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The first time he begins to question his beliefs is the first time he sees his Father's lord. The second time is merely a week later, as he watches pensive memories stored in his father's study. The memories were not his own, but they would haunt him for the rest of his life. Ironic how another's memories would be ones he would never forget. For months they would burn under his eyelids every time he closed them.
His eyes were red. He had never seen red be so cold, and so utterly cruel. Draco wondered is the dark lord was even human anymore. He certainly didn't look it. As his father bowed down and kissed the midnight colored robes, Draco was shaken to the core. His father always said that a Malfoy bowed to no man. Then again, was the dark lord really a man? Draco was so confused, and completely terrified. He was glad of his hiding spot. He did not move for hours even after the meeting had ended. Draco sat in the dark.
The next few days offered little sleep. Draco could not stop thinking about what he had seen. He had to see more. He had to know. So in the early hours of the morning, Draco broke into his father's study. A feat which proved far easier than Draco would have ever imagined. His father used Blood Wards. Which would be impossible for anyone else to open, even Draco's mother. But Draco himself shared his father's blood directly, and the locks opened with ease. He wondered why he had never even tried this before, though the thought of entering his father's domain had never even occurred to him in the past. His father, in his arrogance most likely believed Draco would never disobey him. Draco was after all, the mirror image of Lucius. In thought, beliefs, actions, personality, and features. Well Draco had inherited his father's arrogance just as he had his blood.
Lucius' study was well lit and lavish. Draco spent about an hour peering into corners, discovering what was hidden when he came across a well-concealed cabinet. Again locked with a blood ward. Draco smirked at this, and drew a few drops from his finger with a small knife he had brought with him. He didn't know that what lay inside would change him forever. Several vials lined the small cabinet filled with silver glowing substances. In the center sat a shallow bowl that Draco immediately recognized. A Pensive.
Draco picked up a vial, noticing they were labeled by date. The bottle in his had from just a few weeks ago. Wondering what memories his father deemed important enough to bottle and hide, Draco poured the contents into the pensive, and stared inside. After a falling sensation, he looked around him. Draco was in a small village. He didn't recognize the place, but he recognized the cloaked figures around him. Death Eaters, and his father we could tell by the cut of his robe. It was seemingly identical to all the others, but of a much finer quality. He could also distinguish his father's voice giving orders to his fellows.
So this was a raid, Draco thought. And unlike earlier in the week, there was no way he could be seen or physically harmed. However, Draco still followed his father apprehensively. The other death eaters in his wake trailed quietly. The approached a small house. The wards fell with in seconds under his father's wand.
Stepping inside Draco took in the modest furnishing, and the terrified man that stood wand outstretched who had obviously been alerted when his home's wards fell. A flash of green light and the man slumped gracelessly to the floor. Draco's eyes widened at the speed and ease with which the man died. His father hadn't so much as blinked. Draco was glad he had not eaten since lunch.
"Find them" Lucius said authoritatively. Draco elected to stay with his father and not to follow the other men. Moments later a sobbing young woman was pulled into the room. Lucius sneered, and asked "And the girl?" The woman cried out "NO!" as one large death eater replied gruffly, "On the way". Draco recognized Crabbe senior's voice.
A terrified young child of no more that five years was dragged into the room.