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ROLLIN' TRANNY

A street parade is not complete without a rolling tranny bringing up the rear. Enjoy your daily dose of chicks with dicks everyone.

Type: Pics
Posted: 02/01/2010
SAY CHEESE! IT'S TRANNY TIME

Even the Trannies all around the world like to take time out and have a nice family gathering. What we have here is a Tranny family picnic. You know at least with this family, nobody has to feel like the different one. Every single one of them are just as fucked up as the other one.

Type: Pics
Posted: 05/21/2010
PAY THE TRANNY

If you're in Brazil and you get a blow job from a tranny hooker, you should probably pay up. Not getting slapped around by a chick with a dick, in front of a bunch of onlookers with video cell phones is worth the 30 Reais, even if the suck off wasn't.

Type: Movies
Posted: 08/18/2010
THE DAY WALKER TRANNY

I don't know how they do things in this country but over here trannys have a set of rules to follow. The most important one being that they are not allowed out during the day time. This day walker decided it would go for a stroll in the middle of the afternoon. It will be lucky if it's not found dead in a ditch somewhere. Never, break the rules of being a tranny, EVER!

Type: Pics
Posted: 04/22/2010
RENT A DATE : ONLY $5/HOUR

You might look at the title and be like god damn $5/hour is cheap as hell. Please! look at the fucking picture before you go buying it. This is the most disgusting looking tranny I have ever seen. For those of you gay enough to buy this shit, have fun!

Type: Pics
Posted: 08/05/2009
JUST PLAIN CREEPY

I've seen some bizarre shit but this one is up there on the fucking creepy list. Of course you know this is a dude dressed up like a woman. It just looks like he is going to whip out a chainsaw and begin to chop you up into little pieces.

Type: Pics
Posted: 08/13/2009
ONE STOP TRANNY SHOP

Where all your tranny fantasies come true in a matter of minutes. This place must be where people go to test out there sexuality if they are one of those "unsure" people. If you dress up like a chick and like it, well then you go from being Bert to Bertha and get a penis tucking 101 handbook.

Type: Pics
Posted: 08/17/2009
BIZARRE CENTAUR TRANNY

I am at a loss for words on this one ladies and gents. It looks as though this is a centaur tranny... Of course it is photoshopped, but the question is who would photoshop something like this. I mean they had the right idea with 4 boobs but they lost mean when they added a enormous cock to it. At least now we know the creator of this pic is a fucking freak.

Type: Pics
Posted: 05/06/2010
POPEYE THE FATTY

It looks as if Popeye has let himself go and transformed from that Spinach eating sailor to a tranny. A fat tranny with humongous saggy boobs at that. This just goes to show that if you eat enough spinach you will begin to go delusional and turn into this disgusting looking washed up tranny.

Type: Pics
Posted: 05/13/2010
MOBILE TRANNY FOR HIRE

Feeling down and almost out of self-esteem? Just fly over to China and order yourself a mobile tranny hooker. Within an hour you will have a gay hooker at your door ready to make everything all better.

Type: Pics
Posted: 07/01/2009
BACK ROOM TRANNY SURPRISE

Be careful while you are at work, as walking into the backroom can be a bit dangerous. You never know what exactly you are going to see. For instance, this guy walked in on his boss and what he thought to be the hot receptionist. It turns out the receptionist was a tranny and his boss loved the cock. What a weird day for that employee.

Type: Pics
Posted: 08/25/2010
BRAZILIAN TRANNY KICKS SOME ASS

If you ever find yourself soliciting sex from a tranny whore in Brazil, you should probably just pay what it's asking. If not, you just might get your ass beat in the middle of the street. I bet it gives a mean blowjob too.

Type: Movies
Posted: 05/07/2010
PICNIC WITH A TRANNY

Picnic with the cool kids who wear all black just wouldn't be complete without a tranny. This particular tranny did not even try and fit in by wearing all black. It is dressed in what looks to be some sort of bright red nurses uniform and high heels. I imagine a hate crime is in the works at this local picnic hotspot.

Type: Pics
Posted: 05/26/2010
TRANNY POWER!!!

That's a shemale tranny with an with attitude there.

Type: Pics
Posted: 04/01/2006
CRAZY SHIT TRANNY SURPRISE

What we have here is the story of a lovely young lady who walks to work every day. Each day she has to put up with these construction workers giving her a hard time. To get back at them she gets her tranny friend to dress up and walk her route. When the men start to yell at her she flashes them her goodies and they are shocked when they see a cock and balls.

