Shoplifting male cross-dresser takes off wig

This article is exactly what the title would suggest: a comparative examination and guide to shoplifting (as a man) while wearing normal, male clothing vs. a frilly pink lace bra and absolutely fabulous crushed velvet leggings. For legal reasons, I cannot specify if I actually performed any of the actions described in this article. I will leave that, along with my well-chiseled pectoral muscles, entirely up to your hopefully quite vivid imagination.

Let us begin.

Small Town Shoplifting

Clearly you’re going to want to avoid doing anything even vaguely cross-dressy in any place where "hoedown" and "let’s go to the" are mentioned in the same sentence without immediately being followed by riotous laughter.

What you steal is up to you and your own lube-centric tastes. But make your targets work with your outfit of choice. In a small town they’re automatically going to be looking for a reason to call you out on your booty shorts (my experience in this matter can only be described as "extensive"), and if they try and mess with you while you have in your possession, stolen merchandise, then they will most certainly do everything they can to get you for something.

Probably.

The other likely event is that they will want nothing, and I mean nothing to do with you. Like, to the point where even if you actually tried to buy anything, they might just let you take it, for fear of actually associating with someone in a leopard-print leotard ("cross-dresser" and "80’s rock star" are the same thing, right?). So I’ll let you make the call on this one based on your own rampant homophobia assessment of your town.

And as far as wearing street clothes while shoplifting goes, it’s a well-known fact that if a town has less than a hundred thousand people, is located in the South, and absolutely everyone is somehow both a farmer and an auto mechanic dressed in either a greasy, full body jump suit and/or overalls and a straw hat, dress like them and you should be fine.

Big City Shoplifting

Cross-dresser arrested by police
SO BUSTED!! Like, serious fake man boobs.
While big cities may have their advantages, they aren’t without their drawbacks, either.

Street clothes go more or less like you’d expect, but if you get caught shoplifting, instead of the shopkeeper pulling out a comically outdated single shot shotgun, he will pull out a large caliber pistol, and he will be very well versed on how to use it.

If you plan on cross-dressing, however, any possible head-turning advantages will be negated, because in most large cities, people are used to seeing cross-dressers and trannies, and people may in fact ask you for advice on how you got your nails to do that sparkly zebra stripe thing. (I am assuming you are a very talented cross-dresser. Don’t lie, Paul, you know you are. I don’t know anyone by that name. But at least one guy reading this starting sweating for a second there.)

So you won’t get called out, and that’s good, but Raul, the 300-pound transsexual Samoan who runs the place you’re stealing from, will gladly hop the counter and put you in your place with an abnormally large baseball bat. Like, you’re pretty sure they don’t even make baseball bats that big.

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So now it’s more about function over form to make sure you don’t get caught. This next advice can really be taken no matter the size of the town, or where exactly you’re performing your illicit activities.

When uncreative guys want to dress up like ladies, they usually go for something over-exaggerated, like a miniskirt or a dress. Those won’t cut it here. Turns out women’s fashion is quite an expansive world. There are whole stores full of it, in fact. So try and find something that not only complements your personal style, but maybe something billowy to hide any unseemly bulges where you might stash your contraband. Think pockets.

Lots of pockets.

Now, what you steal is up to you and your own lube-centric tastes, but as most shoplifting guides will suggest, keep it small, and easy to disguise. Make your targets work with your outfit of choice. Plaid can be rad, but only in certain circumstances. All of the circumstances. Please note how I am writing a shoplifting guide and not a fashion magazine guide. I should really leave the specific fashion choices up to you, your girlfriend, or your mom.

Getting Away with Shoplifting

You’re an awful thief. You may have to run away. You will have to run away.

Now, here’s where there is only one clear victor: street clothes. A hundred times over. Because if you get caught, and have to bail, there can be two very different sorts of announcements made over the police radio.

There’s the normal one:

"We have a shoplifter fleeing the local Gap." (You have just like, completely regrettable fashion choice in this example.) "He is a 6-foot tall Caucasian male, dressed in a plain black hoodie, dark blue jeans, and brown work boots."

And there’s the other announcement:

"We have a shoplifter fleeing the local Gap and he is a…a…now, now bear with me here, Tom, please don’t hang up, ’cause, I swear I ain’t making this up, but he is a 6-foot tall, Caucasian male dressed…dressed…now here’s where it gets a little weird. He’s dressed in a skin tight green t-shirt with the phrase ‘Girls make better ninjas’ printed on the front; a blue and green plaid mini-skirt that’s short enough to where he has to be violating some sort of decency laws; and purple, crushed velvet leggings that end in…in um, Heelys. Yes, fucking Heelys. I didn’t even know they made them in adult sizes but there you go. His hair is literally the rainbow. Every damned color. He has what I’m pretty sure are ostrich feathers jutting out of his hair at several points. …Hey, Tom? You know how I said I was retiring soon? Fuck it. I quit. Have fun."

Throw in more accusations of rampant homophobia. People will often buckle under the threat of discrimination charges. I actually own the outfit I just described. And I look fabu-fucking-licious.

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By this point, every goddamn cop in town is listening in on this intently, because they’re pretty keen on seeing this bullshit, so, yeah, good luck hiding from that. And don’t try and strip naked because "then they can’t identify me by my outfit"; trust me, it doesn’t work, and people just point and laugh at you because they don’t realize how cold it is outside and that it’s a perfectly normal size even when it’s not freezing cold, and it’s like, so cold, and that you could totally satisfy a woman with it and SHUT UP YOU’RE A STUPID FACE AND I HATE YOU!

Ahem.

I may have lost my train of thought there for a moment. I apologize. I am normally much more calm and collected then that.

So here’s another situation: You got caught, but you’re not sure if you can get away at all. You still have options.

One of the better options in this situation is available in any clothing situation, but is much easier to pull off based on how much lace your leggings have on them. I’m talking about the discrimination card.

Does it make you a bad person? Pfft, come on. Let’s face it. This isn’t the singular thing that you do that’s going to land you on the "bad person" list. You know exactly what I’m talking about.

Back on topic. Here’s a sexy, sample conversation:

"Sir, could you please stop shoplifting."

"Oh, are you accusing me of shoplifting because you have obscene, overbearing, homophobic tendencies?"

"No. I’m accusing you of shoplifting because you have half of a flat screen television sticking out of your pants."

"That is my TV."

"That is not your TV."

"This is my TV. I like to bring it places so I can watch Castle whenever I feel like gazing upon Nathan Fillion’s sculpted grin."

"I watched you take it from the shelf and put it in your pants."

"…Nathan Fillion waits for no man."

Just like that. Only throw in more accusations of rampant homophobia. People will often buckle under the threat of discrimination charges.

Again, your morals went out the window the moment you put on that Sultry Seductress Red lipstick and marched over to Walmart with the intention of sticking no less than two laptops up your dress.

So go ahead. Make them feel even more uncomfortable.

I realize that those where just a few haphazard pointers thrown together with reckless abandon, but they should be enough to get you started in your career as a criminal cross-dresser. If you want to know more detailed information, then you’re probably a dangerous sociopath, but I’m cool with that. My book on the subject should be out next summer, assuming the publisher who spoke to me in my dreams last night was real.

Good luck out there.

LEGAL DISCLAIMER: "Superhydrophobicity" is a word. That fact has very little to do with my article, or much of anything at all, but I’m really digging it as like, a word. You know, man?

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