Straight Crossdressers

Do you ever ask for clarification when you are asked a question and even though you are pretty certain you know what they mean but you are annoyed by the query?

I do sometimes. And yes, this is VERY passive aggressive of me.

I’ve written before how shocked (and yes, looking back this was a very naive reaction) I was when I learned that crossdressing was very sexual for some people. I honestly didn’t see the correlation between sex and crossdressing. Once I learned that it was, I started to see the pattern of how this side of us was portrayed in media. A person assigned male at birth who liked dresses and panties was almost always showed as a pervert or gay or confused or a fool.

Of course, there is nothing wrong with this side of one being arousing to them. I am not kink shaming anyone. Promise. But I was amazed and dismayed at how overwhelmingly sexual crossdressing was thought of, and portrayed as, in movies and other forms of entertainment.

I suppose we are all annoyed and defensive about how our passions and interests and lifestyles are stereotyped. It’s not unlike a football player being portrayed as a brainless idiot in a movie when in reality most athletes are quite intelligent in real life.

Anyway, my annoyance and confusion about a “man wearing lingerie is connected to sex” grew with each time I came out to someone, particularly girls I was in relationships with.

And yes, I know that lingerie is almost always associated with sexy time but I wore (and still do) wear lingerie when I want to wear something beautiful.

Coming out to someone always included discussion of sexual identity, such as whether or not I was bi or in denial about being gay. This is an example of what I mean about a question that I was/am annoyed by when I am certain I know what they mean.

Essentially I don’t see the connection or correlation between clothes and sexual preference. Yes, I wear lingerie and yes most people who wear lingerie are girls and yes many girls are sexually attracted to men so I do understand the association of lingerie with being intimate with a man.

But dammit, lingerie doesn’t HAVE to be automatically associated with being railed by a man.

I knew what someone meant when sexual identity was brought up during “the talk” but since what I wore to bed had nothing to do with who I went to bed with, I was easily annoyed by the subject.

But it wasn’t their fault. The girls I came out to also were influenced by the media’s portrayal of crossdressing.

I think a lot of us feel defensive when it comes to our sexuality as crossdressers. Perhaps not defensive, but maybe wanting to be understood. Like, YES I love panties and NO I don’t want to have sex with men.

We want to get that clarification out of the way as soon as we can. Perhaps it’s an effort to prevent chasers from blowing up our inboxes.

My Twitter/X profile is hopefully pretty clear about who I am:

Of course, a social media bio is challenging to write. It’s tricky to summarize anyone in just a few words, particularly someone like us.

It’s not uncommon for a gender non-conforming person to state their sexual identity in a bio. Some of us identify as straight and that’s, well, it is what it is. I don’t think much about definitive labels on gender and sexual identity though I understand how important they are to some and I respect that.

But I suppose I get a little confused about “straight crossdressers”.

Let’s set that potentially explosive and divisive sentence aside for just a moment.

I refer to Hannah and my male identity as two separate people. Of course, that is the very definition of multiple personalities but it’s nothing so serious. It’s just easier, especially when it comes to talking to my wife about, well, anything.

If a package is delivered my wife will mention to me that Hannah received mail. If I have plans coming up I’ll tell my wife that Hannan is going out next Saturday. That’s really about it. It’s not like my wife can’t talk to Hannah about things that “the boy” usually handles.

Hannah has her own friends, email address, and wardrobe. Hannah is more social (but barely) and has her own personality. Again, this is not me being in denial or having an undiagnosed multiple personality disorder. Hannah’s personality and social behavior comes from the boy. It’s just easier and feels more natural for that aspect to come out when I am en femme. I am less inhibited and less self conscious so my guard is down.

Since Hannah has her own life, it’s not a stretch for someone to assume or at least ask if Hannah has her own sexual identity.

It’s a fair question, I suppose.

But I don’t think we change our sexual preferences when we are wearing certain clothes. Like I said earlier, I don’t see the connection between what I wear and who I want to sleep with it. I do know that some of us like being with men when we are en femme and some tell me that they are straight in their male lives but love sleeping with men when they are in girl mode.