Type: Movies
Posted: 03/19/2010
ALWAYS PAY ATTENTION FOR THE TRANNY BULGE

Don‘t let you eyes deceive you or else you might end up in a situation where you go nuts and kill a tranny halfway into blowing a load all over the shemales face. False advertising doesn‘t apply to sexual engagements.

Type: Pics
Posted: 11/02/2007
TRANNY TIME AT THE AIRPORT

Look closely and see if you can find out the one thing that doesn't belong in this photo. Of course you may thing that happily overweight guy is the reason for posting this picture. Take a second glance and you will finally see the tranny in his lingerie standing in the shadows. Why did they let that thing past airport security?

Type: Pics
Posted: 07/17/2010
JUMP TO TRANNY CONCLUSIONS

Sometimes people get excited and make decisions before getting all the facts. Like whether or not they are a shemale. There are some situations you may want to explore a little further before you wind up with your hands full of tranny wang.

Type: Pics
Posted: 08/08/2007
IS THERE SUCH A THING AS A CHUBBY TRANNY?

Most of the time you see trannies, they are all skinny and well, look like some sort of young boy, with tits. Not this uhh... chubby tranny. She's put on some weight and doesn't care who sees. Not only that, but she's got some weird red marks on the nipples from the breast surgery. Not stop Get-your-dick-chopped-off-ville.

Type: Pics
Posted: 04/27/2010
STOP! TRANNY TIME

Always fully inspect the lady before you start playing grab ass. That is something that this guy was never taught evidently. After some tongue action and a lot of ass handling, he realized that he was in fact hooking up with a DUDE! Man those trannies are some sneaky fuckers aren't they.

Type: Pics
Posted: 02/16/2010
ONE LAST SURPRISE

There is no way I could leave without sneaking in one more tranny picture.  Besides we all know your dirty little secret and honestly it's kinda weird.   Why so much interest once the chick has a dick?

Type: Pics
Posted: 03/14/2009
MY GIFT TO YOU ALL

Happy Friday the 13th everyone. Enjoy this lovely picture of two smoking hot....Trannies! It was only a matter of time before the tranny pics made a come back.

Type: Pics
Posted: 11/13/2009
THE TRUTH BEHIND OBAMA!

I fucking knew it all along! Check out Obama before he had his tranny operation. From stripper to president, and all it took was a flight to Taiwan and a penis implant. Simply Amazing.

Type: Pics
Posted: 09/17/2009
ADD A DICK SURGERY RESULTS IN PREGNANT TRANNY

This looks like shit some straight out of the Alien movies. You know where the aliens implant themselves in the stomachs and then pop out spitting acid all over the fucking place. Either that or this tranny managed to get pregnant after they had the "add a dick" surgery. Either way this is all sorts of fucked up.

Type: Pics
Posted: 04/14/2010
CRAZYSHIT TRANNY VIEWERS CHOICE AWARDS

And the choice for the hottest chick on the crapper goes to??? Well this really isn‘t a chick, it's a tranny, so I guess we aren‘t sure who the hell won. All we know is you guys voted for this shemale so here ya go!

Type: Pics
Posted: 08/31/2008
BIZARRE TRANNY SHOW

I have never been to Las Vegas but if this is the type of shows they have there, I am content on never going. I honestly have no clue what the fuck is going on here. I think this is a dude who had his dick removed and surgically added a vagina. Why anyone would ever want to do that is beyond me. It really just creeps me out looking at this picture. I hope you all enjoy it.

Type: Pics
Posted: 07/26/2010
SURPRISE! SURPRISE! TRANNY SURPRISE

Why is it that they give the ball wielding shemale tranny the mic every time?

Type: Pics
Posted: 03/03/2007
ASS OF THE DAY

I had to make up for the fat ass I posted yesterday. So here you all go. Hope you enjoy this ass a little bit better than the one from yesterday.

Type: Pics
Posted: 01/15/2010
NICE TITS AND....

BALLS! Yeah, another tranny picture from me to you all. I hope this ruins your day just like it has mine. Damn trannies are getting sneakier and sneakier.

Type: Pics
Posted: 07/06/2009
DO YOUR BALLS HANG LOW (REPOST)

SURPRISE! It has a cock and balls. What a fucking concert this tranny put on, I hear it will let you touch it if you have backstage passes. Enjoy!

