Crossdressing and Compromises

I read every single comment that is posted on this website. Promise.

Sometimes a comment will be a little critical of a photo, an opinion, or a post. Sometimes I am very reluctant to admit the comment which contradicts my opinion has, well, a valid point.

For example!

Smiling in photos.

I will always believe that some pictures look better without a giant grin on my face but yes, for the most part, the best pictures are when I look like I am actually enjoying the photo shoot.

I tend to ignore the trolls in the comments and some comments spark an idea for a post. Some comments completely miss the point of what I am rambling on and on about.

But that’s how it goes.

Usually a comment will trigger a response in my mind but I usually don’t post it. Sometimes my unposted response is a defense of what I wrote or a reiteration of what my post was about. I like to think that I tend to stand by what I wrote AND I like to think that I will admit when I am wrong or perhaps my perspective is a little short-sighted.

I write a lot about how our gender identity and crossdressing impacts our relationships and our partners. I discuss boundaries and honesty and full disclosures. I want to make it clear that a relationship with someone like me, someone like you, is likely going to complicate a lot of things AND this side of us isn’t likely going to go away.

Essentially people who are committed to staying in a relationship once this revelation comes to light will have to try to find a way to make it work.

Aaaand it’s not easy.

If there’s one thing I try to emphasize in discussing relationships with someone like us is that I really think it’s important and crucial that we listen to our partners and consider how this side of us impacts them. I talk a lot about being honest with them.

I also discuss staying within any sort of boundaries that are agreed upon.

When I talk about these things, it’s not unusual for me to receive emails or read comments about how this side of us can’t be a one way street, if you will. I tend to take the side of our partners if there are “sides” to this. If they have a request or set guidelines then it’s important that we adhere to them. Afterall, this is a lot for them to take in and it’s not something that they necessarily signed up for. I suppose I am prone to feeling a tremendous amount of guilt from the stress this side of us can cause that I am quick to let our partners, well, set any guidelines (if you will), that they are comfortable with.

It’s been suggested that I tend to oversimplify these… agreements.

And… you have a point.

Every relationship is different and most relationships that work are usually the result of communication and honesty and partnership and dedication and, yes, compromise. Before there is any sort of commitment to each other, whether it’s an engagement, a child, or a major financial investment, such as a house, I do believe you need to disclose this side of you to your partner. This is part of being honest, this is part of communication.

I think it’s crucial if this side of you exists, you need to let your partner know about it. IF this side of us is, essentially, a “deal-breaker”, we need to let them make that call before both of you buy a house or an engagement ring.

If you are honest and upfront with your partner AND the relationship continues, well…. you did what was right and are letting them make decisions with the information you disclosed. They know now what they are getting into.

Goodness that sounds depressing and I don’t mean it to be.

Coming out to someone before it gets serious and coming out to someone after ten years of marriage and three kids are completely different.

And yes, I acknowledge I am oversimplifying all of this again but I try to discuss things like this very broadly and still realize that every relationship is different and coming out is easier said than done.

Anyway, I will never claim to be an expert in anything. I can only speak from my perspective and my experiences. Most of what I say or feel or think is a result of my own relationships. What worked, what didn’t… and how my gender identity or clothing preferences impacted the relationships.

When it comes to my relationships, both past and current, they almost always come down to a few core principals which almost always impacts whether or not the relationship failed or if it is/was successful.

When I say successful I am referring to how satisfied and content and healthy the relationship is/was. A failed relationship is not necessarily about it ending, but more about how the relationship made the people in it felt.

Does that make sense? A marriage lasting thirty years isn’t necessarily an “achievement” if one or both people in it are completely miserable. Love is not a victory march, after all

I am asked a lot about how my wife and I make our relationship work. This is going to sound a little unsatisfying because what “makes us work” is really quite simple. Honesty, friendship, and respect are what guides us. These principals aren’t just limited to what is in my closet or how I spend one or two Saturdays a month. It extends to how we take care of our home, how we manage our finances, how we care for each other. Again. this is objectively oversimplification but I assure you these things take commitment and work.

