The numbers were rising quickly, as Brooke’s fans bid up her use of my ass. Their arousal seemed to mirror Brooke’s own, and as her cock got harder and harder in the grip of my stroking hand, the chime of tips coming in kept sounding. 

It wasn’t long before the first milestone was reached, and Brooke started applauding. 

“Oh baby, it’s time, Crissy. Stop stroking me for now, and stand up and lift up your skirt. Show our friends how you are prepared.”

I released her warm hard shaft and I stood up. I was a bit unsteady on my heels for a moment but once I righted myself, I looked at the screen to make sure what they wanted to see was in view. I lifted up my dress enough to fully expose the panties I was wearing and I started to spin slowly. As the comments kept coming in, it was clear I was not the only one who had noticed the wet stain of leaking precum I’d left in them. 

“Take them off, Crissy, nice and slow.  Show your friends your little clitty cage, and the plug you’ve gone in, getting your pussy ready for use.”

My face was not in the shot for these few moments, as I hooked my thumbs into the waistband of my panties and tugged them down. I stepped out of them and lifted my dress again, turning slowly. There on the screen, broadcast to anyone, was the image of my humble clitty in its cage, and my ass cheeks tight around the base of the plug inside me. 

“Come over here, Crissy. Kneel on all fours on the sofa.”

I obeyed, and Brooke adjusted the camera so that it gave a kind of three-quarters view of me from the side and behind. I had to look back over my shoulder to see it 

Once she was satisfied with the pose and the camera’s view of me, Brooke found a place behind me and she started to tease and ease the plug out of me. She didn’t rush and she was playful about it, pulling it out a bit and then holding it there, before letting go and feeling my body suck it back in, giggle all the while.

“Oh, look at how hungry Crissy’s pussy is!” she exclaimed to her fans. 

Finally she tugged the thing out, leaving me feeling wide open and empty. That feeling didn’t last long, of course, as Brooke was right there with the first dildo, lubricated and ready. It was a moulded, realistic-looking cock and balls type, albeit a rather large member, and I moaned softly as I felt the head of it pressed to my rosebed and then inside me. 

Brooke started to fuck me with it, every so slowly. As the rubber cock pushed in and out of me, I felt my chastity cage start to feel very tight. 

To go along with my soft moans, Brooke gave the viewers a running commentary. She talked about how tight I was, how it sounded to have me moan with pleasure, and she could see my trapped sissy clit swelling up behind its bars. 

Once I began leaking in earnest, with long slow strings of precum visibly falling from me, she made sure to highlight that as well. She even lifted the camera in for a closer look for a few moments. 

“Come on, Crissy. Show me how hungry you are for cock in your pussy. Rock back against it. Fuck it for us, baby!”

I obeyed out of submission and out of lust. I started rocking back and forth on all fours, matching her rhythm as she drove the toy into me. I was aching and leaking, and my body’s frustrated attempt at erection was growing painful. The pain was equally matched by how good even the denied attempt at physical arousal felt, however, and I just kept grinding back onto the phallus. 

In the background of it all were the chimes of the tips coming in and Brooke’s gleeful voice encouraging me and narrating to her viewers. The sensations inside me were intense and confusing and overwhelming. The awareness of an audience, not just taking part and guiding me, as Brooke was doing, but also the number of faceless and nameless viewers, cheering me on as well, made my mind melt even more fully. 

I felt like I was on the edge of orgasm when Brooke’s hand on my ass stopped my motion. She pulled the dildo from me, leaving me empty and denied once more. I moaned out loud and I felt like I might cry. 

“Very good job, Crissy. I think we all had a lot of fun… but it’s time to move on to our next toy!”

I knelt there, trying to calm down, as Brooke tossed the spent dildo aside and lifted the next one from the table. It was still somewhat cock-shaped but it was noticeably larger and it seemed to have the texture of an oversized screw, with ribs spiralling around its shaft. 

Rather than fill me with it immediately, she brought it close to my face first. I thought that she just wanted me to have a good look at it, but there was more.

“Kiss it, Crissy. Show us all how much you’re going to love feeling this pretty toy fuck your sissy pussy!”

I glanced at the camera for a split second and then accepted my fate. I leaned forward, pursed my lips, and kissed the bulbous head of the brightly coloured toy. She kept pushing it forward, so I opened my mouth and took it inside. I kissed and worshipped the thing in an exaggerated fashion, wrapping my tongue around it and getting it wet all over with my saliva. 