I have my own perspective on that and I want to be clear that this is my own perspective.

But we can’t have things both ways. What I mean is that some of us feel that their dressing has nothing to do with their sexuality and some of us want to sleep with men when they are en femme.

It’s like… is dressing connected to sexual preference or not??

This is not an answerable question. It can be for an individual, but never for everyone. I make it pretty clear that this side of me has nothing to do with sex/kinkiness but I know for a lot of us there is very much a connection.

And that’s okay! Again, not kink shaming anyone. No one is here to change anyone else’s mind. I can’t type that “crossdressing isn’t sexual” when half of us are very much of the opinion that crossdressing IS sexual.

Stereotypes exist for a reason. They are rooted somewhere, usually unfairly and/or undeservedly. There is always going to be a dumb football player or a kinky crossdresser to “prove” that athletes are unintelligent and that boys who wear dresses are perverts.

Stigmas don’t fade away easily.

I suppose that my confusion comes from WHO is straight. Is it the person when they are in male mode or is it their femme persona?

As I mentioned earlier, it’s not a stretch to ask about Hannah’s sexual identity. Who is she attracted to?

The answer is that who she is attracted to is the same as who her male counterpart is: my wife.

So, does that make Hannah a lesbian? Sure, why not. Who cares.

Does this make my male self straight? Sure, why not. Who cares.

If either of us (US being Hannah and my male self) were to be asked about sexual preference and we HAD to answer, she would be gay and I would be straight.

Again, who cares. To me, someone’s sexual preference is about as interesting and about as relevant as someone’s favorite color.

Am I a straight crossdresser? Sure, I guess. When I am in male mode and wearing a nightgown or a femme shirt and leggings I suppose I am crossdressing. I am presenting as masculine (meaning I am not wearing my wig or makeup), I would use male pronouns but I am wearing “girl clothes”. So, I am crossdressing, as I define it. In this attire I am still very attracted to my wife.

If Hannah gets home from a day out, stilled dolled up, and my wife is looking really cute then I suppose that it reinforces Hannah’s sexual identify as a lesbian.

Even as I write this I can’t help but thinking OMG THIS IS SO STUPID AND WHO CARES.

Anyway, I think I’ve made my point.

But… I get it. I think when someone identifies as a straight crossdresser they are aware of the stereotype that a man who wears pretty clothes is attracted to other men. I mean, if I HAD to, I would, at least for part of my life, would also identify as a straight crossdresser.

However, I suppose it’s also possible for someone to identify as a straight crossdresser but are referring to HER sexual preference, therefore they prefer masculine identifying people when they are dressed.

It’s all very nuanced and it’s all very much different from person to person… often influenced by their gender identity and even their gender presentation.

I don’t mean to be dismissive or critical of someone’s sexual identity. I understand that it is sacred to a lot of people. I suppose this is all my perspective about how pointless sexuality and gender roles and societal norms can be. Once we start going down the rabbit hole and assign all sorts of conditions and qualifiers then it gets silly.

What I mean is that one would assume another’s sexual or gender identity is a fairly easy question to answer. But these questions, at least for me, have conditions. Am I straight? Sure. But what about Hannah? After all, I am her. Well, Hannah isn’t straight.

So am I/we bisexual? No. Neither of us (again, Hannah and my male persona) are attracted to men AND women.

Sexual identity is something that causes a lot of anxiety in some. Sure, you may be married but maybe you think a man is handsome, maybe kind of attractive. It doesn’t necessarily mean anything. It doesn’t mean you are gay or bi. It doesn’t mean you aren’t straight. It’s not like all of a sudden you are no longer attracted to women.

You never HAVE to deal with absolutes (which is in itself also an absolute but let’s ignore that). Perhaps I am trivializing sexual identity but I think of many things in metaphors. What I mean is that you can be the biggest, oh, I don’t know, New York Yankees fan BUT maybe you admit that the Chicago Cubs has a really good pitcher. This doesn’t mean you have changed your allegiance to a team. This doesn’t mean you don’t like the Yankees anymore. I can despise a band with ever fiber of my being but I can also admit if they have one good song. It doesn’t mean I hate them any less.

