16 Jokes For Crossdresser

Puns

Updated on: Mar 25 2025

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I tried to make a joke about crossdressers, but it was a drag! So, I'll stick to the skirts and instead!
Why did the crossdresser go to space? To show that fashion has no boundaries – it's a universal statement!
Why did the crossdresser become a gardener? Because they wanted to let their wardrobe blossom!
Why did the crossdresser open a bakery? Because they wanted to make a statement: 'Buns in the oven, heels on the floor!
What do you call a crossdresser who can't make up their mind? Bi-dress-tional!
Why did the crossdresser apply for a job at the tailor shop? They wanted to sew the seeds of style!

Crossdressing and Car Troubles

I got pulled over by the police while dressed as a woman. The officer asked for my license, took one look, and said, Well, this is a first. I didn't know if I should explain my gender-bending escapade or just thank him for acknowledging my bold fashion choices.

Closet Chronicles

Alright, so I recently discovered that my closet has turned into the Narnia of fashion. I mean, I opened it, and suddenly, boom! I'm in a whole new world of sequins and stilettos. I didn't know whether to be concerned or just embrace my inner fashion lion.

Dressing Up and Losing Friends

I invited my buddies over for poker night, but I forgot to mention my newfound hobby. The looks on their faces when they saw me dealing cards in a feather boa – priceless. Let's just say, I'm still waiting for those apology texts.

Fashion Forward, or Just Lost?

I tried my hand at crossdressing the other day. Let's just say, my attempt at high heels made me appreciate escalators in a whole new way. I felt like I was learning to walk again, but this time, with added height and a serious risk of ankle sprains.

Dress for Success, but Not My Size

I decided to raid my girlfriend's closet for crossdressing material. Let's just say, my broad shoulders weren't exactly made for delicate sundresses. I emerged from that closet looking like a sausage squeezed into a chiffon casing.

Fashionista or Confused Artist?

I tried to follow a makeup tutorial for crossdressers. The result? I ended up looking like Picasso had a wild night out with a box of crayons. Smokey eyes turned into a smudged disaster, and my contouring made me resemble a contourourist – lost and confused.

Wardrobe Malfunction Meltdown

So, I decided to surprise my significant other by dressing up as someone else. Little did I know, my crossdressing debut turned into a fashion emergency. I got stuck in a zipper, and there I was, frantically yelling for help while trying not to flash the neighbors. Romantic, right?

Crossdressing and Confusing the Cat

My cat witnessed my transformation into a crossdresser. Now, whenever I try to have a serious conversation, he just stares at me with judgmental eyes, like he's thinking, You, sir, are not the person I signed up to live with.

Online Shopping Catastrophes

I decided to order some fabulous outfits online for my crossdressing adventures. The delivery guy must've thought he stumbled upon the weirdest game of Secret Santa ever. I got a box full of glitter, wigs, and a note saying, Good luck, buddy.

Gender-Bender Gym Fiasco

I thought, Why not break stereotypes at the gym? So, I rocked up in a sports bra and leggings, ready to lift weights and break hearts. Turns out, breaking a sweat wasn't the only thing I broke – my dignity shattered when I couldn't get out of the sports bra post-workout.

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