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The Crossdresser’s Guide to Avoiding the Curse of Unintended Consequences

Our newest Contributor, ladies this is Maddie Smith!

By Maddie Smith

I guess if you have been around for a bit you’ve got a list of unintended consequence stories to tell.

I know I have plenty!

However, for younger readers, you need only look to history for lots of such stories, and I mean there are a lot! There are probably lots of gender-related examples as well. I’ll let you look those up!

An example: did the guy who decided we no longer needed the law requiring someone to walk in front of an automobile holding a light have ANY idea that the things would go ever faster and kill around 1.35 million people every year? Extreme but definitely an unintended consequence. Can’t really blame him though …

Or how about the Black Plague; it spread rapidly, killing up to 60% of Europe’s population in less than three years. Prior to its arrival Christians began killing cats because they believed they were the product of the devil. Of course, their attempts to prevent bad luck from the cats turned into good luck for the flea-carrying rats as they bred and spread almost without restriction. That’s a hell of a consequence.

I blew up a hot water cylinder one day. Did you know they take out the whole wall when that happens? And scare the hell out of the (now wet) builders … Definitely an unintended consequence of the builders changing how they wanted the systems tested. Unintended but probably foreseeable. Well, I say I blew it up but that was a consequence too – as the company owner’s offspring I was left to take responsibility even if it wasn’t my fault!

I’d like to tell my shark consequence story too (there were a lot, not much air left and the 20’ water depth I started in was quickly over 100’ …) but I’d better get back to the relevant part of this story.

I have the most amazing woman in my life who is responsible for finding Maddie in some deep recess. I could say what has happened since was an unintended consequence but in reality was a predictable outcome.

Now let me warn you, this story doesn’t have a big oh my god moment, it has a bad unintended consequence but a very happy ending, so don’t worry! What it does have is a few things that may be points of note for others who are in the position I was. So, to the story …

It was a dark and stormy night.

I’ve always wanted to start a story with that classic line and this time I can! Because it was! I was out of town working; I’d had dinner and I was surfing as you do. The whole Maddie thing was very new to me and that night I got really brave. I decided to see if there was a local makeup artist who would be willing to work with a CD, keep my confidence and bring Maddie to the world. And I found one! She was so excited to be asked and to share the journey. The fact is people, there isn’t a single better person I could have asked. I had the best of luck once again. This girl is top of the tree, a tutor and has even worked with Oprah. Wow …

We planned a time a few months hence as I had things to do, like removing a 30-year-old beard, practise a bit on my own and finish some dental work. It also became a half day makeover / lesson that N and I would do together. Awesome!

So, with everything planned we suddenly went into lockdown. Again. You have to be kidding …

I kept practising when I could. I usually sent pics to N to see (I work from home, she doesn’t) and the comments were always positive. I had said to her that when I felt it was good enough would she be up to being greeted at the door when she got home from work. And the answer was a resounding yes.

And so came the day. I finally felt good enough for her to see. Now let me state, that was at a level a couple of steps below where I am now (and a lot of steps below where most of you seem to be). But I was ready. She said yes to my question, and I waited nervously.

The response when she arrived home wasn’t what I expected. She had tried clothes on with me, bought my first bra for me, been there through every step, but this time she freaked out for want of a better description. It was the first time I had ever seen her upset and I never want to see it again.

I need to compress the next few days here. It took a bit to figure out because N had no idea why she reacted that way, which actually was the biggest issue for her. But in the end, we got there. She had walked into the house to see a woman she didn’t know waiting there to greet her. I wasn’t there and she felt like she was cheating on me. Wow …

On the positive side I couldn’t have been paid a higher compliment.

But then came the unexpected consequence; I could never ever see her so upset again so Maddie went back in the box. Alternative gender expression was over.

Oh, but wait dear readers, there’s more!

I told N that was what I was going to do and told her it would still be great for her to do the makeup lesson, and all would be well. Now the astute among you will already have clocked my error – I made a unilateral decision.

Over the next few days I was made aware of my mistake and then some! Because of the awesome relationship we have we talked through everything, and Maddie was cautiously released once more. The conclusion was this – the difference was that it had been the first time I had changed totally from me to Maddie without N seeing any part of the change. She still wanted to do the lesson together and she would see how she felt, and if it was a problem we’d work out how to handle it.

So, came the day. The artist was up to speed with what had happened and was ready just in case. The first positive was she was even nicer in person and we are now good friends. Four hours later (she even delayed the next customer for us) she left the studio so I could dress. And guess what, not a single problem as Maddie became visible. Putting on a wig is the single most powerful thing any crossdresser can do. Seeing that happen just changed everything for N and there were no problems at all. Just the opposite.

Because it was a lesson the finish wasn’t quite passable enough for me to go to a mall and go shopping. But I rode shotgun on the way home, dressed, and we had to make stops in public places. Baby steps are good too …

So, a happy conclusion. But wait, there’s still more! It’s an unexpected rather than an unintended consequence. N loved doing it together and we have another lesson booked, this time at our house and it will extend to dinner and drinks. But here’s the thing – we’ve set up a whole makeup area with table and drawers and illuminated mirror and all that good stuff! I didn’t see that coming. Now N has a proper place to prepare in the mornings and if Maddie wants a session everything is already laid out and ready to go. That’ll save an hour!

Quite a thing I didn’t anticipate, which shows not all consequences are bad!

But there’s a lesson here too – if you are a crossdresser or gender-questioning and working through the stages with your partner, don’t go from 0 to 60 without a few periods of deceleration. Fortunately, it only cost me a couple of months not the whole kit and caboodle …

There’s really no rule book for what we do is there!

