I'm going back to old school. As I recall, and correct me if I'm wrong, the first World's Worsts came about from the new forumusers characters. I have one with Kaufman in my comics ("Worst thing to say to a guy holding a cat"), and I think the other target was crabby. If it was Kajun, I sincerly appologize, but you're going to do it again anyway, BECAUSE:

Worst thing to say to a guy in a skirt

WW#5: Worst thing to say to a Guy in a Skirt by attitudechicka 2-06-04

You should really shave your legs.

This is the topic I chose. Don't like it? Bite me.

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Mediocrity at its most average.

World's Worst Thing to say to a guy in a Skirt by Drexle 2-06-04

Hey there. Woah! what's up with the skirt?! It's not a skirt, wanker! You know, dressed like that, you look exactly like my ex girlfriend. Even with the bulge? No... hers was bigger.

Well I like it, can I do something instead of biting you?

WW#5: Cuz I'm freeeeeee..... free baaaaallin' by Beaz 2-06-04

I feel so free without boxers on! What's your problem? Every time the wind blows I see your balls.

WW5: There's this guy in a skirt, right? by mmyers 2-06-04

The dress is nice but the pumps are a bit much. When is the rest of the drag queen parade going to show up? Save it for the "Scots gone wild" video, Julie. Get in the Police car and show a little leg while you're doing it.

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Peeing sitting down is the gift you give yourself.

WW#5: Kilty as charged by shark_energy 2-06-04

Somewhere in Scotland What thee hell yee got that skirt on fa ya big jessy!

WW5: World's Worst Things to Say to a Guy in a Skirt by fpd 2-06-04

1. Hey, I think you'd look even sexier in a mini-skirt. 2. You look like you're just my type. How about a little hanky-spanky? 3. Pull up that skirt, and I'll give you the best head you've ever had.

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FPD is the foremost plague on discussion boards. Do your part to stomp out FPD.

WW5: Call a Kilt a Skirt, Cause a Scot to Kill by Xuanwu 2-06-04

Imitate Marilyn Monroe, and I will kill you. That looks so much like my skirt! Though mine's shorter, and it came with a free riding crop. I can see your knickers. Mmm...

WW5: With curly fries. by jes_lawson 2-06-04

Hey, McDonald! I'm not a McDonald, I'm a McFirefly Then what's with the quarter-pounder under your kilt?

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Please replace the handset, and try again.

Since my last entry featured only men, I did another one that focuses on women.

WW5: Worst Things for a Woman to say to a Guy in a Skirt by fpd 2-06-04

1. Do as I tell you! I'm the one who wears the pants in this family. 2. That's such a lovely dress. You must tell me where I can get one just like it. 3. Wanna go out on a date? Sorry, I don't date other women.

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FPD is the foremost plague on discussion boards. Do your part to stomp out FPD.

Worst thing to say to a guy in a skirt by obijo 2-06-04

Welcome to prison.

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I ate a hooker half a bottle of knife.

World's worst thing to say to a guy in a skirt. by ElTigreMask2K 2-06-04

I like your skirt.

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Menthol?

Worst thing to say to a guy in a skirt by dcomposed 2-06-04

Hi, I'm Bazilla.

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Batman created by Bob Kane

World's Worst Thing To Say To A Guy In A Skirt by Rabid_Weasle 2-06-04

No words need to be said.

World's Worst Thing To Say To A Guy In A Skirt by Rabid_Weasle 2-06-04

You're dripping all over the floor...

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Poop.

Did You Say A Guy In A Skirt? by graykane 2-06-04

Tell me about San Francisco. Hardcore dykes like us just don't get no respect. Oh yeah, does that feel nice?

Guy in a skirt by graykane 2-06-04

Your knee is so soft.

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i want to piss on you

Commercial that probably won't ever be shown by EvilZak 2-06-04

Boxers or briefs?

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AFROMANS MOVE

WW #5: Peeping Tom by NooniePuuBunny 2-06-04

Man...lookit that ass on her. I just gotta take a peek. What the--   !     !   Talk about false advertisement...

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I will rate you hard, and unendingly.

WW#5 : ...you don't know where that finger's been. by niteowl 2-06-04

Now I see why you wear that ridiculous skirt, it's easier for you to scratch your ass.

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Think classy, you'll be classy.

Worst thing to say to a guy in a skirt by boinky33 2-06-04

OMG!!! UR WANG SI HANGIN' OUT!!!!11

WW V: Skirting the Issue by kaufman 2-06-04

Let me see ... Why yes, it does make your ass look fat. Hey man, got any pants you're not using? Mr. President, I'd like to ... OH MY GOD!!!!

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ken.kaufman@gmail.com

Some entries have been disqualified, but they made me laugh, so you can still hope for a "breaking the rules" honorable mention. In the meantime, something I couldn't resist:

Worst thing for a guy to say to his kilt by attitudechicka 2-06-04

Kilt, I think it's over between us.

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Mediocrity at its most average.

Worst Thing to Say to a Guy in A Kilt. by Kevin_Keegans_Perm 2-06-04

Nice Kilt. Wanna Fuck?

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"Life Sucks, Then you Die. The bit inbetween isnt very funny either"

Worst thing to say to a guy in a kilt by boinky33 2-06-04

Excuse me, have you ever heard of upskirt.com?

Worlds Worst Thing to say to a Guy in a skirt by ElTigreMask2K 2-07-04

How'd you like to be my very special elf?

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Menthol?

An oldie:

Great debates: Kajun vs. boorite by KajunFirefly 6-04-02

Hey man, your shoes are untied. These fuckers are always coming undone. Aww, man, I can totally see up your kilt when you do that! Sorry. I didn't tell you to stop.

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Dad was flammable

WW#5: Worst thing to say to a Guy in a Skirt by thisstinks17 2-07-04

Hey, where'd you get that, I'm trying to find a good anniversity gift for my wife.