How To Dress Your Sissy Maid

Like most key holders for sissy slaves, how I’ve dressed my sissy maid has evolved over time. It started with a simple maid costume that I purchased online and has grown into a wardrobe of various outfits that I mix and match for her every time she cleans. How you dress your sissy maid will likely evolve over time as well, but let this be your quick guide to easy costumes and accessories to help you get started.

Click on the images below to view the products on Amazon.

The Basics

Dress / Costume

The most important piece of the sissy maid outfit is the dress. As I mentioned earlier, I started my sissy with a maid costume meant for Halloween. This is a great way to start because it comes with a lot of accessories like apron and headband to save costs and require fewer purchases. Of course these costumes and accessories will likely be cheap quality and if you plan on having your maid do a lot of work, you may need to invest in better quality clothes in the future. My maid now wears various combinations of skirts, blouses and aprons.

Thigh Highs

Guys tend to love wearing thigh highs and they really help complete the outfit, especially if your man doesn’t shave his legs yet. These ones are by far my favorite because they come in white and black (the perfect maid colors) and have bows at the top. This particular listing also sells them in standard size and plus size. Plus size is great if you man is taller or bigger.


You want your sissy maid to feel like a sexy woman, right? They have to have some lingerie to tie everything together. Something to cup their man boobs a little which also has garters to hold up their thigh highs. Just like the thigh highs, this lingerie comes in black and white along with other colors for whatever your preference is for your maid.


The lingerie will likely come with a tiny little g-string thong, but that’s going to be hard for your maid to fit their caged cock in. Luckily, there are lots of options for pouched sissy thongs that will hold their cages in while giving them that panty feeling. These are my favorite sissy panties because they have ruffles all the way around and have the thong back which my sissy slave just loves.

The Advanced

Breast Forms

I like to go the extra mile and make my sissy understand how it feels to have extra large breasts so my sissy slave is required to wear these size E breast forms. They’ll take him some getting used to, but he will start to love them. They will be fun for you to rub and play with to tease him while he works, too.


This becomes a must if your sissy maid gets breast forms. He is going to need something to hold those breasts up and the little lingerie from before isn’t going to cut it. Not to mention that he needs to start having some more feminine curves, right? A nice corset will accomplish both of these.

Butt Plug

I was torn between putting this under Basics or Advanced because I believe that all sissy slaves should be caged and plugged at all times. This one is a favorite of ours, your sissy slave may prefer another type.


Pink Gloves

You’re going to want your sissy maid doing some deep cleaning on her hands and knees, but you won’t want her hands getting eaten up by chemicals. Let her wear these cute pink cleaning gloves while she works for that extra dash of femininity and to protect her hands.

High Quality Apron

This is a great apron. Very high quality but feminine enough with the frilly edges to make it sexy. Also has pockets to help your sissy carry needed supplies.

This may seem like a lot but don’t fret. Your sissy slave will be paying for everything and more (like cleaning supplies). You both know that he wants to be your sissy and dress up like this and that you allowing him to be your sissy maid is a treat, reward and an honor. So of course he will be buying everything himself. If you plan on surprising him with his first outfit, give him a bill after he finishes his first day of cleaning.

Do you have other favorite attire or accessories for your sissy maid that we’re missing? Share with us your must haves!

One thought on “How To Dress Your Sissy Maid

  1. Ach wie schön diese Seite doch ist *seufz* auch ich träume schon so lange davon eine ehrliche und streng/dominante Dame kennen zu lernen um IHR gehorsam als zofe zu dienen und alle ihre Wünsche zu erfüllen. Leider ist das gar nicht einfach…
    zofe frida, ich bin frei und möchte es nicht mehr sein 🙂

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