15 comments/ 129157 views/ 152 favorites Annie Rides the Sybian Ch. 01 By: Goldeniangel A big thank you to LoAnnie for the story idea! I named the main character after her in honor of getting the story suggestion from her... any other similarities are pure coincidence. This chapter is in the Toys/Masturbation category, following chapters will be in the Non-Consent category, although the vast majority of them will include use of the Sybian. Enjoy! The summer after my first year at college, I did something remarkably stupid. I have my excuses. I was eighteen years old, still just a kid, what did I know? Not much. My first time was with a guy that I'd only been on a couple of dates with during my third semester. He was hot and I was tired of being the only virgin I knew. It was okay. But I knew it could be better. I read a lot of dirty stories online and that's pretty much what my Kindle was devoted to. And I don't mean 'erotic romances,' I mean down and dark dirty, perverted, kinky nasty shit. I had started off innocently enough, reading the romantic stuff and the erotic stuff, and then I'd somehow swiftly devolved into all sorts of darker fantasies - forced seduction, ropes, whips, anal, and the big one: the Sybian. Now, if I'd been almost anyone else, maybe the Sybian wouldn't have been my biggest fantasy. But see, my parents have this neighbor, Marcus Chase, and I would always house sit for him whenever he had to go away on business. Mark was a decently nice guy who gave off a slightly creepy vibe - any time a guy in his forties is blatantly checking out a woman more than two decades younger then him it's kind of creepy - and he happened to have a room in his basement that I wasn't allowed into. After my eighteenth birthday he upped his creepy factor by telling me why. He had a Sybian down there. When he told me, he said it in that way that indicated he thought it was a BIG DEAL. At the time, I had no idea what it was but I didn't want to look like an idiot and so I just nodded my head. When I got home, curiosity got the better of me and I looked it up - enter a whole new vault of stories and fantasies for my fucked up little head. Sex had been okay, but after reading the stories, I was dying to ride a Sybian. A fucking machine that wouldn't stop? Yeah, that sounded pretty awesome. Even hotter if I was tied to it and forced to ride until I passed out from orgasms. I told you the stuff I was reading was getting kinda dark. If Mark had been slightly younger, more attractive, and a lot less creepy, I would have tried to ride his. He started hinting around that he would love to watch me ride. But the creep factor was just waaaaaay too high. The idea of him watching gave me the ickies all over - and while some of them turned me on just a tiny bit in that 'forced fantasy' kind of way, I definitely wasn't going to choose to ride it in front of him. But man did I want to ride it alone. So when I got home for the summer, all de-virginized, horny and full of fantasies, and Mark asked me to house sit while he went away on business, it seemed like a sign from the heavens. Mark was going to be gone for a week. He gave me the key and a slightly lingering hug that was more than a bit uncomfortable on my end, and then he was gone leaving me alone in his house. I told myself that I wasn't just here to ride the Sybian. I didn't even know if I could get into the room. So I wandered around the house a bit, re-familiarizing myself with it, taking my stuff up to the guest room. He hadn't changed anything in the months since I'd been away. Even though my parents were right next door, it was always a nice feeling of freedom to be at Mark's. I could eat what I wanted, watch whatever I wanted on tv, look at whatever I wanted on my laptop without worrying that one of them was going to pop up behind me and see what was on my screen, and just do whatever I felt like. The good life. Almost like being a real adult. After making myself a sandwich for lunch, I wandered down to his basement. It was a smaller space, with an entertainment center and a dartboard, the main portion of the basement was sectioned off. I assumed it was all the room for the Sybian, which made me wonder how big the damn thing was. I tried the door. Just to check. Locked. Not a shocker, it always had been. I guess some part of me had just hoped. Sighing, I finished off my sandwich and went to watch TV. The next day I found myself back at that door, examining the lock. And by examining, I mean the inside of it with a paper clip that I had unbent. When you're a kid, you experiment with trying to open doors that you're not supposed to, and sometimes you managed it and sometimes you didn't. Unfortunately this time my search for a spring in the lock mechanism was unsuccessful. After about an hour I gave up. Okay, so it was probably half that amount of time, but it felt like longer. The point is, I knew pretty quickly that I wasn't going to be able to pick the lock but I kept trying for a little bit longer anyway and ultimately I failed. The old saying is that third time's the charm, and I guess that goes for days too. I'll admit, I'd kind of given up by the third day. I mean, yeah, I still wanted to get into that room and see the Sybian and maybe even ride it, but I just didn't really think it was going to happen. And, of course, when I'd given up, that's when I found it. I was looking through the drawers in Mark's computer desk for some scrap paper that I could write down the name of a website that I'd just found and wanted to remember when I came across a little box. I can't explain why I opened it. Curiosity. Boredom. Or maybe it was just fate, pushing me forward to my doom. But as soon as I opened that little, innocuous box and saw the key inside, I immediately knew where I was going to try it. I rushed downstairs, key in hand, not even bothering to close down the browser on the computer. Details! Breathless and almost dizzy with anticipation, I pushed the key into the locked door. And found myself in Narnia. A fucked up, kinky, dark Narnia. No lamppost, but there was a stripper pole in the center of the room, which was much larger than I had realized it would be. It was obvious that Mark had decided to devote the majority of his basement to his kink. There were all sorts of things I'd never seen in real life before, although I definitely recognized them from the internet: a spanking bench, a sex swing, one of those foldable sex chaises, paddles and whips on the walls, and several shelves adorned with all sorts of goodies. But the main thing was at the back center of the room, next to the wall socket. The Sybian. Almost reverently, I walked over to it. It was at the perfect height for straddling and riding, currently set up with two gigantic cocks. Could a woman really get something like that in her pussy? Much less her ass... much less both. I've never had anything in my ass before although I like reading stories about it. I wanted to ride it, but there was no way I was going to use those huge dildos for my first ride. Fortunately, there was a shelf to the right of the Sybian that looked like it was holding various options for attachments. After all my research online about the thing, it didn't take me long to pick out a decent sized cock - maybe seven inches long and an inch around - and replace the two massive fuckers that were currently on it. Feeling deliciously wicked as I stared at that fake cock sticking straight up, ready and waiting for me, I stripped off all my clothes. I know that wasn't necessary, but who wants to ride a Sybian wearing clothes? I felt horribly naughty being naked in Mark's basement, about to use his dirty sexy toys, but at the same time incredibly excited. Part of me was turned on by the fantasy that he might come home from his trip early and catch me down here, watching me ride the Sybian and then doing all sorts of nasty things to me. Yeah, I know... I said I wasn't into him and I'm NOT... but there's definitely something about the forced fantasy that gets me going, and at that moment it seemed like the most likely possibility. Holding onto the remote that I'd found on the shelf, I experimented a bit with the buttons, watching the movements of the cock so that I'd know what to do. It did all sorts of cool things, pump up and down a bit, vibrate, spin, and circle like a cock blender. I couldn't wait to get it inside me. Finally I stopped its motion and straddled the big machine, using both of my hands on the large hump part to balance me as I lowered myself onto the fake cock. It wasn't hard, my pussy was dripping wet just from standing naked in Mark's basement, fantasizing and watching what that dick was going to be doing to the insides of my pussy once I started it up. I moaned as it filled me up, stretching me just enough to be pleasurable. Ignoring the remote for now, I took a few minutes to bounce up and down on the shaft, enjoying the way it filled me. Even just in this position, this was way better than my regular masturbating - for one, no strain on my arm, wrist or fingers. Hell I could probably get off just like this. But that wasn't the point. So I pushed the button. OH FUCK. Immediately my pussy clenched as the dildo inside me began to move in circles, vibrations assaulting my clit where it was pressed against the mounded top of the Sybian. It felt amazing. Throwing my head back, I moaned as I began to move my hips on top of it, bouncing very slightly and adding an entirely new sensation to compete with the others. My pussy was getting the massage of its life while the vibrations shuddered through me at high speed; it was the most intensely erotic moment of my life and it was just going to get better. My breasts bounced as I gyrated on top of the fucking machine, my butt humping up and down, and my pussy lips and clit were mashed and rubbed against the vibrating seat. It hummed and buzzed against my vulva and swollen clit, and then the humming stopped and it started an intense pulsing. The sensations were randomized, working over my young body; I could feel it throughout my entire lower body. Moaning and gasping, I rode that fucker, and it didn't take very long before I was crying out in orgasm, grinding down hard on that fat cock as it swirled inside me. It rubbed over my g-spot again and again, giving me the most intense orgasm I'd ever experienced. My clit throbbed and hummed, getting into the action until the tiny nub became too sensitive and I had to lean back to take the pressure off. But the fucking of the dildo continued, up and down, whirling in circles, spinning inside of me and continuing to pleasure my hot pussy. My cream was dripping down onto the machine, as I came again, this time keening high and shrill as my body trembled on top of the Sybian. I hadn't even needed the clit stimulation, my g-spot was getting worked over so well. My breasts bobbled as my head fell back and I jerked and sobbed with extreme ecstasy. It was almost too intense, but I couldn't stop... not yet... I began working my tired thighs again, bouncing slightly, leaning forward to press my clit against the pulsing vibrations again. A third, giant orgasm, the big daddy orgasm of them all, was looming on the horizon. I could feel its approach like a summer thunderstorm. My body was becoming shiny and slick with sweat, my pussy was going to be sore as fuck, and I didn't care. I was lost in erotic need, wild from my first ride... The Sybian fucked me, mindless and relentless, created to do one thing and one thing only. Make women cum. I screamed as my climax plowed into me, curling my toes, curling my fingers, curling my entire body in on itself. My clit was throbbing as it was mashed against the vibrating machine, my g-spot screaming for surcease, and the pleasure was so intense, so overwhelming that I found myself jerking upwards and off the machine. The dildo whirred obscenely for a moment before I hit the correct button on the remote, and I stumbled a foot to where there was a small bit of carpet and a couch, and I collapsed on the floor. Gasping. Body humming. Legs spread, arms akimbo, completely wrung out from the incredible machine. My pussy felt sore and battered, and oh so replete. Completely satisfied. Satiated. My ride had been beyond my wildest dreams. And I knew it wouldn't be my last. ****** I'm not ashamed to say that I spent some time every single day down in Mark's basement. I didn't always go immediately to the Sybian, I also checked out some of the other toys he had. Tried a few of the whips of my thighs, just out of curiosity. I even tried to put some nipple clamps on myself, but they hurt too much. I'd thought they might be cool for while I was riding the Sybian, giving me some extra stimulation on a part of me that the machine didn't touch. But I just couldn't handle the strength of the pinch - I mean, seriously, OUCH. But that was okay because after a couple of days I was good enough at balancing on the machine to play with my own breasts, at least for a little bit. I can't say I really got used to the sensations, but I did get better at handling them. I could stay on the machine for longer and longer, taking more of its fucking and racking up orgasms like they were carnival prizes. By the end of the week I was using a larger dildo, but I still hadn't put anything in my butt. Like the nipple clamps, I did start to try to put