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I stepped forward and placed the tip of my hard cock tight against his asshole. “Do I do it slowly or just shove it all in at once?” I asked, having never penetrated anyone’s asshole before. “Start out slowly,” Jake said as he sighed when he felt the tip of my cock press against his asshole. “I’ll let you know as we go.” I let go of Jakes left leg and gripped the base of my hard cock with my right hand. Jake reached up and held his leg, pulling it down to his chest and out to the side. I held unto his right leg in my left hand and looked down at him as he looked up at me and smiled. He took a deep breath and exhale. I pushed my hard cock slowly into his asshole until just the head of my cock was inside him. “Stop, stop for a second.” Jake sighed. “Does it hurt?” I asked. “A little, but it feels good too.” Jake replied. “Okay, do a little more.” I slowly pushed my cock a little farther into his asshole. Jake’s breathing became shallow and quick. He began to moan softly. I pulled back. A four person game of truth or dare, with two guys and two girls. The starting player would challenge one of the other three with the simple inquiry: “truth or dare?” Every player was permitted to choose three truths per round and unlimited dares. Upon successful completion of the challenge, that player would then become the issuer of a new challenge. If that player refused the challenge or was unsuccessful in the completion of a dare, they would be assigned a penalty and the issuer of their challenge would then get to challenge one of the other two players. When two of the four players had used up all of their truths, the round would end and a new one would begin. Each round supposedly had the potential for new conditions, rules, or qualities.Everyone knew some variation of the game and had played during their younger teen years. The issue with the game had always been compliance. Too racy of a dare, suddenly the game stopped and everybody backed out. Too tame of dares or too many.
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