The Day My Co-Worker Got a Sex Change
A comedy article
by Brock Sampson 649 6 11/13/2006 08:30 PM 1567 views
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This one is going to hurt. It's going to hurt all of us. It's the weirdest work-related story I have, and I've been thinking about how best to tell it. I don't think there really is a best way, so I'll just get right down to it.

Part One: The Most Surreal Staff Meeting Ever.
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 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 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 without either bursting out in uncontrollable nervous laughter or, in extreme cases, projectile vomiting. This was something new to all of us. At least I think it was. You never know.
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 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. Granted, it's usually not a set of perfectly executed French tips, but whatever. Frankly we were past giving a Shakespeare, and stopped trying to figure it out. We all thought he was a dick, anyway. The one thing we didn't even consider was that the goatee was his final attempt to butch it up a notch. He was at the last point on the decision tree, and it looked something like this:

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.
I had some questions, but I didn't end up having to ask them. The one answer about the private bathroom downstairs pretty much did the trick for me, since most of mine were of that sort. I was thinking about the configuration of our men's room. We have no privacy wall between the two urinals, and it might be slightly awkward to find yourself standing at the urinal next to a woman with her dress hiked up and her dick hanging out. That would make for some pretty Frosted up nightmares, I'm sure.
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 Shakespeare.
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.
As for me, I lead a sheltered life. This is the closest I had ever been to an actual, live, honest-to-God transvestite. Granted, he was on his way to full sex change, becoming a woman and all that, but as of right now, scuttlebutt had it that he was still packin'.
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.
I have to say the strangest part was the hair. He had obviously been watching too many 80's movies on his strange and twisted journey, and picked a very suspect hairstyle to ultimately go with. This was pre-op, and he was also still clearly a male, slinky dress and heels notwithstanding. By 5:00 pm, he looked something like this:

Seriously. His hair was exactly like that. It wasn't blonde, but other than that, this picture is dead nuts on. Probably by now, dead nuts off is closer to the literal truth. Anyway, we called it the SWOOP. I'm pretty sure that load of hair on the one side was responsible for causing some of that sideways listing and stumbling with the stilettos. The weight was throwing his balance off.
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. Every time you heard it wafting across the room, if you were a guy, your balls would shrivel 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 he didn't.
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.
Part two of our story starts with an 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 the optional 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. Once in a while, he'll stumble on something that shouldn't be out there, like bootleg music files, or bootleg videos, or sometimes porn. Normally, when he finds something like this, he'll check out a handful of the files, determine that he's correct in his suspicions, then pass it off to the security department to see if they want to kick off any sort of internal investigation.
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, red 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 had been 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. 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 where I work anymore. Although they were good for laughs, I have to say I don't miss either of them. There's only so much diversity I can stand, and I'm pretty much full up.
Wherever they are, I hope they're happy. Maybe Roberta will find a nice guy and settle down, and maybe Bra-dude will work things out with his wife, the attorney.
I suppose anything is possible.
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Like This? Rate It!
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Funny
87 votes
3.9
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Hilarious
1 votes
4.0
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Millie 116,988 28
11/13/2006 09:13 PM
Meh, it was all right, but my work stories are funnier.
I worked with a woman who was formerly a man at the tampon factory. She pretty much looked like a guy with bleached blonde hair and a perm. She wore skirts and make-up, but she had a man's body, really.
Someone told me when she was a man she'd been married, and she was still married, and her wife had worked at the factory, too, but didn't anymore.
I worked with someone else who used to be a man, too. She also continued to prefer women after her sex-change.
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0 votes
0.0
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John Hargrave 128,751 73
11/13/2006 10:29 PM
I was literally laughing so hard at this article that I was making my testicles retract into my body, much like Roberta.
Beautiful job. We will be seeing more of this Brock Sampson.
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0 votes
0.0
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Hammerhead 59,399 14
11/13/2006 10:31 PM
Well, John, after all the Shakespeare you do for your articles, it's amazing your balls haven't just fallen off.
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0 votes
0.0
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Mr. Slinky 28,185 10
11/13/2006 10:50 PM
I've read this online somewhere else before, but it's still funny as hell.
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0 votes
0.0
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The Jerk 6,311 9
11/13/2006 11:37 PM
Who in the blue hell is Brock Sampson?
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Chuckleworthy
1 votes
2.0
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Hammerhead 59,399 14
11/13/2006 11:47 PM
The guy who wrote this article, duh.
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0 votes
0.0
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Brock Sampson 649 6
11/13/2006 11:49 PM
You know. Me.
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Side-splitting
1 votes
5.0
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Thud 68,497 19
11/13/2006 11:50 PM
You look kinda flat.