one of the slimmer dildos into my own ass, but it just felt too wrong and kind of painful so I gave up. Not worth it. My last day there, I rode the Sybian for my longest time yet - a good fifteen minutes - and had about six orgasms. The last one was actually kind of really painful, but I didn't care. Mark was coming back and it was my last chance to ride. Once my watery muscles had recovered, I had meticulously cleaned every single toy and put it back exactly where I had found it. The Sybian was set back up with the two giant dildos it had originally held, and looked completely untouched. I was proud of myself, putting the key back in the box I'd found it, sure that Mark would never know I'd been taking illicit rides on his toy. I'd indulged my fantasies, without being watched by my creepy neighbor. He came home, thanked me for taking care of the house, and sent me on my way. Same as always. Except that I was smugly satisfied and smiling to myself about how I'd gotten away with riding the Sybian. Anticipating the next time he went out of town and I'd have his house and that delightful downstairs room to myself. To this day, for the life of me, I will never understand how I went that entire week and never noticed the cameras. Annie Rides the Sybian Ch. 02 About a week after Mark had gotten home, he called me and asked if I could come over. A little zing of apprehension went through me when he did so, but he sounded so normal that I figured he couldn't know how I'd found the key to his downstairs kink room, gotten in and spent all week taking illicit rides on his Sybian. Mark's a pretty nice older guy, not too bad looking, but a little creepy and he was always making remarks about how he'd like to see me ride the fucking machine. I'd always wanted to take a ride, just not with him watching, and I'd finally gotten to fulfill that fantasy while he'd been out of town and I'd been house-sitting. I was sure that I'd put everything in that forbidden basement room back the way I'd found it and that there was no way he could know what I'd been up to while he was away. Even if he suspected, it's not like he could prove anything. I'd been meticulous about my cleaning and organizing. Plus, seriously, he sounded SO NORMAL on the phone. Not like anything was wrong or he was mad or anything. So I figured it must have to do with something else. Had I accidentally killed a houseplant or something while I'd been lost in my Sybian-infused haze? I didn't think so, but then again, I'd been pretty obsessed with that machine while I was there, I could have forgotten to water some of the plants. So imagine my surprise, when ten minutes after I arrived at Mark's house, I found myself sitting on his couch, watching my naked body bouncing up and down on his television. "Oh my god... oh my god oh my godohmygodohmygodomigodomigod..." "Now, now, calm down, Annie," Mark said smugly, patting my knee. I was so distressed that when he'd first put his hand there, I hadn't immediately made him remove it. Now I was just frozen. Horrified. Terrified. And feeling like a complete idiot. "Mark... I'm so sorry... I didn't... I mean..." "Annie, Annie," Mark shook his head, hitting pause on the television. I was finally able to jerk my shocked gaze away from the screen and look at him. He didn't look mad. He looked... excited. Predatory. "No need to apologize. I can't count how many times I've told you that I'd love to see you take a ride on my Sybian. Of course, I did mean for me to be there when you did." I couldn't think of anything to say, so I just kind of nodded jerkily. I could feel doom clouds gathering around me, piling up like a brick wall about to come tumbling down over my head. "I don't think we need to tell anyone about this... not as long as you're willing to finally grant my request." "Your request?" I croaked. My voice sounded gawd-awful, but who could blame me? I was more than overset, I was practically fucking falling apart all over his couch. Mark grinned, his teeth looking whiter than usual. Like the untrustworthy smile of a used-car salesman. "To watch you ride my Sybian. In person." I recoiled. "Of course, if you'd rather I provide a copy of this to your parents so they know what their daughter has been doing while at my house... I could even put it up online..." Immediately I shook my head. Trapped. I was trapped. The worst part was, my pussy was kind of wet. I don't know if it was the mere mention of the Sybian, the fact that my dark fantasies had often revolved around forced seduction, or what, but part of me was aroused. Stupid body. "Good." Mark squeezed my knee, his eyes wandering over me in a completely lascivious manner. "Come on then." "Now?" My voice squeaked. He laughed and I blushed. Could I sound any more like a complete airhead? "Why not now? Get it over with, as it were." His eyes challenged me. Later I would wonder if he was worried that I might renege on our deal if he didn't get me down in the basement right away, or maybe he was just too turned on to want to let me go. Who knows. "Come on Annie, come and ride the Sybian. You know you want to." And I did. That was the truth. My pussy throbbed at the idea. Do you have any idea what it's like to go from mind-blowing multiple orgasms every day to nothing? Nada? My fingers and vibrators just couldn't do the same thing as that amazing machine. Like a zombie, like I was in a dream, I followed Mark down the stairs to the basement. The door to his kinky room was already unlocked, the Sybian already set up with the same dildo I'd used before. There was only one difference - he'd also set up a very slim, short dildo that was obviously meant to go in my butt. I shook my head, pointing at it. "I can't use that." "Yes you can. I'll help you." His eyes seemed to gleam and I shivered. Okay, so a lot of my forced fantasies had forced anal in them. At least the dildo looked small. It was less than half the size of the one that was obviously meant for my pussy. But that didn't mean I wanted it actually going into my virgin hole. But my stupid body got even wetter and hotter at the idea that I might not have a choice. "Might as well start stripping," he said, as he grabbed a bottle of lube. Trying to act nonchalant, knowing that I didn't have a choice, I pulled down my pants and my underwear. Covering my mound with my hands and crossed legs, I watched as he lubed up both of the dildos. I didn't know whether or not he'd really show the video to my parents – did they know he had a Sybian or any of the other kinky stuff down here? – I was more worried about him putting the video up on the internet. That kind of shit ruined lives. Plus, then my parents might see anyway. Mark glanced over at me and laughed. "So modest now? Your top too, Annie." "I don't need to take my top off to ride the Sybian," I argued. "No, but I want to watch your tits bounce while the machine fucks you. Besides, I know you prefer riding totally buck ass naked, since that's the only way you've ridden it." I blushed. Obviously he had more than one movie if he knew that. And it was true. I hadn't worn a stitch of clothing any of the times I rode the machine. Still, I hesitated until he looked up at me and gave me a threatening kind of look. Not a glare, exactly, but just a promise of retribution unless I did exactly what he said. The worst part was that even though I still thought he was a creeper, even though this entire situation kind of frightened and disgusted me, I could still feel myself getting even more turned on by his demand. Stupid fucking body. "Strip Annie. All the way." In order to do so, I had to uncover my pussy, and I swear I could feel his eyes on my mound even though I squeezed my thighs together as tightly as I could. Unable to make eye contact with him, I looked away as I dropped my shirt on the floor and pulled off my bra. Immediately my nipples stiffened in the cool air of the basement and I shivered, wrapping my arms around myself. I probably looked so fucking cliche, one arm over my breasts, the other reaching down to cover my mound. But I didn't care, I just didn't want him looking at all my parts. Even if he'd seen them before on a video screen, it was different. I looked over at the Sybian, which had the two dildos sticking up obscenely. Mark was standing right next to it, pure lust and hunger in his eyes. And just looking at the machine, I could feel my pussy gushing with anticipation. I was like one of Pavlov's dogs, and the Sybian was my bell. I'd conditioned myself with it all last week, riding it every day... and in the days since I'd returned to my own home, I'd missed it. "Get on it." "Yeah, yeah, I know," I muttered under my breath. I wanted to sound defiant, but I think mostly I just sounded kind of pathetic. I just hoped he couldn't hear the slight hint of eagerness in my voice. Yeah, I'd never wanted Mark to watch, I was humiliated and horrified by the situation, but part of me couldn't wait to sink my pussy down on that wonderful machine and ride it into sexual glory again. There was no help for it, I had to uncover all my private bits in order to balance as I straddled the machine and began to lower myself down onto it. The dildo going in my pussy touched me first, I was wet enough that it pushed in easily, making me moan a bit. I did my best to ignore Mark, who was standing slightly off to the side and far too close to me for comfort, watching my every move with hungry eyes. The rubber cock slid deeper as I lowered myself, stretching my pussy enjoyably. Of course, as soon as I reached the height of the slimmer, second dildo, I stiffened. "You look like you need some help," Mark said, lasciviously. I glared at him. His hand was on the front of his pants, over his obviously bulging cock. "No, I don't," I snapped back. "Well then get a move on." It took a little bit more maneuvering, and my thighs burned as I reached back to separate my butt cheeks even further and to make sure the dildo was place correctly. The tip was cold and slick as it nudged against my virgin hole, and I winced as it pushed into me. I even sent Mark a pleading little look, hoping for a reprieve. He just stepped forward, put his hands on my shoulders and, before I could stop him, pushed down. My thighs screamed with hot agony and the muscles gave out, I sat down heavily on top of the Sybian, my butt protesting as the (thankfully) thin dildo was shoved completely into it. Even though it was a lot smaller than the one in my pussy, I could still feel my sphincter stretching uncomfortably, the delicate walls of my inner tract burning as they were violated for the first time. My pussy throbbed and clenched, feeling the pleasure all the more acutely. The dildo filling my cunt felt even bigger, as the one in my butt had given it less room to work with. I moaned and squirmed on top of them, and before I could really even get used to feeling them inside me, Mark had pushed the button on the Sybian. It came to life immediately inside me, both of the dildos rubbing the walls of my tunnels as they circled. My head fell back and I gripped the hump of the Sybian for balance as I struggled to deal with the overwhelming mix of sensations. My pussy was in heaven, clenching and juicing as it was fucked by the Sybian. My ass was more conflicted, cramping slightly as it tried to adjust to its new proportions and the movements of the Sybian, and yet it felt kinda good too. New nerve endings had come to life, ones that had never been simulated before, pleasurable ones. I cried out, shuddering and instinctively moving up and down a bit, humping the machine. Out of the corner of my eye I could see Mark's cock was now out, his hand wrapped around the thick length as he jerked off, watching me ride the Sybian. But my body didn't care anymore; it was finally getting what it craved. "Oooooh fuck..." I gasped and shuddered as the vibrations on the hump started up, humming through my pussy lips and clit. My pussy and ass clenched spasmodically around the dildos inside of them, increasing the intensity of the sensations as they circled. It felt like every part of my groin was being massaged, rubbed, pleasured. The pain and discomfort in my ass had almost completely faded and become part of the symphony of ecstasy that was building up inside me. Dammit... why hadn't I tried a dildo in my ass before? It felt amazing... but no, it had taken Mark forcing me to sit on it. And with that thought I had my first orgasm, my young body rocking and jiggling up and down as I threw back my head and cried out with passion. The Sybian continued its relentless assault as I rode it, spinning and pumping and extending my orgasm. Mark had shifted to stand right in front of me, his cock pointing straight at my tits as they bounced up and down, shaking with the force of the machine's fucking. The hot light in his eyes said this show was everything he had ever wanted. And I didn't care anymore. I didn't care that he had forced me or that he was watching; all I cared about was the hot warmth between my thighs, the fantastic rapture exploding inside of me. When he reached out to cup one of my breasts with his free hand, I didn't even protest. It felt good. Remember, I'd tried to play with my own tits while riding and had trouble balancing; now he was doing it for me. At first his touch was tentative, but as I continued riding and moaning he became more bold, releasing