Heavens Cloud

Ok just realised this is an old question, oh well just in case anyone else gets stuck.

I assume you have figured out how to use the Directions to his house, and the clock, as you've reached the gate. First time you reach the gate you meet your future self who gives you items and chats to you. It's best to write down what happens, what items you get in that order and jot down anything he says. He should give you a key to open the gate for him, but you yourself don't go in. Check your directions to see where to go next, and follow it.

When you reach the gate again, you are the previous Guybrush and have to do exactly as he does, well speaking/items etc wise anyway. For example, this is how my latest save went:
+ Handed me the rubber chicken
+ The key - which my Guybrush responded with "what's this" and I had to write down the future Guybrush's answer.
+ I asked him to tell me what number he was thinking of, 11 and a half (it may be different each time, just write down his answer)
+ Opened the gate
+ He steered through the gates and gave me the gun
+ Then he left.. So I checked the directions, it told me to go west so I turned around and did so.
+ Once I got to the gate, I went over to him, gave him the chicken, then the key, copied exactly what he said. Answered his question, so he opened the gate. I went through and gave him the gun. I think you need to go through 2 more screens at the most before you arrive at Pegnose's