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.


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.


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.


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

14 thoughts on “Crossdressing and Guilt

  1. Hi Hannah,

    Whew there is alot to unpack in this one.

    I agree with you on most things but I am not in full agreement on the relationship side. I believe this knife cuts both ways.

    When a partner sets boundaries and conditions on how to express who we are this also contributes to shame and guilt and hiding. We should not always bend to the will of our partner. This can be very controlling on their part.

    I know this will lead to a discussion having open communication. In this case that often does not work. Most of us already have internalized transphobia so our guilt and shame prevent us from pushing for what we want or need.

    Sometimes I believe you express you transgender status to you partner. After that you just let it evolve. If you don’t, then that is where the hiding and secrecy comes in.

    I dont believe this is as simple as setting boundaries and conditions then sticking them.



    1. I admit much of what I discuss when it comes to marriage and boundaries comes off as fairly black and white. There are always gray areas and opportunities/needs to compromise (on both sides, if you will).

      Love, Hannah


  2. Hannah, I see myself in so much of what you wrote. My wife has never liked that I have hidden my dressing from her, and even now does not know the full extent of my wardrobe or that I (rarely) go out dressed. That lack of honesty is more of a barrier than the act of dressing, although I don’t think she is happy with either. Do I feel guilty for not telling her what I am doing? Yes, but only after I have had a good time.


  3. who says female cloths are for females? what they wear look pretty, silky, satin signer skirts and blouses. big deal. nylons are much more then long johns. women have their own name for clothing, pants are slacks skirts are blouses, skits are short pants. the make up well it’s a sexy thing to put on and make you look pretty, perfume is nothing more than a smell, either feminine smell or more like ah do not sure what you would call it male smell Colgan. Earings well men wear earrings.. i love wearing what society calls for woman every day and love the fit and feeling


  4. Surely we all can agree that children should not be exposed to sexual things like drag shows, books and magazines, etc., showing genitals and sex acts and such things that children’s minds are not mature enough to be exposed to and, very likely, will adversely affect them in life, as any truthful and reputable psychologist or psychiatrist would attest to.
    Also, it is highly unlikely, in our liberal society nowadays, that any government is going to ban cross dressing. If so, I would be one of the first to protest. I also avoid the problems you mention by not divulging my “hobby,” so to speak, to anyone.


    1. ..drag shows, or kids beauty pagents, or children’s dance recitals, or especially dance car washes or professional sports cheerleaders or commercials or music videos or beaches particularly with bikinni’s or mini skirts or especially the Bible with all its explicit sexual language and violence. Please, please, please more government regulations.

      Reputable and truthful psychologist and psychiatrist are way more trustworthy on drag shoes then they are on how to treat kids with gender dysphoria or preventing related suicides.


  5. Comparing apples to onions doesn’t make sense – but common sense and decency does. The problem is that children are being exposed to sexual activity and genitals – this is immoral, indecent, and harmful.. If you are a parent/grandparent, like I am, you would know this and be against it wholeheartedly. This is why my adult kids don’t allow their kids to watch these things on YouTube and such sites. And one doesn’t have to be religious or of any political persuasion to realize this crap is hurting children!


    1. well into today’s society it’s all about seeing T.V shows kissing and having sex, but it is not shown. for men kissing me having sex with men, we don’t see that part. we know in some shows that women are lesbians or men are gay. we don’t see men dressed as women. back in the late 60s we seen commercials about toys for kids, then later in the afternoon we seen commercials about women panties or bras, then in the evening we seen commercials about toys again. nothing about what we see now days in T.V. shows men kissing men and marrying men. or women kissing women or getting married. this is 2023 and its what it is women love women and men love men. then there are the cross dressers. in which we had seen on T.V the show called oh shoot cannot remember the show that we know what show that was. the one guy dressed as a woman to get out of the service. today’s society needs to wake up and see the world we live in. there are lesbians, there are gays and there is cross dressers.


    2. I have yet to see a drag show that shows genitals. They lip sync to music mimicking the original performer. If that is a problem they you should also start pushing laws against the original performer.

      There are already laws against showing genitals to children. Just enforce those. You don’t need new ones. And yes I agree with those regardless if you are a drag queen or a priest.

      This is just red herring issue used to incite hatred.


      1. lip singeing a song that belongs to a ordinal singer should be illegal. but the law does nothing about it. for showing kids the parts a, a man or woman is not right they will learn that in school when the time is right and have a written permission slip for mom and dad to sign. i have seen a drag queen show on T.V but not in person. hatred is all over the place and needs to stop hating people for what color, what they wear, and everything else . we are human just like every one else is. if we dress up in female cloths so what keep walking.


