The plan was to get Jayce to relax as much as possible before a dick was going to go deep in his tight asshole. I asked Leon to come around to the side and play with Jayce's nipples, and so he did licking each one, biting them and Jayce's face showed that he was enjoying it. Moving the guys along, I told Sean that I would pay him the $1000, if he would rim Jayce's ass, thinking about it for only a few seconds he said he would do it. When I ask Jayce if he had ever been rimmed before, he said that his girlfriend tried it once. Opening up the futon, Jayce assumed the position and as Sean got started, Jayce started to relax more and push his ass in Sean's face to get him to go deeper. Using both hands Sean opened up the ass, in order to get his tongue really in there. As Jayce was getting rimmed, his mouth was busy sucking on Leon's cock. The more that Jayce got turned on the faster that he seemed to suck. I went back to Sean and asked if he thought that Jayce was ready to get fucked, and his response was that Jayce was too tight. However, maybe with some fingering that would get him to loosen up. With a lubed up finger, Sean started to insert it in and after only about an inch Jayce seemed to experience the discomfort. I just kept having Sean use lots of lube to help make it easier for movement, but he was being very careful. Every once in a while Jayce would moan more, but he did concentrate on the oral which seemed to work.