One reader gave me a great idea and this new section is the result and I'm so going to enjoy this. Every once in a while, I'm going to give you sissies out there a job to do. It might be something fun and positive or it might also be something embarrassing and humiliating - probably more of the latter ;). This particular reader suggested sending in photos of himself dressed as a sissy and me using that as blackmail to force him to do jobs. Well, I don't want to go that far for now and give you a chance to be compliant by yourselves. Don't worry. At first, the sissy tasks will be quite harmless but as you progress and become more obedient, we'll get more creative.

When you've completed your task, report back in the comments below describing the experience and how you felt about it. I'm seriously looking forward to reading these. To be clear: this section is mostly for my amusement, probably at your expense :D. You can only comment if you've completed your task. No other comments are allowed in this section.

Since you have no further questions, here's your most recent sissy task:

Task nr. 6 – PE class

It’s exercise time!

First you must procure yourself the right clothing. You’ll need something that allows for free and unrestricted movement but does not flap around loosely. So, if you don’t already have one, you should get yourself a unitard. Don’t try to chicken out by getting a men’s unitard. It has to be a women’s unitard. Below you’ll find some examples of what I mean. You may choose black or navy blue but I’d really prefer a light pastel color and they can be with or without sleeves.


Now start a routine early morning run – properly dressed of course. It doesn’t have to be in the morning but that is probably the best time for those of you who are shy. You’ll need some decent running shoes too but here you MUST get the shoes that fit you best – even if they’re men’s shoes. In the interest of your health and safety, you should not try to put looks over practicality when it comes to running shoes.


Keep this up at least twice per week. Start easy and don’t push yourself hard. In fact, don’t push yourself at all but ease into the routine and you might very well come to enjoy it.


Thank Krista Stockings for giving me the idea for this task (Krista’s version was slightly different but this is just the first step – more will follow…)

Task Nr. 5 - Halloween Special

Yeah, I know, this was kind of obvious. Still, as ever, Halloween is a great opportunity for some crossdressing action even for those of you deeply tucked away in the closet.
So your task is to go to a Halloween party dressed in one of the following outfits:

  1. Fairytale Princess
  2. French maid
  3. Ballerina
  4. Schoolgirl

It has to be one of those and you may not protest. With such an ‘abundance’ of choices (hehe) surely anyone will find something they feel comfortable in. Now off you go and make the necessary arrangements. If you feel like you might chicken out, then go right now and tell everyone who might come that you’re going to dress up as one of those four. Perhaps post it on your facebook page or twitter account. Then you’ll have to go through with it. :)

Task Nr. 4 - At the Salon

Time to get your hair done sissies!

I want you to find a nice hair and beauty salon where you will ask them to make your hair look more feminine.

If you have long hair *pant* then you have plenty of fun options. You should have your hair curled or styled into an up do. We’ll skip the perm for now ;). If you already have curly hair, then get it straightened. If your hair is short, then ask your stylist what your options are for making it look feminine. Perhaps a pixie cut will suit you nicely

Obviously you need to have a full head of hair for this to work so if you’re not endowed with naturally thick hair, then your task is to find yourself a women’s hat and scarf department with the most feminine hats. Perhaps something like this.
You probably won’t be able to try them on but you can still take a close look and perhaps ask the sales person if they think something would suit you.

Task Nr. 3

Find a dress shop or bridal store with some beautiful gowns that you like. Then phone them and introduce yourself politely. Tell them you’re a man who likes to wear dresses and ask if they sell dresses and accessories to men.

If you want to buy something then say so and ask if you can come around some time to choose something nice. But don’t go unless you really are considering buying something (can be something small too).

If you pick a small shop you’re more likely to get special treatment but if you pick a bigger store then they’re more likely to have experience with male customers.

Remember to tell me all about the experience.

Task Nr 2

Talk to a complete stranger, male or female, about crossdressing and tell them you sometimes wear women's clothes and it's fun

Make sure nobody you know is around. But don’t approach people on the streets or harass somebody who doesn’t want to be talked to. Best is to go to a place where people are likely to want to start conversations with you such as a bar or at a party. I suggest you open the conversation about something totally different (sports if you want) and then subtly push it in a direction so you can say that you like to cross dress. This may require several attempts before you get a good opportunity.

Be relaxed and natural about it, as if you’re telling them you’re telling them you like going to the cinema once in a while. Just mention it in passing if you want and only if they make a big deal of it, then ask them why they’re making such a fuss.


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