The Most Comprehensive Guide to Sissy Tasks for Every Level

When I first stumbled upon the world of sissy tasks, I didn’t know what to expect. I was a bundle of curiosity, nervousness, but also excitement.

Sissy tasks are more than just sexually-charged challenges. Sissy tasks help individuals explore their submissive side. Plus, they’re done in a playful, enjoyable way. The goal is to enhance self-discovery and personal growth.

Sounds interesting? Well, sissy tasks are very, very fascinating. So why don’t we jump in together and let me talk about these tasks in detail? I promise you’ll find it fun and liberating.

Sissy Tasks in Sissy Training

A sissy man is someone who enjoys being submissive. Nothing wrong with that at all! And yet the term “sissy” was actually a reclaimed slur.

Being submissive means you take on more feminine traits or behaviors. Why? Cause they give you joy. That’s it. You don’t need to give more justification for it.

Some sissies will share that being in the submissive role helps them discover all parts of their identity. Some say it helps them feel unburdened by their daily responsibilities.

Sissy tasks are activities or challenges that unlock a sissy’s submissive side. They vary a whole lot and will depend on the sissies’ experience level and consent. Being a sissy doesn’t mean you can be forced to do something you’re not comfy with. You can tailor these tasks to suit you.

Benefits of Sissy Tasks

Why do these tasks matter? For me, sissy tasks help me with my

● Self-Discovery – Engaging in sissy tasks allows me to explore parts of my personality I didn’t know existed. It’s surprising to see what I’m comfortable with!

● Confidence – Each completed sissy task increases my self-esteem. I feel accomplished.

● Creativity – Sissy tasks urge me to be open-minded. When I can imagine everything, it becomes easier to express myself in ways that feel good and unusual (in a good way) to me.

● Personal Connections – Sharing my sissy experiences with others lead me to supportive friends. It also matched me with great partners over the years.

● Stress – Since I’m the oldest sibling, I’m used to having all the responsibilities thrown at me. When I channel my sissy persona, I can let my partner take care of me. All without the guilt.

Before You Begin

Engaging in sissy tasks is an exciting adventure. But I would be doing you a disservice if I didn’t share these few important reminders with you.

No Spontaneous Sissy Tasks

It’s intriguing yes. But spontaneous sissy tasks leave room for harm, even if they’re unintentional. In my personal experience, all tasks should be carefully considered. Both by my and my dom’s boundaries. All talks should also happen before any activity. Preparation and open communication are very important — all the time.

There shouldn’t be any guessing game when it comes to what the partners think of and feels about the sissy tasks. This is crucial to create the foundation of trust.

“You can make me do whatever you want.”

Yes, it’s hot to say, but this simply doesn’t work for sissy tasks. For everything else to go smoothly and remain safe, consent and mutual agreement should be prioritized.

Each of the partners should feel free to voice preferences and reservations. Talk about what’s on the table and what’s off-limits to avoid triggers. Whether we like it or not, there are certain activities that can bring up emotional responses. These can be full-on traumas or just unpleasant memories from someone’s past.

That’s why open dialogue is very important. It’s to talk about what specific tasks might be inappropriate. This is also where rules like traffic light signals come into play. You need to have a system for anything the dom isn’t sure of.

Distance Isn’t An Issue

“What if my master or mistress is far away?” I honestly don’t see the issue here. Even when my dom and I are miles apart, we can still bond and continue my sissy training.

Modern technology has given us endless options. There are video calls to messaging apps. You two can do the work in real time. I’ve had successfully done sissy tasks via virtual means. If you have reservations about this, you can stick to sexting with no images or vids.

If you’re OK with it, you can do your sissy tasks and send “proofs.” What profs are acceptable will depend on your trainer. Maybe it’s sending photos or doing tasks while on a vid call. It can also be as simple as describing specific activities during our interactions.

The goal is to keep that sense of accountability and connection. No matter the distance!

Better with A Dom

Sissy training is possible to do on your own. But if you’re not a beginner and really want to get the ball running, find a dom. The goal is to be able to just let go and let another person take the reins anyway, right?

With a dom around, you’ll need to do less research, you can also be more focused on your sissy tasks and what they mean to you. Doms make the process far more enriching. Think of them as your safety net.

Personally, I find that with a dom, I become more accountable. When I know there’s someone else who look forward to my progress, I don’t want to disappoint them. When it’s just me, I sometimes pretend nothing’s wrong with not doing any task or cutting corners.

Beginner Sissy Tasks

When it comes to being a sissy, starting out can feel a bit overwhelming. But don’t worry! I’m here to share some beginner sissy tasks that are perfect for someone with zero — as in nil — experience.

These sissy tasks are usually ones that you can do alone. They’re less intimidating and more accessible.

● Buy a Set of Women’s Lingerie

One of the first tasks I recommend is to buy a set of women’s lingerie. Yes, we’re kicking off strong!

