Sissy Goes Live Pt. 02

It had been a couple months since I last went live. After my last stream I got into contact with my new master and we arranged for us to meet up and for me to start my new life. I was excited and nervous. I had never met this man before and I had basically just signed away my life to be his live in sissy fucktoy.

He paid for me to fly out to him and he would pick me up from the airport. On the drive over he told me that he was my new master and that I was to do anything he said and that if i didn't there was going to be consequences. He was a 6' 4" super muscly black man, I knew I was going to love every second of worshipping his body.

As we were driving he told me that he was horny just from seeing me at the airport. I was wearing a tight pink booty shorts that barely covered my ass. I had a short crop top on. I had these giant hoop earrings in my ears and I had a choker that said slut on it. I had made my face look slutty as possible with dark eyeliner and my lips looked massive and very very fuckable.

He rested his massive hand on my shaved smooth legs. I was wearing the cage still and I could feel my little clitty start to strain against it even though it was only bigger than my fingernail. "I want you to suck me off as we drive slut."

These were the first words he had said to me the entire time. I was shocked by how deep and manly sounding his voice was. I instinctively reached over to him and started to rub what felt like a giant hose reel in his pants.

I was getting more and more excited by the second. I had to have this man in my mouth immediately. I started to pull down his gray sweatpants and right away his cock sprang to life right out and stood to attention. I let out a very loud gasp and he laughed. "Never seen one so big have you slut?"

"No sir, you are my first real man that I have been with." I started to rub his giant shaft with my small dainty hands.

The skin was soft and I could feel every vein stick out. I moved my face closer and the smell was intoxicating. I had to have this monster in my mouth.

He was about 11 inches and he was girthy. I wrapped my mouth around the head and started licking. Already, my master was moaning and it was turning me on more. I started to take him further and further down my throat. I could literally feel my throat expanding and the choker was getting tight. I got him all the way to the base with ease and my master let out a low deep moan.

He grabbed me by the hair with one hand and bought me back up for air, but only quickly before he slammed the full 11 inches right back down my tight throat. The sounds my masters cock made with my throat were amazing. I wanted him to fuck my throat for the rest of my life.

Eventually he was close and he held my head down deep on his cock as he shot sticky load after sticky load right into my throat. I could feel it building up and I tried my best to keep it all down. Unfortunately some spilled out onto him. "You better lick that up you dirty fucking slut."

As he pulled me off his still twitching dick, I went around the base of my masters massive cock and licked up all the cum. It was delicious.

I had been living with him for a couple months now. He would go out to work and I would stay and maintain the house. He lived in a giant mansion with white walls and floor to ceiling windows. He had given me a room to start my new streaming career. I decorated it with pretty fairy lights and I got a nice round sofa put in the middle of the room that I would play with myself on. I was living my dream life.

One day my new master got home from work early and told me that it was time to make my return to streaming. I was excited and anxious. I asked him what we would be doing and he told me that he had a surprise for me. At this point we had been fucking everyday, sometimes 2-3 times and I loved every minute of it. Every weekend he would invite his 3 closest friends, my other Masters, and they would just gangfuck me all weekend long. I still hadn't been let out of my cage but at this point I completely forgot about it.

I got dressed up. I was wearing a pink miniskirt with no panties on underneath so my ass was sticking just out the bottom. I had fishnet stockings that ran the full length of my legs. I had a white shirt on that said 'Daddy's toy' and my long hair was done up in two long ponytails.

I walked into my streaming room to see all my masters sitting on a lounge. My cage immediately tightened as I felt my little clitty push against it's plastic pink cage. I was so excited and super fucking horny.

The red light on the camera was on meaning that I was already live. I could see the viewer count was already close to 1000 people watching. This made me more horny knowing that so many people were about to watch me get gangbanged and fucked hard.

My Master stood up and walked over to me and roughly wrapped his hand around my throat. "Finally slut, we've been waiting hours for you. What took you so long?"

My heart was pounding with anticipation. "I'm sorry Daddy, I just wanted to look perfect for you and your friends" I put on my cutest, most innocent smile and tried to look enticing to the men.

"Get on the bed slut, we have a surprise for you." said my Master. I was practically dragged by my neck, and thrown onto the bed. "Now stick that huge tight fucking ass up in the air" I bent down as low as I could go and arched my back so that my Master and his friends and everyone watching could get a glimpse at my perfect little asshole.

