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.