Crossdressing Goals 6

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.

I use for all this. It’s pretty cool. Also you’ll see some of those numbers are a little out of date, because I started working on this blog post a little while ago, and have made progress since :D

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


  • 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


  • 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!


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6 thoughts on “Crossdressing Goals

  • Rebecca Williams

    Well 2017 included, in my many outings dressed: plenty of shopping and trips on public transport; lots of National Trust houses; several church services; Ladies’ Day at Brighton races; two football matches with big crowds (soccer to you folk across the pond!); a day out in Amsterdam. Oh and putting ‘gas’ in the car while out driving in the daytime :)

    For 2018, or as soon as viable? A London show, a weekend retreat on my own and a girls’ weekend somewhere – preferably abroad. And I’d REALLY like a valid excuse to go out in this seriously posh frock I’ve got. Have to work on that lot!

    Rebecca x

  • Amy Stephens

    Yeah I did three days in NYC dressed, driving, Amtrak, subway, two days in a class, Airbnb, and dinner with a family friend all dressed. You know what? It was fantastic.

  • Laura

    Well after cross dressing for many many years in the proverbial closet I’ve began to realise I want to live as a woman, I just need to find the courage to take the first step as I have a wife and family who I know in my heart I will lose from my life there would be no tolerance I know.Your blog gives me lots of goals and is fabulous my mind is a rush now!

  • Domannique Brown

    Since 1994 I have an excel spreadsheet made up of 40 different goals for the year. They vary from the amount of photos i am to take of myself, to going out to eat, to telling close friends and being dressed for them, amount of hours to dress per year, how many shoes to buy for the year, and it goes on and on. Like I said it is 40. I apply a numerical value to it so I can see a percentage of my completed goals and I also color coordinate them at the end of the year. I also change them depending on if it is an obstacle that I needed to over come. I also carry over goals that I didn’t complete. Because I love to succeed my list forces me at times to do the things that I would otherwise not do.