Let’s Talk About the Internet

I’ve written before how the very first word I ever searched online was “crossdresser”.

And like Pandora opening that box, this unleashed a combination of horror and hope.

Although technology has evolved at an alarming pace since 1994, people themselves haven’t changed much.

My first real introduction to the seemingly predominate nature of crossdressing suggested that THIS is very much a sexual thing. A fetish. Fast forward to 2022 this still seems to be the case. Googling “crossdresser” mostly provides one with options to date or hookup with someone who crossdresses.

Is it any wonder that the prevailing public perspective and interpretation of a masculine presenting person who wears femme clothes is that this is a kink? A turn on?

The internet is, not to sound too cliched, is a blessing and a curse.

Trying to explain who we are and why we are is hard enough. Google results usually requires us to also explain who we are not. It’s like… unlearning something before we learn how to the same thing the correct way.

When we come out to someone, it’s normal if that person turns to the internet to get some clarification, some perspective, some answers, and some information about this side of us. We might cringe a little at this, we may even dread the person we’ve come out to jumping online for resources or support.

Because we KNOW what they will find. And we know because we’ve likely searched the same terms that they themselves will type into a search engine.

Now, I want to make it clear that if THIS is indeed a fetish for you, you go girl. I am not here to kink shame. I promise. If this is a sexual thing for you then you are probably delighted with what someone can find online.

If this isn’t a kink for you, then I can relate. Combing through Google results to find resources and support is not unlike looking desperately for a size 13 stiletto. You know it’s PROBABLY somewhere out there but goodness the search is taking FOREVER.

This is one of the reasons the web could be perceived as a curse.

Of course, “curse” is probably too strong of a word, but I digress.

And! It’s not REALLY the internet’s fault. Search results are based on algorithms which are, presumably, determined by human behavior. I don’t know, I am not a computer person. I suppose one could argue it’s not the internet itself that provides an uneven portrayal of a crossdresser but instead it’s the people using the internet. If the prevailing opinion, regardless of it’s accuracy or inaccuracy, is that crossdressing equals a fetish then it’s people’s opinions and perceptions of us that might need to change.


As the story goes, Pandora opens the box and after all the horrors have left and have spread across the world, there remains a glimmer of hope.

The hope for someone like us, the comfort for someone like us, is the realization that we are not alone. We never were. It’s the reassurance that we are not the only masculine presenting people that woke up in a nightie or wear panties under our work clothes.

How wonderful is that?? I can vividly recall the feeling I had when I first heard the word “crossdresser”. To know that there others like myself. To learn that there were so many of us that there was a word for people like me.

Few things in this world are purely good. Like yin and yang, there’s a little bad in every good thing. And the opposite is (sometimes) true, too. We take the good and the bad. Some things, for lack of a better phrase, come with the territory. On one hand it’s nice being able to listen to music and stay in contact with friends and look up information and shop for a new dress all from the convenience of a smart phone… BUT it also increases the expectations that our angry, unstable boss can reach us 24/7.

I hate my boss at the moment in case you couldn’t tell, lol.

You could call technology a necessary evil and it wouldn’t be hard to disagree. Technology has an impact on everything.

And yes! Even crossdressing.

If you are of a certain age then you probably remember building up courage, likely for years, before you braved walking through the lingerie section of a store. The insane, insurmountable amount of sheer will it took to quickly and discreetly slip on a high heel and praying it fit without having a salesclerk walk by and notice what this dude was up to.

And of course all the times we trembled and shook with fear when we actually brought a dress, a pair of panties, to the cashier to actually buy them.

(There’s also the crushing disappointment we usually felt when we take our treasures home to realize that something doesn’t fit and how we have to weigh returning it for a refund or just accepting that we essentially just wasted our hard-earned money.)

Technology has changed how we crossdress. The idea that I can just go online anywhere and order a dress is nothing short of mind-blowing to 18 year old me. I’ve shopped for panties while waiting to board a plane. I’ve picked out stilettos from my couch. A few days later… ta-da! They arrive! And! If they don’t fit, it’s back to Amazon they go. No awkward small talk with a cashier, no fear of a friend seeing us in the dress department of Target.


