I entered the bedroom to find Ann, still in her short nightgown, standing beside the bed. Kay emerged from the dressing area just as I walked into the...room. All she wore was a lacey bra and lacey bikini underwear. We all stood kind of frozen in place."Rob, can you believe what great shape Kay is in," asked Ann.Placing her hands on Kay's shoulders, she turned her to face me. The head on view was astounding; her big, heavy breasts and silver dollar sized areolas were quite visible in the confines. Her instructions was that she had to go along with whatever happened with him, doing whatever this person wanted, period, and as proof she had to take a cellphone picture of his cum, wherever it may be.She didn’t want to do this but I finally convinced her to, so she went to work without her panties on and her khaki skirt that goes up to her knees only. She had never done anything else sexually with another guy up to that point.When she came home from work that evening, she was very shy but. Mistress notices your glance."Yes I have been recording the action, your pitiful attempt atpleasuring an inflatable doll will be uploaded to Fetlife when we aredone......"You shiver and your cock hardens."Proof of the fact that you're not a man just a girly boy, now let'sgo!."SLAP!.Her hand lands on your bottom. You shuffle forward and realize thatMistress has also lubricated this hole so you slide in easily. This holeis definitely tighter but having just cum you know it will be a longsession.. But, Todd suggested we could win some prize money back, and besides, it was all on credit cards anyway.Two weeks before Halloween, I came home and found Todd putting makeup on, sitting in front of his laptop. He found a bunch of YouTube videos on how to do male-to-female makeup, and I gotta admit, there were some dudes who turned into good looking chicks. So, we started practicing. And we got pretty good, I think.October 30th, I started getting cold feet, but he pointed out how much we.