The Lying, the What-Ifs, and the Wardrobe

I remember the first pair of panties I had.  When I wasn’t wearing them I kept them hidden in a drawer.  I was fifteen.  I was terrified someone would find them.


Paranoia is often crippling but it can save our lives.  It holds us back from stepping out en femme.  What if someone sees us?  What if we run into someone we know?  We replay these scenarios over and over and over to the point where we become so frightened that it becomes easier to deny this side of us than to live with the anxiety that the endless “what ifs” bring.  
For some, the anxiety of living a denied life becomes greater than any risk that this side of us brings.  We accept that whatever happens, happens.  We dress, we drive to the mall, and…  no one cares.  It is this moment that the next part of our lives begin.


Of course, the paranoia we had becomes useful, in a way.  We likely replayed scenario after scenario of what we would do if we saw someone we knew.  Although we have stepped out of the house, we don’t let go of the thoughts that held us back for so long.  We look around everywhere we go, we avoid places that our friends, families, coworkers shop, we scan every store to see who is in there as we wander around in it.


We’re still living a secret life, but it’s also as public as it gets.


The more we do, the more we venture out, the more possible scenarios play out in our heads.  Despite how long and how often I’ve been going out, I still think about the “what ifs”.  Last summer I did a photo shoot where I stood on top of a narrow ledge next to a building.  I couldn’t help but think that were I to tumble to the ground… well, what then?  I pictured an ambulance, I wondered how I would explain to my friends that I fell because it’s hard to balance in stilettos on top of a wall.  Luckily I lived (and captured a few great pictures) and my worrying, my paranoia, was for nothing.


When I was fifteen and when I wore my panties I was as nervous as I could be that someone would see the lacy detail poking out of the top of my jeans.  When I wasn’t wearing them I was scared to death my mom would find them.  Basically I was a wreck all the time.  But this is a good example of choosing to live with the fear of being caught as opposed to the stress that denying who I am brings.


When I was nineteen I had my first apartment.  The panties tucked away in my dresser continued to multiply…  but so did my anxiety.  My girlfriend had a key to my apartment so I traded the fear of my mom finding out with the fear of my girlfriend finding out.  


Eventually we broke up but panties, bras, stockings, continued to have a place in my dresser.  Of course, my lingerie soon took up more room than my boy clothes and I soon had to get a storage bin.  And a second one.  When I was in my twenties I rented a room in my friend’s house.  I had my storage bins in my closet, behind other boxes.  It was unlikely he would find my collection, but still, the paranoia was there.


I had spent so much money over the years buying lingerie, purging, and then buying new lingerie.  I was tired of that.  I was tired of tossing out beautiful bras and panties.  I was tired of pretending that I could stop.  Acceptance leads to more “what ifs”, however.  Just as our thought process starts with “what if I see someone I know” to “what if they see me and tells everyone about me” to “what if everyone in my life thinks I’m a freak”, my thought process started to turn to “what will happen were I to die and my family found my lingerie and heels while they were attending to my belongings?”.


It’s not a comfortable topic and it sounds a little morbid but many of us think about what our family will think were they to find out about this side of us after we die.


On one hand (and I don’t mean to be glib or talk lightly of something so serious) some of us likely aren’t concerned about what people think of us now or what they may think of us after we have left this world.  I feel that way to a certain extent when it comes to some people in my life.  But for others I feel a little guilt that such an important part of me is a secret from some of the people I care about the most.  I would feel….  a lot of things were I to find out about something along these lines about one of my best friends and how they felt they couldn’t tell me about it.


As I let the “what ifs” play in my head, I usually wondered how I would explain something that really couldn’t be explained.  It can’t be summarized quickly, every t-girl and crossdresser is different when it comes to this side of us.  It can take countless conversations over the course of years for someone else to “get it” or at least come to terms with it.  Having an opportunity to answer questions, to talk about our feelings, our lives, can help someone, well maybe not understand this part of us, but perhaps helps make it a little easier to ease someone’s mind.  