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Side-splitting
1 votes
5.0
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Roofie Raccoon 56,688 10
11/14/2006 08:06 AM
Very well done. That was an enjoyable story.
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Side-splitting
1 votes
5.0
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Dogs Akimbo 211,584 32
11/14/2006 08:43 AM
Apparently, he was a woman trapped in a man's body, but also a lesbian.
He did it to get chicks? Huh.
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0 votes
0.0
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Highlight me, but in Communist Russia... 14 6
11/14/2006 10:01 AM
Pfft. I hate guys that do that; or indeed Girls that do the same thing.
Now, I'm Gay myself -avoids assortment of objects thrown at him- but no-one that knows me in real life knows it; exept the people I've told. Even they said they never would have guessed.
Most people I know are homophobic. I'm not the kind of person that walks around waving my hands around talking like a girl; neither do I act like a stereotypical 'Gay guy'.
I just find people that do that kind of thing DESERVE to be Gay Bashed to hell!
Then again, that's my opinion. :p
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Side-splitting
1 votes
5.0
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TacoCrunch: Ambushing GABbers under the mistletoe 61,976 36
11/14/2006 10:04 AM
1 - You're too afraid of other people's opinions to be yourself? Nice work! I'm sure you get a whole lot of dates gay bashing potential relationships.
2 - Emoticons = no good.
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Side-splitting
1 votes
5.0
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Highlight me, but in Communist Russia... 14 6
11/14/2006 10:33 AM
1 - You're too afraid of other people's opinions to be yourself? Nice work! I'm sure you get a whole lot of dates gay bashing potential relationships.
2 - Emoticons = no good.
If you're talking to me:
1. I'm not afriad to be myself, I am myself all the time. If people happened to ask if I'm gay, then I'll simply say yes. If they don't like it then it's their own fault.
2. I don't get a whole lot of dates; because I'm taken.
Sorry about the emoticon it's a habbit.
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Side-splitting
1 votes
5.0
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Chickens wonders is it 2008 yet? 286,539 61
11/14/2006 10:47 AM
Scuba could have so much fun with this. He could look over at your table during lunch, grimace, and ask if you really want to eat on that table.
Later, he could ask you if you really want to be using that particular computer mouse.
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0 votes
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istealllamas 0 6
11/14/2006 01:18 PM
The "decision tree" is Frost-ing hilarious.
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0 votes
0.0
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Ice Princess 171,275 14
11/14/2006 03:15 PM
I thought that rocked, Brock.
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Side-splitting
1 votes
5.0
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Stacy420 75 7
11/14/2006 04:08 PM
...interesting.
I've always wanted to be in a situation like that(the awkwardness, not the sex-changeness). I think I'd have a problem trying not to laugh at something like that.
...I mean, come on! You lost your weiner!
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0 votes
0.0
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Bankey 70,843 10
11/14/2006 04:09 PM
The 80's chick with the big hair and 5 o'clock shadow alone made this a worthwhile read!
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Side-splitting
1 votes
5.0
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Nowhereleague 10 6
11/14/2006 06:58 PM
More creepy Tranny stories:
I used to be a police beat reporter for a small-town Alabama newspaper. Alabama is not especially known for its tolerance to certain types of weird but this particular town seemed to breed it. Think "Picket Fences" + "Deliverance."
Anyway, one of the officers, Kenny (Also affectionately known as Pig-F****R by the other officers--true story, but a different story altogether), had a secret admirer. The admirer sent large gift baskets full of homemade baked goods, fresh-cut flowers and candies. Each basket had a hand painted card that read "To Kenny, from your Lemon Lover". (I swear this is all true)
One day the Lemon Lover showed up at the police station in person bearing gifts and greatly resembling Arnold Schwarzenegger in a sun dress -- assuming the Governator was a post-op tranny with large fake breasts and long blonde hair.
Rather than freaking out and running for the hills, Kenny thanked the muscular he-she beast for all the gifts and, as of 2004, the Lemon Lover was a weekly visitor to the station.
I still wonder today if Lemon Lover still visits "Pig-F****r", but only after I drink too much mescal and eat Kraft Macaroni and Cheese just before bed.
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0 votes
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Nowhereleague 10 6
11/14/2006 07:07 PM
Sorry for the long post
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0 votes
0.0
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Nowhereleague 10 6
11/14/2006 07:07 PM
Hmm, how many people noticed the "Back to Man Page" button?
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0 votes
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Werehampsta 6,375 8
11/14/2006 08:34 PM
Also affectionately known as Pig-F****R by the other officers--true story, but a different story altogether
A true story in which he Frosts pigs?
