It all started with a plan for a Sim orgy. I decided to dress the whole neighborhood in lingerie and other sexy outfits. I had some downloaded skins for men that let me dress Senator Burnside in a corset and garters, a la Rocky Horror Picture show (from The Cloth Menagerie), and Mortimer Goth in a bra, hotpants, and little red shoes (from Emma's Skins, which alas is no longer up).
I knew that somewhere I had seen a skin of a hairy-chested man in a bikini, and I thought it would be funny to have Bob Newbie wear it. That turned out to be The Sims Gift Shop, which was hosted at The Sim Resource and not reachable, but someone e-mailed the creator (Indian), who e-mailed me the skin.
By then, I had chosen another outfit for Bob Newbie, but I think the bikini looks a little better on my Sim anyway.
Indian also sent me a picture of some male Sims in long dresses that he/she was working on and asked whether I was interested. I said I was, but I never heard back. That got me thinking, and I decided to experiment on my own. Thus began Project Crossdressing.
I had figured out how to rename .bmp files so that "fat" folk could wear some "fit" outfits (in fact, Senator Burnside's corset was renamed from a "fit" one). I thought I could probably do something similar to put men in gowns and skirts. I had to hunt a bit to find suitable meshes, but they're out there. I collected some meshes designed for robes, kilts, tunics, and togas and then, using trial and error, determined which ones would work with renamed female dress .bmp files.
My first attempt was simply changing a woman's long robe to a man's for Jimmy Garter, the first member of the crossdressing family. The mesh came from a skin for Ayatollah Khomeini (from SeNeCa's Wicked Sims); I don't remember where the red robe came from. Next, I simply renamed a woman's lingerie skin (by verylisa at Boutika) to fit the mesh used by the Rocky Horror outfit for Gary Garter and a woman's swimsuit (from Glamour Sim) to fit the B300MAFit mesh for Ru Garter.
When I was creating Ru, I first tried using a RuPaul skin I'd found, but frankly it made him looked too much like a real woman for my purposes. I wanted it to be obvious that these were men. So I put Ru in a swimsuit and later searched the Web for meshes that would let me dress my men in skirts. Go to Page 2 for my results.