Harry shook his head, "No, it was a spare set made for Hermione when she was nineteen."
There was a pause as Draco digested that, "... Granger? I'm wearing armor made for a bloody woman?" his voice was a combination of disbelief and scandalized. "Well… you did say it was loose in the chest and the hips. You are kind of a runt compared to her when that was made," Harry replied blandly. After a pause he continued, "Though apparently her boots were too big for you. Luckily Ginny's seem to fit you okay." The irony of a Malfoy wearing a female Weasley's hand-me-downs had Harry fighting down a shit-eating grin.
There was a choking sound for several seconds, and Harry appreciated how red Draco's face turned before he cut off any further reply when he announced grimly, "Darkness is already falling and I want to get moving as quickly as possible. I've never actually broken in to Azkaban before. I'm not sure what sort of wards or other issues we'll be facing."
Draco put aside his distraction and nodded slowly, attempting to match Harry's serious expression. "So… what exactly is the plan? Do you care to enlighten me?"
Harry nodded slowly, "I try to keep my plans simple. We'll exit the castle through the secret passage. Apparate to the coast, together. Assuming you've got the power to apparate that far, and you've tandem apparated before; not just side-alonged. I really don't feel like trying to track you down because you apparated yourself to some random coastline, or reattaching a limb because you've splinched yourself."
Draco nodded, "I have tandem apparated before, and I shouldn't have any problem reaching the coast."
Harry nodded, "From there, my plan is to get to the island and then try and find Regulus' cell. It's not like they offer maps to prisoner's cells. If that doesn't work, I'll line of sight apparate to the island. Track down his cell. Get him out of there and flame us both back to you."
Draco frowned, "What will I be doing during all this?"
Harry paused a moment and then shrugged, "Guarding the picnic basket?"
Draco scowled, but Harry cut off any protest. "Look Malfoy, I've gotten out of the habit of endangering others on this sort of thing. I've got out of the habit of working with people, and I'm definitely not used to working with you. You insisted on coming, and against my better judgement I'm letting you. I won't always make you sit on a sideline like this, but for now, that's how it is. I don't have time to figure out what you can or can't do."
Draco frowned, "Why are we in such a hurry?" Harry hesitated and frowned, "You saw the letter. I've been trying to deal with the information I have as quickly as possible. Before it becomes useless. The longer we're here the more dissimilar things are. I don't know if our Voldemort is here or not. If he is, any similarities to our world will disappear rapidly."
Draco turned that over in his head and then nodded slowly. "Okay." He wasn't pleased about the idea, and it showed, but he also wasn't going to argue and risk being left behind. He was determined to be part of it. He had no desire to die kneeling and kissing the robes of Voldemort.
As a last touch, Harry tossed Draco one of two grey cloaks. "When we're out there, wear that at all times and don't take your hood down. It's charmed so that only the wearer can pull it off without some painstaking charms. It will obscure your identity and modify your voice when you talk."
Draco nodded nervously and held up the cloak speculatively, "Granger's?"
Harry shoot his head. "No, Ginny's. I don't know if anyone's told you this before or not, but you're a bit on the small side."
Draco rolled his eyes, "We're teenagers again, Flamel. Besides, you're one to talk."
Harry shrugged at the riposte, "I'd offer to let you have Ron's. He managed to badger Hermione to weave a charm in that would make his eyes glow different colors when he wanted. I never spent much time copying the charm work. But the cloaks are magic resistant, and you'd practically swim in a cloak made for Ron at 19."
Harry glanced at Draco with a critical eye and then sighed, "Please tell me you didn't put the armor on overyour wand holster." When Draco's only reply was embarrassed silence, Harry rolled his eyes, "Your wand might be a bit important tonight."
They waited another half hour as the last bit of dusk faded away, before Harry decided it was dark enough to proceed. Harry cast a disillusionment charm on himself, followed by several other concealment spells. Draco also disillusioned himself, though Harry was slightly annoyed to note that it was all he did. Harry gave his companions a few more layers of protections, making a mental note to teach the blond how to protect more than just his visual presence.
They made it to the painting and Harry reached out and lightly patted a dog that was in the painting. The painting shuddered slightly and swung away from the wall like a door. Draco gave a start of surprise, but Harry ignored him. He knew Hogwarts like the back of his hand, possibly better than even the house elves. This Hogwarts seemed to be exactly the same as the one he remembered, at least structurally.
Harry was slightly surprised to find that the passage was thick with dust and spider webs, judging by the amount, it hadn't been used in a long time. Harry's suspicious nature came out and he flicked his wand into his hand, using several diagnostic spells on the area to make sure the area wasn't an illusion, boobytrapped, or in some way monitored.
When the spells came back negative, Harry grabbed the air where he could hear Draco breathing, and pulled him forward by what he believed was a shoulder into the secret passage. He lead Draco downward until the passage leveled off for a bit and then rose once more, until they came to a stone wall.
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