his hold on his cock to take both of my boobs in his hands and squeezing them tightly. I cried out, the rough pressure of his hands making me shudder and contrasting with the pleasure that was building up again in my pussy and ass. I arched my back, wanting - needing - more and he pinched my nipples. "Oh fuck... oh fuck... oh fuck..." Mark squeezed the little buds hard, rolling them between his fingers and I came again, arching and grinding down and squealing and cursing. It was the most intense orgasm I'd had yet on the machine, my pussy throbbing hotly, my clit feeling swollen enough to burst. In fact, if I'd been alone, I would have happily gotten off at this point, but when I tried to rise up, Mark seemed to intuit my intention and released my breasts to push me back down. "Mark please, I can't do much more," I begged, but he was too strong and had much better leverage than me. "One more Annie, cum one more time for me," he said. Groaning, I sank back down. I wasn't at my absolute limit yet, but my body was already feeling super sensitive from the two orgasms. Whimpering, I forced my muscles to keep me upright. They felt watery and loose, but I could already feel sexual tension coiling in my belly again, my tender holes being expertly worked over by the incessant machine. It was going to be the granddaddy of all orgasms when it came. My nipples were throbbing from the roughness of Mark's pinching, my breasts felt swollen, and my ass and pussy were full and clenching. This was the most satisfying ride I'd ever taken on the Sybian, even if I had to put up with Mark standing in front of me and jerking off. Which he'd gone back to doing. I moaned and ground myself down on the Sybian, eager to cum again, eager to get off - in both sense of the phrase. "Fuck you're so hot, Annie... that machine is fucking you raw isn't it?" Mark's voice distracted me and I closed my eyes, trying to shut him out as he continued to tell me how hot I was, how much he liked seeing me writhe for him, watching my tits bounce. Some of it was kind of hot, some of it was definitely creepy. And then I felt it. Hot liquid splashing on my breasts and stomach. I opened my eyes to see more cum jetting out from his cock, which was pointed right at me. Stick white cream decorated the front of my body as he sprayed me. I couldn't even lift my hands to stop it, I was holding onto the Sybian and needed my arms to stay balanced. And maybe, deep down, some part of me was even turned on by it. Then his hands were on my breasts again, rubbing that sticky cream into my skin, squeezing the tender mounds and tugging on my nipples. The added sensations had me winding up, tight like a spring, my insides coiling and my outsides curling as my orgasm wound up and then exploded out of me. I screamed as Mark pinched my nipples hard, tears springing into my eyes from the intensity of the ecstasy boiling out from my pussy. My ass was squeezing down hard on the dildo inside of it, burning from the continued movement, just as my pussy was throbbing and clenching around its own intruder. I rubbed my pussy lips and clit against the machine, starting to sob as the incredible sensations overwhelmed me. This time when I pushed up and off the Sybian, Mark didn't stop me. In fact he hit the button on the remote to stop the dildos. I practically fell off - in fact I would have if Mark hadn't helped lower me to the carpet beside the machine. I was glistening with sweat, traces of his cum still decorating my belly since he'd been more interested in rubbing the white jizz on my tits than on my stomach, and I felt like I'd been put through a wringer. My muscles were more than watery, they were completely unresponsive. Which I quickly found out as Mark pushed my legs apart, kneeling between my thighs so that he could look at my pink pussy. "Mark noooooo," I protested, but my legs could only kind of twitch weakly and my arms were the same. I couldn't even reach down to cover myself as he stared lustfully at my swollen bits. The ride on the Sybian had left my delicate folds a bright pink, swollen and sloppy from all the juices it had leaked. My nipples were softening, but they were also darker than usual from Mark's rough treatment. Every inch of my body felt super sensitive, as if I was still cumming, even though he was just touching my thighs. When I looked down at my swollen, puffy pussy, I realized that Mark was hard again and I moaned. Fortunately he mostly seemed interested in just looking at me, at my pussy, as he fisted his cock in his hand and started jerking off again. Then his freehand stroked the tender folds of my pussy and I shuddered, partly with revulsion and partly with the intense pleasure that came from being touched at all. "Nooooo, please Mark, stooooop!" I hated my useless body, my unresponsive limbs, as he pushed two fingers into my wet, sloppy hole. There was no way to stop him as he ignored me and shoved them deep, causing me to convulse as the tips grazed over my g-spot. I gasped and clenched and he just laughed at me, jerking his cock harder while his fingers worked inside me. I could hear the sloshy wet noises as he frigged me, even over the small whimpers coming from my mouth. I wanted him to stop touching me, and at the same time he was causing little bursts of pleasure, like mini-orgams or aftershocks to spark off in my body. My legs and arms twitched, my watery muscles shaking as I squirmed and moaned... but I couldn't even squirm away from him. "Fuck yes..." He groaned as he wanked himself harder, I hoped that it would be over soon. His fingers dug deep and made me gasp and then he pulled them out and slid them down, shoving them into my ass. I cried out, because it hurt... his two fingers were actually wider than the dildo that had been attached to the Sybian and my poor virgin asshole had already been given a thorough workout by the machine. It was tender and not at all ready for his rough invasion... and yet my pussy just spasmed emptily as he fingered my ass just as deeply and thoroughly as he had my wet hole. Fortunately there was still plenty of lube up that tighter entrance, not to mention my pussy juices coating his fingers, or it would have probably hurt a lot more. And even so, pleasure still sparked through me, my body so sensitive and ready for more sensation. Mark's breathing was getting faster, heavier, as he fucked my asshole with his fingers, muttering about how tight I was and how sexy I looked all spread out with his fingers up my ass. I finally had my arms in some kind of working order and I managed to reach down and weakly grip his wrist with my hands, but I didn't have nearly the strength I needed to stop him - and that just seemed to turn him on more. He forced a third finger into my asshole as I cried out and begged him not to, and then suddenly hot cum was shooting out of his cock and onto my body for the second time that day. It spattered onto my stomach, my arms, and the parts of my mound and pussy that weren't completely covered by my protesting hands. The fingers in my ass jabbed me deep one last time, forcing my body to arch, as if it was asking to be decorated in his jizz. Panting heavily, Mark gave his cock a last few jerks and then sat back on his heels, withdrawing his finger from my ass. I wanted to give him a dirty look, but I was too wrung out. I just lay there as he pulled his clothes back into some semblance of order and then picked me up. I didn't even protest as he wrapped me up in his arms and carried me out of there. Annie Rides the Sybian Ch. 02 A few hours later I woke up in the guest bedroom I usually stayed in and there was no sign of Mark. My clothes were piled neatly at the end of the bed. When I moved I felt something pull on my stomach and I made a face as I realized that he'd left me coated in his cum. Ew. Must be a guy thing to not care about that, because I thought it was pretty gross. Still, I ignored it while I dressed as quickly as I could and hurried home to get a shower. My poor pussy and asshole were still sore as I walked, making me wince and kind of waddle a little bit, but at least I got out of the house without running into Mark. At that point I didn't know if I would ever be able to face him again. Of course, it's not like I would really have a choice. Annie Rides the Sybian Ch. 03 After Mark watched me ride the Sybian, I spent a lot of time sneaking out of my own house. I just didn't want to run into him, which isn't always easy when you're next door neighbors. But I managed it, mostly by watching out for when he was leaving. Since he worked a regular schedule that made things a bit easier. I'd started having dreams about him watching me while I rode the Sybian. Sometimes he touched me. Sometimes he didn't. Either way, I woke up wet. Talk about humiliating. Of course I didn't want him touching me again... but my body was still craving the Sybian. It had been over two weeks since my last ride and I was masturbating at least once a day just to hold my cravings in check. Since I didn't have a boyfriend, or even a fuck buddy, and I wasn't really into one night stands, I didn't exactly have a lot of choice for outlets when it came to my overwhelming sexual energy. It was like the Sybian had unleashed some kind of powerful force inside of me, a needy, demanding force. One that didn't care that my creepy neighbor wanted to watch me and touch me in order for me to ride. I'd started inserting things into my ass when I played with myself too. Nothing bigger than the dildo that had been attached to the Sybian when Mark had forced me to ride for him, but that little virgin hole was getting a heck of a workout. I loved the extra feeling of fullness, now that I was used to it, and I even liked the slight burn and discomfort of being stretched when something was first inserted. But it still wasn't the same. Maybe it was just the amount of time since my last ride, but my stupid head was starting to wonder if I would be willing to pay Mark's price to ride again. And then he took my choice away from me. Looking back, I think I actually felt a bit grateful for that at the time. I mean, I REALLY wanted to ride the Sybian again, but admit that it was worth Mark's voyeurism and touching in order to do so? Yeah, I couldn't do that. But when he forced the situation, I meant that I didn't have to... and I still got to take another ride. And, at the time, I didn't know that the price would be higher. It was about two weeks after I'd ridden the Sybian in front of him that he called my cell phone again. Just seeing his name pop up made my stomach churn with anxiety even as other parts of me fluttered with excitement. At this point it was halfway through the summer, halfway to being far enough away from him that I could forget the damned machine and not have to worry about his sordid demands. "Hello Annie," he purred when he answered the phone. The second I heard his voice it was like I was back in that basement, his hands on my breasts, his fingers sliding into my cunt... and I shivered. "What do you want, Mark?" I asked shortly. I was so not in the mood for social niceties. He just chuckled. Creepily. "I want you to come over and entertain me again, Annie. I was hoping you would call, but since you hadn't I decided to call you." "I guess I just didn't want to ride again as badly as you thought I would." "Maybe." He didn't sound convinced. "But the point is moot. Come over tonight." "I can't, I have plans." "Then come tomorrow. Unless, of course, you want the entire world to see you riding it." The silky tone in his voice made it clear that his threat wasn't idle. Which, I'd never thought it was in the first place. "Fine," I grated out. Not like I had a choice. "I'll see you then." He hung up and I cursed. Not just him, but also my traitorous body which was already humming with excitement. It wanted back on that machine. No matter how much I'd masturbated, how much I'd played with my own ass, it hadn't quite been enough. My pussy was practically singing with happiness at the thought of being back on the Sybian. ****** This time when I showed up at Mark's, I was both nervous and wary. When he opened the door, I found that I couldn't look him in the eye. It had been different before, when I hadn't known what I was there for. Now I knew and I was ashamed of myself for getting caught and being put in this position, and even more ashamed that my nipples were already hard and my pussy was already wet - even though I'd wiped it dry before coming over. "Come on in, Annie," he said. I could practically feel his eyes sliding over me, anticipating when I was going to be stripped down for his viewing pleasure. Or maybe that was just my imagination, but that's what it felt like. I followed him down to the basement without saying a word to him. It's not like we needed to chit-chat, I knew what I was there for. As usual, my gaze went straight to the Sybian as my pussy lips plumped even further, swelling with arousal. My eyes widened as we approached. "Those... look bigger than last time," I said, pointing at the cocks. I couldn't be sure though, because they weren't hugely bigger, but I was pretty sure that the ones I'd ridden the last time had been smaller. Giving me a pleased look, Mark grinned. "Why yes... yes they are. Don't worry, I'm sure you can handle it." I bit my lip, knowing it would do no good to protest, and