Tim rolled his head back and moaned. I could see her fingers working against his anus. “It’s okay, I’ll be gentle.”I lubed the end of the plug for her and handed it to her. I watched as she put it against Tim’s anus and pushed gently. “Relax Tim. It won’t hurt as much if you don’t fight it.”“That’s easy for you to say.” He winced as Jess applied a little more pressure.“Maybe not. Just relax, you’ve seen it work for Jess.” He must have relaxed a bit because the plug started to slip inside him. Jess kept up a firm but gentle pressure and I watched as Tim’s asshole expanded to let the plug inside. His eyes widened as the widest part of the plug stretched him open, then moaned as the diameter shrank and he could close around it. Jess tugged to test the insertion and his grip.“That’s better, baby. See, it wasn’t so bad after all.” Jess teased. Tim’s cock was now fully erect and Jess was stroking it with her hand. I suspected she had a plan, and I was right.“Get in here and. I’m sure you’ll be able to handle it,” she asserted. “All you need to do is listen to their pitch and ask any questions you need to satisfy your personal understanding and tell me about it the following day in the briefing. I’ll give them a call after you leave to inform them of the change. Don’t worry I’ll make up some reason for why I can’t be there don’t worry about it; just take the day off and rest up, it will be your big day tomorrow” I sat there mouth agape still not believing this was happening. Shannon went back to her desk and said in a firm but soft tone, “James go home, oh and I won’t take no for an answer. Be here tomorrow at noon and I’ll do a final prep with you and we will head out”THE NEXT DAY “Just breathe and settle down James, there is nothing to worry about just be yourself and you’ll do wonderful” she said with her usual calmness. We had just parked in front of the hotel where the meeting was supposed happen and I was still a nervous wreck. No matter how many.
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