She had seen it develop so often on so many bottoms. Now though she could only feel the pain and knew Chloe would be the one enjoying the sight she wa... used to seeing. Worse was the humiliation of being caned by a woman so much younger than herself. Was it wrong or right though? Did age matter where discipline was concerned? Maybe not she supposed. As the second stroke landed Miss Castle’s mind was diverted from her pondering and she found herself hissing out through clenched teeth and with her. May I?" I reached hesitantly, when she shook her head up and down I cupped one in my right hand and held it, letting my thumb circle her areola. She had nice sized nipples. My hand squeezed gently."Not as big as Kristy's", she said."But perfectly nice themselves." She gave a shy smile. My cock was now firm and pointing at her. She looked down at my cock."Will that fit?" I'm not really that big. But let's do this instead. Leave your bottoms on and come here. Do you want to kiss me today?". They were also starting to take the shape of a young woman's legs. I could feel my waist getting smaller and my hips widening. I was also getting a strange feeling in my chest. I raised my hands to touch my budding breasts, but I was so amazed watching my shirt rise from my chest that I stopped only inches away. I could feel the fabric rubbing against my nipples as my breasts got bigger and bigger. They were only about half the size they were going to become when I pulled off my shirt. My chest. I knew if he resisted I would not be able to control him. “David, just so we are clear, if you resist or try to get up there will be 24 strokes of the cane. Straight away and then back over my lap. Understood?” David twisted his head around and said quietly “I won’t resist Chloe. I guess I know I need to be disciplined so what’s the use in that?” “Good boy” I said firmly but quietly relieved, so long as he kept to his word. I started spanking him and as expected his bottom clenched and my.