It was now many years since the day Bilbo had returned to find his belongings being auctioned. That wasn't the most painful part of it though. It was the memory that came along with it. The time when Bilbo had to disclose his relation to the thirteen dwarves. He couldn't bring himself to do it just as yet. The stinging memories of their deaths was all too fresh on his mind. The others at least recieved a final farewell with honour, but Thorin wasn't even found. The best Bilbo could muster up was that his employer was "a friend". Many years went by after that. Drogo Baggins and his wife had drowned, and so Bilbo had taken young nephew Frodo in. As cheerful as he was, Bilbo taught him Elvish, and all else that he had learnt on his adventure, and before it. He hadn't recovered from his loss but had learnt to live with the massive void it had left in his life. He discovered that the times he taught young Frodo helped him remember them better, allong with happy memories of them. He had told stories of his adventure, but what he had brought back, was still kept hidden away from the eyes of the inquisitive young hobbit. The sword, he had kept away in a little chest. He would have done the same with the ring, if only he didn't feel so possessive about it. He couldn't find a moment's peace without knowing that it was safe in his pocket. In a way, it was almost like Isildur's predicament, for that ring held memories of struggle and pain that he couldn't part with just yet. Moreover, it stopped him from growing much too old. If the ring would help him surpass the Old Took's age, then why cast aside his good fortune? He would live to see Frodo grow into a fine lad and tell tales of the dwarves he had met for himself to the young ones.
It was after many years that Bilbo began to realize that whatever was happening to him may not end well, and yet, he couldn't bear to part with the ring. More or less in Isildur's words, it had been won with much pain. It was around this time that his eleventy-first birthday came around, and it was then that Bilbo saw the Grey Wizard once more. The last he had seen him was after the death of the dwarves, but there was no exchange between them, for Bilbo had too much guilt and anger buried within him, to talk to the wizard just then. After all, Gandalf hadn't been there to help them. In a way, many of their deaths were still on his hands. Frodo was busy with the preparations, spending some time with his friends as well. The celebrations that day were too good to be true, except for the fact that the Sackville-Baggins came along as well. In fact things were so entertaining, that nobody knew that it was all coming to an end soon. Much too soon. Bilbo proceeded to give his speech amidst much commotion. His last one, before he cut himself off from the rest of the Shire. Nobody would know. Not even Frodo. He had decided to go away on a long journey, though he didn't know where to. He wanted to see Mirkwood, and the Misty Mountains one last time. He wanted some closure. It was that night that Gandalf confided in him about his suspicion regarding the true nature of the ring. Truth be told, they had then proceeded to confirm that it was indeed the One Ring. It was too much to take in. To know that he would have to part with it. To know that the sacrifices of the company were in vain. To know that Sauron had returned, and there was nothing he could do about it, but part with the memory. He couldn't do it. It was his ring. His Precious.
It was soon after, that Bilbo's young nephew, and proclaimed heir,walked in after the day's celebration. The two had been waiting to talk to each other. One, to share news of joy and celebrations. The other, not so much. Frodo was told of the quest one of them would have to undertake. Frodo had never wanted to leave the Shire, but now, he realized that he had no choice. His uncle had had quite an adventure. He would never be able to complete another journey at this age, without the ring, and without a weapon. It was his turn now. Things were equally difficult for Bilbo too. Now that Frodo would be leaving the Shire with the ring, he would have to hand over his sword too, so that Frodo could keep himself alive. Deep down, Bilbo couldn't bring himself to leave even the tree and his home behind. The last of his memories of that fateful day when he had lost the company to another world. Old age had tried to claim many others, failing only because he had recorded them. No. He would stay back in the Shire. He would spend the rest of his days, reflecting about the past, and continuing to write them down so that Frodo could learn the truth about what really happened so many years ago. That is, assuming Frodo ever came back.