strength not to collapse in pain. my tit was now heavily striped and on fire. Jack stopped him by saying, "Very nice, we'll take it. Can you wrap it for us." The guy agreed and headed back to the counter. I began to pull my dress up, but Jack stopped me. "Leave it out, I want people to see it. Let's check out these dvd's." his arm around me, pulling up the back of my dress, my plugged arse fully exposed, as we moved amongst the other men in the store, everyone pretending to look at dvd's. Jack occasionally making me bend over to get one off the bottom rack, giving everyone a perfect view of my cunt, and oversized clit. We made our way to the counter, Jack paying for the cane. "Those booths downstairs, do they have gloryholes in them?" he asked, loud enough for all to hear. "yes, they do." the guy answered. "Well you better give me $50, of $2 dollar coins, my slave needs some cock sucking practice." The sleaze laughed and gave him the coins, and we went down to the booth section, there were already several men down in that section, and soon those from upstairs made there way down. Jack selected a middle booth, with vacant booths either side. we went in, and he told me quietly to take every cumshot on my face. The first cock came through the hole almost before we had the door closed, I squatted down and took it into my mouth, "Suck it good slut." Jack ordered, and I did, working it wetly until I felt it swell, I pulled my mouth off it and took 4 hot,thick blasts of cum in the face. "No resting, cocksucker." Jack said grabbing my hair and turning my head, before pushing my mouth onto the cock sticking through the opposite wall. I sucked it in, then felt Jack's hand pushing the back of my head, it was a big cock and he forced me onto it, pushing it down my throat, the guy fucked my throat as cum dripped down my face, I was in heaven, and Jack knew it, when I pulled off he held my head down so cock spurted it's cum all over my hair. Then I was sucking another, and another, and another. my face and hair glazed, covered in thick globs of cum, and still more cocks come through, and still I sucked them. the front of my dress a ruined mess. I stayed in there for over 2 hours, sucking cock after cock without a break. my face thickly coated with spunk, I could no longer see, my eyes being filled multiple times, and I was having trouble breathing through my nose. I felt Jack grab my arms and lift me to my feet, push a tissue into my hand and say, "Wipe your eyes, but nothing else, understand." I nodded and wiped the cum from my eyes. I looked down, my exposed tit was covered, as was my dress. soaking, sticking to my flesh. I looked at Jack, "Are you ready for your walk of shame Karen?" I nodded. "You will keep your head up, your eyes looking straight ahead, until we reach the car. I will be right behind you, and I promise no one will touch you, and you will be completely safe. Understood?" I nodded again. Jack opened the booth door, and I walked out, a small group of men began clapping as I walked up the stairs and onto the street, I wondered if I would see anyone who knew me, then realised I didn't really care if I did. There was still a lot of people about, and I heard many gasps, and a few eeewww's, the occasional slut, and cumdump. I ignored them all and walked straight along the centre of the footpath, head held high, feeling proud, but also completely degraded. The walk back to the car took a little over 20 minutes. The drive back to Jack's was a blur, silent, I sat there like a zombie, feeling the cum drying on my face. my jaw ached, my throat was sore, my arse hurt. We entered the house and I headed for the bathroom, "No." he stopped me, taking me roughly by the arm, dragging me to the cellar door, down the stairs, and into the dungeon. He unwrapped the cane he had bought, "The first thing is to mark your other tit, I like symmetry, Take it out and present it to me, you dirty cunt." I slipped the remaining strap off, and the dress fell halfway off, the only thing stopping it was the dried cum, sticking it to my stomach. I lifted my left tit, holding it high. The cane struck hard and loud, the sting instant, as the burn began it struck again, I whimpered. "Quiet." he yelled at me, and struck again, a hard savage stroke, it felt like my tit had been cut in half, I gritted my teeth, 3 more strokes, and my knees buckled. I was on the floor, holding my tit protectively, tears streaming down my ruined face, as the agony seared into my brain. He walked to a cupboard, took 2 pair of leather cuffs, and threw them at me, making sure he hit me, "Put them on, quickly, and stop being a fucking brat, " I hurriedly attached the cuffs to my wrists and ankles. "Take off your shoes and stand up, straight." I did, my tit throbbing. He quickly stripped the soiled dress off me, then locked my wrist cuffs together, clipping them to the ceiling rope, next, pulling my legs wide apart, he clipped the ankle cuffs to a 4' spreader bar, then pulling the rope until my legs were off the floor, hung by my wrists, he left the room. I hung