When you have been the Best sissy trainer you have a sissy like “Lollipop”. Her sissy period started, and she had to wear white shorts mini shorts. I wanted her to make a work of art and have a free bleeding day. After having my sissy over, it was fun to bring my friend by to try her out.
I had my special glass dildo heel boots on, and I showed my friend how well my sissy has been trained. I made her open her sissy mouth and clean my heels all up. That is when I stomped her throat to push my dildo deeper. She has been instructed to have deep throat exercises and this was the perfect way to show them off. My friend really enjoyed seeing my sissy suck my dildo heel while free bleeding and wanted to try my boots on my sissy as well. She put them on and started stomping her sissy mouth. I got behind my sissy and spread her bloody sissy pussy and shoved my strap-on deep inside her. I knew if i fucked her hard i could push my dildo heel my friend was wearing down her throat even more. By the time I was done my strap was bloody and it is always my sissies job to clean up any mess. While my friend and I thought of new tasks for my sissy to do during her period week, my sissy cleaned up the bloody mess with her mouth. She has gotten enough Sissy slave training and knows what to do.