Our manager called our entire team into her office, and she looked pretty ill at ease. We all thought there was bad news on the horizon, and she was going to announce restructuring and the subsequent layoffs. I don't think any of us had any idea what we were in for.
Turns out, the topic of the meeting was another member of our department who was out on vacation, and was due back shortly. This meeting was to prepare us for Rob's glorious return.
It seemed that when Rob returned on Monday, he was no longer going to be Rob, but instead Roberta. Rob was going to have a sex-change operation, and would be counting on all of us for our understanding and support.
He would not be a woman yet, but he would be wearing women's clothing, and makeup, and talking like a woman, and we were to treat him with all the political correctness we could muster
As this news was being relayed to us, suddenly, it all clicked.
A few months before, a bunch of us noticed that Rob was growing a goatee. We all figured that maybe he was trying to toughen up his image, since he was kind of a mousy guy. Since the goatee really didn't do much except evil him up a bit, we promptly began referring to him as "Evil Rob." This played out in a few weeks, and we didn't think too much of it after that.
The goatee apparently wasn't working out for him, because he shaved it off and started growing out his hair. We thought maybe he joined a band or something, and didn’t want to have both, since then he’d look like a mousy, evil jesus christ, which would not do.
The new rocker hair was coming right along, but we knew something was off when we noticed the fingernails. The nails were very nice --long, polished, and buffed to a subdued, yet sophisticated luster. At this point we had no idea what the hell was going on, but we figured that maybe the band thing was still the right answer, given that androgyny is a pretty common thing among rockers, and lots of rock guys paint their nails. 
So back to the infamous meeting. The obvious questions came up. Did we call him Roberta, or did the final whackin' have to happen before that? No, we were to address him as Roberta. Which bathroom was he/she going to use, and can I please use a different one? She will be assigned a bathroom on the first floor that nobody else would use. The questions went on for a bit in this vein.
We were all dismissed back to our desks to let this news sink in, and let me tell you there was some furious instant messaging happening after that shit.
So the next Monday rolls around, and everyone is trying like hell not to look at Rob as he stumbled into work wearing stiletto heels and a dress. Clearly, there was more practice needed on the "walking in heels" thing, because he obviously had no idea how it was done. He was walking exactly like an average guy would when suddenly deprived of the flat part of his feet, or placed on stilts for the first time. Kind of a rolling, shuffling, zombie-like gait interspersed with some quick, balance-catching jerks and almost-rolled ankles. I was waiting for him to hit the floor with a compound ankle fracture.
Initially, we were all pretty understanding. Shocked, a little freaked out perhaps, but understanding. He had some sympathy points built up, but he pretty much squandered them his first week back, mostly because of his newly developed in-your-face attitude.
The make-up job made Mimi Bobeck look reserved. He really needed a hand with that. I had frat buddies in college who dressed as women one Halloween and they were more convincing than this dude, even though he clearly had some face-work done while he was away.
The other insanely annoying thing was the artificially high, "girlish" falsetto he had adopted. It was like Mrs. Doubtfire had taken it up an octave. His high-pitched, tittering laugh was enough to make you think seriously about jamming sharpened pencils in your ears. Every time you heard it wafting across the room, if you were a guy, your balls would shivel just a little bit. You’d have to ask the women in the office what effect it had on them, but I imagine their ovaries twitched or something.
I remember commenting to a friend that he wasn't acting like a woman, or even a girl, and he clearly needed lessons very, very badly, because no woman I knew acted like that. It was like when he put a dress on, he got a lobotomy. Suddenly, there was this airhead, giggly schoolgirl act. I had never seen anything like it. Ru Paul acted more like a real woman than this guy. He had some serious learning to do, as I’m sure we all would, but he seemed to be heading in the wrong direction. When you decide to take the bullet train out of Normalville, you'd better know what track you’re supposed to be on, and it was painfully obvious that he did not.
It was completely awkward for most of us. Sometimes he would slip and lose the fake falsetto for a few seconds in the middle of a sentence and then things got really weird. In every single interaction with this person, it was like there was a gigantic pink elephant in the room that you were supposed to ignore, except this particular elephant just happened to be in drag.