When it comes to this side of me, there was no… hm, formal sit-down meeting which laid out any sort of boundaries or rules, if you will. As my gender identity evolved so did these conversations. My wife let me know what she was comfortable with as well as any requests about what malls she would prefer I avoid. We had many conversations about what she was feeling or thinking or what she was afraid of. We still do.

As who I am changed, her feelings about this side of me did as well. When they did, we would have a conversation. Like anything, when a situation changes it’s not unusual to reconnect about it.

This was WORK. This took a lot of courage from my wife. She knew that who I was made me happy and it takes a lot of bravery to tell someone something that they may not want to hear.

Aaaand I didn’t always want to hear that my wife would prefer I not go to certain salons or malls because she has friends who frequent there and it would increase the likelihood of being seen. But I listened and pushed the Pink Fog away just enough to understand and respect her feelings and fear.

Fast forward to today.

Things are good. We’re both comfortable with how things are with Hannah. It is very “it is what it is”. And what we have works for us BUT would likely appear completely baffling to anyone else. Through patience, listening, and a commitment to see things from each other’s perspective we arrived to where we are. Not only with my gender identity, but with everything else.

Previous relationships weren’t like this. Not only in terms of my wardrobe but also in terms of other elements that are part of a relationship. And thank God they didn’t work out. Everything that has happened in my life, whether it’s a relationship ending or anything else, led me to the life that I now.

So yes, I suppose everything happens for a reason.

The first person I came out to was the girl I was in my first serious relationship with. Of course, as serious as a relationship can be at 21 years old. Simply put, it was requested that I, well, don’t crossdress anymore. End of discussion.

And I don’t mean to make this person sound like an unreasonable bitch. She had every right to be in the type of relationship that she was comfortable with. AND! She was like 19. AND! This was like 25 years ago. The world wasn’t as accustomed to the nuances of gender identity as it is now.

As important as crossdressing was to me at the time, I agreed to stop. I thought I could.


I really thought I could.

I agreed to stop not because I wanted to, but because I was… I was so broken after the difficult home life I had with my abusive father. I was so desperate to be with someone. I wanted stability, I wanted love. I would have agreed to ANYTHING for this, even at the price of quitting crossdressing.

The need to be with someone superseded everything else. I was so insecure and codependent I think I would have agreed to anything than to risk the chance of the relationship ending.

And looking back, goodness I needed help. Thankfully I got it. Therapy helps, bitches.

The relationship ended and I was secretly glad it did. I wasn’t happy. I knew I needed help. And I’m glad she ended it. I never would’ve had the courage or confidence to do so.

Again, she wasn’t a horrible person. I wasn’t an easy person to be in a relationship with then. I had a lot of work to do on myself.

Essentially crossdressing wasn’t something we could compromise on. But I never TRIED to. I had zero self-esteem. I couldn’t negotiate, if you will, anything. I wanted to be in A relationship, no matter how much of ME I wasn’t.

In many ways I will be forever grateful for this relationship because once it ended I was able to look back on it and really realize how much work I needed to do on myself after the difficult teenage years I had.

My next significant relationship was also an indication that the progress and the therapy I had after the earlier relationship was helpful, but I still had a few things to work through. This relationship was very different in many ways. I came out to her and it went pretty well. I wasn’t the first crossdresser she had met.

There were boundaries but they really didn’t impact anything. I wasn’t Hannah then, if you will. I wasn’t going out of the house en femme. There was little need to compromise because, well, it was never really an issue. It was… an unconventional relationship in a lot of ways. Eventually it just… ended.

If my marriage has taught me anything is that marriages take work BUT it should be, well, mostly enjoyable and worthwhile work. Communication isn’t always easy but it’s worth it. It has a payoff, if you will. I’ve never regretted the work and energy my wife and I have put into our relationship, whether it’s about gender identity or finances or simply creating a life together.

One key to making my wardrobe preferences work is my wife being open and honest with her thoughts and feelings about it. For my part, although there were missteps, I was able to communicate to her that this is who I was and despite all my previous efforts to STOP, I couldn’t. I didn’t WANT to.

So, we talked. For years. With every new part of my “journey” we talked again. The situation changed, it evolved, so reconnecting was essential. Of course, it sounds so simple to say it like this. There were tears, there was tension, there was frustration, there was… a lot.

