I've been wondering lately what exactly the difference is between the way we reveal ourselves to an SO and the way we do so to a friend or colleague.
One of the big differences, for me, is that I can go much more slowly and gradually, over a much longer period of time, with friends and colleagues than I can with someone who shares in my personal life on a more intimate level.
If, at some point, you decide to, say, shave your legs, there's not much of a chance your wife or girlfriend won't notice. However, with colleagues or friends, that's not the case.
I take my own situation as a case in point. My colleagues know that, once in a while, I shave my entire body (facial hair included). At first, they were curious. I merely explained it away as something I enjoy doing for the sensuous feel of it. No big deal, right? Now, they still notice but hardly ever comment on it. Same with my fingernails, which I usually keep painted with clear polish. When they first started noticing and asking questions, I just replied that I'm proud of my hands and find that my nails just look better that way, especially when they catch a glint of sunshine or a ray of light. They don't ask anymore. Same goes for my hair colour. I've died my hair a few times since I began working there. I usually go for a shade darker than my own natural colour, say, "Midnight Plum" (very black with 'eggplant' highlights) as opposed to my own dark brown. Yesterday, in preparation for our office Christmas party, I dyed my hair "Deep Auburn," a very warm brown with reddish copper highlights. Which brings me to the reason for this post.
It seems I've taken another step toward full self-disclosure to my colleagues with the way I appeared at the party last night. A red silk shirt. (I've worn silk at work before--some of my male colleagues do too.) A pair of my ex-girlfriend's dress jeans (tight in the butt for a sexy look). My body clean-shaven. My hair dyed reddish-brown. My short beard trimmed Arab-style (a thin mustache and an even thinner line of hair along the jawline). And, to top it off (or, to top it under, I guess), pink satin panties in a floral motif and and all-sheer tan pantyhose underneath my jeans (this, despite my earlier misgivings about "underdressing" at one of our infamous parties). Well, people, I tell you: I was a "babe magnet"! The attention I got from some of my more eligible "bachelorette" colleagues just blew me away. Some of the women that had always been friendly enough towards me were now following me around. I almost felt hounded. Many of the guys were intrigued also. It was a good party.
At one point, after the buffet, I sat with two of my female colleagues, as they discussed push-up bras, manicures (one woman, at some point in the conversation, holding up my hand to further inspect my own fingernails!) and bikini line electrolysis. I participated in the conversation (of course, I did!) but I tried not to appear too eager or knowledgeable about any given subject. It was heavenly. Later, another one of my colleagues came to drag me out on the dance floor when the DJ slapped Neil Diamond's "Girl, You'll Be A Woman Soon" onto the turntable and held my hands and looked me in the eye as she mouthed every one of the words to the song while we danced. That's when I started clueing in that something was up.
I figure that my crossdressing is probably the worst-kept secret at work; my colleagues never push me for details (they're respectful that way) and, from the occasional wink in my direction when the subject comes up in a general discussion, they seem to be very accepting of the whole transgender scene.
Understand that my gradual "coming out" is taking place very slowly; I've been working there for four years now and I've been dropping hints (verbal or otherwise) for at least that long. It seems to be working.
Amusing highlight of the evening last night: my boss led me to the buffet tables and asked me to breathe in some of the spicy aroma of the food laid out under the heat lamps. When I did so, he said, "okay, I just needed to confirm that my eyes weren't deceiving me." The place was very dark, except for the heat lamps and, when I leaned over, he saw that my hair was, indeed, reddish. He said, "One question: Why?" I answered, "Because I can and I did." That was as good an answer as any, I guess. He left me to go to the bar, shaking his head and smiling.
Anyway, I think the day is fast approaching when (possibly at one of our "full house" monthly meetings), I'll just make it a special point on the agenda to come forth more fully as a crossdresser. We'll see. I'll keep you all posted.
Love,
CJ
Egad! Now, I've got my panties in a twist over this. The plans are already becoming more concrete (discussions of costumes, etc.). What should I do? What should I do? 
About the calendar, if you feel insecure about the possibility of being outed to all and sundry, as you do seem to be (and as I probably would be too), then the "when in Rome" ploy would seem to be the best policy. You know the difference between a presentation well done and the "bloke in a dress" that you suspect most are considering. Can you not also carry off the joke without letting yourself do the job right, as Nancy alluded too? 
No sense of fun a'tall.
