The last few years, as part of my general plan to be better at certain things, I have a habit of setting a year-long goals for myself, with some monthly sub-goals. One of my goals was to write a blog post every month. So far this year, I’ve written nine – this will be number ten! 83% completion isn’t the worst, especially given everything that’s happened this year. I also have a goal to read a book every month (currently at 50%), to run (33%), and some others. My dressing goal is at 9/12, so 75%. Not the worst, I suppose. The point isn’t necessarily to get 100%, but to set some achievable goals that might make you push yourself a bit.

Being goal-oriented helps me focus on the things that I feel like I need to work on, or that I find important, even if they’re little things. For example, I have a goal to cut my hair every month, or to hang out with people. This seems kind of stupid, but I tend to start feeling a bit depressed once my hair gets a little long (I’m talking, maybe a centimetre), and at the beginning of the year I felt kind of isolated – although maybe that was more to do with recent parenthood! Having the goals there is a useful kick in the pants to remind me to just spend the five minutes cutting my hair, which keeps me off the dark path and on the right mental plane, or planning a thing with friends, after which I always feel a little less lonely. Similarly with my dressing goal – Being a little motivated to find time to dress regularly seems to be good for my mental health. And having a fitness goal has been good for my physical health also.

The goals are essentially pointless if you’re not checking in with them all the time, so I do a couple of things to keep me honest. One is that I have a widget on my phone that shows me the goals I haven’t yet completed that month (and any goals I hadn’t completed from previous months, because I roll them over!), and secondly, I keep a tab pinned in my browser so that the goals are always present and visible.





When I first started dressing up I think it would’ve helped me to have a list of goals or achievements that I could’ve looked at/checked against to get an idea of how I was doing, but also to figure out what it is that I really wanted to achieve. Some people might not ever want to come out to family, or even dress outside the confines of their bedroom. Others might want to go as far as possible and dress full-time. I thought it might be useful to put together as exhaustive a list of crossdressing goals that I could come up with to see if people might find it useful. There are definitely things on here that I haven’t done (yet!).

What are the things people want to accomplish? What did I want to accomplish? What do people talk about doing that I haven’t done yet? Are there things that I could push myself to do that I haven’t done, or that I haven’t been comfortable with? These are some of the questions I asked myself while trying to come up with this list. I’d love to hear your crossdressing ideas too!

Starting out

Buy makeup online

Buy clothes online

Buy shoes online

Practice makeup

Practice walking around in heels

Spend the day fully dressed at home.

Get fully dressed and taking selfies

Choose a female name

Post selfies online with your face covered

Post selfies online with your face exposed

Walk around the block at night in a wig

Walk around the block at night in heels

Take the trash out at night, while dressed

Take the trash out during the day, while dressed

Order takeout and answering the door while dressed.

Talk to other crossdressers online

Exploring the world

Buy makeup in a store, while in guy mode

Buy makeup in person in girl mode

Buy women’s clothes in guy mode

Buy women’s clothes in girl mode

Try on a dress at a store in guy mode

Try on a dress at a store in girl mode

Go to a bar while dressed, with friends

Go to a bar while dressed, alone.

Go to a restaurant while dressed

Go to the movies at night, while dressed

Go to the movies, during the day, while dressed.

Get your eyebrows done in guy mode

Get your eyebrows done in girl mode (assuming it won’t ruin your makeup)

Pushing yourself

Paint your toenails

Keep your toenails painted for a few days

Paint your fingernails

Keep your fingernails painted for a few days

Get your nails done in guy mode, no polish

Get your nails done in guy mode, with polish

Get your nails done in girl mode, with polish

Get your ears pierced

Wear dangly earrings

Travel

Drive at night, while dressed

Drive during the day, while dressed

Drive at night and put gas in the car, while dressed

Drive during the day and go through a drive-through, while dressed

Drive at night and go through a drive-through, while dressed

Take public transport dressed

Fly with your girl clothes in your suitcase

Fly dressed

Work

Go to a fancy-dress/costume/halloween party at work, dressed

Go to a regular party at work, dressed

Go to work on a regular day, dressed

Give a presentation while dressed

Telling people

Tell a close female friend that you’re a crossdresser

Tell a close male friend that you’re a crossdresser

Tell your partner that you’re a crossdresser

Tell your parents that you’re a crossdresser

Tell your family that you’re a crossdresser

My Goals

The above probably isn’t an exhaustive list, nor is it a checklist of things you need to do. In some way, it’s more of a choose-your-own-adventure – figure out what it is that you do want to achieve, and figure out how to get there! :) I haven’t done a good few things on this list – for example, my dressing goals for the year include:

Dressing at least once a month – standard goal

Driving dressed – doable, I’ve just never done it!

Going to the movies dressed – I’ve done this before, but not on my own

Try on a dress at a store, in girl mode – Done this in guy-mode :D

Flying Dressed – ok, this one terrifies me, but it seems like it’s possible, and there’s a good few blog posts on it out there. Hopefully one more, someday :D

Not to mention working on some particular blog post ideas, and seeing if I can get a couple of photoshoots done. Maybe one outside?! Outside shoots have always seemed scary, but who knows! Maybe I can push myself a bit :)

Hopefully you’ll find this list of crossdressing goals/crossdressing challenges a good starting point to figure out how to get to where you want :)

Where do you want to get to in 2018? What are your crossdressing goals? I’d love to hear what you’re challenging yourself to!

xx