Before the notification for when the day was set to begin, Daddy had me prepare in advance. The morning of I took a long bath, I soaked for a long time in rose scented water, and made sure I was shaved from head to toe, as close as I could get. I always make sure that I don’t have a spec of hair on my body, even for my little clitty and balls, totally hairless. Drying off after the bath I make sure I apply scented lotion all over my body to make sure I smell the part of a sissy, I make sure to apply a coat of perfume as well. To continue preparing my body and holes, I start to fill up my enema tool and fill myself up, making sure that my insides are clean as well, once completed I make sure to insert my new toy, a remote controlled butt plug, so that Daddy can keep me on my toes. To make sure I am an extra good gurl, I attach my clitty up in the cutest little pink chastity device and lock it shut. To better control my chastity, I lock it in a combination lockbox and reset the code so I don’t know what it is and send a picture of it to Chastikey so that Daddy can control that as well.
To get ready for the day’s adventures I was instructed to make a few small trips first, I put on my yoga pants, a wig, and a simple shirt, put on my cute sandals and headed out the door. The first stop was to Sephora, where I had arranged to have a full makeover done. I made sure they went extra heavy on the makeup, as I had a long night ahead of me. The sexiest eyes, long eyelashes, and a bright red lip, I was definitely ready for the town. Making my way through the mall all kinds of eyes were on me, I was in sissy heaven as I made my way to my next stop. The cute girl welcomed me to the nail salon, I had very specific instructions on the type of mani/Pedi that I was expected to get. I picked out the brightest pink color that I could find, I made my way to get my pedicure first, the girls were giggling about me but I didn’t care, this is what I was meant to be. For my manicure I had acrylics added, they were about ¾’s of an inch long and were in an almond shape, and painted in the same bright pink as my toes. They finished up and I sat to let everything dry, I spent a moment just thinking about what might be in store for the rest of the day’s adventures. It was in that moment that my ass started to vibrate, Daddy was trying out my new toe, and of course, I couldn’t do anything about it. I wiggled a little as the waves of pleasure started to flow, my clitty strained against its enclosure, just as I reached my max it stopped, and I flopped back in my chair. I grabbed my things and started to make my way home.
When I got home, Daddy pinged me to join him on Skype for a little bit so that we could plan the rest of the day and have a little fun before continuing on. While on Skype I made sure to tell him about my day so far and showed off my makeup and nails, and made sure to show him I was locked, and that my toy was in place. I was then instructed to change into my purple lingerie and sexy heels and to start up Chaturbate. I quickly changed and turn on Chaturbate, I typically do these shows for Daddy, he loves showing me off to people and this would be the first show with my new toy. I performed lots of actions, spanked my ass, put my ballgag in, showed off my mani/Pedi, all while he was turning the butt plug on and off, it was driving me crazy, I was leaking the entire time. I know it was making him and everyone else incredibly hard, so I continued to enjoy it until he knew I had enough and it was making me so horny I would do almost anything. He said it was time to continue the afternoon adventures.
Daddy decided that he would dress me for the evening/night, I was told to put on my sexy black stocking’s with the attached garters, and to put on my bright pink thong. After doing that I put on my short snakeskin mini skirt and pink bra with my new breast forms. Daddy had preselected a number of temporary tattoos for me to apply, some right on my chest, and my ass, and on my ankle, if folks didn’t know what I was into they did now. I proceeded to put on my black mess top and connected it between my legs, I also put on my jean jacket. I slipped into some sexy heels and then I was ready for the rest of my day. I touched up my makeup a little, readied my purse and awaited further instructions.
As my butt plug started to vibrate, I was sent an address by Daddy, I knew what it was immediately, it was the address for a local casino, probably about an hour away, that could be quite the long trip with a vibrating plug in my ass, hehe. I made my way to my car and I was off, it was such a long hour, just thinking about what Daddy had in mind, my mind was racing. When I got to the casino, I made sure to text Daddy a picture so that he knew I was there, I was then instructed to enter the casino. I felt like such a sissy as I made my way to the door, the eyes of everyone looking at me, men, women it didn’t matter. I strutted my way in and started to check the place out. I made my way down to the first floor and found an empty slot machine and sat down, I reached into my purse and pulled out some cigarettes and lit one up. I took some more pictures and sent them to Daddy, I played the slots for a little bit, and then someone sat down next to me. He asked if the seat next to me was taken, I said it wasn’t and gave him a little smile, he gave me a little wink back. I decided to play with him a little, I went to move to another machine and dropped my purse next to him, I then bent over so my ass was in his face, I smirked and said, sorry, as I waddled away.
I made my way around the casino and I couldn’t help but feel like I was being watched or followed, I didn’t think much of it as I made my way to a quieter part of the casino. I sat down at another machine and a few men stood at the machine next to me, I could feel their eyes staring at me, I glanced up and smiled at them. I asked them how they were doing and if they were winning at all, one of them said that “now they were”. The one sitting directly next to leaned over and put his hand on the inside of my thigh and whispered, “we know what a little sissy you are and your daddy has been paid in advance, you should meet us in room 404. My eyes were probably as wide as can be, how did he know Daddy? What should I do next? What if they had something on me? I waited for a few after they left and thought long and hard about my next steps.
I slowly made my way to room 404, my hands shaking, I nervously knocked on the door to room 404, I younger man answered the door, “We are so glad you could join us” Us? The door opened and there were at least 5 other men in the room, all drinking and having a good time. I entered and the door closed and locked behind me, I was instructed to change, I went into the bathroom and put on my purple lingerie and made my way back out into the living room. I was told that I had to service all of them before I would be allowed to leave. I was pushed to my knees and then someone stood in front of me. I proceeded to undo his pants and take out his cock, I slowly stroked it and started to lick it, I then heard a number of other zippers and belts, my bright pink nails wrapped around his cock and I sucked it. I was told to get on the couch and to bend over it, the first cock was still in my mouth as I sucked it. I could then feel the hands of another man touch my ass and then he smacked it, again and again, I moaned in pleasure. I felt the butt plug being moved in and out and then removed, I felt their hands covered in lube rubbing my sissy pussy, I then felt a large dick being inserted. They continued to fuck me and treat me like a toy, taking turns, gagging me, etc. I rode their dicks and stroked and sucked all at the same time, I was in absolute pleasure. I didn’t want it to ever stop! Eventually, I got down on my knees and continued to stroke and suck each one, they all jerked all over my face, I was drenched in cum. My own little clitty was dripping as well, and it was only 5 pm, what else would I be able to do tonight.
The last man jizzed in my sissy pussy and stuck my plug back in, they rushed me to the door and pushed me to the ground and threw my clothes at me, called me a sissy and a slut. I quickly found the closest corner and put my outfit back on. While walking back to my car I stopped at a woman’s bathroom and cleaned myself up a little. I removed my plug and let the jizz run out of me. Before re-inserting the plug I stuck a tampon in and tied the string around the plug. I gathered myself and made the long trip back to my car. Once safely in my car, I had a bunch of messages from Daddy, with plenty of images and videos from what had just happened. In my glory I failed to notice they were taking images and videos, Daddy had all of it. While sitting in the seat he turned my butt plug on full blast and said we had one more stop before it got too dark.