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.