Crossdressing and Guilt

I don’t think crossdressing is a big deal.

I mean, obviously presenting as a gender that is different than the gender that is stated on my birth certificate is an enormous part of my life and who I am and I am always wearing clothes that are “for girls” but I have absolutely no… negative or uncomfortable thoughts or emotions about this side of me or about this side of my closet.

I mean, yes I get a little paranoid about someone seeing my bra strap in male mode or the lacy edge of my panties peeking over the waistband of my pants but really, that’s about it.

Of course, when I was younger the FEAR was there, of course. The fear of getting caught, the fear of someone finding out. This fear ranged from my mom arriving home earlier than I expected to the fear of a friend spotting me at the lingerie boutique at the mall.

But guilt wasn’t something I felt very often.

I never thought I, as someone that is legally a boy, was doing something wrong by trying on a dress. I’m not breaking any laws after all. It is not immoral to wear panties. I am not hurting anyone by sleeping in a nightgown.

When I did feel guilt it wasn’t because of crossdressing itself. I felt guilt because I was wearing something that I told someone I wouldn’t wear.

Again, I don’t think crossdressing is a big deal. And I think for most of our partners it’s not a big deal. No, it’s what we do that is associated with crossdressing that is an issue.

What I mean is that I often get emails from partners of crossdressers and many of them tell me that, for the most part, they really don’t mind that their husband wears panties. The issue comes from their partners lying about their crossdressing or being, well, reckless about it.

For example, a crossdresser’s wife may have no problem with what their husband wears to sleep, but it’s what their husband wears to bed. Does that make sense? Some people don’t want to be intimate with their partner if their lover ALWAYS wears lingerie for sexy times. It’s typical for someone to feel it’s no longer about lovemaking but more about an opportunity for their partner to wear lingerie.

Some partners will express that they are frustrated when their husband spends more money on clothes than they can really afford. Neglecting a car payment because you purchased a new pair of high heels is, well, not a good situation. It’s not necessarily about the heels, it’s about not being fiscally responsible.

Going outside the agreed upon boundaries is also a cause for concern. If your partner asks you to not post photos online or they ask you to avoid certain stores because you may inadvertently bump into someone your partner knows… but you do these things anyway… it is a complete violation of trust. Again, it’s not exclusively the crossdressing/presenting en femme that is the issue, it’s breaking a promise.

Why do we do these things? The Pink Fog.

But this post isn’t about The Pink Fog. It’s about guilt.

The first time I felt real guilt was when I was in my early twenties. I had come out to someone, a girlfriend, for the very first time and it didn’t go the way I had hoped. And that’s okay. This was about (oh God) twenty-five years ago and we were both young. We weren’t mature or experienced enough to have THIS element in our relationship and I was still working through a few things. Besides, having a non-cisgender partner is a lot for someone to go through.

My hope was for her to suggest hitting the mall to go shopping but she essentially had two requests:

1. That I stop
2. That I don’t discuss this again

I mean, good for her..? She was very clear about her boundaries and letting me know that she wasn’t a fan of having a crossdressing partner. It was a very black and white conversation.

Were these fair requests? Maybe not but again, we were both young and in the relatively early days of a relationship. It’s not like this was a revelation thirty years into a marriage and THIS was one more thing for the two of us to handle and communicate about.

Fearing the idea the relationship ending I quickly agreed. I mean, I was naïve. I thought I could stop.

lol.

I mean, I knew I wasn’t ever going to stop BEING a crossdresser but I thought I could resist.

Again, lol.

Please understand. Her reaction and her requests don’t make her a bad person. This conversation was, in a way, a product of the times, as they say. The complexities of gender identity weren’t as discussed or as familiar as they are today. I also could have come out in a more… accurate way. Back then I was a CROSSDRESSER and with that word came all the baggage that the word came with. If I were to come out to anyone today I would use different language.

Anyway.

I told her I would stop and that was, more or less, the end of it.

Sort of.

