1. The Gym


    Date: 2/19/2024, Categories: Transgender & Crossdressers, Author: byFindingStephanie

    ... chain similar to what you would use to tie up a dog. He reached over and put the collar around my neck then he tugged on the leash. "Get on the floor on your hands and knees." I followed his instructions. "Good girl." He replied.
    
    He positioned the machine in between my legs, he reached up under my skirt and pulled my thong down my legs, taking it off of me, then he attached two more cuffs to my legs then leashing them to the machine, ensuring that I couldn't move my legs at all. He then placed something around my little dick and balls that I couldn't place. He put a camera on my night stand, the light went red. He went back to the machine, I turned to see him securing on a small pink dildo. I guessed it was just slightly smaller than my brother's dick. I felt a cool sensation on my butt hole, then felt first one finger slide in then after he felt like it was enough, he put in a second then finally a third. I was moaning the entire time.
    
    He reached up to turn on some music, it was don't fear the reaper, my Dad always did love classic rock. When he took his fingers away, I was disappointed to have my hole empty again. The machine started to make noise, the dildo pressed against my hole and then popped in. It began to slowly fuck me. My step dad sat down in front of me on my bed.
    
    "Okay baby. I'm going to be watching you through this camera and after I go to bed your brother is going to take over. If you even think about moving away from the machine, lying down on the ...
    ... ground, or in any way have that dildo stop fucking you, you will get one of these." He held out a remote and pressed the 1 button on it, I felt a shock to my genitals, I cried out in pain. "That was only level one, this goes up to 5. Each time you move, you will go up a level. I would prefer not to use this at all." I nodded now understanding what he had put around my junk. "I will be back on occasion to increase the speed of the machine and change out dildos. Your brother will be down to feed you your dinner after he's done eating. He told me that you already got a snack when you came home, so you can wait until he's got some food in him to recover."
    
    A look of shock crossed my face, "Oh don't worry sweet heart, I'm not mad. Jared tells me everything and I'm happy you were being such a good little sister to your big brother. It's nice after a decade for you two to finally be getting along. I was tired of breaking up fights." My Dad kissed me on the cheek and then left the room but not before turning up the machine one level, so it would start to fuck me faster.
    
    I lost track of time in a similar way to when I was at the gym, my Dad had come by to turn up the machine a few times. I could smell dinner and just as that was happening, he replaced the dildo with a new bigger one that was slightly bigger than my brother's, lubing up the dildo and my hole again. That dildo had a bit more difficult time of popping into my virgin hole. He turned down the speed of the machine to ...
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