And even if the needle has ticked slightly on your sexuality, it’s not like you have to do anything about it. You don’t have to come out. It doesn’t mean you need to have a huge lifestyle change. Really, the only people who need to know about your sexuality is yourself and your partner.

Human beings are complex people but we have put self-imposed parameters on everything. We have to have a label and norms for everything. Girls have to wear pink, men can’t find another man attractive… it’s all very silly. We did this to ourselves.

Love, Hannah

15 thoughts on “Straight Crossdressers

  1. Thank you Hannah for this column. I was glad to learn that I’m not the only one with two different personalities or identities. My Morgan is so much different than Mike and Morgan definitely identities sexually as a woman.
    I had a brief time when I was young where I did wear my mother’s panties for sexual gratification but now as Morgan I wear woman’s lingerie just because I feel that I belong in them. Yes people do make assumptions of us and the problem is we can’t show them what we are really feeling inside.

    Thanks again.
    Morgan

    Liked by 1 person

  2. Great post, these are questions my girlfriend who supports my dressing constantly battles with, “Is she enough for me” “am I really wanting to be a woman 24/7” we have great discussions, but still she wonders if I need more to be happy.

    Liked by 1 person

    1. My wife’s big question at this point in our 35 years together seems to be whether she’s enough for me without the dressing up as well.. I’m trying to be more aware of this and ensure that she knows that she is.
      She also encourages and supports my lifestyle and we dress and play together. Our sexy times. I’m beginning to understand though, that this is my thing. Even though we always have a great time. I need to come out of my pink fog sometimes and indulge her fantasies and kinks as well.

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  3. Excellent post Hannah!
    This one’s right up my alley. Lol
    Recently I began to dress up around the house more often than just our ‘sexy times’. This also raised questions with my wife who supports and encourages my lifestyle. How far did I want to go with this? Did I want to open the closet door? Did I want to go out in public?
    I don’t exactly know the why my love of lingerie started when I was about 10 years old. Still working on figuring that out if at all possible. lol I do know that dressing up made me feel great and somehow empowered. I was also very scared of getting caught sneaking around in the closet in the early days. This would have definitely not been understood in my household.
    Though I had a couple of gay experiences in high school I always knew I was a guy who liked pussy and dressing in lingerie.
    I have occasionally worn lingerie under my clothes while out and about but I don’t usually have the same good feelings because I’m nervous about hiding it and usually uncomfortable. lol A good portion of my 40 plus year career involves outdoor construction. Ever tried to were lingerie while you’re shovelling or using a wheelbarrow all day. Not much fun! lol So for me home is where the heels are.
    I fully enjoy being a guy when I’m in public and am comfortable with who I am. I also love coming home to my wardrobe and slipping into something that makes me feel great inside and out.
    Different strokes for different folks as they say. As long as your not hurting anyone unless that’s what you enjoy. lol Who gives a fuck why you do what you do or what label you are assigned. 😻

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  4. I should have said Bi experiences instead of gay. A small brain fart by me. If I offended anyone please forgive me. It’s only words. And words are all I have. To help you understand me. 😻

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  5. Hi Hannah,

    Thank you for generating this discussion. Aside from those who cross dress, sexuality for many people does not neatly fit into a box. Even those who consider themselves heterosexual can have a broad menu of what they enjoy doing sexually which by societies standards, out in the open, is seen as taboo, yet many indulge in behind closed doors. I personally see labels as a way for the outside world to try and make sense of it all much like the topics of religion, life beyond our planet, and paranormal activity. Why can’t God, Extraterrestrials, Evolution, the Spirit World, and Big Foot all be possible simultaneously? Because it would hurt our tiny little human brains and upset the security of linear thinking in Society. The herd mentality and the fear of not conforming to societies standards is what keeps many from being open about who we are and how we feel.