We wouldn’t discuss IT very often or for very long after that initial conversation… but stopping? No. But God help me I tried.

Mind you, I didn’t try to stop because I thought there was anything wrong with crossdressing. I tried to stop because I told her I would.

It didn’t take long for me to explore her side of the closet when she wasn’t home. It wasn’t unusual for me to drive to a boutique to try on dresses.

The siren song was too powerful for me to resist.

This is when, for the first time, I really felt guilt about what I was doing. I was going behind her back, I was unquestionably breaking a promise.

Of course, whether or not this was a fair promise is another story, but regardless I was still doing it.

I was afraid, once again, of being caught. She would forever remember The Talk so it wasn’t about keeping it a secret that I was a crossdresser, it was the fear of being caught after my promise to her.

Listen.

I don’t think there is ANYTHING wrong with crossdressing.

Or, to be more specific, I don’t think there is anything wrong with crossdressing ITSELF.

I believe in justice and morality. Which isn’t necessarily the same thing as law and religion.

Let me explain.

I don’t think it’s unrealistic to fear that crossdressing will be illegal in some parts of the United States in the future. Now, before you think I am being paranoid or an alarmist, let me clarify. It doesn’t take too long to find stories of people protesting drag shows or banning books with LGBTQ+ characters or stories. The justification for these actions are usually very subtle. In many cases the laws that are being discussed or passed usually don’t explicitly say “this book is banned because it has a part where two boys kiss”. It’s typically something more… broad such as banning the book because it has “adult themes” or whatever. Drag shows aren’t banned because it’s now against the law for a “boy to wear a dress” but it’s because someone thinks a drag show is about SEX.

Now, you may be thinking that regulating drag queens isn’t going to be impact you. Afterall, you might not think of yourself as doing drag. I certainly am not a drag queen. But for some people these nuances don’t exist. For some people there is not difference between a t-girl wearing a t-shirt and jeans running errands and a drag queen in towering stilettos lip-synching to a Madonna song at a gay bar.

It’s not unrealistic to imagine a law passing that says something along the lines of it being illegal for anyone to wear anything that conflicts with the gender on their birth certificate. If that happens, clothes could be “regulated” and a state could essentially have a dress code.

This is what I mean when I say I am afraid that “crossdressing” will be illegal. If this happens I know I would be “breaking the law” by wearing panties but all the laws in the world will never convince me that I am doing anything “wrong”.

When it comes to religion, I am well aware that there are religious texts in holy books which state, or are interpreted in a perspective that says crossdressing is immoral or is a sin.

Although God may be omnipotent and all-knowing, I really, really, really don’t think any deity cares what I am wearing. “Thou Shalt Not Wear Panties” could be the number one commandment but I still wouldn’t think I was a sinner.

Of course, I would also need to be a Christian to believe that not adhering to what the Bible says making me a sinner. I am not a Christian. If anything, I am agnostic.

But this post isn’t about religion. It’s about….

Um. Hang on, let me reread what I wrote.

Oh yes, it’s about the guilt some of us feel when we wear what we want to.

If crossdressing was clearly a sin or a crime, I still wouldn’t feel I was doing anything immoral. If I speed, sure, I might feel guilty about breaking the law. When I was younger and raised as Catholic I felt guilt if I didn’t attend Sunday service. But I didn’t ever feel guilty about crossdressing itself. Like a lot of aspects to THIS, it’s usually not about wearing a dress, it’s about the… actions that are associated with it.

I write a LOT about relationships and crossdressing. I’ve gotten countless emails from partners of those like you and I. Every crossdresser is different, every relationship is different and it goes without saying that every relationship with a crossdresser is different. But there are a few broad generalities I’ve realized.

I am always pleasantly surprised when I see an email from someone who tells me that their husband crossdresses and, well, they don’t mind at all. They may not understand it but they know that this is who they are and will unlikely ever change. They have gotten used to their man wearing panties or even presenting en femme. It is what it is.