also because I was kind of excited by the idea. Last time I wouldn't have been, but like I said, I've been frigging my asshole on a regular basis at this point. Getting plugged by bigger toys didn't sound as frightening as it could have. "Come on Annie, strip down. Let me see that gorgeous body." Shuddering, I started to pull of my clothes, giving Mark a little glare as he watched me strip. "No touching me while I'm on the Sybian this time," I said. He gave me a look, considering. And then smiled. "I'll tell you what, I'll make you a deal. Let me put these on you," he reached out and picked up a pair of nipple clamps from the shelf next to the Sybian, "and once they're on, I'll have no reason to touch your tits again." Looking at the wicked little things, I licked my lips, remembering how much they had hurt. But wouldn't that be a small price to pay for him to keep his hands off me? And I really did like having some kind of pressure on my nipples... maybe it wouldn't hurt so badly if I was riding the Sybian when he put them on. "Fine," I said. "But you have to wait till I'm on the Sybian to put them on me." Mark nodded his agreement and waved his hand at the machine now that I was completely naked, obviously eager to watch me ride it. I was torn between my conflicting emotions as I spread my legs over the machine and began to sit down. Like last time, he'd obviously prepped the dildos with a bit of lube, more on the one going in my ass. Truthfully, the one going in my cunt didn't need it, but it's not like I was going to admit that to him. Biting my lip against a moan, I pressed down on the thick shaft that nudged against my pussy. It was cool and slick against my heated flesh, making me shudder as I bounced gently and worked myself down on it. Doing my best to ignore Mark's avid stare and the way he was rubbing the front of his pants as I did so. There was only about an inch or so of rubber cock in my pussy when I felt the other dildo nudging against my asshole. I shifted slightly to get the target perfectly lined up and then let gravity continue to do its work. The tight ring of my sphincter burned as it opened wider than ever before, making me gasp and close my eyes as I began to work myself up and down on it. I felt so tight inside, the dildos so much bigger than anything I'd been playing with by myself. Both my pussy and my ass burned uncomfortably and wonderfully as they were filled. I had to concentrate to keep from groaning with pleasure as I forced myself further down on those upright shafts, my legs beginning to tremble with the strain. Finally my thighs gave out and I sank down completely, my asshole protesting a bit at the rude intrusion, my pussy clenching with glee around the thick rubber. When I opened my eyes, Mark had his cock out and was already rubbing it, his eyes hot with lust and hunger. "Push the button," I demanded. Not because I wanted to get this over with... because I wanted to get it started. The machine whirred to life inside of me, vibrating so deep in me that I could feel it all the way in my throat, and this time I couldn't stop the moan. I shuddered and my thighs clenched tightly around the Sybian. Mark's hand closed around my breast and I opened my eyes to glare up at him. He just grinned evilly back at me. "Hold still." It was harder that it sounded. I wanted to wriggle and move on the machine; the humming vibrations against my pussy lips and clit were almost too intense to bear for very long. Mark pinched my nipple harshly, making the little bud stand up even further and I whimpered as the flash of pain mingled with the pleasure that was already coiling in my belly. My groin felt warm and full and tingly with need. When he put the clamp on my poor little nipple I let out a loud cry and tried to reach up to take it off, but he grabbed my hands and force them away from my body. Whimpering, I jiggled and moaned. "Let me go, take it off, let me go, take it off!" "Shhh, just breathe through it," he said. "It'll hurt a bit less in a minute." I wanted to demand to know how he knew, but he was right. Maybe it was being on the Sybian, but the biting, sharp pain was slowly fading. Reluctantly I stopped struggling against his hold and lowered my hands. As he cupped my other breast and pinched that nipple, prepping it, I bit my lip against begging him not to. His hands on my chest were warm and entirely unwelcome. I'd rather have the clamps, even if they did hurt. The one already attached to my nipple was making that tender bud throb, but it was bearable now. I could do this. I hissed through my teeth as he attached the other clamp. Knowing what to expect made it a little easier, because I also knew that the sharp pinch would lessen, but it also made it worse because I knew exactly how bad it was going to hurt until my poor nipple got used to it. At least the pulsing cocks inside of me helped to distract me from the painful throbbing of my nipples. Part of me really understood why Mark might like watching me, as he stepped back. I kind of wished I could watch myself, with my young body stuffed with cock, bouncing up and down, dripping pussy juices, breasts jiggling, hard nipples clamped with silver... I wished there was a mirror that I could watch myself in. Not that I'd ever admit that to Mark. The tight pressure on my nipples was starting to feel really good in contrast to the complete pleasure that the whirling cocks were stirring in my lower body. Mark watched me, pushing another button on the remote, and the cocks started to thrust, alternating which was pushing in as the other pulled out. Both of them rubbed over sensitive spots inside of me, causing flashes of incredible pleasure. I cried out, my back arching and thrusting my breasts forward, as if offering up my clamped, red nipples for his enjoyment. But he kept his word and didn't touch me. He just watched as I cried out in orgasm, rubbing my pussy lips and clit against the vibrations. My breasts bounced, my tormented nipples throbbing in time with the pulsing of my ecstasy, and the most wonderful feeling of satisfaction ran over me. I moaned and gyrated, my body loving every second of the ride even if Mark was watching. In fact, I think that some secret part of me was starting to like him watching. Starting to enjoy the desire, the hunger in his eyes. It made me feel even sexier, made the right even more fraught with forbidden desires and taboo fantasies. He was masturbating again, jerking his cock furiously as he watched me bounce and writhe on the machine. "Ooooooh fuuuuuck...." I shuddered and my thighs clamped down around the vibrating base as another wave of incredible pleasure rolled through me. The constant pressure on my nipples had become indescribably exciting, only the tiniest sparks of pain complementing my pleasure as the little nubs were jolted about on my jerking body. Like before, Mark stepped closer to me as I panted and pulled myself slightly upwards, whimpering as I gave myself some much needed space between the seat and my sensitive pussy lips. My clit was swollen, throbbing, and too sensitive to touch much less be pressed against the vibrating hump. And because I was using my hands to keep my body off of the hump, I couldn't bring them up to stop the spray of his cum across my stomach. The warm jizz left white lines across my belly, trickling down and leaving sticky tracks on my skin. Part of me wanted to screech EEEEEEEEEEW like a little girl faced with a bug, but I was already too wrapped up in the next orgasm that was coming at me. The warm liquid trickled down and I could feel it gliding over my pussy lips and clit, so dirty and wrong and yet that just made my stupid body even more turned on. I closed my eyes and concentrated on the pleasurable thrusting.... which suddenly turned to whirling, circling around inside my vagina and anus, making them feel as though they were being stretched even further. I moaned and pushed myself back down fully onto them, feeling the wet juices of my cream and Mark's jizz sloppily smushing between my pussy lips and the seat of the Sybian. The orgasm that had been building inside of me came spiraling up, sizzling over all my nerve endings, sending me flying high on a cloud of rapture that seemed to encompass my entire being. I'm pretty sure I screamed as the explosive heat went through me, rocking my center of gravity. I could feel Mark's hands on my shoulders, but I knew that he was just trying to keep me from falling off the Sybian. I was lost in the rolling waves of a multiple orgasm that just kept cumming and cumming and cumming... I reached out to grab at Mark's arms, needing to lift myself off of the machine, needing to get away from the climax that had become so intense it was painful instead of pleasurable. My body was spasming uncontrollably, my insides clenching around the relentless massaging of the machine, but there was no stopping its effect on me and I couldn't get away unless Mark released me. Tears rolled down my face as I gripped his arms, trying to use them to leverage myself up. "Mark pleeeeeeeeeeeease..." I begged, my back arching again as painful fireworks assaulted my clit. "Say I can touch you Annie. Say I can do whatever I want." I screamed, my body rocking as a huge explosion went through me. I was sure the pleasure was killing me, it felt like my brain was underwater and like my body was a battleground of sensation. He was holding me pressed down so tightly to the machine that there was no part of my sensitive genitals that had any relief from the non-stop stimulation. "Say it, Annie, and I'll let you up." Mark's voice was rough, needy, but I didn't hear that. All I knew was that I needed to get off of the machine before it fucked me into oblivion. "You can do whatever you want!" My body tightened and exploded again. I wasn't gripping Mark's arms anymore, I was hanging on for dear life, my muscles far too weak to do anything else. He left me there, being fucked by the Sybian, for just a moment longer, cumming hard, before he lifted me off. My body was still spasming, my muscles completely useless as he lay me down on the carpet and turned off the machine. In the back of my mind, I knew he was going to touch me again, but I didn't care. I was pleasure-fogged, riding high on endorphins and orgasms, and his hands seemed so very far away even as they squeezed my breasts. Then he pulled off the first nipple clamp and THAT I felt. Blood rushed back into the tiny, sensitive nubbin and I screamed. He was already leaning over and sucking it into his mouth. I might have begged him to stop, but it actually soothed the tortured bud to be suckled, his tongue laving gently over it, so I just whimpered and let him have at it. Anything to stop the feeling of prickling needles stabbing my poor nipple. He took off the other one, ignoring my screech as he moved his mouth over. I looked down to see him at my breast, his sucking creating a sympathetic throbbing deep in my overstimulated pussy, and I wondered if I might cum again just from him sucking my nipples. The surface of my skin was so sensitive that it felt like a real possibility. I shuddered and moaned, feeling the back of his hand moving against my inner leg, knowing that he was hard and jerking off again. I should have expected it, but I think I was too lost in my body for my mind to be working coherently. The next thing I knew he was draping my legs over his elbows and lining his cock up with my pussy. "Mark noooooOOOOOO!" My voice got higher and louder as he shoved in. My pussy was wet, stretched from the Sybian, and my muscles too weak to stop him. It was just like the last time, but so much worse. Groaning with pleasure, Mark leaned over me, his body hair abrading my sensitive nipples and I gasped and squirmed. My hands came up to press against his chest, but I couldn't even find the strength to shove him as his cock buried itself fully inside of me. He was just as big as the Sybian cock, but with more give, a steelier core, and a much hotter temperature. "You said whatever I want," he whispered in my ear. And then he started fucking me. Hard. I winced and shuddered and clenched beneath him as his thrusting cock brought back all the sensations that I'd begged to be taken off the Sybian to get away from. Even if his cock couldn't do all the things that machine could, I was so sensitive, so attuned to pleasure, that it didn't matter. I could already feel another orgasm building inside of me, even though he was raping me... or had I consented? My mind was so confused, I felt like I was being sucked down a dark tunnel and the only lights were the little white explosions going off behind my eyes. "Are you on the pill, Annie?" he asked, his voice rough in my ear. He was so turned on my ravaging my young body after watching me on the Sybian that I could tell he was getting near cumming again. So was I. I shook my head. He pulled out. Disappointment that my building orgasm was going to go unsatisfied was tempered by relief that he wasn't going to cum in me and relief that I wasn't going to be forced through another painfully ecstatic orgasm. I thought he was just going to cum on me. Instead, he shoved his cock into my ass. I screamed as he took my anal virginity, more out of shock than pain. My ass was already well stretched from the Sybian, and even though he was bigger the discomfort of the further