Yes, he does.

Much to Harry's relief, he made it back to the Gryffindor common room without anyone seeing him out after curfew. It hadn't been without risks, as he had heard a pair of prefects chatting as the did their rounds from inside a hidden passage. The familiar thrill of being out late combined with the fear of being caught wearing such feminine clothing, made Harry's heart race in his chest and his cock strain inside it's cage. He had waited several minutes for his heart to settle and to make sure the prefects had gone.

Once more, his luck had held out. The common room was empty of people, and the rest of the 6th year boys were already asleep. Quickly stripping out of the feminine clothes, Harry bundled them into a small expanded bag he had originally filled with sweets from Diagon. He would take them back tomorrow and look for more information on the cage.

The next day after dinner, Harry closed and locked the door to the Room of Requirements before making his way to the armoire. Pulling yesterdays emergency clothing out of his bag, he put them back onto their hangers and back into their place amongst the rest. Turning away, Harry missed the faint ripple of magic going over them, smoothing any creases and removing stains they had picked up. Instead, he stepped over to the box his cage came from and fished out the instruction manual. Sitting down on the floor, he began to read.

Thinking that the fastest way to get the cage off would be go through the ten sessions, Harry flicked through searching for anything that looked like it matched. Unfortunately for him, the curse on the armoire made him miss the ten basic tutorial sessions. Instead Harry found the intense sissy maker instructions labelled “Ten Session Solo Training”. Only the first activation phrase was available, though greyed out. Just below was a list of requirements that needed to be satisfied before it could be used.

Be naked with the box of toys nearby. Easily done, Harry felt optimistic that he could complete several of them before curfew, and the rest within a week. Stripping down he put his clothes into the bag he had brought and sat it on a nearby shelf. Taking a calming breath, Harry said the activation phrase and with a pulse of magic, his first session began.