Type: Pics
Posted: 07/10/2009
MAN WOMAN OR TRANNY? YOU DECIDE

I am confused on this one. I'm not sure if it's a man, a woman, or a tranny? Sure the hair on the chest says man. But we all know women can be hairy too. Then there is the boobs or moobs, if you will. The face says man too. I'm going to go with tranny then. Your thoughts?

Type: Pics
Posted: 05/02/2010
SCHOOLGIRL TRANNY

At first things look ok, then you look down and see a penis! Shemales... Not so much. So remember when you are over in the Orient looking for young hookers, to give them a flat hand first to make sure they are not trannies.

Type: Pics
Posted: 09/22/2005
HOOKING FOR JESUS

It seems like Jesus does support hookers after all. This tranny hooker seems to believe so and to show its appreciation it is hooking for Jesus. All proceeds earned from the hooking for Jesus campaign will be donated to your local church.

Type: Pics
Posted: 05/28/2010
YEAH, FUCK THAT WATERMELON

This isn't your run of the mill watermelon fucker here. He's got tits. That's right, it's a tranny fucking a watermelon. Enjoy!

Type: Movies
Posted: 06/22/2010
IT'S PEANUT BUTTER TRANNY TIME

WTF is that mark on the inside of that trannies leg. Is that a growth? No I am not talking about the shemales penis.

Type: Pics
Posted: 02/02/2007
THE LADYBOY OF THE YEAR PAGEANT

What do these three lovely ladies have in common? They are not ladies. They are shemales. Thats right these 3 ladies err dudes are the winners of the Mrs. Tranny contest in Thailand. I am pretty sure they don‘t call it Mrs. Tranny Thailand though.

Type: Pics
Posted: 06/01/2008
MORE THAN MEETS THE EYE

I love to crop out thumbnails of women who‘s boobs where artificially created and actually have a penis. This way all the people who would normally skip the tranny pic get tricked into thinking they are actually seeing a hot chick when it‘s a dude with tits.

Type: Pics
Posted: 07/09/2008
MORE THAN MEETS THE ONE EYED MONSTER

Believe it or not there are a ton of dudes out there waiting to hang out and get felt up by a shemale. If your not into your lady friends having bigger penises than yours you might wanna stay home or turn the lights down low to keep the laughter to a minimum before you see this tranny.

Type: Pics
Posted: 03/22/2008
TRANNY KICKS HARRASSERS ASS

If you ever plan on picking a fight with a dude dressed up like a woman you need to make sure you can kick his ass.  Otherwise you are going to be filmed and embarrassed in front of the entire world.

Type: Movies
Posted: 05/21/2008
YOUR TRANNY SCHOOLGIRL FANTASY

You better study long and hard before you go running off into a room with a bunch of schoolgirls. Afterall if they are all shemales your gonna have some trouble fighting off ten horny ones with dresses on.

Type: Pics
Posted: 08/01/2008
HORSE PENIS TRANNY

I decided to be nice this time and not fool you into clicking on the picture.  As much pride that is taken in tricking everyone I just had to come clean.  Oh yes and before anyone asks that trunk looking thing in the penis area is real.

Type: Pics
Posted: 08/13/2008
NAKED BY THE POOL

Attention deficit disorder is something that probably affects a large portion of the population and that‘s why it took a few seconds to realize this was a tranny. The problem is you are only getting bits and pieces of information when you need the whole picture to make a clear judgment on whether or not it's a shemale.

Type: Pics
Posted: 11/09/2008
TRANNYTASTIC MONDAY

While Monday is mostly known for it's glorious User Boobs, today I am going to throw a little tranny in the mix. I hope you all enjoy this trannytastic Monday.

Type: Pics
Posted: 08/02/2010
MINI SKIRT WANG HANG

You have to be careful when your around certain types of chicks. Especially the ones that have wangs hanging out of the bottom of their skirts. Enjoy the tranny on this lovely Sunday.

Type: Pics
Posted: 07/26/2009
ONE CONFUSED TRANNY

Trannies have this special little thing that makes me wanna throw up. It's not so much that I don't like them but something about boobs and penis to make a shemale mixed together that makes straight dudes really dizzy.

Type: Pics
Posted: 12/11/2006
PUTTING THE LADY BACK IN BOY

Our goal here at CrazyShit is to gain your trust so we can spring a shemale ladyboy on you that makes you question your sexuality. Sometimes we don‘t even tell you it's a tranny which makes you secretly gay so stop being such a homophobe.