stretching wasn't overwhelming. But I hadn't been expecting that. And he felt strange inside my ass, even stranger than the Sybian did... so hot and throbbing and... and... Oh fuck... I was going to cum again while he raped my ass. I'd had so many forced anal fantasies, but I never really thought someone could come from anal sex. Not JUST anal sex. But his body was banging against my sore pussy lips and swollen clit, the slick glide of his cock in and out of my ass was burning in an incredible way, and the head of his cock was sliding over some spot deep inside of me that I hadn't known existed. Like a g-spot, but in my asshole. Or maybe my body was just so sensitive at this point that anything would have made me cum, I don't know. "Oh fuck... oh fuck Annie... oh fuck your ass is so hot... Fuck... Fuck... FUCK..." Mark panted and drove into my ass like a jackhammer, using the same rough thrusts that he had when he'd been raping my pussy. That tunnel just pulled me in deeper and I screamed, arching involuntarily, grinding my ass down harder on his cock as the waiting orgasm swelled and burst over me like a tidal wave. Annie Rides the Sybian Ch. 03 I was rocked by his thrusts, even as I felt him swell and pulse, my ass clenched down and milked the jizz from his cock. It filled me up, all hot and scalding against the abused walls of my tunnel, the strangest sensation I'd ever experienced, and yet it made me keep orgasming even through that. Even with Mark's heavy, warm weight on me, I was shivering as his cock shrank in my ass. My body and mind were overloaded, ready to shut down, but unfortunately this time I couldn't sink into easy darkness. The tunnel buffeted me, but I could still feel Mark's cock sliding out of my deflowered ass, the drip of cum as it followed. I could feel the last sucking kisses he gave my nipples and hear his pleased chuckle as he rubbed his fingers over my cunt and pushed them into me a couple times, as if he just wanted to hear the squelching juices of my pussy. I moaned a bit as he gathered me up in his arms and carried me upstairs to the guest bedroom. He laid me out on the bed, on my stomach with a pillow underneath my hips to push my ass up. Cum was still dripping out of my abused asshole and beginning to slide down my pussy lips. I could hear the click of a camera as he took pictures of my reddened lips, my dark red hole with the white drippings of cum, and the swollen, abused state of my entire nether regions. When he finally left the room, that was when I finally passed out. At the time, none of the things I felt or heard really meant anything to me. Sometimes when I hear people talk about being in a coma, but being able to hear and feel everything going on around them, I wonder if that's kind of like what I went through. But, like a sex coma. That summer was probably the most debauched of my life. I had experiences I'd never anticipated. I'd ridden the Sybian, but I'd also been molested and raped by my neighbor - or was it rape when I'd agreed he could touch me however he wanted? - and taken my first dildo and my first cock into my ass... At the tender age of 18 I was having the experiences that would shape my sexuality for the rest of my life. And the summer wasn't even over yet. Annie Rides the Sybian Ch. 04 After a few weeks, I was starting to think that Mark had forgotten about me. Which was a relief. Mostly. I mean, I still missed the Sybian. But I was adjusting, getting used to not having multiple orgasms. And my most recent experience might have jaded me just a bit. The orgasms had been incredible. The sex... well if it had been someone other than Mark then the situation would have actually been kind of hot. This was the kind of thing I fantasized about on a regular basis after all. It was just that I had always pictured someone that wasn't my creepy neighbor. My asshole had been sore for days after he'd taken my anal virginity, and all I'd needed to cum when masturbating was to press a vibrator against that tender ring. It had hurt more and felt better than I'd ever imagined. And when I read my usual dirty fantasies about forced seductions and taking girl's asses, my response was even bigger because I really could put myself in their place now. There were only three weeks until I went back to college, putting myself far away and out of Mark's reach. I hadn't seen him since I'd been over to his house. My parents had mentioned running into him, but that was about it. That had made me nervous but obviously he hadn't told them anything. Two weeks before I went back to school, my parents were going out of town for the weekend. I didn't think anything of it until Friday morning when I'd said goodbye to both of them, waved as their car pulled out of the driveway, and then my phone rang. It was Mark. Immediately my breathing picked up, my hands got clammy, and my pussy clenched. Stupid body. It didn't know whether to scream and cry or run to the bathroom and grab a vibrator. Talk about conflicting responses. "Hello?" "Hello neighbor. All alone for the weekend I see." Oh no. This couldn't be good. "How did you know that?" I demanded. "Ran into your parents last week. Remarkably chatty. They asked if I could keep an eye on you. You weren't planning on any wild parties, were you Annie?" His voice was silky, gleeful. "No. I was planning on staying in and doing absolutely nothing this weekend." It was entirely true. I'd wanted to keep a low profile. Damn my parents for talking to Mark. And keep on eye on me? Seriously? What was I, twelve? Then again, it's not like I'd been doing a great job of keeping an eye on myself lately. "Too bad," Mark said. "I feel like having a party. A Sybian party. Pack a back. Come over tonight. You're staying with me this weekend. And bring something slutty and school-girlish." He hung up before I had a chance to respond. I wiped my sweaty palms on the tank top I was wearing. Fuck. I didn't even know what I was feeling. Dread. Excitement. Horror. Lust. Disgust. Arousal. There was seriously something wrong with me. I went to pack my bag. ****** One hour later, Mark had come over to get me. My bag was packed. Had been for half an hour. I even managed to find the short plaid skirt, knee socks and cropped button down shirt I'd worn for a Britney Spears costume a few years ago. It still fit. I'd just been putting off going over to Mark's for as long as possible. Thankfully he didn't just shove me straight down into the basement like last time. Instead he let me unpack. He was watching TV when I was done and I joined him, sitting on the opposite side of the couch. We chatted. It was kind of surreal how normal it all was. Then he left me alone so he could make us dinner. It was over dinner that he dropped the bombshell. "Tomorrow night I'm having a couple of friends over." "Okay..." I said, not understanding at first. "So I'm just staying for tonight." Mark laughed. "No, Annie, you're staying the whole weekend. I told you, I want to have a Sybian party." I paled. "You want me to ride the Sybian in front of your friends?" I squeaked, dropping my fork onto the plate with a clatter. I'd suddenly lost my appetite. Fortunately I was almost done with the steak and green beans he'd made anyway. "You'll enjoy it," he said. "You're such an exhibitionist. You'll love it." Ugh. I felt my pussy actually clench at the idea, but I knew that it was sexier in my head than it would be in person. The faceless men in my head were always super sexy; Mark wasn't unattractive, but he wasn't like the men in my head. I doubted his friends would be either. Once he was done eating, he took our dishes and put them in the sink, before turning back to me with that hot look in his eyes that I knew meant we were going downstairs. My stomach churned and I was relieved that I'd stopped eating before him. I couldn't imagine getting on the Sybian on a full stomach. His eyes wandered down to my chest and I blushed as I realized my nipples had hardened in anticipation and were clearly on view through the fabric of my shirt. Stupid body. "Ready to take a little ride, Annie?" he asked softly. I wanted so badly to tell him to go to hell. But my pussy was already creaming and it's not like I really had much of a choice anyway. Still, I had some pride left, so I didn't nod my head, I just sat there and stared down at my hands in my lap. "Come on." And like the obedient little robot I was, I followed. ****** The cocks on the Sybian were bigger than the last time. Definitely noticeably. For the first time, the one that was going into my ass looked like a real cock in both length and girth. It was probably about the size of Mark's cock, so it's not like I hadn't fit something that size into my ass before, but it had already been loosened up at that point. The one that was supposed to go into my pussy was huge, at least ten inches long and thick enough around that I was pretty sure my fingers would barely be able to encircle it. It was the big, thick one that I'd seen attached to the machine the first time I'd ventured into Mark's basement. Immediately I shook my head. "There is no way those things are going to fit inside me Mark, are you crazy?" He just laughed at me. "You had something that size in your ass last week. You can take your time getting on them, I'll enjoy watching." I glanced over to see him leering at me and rubbing the bulge of his cock through his pants. Asshole. As much as I wasn't crazy about the idea, part of me was still curious. Would they fit? What would it feel like to try to make them? And why did I always have to be so damn curious?! It was this same insane curiosity that got me into this fix in the first place - I just HAD to know what it was like to ride a Sybian. My damn teenage hormones were not the most reliable life-guides. I stripped down, pretty used to this part of the program by now. Giving Mark one last pleading look before I tried to put myself on the Sybian, I begged him with my eyes to reconsider the size of the dildos. But he just smirked and pointed at the machine. When I straddled the Sybian, my legs spread wide and my pussy lips split open, I'm sure he could see that I was wet, no matter how much I'd been protesting. The lubricated lengths of rubber pointed straight up at my vulnerable body, just waiting to impale me on their thick lengths. Biting my lower lip, I bent my knees and positioned myself over the longer, thicker one. It felt like a baseball bat was trying to shove into my pussy. I groaned as the tip nudged in, but it flared fat and wide pretty quickly and I could feel my tight tunnel protesting the size. It was the biggest thing I'd ever tried to put into my pussy. Breathing deeply, I let gravity do some of the work, the cool length warming up as it was taken into my hot, wet pussy. The slick lube helped as my inner muscles spasmed and strained. I groaned. I felt so full already and the second dick was barely nudging my asshole, which mean that I had a lot more fake cock to go. And my thighs were already burning. I looked up pleadingly at Mark. "Help... please..." Grinning widely, he stepped forward and held out his arms so that I could grip right below his elbows as he cupped mine, holding the entire length of my forearms so that he could bear some of my weight. I shuddered and moaned as the tip of the second dildo slickly nosed into my asshole. I'd kept my backdoor stretched with all my masturbating, but my pussy had never been this full while I was trying to fit something else back there. And since Mark's cock, I hadn't had anything as big as the dildo I was trying to sink down onto. "Fuck, fuck, fuck," I muttered, groaning as the burning ring of my anus stretched and struggled. If it wasn't for Mark holding me up, I would have never been able to maintain my position at this angle, and it made me feel even more vulnerable. All he had to do was let me drop and I'd be fully and painfully impaled. More painfully, that is. I could feel sweat breaking out on my forehead as I bounced up and down slightly, working more of the cocks into my unhappy body. It was exciting, but it hurt too, and not entirely in a good way. I whimpered as Mark made soothing, encouraging noises at me. The huge bulge at the front of his pants said that he was enjoying my distress. Or maybe he just liked the way I was clinging to him as my body was invaded by giant dildos. I know my breasts jiggled enticingly every time I bounced, but it's not like he could touch them while he was supporting my weight. It took a while for me to seat myself completely on the cocks, both of my holes were throbbing by the time I managed to fit them entirely in me. I felt like my lungs had had all the air pushed out of them, as if the dicks were so big that they didn't leave room for my internal organs. Both holes spasmed and clenched, my legs were already quivering from the strenuous effort involved in seating myself on them. I was incredibly full. Stuffed. Bloated. And I looked up, with almost dread in my eyes, to see Mark pushing the button. OH FUCK. The large size of the cocks made the sensations that much more intense, that much more severe, against the spasming walls of my body. I shrieked as the dildos spun inside me, thrusting and fucking me. Even though my legs were tired, I found myself bouncing on them, my pussy creaming hard as it was stimulated from my clit and pussy lips all the way to my