Once comfortable I removed it and kissed and licked her hole before lining my cock up with her asshole. Up to now none of them had touched my cock at all. No blow jobs or anything. My first contact with any of them with my cock was gonna be in this virgin asshole, I was so excited I was shaking.As I pressed my cock into her ass she tensed up some and cringed. I asked if I should stop and was met with a quick and decisive NO, so I slowly continued pressing until I felt her anus give and envelope my stiff member. It was so tight and I only had the head in. Amy moaned in either discomfort or pleasure, which one I don’t really know. Allowing her to relax first I encouraged her to continue playing with herself. She did just that. After taking my time to fully penetrate her I stayed in her balls deep while she again reached orgasm. When I started to pull back her asshole gripped my dick and pulled back with my cock. She became very vocal. Lots of “ oh my god” and “holy fuck”. Once I got a. “You have done really well. Tell you what; I think this game has gone on long enough! We can stop here for now and we’ll decide who wins and get you those dogs,” I pointed to a snack vendor and a little margarita kiosk next to it where Eddie had bought drinks earlier.“I think he is nervous Sis, what do you think?” Waverly’s adrenalin was pumping and she wanted to continue playing and Hayden agreed with her sister.“I am not nervous. I am just being generous. I am in a good mood. It is my brother’s birthday. I don’t want to spoil it with a lot of pervy games. Tell you what. Hot dogs with buns for you both plus the winner gets that Margarita,” I offered. I thought they could fairly easily be bribed.“We both get a margarita?” Waverly smiled greedily.I was reluctant because I didn’t want to seem like too much of a pushover. I was about to say yes when Hayden told her sister that she was afraid she wouldn’t win so she had to ensure they both got a drink.“It isn’t that,” Waverly told her.
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