Naughty Sissy Tasks: 8 Sissy Dares You Need To Try

Looking for weekly sissy tasks to become an even better sissy boy? Well, you have come to the right place!

Sometimes it's hard to come up with sissy ideas by yourself. So, this blog post will share some super fun "sissy dares" for the aspiring slut to try.

Your sissy mission will be to try and complete as many of these ideas as you can!

This blog post will include:

  • Sissy assignment tasks
  • Sissy public dare ideas
  • Humiliating sissy tasks
  • ...and more!

If you are able to complete all these tasks/dares, you will be ready to graduate from sissy school!

Think you are ready to begin? :)

Dress up and go to nail salon to get mani and pedi

1. Get a full wax

This first sissy task is a classic.

Part of being a good sissy is taking care of your body. After all, looks are very important. That's why you need to get maintenance work done like all women!

So your first humiliating sissy task will be to get a wax...a FULL wax!

That's right...this will include your legs, arms, armpit, chest, etc.

No more hair on your body! You need to be as smooth as a hairless cat :)

Getting your body waxed is a great sissy task to cross off your bucket-list.

If you can't afford to get a wax (as they can be pretty expensive), the next best thing is to shave yourself at home.

While it won't be as humiliating as going to a salon and having someone do it for you in public, it's also a good option.

2. Go to the bar and hunt for numbers

Your next sissy task is more like a dare. And it's simple: go a local bar dressed up in your best sissy gear and try to get some numbers.

Put on anything that to make you sexy: wig, heels, dress, makeup, perfume, etc.

Dress to impress!

Your sissy task for this evening is to go to the bar and flirt with some guys. See how many men buy drinks for you.

And then see if you can get any numbers.

Bonus sissy points if you make out with someone.

And extra bonus sissy slut points if you end up sucking cock that night.

Now, if this is your first time doing something like this you may be nervous. But don't worry! It's a rite of passage for any sissy. This is the perfect sissy public dare...don't you think? :)

3. Go on a Grindr date

If the last one (a very public sissy dare) isn't something you are comfortable doing yet, then this next task is for you!

There's nothing like going on your first sissy date, but sometimes you may be too shy to approach guys in public.

So that's why I want you to go on Grindr and start swiping! You can also use other dating apps like Tinder of course.

Anyways, get your profile all set up. Dress up like a good sissy and take some good pictures for your profile.

Once you start getting some matches sext with those guys! Share some sexy pictures with them and then ask them to go out on a date.

See where it goes! Who may be sucking cock at the end of the night :)

4. Begin wearing your sissy clothes to work

Your next sissy task is to begin wearing sissy clothes to work underneath your normal man clothes. Obviously this works best if you have an office job.

Start off easy by wearing a pair of panties instead of your usual boxers or briefs.

After that you can do some more risky ideas like bras or garter belts. And if you're feeling extra risky, you can even paint your nails :)

Before long you'll be brave enough to wear full sissy outfits under there!

What makes this really fun is you are a "hidden sissy". No one at your desk will suspect anything, but you know deep down what a sissy whore you are!

Naughty Sissy Tasks  8 Sissy Dares You Need To Try

5. Butt plug sissy dare!

Part of being a good sissy is learning how to take it up the ass!

After all your ass is no longer an "ass", it's a manpussy!

So your sissy task for the day is to wear a butt plug for 24 hours. Yes, even while you're at work, on the bus, or just simply at home doing nothing.

Wearing a butt plug like that will train your ass to stretch for your mistress or other men.

And like I always say, sissies should be caged and plugged no matter what so they are frustrated to the max. Some would say this is more of a punishment task :)

6. The ultimate sissy task...

Being locked in chastity as a sissy is a must. But not all chastity cages are equal.

Some are smaller than others. Some are more comfortable than others.

And some cages are more "sissy" than others.

That's why the Cuck Denier is undoubtedly the number 1 cage for sissies.


Because it's a pussy shaped chastity cage designed to be as frustrating and humiliating as possible.

Yes, you read that right! It's a pussy shaped cage to remind you of what you're missing out on.

And not only that but the Cuck Denier is PINK - the perfect sissy cage color!

And who knows, maybe after a few months in this cage your little "dick" will shrink down to the size of a nice sissy clit!

The Cuck Denier

7. Complete 3 makeup tutorials on YouTube

Being a sissy is more than being caged and wearing girl clothes.

It's also about looking pretty! And the best way to accomplish that is learning how to put on makeup.

This includes putting on lipstick, eyeliner, doing your eyebrows, putting foundation on, etc.

And it includes doing beauty procedures as well such as face masks, etc.

So, your sissy task is to learn as much about makeup as you can.

I want you to watch 3 YouTube makeup tutorials. And obviously just watching isn't enough. Go out there and implement what you learned like a good girl :)

Putting on makeup like this is a great sissy training task!

8. Try on high heels at the mall

If you are a more experienced sissy, this sissy dare is perfect for you.

And it involves being a public sissy

What do I mean by this?

Well, I want you to go to the mall to buy some shoes.

But that doesn't sound super sissy at all!

But you haven't heard the rest of the task...

You will be going to the mall to try on some high heels to buy!

Obviously you will need to dress up like a good sissy too. Go to your local mall and ask the sales associate for some help in picking out a new pair of heels.

Try a few of them on, take some pictures, and see which one best suits your wardrobe.

Buy them and you'll complete this super awesome sissy slut task!

Naughty Sissy Tasks & Dares - Final Thoughts

Part of being a sissy is trying out new dares and fulfilling your deepest fantasies.

Hopefully this sissy list gave you some super fun ideas to try.

And remember, being a sissy is about the journey, not necessarily about the destination - just enjoy the experience!

P.S. let me know which sissy task was your favorite and which one you want to try the most in the comments :)


  • I love going to a nail salon fully dressed with high heels and make up and getting a mani pedi.

  • I have done most of these. One of my favorite firsts was when my wife and her date took me to dinner and a show fully dressed. Cage included.
    They took lots of photos and did some light making out during the show.
    It was a bit of a rush when he told the waitress that I was her husband. She just looked at me and smiled before walking away.
    Then the staff was in the entry to the kitchen pointing me out.
    I drove them home after so being the driver I did it all completely sober.
    They had fun when they got home. I got to listen and serve coffee in the morning.

    Sissy Jess
  • I love all the tasks assignment that you give me and by the way can I please get more humiliating and degrading TASKS MISTRESS.

  • These are all great tasks, I have done these all but need to work on the dating side of it. I dress daily and love it, makes me feel wonderful

    Jennifer Green CD
  • Another I am eager to try is go to a lingerie shop and ask the sales girl for assistance in trying on lingerie. Select panties, what I want to do, bras or anything she might suggest. Have your key holder there to take pictures and encourage the sales girl to do the same.


Leave a comment

Please note, comments must be approved before they are published