But it’s not all shopping. There are makeup tutorials, information about the overwhelming world of different types of wigs…

Of course, there are also a lot of resources that offer support and can connect us with others like ourselves… and I am not referring to “date a crossdresser” websites. No, there are some wonderful forums out there and a lot of amazing t-girls with personal websites that remind us that we are not alone.

Although in many ways the internet removes the risk of shopping for lingerie without the fear of, well, shopping for lingerie brings, it can also out us in new and creative and terrifying ways.

Recently some very strong gusts of wind blew over a tree in our backyard. I was telling a friend about it and showed her a picture of it. While she was looking at my phone I just prayed to God I didn’t get a Twitter notification that “Luv2Crossdress69” liked my photo.

Disclaimer, I have no idea if Luv2Crossdress69 is a real account or not.

In simpler times I only had to worry if someone saw my bra strap under my dress shirt. How things have changed. Now I have to think about my stupid phone outing me.

There’s also the risk that having a femme social media account brings. Hannah used to have an Instagram page. My wife still has one. Although my wife never looked at Hannah’s page, and Hannah never looked at my wife’s page, one day Instagram suggested we follow each other.

And of course, that led to the fear that this suggestion might spread to others in my wife’s orbit who might discover me.

So, I deleted Hannah’s Instagram account. I feel I am very cautious (to the extent one can be) of who has an account on different platforms. My wife is on Facebook but not Twitter. Hannah has a Twitter account but not Facebook.

Is this completely foolproof? Probably not. I am not a paranoid conspiracy theorist but I don’t put much faith or trust in privacy when it comes to being online. Same with technology. When I purchased my iPhone I also had to accept that Apple was going to know where I was 24/7 and was going to know everything about me and everything about Hannah.

If we’ve learned anything over the last thirty years is that things might change but mostly they stay the same. Although I don’t have to shop for an outfit in public if I want the (thinly veiled) anonymity that the internet provides, the internet also creates new and different risks that this side of us can brings.

Love, Hannah

4 thoughts on “Let’s Talk About the Internet

  1. You are correct about the way the Internet can expose us and this is getting worse as it seems that our current government in DC wants to regulate our actions 24/7, including financial activities, which they have no business doing either of these as these are violations of our privacy.
    Cross dressing is done for different reasons. Sexual turn on is one, but this can be combined with other reasons: wanting to see what we look like in feminine mode, wanting to wear pretty and sexy clothing, a feeling of relaxation when stressed, a general good feeling of being seen, by ourselves and maybe others, as a woman and hence feeling and looking like the opposite sex. I believe there are a lot more guys who cross dress than we think there are – I wouldn’t be surprised if such actors as Tony Curtis, Jack Lemmon, Milton Berle, Adam Sandler, etc., cross dress(ed) in their private lives!


  2. absolutely correct on that issue. cross dressing has been around for years but never brought up. real woman now days cross dress as men and wear jeans and skirt, not a dress or skirt and blouse and make up. so why cannot men wear a dress it’s been around for years and mean years. it’s not about having sex with another cross dresser or getting Horney for whatever! it’s all about being feminine and looking pretty. the clothing is so much more comfortable to wear and feel great to wear. great post thanks for sharing


  3. Yes, second time in two articles that your boss has come up. Sorry that he is being an angry dick at the moment! I have been bossed and and been a boss for most of my working life. I abhor that paternalistic/authoritarian version of leadership. It hurts people and impedes progress.

    Ok, to the topic. Isn’t it funny. Crossdresser was pretty much the first term I searched for as well! It just goes to show that our curiosity existed before this particular medium came into existence.

    I eventually an online community that I have followed for many years, and honestly, it has been a kind of lifeline for me. However, I have dropped Facebook and Twitter. I found them to be toxic swamps and frankly I was freaked out by Facebook managing to suggest connections with people I knew in real life. I’m willing to take very few chances with my identity for convenience.

    As for the public perception of cross dressers that might be created by the internet, I think its a matter of confirmation bias. The internet reinforces beliefs and prejudices that are so pervasive in Western culture, especially in the US. As a culture, everything is sexualized…mostly for marketing purposes…because sex sells. Porn makes up 90% of the internet. Evidently thats what people search for most often. So, its not surprising that the majority of internet sites sexualize cross dressing.


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