When you go lingerie shopping, you’ll see different styles and colors. Go for those you usually don’t wear! Either because they don’t suit you, or because they may draw too much attention. We’re working on your humiliation kink here a bit. But if you’re not into that, go for the usual colors you like!

The goal is you choose something that you feel attractive in. When you’re excited about what you look like, you’ll want to continue the sissy training!

● Wear the Lingerie Around the House

Once you get your lingerie, the next step is to wear it in an area you feel safe in, like your room. This can feel a little daring — and that’s the whole point! New sissies should be emboldened.

Being at home gives you the freedom to get comfy in your new outfit without the pressure of being in public. You should feel relaxed. Enjoy the sensations of the fabric against your skin!

● Take a Sexy Selfie

Commemorate this historic event in your sissy training with a selfie! It’s something you can look at in the future. A keepsake of where you were before fulfilling your sissy training.

Pretty easy sissy tasks, don’t you think?

Lewd Sissy Missions

● Edge Yourself

“Whoa! We jumped from taking a selfie to edging?” Yep, we did! Edging is pretty simple anyway. Strip it bare and it’s just holding back from cumming. Do it at least twice and notice the difference.

Edging, when you know you can come anytime you decide to, is about playing with pleasure. You shouldn’t go overboard here, OK? This sissy task will make you more sensitive. When you’re sensitive, the sensations become more pleasurable!

● Cum Without Touching Yourself

Another intriguing mission! This may sound challenging, but it’s a great way to control yourself. Use your imagination or watch something that gets you in the mood. You also get to focus on achieving pleasure without always connecting it to physical touches.

● Fuck Yourself on a Dildo and Film It

This is easier than the previous task since you get a lot of help from a sex toy. Want to take things up a notch? Film yourself doing it! For your privacy, you can wear a disguise or not include your face in the frame.

Intermediate Sissy Tasks

Intermediate sissy tasks are for sisses who have “some” XP under their belts. These usually involve interactions between you and your dom. The goal is not just focused on you, but you and your handler’s dynamic.

Public Sissy Adventures

● Call Me “Mistress/Master” In Public

“Call me master.”

I still remember when my dom suddenly whispered this to me as we got out of his car to eat at a rather fancy resto. I thought it was just a random hang-out, but nope. He also talked about this with me before, way, way before, that I almost forgot.

But my immediate response was “Yes, master.” It was a confirmation (for us both) that my sissy training was paying off. I didn’t ask any questions, I was immediately into my sub persona.

This task will give you that rush of “What will people think,” but also “I don’t care what they think!” The shocked looks or amused smiles from strangers can be such a delightful part of the ordeal!

● Answer to Your New Name

Another fun assignment is to respond to the new name given to me by my dom. This task is to fully separate me from my “day” identity. When I’m with him, I’m no longer “Me,” I become “His.”

This reinforces the bond between you and your dom. If your dom uses your new name in public, you’ll feel that adrenaline and shift in mindset.

● Only Eat What I Tell You For the Day

This sissy task gives control to your dom to something crucial for your survival: food. I remember the first time my dom did this, I forgot to tell him that I was allergic to what he made me eat.

It wasn’t his fault, but he was extra careful with me for the next sissy tasks. It just reminded me that I was in good hands.

Note that this task is not a means to be abused or forced to slim down or change diets! Responsible doms only do this to make the sissy lean more on them.

● Mow the Lawn in Daisy Dukes

“…while I watch,” my dom added. There are layers to this task. You can either have a lawn with a privacy fence or not, for instance. Your dom may watch you and be “territorial” when he catches others staring at your plump behind. Or, he might act like he doesn’t care.

What your dom does will depend on what you two talked about before the sissy training started.

● Buying Lingerie and Announcing It’s For You

This sissy task doesn’t require much from you. You just have to be there while your dom shows off how much he loves spoiling you. The catch is if any brave soul will step up and ask “Why?” This was a real concern for me because I was still a semi-out gay guy when my dom did this.

The takeaway then was to shut up and take what my dom wanted to give me. I can’t protest or complain because he was doing me a favor, right? He was very enthusiastic about it too.

“This lingerie will make your ass look so good!”

“Oh, this bra’s color is a nice match to your tan lines!”

There was an element of public humiliation, yes. But he was also very protective when anyone came close and tried to make fun of me. As my dom said, he was the only one who can “bully” me when we were sissy training.

Filthy Sissy Exploits

● Wear My Panties/Boxers to Work

This task keeps that bond between you and your dom. It’s also one of the first tasks where your sissy training may bleed into your professional life.

It’s a naughty secret you must keep while at work! It turns your everyday routine into a not-so-routine. There’s an element of “What if someone accidentally sees?” and “How can I explain this?”

Your body language will automatically be more docile and submissive to avoid attention.