Luckily, this guy wasn’t on my immediate team, so my interaction with him was limited. I heard the horror stories from other people, and I’m glad it wasn’t me. From what I hear, he got off on weirding people out. If he got a whiff that you were a little freaked, he would go out of his way to make you even more uncomfortable, to the point of sometimes becoming confrontational. If he had been wearing men’s clothing, he probably would have gotten his ass kicked multiple times. I’m not sure what the rules are on face-punching a Tranny, but I’ll look into that and get back to you.
A few of the women on the team even had the distinct pleasure of some one-on-one “girl talk” which I’m sure was a blast. I did find out later that he WAS on my team in a more general sense, in that he still liked women. Apparently, he was a woman trapped in a man’s body, but also a lesbian.
Chew on that tidbit for a while. Go get a snack, and when you get back, we'll talk about Part II
Part II: Enter the Bra-Dude
So here we are once more...
Right around this time, we enter part two of our story, which starts with my experience in the lunch line. There was this other long-haired dude who I never paid much attention to, who was apparently a friend of Rob's. They were in the same band, so to speak. I was standing behind him in line, and he was wearing your normal clothes for a business casual environment. Khaki Dockers, a button down white shirt and tie. As I was waiting to pay for my food, I noticed something else. That something else would be the outline of a pink lacy bra. Again, I try not to judge. I may laugh and point, but I don’t consider that judging, although some people might. Maybe he had manboobs and needed the support.
I started noticing him around more after that. You know how when you buy a new car, suddenly you start seeing cars just like yours everywhere? I’m not saying I identified with this guy in any way, but I just started seeing him around more after noticing the bra. I mean, I’ve never worn women’s undergarments. The closest I’ve come to this was finding a pair of my wife’s panties in the arm of my sweatshirt one day,but that was totally thanks to the dryer, and not to any inclination on my part. I was in this for the pure, comic aspect.
A few times, I saw him wear his hair tied back. With a pink scrunchie.
He was a different kind of dude, but after dealing with Rob, this was nothing. He was reserved, and didn't really advertise, although a pink bra under a white shirt is sort of an important mile marker on the highway of life for a guy. Once you pass that point, it's tough to go back. You’d have to go pretty far to even come close to Rob, but it seemed he was willing to do just that. Here's where things get pretty interesting.
My friend Scuba is a network admin, and part of his job entails cleaning up the abandoned crap that people store on the network and then never touch again. So he’ll do some searches by file size and date and file type, and clean off old spreadsheets and graphic files and what not. Once in a while, he’ll stumble on something that shouldn’t be out there, like bootleg music files, or bootleg videos, or sometimes even porn. 
So he was cleaning up some drives shortly after I had my pink bra experience, and he came across a directory stuffed full of jpeg files. This directory appears to belong to bra-dude. He checks out one of the files, and it’s porn. "Great," he thinks, like a cop who stumbles on a body in an alley. "I don't need this today." The first thing that’s odd to him is that it’s a male in the picture. He looks at a few more. All men. Hmmm. Not only porn, but gay porn. Then he realizes something.
He realizes that he knows the guy in this picture. It's bra-dude, and he's on a bed, arms over his head, dress hiked up, crank saluting at half mast. It is at this point in our story that Scuba goes blind. I'm kidding. He only wished he was blind.
The guy has a porn collection of himself and his man-friends stored on a company server. What the hell is he thinking? After Scuba realizes who it is in the pictures, he looks at a few more, and realizes something else.
Some of the pictures were taken in the building.
This guy was sneaking other guys into the building after hours and taking gay porn pictures of himself and the other guys, and then storing them on his network drive....
Scuba was completely traumatized. He seriously considered taking the rest of the day off. He didn't sleep for weeks. To this day, the images are burned into his mind, and I have it on good authority that on occasion he still wakes up screaming.
Incidentally, neither of these two work here anymore, one of them for obvious reasons. Although they were good for laughs, I have to say I don’t miss either of them. There’s only so much diversity we can stand, and I think I speak for everyone here when I say I’m full up.