But when we pass on, our family may find a beautiful wardrobe…  and a lot of unanswered questions.


If I am going to come out to some, I want to do it on my terms.  I want to portray who I am HOW I am.  If you come out as a crossdresser to someone and they google that same word…  well, they may get the wrong idea about who we are.  At least when I am alive I likely have an opportunity to talk about what crossdressing means to me.  But when I am gone unless Ouija boards work, then people will make assumptions without knowing this side of me.  


When someone finds out about this part of us, it will impact them, to put it lightly.  They may feel hurt that we kept a secret, they may be confused, they may be angry., they may feel obligated to continue to keep our secret.  When we come out to someone, it turns their world inside out.  When our world does this, regardless of why, we usually need to talk to someone, and it’s easiest to talk to someone that understands, someone who went through what we are going through.  But finding out our husband/son/brother/friend is a crossdresser isn’t something that most people don’t talk about.  With no one to talk to, we become lonely, frustrated, confused.  


I knew this could happen were I to pass away.  As complicated as my relationship is with my family (both before and after I came out to them), there is, and has always been, love there.  I didn’t want them to feel alone.  I wanted to, as best as I could, explain who I am… FROM BEYOND THE GRAVE.  Again, I don’t mean to be disrespectful, but I am trying to keep this as light as I can.  So, I did the only thing I could think of.  I wrote a letter.


Perched atop panties, bras, garter belts, stockings, was an envelope.  Inside was a note where I acknowledged that finding these clothes was likely a shock.  I apologized for adding to what was likely already a stressful and emotional time.  Dealing with a family member’s passing is difficult (to put it lightly) but discovering a secret just adds to it.  I wrote, as best as I was able, about this side of me.  I provided a few websites where my family could turn to, such as PFLAG, if they needed someone to talk to.  I did this as sincerely as possible.  It wasn’t an easy letter to write, but I knew I had to do it.  I didn’t want them to feel I was keeping a secret from them, but really, that’s exactly what I was doing.  I didn’t want them to think I was lying about who I was, either.  Even on death, I wanted to come out on my own terms.


I tossed the letter, along with my lingerie, on my next, and what would be my final purge.
I still think about the “what ifs”.  But that’s just who I am, even outside of this side of me.  As I get older I think more about the future and making plans.  Plans for retirement, plans for my passing. 


I have quite a collection of books.  I also have a friend who shares the same passion for reading and books as I do.  I told him that when I pass, I need him to take care of my book collection.  It’s a huge collection and it’s not something I want to burden my wife with after I die.  I have similar requests of others in my life, such as my finances.  


I can have all the contingency plans (if you will) that you can imagine, but if I die suddenly I know my wife is going to inherit a huge wardrobe.  My wife and I have very few similar tastes when it comes to clothes and she’s going to need an evening gown or a PVC dress so it’s not like her wardrobe is going to expand in a way that she’ll necessarily benefit from.  I do wonder what will happen to…  everything.  I suppose the easiest thing would be for her to simply donate what could be donated.  I’m sure some nonprofit charity would be thrilled to receive a leather minidress.


As old as I feel these days (mentally, that is) I am not ready to make any decisions of course.  But again, we can’t stop thinking about the “what ifs”.

Love, Hannah

Related reading

Sharing the Secret

Identity and Responsibility

Meeting Your Heroes

Let it Go

14 thoughts on “The Lying, the What-Ifs, and the Wardrobe

  1. you tell this so well, as if you were in my mind. Thank you so much . you are so helpful and such a wonderful person. please keep up the site. and God bless you

