I was not sure. I had to move quickly.I held both his hands and looked into his eyes. I assured him it would be perfect and to have no fear. I wanted ...his to happen, he should not worry about it and to enjoy what we were about to do. Jan and I have shared many things and his cock would be one more thing. I said, "We have gone this far, please don’t let it stop now."I told him I wanted to make sure that when he and Jan made love together, he knew how to treat her properly and gently, the first. If two people were setting on the couch, I could see what was going on, if I had the door cracked open. I said to Judy, ‘Have Gil set on the end of the couch, so he will be looking away from the closet, you set next to him. You will be the only one who will be able to see me, you will be looking directly at me. I plan to clean everything out of the closet and put a chair in there, so I will be comfortable. ‘Is there anything special you want me to wear?’ I replied, ‘You know I like button up. "Samantha." When she didn't calm down, he yelled, "Samantha!" She froze in place, still terrified. He used his legs to pull her closer to him, took her face in his hands, and kissed her softly and tenderly. As he did he felt her fear change to confusion. He took her dick in hand, and placed it at his asshole, saying, "It's okay."Samantha gave him a confused look, but slowly started pressing into him. James smiled and moaned as Sam slowly pressed into him. They started moving together, Sam. ‘You okay?’ Jake asked. Caitlin nodded. ‘What’s wrong Cait?’ Jake asked, knowing something was off. ‘After spending so much time with Will and Kylie, I am reminded of what I threw away,’ Caitlin murmured. Jake sighed. ‘Caitlin, that was a long time ago. We were both so young, and honestly, it was probably for the best. We were what, nineteen?’ Jake murmured. Caitlin nodded. ‘So what’s the matter?’ Jake asked, sensing there was still something bothering her. Caitlin said something that Jake had.