      2. Why have children at a drag queen show? I saw one that actually lifted his dress up in front of children in the audience – why? Not Kosher at all! There are men kissing men on commercials – didn’t see the one shown presently? Why? To make all things mainstream – so that children will accept everything while they are young and impressionable. This is a form of brainwashing. Drag queens are fine, cross dressing is great, but please, please leave out these children – let them be children – they will learn everything when they get older, just like we learned about sex education in 7th grade, not kindergarten! My grandchild is 9 and he cries out one day, out of the blue, “I ain’t gay!” My son has smartly put parent guards on his and all of his children’s viewing of certain sites, especially You Tube. Gay is fine, but these kids are too young to understand and we should not be rushing their brains ahead of schedule and we need to allow them their innocence until they are mature enough to learn sexual and gender adult themes and activities.


      3. Why is a man kissing a man any worse than a man kissing a woman?

        Your grandchild may not be gay but other kids may be. Or other kids may have 2 dads or 2 moms. Shouldn’t they be allowed to feel normal? Is it really that hard or detrimental to tell a kid that sometimes a boy loves another boy or a girl loves another girl?

        That is not brain washing it is simply the dynamics of the real world. We had a lesbian couple living next door when my kids where little. They saw them holding hands and kissing like other parents. My kids didn’t think anything of it and it did not destroy them nor did they become gay. They were simply their friend’s parents.

        I don’t agree with a drag queen lifting their skirt and I did see it. But is it really worse than this at a family event?:

        Or this:

        Or the violence regularly in video games and movies?

        Again we are isolating drag shows simply because it is not the 1950’s norm. You can’t just pick out one bad event and condemn them all.

        I knew I was a girl since I was 4. I knew I had to hide it. From about 7 on every night I hoped that I would die before I woke because I was a freak and everyone hated me. That changed in my late 30’s when I started hormones. I still struggle with that from time to time. Many kids are just like me but end up not making it until they are adults.

        Isn’t it better to teach your kids and grandkids from a young age that others may not be like them but you still need to treat them respect and maybe even be their friends? It may be uncomfortable for you but it may just save a kid’s life. You can easily teach these things without teaching anything about sex.

        If we teach kids this then eventually it will not be any different than having red hair or being left handed or having a physical disability or being autistic.

        If we teach kids to be understanding of all people then who knows we may end up with a better world than the one we grew up in.

        P.S. I suspect you are going to throw out that if we accept this then some kids will think they are transgender when they are not. And yes that does happen but detransitioning is extremely rare. It is just another red herring.


  6. Hannah, you post so much, and so frequently, that I just can’t keep up with it all. But the title of this one really caught my eye. And, as Jodi has pointed out, there’s a lot to unpack.
    I completely agree with your main point: that in some relationships the yearning to dress leads to violation of what should be agreed boundaries about it. My own view is that a boundary isn’t a one-way thing: it needs to suit both parties. I tried to negotiate boundaries with my ex-wife, but they were way too strict: never talk about it, only do it at home, alone, with the curtains drawn and the blinds down. No contact with other people who do it. There was no recognition from her that living like that was impossible for me, although I gave it my best. But getting all glammed up, and then sitting at home alone made me feel like the loneliest freak in the world. It ultimately proved impossible to draw a line which was _just_ enough for me, and not _quite_ too much for her.
    But what drew me here was the phenomenon of guilt, and for me the guilt was overwhelming for years. I was brought up to believe that boys should act–and feel–in certain ways, and that if I did act (and try to feel) those ways, I would feel better in myself. My (Catholic) upbringing was by kind and loving parents, who really wanted what was best for me, without knowing what was really going on, and without knowing how else to handle it. So I tried to do what they said. But then at school (a boys’ school!) those gender roles were solidly reinforced, and I learned to keep a really tight lid on my fem feelings and inclinations–which have been there for as long as I can remember, and which have never gone away.
    As an adult, dressing has provided enormous fulfilment, especially as I’ve had a bit of practice now and my look is beginning to work better. But from time to time I look at myself (or a picture of myself) and feel that cringe of guilt. Of course that comes from internalised transphobia, but it’s basically lifelong, and probably cannot be completely eliminated.
    I can intellectualise it, and recognise that those mocking internal voices which say “Look at the state of you! What do you look like?!” are relics of another century, and another country. But I cannot simply wish them away, no matter how I try.
    Having more of a Vivienne social life (which has skyrocketed lately) has made an enormous difference to my self-esteem. And perhaps those voices will eventually fall silent; meanwhile I am doing my best to drown them out!

    Liked by 1 person

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