    At the end of the day, it is who we love and choose to be with that brings label free joy to out lives. Experimentation alone does not define a person, tendency, or sexual label.

    Look at our society and what is happening in the world today. Does the opinion of others truly matter? Goes back to the earlier blog about whether we need approval or are seeking approval in out lives. We have one life. Important to be true to ourselves.

    Nadine

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  6. This topic was so thought provoking I had to comment twice. Touching on the idea that we are somehow more than one person, I personally view myself as one God given individual that has different parts of my life. Whether I am wearing a skirt and heels in the privacy of my own home, or sitting at a Twins game in jeans and a T-shirt drinking a beer (incidentally, the Astros lost last night to the Rangers – Yes!), I am still one individual. Though I may have many facets to who I am, I am still one person. How that translates to our personal relationships is a broader discussion, but still consider myself one complete whole individual. Consider this. Perhaps if we could decide on representing ourselves as one person, many of us might choose the En Femme presentation. For some, representing ourselves as Male in how we dress could simply be viewed as what we need to do to survive. Not saying this is true for all, however, might explain the very nature of how many of us live our lives. Maybe part of our responsibility in selectively sharing who we are to change the narrative is to talk more about what we like. Baseball, gardening, politics, theater, foods, entertainment, golf, bowling, hunting. If we limit ourselves to only focusing on our clothes and what we look like, nobody will get the chance to really get to know us and how much we are alike, with maybe the exception of the panties we wear.

    Nadine

    Nadine

    Liked by 1 person

  7. But Hannah, you promote your wish list on your X profile. If sex is such a surprise, who do you think is sending you things off the list and why? Unless you have vacuum bags and coat hangers on that list, this article seems a little phony.

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    1. The connection between sex and dressing used to be a surprise to me, but these days I expect others to make the association.

      People send gifts for various reasons. Some just want to do something nice. I make it clear that they shouldn’t expect any private photos or other… “access” to me. From my perspective, a gift is freely given without any expectation of anything in exchange,

      Love, Hannah

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      1. Except maybe a thank you?
        Gifts also need to be accepted with some degree of gratitude and appreciation or it’s rude to the sender. I would think there’s many reasons that people send gifts. Not just sexual. Although I’m sure that’s a big part of it. Some may just be appreciative of the help that she offers and just want to do something nice. Maybe have a little faith that there’s people out there who just want to so something kind. Do you need any dish soap or laundry detergent Hannah? Lol
        If people want to send gifts you might as well ask for what you want. Don’t you think? I believe I detect a note of jealousy there anonymous? Would you also like some vacuum bags and coat hangers? Or maybe just ask for what you want. 😻
        🚘 🏍 🚲 🛴 🛹 🛼

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      2. I have no doubt that you would says thanks. I just thought people should know that a simple thank you is all that’s necessary when you receive a gift. 😼

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  8. My takeaway from the article is Hannah acknowledging that there are some of us that do have a sexual connection to what we wear and some do not. Historically, many assumed the former applied to all of us. There is no right or wrong answer. All of us have had different experiences and even those experiences, or preferences don’t pigeon hole any of us to a label. Many assumptions are made by those that might not have the same experience. For instance, if a man sleeps with another man, that does not automatically make him gay. There are some gay individuals that think Bisexuality is a denial of being gay. There are gay men that are convinced that if a straight man were to have a same sex experience he would see the light and confirm that all men are secretly gay inside, they just don’t know it! All a bunch of rubbish. Live and let live. I don’t really care who anyone is banging or why. All of this is fluid. Some individuals can change there sexual preferences throughout their lives.

    Nadine

    Liked by 1 person

  9. Interesting and thought provoking article, including the comments. I am a heterosexual man and am more than happy with my gender. I am comfortable and happy with my normal male clothing on a daily basis and never feel the need to dress differently. That being said, I love wearing lingerie! I feel great when I dress up, achieving a sense of confidence and feeling sexy far beyond how I feel without lingerie.

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