I was an anal virgin at the time and I quickly agreed to her terms. She then tied my legs spread eagle, tied one arm behind me, and put a leash on me that was tightly tight to a pole behind me, pulling my head to the wooden bed. I was bound and only had one arm to use and I used that hand to grab my dick as she lubed up a small prostate toy and slowly penetrated my ass. I did not like the sensation, but after it was in me and started to vibrate I came to the brink of cumming. She then grabbed my hand and held it down and told me that if I cum without permission I will be eating my cum. So she then said for to jack off, so I was approaching the point of no return and I asked madam if she’d allow me to cum. She said “NO, continue stroking, you need to last 2 more minutes than you may cum”. She was lightly touching the inside of my thigh while she had her toy in me, all while staring me dead in my eyes. After 30 seconds, I began to shake and twitch, and then huge spurts of. An old but effective wooden "privacy" fence surrounded their back yard, so at night you could stand out there without being seen, and it had a side entrance to enter it from the street. Both their bedroom and living room areas faced the back yard and were only covered with cheap white see through curtains that were pulled back to both sides of the window.In short, at night you could stand undetected in their back yard and see perfectly into both their living room and bedroom windows when their lights were on. Even with just their hallway lights you could see inside pretty well. You can imagine my interest in that!It was nearing Christmas and they really wanted to go home for the holidays but could not afford it. As with all the other single guys, I knew I would be working through the Christmas holidays so I showed up unannounced at their house one night and gave them money for the trip. They were just stunned, made the trip and later were very demonstrative with their.
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