There comes a period in every cross-dresser’s life when the time comes to have THAT conversation with your significant other. It can be stressful; it can be nerve-wracking. And the fact is, there is almost no information written anywhere on how to handle that conversation or to react to what you might be told.
About this time you are wondering what the hell planet I’m on, as there is so much written on the subject, including the infamous An Open Letter to Our Wives post on this blog, which sums up the situation so well.
Actually, I’m not going mad – I’m not talking about THE conversation I’m talking about THAT conversation – that conversation you have when you’ve been doing this for a while and you feel the need to make sure your wife or significant other is properly on board and that there are no unseen issues bubbling away that could derail things. I haven’t seen a lot written about that.
I instigated that conversation last weekend.
The first question you may ask me is, why, specifically, why now?
And with apologies for repeating things from my recent stories, by explanation here’s a summary of where I’m up to.
There was no Maddie until late 2020, at which point it was like a spotlight had been switched on. I married the person that found her. After doing stomach-churning things like contacting a makeup artist to see if she would help me (that obviously went well, we remain friends and she is due here for dinner in a few weeks), and then, after covid stuffed up a year, getting into trying my own makeup and finding Maddie’s look, I made progress. That was nearly derailed after the first time I greeted N at the door fully dressed, not because it was so bad, but because it was so good. We got through that, also getting through the disastrous work situations for both of us for a period of time, (seems to be a theme on this site …) and now on the other side, normality has ensued.
But things have changed.
I keep telling everyone that will listen that I have the most supportive wife in the history of crossdressing. And I have. I have the proof. But that isn’t something to ever be taken for granted, and like a good marriage, needs constant adjustment and work.
What has changed is that I’ve added a second makeup artist to the team – she too has become a really good friend, (and confidant, anyone we share what we do with has to be a confidant with the amount of trust we put in them), and she recently took me out into the big wide world for my very first outing after our first makeover together. I lived. But worse (yeah, I know you are all saying I told you so) I LOVED it!
Outing 2 came about pretty quickly after, and was the first involving my darling as well, plus the makeup artist. I loved it even more! I found myself in trouble. A silver and black dress only added to the grief – I need a GIRL’s NIGHT!
Now please don’t misconstrue what I say next, because there isn’t one single one of you I’ve communicated with here that I wouldn’t do a trip out with, but my end game is just to be one of the girls, with the girls, for a period of time, and enjoy everything about doing that. I think that is because, while we all accept each other, being accepted by a group of women as one of them, even if just for a short time, is just another level.
Team Maddie currently consists of wife, my BFF, my two makeup artists, plus now one of the new MUA’s friends, (who is really excited about being involved), and our brow girl. The latter is going to prove to be one of the most important people in this story, as you will soon see.
I told Team Maddie I was ready for a girl’s night out, and what I found was a burlesque show with individual tables, where I expect lots of champagne to be for sale.
Our table is now booked and four of us are attending the inaugural girl’s night out with Maddie. I should print t-shirts, or maybe get specially embroidered panties, to mark the occasion.
This is next level as the tables are close together, lots of people will be there in a compact space, and I know, despite my best planned efforts, there is just no way I will pass in front of all of the attendees. Since I haven’t faced that situation yet, I don’t know how I’ll handle that when it happens. Probably back to the stomach churning … What I do know is I will have three wing women / party girls determined to have a great time and you wouldn’t want to get in their way or upset them… They will have my back. I’m going to have an awesome time with them regardless, and I’m picking the inaugural adventure will be one that will be pretty hard to top.
Which brings me back to that conversation.
Knowing we were heading out in a couple of weeks for the show, I got straight to the point and asked my darling if she was comfortable and still happy about Maddie’s existence, about going out with her, and being with the others that were on the team.
The answer was, yes, of course. She wants to see me happy and to explore every part of me that I want and need to. (I would like to think that the photo with this post shows that happy is a given …) The first really interesting thing was that the conversation started with a talk about how she felt about being with Maddie. When with Maddie she is completely disconnected from me. She is with Maddie. My BFF said the same thing when she officially met Maddie in person a few weeks ago (probably a good thing as we work together most days). There is a separation. The interesting thing is I feel exactly the same way. We are both so secure in our relationship that there is just no fear or jealousy in what we each do. I text and talk to females. She texts and talks to males she was previously close to. Neither of us hide that. The disconnect is a positive.
And that is beneficial as we go forward. We can both be ourselves in our respective roles. I hope that makes sense and I’m communicating what I mean, because I feel I have a completely separate personality when Maddie appears. And I know that since I’ve been out in public, there is a whole lot more of that kicking in. How I react with females as Maddie is quite different to how I do when not.
So, the conversation was going well. We talked about all the girl things we do together (I’d had a stocking crisis the previous day … we solved that the day after the talk) and we both love what we do, so no problems there.