Only then, with her own wickedness satisfied along with the gleeful comments online, did she move back behind me and drive the thing inside me. It made me ache and moan with its size and surprisingly affecting shape and patterning. The spiralling ribbing was a constant teasing sensation as the thing stretched and filled me. Brooke was railing me with it, building up her rhythm, fed by my own moans and gasps. 

I ached inside the cage, feeling myself pressed up against its metal bars. I was leaking constantly, with a gleaming trail of precum caught in the lights shining upon me. 

It just kept going and going. I felt the thing inside me, tormenting and teasing and using me. I felt like it was hitting parts of me that had never been hit before, and I could feel the arousal building from inside me. I felt so close to exploding, but somehow the way the experience built was so slow and controlled that I was kept just shy of release and relief. I felt desperate, ready to beg and plead for whatever it might take to push me over the edge. 

My balls felt so full, so tight, bobbing and bouncing under my tightly caged and dripping sissy clit. I felt like my mind would break, accompanied by that chiming sound of tips coming in online, from the unknown crowd of witnesses to my use and depravity. 

She stopped again and took the toy from me. Again I was left, panting and desperate and empty. I groaned out loud, much to Brooke’s enjoyment. 

“Oh, I think our Crissy is so close and so turned on. We knew she liked to be fucked, but I don’t know that we knew she liked it this much!” Brooke teased, speaking to her fans instead of me. 

“Do you need a little break, Crissy? Something to eat to keep your energy up?”

“Yes, Miss Brooke,” I say, catching my breath. “Crissy would like that very much.”

“And I know what you like to eat, more than anything, Crissy.”

She came up to me and lifted her skirt. Her cock had been tucked back into her panties, but she withdrew it once more, pushing it towards me with her hips. All I could use was my mouth, kneeling on all fours as I was. 

Her hips were in control, and she fed me slowly and deliberately, even though I could taste the precum of her arousal almost immediately. It was part of her skill, perhaps, at putting on shows like this. She used my mouth as a sleeve for her cock, rocking back and forth, as she grew harder and thicker on my tongue. 

My cock still leaked, as I rocked back and forth with her rhythmic dance. Now and then she would slip her cock all the way out of my mouth, sliding over my lips and face, showing the audience just how hard and stiff she was. Perhaps the way I drooled and moaned around her was not quite enough to get that message across to them. 

The taste of her on my tongue and the feel of her warm shaft inside my mouth was keeping me aroused. It wasn’t just something I was doing because I had to. I wanted her to fuck my mouth and I wanted her cum. I felt so hungry for her. 

It felt like I was sucking her for an hour or more. My lips felt swollen and used, and my desperation only grew. I was pushing myself onto her and feeling her push into my throat as the wet sounds filled the room. Finally I felt that tightness and then the spasm of her release. Finally I felt the spurt of warm salty cum filling my mouth and sliding down my throat. I slurped and sucked and moaned, my mouth full of her, until I had taken every drop. 

I could feel it slide down my throat and land in my belly, satisfying me. Brooke, however, had much more in mind for me yet. 

I was surprised when she chose to blindfold me, but there was evidently something she wished to surprise me with. I couldn’t see the screen, or anything else, but I did still hear the occasional tip coming in from Brooke’s fans. Perhaps they were amused by the sight of me, or they saw something else happening that I did not. 

Things were definitely happening. It sounded like Brooke was moving furniture and setting up a whole scene. Once she was ready, she guided me over to the side, away from the sofa we’d been on, and had me stand still again while she readjusted the camera and lights. 

With her work completed, she returned to me while giving a running commentary to her fans. I blinked as the blindfold came off, and then my eyes widened as I saw what had been set up. 

I saw the large pink dildo first, given how bright the colour was and its imposing size and shape. It was large, to be sure but the head was also swollen, as there was a similar swollen lump about halfway down the shaft. That was just the dildo. The frightening pat was that the dildo was mounted horizontally on the end of a metal pole, and the base of that pole was jutting out from a machine on a steel stand. 

Brooke guided me to it, and then had me kneel on all fours once again, my ass edging close to the end of the dildo. There were a set of steel cuffs welded into the nearest legs of the base, and she closed them around my ankles, trapping me in place. 

She moved around, making sure my dress was tucked up and out of the way, and then moved back to lubricate the dildo generously. 

“Ask me nicely, Crissy. Ask me to fuck your pussy with the nice machine.”