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0 votes
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Pisserbyer 104 6
11/15/2006 01:48 AM
In the top most picture, the one on the left is pretty hawt.
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0 votes
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Dogs Akimbo 211,584 32
11/15/2006 01:50 AM
A true story in which he Frosts pigs?
Yeah, you should have told that one.
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Funny
1 votes
3.0
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ringworm 68,315 13
11/15/2006 05:07 AM
... affectionately known as Pig-F****R by the other officers...
um, they're cops. was he the office slut?
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Side-splitting
1 votes
5.0
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Nowhereleague 10 6
11/15/2006 12:18 PM
According to the police chief, the guys at the station were talking about another of the towns delightful residents, A guy named Scott who used to get drunk, go out to the local watermelon patch, cut a hole in a melon, and hump it like a vietnamese prostitute.
Scott was arrested on night and, at the time of the arrest said, "I ain't hurtin nobody and at least I wudn't Frostin a goat."
Later that evening the guys were joking about what he said, and Kenny spoke up about knowing someone who screwed a pig. Since "I know this guy" was as specific as he would get, the other officers started joking that it was him and the name stuck.
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0 votes
0.0
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Nowhereleague 10 6
11/15/2006 12:20 PM
Now was that little story really worth it?
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0 votes
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Dogs Akimbo 211,584 32
11/15/2006 03:13 PM
It was no worse than the other one.
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Side-splitting
1 votes
5.0
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TK in the Straw 98,000 37
11/15/2006 03:49 PM
Somehow I doubt Rob went through with the surgery. I think I read once that the screening process is stringent - the surgeons make damn sure that this is what you want to do. It doesn't sound like this guy really wants to be a woman - he's just severely Frosted up in the head.
Loved the decision tree.
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Side-splitting
1 votes
5.0
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The Lee 5 6
11/15/2006 10:41 PM
I usually like the stuff posted here. But this was pretty unfunny. Well the porn in the building part was amusing. But another persons gender identity/expression is none of anyone elses business. I have a number of trans friends and their gender identity and worrying about reaction from people likke you cause them huge amounts of stress. Trans people have a very high suicide rate. Oh and trans day of remberance is monday. Look it up.
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0 votes
0.0
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The Lee 5 6
11/15/2006 10:42 PM
@ "TK in the Straw"
To get on the hormones and to get permission as the surgury its required to live as the gender you wish to be for at least a year.
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0 votes
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Sakon 595 9
11/15/2006 10:58 PM
That was one of the funniest articles I have ever read. This is going straight into the favorites folder.
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Side-splitting
1 votes
5.0
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Dogs Akimbo 211,584 32
11/15/2006 11:43 PM
But another persons gender identity/expression is none of anyone elses business.
Nuh uh.
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Hilarious
3 votes
4.3
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Brock Sampson 649 6
11/16/2006 05:57 PM
"I usually like the stuff posted here."
So you're fine with rape, eating babies, bestiality, racism, and assorted lewd and crude behavior, but this article gets your panties in a twist?
"But another persons gender identity/expression is none of anyone elses business."
He pretty much made it everyone's business, whether they wanted it to be their business or not. If you want to write a funny article about short straight guys with small penises, I promise I won't be offended.
"I have a number of trans friends and their gender identity and worrying about reaction from people like you cause them huge amounts of stress."
He caused me way more stress than I caused him/her. He was a total dick before he was a girl, and he was a total dick after, which was pretty ironic.
"Trans people have a very high suicide rate."
I could go for the low-hanging fruit and say "not high enough" but that would be crass and uncaring. Then again, I am posting on Zug.
"Oh and trans day of remberance is monday. Look it up."
I did, and I agree, nobody should be killed for wearing a dress and high heels. I will go on record as saying I oppose violence towards transgendered individuals. However, I also oppose people getting in my face at work for no reason other than to make me uncomfortable. Do I want to kill him? Of course not. Do I find it amusing and baffling and do I want him to get the hell away from me and stop trying to intentionally gross me out? Of course I do.
Sorry you didn't care for the story. Perhaps the next time I have a tranny in my cube at work, I'll think back on what you said and feel better about about getting sexually harrassed by a guy in a dress.
Or not.
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Side-splitting
1 votes
5.0
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hisboyelroy 10,621 13
11/16/2006 06:09 PM
haha, "trans day of rememberance"? what, do we remember all the chicks with dicks that fought for our country? perhaps fly a blouse on the flagpole? have a moment of limp-wristedness in honor?
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Chuckleworthy
1 votes
2.0
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theinnerlight 2 3
06/17/2009 02:30 PM
Just about killed me with this one: "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."
There needs to be a sex change boot camp available for this purpose.
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