I had taken it so easy on her when she was sixteen, that all she felt was the arousal and not much pain. I think we both underestimated the amount of pain a hard wooden hairbrush can deliver with only ten strokes. When she is able to speak, she says, ‘Oh Michael, it hurts sooo much … I didn’t think it would be so bad!’ She gets up and straddles my lap facing me with her legs around me and then she throws her arms around me sobbing hard into my shoulder. I can feel myself starting to get harder with her pussy resting on my bulge. I have both of her ass cheeks in my hand, and the other one on her hip trying to console her. I am still massaging her butt, with my middle finger naturally slipping down between her cheeks and onto her sopping pussy lips. I massage her with my finger and slowly slip it into her. She pulls back a little to look into me, and framing my face with her tiny hands and her lips close to mine, she softly and quietly says, ‘Michael, please fuck me!’ I can feel. After three sippy cups, I'm feeling drunk. Also, any inhibitions are melting away and I'm enjoying myself. I let myself go to being a submissive sissy. I have nothing to think about except bringing pleasure to John. They gag me again and my hands are bound in front of me. I hold them daintily on my dress. Nina laughs and whispers something to John. He also seems to be getting drunk. I see him reach down to the side of my chair and then I fall into pleasure. On the side of the booster chair must have been a switch, for now the penis is vibrating inside of me. I start moaning around the gag. The sensation overpowers everything and I'm only focused on the penis inside of me. "Your sissy seems to be enjoying the chair," says someone, but the voices are distant as the vibrating penis work on me. I feel pressure building inside mean it is like I have to go to the bathroom but can't. My feet swing in the air and I loose control of my bladder. The warm liquid is spreading around my own.
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