Wall Market
The Wall Market is a bustiling place with lots of activities and shops. Ignore that for now. You'll want to head north, all the way to Don Corneo's mansion. Talk to the guard and he'll notice Aeris. Aeris tells the guard she'll bring a friend... and uh, well, Cloud will now dress up like a woman! Sadly, you'll need lots of stuff.
Dress
To get a dress, go to the dress shop. From there, you will need to head north, to the bar. Talk to a man sitting alone at a counter on the right-bottom side. He'll get excited about Cloud, and offer to make a dress, but you'll need to tell him what you want.
Wig
To get a wig, you'll need to go to the gym. You'll praticipate in a squatting game. Play this game, win, and get a blonde wig!
From here, you can go on straight to the mansion or do some more stuff. If you want to see some other silly things, well, continue on!
Colgne
You'll need to eat at the restaraunt. When you do, you'll get a Pharmacy Coupon. When you recieve it, go to the pharmacy and get an item. Get a Digestive and take it to some lady in the bathroom of the bar. You'll get a sexy cologne for these efforts.
Tiara
To get a Tiara, go to the Materia shop. The man will tell you to go and sleep at the inn and bring something at the vending machine. Go to the inn and sleep for 10 gil, and at night, you'll go to the vending machine. Buy something, and the next morning take the item to the man in the materia shop for one of these items:
200 Gil - Diamond Tiara
100 Gil - Ruby Tiara
50 Gil - Glass Tiara
Lingerie
On the first Wall Market map, talk to the man at the bottom right of the map and get a Member's Card for the Honeybee Inn. Show your members card to the man in front and you'll go in. You'll be able to go in one of the rooms on the left side. You'll get Bikini Briefs if you go to the group room or Lingerie if you go to the &$#% Room. Afterwards, go to the Honey Bee Dressing room to get some makeup.
Don's Mansion
Head back to the dress shop and change into dresses. After, go back to Don's mansion and you'll head inside, when told to wait, head upstairs and then to the farthest room on the left and go down these steps into the basement. Some conversations will go on. Don't forget to pick up the item there!
Don will call all the woman into the room. If you got the Silk Dress, Blonde Wig, Sexy Colgne, Diamond Tiara, lingerie, and makeup... don will pick Cloud! If you didn't, well, he'll pick one of the other two. If he doesn't pick Cloud, you'll have to fight some guys, but either way, you'll end back up in Don's room... where he will open up a track door and send you on your way.... down...
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