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I gladly did, expecting that he’ll put in my already throbbing pussy, but no, I felt it at the opening of my asshole. It was moist and I’ve never ...one anal so why not!?He slowly went in me, taking his time so I could get used to that much in there, and ease the pain (and trust me, it hurt). I stayed strong because I knew after the pain would be pleasure. He went slow for sometime, using my groans as a litmus for how comfortable I was. He knew it was time to ram home when I reached to grab his. Once my skirt was pulled up, he slipped the panties down a little more…I tried to relax as much as possible and remember to breathe. He gave my backside a few little taps with the paddle and asked if I was ready; before I could answer there was an explosion of blinding hot pain! It took my breath away, I saw spots; damn did that sting like hell! There was a short hesitation then four more, just as hard, I yelled…I howled! My voice rose in pitch as I emptied my lungs again…there were five more. I told Kate we should go home but no we followed him in and crept up onto the viewing gallery. They were unmanned courts and only two were in use, two guys in their forties were mid game in one and Mike and his partner a hot looking Latin guy neither of us had ever met before in the other.After they had been playing for about twenty minutes I took Kate's hand and started to walk to the stairs when the Latin guy took of his top, this made both of us stop to admire his ripped body. It was a. Just please be gentle.” With that, Ruth stepped out of the room and I was left standing in front of a 95 year old woman that I was supposed to sexually satisfy. I must be some kind of freak, but for whatever reason I was hard as a rock. I pulled a little bottle of lubricant out of my pocket and set it on the nightstand. I didn’t bring a rubber, since Ruth had shown me her test results, and there was no way she was going to get pregnant. I stepped over to Gladys and thought about what how I.
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