● Buy a Monster Dildo and Lube in Daylight

Doesn’t sound too bad, eh? But what if your dom tells you you can’t put them in obscure containers? Imagine holding a monster dildo and lots of lube in a transparent plastic as you go about your day.

You walk the crossroads, ride the train — what will everyone think? These bold purchases help you develop your shamelessness. It’s something you’ll need when you start to beg your dom for, ehem, unholy things.

● Wear This Chastity Belt/Cock Cage To Work

Remember edging yourself? In this case, you want to show your dom you can be a good sissy and never say no to making him control your cock. Even if you’re far apart!

It’s another training to put you under the power of another. In this case, there are other people involved, though they may not know it. You’ll develop your composure and control of yourself too.

Advanced Sissy Tasks

Advanced sissy tasks are for the sissy pros looking for something to tickle their fancy.

I want to make it clear that not every sissy might feel comfortable with the sissy tasks I’m about to present to you. Yes, even if they’re experienced sissies. That is perfectly OK, since sissy training can be different.

These are not a strict checklist. These are just some sissy tasks I’ve done with my dom before. Maybe you or your dom can get an idea or two from these tasks for your sissy training.

Public or Private?

These tasks can happen in either public or private settings, depending on what works best for you and your dom.

In public, there’s a heightened thrill from the fear of being discovered and humiliated. For instance, wearing a plug while out and about is more intense than just being a sissy maid observed only by your dom.

The good thing about tasks done in private is they can always be stopped. In case the sissy feels overwhelmed. But when you’re out in public, the risk of someone realizing what you’re doing can add to the stimulation or kill it completely.

Some may not care at all. But some sissies may worry about how the discovery might affect their career or reputation. Additionally, some tasks may involve other willing participants. This includes the roleplay of a cuckold husband.

Crude Sissy Quests

● Walk in the House Naked, Leave all the Windows Open

This willingness to be vulnerable is for the sissy to celebrate himself and feel liberated. When you walk around the house in your birthday suit, not knowing who could be watching, you can get a confidence boost. Especially when you know you look good!

● Wear a Microskirt with Your Panties Showing

Donning a micro skirt that reveals your panties is a risqué assignment. But at this stage, that’s a given.

This task is for you to express your femininity boldly and confidently. Walking around like this encourages you to strut your stuff and own the attention. It can be a simple outing or a flirty escapade.

● Work in a Nightclub with a “Grope Me” Sign

This assignment takes things to a whole new level of daring. Working in a nightclub while holding a “Grope Me” sign is for the brave-hearted sissies who want to push their limits. Doing this task will make you realize that you can “serve” other people too. It’s empowering to be wanted and admired through others’ reactions.

I know this isn’t easy to do, since there are real slimeballs in sketchy clubs. Only do this sissy task if you’re familiar with the nightclub and the regulars in the nightclub.

You can disclose to them your task or not. Nonetheless, always put your safety at the top of your priority. Your dom should also be on the lookout when you’re doing the task.

Obscene Sissy Exploration

● Watch Me Cheat on You and Film My Cheating

Since we’re talking boundaries and cuckolding, this sissy task is one of those in the extreme categories. It can be a random task your dom springs to you. The surprise element can make the sissy feel embarrassed but also turned on.

It’s two taboos in one. But the desire to be “disgraced by your lover” isn’t a new trope. In fact, there are many hentai and 3D games that explore similar scenarios. But what’s the charisma of such a trope?

For the most part, it dives into the dom’s “strong control” over the sissy. The dom’s control is very potent that the sissy doesn’t dare oppose the dom’s decisions. It also plays into that “unbreakable trust” between the sissy and the dom.

This sissy task can also be scheduled to prepare the sissy. Since this includes another participant, be sure to remind each other of any limits.

● Drive Around Town While I Do the Nasty with Someone in the Backseat

This sissy task is very similar to the previous one. The only difference is that the sissy is meant to be distracted by the driving. But his mind is obviously on what’s happening in the backseat of the car.

Trues, this assignment is a wild ride — literally! There are also other elements to consider. The sissy, aside from being his dom’s “driver,” is also seen by others outside the car. The humiliation is doubled.

● Wear A Plug While We’re On A Date

This one is pretty tame compared to the first two. But it’s perfect for a dom and sissy pair with an exhibitionist kink.

This task keeps the sissy in place and in his dom’s control with just a few presses of buttons. Depending on your dom’s personality, he can use this task as a punishment to keep his sissy in check. It can also be a way to tease and as a foreplay to a long night of sex.

● Let My Friend “Borrow” You for A Day

By this time, the dom completely “owns” the sissy and can loan him out to whoever he pleases. Alternatively, this task can also be “Let me auction you to the highest bidder.”

This task leaves the sissy to do whatever the “friend” or “bidder” asks him to do. No matter what it is, or else his dom will punish him. Of course, these activities will still be under the agreements of all parties involved.