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Not meaning to I let out a long moan, this being noticed by Greg as he pressed and held his hand over my hole while leaning near my face asking if I was enjoying his touches or did I want him to stop. Not knowing what to say I hesitated, Greg asking if this was my first time for a massage like this which I nodded at, Greg saying that he also does "male relief" if I wanted to go that way. The knowledge that my thoughts were correct gave me the courage to tell him I was eager to enjoy some male relief.As I lay my head back down, i felt Greg's hands on my inner thighs, motioning me to move them apart which i did hastily, to which he let out a moan, followed by comments of how hot my shaved arse and balls looked before sliding one hand under my oily balls, softly caressing them while his other hand slid deep along my crack, soon stopping at my hole, gently pressing against me when i begged for his fingers to slide inside me.As i was already covered in oil, Greg's fingers slid easily into. "NO" she said quietly. I then went for a second finger and slowly got both fingers as deep as I could in her ass. "does this hurt" I asked"a little" Cindy replied.I figured that she would have said something more than "a little" if she wanted me to stop my experiments on her ass so I decided to make the move. Without saying a word I pulled my dick out and ripped off the condom and threw it aside. I pushed my cock against her ass and started pushing harder and harder until my head started to penetrate her. Slowly I pushed into her, deeper and deeper. I was about half way in."Ouch, Ouch" she said and I slowly pulled back. To me "ouch" didn't mean stop and I didn't want to start a conversation so she could talk me out of this. I gave her a few seconds and then without a word I started pushing in again. Deeper and deeper, but now I got past the point where she said "ouch". Now I was almost all the way in, my body was pressed against her ass cheeks so I grabbed her wasted and pushed a.
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