But the… tension and frustration usually comes from aspects that this side of us can bring. Obviously I buy a lot a of clothes but it’s nowhere as much as I used to. The Pink Fog hit me hard and I often spent more money on shoes than I should have. My wife and I keep our finances, more or less, separate but when I couldn’t afford to pay a bill on time because I *had* to have a new pair of stilettos then things became understandably tense. I was being irresponsible.

For some of our partners there are frustrations involving intimacy. Some spouses tell me they don’t mind that their husband wears lingerie… but they have requested that they not wear it during sexy time. Similarly some wives tell me they think that the only reason their husband is intimate with them is so they have an excuse to wear a pretty negligee.

Finances and intimacy are significant parts of any relationship. If anything impacts these things, whether its’s crossdressing, an expensive hobby, or working too much, a home can become very tense.

Bringing crossdressing into a relationship is going to involve a LOT of change. It will forever impact the dynamic between two people. Boundaries, rules, and requests are pretty normal. Some of the more common guidelines include:

1. No lingerie during sex
2. Not posting photos online
3. Avoiding certain parts of a town when out en femme
4. Discussing things with each other before coming out to anyone new

I think these are all pretty reasonable, to be honest. Again, this is a lot to put onto our partners and I think it’s perfectly acceptable for us to make a few concessions.

bUt it’S mY LifE you might be saying. You might feel you should be able to do whatever you want whenever you want. If you feel that way then why did you get married? A relationship is about compromise and creating a life WITH someone else and committing to making it work. If a person wants to do whatever they want whenever they want then maybe, just maybe, they shouldn’t get married.

But that’s just my perspective.

Just like I get emails from our partners, I also get emails from people like myself. It’s pretty normal for someone to share with me details of their relationship and how they make it work or ask for my take on something. It’s also not uncommon for someone to, well, confess that they are violating some of the agreed upon boundaries.

I promised my wife I wouldn’t post pictures but I have been doing so on a crossdressing website

I promised my wife I wouldn’t go to a certain mall en femme because a lot of her friends shop there but I went there anyway

I think you get the point. It’s the violation of trust that is the problem, not the crossdressing ITSELF. Their partners are fine with this side of them but sometimes this side of us makes us prone to doing things we shouldn’t.

Lying about this side of us is unfortunately not uncommon. We might lie about where we went en femme (such as the mall example), not that we went out en femme. Again, it’s not about BEING en femme that is the issue, it’s about the lie.

Does that make sense? I hope so because I am moving on.

With these confessions comes the guilt. Again, it’s not feeling guilty FOR crossdressing… it’s the guilt that comes from activity and behavior associated with crossdressing.

I am not writing this as a lecture or anything like that. I am no angel and I have made many mistakes. Crossdressing has led to me to making decisions that I regret. Some mistakes were financial, some were within my marriage, especially in the early days when Hannah was emerging. I talked and talked and talked about HER and about clothes and every conversation my wife and I had likely had something to do with Hannah. It overwhelmed my wife and these one-sided discussions left no breathing room for her.

Once my head came above the water I could see how selfish and inconsiderate I was. I felt remorse and a tremendous amount of guilt for being blind to how my wife was feeling.

Again, it wasn’t crossdressing itself (although there are feelings our partners have about that), it was what came with it.

Crossdressing is, for the most part, legal and, in my opinion, not unethical. There is nothing immoral about wearing what you wish. Sure, social norms tell us differently but those are just norms. At one point it wasn’t the norm for women to wear slacks or for women to dine without a male companion. Things change… but it’s best when things evolve.

For those who feel guilt about who you are, think again. Religion, politics, and social norms are very likely the reason you feel this way. Spend a moment and consider if this guilt is because of these intangible reasons. For the life of me I can’t even fathom why it is “immoral” for me to wear a dress. I can’t rationalize why any government spends even a day debating about a law that impacts what someone is permitted to wear.

Hopefully there will be a day when we look back on these days and wonder why we as a society cared about the clothes people wore.

Love, Hannah