BUT neither one of us were stubborn about this or really anything in our relationship. If there was something that entered into our lives, whether it was an expensive household appliance that needed to be replaced, or an unexpected financial THING, or me embracing my bi-genderness, we approached it with the mentality of “well, how do we make this work?”.

Again, I don’t mean to gloss over anything or minimize the stress my wife experienced with who I am. Who I am, what I have now was never the result of my wife understanding this side of me. It was her understanding that yes, this is a little unusual but this is who I am.

It does go both ways. My wife loves listening to murder podcasts while she works. Do I understand this? No. Do I understand this makes her happy? Yes.

And I don’t want to trivialize anything. Listening to a podcast and doing a lingerie photoshoot are not the same thing.

Are there boundaries? Yes. I avoid a certain mall when en femme at my wife’s request. If I am doing SOMETHING new (such as when I started lingerie photo shoots) then we reconnect. I don’t want to be in a relationship where I can do “whatever I please”. That’s not how a committed relationship works. Respecting and listening to your partner is how it works.

I am aware of the stress that this side of me can bring into my marriage. All of THIS is an act of balance. Being careful not to overwhelm my wife AND feeling fulfilled. Again, compromise. This balancing act wasn’t easy as I was often swept up in the Pink Fog and let Hannah just… take over. She quickly wore out her welcome. I was afraid, and for good reason, that my wife would come to resent this side of me because of how much of my life and our interactions revolved around Hannah.

But I dialed it back. Thank God. Not only for my wife’s benefit but also for my own. I have a habit of letting something dominate my life (good or bad) and this side of me wasn’t much different.

I do regret how this side of me impacted my wife and how she felt. I don’t regret who I am but like I’ve said in other posts, it’s not THIS side of us that is usually the problem, it’s what this side of us made lead us to do.

So, when you comment or even think to yourself that discussions about boundaries and rules about this side of us aren’t a one-way street, I want you to know that yes, I agree with you. Who we are, whoever we are, is, well, this is who we are. We shouldn’t neglect who we are, and we need to be honest.

Love, Hannah

boundaries being a “one way street”

Not knowing how to “compromise”

Feeling too much guilt about this side of me to feel that I can “negotiate”

8 thoughts on “Crossdressing and Compromises

  1. Friend Hannah , Pardon a “quibble” ? I might favor therapy “helps” more precisely than “therapy works” . “Works” might suggest ‘solves’ , ‘cures’ or ‘corrects’ . Helping us understand (and hopefully accept) ourselves is the first step towards dealing with the world and those special “others” who enter our lives . In hopes of a dialogue. . . Always , P.D. Miller


  2. Hi Hannah
    As a t-girl, I now always enjoy your take on things. Not in a relationship so I have a lot of latitude, but can easily see that respect for your wife’s rules & boundaries trumps the ink fog. in addition to good communication.
    Thank you for always making good sense and doing it with unique style.


  3. Hi Hannah, I am so glad that you post the thoughts and concerns that you encounter in your life. I have been following your blog for years now, and it is a nice addition to every one of my days in which you add to your writings. I agree with nearly everything you say, always, but the notion that ‘everything happens for a reason’ is simply silly, not true, and founded in superstitious/religious thinking. Lots, and lots of things happen for no reason at all, they just happen, This is drifting into what is called ‘epistemology’, the philosophy of how one knows, but life contains many, many nearly spontaneous events, of which we cannot predict or explain. It seems clear to me that you have arrived at a place in your life intellectually, and emotionally, where you trust yourself, and that is a really, really good thing., Keep on with that, and have a good Monday evening! Best to you, Marissa in Ohio


      1. Ooops, now I feel like a 7th grade teacher; sorry. Thank you for the clarification of your intent. Makes sense, for sure. I just did not pick up on the tongue-in-cheek effect. I think I might have written “…everything happens for a reason….NOT!” or “…everything happens for a reason…..Riiiiight…” Waay overthinking this. Have a good Tuesday!


  4. Having failed twice, I’m in awe of transgender people who maintain positive relationships. I like to think I have learned from their examples, even though its a bit late in my own life.


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