cervix. The fat cock pushed against the end of my tunnel with every thrust and it hurt so good. The strain of being so fully stretched was becoming less and less painful as pleasure took over, I moaned and rubbed my pussy lips and clit against the vibrating hump, starting to really get into the new sensations. My lower body felt like it was overheating from all the friction and fullness, but I didn't care... it felt incredible. I could already feel the most amazing orgasm beginning to build deep in my core, tightening my nerves around it like thread around a spindle. Mark had his cock out and was steadily stroking it, watching me as I began to moan and ride with a lot more enthusiasm, my body finally accustomed to the size of the cocks that were fucking me. And they felt really, really good. I would have never chosen to stuff myself as full as he had, but now that I was experiencing it, I was learning that I could not only take it, I could probably come to love it. I threw back my head, riding with abandon, fucking myself with the machine and glorying in it. I knew I would probably have to pay at the end of the ride, that tomorrow was going to be even worse, but while I was fucking the Sybian, I was in the moment. I was buzzing with pleasure. And I wasn't thinking about the future, I was just enjoying the now. I screamed with ecstasy as my orgasm exploded inside of me, deep in my pussy and humming outwards through the rest of my body. I'd become so used to the curling, intense orgasms that I ground myself down against the machine, milking it for more and more pleasure. It was a full body climax, deliciously decadent. So when the movement and the vibrations came to a sudden halt, I was more than a little surprised. And upset. "What happened?" I asked, gasping a bit with the breathlessness that came from a sudden shock. The lack of stimulation hadn't interrupted my orgasm, but I was used to more... my body wanted more, craved more. It was like getting a taste of the most incredible food imaginable, and then having it taken away. Mark smirked at me, still stroking his cock. "I just wanted to give you a little ride, I told you. Get you prepped for tomorrow." "Please Mark, please let me keep going," I begged, my pussy and ass clenching down around the dildos as if trying to cling to them. I wasn't nearly senseless enough to give into whatever perverted things he might want to do to me and I definitely wouldn't be able to calm down and fall asleep now if I didn't get off again... possibly several more times. "You're going to be sore tomorrow..." he said, looking reluctant, but there was just a hint of acceptance in his voice and I latched onto that hopefully. "Please... please Mark, I promise I'll be good at the party." He studied me, a small little smile curving his lips. "Okay Annie, but you're going to do something else for me tonight." I wanted to ask what, but he was already pushing the button and the Sybian was starting up again. On a slower speed, with lower vibrations, but it was enough to stop my speech and make me moan. I was barely aware of Mark setting something in place in front of the Sybian until he was suddenly right in front of me, his cock pointing at my face and I realized that he'd put some kind of platform down so that he could get his dick to the same height as my mouth. When he grabbed me by my hair and pulled my head forward, his hips thrusting at the same time, I gasped and my hands came up to push against his hips. But he didn't care; my arms were weaker than his and he had a hell of a lot more leverage. Besides which, I was incredibly distracted by the pleasure that was building up inside me again. The bitter, salty taste of his pre-cum filled my mouth, the heavy, musky flavor of man right behind it. Dicks have a certain flavor, meaty and hot. I didn't have a lot of experience at sucking cock, but that didn't seem to matter to Mark. He just ignored my shoving hands, my unhappy gurgles, and started fucking my face while I was riding the Sybian. I had a sudden flash of imagery, one of the dirty stories I'd read recently, about a girl who fucked three guys all at the same time. She'd been filled up just like I was now, even though two of the cocks in me were fake. I didn't know how many friends Mark was having over tomorrow, but I couldn't help but wonder if I was getting a preview about what might happen. The Sybian's movements kicked up a gear as Mark's hands moved in my hair, and I realized he was still holding onto the remote. Using it to control the machine even as he controlled my head, forcing his cock deeper into my mouth. I gagged and choked a bit, my muffled protests humming along his cock even as the machine's vibrations hummed through my body. I clung to his hips, using them to hold me up even as I tried to push him away. The lack of air was somehow making everything feel more intense, my head felt floaty and light and my skin tingled. I sucked in air when I could, getting just enough to keep me from completely panicking. As the Sybian's relentless fucking began to pound into me, moving back into high gear, Mark's thrusts became rougher and harder. I was moaning around his cock, my breasts jiggling, my body bent slightly forward as he fucked my face, which made the movements of the Sybian feel even more different. Completely filled, already sensitive from my first orgasm, my next one building as the machine had slowly worked its way back to full force... When I came again, it was with Mark's cock thrusting into my throat. He shoved deep, groaning as my scream vibrated around his cock, the muscles of my throat pulsing and massaging the tip of his dick. I was barely aware of my dwindling supply of air as the waves of ecstasy battered me, rocking me on my seat, filling me up with the most incredible pleasure so that everything else dimmed and fell away. I kept riding, kept moaning, lifting myself up slightly to give my clit a break from the intense vibrations, although allowing the cocks to continue to pummel my insides. Mark ignored my own movements, continuing to fuck my face with long, hard strokes. Tears rolled down my cheeks as I tried to push him away again, slightly more back in control of myself, but my efforts were pointless. He pushed me back down, almost as if in retaliation, and it felt like my clit was exploding against the Sybian as the little pleasure nub was wedged tightly between my body and the machine. I screamed again, this time tears rolled down my cheeks at the intense sensations, and Mark shoved deep into my throat again. I could hear his shout of pleasure above the roaring in my ears, and then thick, hot fluid was pouring down my throat. I swallowed automatically, my throat muscles working involuntarily to keep me from trying to breathe in the deluge. My own body was wracked with sexual pleasure, rocking and writhing as it became too intense to bear... something I was familiar with from my previous rides. I was struggling to be let up and off now as much as I was to get Mark's cock out of my mouth. The softening dick pulled away and I gasped for air, hanging onto his hips so that I could pull myself off the machine at the same time. I was nearly halfway off when he must have pushed the button to stop it completely, because the movements suddenly ground to a halt. I moaned as my pussy and ass pulled free with small sucking sounds. I could feel the holes gaping between my legs and I shuddered to think what they might look like. "Ready for bed?" asked Mark. I nodded weakly. "Good, because you're going to need your rest for tomorrow." I just nodded again. I was worn out, although not as bad as the last time I'd ridden the Sybian. I put on my own clothes and leaned on his arm to get upstairs. I shut the door behind me when I got to the guest room, shutting him out, basking in the afterglow of my ride and trying to ignore the taste in my mouth. I crawled under the covers, still fully clothed and fell asleep. I'd deal with tomorrow when it got here. Annie Rides the Sybian Ch. 05 I woke up pretty late to a knock on my door. It took me a minute to remember where I was and why my muscles felt so sore. I groaned as I made myself sit up, wincing as my sore pussy and bottom hole protested. Now I kind of wished that I'd taken Mark's advice and just gotten off the Sybian after one orgasm. The idea of riding it again made all my inner muscles twinge. Even though I'd gotten used to riding it on a daily basis while I'd been house-sitting for him, I'd never used more than one dildo and even that one dildo had never reached the size of the one Mark had forced into my pussy last night. My asshole felt especially unhappy. Another knock reminded me of why I'd woken up. "Yeah?" I said sleepily, hoping that my appearance and morning breath would put off anything dirty that Mark might want to do. I was still in my clothes from the night before, my hair felt like mess of tangles and the taste inside my mouth was foul. Normally I wouldn't want anyone to see me like this, but since it was Mark I was okay with whatever protection I could drum up. The door opened and Mark entered with a trap. My stomach lurched as the smell of sausages, eggs and toast filled the room. I was starving. Not too surprisingly considering my activities the night before. "Thought you might want some breakfast, sleepy-head." I didn't respond. I'm not a morning person anyway and I resented his patronizing tone considering that he was the reason I'd slept in so late. But when he put the tray down on my lap, my ingrained good manners forced a response. "Thank you." "No problem. The bathroom's all yours if you want to take a bath. I've got some work to do, so I'll be in my office." "Okay." I was too busy digging into the food to care much about what he was saying, other than a sense of relief that I wasn't going to be expected to perform any time soon. Apparently satisfied with my response, Mark left the room. Which was a relief. I didn't really feel like having him watch me eat and I definitely didn't feel like trying to interact with him right now. Although, after a few minutes, when my stomach had stopped griping about how hungry it was, a bath sounded amazing. I could do with a good long soak. I ate the rest of my breakfast and headed straight to the bathroom. The shower curtain was already pulled back and there was a bottle of bubble bath sitting on the ledge of the tub. Heck yes! I brushed my teeth and went to the bathroom while the tub was filling. My pussy and ass were definitely sore and I eyed the bubbles that were rising in the tub with relief. The bubble bath bottle said that it was soothing to tired muscles and boy did I need that! Lowering myself into the hot water, I moaned and then hissed as the hot water stung my poor anus and pussy. But it only stung for a moment and then it started to feel amazing. I sank down up to my neck, resting my head on the back ledge, and sighed with something very close to happiness. Did the situation I was in suck? Yeah sure. But I was enjoying some parts of it and if I was going to make the best of my situation, then this was definitely one of the good parts. ****** By the time Mark's doorbell rang, I was more than just a little nervous. It was 8pm. We'd had dinner at 5, early enough for me to digest... and then an hour ago he'd given me an enema to use on myself. One of those little syringe type things. It wasn't as unpleasant as I'd thought it would be, in fact it was kind of nice. Probably helped by the fact that Mark hadn't had an interest in watching me use it. Once I was all freshly cleaned out, he had me put on my little schoolgirl outfit. No underwear underneath. The short skirt barely covered my pussy and butt - in fact I'm pretty sure the curves of my cheeks were peeking out the bottom even when I was standing upright - and the dark pink of my nipples was clearly visible through the thin fabric of the shirt. It wasn't exactly an expensive shirt either, so the material was kind of rough and the constant rubbing made my nipples stand at attention. I caught a glimpse of myself in the mirror and flushed with shame as I realized that I looked like a complete slut. The costume was even tighter and shorter than it had been on me when I'd first bought it, and it hadn't exactly been modest then - and I'd been wearing short shorts and a bra underneath before. "Perfect," Mark had said, once I'd finished putting my hair into pigtails. That was his word for it. Mine would have been something very different. But now his doorbell was ringing and I felt absolutely frozen in place in his living room. Waiting on my doom. My pussy was shockingly already ready to go again, it knew it was going to get another ride tonight. My asshole felt a lot more tender than my pussy, but even so I was already getting kind of creamy and hot under my skirt. The fantasy of riding the Sybian while being watched by faceless men was a lot more scary when the men were about to get faces. And hands. When Mark came back into the living room he was followed by three guys. "Annie, this is Darryl, Howard and George. Guys, this is Annie, tonight's star attraction." All three of them gawked at me, looking me up and down, and I could see the bulges appearing at the front of their pants. I blushed deep red and tugged at the hem of my skirt, not like it was going to cover me any more than the short length already