I bet he's the kinda guy that'd fuck a woman in the ass and not even have the god damn common courtesy to give her a reacharound.

I want a donut.

When he would hook up with prostitutes he unknowingly hooked up with trannies on a few occasions. The joke is he realized it once or twice but still ended up finishing the deed, so saying they are "ladies" is the joke so what he did sounds less gay. And since it happened on a few occasions he talks about it on stage and just goes with it. Go look up some clips on youtube.

I'm assuming Joe caught shit because he legitimately wants to have sex with a transsexual knowing they have everything but Jimmy supposedly didn't know or was tricked.

From what I've gleaned, there's three things things going on here. One is him and his friend sucking eachother's peckers under a porch as a child. Another are his encounters with transgenders, however rare or accidental, are at the forefront of his mind. The last is his curiosity towards getting pegged in the arse by a girl with a strap-on. From what I can recall, he's said he suspects only having fucked one post-op transsexual, so we can only assume his transsexual endeavours have been with the pre-op variety.

He openly admits to being addicted to sex, and his multifarious tastes therein, however any penchant he has for ladyboys appears to have not been explored to it's fullest extent, as it occupies more of his ludicrous humourous thoughts, yet his self proclaimed obsessive behavior toward his straight sexual encounters with "good eggs" is referred to in more sober terms. i.e. it's real enough to be funny, but it's only a curiosity.

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Probably the same reason Derosa is so into bailey jay....it would be nice if chicks were really into sex and being dirty, but the only ones that are have a nice delicious pecker.

Feature not a bug

My theory on Norton's jokes about transsexuals are that they're like his jokes about being an actor or a great actor. It's an big exaggeration of a tiny reality, an exaggeration so big it's almost sarcastic.

OP: Who cares?

Joe catches shit because it BOTHERS JOE. If it didn't bother Joe they'd stop. They make fun of Bob Kelley and Patrice and even Jimmy for being floppy titted fat monsters, even when Jimmy isn't really fat and Patrice really never gave a fuck and had diabetes!

http://www.ts-baileyjay.com/

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probably enjoys sex with trannies a lot more than he's willing to admit

what? lol he's admitted to it pretty clearly a bunch of times. joe just got to jimmy's level in the past few months haha.

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he mentioned going to a tranny club once - no idea if he went again

They called it a "tranny club" but if you listen to the clip, it was clearly just a drag show. There is a difference.

yeah, he made it sound like a tranny strip club

He used to cruise transexuals in the meat packing district and one of them stole his glasses. He had to ask a cop to get his glasses back and then the cop shamed him to leave.

that too - the tranny club was about a year ago as i recall

He copped to accidentally fucking a tranny prostitute once (you could probably find it on youtube). After that it just became a running bit. He's not actually into it.

He is into it. I dont think he fucks them on the regular but he knows a hell of a lot about them. And when he was hosting the AVNs years ago he reluctantly turned down a trip to the bathroom with one of the porn stars (who iirc ended up getting arrested for allegedly blowing a guy in said bathroom). He plays it up in his act and on air but he is no stranger to the scene.

I dont think he fucks trannies, only enjoys the idea of it / watching their shows (e.g. with Colin Quinn)

The onyl instance i know of him fucking a tranny was when he was living in Jersey and picked up a hooker, fucked her and didnt know it was a tranny until years later