there in the empty, silent, room. it was the first time I had ever been hung, feeling the pressure increasing on my shoulders with each passing minute, it soon became an effort to breathe, my shoulders began to ache, twisting and squirming made things worse, so I tried to remain still. After what seemed like ages he returned, with the carry bag, and the glass jar that had held his frozen sperm. Placing them on a shelf, he selected a riding crop from his collection, it was short, a wide stiff leather strip, about 4" long, and 2" wide, then a thin shaft that turned into a grip. He showed it to me, then stroked it against my armpits. he stepped back, and smacked it hard into my exposed underarm, I screamed and jerked painfully, then he struck the other side, I had never experienced anything like this, not realising how tender my armpits really were, he worked methodically, with no mercy, despite my screams. each stroke compounding on the other, each causing me to jerk involuntarily, creating more pressure on my already aching shoulders. until, after about 15 hits to each armpit, he finally stopped. I turned my head to see I was heavily bruised. I had forgotten everything else. Jack lowered the rope until my feet rested on the ground, the pressure on my shoulders eased, then he was squatting in front of me, he made a fist, his middle knuckle protruding, then punched me hard on my right inner thigh, that knuckle pushing deep into the tender flesh, then hit the left thigh the same, he repeatedly punched, working his way up and down both thighs, punching that knuckle into every inch of them, he kept it up, until my legs would no longer support me, my weight back on my shoulders, he lowered the rope until I was in a squatting position, I was groaning by now, a constant aching throb in my thighs, Jack collected the jar and squatted behind me, I felt an overriding bolt of pain as he ripped the butt plug from my arse, placing the jar under me, up close, collecting the flood of cum as it poured from my stretched anus, I could hear it splashing into the jar, and feel the wonderful release of pressure, I realised with mixed feelings I was very wet, I felt like my body was betraying me, knowing that the slightest touch on my blood gorged clit would send me over the edge. He must've known, for he reached around my waist and squeezed it between his thumb and forefinger, I exploded, my cunt gushing as it rapidly contracted and released, he deftly captured all of it in the jar, "Yes, you hot bitch, push it out." rolling my swollen clit between his fingers as he squeezed it, pulling it, twisting it, he kept that orgasm going, my first of the night, my thighs despite the beating they had taken, were flexing, thrusting me forward in that squatting position like the hungry cunt I was, and then after what seemed like minutes I collapsed, spent, dangling by my wrists again. He was chuckling behind me, then showing me the jar, 3 quarters full of dirty grey fluid, a mixture of my cunt juice, and his cum, stored in my arsehole for many hours. He put 2 fingers into the jar, stirring it, mixing the juices together, then sniffing his fingers, wrinkling up his nose at the smell before pushing them into my mouth. "Clean them slut". he ordered, the taste was foul, spreading instantly in my mouth, overpowering, making me gag, but I was beyond resistance, and sucked them clean. He placed the jar to the side, and went to the bag, then the cupboard, bringing back the pump, the 3 glass tubes, and the leather hood. he worked quickly, my nipples still very long, having shrunk only minimally, I counted the pumps again, the pain started at 5, he continued to his previous amount of 7, I was crying, sobbing really, he just smiled and added 2 extra pumps, my nipple now almost completely filling the tube. then he did the 2nd one, and finally my clit, that had me screaming and thrashing. He slapped me hard in the face, twice, "Settle down bitch. Ride that fucking pain." he unclipped my wrists from the rope, and each other, and reclipped them behind me to each ankle, then grabbed my hair and dragged me over to a mirror. The reflection looking back at me was horrible, ugly, I looked like a battered a****l. I began crying again, he grabbed my head and jerked it up, "Keep watching." I saw him pick up the jar and pour about 3 quarters of it onto my head and face, he quickly grabbed the hood and pulled it over my head, zipping it tight. the eye and mouth holes zippered shut. My senses were assaulted by the foul fluid covering my face, pressed close by the hood. I was unclipped, and dragged, then lifted, placed on my back, feeling my legs being hoisted high, ankles clipped in place, then my arms stretched above my head, apart, my wrists clipped also. I realised i was on the box like structure, with the 4 upright posts. Being on my back was terrible, the slime settling on my face, breathing only through the nose hole in the hood, being stretched out had also increased the pain in my nipples and clit. I lay there for several minutes absorbing the pain, realising