I looked up at her, seeing the camera behind her and my own feminised face in the computer monitor. 

“Please, Miss Brooke. Please, will you fuck Crissy’s sissy pussy with the fucking machine?” I heard my voice breaking as I spoke.

“Yes, Crissy. Yes, I will!”

She moved back, adjusting something, and I felt the rounded head of the dildo push against my rosebud. Then the thing started. I saw the controls in Brooke’s hand. It was so slow at first, just pushing itself into me, deeper and deeper. I felt it stretching me, and the mid-shaft bulge grinding inside me. She drizzled more lube over it as it slowly sped up. I started to moan softly. 

With the machine doing the fucking, Brooke was free to buzz about, touching me and stroking me and even giving me occasional kisses. She chatted with her fans, sometimes about what was happening to me, and other times it was just like she was catching up with old friends. 

Every thrust the machine made melted my mind a bit more. It was merciless and tireless. My cock was aching again, fighting the limits of the cage, and leaking constantly. My arousal built and intensified, making me yearn for orgasm. 

“I have another special surprise!” announced Brooke. “Not just for you lovely viewers, but for Crissy as well!”

She moved in front of me so I could see the width of her smile. 

“Do you like surprises, Crissy?”

“Y-- yess,” I panted. “Yes, Crissy likes surprises.”

“You’re going to love this one. Let me just go get the door.”

My mind, as much as was left of it, began to race. Terror rose inside me, right up until the moment Brooke returned with Liam. His smile was as wide as hers. 

“This is Crissy’s Master, everyone. He’s here to help us all get Crissy to the peak of her time with us!”

He smiled and waved, but turned his attention quickly to me. He ran his finger across my face and I felt warm under his gaze. He stood upright, opened his jeans and freed his impressive cock. He was already half hard, and he wasted no time in filling my mouth with his shaft. I moaned around him and began sucking eagerly. 

Brooke pushed the machine faster and soon I was bouncing between the cock pistoning inside my ass and Master’s flesh-and-blood shaft pushing into my throat. It just kept going and going, and soon my mouth was full of the taste of his precum. The fucking machine was pounding my ass and working my prostate, leaving me leaking and aching and desperately on edge. 

I was losing the ability to think or to focus. Brooke’s giggling voice was a blur and the sounds of the chiming computer made a kind of strange soundtrack to my use.

I could tell that Liam was getting close. His taste filled my mouth and he was thrusting with urgency. His voice had changed into a sexy growl.

“Crissy, you can’t have sex with your wife, but you’re so turned on for your Master. You can’t get hard for Cheryl but you’re dripping for me.”

The only noises I could make were the wet slurps and moans I made around his cock. His words hit me like a humiliating slap, but they turned me on at the same time. 

“It’s going to happen, Crissy….. Now!”

He cried out and I felt him cum. His cock spasmed and he cum filled my mouth. There was so much cum and it was delicious. But there was more… a sensation and feeling that I didn’t recognize at first. He just kept thrusting and spurting. My body was trembling too and it was then that I finally recognised what was happening. I was cumming. 

Somehow it was happening. My cock, still trapped away, was squirting and oozing cum. It wasn’t the intense pleasure of a normal orgasm but I felt a soft release and easing pleasure. 

Once we both were spent, Brooke shut off the fucking machine and Liam stepped back. The motion had stopped, but the thing was still buried inside me for now. I could feel her start to unlock the steel restraints around my ankles.

“We all got to see Crissy’s first sissygasm!” Brooke was beaming. 

With the high of arousal fading, I felt some confusion and shame creeping in. But Liam leaned in and kissed me hard. His tongue took ownership of my mouth, pushing negative thoughts aside. 

Brooke wrapped up her livestream, waving goodbye at everyone and thanking them for their generosity. She left to go clean up, or perhaps just to give us some privacy. 

“I’m very proud of you, Crissy,” Liam said to me. He helped me crawl forward until the dildo popped free, and then he helped me stand and find my panties. 

“Thank you, Master,” I said softly. I meant it. 

He brought me over to the sofa, then sat down there with me, his arm around me.

After a few moments of soft comfort, he reached into his pocket and pulled out a phone. It was mine, which confused me since I’d left it at home. I’d only been able to leave with what I was wearing. 

“You’re not going to make it home before Cheryl, and I don’t think you want her to see you arrive like this. But don’t worry. I have a plan.”

Fuck, was all I could think.