So, this is fun.
I am a big guy, so the proceedure for me is a trifle bit different than some men.
I live in a very conservative area of Illinois, Rockford, specifically. So, dressing in drag had to be "allowed," at least tacetly. I did it on Halloween. The city is pretty intolerant of alternative lifestyles.
The Preperation
Early that day I spent my time in a JC Penny Outlet Store, looking for a bra, skirt, pantyhose (I actually wanted stockings and a garter, but I couldn't find any in my size), and a nice sweater to help conceal my bulk, and a men's long sleeved dress shirt.
My wife says that I have womanly legs, which is fortunate, because it offsets my really large bone structure. They're curvy. I shaved my legs, which took longer than I thought, about an hour. What? I never did it before. (I can tell you this, it felt awfully weird when the hair started to grow back and caught on the inside of my jeans.) I couldn't find shoes in men's 13 size that looked appropriate, so I wore my boots under the assumption that people rarely look at other people's shoes. At least most men, who were the main target of my observation. This year I have shoes that look like Candies, so if I decide to go again, I'll be prepared.
The bra was stuffed with toilet paper. The butt tape kind of itched after a while because I would sweat, so often I could be found rotating the TP around in the bra (size 48D) for maximum comfort. The sweater was nice and long sleeved. We chose this so I wouldn't have to shave my arms. I put on the bra, the dress shirt, then the sweater on top of it all, and cuffed up the ends of the dress shirt over the sweater's sleeve. It actually looked nice, IMO, but my boobs looked fake because of their perkyness. I probably could have solved this problem by wearing a simple white T-shirt under the bra.
The skirt and pantyhose went on last. I was hoping for a plaid skirt, for a more school-girl look, but couldn't find any, and we looked for a bit, so we settled on a simple black one, with sheer dark stockings. The skirt was kind of long on me, so I hiked it up to about mid-thigh. Under the covers, I wore tighty-whiteys, but I usually go with boxer shorts. That's not important right now, but what was important was this question:
To Tape, or Not To Tape?
Men generallly have penises. This is the way things are. When trying to pass ones-self off as a member of the gentler sex, things can go awry, such as unexpected penile excitement, or simply there may be a bulge where there should be a soft, flat area. I could find no acceptable method of restraining my member that may help, so, and I confess, I used Scotch Tape. I do not recommend this. It itched, and unless you are prepared, removal may be painful. Hell, movement may be painful. The tape's got your short hairs, no matter how careful you are. Although I was never a Boy Scout, I was a Cub Scout, so I have a vague idea about being prepared. I sweated a lot, as well.
But that's enough about my testicles.
Make-up was provided and applied by my then-girlfriend, now wife, who said constantly that she couldn't believe I was doing this. Shave the face, add mascara, eye liner, foundation, lipstick. Both me and my daughter are blessed with extremely long eyelashes. This helped. I already had long hair, so we lovingly combed it and put it up in pig-tails.
Then came the fun part.
Reactions
First reaction: My wife wouldn't kiss me when I was dressed up.
Second: I decide really don't look that much like a girl, at least my face doesn't. The rest of me is dead sexy.
Third: "Oh my God"'s from family members including my sister, mother, and step-father.
Fourth: People really don't like people who aren't like them. From a distance of more than, say, 10 meters, most people don't seem to notice. Women notice an impostor in their midst more readily than men do. I stayed quiet, so I really didn't have much of the male voice problems. As people came closer, at least for me, recognition of what I was approached, I'd say, about 70 percent. YMMV.
I scared the crap out of my 2 year old neice and nephew, too. They barely know me and any recognition of who I was immediately departed. My sister-in-law barely acknowledged it, though I'm sure she had something to say behind closed doors.
Other Observations
I felt sexy, at least away from any mirror. All curvy and other fun stuff. I am really envious of all the cool outfits that women can wear.
Around here there are plenty of gay people, and they seem at least tolerated, if not accepted; but there is a lack of transgender/sexual people. I know of one post-op (now female), but have never met her. She is constantly belittled when she is discussed. It's a possiblity that she's just worthy of contempt as a person, but most of the humor is based on what she is and how poorly she has adapted to her new role (still has a husky voice, etc.) and not who she is as a person. I find this unfortunate.
I had a lot of fun dressing up, and would like to do it again, but probably in a more open atmosphere of perhaps a larger city.