was, but it was an instinctive reaction. Despite the situation, I couldn't help but feel a little spurt of excitement. Mark's friends were pretty attractive, even if I wasn't super attractive to them. At least they weren't UNattractive. Darryl was probably the hottest, he had creamy chocolate skin, the color of a milk chocolate Hershey's bar, and he was tall and physically fit. Not overly so, but it was obvious that he kept himself in shape. His head was completely shaved, and he had a pretty nice head shape. I hate the completely shaved look though, it's kind of creepy to me, I prefer just a little bit of hair or fuzz or something... George was a ginger, with long, floppy red hair that had just a bit of a wave to it. And some freckles. He was kind of boyishly cute, and I had a feeling that he was older than he looked - because he looked like he was in his early twenties. Howard was the least attractive. His facial features kind looked like he'd gotten into some fights in his younger years and he was more than just 'physically fit.' Like, it looked like his muscles had muscles. If he was shorter, he would have looked like a small tank. I get that some girls really like the super muscle look, but I'm not one of them - I thought Darryl was a lot more attractive with his sleeker, leaner muscles. "Shit..." George said, finally breaking the silence. "Are you sure she's eighteen, Mark?" I found myself straightening up. Dammit, I know the school girl outfit didn't help, but at that point I was at the age where I wanted to be recognized as an adult! Of course, the moment my indignation showed, I realized that I might have been better off trying to convince them that I was underage. But they'd all seen my reaction, even before Mark reassured them. After that they wasted no time getting me downstairs, where they all got to see my reaction as I gasped and spun around to Mark. "Mark... no please, I can't take that..." He'd replaced the anal dildo from last night with the gigantic one I'd first seen on the Sybian; it was just as big as the one going in my pussy. "Of course you can, you took one nearly as big last night, and you've had my cock in your ass before," he said, brushing off my concerns as he grabbed my hand and pulled me over to the Sybian. I went reluctantly, wondering what they would all do if I kicked up a fuss... going by the way they were rubbing their obvious erections, I didn't think they would be any more sympathetic than Mark. Mark gave me a considering look once we got over to the Sybian. "I think this might be easier for you with a blindfold." I shivered, but didn't protest. Shutting all the men out seemed like a better idea than having to watch them watch me. I'd still know they were there, but it would help me if I couldn't actually SEE them. So I didn't protest as he put a blindfold over my eyes, one of those sleeper ones designed to shut out light. It even had a little bit of padding to keep me from being able to peek through the bottom. "Can you see anything?" "No -OW! What the fuck?" I jerked back, one of them had pinched my nipple rather roughly. The little bud throbbed, fully hardened from that tiny bit of pain. Chuckles were all around me and I gulped, realizing that - for all intents and purposes - they had me surrounded. "She definitely can't see." "Here Annie, let us help you get undressed." I didn't protest - it would have been pointless anyway - and they already had their hands on me, unbuttoning my shirt, pulling down the zipper on my skirt, and every single one of them groping a feel. I wanted to moan, but I didn't want to encourage them... still, their hands felt good. Being blindfolded was even better because I could pretend that this was just a fantasy, just something that was happening to someone else. Hands squeezed my breasts as someone else's fingers pinched and tugged on my nipples, more hands were squeezing my thighs and buttocks. "Bend her over," I heard Mark say. "If she's so worried about her ass, we can open her up a little bit." "Let me," said another voice eagerly, I was pretty sure that it was George's. Boyish appearance notwithstanding, he was apparently really excited about the most forbidden of my holes. "Fuck these are pretty little tits." That was definitely Howard, his voice was rougher than the others. "Aren't they?" That must be Darryl, his voice was smooth and sexy, self-assured. Fingers slid down into my pussy, checking for dampness, and I heard him chuckle. "Fuck she's wet." His finger slid into my cunt, exploring, just as Howard - I was pretty sure it was Howard - twisted my nipples and I cried out, reaching up to grab his hands and try to pull them away. My pussy spasmed. "Do that again, I think she likes it," Darryl said, laughing, his finger moving back and forth inside of me. Of course his finger wasn't as big as a cock, but it was still disconcerting because I knew I was getting fingered by a guy I'd literally just met. And not one that I'd have touching me so intimately by choice. "Mark, get her hands for me." Almost immediately, my hands were pulled away from where I was trying to stop Howard, and were pulled behind me. The position thrust my breasts out, as if they were asking for more abuse. My nipples were throbbing and I tried to pull away, but Howard's fingers just pinched tighter, twisting and then tugging me down. I had to follow as he bent my body over using nothing but my nipples, leaving my ass completely vulnerable. Something small and slick poked at my asshole and then slid in, so that I had a finger in both my holes. Almost a miniature preview of what was to come. The fingers rooted around inside me as Howard continued to torture my nipples. I could only assume that it was George's finger in my ass, Mark's friends taking the opportunity to feel me up. I moaned as both of them pulled out enough to add another finger and then slid back in. It felt good. My asshole was stretched enough from the night before that there was almost no discomfort from this much smaller amount of stretching. Even when he added a third finger, I just squirmed and moaned a bit. As the men fingered me forcefully, Howard continued to torture my sore nipples. "Please stop," I begged. "Just put me on the Sybian." All of the men chuckled. "Eager little slut, isn't she?" Howard asked, giving my nipples a bit of a rest as he cupped my breasts and squeezed them hard. "She's a completely slut for the Sybian," Mark said, satisfaction threaded through his tone. I bristled a bit, but I didn't really have a response to that. And I'd much rather be on the Sybian than at the mercy of their groping hands. "Alright then, let's watch her." That was George, sounding just as eager as he had to put his fingers in my ass. As if to punctuate his words, those fingers twisted and spread inside me and I whined a little. Finally they all pulled away. Two men took my arms, I wasn't sure who, and helped me blindly straddle the Sybian. "Hold onto her, she's going to need some help going down," Mark said from in front of me, so I knew it wasn't him on either of my arms. Someone grabbed my butt cheeks and spread them, not that they really needed it, but it added to the vulnerability of my situation. I could feel the tips of the dildos pressing against my holes simultaneously, my asshole feeling especially exposed because of the way my cheeks were opened by whoever was holding them. I whimpered as the men lowered me, pushing me down onto the impaling rubber rods. My ass strained and protested, feeling even more tender than last night, although being stretched out by George's fingers had probably helped a lot... so it could have been worse. My pussy was creaming, excited, eager. I could feel hot breath on the shell on my ear just before one of them spoke. "Does it hurt Annie?" It was Howard, his voice excited and rough. "Can you feel the cocks splitting you open? You gonna squirm for us?" I was already squirming and I bit my lip to keep from whimpering. I hated that his words kind of turned me on. "Ouch, slower!" They were pushing me down much faster than I would have gone myself and I pressed upwards with my feet, struggling against them. "You're okay, pretty girl," that was Darryl. I would have protested but then somebody was cupping my mound, rubbing my clit and I spasmed from the sensation. I had a feeling it was Darryl, trying to help me out, and it did help a bit, the pleasant sensation battling the burning discomfort of my ass and pussy as the cocks battled for space inside me. The anal dildo wasn't thicker than the one I'd had in last night, but my anus was already sore and the depths of my tunnel felt a little bruised because last night's cock had gone so much deeper than ever before. A depth that was only be surpassed now. My back arched and if it wasn't for the men on either side of me, who were simultaneously holding me up and pushing me down, I would have probably have never made it. My thighs were burning, even with their help, because it had taken so long for me to work my way down the twin pole. I was gasping for breath, feeling like my lungs had constricted due to lack of space in my body, and I clutched at their hands as I finally settled. "Fuck... oh fuck..." "Goddamn that's hot," George said as he released my ass cheeks. "Here, put these on her, they'll give her something else to think about." I whimpered and tried to jerk away as I felt someone cup my breast, instinctively knowing what that soft mound of flesh was being held for. My poor nipple, already abused by Howard's sadistic torture, flared with pain as something cold and hard clamped around it. I could feel the cool brush of a chain against my stomach before they attached the other one. Air whistled through my nostrils as my body struggled with these new sensations, but the pain in my nipples did help to distract from the aches and discomfort in my lower body, as well as making me more excited, so I didn't try to take them off even though they hurt. "Here, attach this to the chain..." My nipples were tugged a bit and I leaned forward to lessen the pain... only to find that they'd done something and now I couldn't lean away without my nipples being tugged painfully. "No!" This time I did try to reach to take them off, but they caught my hands before they'd even made it to my breasts. "Got anything to secure her with?" Howard asked, his voice almost casual. I immediately knew that he was the one holding my hands, pulling them above my head so that I couldn't do more than squirm a bit since the chain on my nipple clamps kept me from trying to slide off of the cocks. With all those beefy muscles, I had no hope of getting my wrists free from his hands and I knew it. Every jerk of my arms made my nipples pull and throb. Basically it was a no-win situation. They put what felt like some kind of leather cuffs around my wrists and kept them right where they were, high in the air. I could only imagine what I must look like with my thighs spread wide over the machine, my red nipples clamped and chained to hold me down on the Sybian, and my wrists high in the air above me, leaving me completely vulnerable. It was like something out of my worst nightmare - or my most erotic fantasy - and I couldn't decide which. Then the Sybian jerked to life inside me. I cried out, my holes spasming... it had been a long time since I'd ridden the Sybian two days in a row, and I'd never done so with an anal dildo. I tried to lift off of them, without thinking, and shrieked as my nipples pulled painfully. They throbbed and I squirmed, panting with the crossing sensations that sizzled through me, crackling along my nerves. "Oh fuck..." I couldn't move up and down much on the machine, because of the clamps on my nipples, and so my vulva and clit were pressed against the vibrating hump even more than usual. The buzzing vibrations were intensely focused and there was no escape from them, barely any relief, because my legs couldn't hold me up at that angle for more than a second. I could hear male groans and heavy breathing around me and I knew that the men were masturbating, jerking off as they watched my helpless body riding the Sybian. With the blindfold on, that was actually pretty hot, because I could pretend that they were completely faceless. Although most of my focus was on the machine, the circling cocks inside my body, their pumping thrusts, and the heavy vibrations of the Sybian itself. I was soaring higher and higher, my thighs clamping down around the machine as my back arched, thrusting my breasts out in front of me. My nipples were throbbing in time with my racing pulse, the pain from the clamps beginning to feel remarkably good. When the first orgasm rushed over me, I cried out, shaking and writhing on top of the Sybian so that lightening strikes of pain in my nipples lanced through the ecstasy. My holes squeezed down on the dildos, trying to halt their relentless spinning thrusts, to no avail. Thrashing, I felt another wave of rapture hum through me, little fireworks exploding along my skin. I screamed and tried to surge upwards as the vibrations became too intense on my clit, only to scream again as my nipples stretched painfully. "Make it stop! Make it stop, make it stop!" Tears leaked into my blindfold as I began to struggle, desperately needing to pull away and yet unable to without feeling like my nipples were being yanked off. "Let's take