Type: Pics
Posted: 09/24/2008
WHEN TWO HOT CHICKS MAKE OUT WHAT COULD GO WRONG?

Ok, so it's not really two hot chicks, more like 1.5 chicks. Is it weird that this kinda is hot? If that's wrong I don't want to be right!!! Click here for more he-she/she action!!!!!

Type: Movies
Posted: 05/29/2008
GUESS WHO'S THE TRANNY

Those guys are going to feel bamboozled when they go to gang rape that bitch and find out that she is a transgendered cross dressing penis wearing man. Sucks to be inmates with a woman packing heat.

Type: Pics
Posted: 01/17/2006
A FACE ONLY A MOTHER COULD LOVE

A mother and..a dude with shit growing out of his fucking neck. It's a midget tranny pic, what else can I say? Enjoy fuckers.

Type: Pics
Posted: 06/02/2009
TRANNY GETS RUNOVER BY TRUCK

As if it wasn't bad enough that you were standing on the side of the road in womens clothing a truck comes driving down the road and knocks you the fuck out.  Hopefully it wasn't going over 40 or else your chances of living are about 20%.

Type: Movies
Posted: 03/01/2009
FAST FOOD TRANNY

Ever feel frightened at who exactly is behind closed doors, making your food? Well your worst nightmares have finally come true. It seems McDonald‘s loves to franchise out to trannies. At least with this one they are forthcoming about what they serve on the menu. Order at your own risk here fellas, you may just end up with an extra order of cock with your Big Mac.

Type: Pics
Posted: 04/01/2009
MS PAINT CONTEST WINNER: TRANNY GETTING FISTED

This is last weeks winner of the MS Paint Contest, Titled: Tranny Getting Fisted. The winner, Buddernutts, got himself a crazyshit.com shirt. I don't know what you are waiting for, get your asses to the forums and start getting your drawlings in today! We're running one a week, from Tuesday to Tuesday.

Type: Pics
Posted: 11/21/2006
TRANNY MIDGET WINEHOUSE IS BACK AGAIN

Seems like the forces of weirdness just couldn't keep this little midget away.  This time around he/she pulls out all the stops with nipple tape and all.  That's right I said nipple tape.  The strange part is he/she has the same sized boobs as the real Amy Winehouse.

Type: Movies
Posted: 05/07/2008
HOT NAKED LADIES OF CARNIVAL

Book your tickets now for next year's Carnival. I bet it's a great fucking time, with all these hot asses walking around, I can't see how it's not a good time. I'm sure there are a lot of dudes just fapping all over the place. Tell me that #7 doesn't kinda look like a tranny? If it wasn't for the vag, I would have gone with she's a tranny for real.

Type: Pics
Posted: 02/20/2010
HOT ASS SURPRISE

Enjoy this hot ass surprise, brought to you by Crazy Shit.

Type: Movies
Posted: 03/18/2010
TIME FOR A LITTLE WET AND NAKED FUN IN THE SHOWER

Well, fun sure, if you are into naked, wet chicks with dicks. Sorry if I fooled you all into thinking this was actually real, hot chicks playing with each other in the shower. I hope you all enjoy.

Type: Pics
Posted: 04/08/2010
TRANNY INCEST MASTURBATION CARTOON

See More Fucked Up Hentai If you are into Hentai porn, this is the site for you. They have men that are turned into shemales that can only masturbate. Make sure you watch the whole video here because they throw some twists and turns on you. Like that they are brother and sister, but not by blood. The dude wants a strap on. Uhh there's so much stuff I had to watch it twice. See more Fucked Up Hentai Porn

Type: Movies
Posted: 10/20/2009
THIS IS THE CREEPIEST VIDEO YOU WILL SEE ALL DAY

With out a fucking doubt you will not see another video that is creepier than this. From the getting a anime tranny mouse pad to the horse head, to the well, licking of the mouse pad, it doesn't get any creepier. Ohh bonus for I think he fucked the mouse pad.

Type: Movies
Posted: 10/13/2009
HOT GARTER BELT TATTOO

That is one fucking hot tattoo right there. But as this is crazyshit.com I hope she is not some tranny. That being said, if she isn't it's hot. If she is, well, maybe a little less hot.

