A week went by and we started the job but we were told that his grandmother was going to be there but in a separate part of the house. She was quite and wouldn’t get in the way because she was in town to visit a old friend will probably spend a lot of the time out of the house. I said it was cool and he went to get her so she at least got to meet me, he came back and she was about 5’6 heavy set women with long white hair and a nice round granny booty. She introduced herself and said that she would be in and out but just let her if we need anything. I said yes mam and she said just call me Gladys. I said my name is Brian mam and she laughed. My friend said just let him if there are any problems and left with Gladys. We began our work and finished for the day. I got there first the next morning around 5:30am and noticed that another car was in the drive. I yelled for Gladys that I was there but no response so I went on about my business. Then I went to use the rest room and walked to. I then felt Billy withdraw his cock and his fingers and for a brief second I felt empty and strange. I also thought it odd that I hadn’t felt Billy come inside me so I wondered why he had stopped.I then felt his big strong hand gently teasing my clit and his cock rubbing between the cheeks of my bottom. His rubbing increased in speed and as I was coming down from such an intense orgasm, I was quickly right back up there and barely noticed the pressure pushing on my arse hole.Billy’s cock, still well lubricated from my pussy, push slowly but firmly against my rear entrance and before I was fully aware, the head had popped past the sphincter.I winced with the pain and clenched tightly which just made the pain worse.Billy shushed me and continued caressing my pussy and with his free hand stroked my breasts, whispering soothing words to me and telling me to relax and very quickly, probably because of the fingering and the sexual high I was floating on, the pain subsided and I found.
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