(I originally wrote this story a year or so ago. And while makeup lessons have happened here at home a couple of times, and the wardrobe and experience grow, the first big trip out with the girls has yet to happen. Yep, another lockdown followed by covid, and a flu that was even worse, all got in the way. As soon as the weather cools again here (in a few months), the hair can go again, and it will be time to make it happen!


10 Responses

  1. Maddie, thanks for sharing this.

    Sadly, I was also encouraged by my wife to dress in front of her with much the same consequences that you initially had – that was in 2014 and the story only came to a conclusion a couple of weeks ago after nearly 9 years of suppression, deception and frustration.

    It’s an incredibly tempting thing to do – for me it felt like it was going to be the final step to acceptance but ended up as the exact opposite because neither my wife or I considered what the outcome of her seeing me in far more feminine clothing than she would normally wear would be – it can, as it did in my case, disrupt the whole foundation of the marriage. Anyone considering this would be well advised to read your post because there are two important messages in there – the first is to think very carefully before doing it and the second is that if you’re going to do it, let your wife take control so that things can be done at her pace, not yours.

    I’m looking forward to reading a lot more from you!

    1. Hi Amanda. You are right. I guess the difference for me was that N discovered Maddie and encouraged me at every turn. Her reaction was so completely unexpected that it caught us both by surprise. Great that we sorted it but certainly a warning. It’s easy to focus on yourself and your progress while presuming the SO is progressing at the same rate.
      And yes, not sure if it’s a good or bad thing but Kandi has several more from me stacked up …

  2. Maddie,
    You made the point about the wig being the game changer , I still recall the moment after I had made a reasonable job of my makeup the man had gone after I finally placed my wig on .

    Being seen for the first time been was a mixed bag for me , I recall my daughter walking in my front door for the first time with her husband and daughter , she checked me over for a few minutes and then declared I’d done a great job on my eyes . My ex-wife dropped in for coffee and brought me our marriage certificate so I could proceed with our divorce , she walked in and threw her arms in the air saying , ” Oh my god , I can’t deal with it ! ” She stayed long enough for coffee and signed the papers then left after half an hour . She has never seen me since as Teresa as far as I’m concerned we remain friends and my door is always open , so the ball is in her court .

    I’ve never had a full makeover but I did make a trip to Boots some years ago to ask for a colour check to assess my concealer and foundation . The SA was delighted to help as she had never worked on a guy before , before I knew it she had made up the left side of my face . Out the corner of my eye I could see shoppers passing by the booth and doing a double take , it was a great day for me knowing I’d now got the basics right for my look .
    As a professional photographer I saw some terrible make overs , also the problem is they can be heavy handed , it may look fantastic but it’s not an everyday look they achieve . That was a lesson I had to learn when going fulltime , discovering how little I needed to apply to attend to everyday chores like going to the supermarket and putting fuel in the car .

    Having a wife or partner on board is great but as you say don’t go full throttle , it’s also important to remember they might have a change of heart . They may not understand your motives if it goes from the odd occasion to wanting more . Looking back seeing the guy disappear was the turning point for me , it’s finally when it all came together and Teresa came into being .

  3. Hi Teresa. It’s exciting isn’t it! I don’t think that anticipation of the moment will ever dimnish.
    And now I have an idea for another article …

  4. Maddie (and Amanda),

    If you have read my posts you will have learned that I too made this mistake. Newly married. She initiated the idea of putting makeup on me. I was so thrilled I told her I thought I looked pretty good in her long dress and I would just pop in the closet to show her. BIG MISTAKE. Her reaction was so strongly negative that I hid this part of me from her for the next 30+ years. Baby steps, my friends, baby steps. Be satisfied with a little and ASK before you act if you care about your partner’s feelings.


    1. Hi Lisa. I’ve read a number of yours including the Spousal Relationships and Two Spirit but just found the one you refer to. The Two Spirit one I completely relate to, as you will see in the future in a piece I’ve written. I came to that conclusion fairly quickly that that is me.
      While I’ve pulled the accelerator back a bit it’s more a case of keeping me in check rather than any other concerns. I almost feel guilty for saying this because I am in the fortunate position of having not one, but two completely supportive women. N, who is now my fiancé, found Maddie and gave me all the space I needed for her to develop. We are the same size, and the instructions are to try and wear anything she has. I wish our shoe sizes were the same! My BFF has loaned me wigs and given me nail polish. There are absolutely no limits to what I do or when. It is completely up to me.
      Not for one minute do I take that for granted or abuse that level of tolerance and trust, rather it is just another great thing we share between us.
      So, the reaction that first time was so out of character that it became a wakeup call. Probably one I needed. But now it is all back to where it was with the ability to develop things further if I want. We have a level of sharing and trust that is beyond anything I’ve ever experienced. There’s nothing like sharing your deepest and darkest secrets!
      I really am the luckiest one here.

  5. Add me to the list of those who think a wig was a big turning point.

    When my first one was delivered, I put on a nice dress along with some lipstick & eyeliner before putting it on. I walked into a room with a full length mirror, saw a lady looking back, then sat for a while admiring the view and deciding I was ready to show Fiona to the world. I haven’t looked back since.


  6. There’s nothing quite like it Fiona …
    I purchased a whole lot of styles and colours from AliExpress. It is fun to see what works with various clothing styles and they are cheap.
    The last time our makeup artist came around for a session she also stayed for dinner. Brave me ate while fully dressed right in front of the feature window where anyone could see. As I keep saying, baby steps … But, the problem was the hair tended to be uncomfortable around the eyes and mouth. No problem for photos but difficult for practical use. So I bit the bullet and ordered a human hair model. I haven’t had the chance to dress with it yet but it feels so much better. Hopefully I have the style and colour right because one kills the budget for a while …

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