Type: Pics
Posted: 08/30/2009
SUNDAY SEX TIME

More Cocky Bitches You can‘t deny that we have not had any tranny videos up in a long time. Hell we might have been long over due. We have a certain quota of fat girls, big fat girls, and just pure weird porn to put up. Then we have a quota of trannies. Today we filled that quota. Enjoy 4 boobs 1 vagina and 1 dick on two bodies. You do the math. See more Trannies Here!

Type: Movies
Posted: 07/12/2009
HEY THERE MR. FANCY PANTS

Type: Pics
Posted: 04/29/2004
MY WORST NIGHTMARE

The need to make tranny bathrooms

Type: Pics
Posted: 01/27/2005
ALL I CAN SAY IS THIS: DUDE IN A ONE PIECE

He at least could have wore a better pair of shoes!

Type: Pics
Posted: 02/27/2003
HERE'S A RIDDLE FOR YOU: HOW CAN YOU DRAG RACE WITH OUT CARS?

Type: Pics
Posted: 06/20/2003
WHAT A JERK OFF

All it does is stay home and titty fuck itself all day long. Nothing wrong with that.

Type: Pics
Posted: 09/05/2010
SNEAK PEAK

Have you ever felt embarrassed when you take a peak at a nice ass in the distance, but later on find out that hey that‘s not a woman?

Type: Pics
Posted: 03/16/2009
WATCH OUT, SHE'S PACKING HEAT

Type: Pics
Posted: 06/11/2004
IT'S TIME TO LICK THE BOY PUSSY

That‘s the problem with having a big dick. People want you to stick it in all sorts of crazy shit. Thank God we have this site, to show you Mr. 18incher, eating some tranny‘s ass!

Type: Movies
Posted: 05/14/2007
WUHHH OHH!!!

This could prove to be a problem, run nigga run. Unless your into chicks wit dicks I wouldn't hang around fo this shit.

Type: Pics
Posted: 12/11/2005
FANCY PANTS

I am smiling right now and that is because a bunch of people out there just clicked on this picture expecting to see one thing when really it was another. Then again some people realize they don‘t even care once the bulge becomes apparent.

Type: Pics
Posted: 07/12/2008
SEXY LITTLE SLUT

All thos nice curves...well except that one.

Type: Pics
Posted: 12/13/2006
PAY ATTENTION

Remember is school when you stopped paying attention and all of a sudden you missed a crucial piece of information.  Well the same thing can happen when you go out to the bar so make sure to check for that adams apple.

Type: Pics
Posted: 05/22/2008
WELCOME TO THE JUNGLE

You have to know how to swing in the jungle or else you might get caught up in the web of a giant spider with a insanely huge penis.  Wait what was I talking about?

Type: Pics
Posted: 07/26/2008
SURPRISE SURPRISE

I don't think anyone saw this one coming. In my opinion He made the right choice. He already made out with her on TV might as well take the money too.

Type: Movies
Posted: 05/21/2006
BOY THIS ASIAN LADY IS FOR YOU!

I have always wanted to go to Asia with some friends and find a ladyboy whore house that is poorly labeled so I can pay for all my friends to get blown by dudes and then tell them they are gay for the rest of their lives.

Type: Pics
Posted: 10/01/2008
THE RING TRANFORMER

Nothing better than a dude with a big pair of tits.  You can still do all the fun guy stuff and then when you get bored you can give his boobs a little squeeze. 

Type: Movies
Posted: 08/06/2008
REALLY REALLY HOT UPSKIRT PICTURE

You can tell it's hot out since she is just "airing" out the goods here. I hope you didn't even remotely think that was a woman at first because you might just like trannies if you did.

Type: Pics
Posted: 09/27/2009
ALWAYS CHECK HER FROM BEHIND

There are a lot of things that can be hidden in the nooks and cranny of a human body so try to make sure there aren't any nine inch penises hiding under those seemingly skimpy g-strings.  That huge bulge is there for a reason.

Type: Pics
Posted: 11/17/2008
MORE THAN MEETS THE EYE

It sounds like transformers but if you were looking for big robots that change from vehicles into big robots then you will be sorely disappointed.  Of course that's why you always give the lady a good cup check before you take her home from the bar.

Type: Pics
Posted: 12/04/2007
AND THE WINNER IS..

This douche has just won the world's smallest penis contest. I really think any chick that saw this in person would just giggle and walk the fuck away. You sir have one of two options, pay to get that shit enlarged or just become a tranny. The decision is up to you.

Type: Pics
Posted: 07/13/2009
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