my cunt was wet again, and hating myself for it. I felt a sharp sting in my armpit, the bruised tender flesh being pinched into a fold, then a more powerful bite as an alligator clip was attached to the fold, then another, and another, I kept count in my wet gooey darkness, it stopped after I had counted 12, the pain was sharp, but bearable, then I felt it being repeated on the other side, and though bearable, the pain was increasing with time. My attention returned to my nipples and clit, the pressure was becoming unbearable, I screamed inside the hood as my clit was given another pump, foul slime leaking into my mouth, and then again as the pressure was released and the tube removed from my clit, my head started to spin, I was spluttering, trying uselessly to spit it out, then I felt my cunt stretching as Jack's long thick cock entered me, pushing deep, all the way in, his pubes impacting my huge pumped clit, I was gasping, my cunt gripping at his pulsing shaft, the head ramming my cervix, he kept it deep inside me, his pubic bone grinding on my clit, my orgasm building, then pain as he pumped my left nipple once, more deep thrusting, ramming deep again and holding as he attached the pump to my right nipple and squeezed, I screamed again, more juice finding it's way into my mouth, my senses overloaded, then the pain of release, as he freed both nipples, pumping his cock, fucking me hard, and as my massive contractions started, pinching both nipples, hard, digging his thumbnails into them, maintaining that grip as my orgasm unleashed, releasing them, pinching my clit, twisting it, I thrashed under my restraints, my body bucking, under the hood I was howling, swallowing the fluids finding there way into my mouth, perversely enjoying the taste of it, Jack's cock erupted deep inside me, flooding my cunt with his warm hot cum, it set me off again, thrashing about, his cock stopped pumping jizz into me, but he left it buried deep, as he removed the alligator clips from my underarms. After removing them, he began raking his nails over them, scratching at the ruined skin, as he did this I felt his mouth on my tits, biting, everywhere but the nipples, the pain savage when his teeth bit into the cane welts, my cunt spasmed again, my body twisting and squirming, I felt another orgasm building, deep, heavy, relentlessly rising, then Jack's cock, still imbedded deep inside me, started to piss, hot, stinging, filling me, overfilling me, my cunt sheath flaring around his shaft, his piss pouring out of me, I let out a primal scream under the hood, then began bucking, the orgasm so powerful, it was almost painful, I lost all control, knew I was pissing, my cunt hurting from the massive contractions, it raged on and on, Jack's weight on me, his teeth clamping down hard on my tits, and then I flopped back onto the bench, completely spent. I felt Jack get off me, his cock pull out, then the rim of the jar as he collected what spilled out of me, then he unzipped my eye, and mouth holes, I sucked in air, blinking, slime finding it's way into my eyes, I watched as he stirred the contents of the jar in front of my eyes, "Open wide slut." I just blinked again, he pinched my nipple, digging his thumb nail hard into it, twisting, I screamed, and he poured most of what was in the jar into my open mouth, and quickly zipped the hole shut again. my mouth was full, the vile juice leaking into my throat, I tried hard not to swallow, the hood was snug, making it difficult to open my mouth more than a fraction, and even then, there was nowhere for the fluid to go. Jack was laughing down at me, then his fingers were holding my eyelids open as he poured what was left into my open eyes, before re zipping them closed. my eyes stung, blinking didn't help, making it worse in fact, and in my panic I had swallowed roughly half of what was in my mouth. I thought I was going to vomit, and desperately fought the sensation, knowing I might suffocate. I heard Jack's muffled voice near my ear, "Sleep well cunt. I'll see you in the morning". then I heard the door slam shut. I lay there shocked, crying wasn't an option, it would only make things worse, after what seemed like an hour, I realised he wasn't coming back, I decided to swallow what was left in my mouth, but slowly, a little at a time, so I wouldn't gag, I don't know how long it took, but eventually my mouth was empty, though the taste lingered. I don't know how, but at some stage I must have fallen asleep.
I was jolted awake by the sting off a whip cracking across my belly, followed by several more, before being unclipped, stood up and moved, then my wrists raised and again clipped to the rope, my ankles clipped together, and being pulled upwards off my feet, my shoulders screaming in pain. the whip cracked again, this time across my shoulders, then lower across the small of my back, and again stinging my arse cheeks, I swung helplessly as it struck, time and again, my flesh crawling, as I was whipped front and back, so many strikes, until 1 struck both tits, and my left nipple, I passed out.