And you know it’s coming –
BUT …
It was a simple but, and I should have picked up on it some time ago. Team Maddie is a team that has been developed by just Maddie, not us. And while I can talk intimately with each of them, N doesn’t have the same relationship. With one exception, our brow girl. She joined the team through N, and was her friend before that. I missed how important it was for my darling to have a far more intimate connection to someone in the team.
Brow girl (BG) can’t make the first outing for financial reasons. I’ve been where she is, so I completely understand. She was still invited (with the understanding relayed to her that I knew she wouldn’t be able to). Now I’m already organising the second girl’s night out and it will be all about her availability. And BG is pretty special. We messaged today and she says she is grateful I want her as part of things and super excited to officially meet Maddie. I’m not so sure I’ll like her so much next week when I have my first ever chest wax, but this week she’s lovely!
But she is N’s friend first, as well as part of Team Maddie, meaning my darling has someone she can talk to in depth on this topic. She’s told me some of the sorts of discussions they’ve had, but I really don’t mind if she doesn’t. She needs her outlet too.
So, me being me (should that be both of me?) I had to (over) analyse and finish with a summary. I asked my most favourite person, the one I hate being away from for even a minute, if I had this right – she has no problem with Maddie and her exponential growth in recent times, she is happy to go out with her at any time for things like the burlesque show (hell yes, can’t wait, was the answer to that one), that she is comfortable with Team Maddie, even though she isn’t as close to many as I am, that having BG as part of it is a very important part for her (as she explained, it’s not like she can talk about it with her sister or other friends, and has to be careful about saying what we are doing in case they want to join; I really hadn’t thought about all of that …), and that we continue to see where this goes while continuing to enjoy every aspect of our life and relationship.
The answer was a simple, but resounding, yes. I truly am the luckiest girl here.
And also, a much more aware one now. I won’t miss the signs again. I’m really pleased I was proactive in having the conversation.
After the weekend N thanked me for making it a really good one. We walked a lot and talked, rather than driving for some things as we usually would. It was quality conversation, and she made the point about how she felt even closer at the end of it.
Mind you, any weekend where we go out together to get our nails done, then go and buy stocking together, can only ever be a good one!
If only every wife could be like mine. Never will that be taken for granted.
2 Responses
Maddie, fantastic post and a much needed new angle on the whole wife thing. Probably my own biggest frustration here is that I can’t keep the dialogue going with Mrs A as she wants nothing to do with this side of me. I’m quite happy for her not to be involved (in fact I prefer it that way) but it often feels like there’s a huge elephant in the room (and I’m not referring to Mrs A here!) that never seems to go away.
I particularly empathise with your point about your end game being to just be one of the girls and that’s very much how I feel although, as a loner at heart, my version of that is just to be out being myself.
And as for passing and your stomach churning at the thought of being very close to others at the burlesque show, the way I overcame this was to stop striving for the impossible dream (in my case that I could be hot enough to win Miss Universe!) and, instead, just aim for something that was achievable – passing as trans which I do 100% of the time. Firstly at a range of six feet or more, few people realise I’m not what I appear, secondly no one who does realise knows whether I’m an occasional CDer or full time transitioner and thirdly, few people care (and I have had a couple of truly memorable experiences because people know).
In short, you’re going to be fine and I think we’re all looking forward to hearing about it.
Maddie,
You’ve no need to excuse yourself as being with the “GIRLS” is an inevitable step , it isn’t the same as being with a group of transgender friends , some crave it and some prefer the security of trans social groups .
As you’ve realised it does raise new questions and new dilemmas , you have stepped into a woman’s world and it takes time to find a happy balance . Yes there are still ” What ifs ” but from a different angle . I was going to make the point again about using CROSSDRESSER as a verb rather than a noun , you label yourself a crossdresser but there is now something more happening , you now crossdress because you have discovered a deeper reason why . Somehow I sense that from posing the question to your wife , while she says she’s OK she may be having deeper thoughts . The fact she has chosen to come aboard could have another motive because she still has full knowledge of your actions and still has the last say in controlling them .
Even being fulltime I obviously had to take care , being read was hopefully not an option , it didn’t stop me joining various groups but I had to take it slow , building friendships gradually . My art has been my saviour because I share something in common with them , they got to know me through that . The first time I was invited to lunch it was one to one now there’s a group of four , the confidence of one person spread to the others . This gave me the confidence to take day trips and then full holidays , I admit I’m slightly nervous about my first cruise , twelve days is literally pushing the boat out for me . Obviously the new Supreme Court ruling has concerned me but I’ve just stayed under the radar and continued as before .
I guess the bottom line is Maddie exists and people know that , you know your true feelings why she exists , yes the genie is out of the bottle and she may never fully return to it ! No matter what you do or say now the net will widen , people do talk , I found it was impossible to pull the net in I had to go with it which I’ve never regretted .