After emailing back and forth Cindy and I split a hotel room and met up in the following weeks. We hugged again and quickly found ourselves out of our clothes. I had music going so the mood was set. Since this was my first time getting pegged and switching roles, I wasn’t sure on what to do next. I was clueless honesty. Usually I make the progression and undress the women telling them what to do. Cindy could sense that I was lost on what to do. She held my waste from behind and said “relax, let’s take these off”, dropping my shorts to the ground to bare my shaved naked ass. She responded by telling me that I had a real nice ass and to get on the bed and assume the position. She kept her lingerie on with the thong. I got on all 4’s butt naked feeling nervous and vulnerable on the inside. There were numerous thoughts running through my head, mainly how did I get myself into the situation. Cindy came from behind me to lube my ass telling me to spread my legs and arch my back. She pulled. I was keeping him teetering near boygasm, but backed off every time he got too close keeping close vigilance slipping 1, 2, 3 or more fingers inside the boy. Aneel quivered and grunted still more as he felt his boy hole being stretched wider than he ever thought possible while I leaned over him, keeping him inPlace and pleasured his cocklet and balls with one hand and stretched his boy ass with the other. I was also waiting for the cute boy to adjust to the stretching, then resuming pumping and twisting my thick fingers to prepare the tight pleasure palace which was now seeming ready and relaxed for penetration and fucking it deserved.I pulled my slick fingers from the boy’s slippery wet hole, quickly lubed my cock, and positioned it at the boy’s now almost red and puffy yawning entrance. Aneel felt the difference at once, and looked over his shoulder to see what I was doing. He was speechless and scared that no way my long thick thing was going to fit inside his little ass! Just.
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