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It was now or never I thought. Holding my cock firmly I rubbed it along her lips, positioned it above where I imagined her hole to be and slowly pressed. Then I pressed a bit harder. It wasnt going on! I sort of began to panic, why the hell cant I get in there, my thumb has no problems. I frantically slid my cock up and down her lips, pressing here, pressing there, and still I couldnt get it to slide its way in. Suddenly she let out a brief sound, and moved slightly. FUCK! I thought to myself,. I did as I was told of course.She asked me about my daily life an did any of my Friends know I was a sissy? I said no they didn't an begged she stop calling me that.She took her wig and put it over my head and styled it. She then took some makeup and applied it to my cheeks and lipstick to my lips and in the mirror I could see what appeared to be a young lady looking back at me.She didn't tie me up or handcuff me so I knew this would be something different. We sat together for over an hour when. I asked my Mom if she thought it would help me, and she said she thought so, Sir” Buttercup’s answer was thorough and had zero snark.I was instantly skeptical and started trying to work out what her real motivations probably were.“Did you make some fucked up bet with your mother?” I asked. That was probably it. She probably bet Joy that she would serve in exchange for 100% of the money she earns over two years instead of just 50%.“Yes Sir, I bet her that if I quit before she did that I would go. This hot game continued for months. I added a lot of things into this sexual game. I started fondling my sister’s breasts and rubbing her ass. Kavitha became more open and more involved in the game. It became our daily routine and we started doing this in the early morning too.Once we went on a trip and came back home. As we are tired, we slept without rubbing each other. But my sister woke me up in the middle of the night (like around 2 am) and asked me, “Can we play it, Deepak? I am not.
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