When she had first started training him he was wild and unbroken. He hadn’t wanted to be used by her, instead he had wanted to use her. She had shown him that that was not going to happen, and for the first several months he had walked around with an ass full of welt and a pony tail. The pony tail was the Mistresses personal touch on her ponies. When they misbehavied or were just starting training she fitted them with a custom but plug with an attached tail. The men would wear them while with the Mistress and after would keep the plug minus the tail. They would wear these until the next time they saw thier Mistress. Then it would come out long enough to put the one with the tail back in. This particular pony wore one for three months straight, but when he finally broke, she was happiest with him than any of her other ponies.His wrists were tied behind his head, his cock hard and his balls swollen. The cock ring was slightly too small, putting pressure on him where he was sure. I then sat back and listened to the ending of her song. She had it down perfectly, if I had closed my eyes, I could have sworn I was listening to the record (guess I'm showing my age there.) I applauded after she finished and watched her walk back to the table. I immediately decided to add another song to my list for later. As I looked up The Hollies in the book, Judy picked up her drink and sipped delicately, looking at me and standing up decided to come over to my table."Are you responsible for this?" she asked sweetly."Yeah, I really liked that Streisand you did, thought it deserved a reward." I smiled back. "I'm Rick, care to join me?" Sure." I stood slightly as she pulled the chair and sat down. "Oh, my, an old fashioned gentleman." I try, it's something my Mom taught me."We continued the small talk the rest of the evening in between songs, I found out she loves to sing duets (we sang "Islands in the Stream", "Love Shack" and "Summer Nights" as well as "You Don't Bring Me.
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