Over the next few weeks, my sister had fucked my ass with her strap on every day, sometimes twice a day. She loved to dominate me, to assert herself over me and humiliate me sexually, it was like she was a crack addict, and I was her crack. She got more into it, and would sometimes make me eat her out, or lick her ass, and it became so that she had to give me permission to cum, and if I didn’t have her permission, I would get punished. She had gotten some new toys to help in my punishment, and she loved to use them anytime she could. She had bought a riding crop, a butt plug, nipple clamps, two different gags, and a chastity device. I knew something was up when she came home excited, and told me she had a present for me. She ordered me onto my knees as she tied me up like usual, and took out the bag of toys to show me. Each item she pulled out, she would demonstrate on me. She pulled out one of the gags that was a ball attached to some leather straps, and placed it into my mouth, saying this would keep me quieter during our sessions. Next she took out the nipple clamps, and attached them to my nipples and tightened them, making me squeal in pain. Next was the butt plug, my eyes went wide when I say the size of it, it wasn’t as big as some I had seen online, but it was still pretty big, then she lubed it up and shoved it up my ass. Next she took out the riding crop, and I knew I was in for more pain, and she didn’t even bother to explain it, she just struck it down hard on my ass, making me cry into the gag. And last she took out the chastity device, and I didn’t know what it was. She explained that if I was to be a girl, I wouldn’t be needing my penis anymore, and attached it to my cock. I could see tiny little pins or needles on the inside, and could only guess were there to cause pain if I got a hard on. With the last of the toys revealed, she said that she was going to work on getting some female hormones to give me to make me more feminine, and to give me real breasts.
After she was done with the toys, she did the usual, dragged me onto her bed, got her strap on, pulled the butt plug out, and started fucking me. While stabbing her cock into me, she grabbed the riding crop and started bringing it down on my ass making me cry more, but she didn’t care, she just kept smacking my ass with it until there were welts. As she was fucking me, my cock started to get hard, and pressed into the pins inside the chastity device, and I started crying again, and she stated that the device must be doing its job. Finally, my torture was over and with a few more thrusts, she pulled out, and let me go. I went back to my room and just lay on my bed, looking over the device that now encased my penis. It had a hole in the tip for me to go to the bathroom, but other than that, it was doing its job.
The next day my sister came into my room and told me she was going to have friends over, and that I’d better look pretty for them, I just put my head down, and nodded. By the time they got here, I was fully dressed, makeup and hair done, and sitting downstairs waiting for the humiliation that was to come. When they got here, I saw that it was two boys that I went to school with. I knew I was fucked, because they knew who I was, and there was no way that this would be kept secret. My sister brought them into the living room, and introduced me as Kari, and explained to them that it was the name she had picked out for me. The two boys just looked me over. One of the boys, was 15, his name was Seth, spoke up first and stated how cute of a “girl” I was. And the other boy, Noah, who was 16, agreed with him, and said that he’ll enjoy seeing my lips wrapped around his cock. I realized what was going to happen, my sister had talked to these boys at school and told them what she did to me, and told that they could use me as their personnel fuck toy.
My sister ordered me upstairs to her room, and came up a few minutes later with the two boys. She went about preparing me, however, this time she pulled out the other gag that she had bought, it was a ring gag, big enough to keep my mouth open, and for a cock to fit through. She placed it in my mouth and tied me up, and the two boys tossed me onto her bed. The two boys proceeded to get undressed, all too eager to fuck me, and my sister told them to have fun with me, and left the room.
Neither boy wanted to wait another minute, got onto the bed one each side of me, and positioned their cocks at my mouth and my ass, and not being able to protest, unceremoniously shoved their cocks in without hesitation. They started to fuck me for all I was worth, stabbing their cocks in and out of me; I was just a piece of meat to them, a piece of fuck meat... They fucked me for well over 10 minutes before they came, not even bothering to pull out. Over the next few hours, they took turns fucking either my mouth, or my ass, all the while talking about how all the guys at school would love 10 minutes alone with me. Little did I know that they wouldn’t tell anyone, that was part of the agreement, they tell nobody, and they can use me whenever they want. They were fucking me one last time when my sister walked into the room, telling them they needed to finish up before our parents got home, so they fucked me hard and quick, cumming once again inside my mouth and ass, then got dressed, and left, saying they would definitely be back. I was let go and I went back to my room and just lay on my bed crying, until I fell asleep.
The next day was a school day, and I was woken up by my sister, since our parents leave for work before we leave for school. She ordered me over her knee, and gave me a spanking, then grabbed the butt plug and plunged it into me. She said that I was to keep it in all day while at school, except to go to the bathroom, and then I was to put it back in afterwards. She left, and I got dressed and ready for school, and did as I was told, and left the butt plug in all day. It made the day very uncomfortable, I was squirming in my seat all day. I kept getting looks from Seth and Noah, and figured out that they hadn’t told anyone since nobody had come to tease me yet. Halfway during the day, I had to go to the bathroom, and Seth saw me go into the bathroom and followed me in. When I saw him come into the bathroom he pushed me into the stall and told me to give him a blowjob or he’d tell everyone about what happened. I had no choice, so I got onto my knees and started sucking him off until he came in my mouth, and told me to swallow it. Again with no choice, I did as I was told and swallowed the mouthful of cum. He left, and I went to the bathroom, went back to class, and got in trouble for taking so long.
The day was over and I got home, where my sister was waiting for me with another “present”. She explained that a friend she knew online had sent her some stuff for me, and she pulled out a syringe, and a bottle of pills, saying they were hormones to help me look more feminine. I realize I could have ended everything there, knowing this had gone too far, and just take the punishment of dressing in my sister’s clothes, but something inside of me wanted this, a part of me was actually enjoying what my sister was doing to me. So without arguing, I let her inject me with the hormones, and took two of the pills. She handed me the bottle, and told me I was to take two of them every day until the bottle was empty, and then she would get me some more. I asked her how she was going to hide this from our parents, and she said that when the time comes, and the changes start to become apparent, that I would tell my parents that it was my wish to become a girl. Once again, I lowered my head, and agreed, knowing the humiliation that would come on that day.