her off." Who'd have ever thought I'd be grateful for overmuscled, sadistic Howard? Then the bastard pulled off my blindfold and grinned at me as he released both of the nipple clamps. At the same time. Tears streamed down my face as I was wracked with the throes of another painful orgasm, my fingers clutching at the chain hanging down from the ceiling attached to my wrist restraints as I pulled myself straight up. It was self-preservation. My swollen, red pussy throbbed and my anus gaped as I stood there, legs quivering, my arms tucked over my nipples as I pressed them into my chest, trying to soothe the sharp pain that had assaulted them as the blood went pouring back into my poor little nubs. I felt about ready to fall over. Mark grabbed me around the waist and released the chain from my restraints, although he kept the wrist cuffs on and attached together. I moaned, leaning into him, my body still sensitive and humming from the orgasms. The machine had ground to a halt and the cocks were sticking up obscenely, slick and covered in my juices. Annie Rides the Sybian Ch. 05 I almost didn't notice, until we were about a foot away, that Mark wasn't leading me towards the stairs, he was leading me towards a padded bench that Darryl was laying on! He looked like a human Sybian, with his cock sticking straight up in the air. "Oh please, nooooo..." It hadn't even occurred to me to wonder whether or not any of them had cum while I was riding the Sybian. "Quiet Annie, or I'll give you something to fill your mouth," Mark whispered harshly in my ear. I whimpered, unsure of whether he meant his cock or one of the many ball gags that I knew were available in the room. "Fuck look at how her ass is gaping," George said behind me, in an awed voice, as Mark forced me to straddle Darryl and sink down onto his cock. It was about the same size as the Sybian dildos, but without the vibrations, so even though I was sore, it wasn't nearly as torturous as the machine could be. He was hot and hard inside of me, that little difference between a fake cock and a real cock completely tangible. I was kind of thankful that he was the one I was the most attracted to, since I was going to have to look at him. A hand on my back pressed me down so that I was leaning forward and the fat tip of a cock pressed against my anus. I cried out as I was impaled on two real cocks. I can't exactly describe how it was different from being on the Sybian, but it was. Maybe it was just the hot man flesh on either side of me, or the heat of them inside me, or even just a perception thing, but it was different. "Oh fuck, she's so hot," George groaned in my ear. I wasn't all that surprised that he was the first one to claim my ass tonight, he'd already shown he was pretty obsessed with it. Both he and Darryl moved, the bench allowing Darryl to get more leverage than a guy on bottom can usually manage. Just like with the Sybian, I was just along for the ride. It was completely different from the machine though, not nearly as rhythmic, no circling, no vibrating, but that also meant that it gave me some recovery time. Even though I could feel my pleasure building, it wasn't the same kind of train wreck orgasm that the Sybian usually caused, but a longer, slower, hotter build to a shuddering, screaming climax. They fucked me hard, pistoning in and out of me, and when I came I could feel them cumming too, filling me up with jizz. I collapsed on top of Darryl's chest, utterly wrung out, my holes spasming uncontrollably as their cocks softened. And then I realized. "OH my god..." I pushed up from Darryl's chest, panic giving me strength that I wouldn't have ordinarily had. "Oh my god... you didn't wear a condom! "Relax," Mark said soothingly as George's cock slipped from my ass, helping me to stand. "Darryl and Howard have both had vasectomies, that's why they get your pussy. And we're all clean." "Oh..." Thank god... I felt a strange surge of gratitude. Mark was a strangely considerate blackmailer-rapist at times. Waiting till my parents were out of town. Not impregnating me. Reassuring me about STDs. That surge of gratitude died the moment Howard took Darryl's place on the bench, his massive cock pointing straight up. I had assumed he'd have a small dick, I don't know why, maybe it was all the muscles and subconsciously I'd decided that he was compensating for something. I was so far from the truth, it wasn't even funny. It was the biggest cock I've ever seen - to this day far in the future he remains the biggest - and he was even larger than the Sybian dildos. Both longer and wider. I didn't want that thing anywhere near me, much less in me. "No... no, no, no, no, no..." Mark ignored me, pushing me forward to straddle Howard, who grinned up at me. "Ready to take a real man, sweetheart?" "No..." I whimpered, putting my hands on his chest, trying to keep them from being able to push me down. But my weak muscles were never going to do the trick. My battered pussy ached as it was forced wide open, stretching around his baseball club of a cock and I struggled and wriggled, panting like I was running a marathon as I slowly but surely slid down onto it. The jizz already filling my pussy and all my cream from the Sybian definitely helped, otherwise I don't know if Howard's cock would have ever fit inside me. I could feel the tip of him painfully nudging into my womb. Thank GOD he'd had a vasectomy or I'd have been impregnated for sure. They gave me a minute or two to get used to him, my pussy squeezing, his cock jerking, but otherwise neither of us moving. I could hear George murmuring his awe that I'd take the whole thing. As Mark finally pushed me to lean over Howard's chest, despite my protests that there was no way he'd fit in my ass with my pussy already filled by Howard, the man beneath me chuckled. "Stop bitching Annie, just be glad I was willing to take your pussy and not your ass." The idea of Howard trying to fit that monster into my poor ass made me clench down immediately, nearly strangling Mark's cock. He didn't have more than the head worked into my body, and he groaned as I tightened down. Unfortunately I was too slick to stop him for long, and he worked his cock into me as Howard lay waiting beneath me. I flopped like a rag doll between them as they started thrusting, too exhausted to do anything but take their rough fucking as I moaned over and over again. My pussy was so swollen and sore, and my clit felt like it was being abraded by sandpaper as Howard's pelvis ground against it. And even that didn't stop the waves of pleasure that eventually ran over me, my body too confused by the varying amounts of pain and pleasure, mistaking the battering of my holes as a reason to orgasm. I didn't scream, I just whimpered and sobbed as the ecstasy ran over and through me, ignored by the men who were pounding away at my body, involved in their own pleasure. When they came, I could feel the liquid filling me up, joining the loads that George and Darryl had already dropped in me. The men were panting on either side of me, sated from using my body. Out of the corner of my eye, I could see Darryl and George, watching and still enjoying. George was already hard again and lazily stroking his cock, Darryl was half hard but he was fondling his balls. I whimpered and closed my eyes. I was so not going to last if they all wanted to fuck me again. Somehow, I think I must've been going in and out of it a little bit, I ended up across Howard's lap on the bench, so that I wasn't hanging over his lap but just had my pelvis over it. He fondled my ass while Mark held a cup of water with a straw for me to drink. The water was only a little cool, but I think that was better anyway, cold water would have just sat like a block in my stomach. The men were all talking and joking, mostly about people they knew, so I just kind of tuned them out while I recovered. I don't know how long I was across Howard's lap while he groped my ass, but eventually they lifted me up. I went with them willingly enough until I realized they were leading me back over to the Sybian. The anal dildo had been replaced with the smaller one from last night, but I still didn't want to get back onto the machine. "Nooooooo please, don't make me..." I begged. I cried. They ignored me and spread my legs, pushing me down onto the fake cocks. I could feel their cum sloppily gushing around inside me as the cocks filled me. All of them were looking at me with hot, hungry eyes, their cocks fully hardened again. Later I realized they hadn't been waiting for me to recover, they'd been waiting for themselves to. They attached my wrists to the chain overhead again, forcing my breasts out. This time they didn't blindfold me so I could see them staring at my dark red nipples, which still hadn't regained their usual color. I was fully impaled, my holes clenching, although at least the machine hadn't started up yet. Then Mark and Howard, who I had realized were basically the ringleaders, put leather cuffs around my thighs and attached those to the floor, tightening the leashes on them so that there was no way I was going to be getting off the Sybian until they released me. "Oh no, please, I'll fuck you, all of you, however much you want, oh my god, please don't," I babbled everything I could think of, all sorts of useless promises as they stepped back and looked at their set-up happily. Tears, this time of frustration, were sliding down my cheeks as Mark grinned at me and pushed the button. The cocks inside me starting to move, slowly, thrusting up and coming back down, fucking me. But not spinning yet. I squirmed, biting my lip, glaring at them as much as I could while the cock tormented me. My pussy lips were fully splayed and pressed against the seat of the Sybian, still coated with their cum, and my swollen clit was the same. I shuddered and arched as the cocks picked up speed and I felt the lowest hum of vibration go through the machine. "Mark pleeeeeeeeeeeeease..." He just shook his head and kicked the machine up again. The vibrations intensified and I tried to lift myself up, but the restraints on my thighs held me firmly in place. They were sexually torturing me without even touching me. I sobbed, trying to lean back, but I wasn't able to with the giant cocks in me; it just made my anus tingle with the vibrations as well. When the cocks began to spin and the vibrations went up again, I cried out and started begging again. I could see them fisting their cocks, masturbating as they watched me beg and scream, knowing that they were going to see me orgasm soon. "Oooooooo noooooooooooo..." The vibrations hummed so loudly I could feel it all the way to my ear drums and I screamed like a banshee, my sore throat aching, as I came again. It was too much. The heat, the thrusting, the pleasure, the pain... and I couldn't get away from any of it. I was strapped in, forcibly held to the Sybian as it fucked me and pleasured me beyond what any sane person would desire. I screamed and pleaded and sobbed, my body shaking as I shook with the force of the convulsions. There was no relief from the painful ecstasy, no way to pull my poor pussy off of the terrible device, although my thighs strained against the restraints. A strange roaring filled my ears and my head hung back as I writhed and sobbed. Heat scalded me, and I didn't even realize that the lava pouring down my breasts was actually somebody's cum, I was too far gone in my haze of intensely torturous rapture. Hot liquid poured on me from every side, coating my breasts, my sides, my ass, dripping down me and creating new sensations along my sensitive skin. I don't know how long they left me there, how long it took all of them to cum on my writhing body. I was almost completely out of it when the machine finally stopped and they took me down. I remember being in the shower with someone - Mark I think, cleaning me off, and that was it until I woke up the next morning. As usual, I snuck out of Mark's house. I didn't see any of them again before I left for college. While I was away, Mark moved. I don't know where. I sometimes wonder if the reason he finally blackmailed me was because he knew he'd be leaving soon and would soon lose the chance. He did send me a still picture of me on the Sybian. I have no idea what night, because I can't tell how many cocks are inside me. I know it's not from either of the times I wore clamps, but it might have been from that first week I rode it or from one of the times he was there watching. My head is thrown back in ecstasy, the look on my face is one of pure bliss, my breasts are thrust out, and my back arched. I look incredibly sexy. My life after that was completely changed. I had all sorts of adventures in college, mostly with older men. The day after I graduated college, I ran into Howard again and that definitely got interesting. The day I met the man I eventually married, who also wanted to watch me ride his Sybian - and as many of his fucking machines that I was willing to try out. But those are other stories. This was the story of how I first rode the Sybian, because this was the first story, the story that changed my life. Sometimes I wonder if Mark ever thinks about me, or if he's found other young women to ride his Sybian, but mostly I think back to that summer, and as insane as some of my memories are, I don't think I'd change a single one.