My Master went over to the drawer, which normally would've been used for clothes by any other normal person, but we were not normal people. Inside each draw was an array of different sex toys. Each draw mostly had a theme associated with it. There was a BDSM draw, a chastity draw, anal plugs and such draw and even a horse cock draw (that one was my favourite).

He went over to the anal plug drawer and reached inside. "Now before you got here slut we held a little poll to see what our viewers would most like to see used on your pretty little asshole." This was very exciting and it only made the pain in my cage more enjoyable.

"They decided that they wanted to see you fit all these inside you" My Master proceeded to pull out a new toy that I had never seen before. It was a set of the largest anal beads I had ever seen in my life. There was 5 of them and each were bigger then my fist.

"I hope you are ready to take each one of these. If you don't take all of them then you will be punished severely." I was shaking with both nervousness and excitement. This was going to be really fun!

My master walked up to me and gave me a hard slap right on my ass. I let out a long moan which inspired him to do it again, this time harder. My ass was already aching and this was only the beginning. I was in for a long night.

A large bottle of lube was produced from one of the drawers. My master started to pour the lube all over my ass and rub it against my hole. I could feel my clitty straining hard against it's pink cage. I was never going to get pleasure ever again out of that useless thing.

I started to feel my masters hands rub all over my ass. He groped and rubbed his giant muscular hands all over my pretty white boy ass. The next thing I knew there were 3 fingers inside my asshole. I didn't know how excited I was because all of a sudden I was leaking huge amounts of pre cum out of my cage. "Look at this boys, the slut is already leaking."

I could see everyone in the chat calling me filthy names like dirty whore and stupid slut, it sent shivers all over my body. I was so distracted by this because before I knew it my Master's fist was all the way inside my tight asshole. "Holy shit, this bitches ass just opened all the way up for me!"

I could feel him start to flex his hand inside, stretching me out further and further. "Get over here boys, you gotta try this sluts asshole."

All my Daddy's got off the lounge and started to crowd around my asshole. They began feeling me up.

I could see they were all starting to lube up their hands. This was going to be rough. Now I feel something needs to be said about all these glorious mens beautiful hands. They were anything but small, small hands are my tiny little dainty ones. These gorgeous men's hands were giant, veiny and could cover my face with one go. Needless to say they were massive.

My master made a fist in my ass and started to pull out. I could feel my hole begin to stretch larger and larger as he pulled out. There was a hot burning sensation as he did so and I loved it. The next man stood up and just made a fist and shoved a the whole thing straight in.

A gasp escaped my enhanced painted dick sucking lips. He started to vigorously punch fuck my asshole. This fully sent me over the edge as I felt a sissygasm rupture through my whole body. After I had finished shaking he retracted his hand.

I was in such a delusional state I would do absolutely anything they told me to do. My brain was absolute mush by this point. The next two men stepped up together. I only partly comprehended was about to happen. My master would later tell me that the whole night they were running polls in the chat and this specific poll was for how many hands to fit in my asshole.

I thought it was just the two of them but I soon discovered that nearly everyone voted for all of their hands to fit inside my asshole at once, and they wanted it done in groups! So arguably the daddy's with the largest hands stepped up together, open hand and they both began to push.

The pressure was immense but I knew I needed to relax for two reasons. 1. That this was nothing compared to what I was going to have to go through later and 2. That I really didn't want to disappoint my fans!

One of my masters started pouring lube above my ever stretching asshole. It started to glide over their hands which made it easier. With a loud pop both their hands slid into my asshole! An even bigger sissygasm rippled all through my body and I knew that I had squirted all over the bed.

This was insane, I had to of the biggest hands inside me! I could feel them begin to explore the insides of my ruined boy pussy. Before I even had time to understand what was going on the other two daddy's stepped up and begin to push as well.

My poor little asshole was never going to be the same after this. Obviously room was going to have to be made for these other glorious invading fists, so the first two daddy's began pushing further in as well. So now technically I had four hands all pushing to get inside my needy asshole. More lube was generously applied and before I knew it I had all four inside me!

The first two were now actually elbow deep in me and the other two were just halfway up the wrist. This was the most insane full feeling I have ever had in my life. My whole body would not stop vibrating, this was pure heaven.

I could feel them sometimes make fists all together and then sometimes they would do it separately. The feeling was intense and sensational. But that wasn't the real thing that was meant to happen. That was just meant to be a warmup....oops.