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She put my legs back in missionary position, and eased the black dildo into my ass. My soft dick looked like it was not even there compared to this dildo. It was as if it had shrunk back into my body knowing what was about to happen. For the first time in my life I really felt completely feminized. She drove the dildo deep in my ass it hurt so bad being my first anal. Luckily enough Vanessa was gentle. She did not give it to me hard until I got used to it.She started driving the entire dildo into me. It started to feel good to have this in me. I leaned back so she could get in deeper. After about 15 minutes of her pounding my ass I felt something strange. A shock wave same through my ass and a long stream of cum came out of my still soft dick. It felt like nothing I had ever felt before. I felt completely satisfied. Vanessa sat down on top of my and I gave her a huge hug. We both agreed to do this more often.Over time Vanessa would use dildos on me more and more often, as I did on. " Yes, Master." What if I were as unfair as you say I am?" He asks."You aren't unfair, Master." You said I was this morning." That's not what I meant, Sir." So now you are arguing?" Sorry Sir, I'll be quiet."As I was speaking he was pulling his belt out of the belt loop of his pants. I wasn't ready for the loud painful POP! as the leather hit my ass leaving a bright red line. I whimpered and gasped at almost every stripe that was left with the thick leather. By the time my ass was bright red and bruising I was trying to hold back the tears. I felt so bad to deserve this from Master but at the same time is was so slick between my legs. When my loving Master noticed I was struggling to keep still He stopped and rubbed the burn from my brightened ass. When I whimpered at his touch he pulled me into his lap and held me close."I don't like being called unfair." I'm sorry, Master. I promise to never question your reasoning for doing something again." Good, pet. I love you my slut." I love.
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