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  2. I have been living the paranoia for some time. My wife is aware and she is very supportive and I wear whatever I want around the house and don’t own any “male” undergarments. I own one pair of jeans that are not women’s and I rarely choose them when dressing for work each day and I wear jeans on an almost daily basis. If I do not wear jeans my khakis are womens from Banana Republic and American Eagle. I spend all Summer in the wonderful short, shorts with a built in panty and nobody bats an eye (although they comment on my smooth legs). I have a drawer, in the bathroom vanity, that was previously nearly empty only holding deodorant and maybe a can of some sort of body spray that came in one of those Christmas gift sets we all receive each year. I sorted and cleaned that drawer last week because it was starting to get hard to find anything. It was hard to find the concealer I was looking for or my brow brush was buried. I rarely leave the house without makeup applied as I feel to plain without it to be seen in public. I always say I don’t go out dressed but, the reality is I go out dressed in clothing that came from the women’s side of the store every day. I have not stepped out in any of my beautiful dresses, skirts or heels. I spend all Summer in the wonderful shorts with a built in panty and nobody bats an eye (although they comment on my smooth legs).

    There have been a couple of events that have happened over the last few weeks that have started chipping away at my paranoia. I had not been out to shop other than thrift stores for quite some time but the wife and I made a couple trips to get Christmas gifts for the family. We went into Ulta to get some items for my daughters and this was the first place it happened. We approached the counter and the teller asked, “Did you ladies find everything”. I am sure the teller asks this of everyone but, I believe this was a life changing event for me. This actually happened several times over the course of these trips and when I was alone at one department store the cashier called me Ma’am several times. My wife when we were at a wedding for some close friends actually referred to me as “She” several times and then corrected herself as fearing she had outed me.

    I think this was a break that has quelled some of my dysphoria replacing it with euphoria. That euphoria is almost like a drug as the feeling cannot be explained. My hair has grown down to where it lays on my shoulders and it is very curly and I spend way too much time making sure it is perfect every day and I believe this was a contributing factor as I make sure when it is cut the person knows I prefer to keep it long and to cut it just like they would for any of their other female clients.

    Thank you Hannah for what you do! It has been things you have posted that have made it easier for me to move forward with embracing who I am. You made it easier to set and talk with my wife about things and that has led to sharing a lot of feelings that were bottled up for a LONG time. Sorry to be so long but, I felt that I needed to share this. A question with five words changed my life in a significant way and I can only hope others find the same.

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  3. I loved the blog along with the whimsical title. By the way, I have written a collection of Narnia themed short stories.. Would you care to read them?

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  4. I’ve been on that emotional roller coaster for most of my life. I feared that somehow my desire to wear feminine things some how showed through, even when I wasn’t wearing panties or stockings. I did stashed items discovered a few times. Mom said nothing, but the items disappeared. My wife was initially suspicious of whose panties they were, and seemingly relieved when I admitted they were mine. And I went through those cyclic purges, periods of repression and denial…still do to some extent, but at least i’ve grown past throwing things out or donating my wardrobe.

    At this point, I haven’t quite decided how to handle what I might leave behind.

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  5. In reading through your post today, Hannah, I was reminded time and time again of some lyrics from the musical Hamilton. Not exactly sure on the song title but the specific ones are “ Who lives, who dies, who tells your story?”

    I think it is only natural as people that we think about what will be told about us once we have finished things here. I suspect that every person has their own fears of what secrets might be revealed once they pass on and others take a look at their life without any sort of context.

    In the end, the best I or anyone else can do is to be the person we want to be, however the gaze of hindsight might pass its judgement down.
    Many less prescient thoughts come to my mind on this topic but I think it safest to curtail it here before I ramble on for hours or days.

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    1. Totally agree Elise, once I’ve departed this world I can’t imagine that my ‘hobby’ if discovered will make the tiniest blip on anyone’s radar. And at that point I won’t care. I’ve set up a will and a trust for anything of value I leave behind. No, my extensive collection of female accoutrements are not included despite the large sum of $$ they represent .

      Great piece Hannah. You do bring up excellent points as always. The letter idea intrigued me, but I know myself and it will not happen. My wife and I are very close in size, but she has zero interest in donning my wigs, dresses, and certainly not my heels -lol

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  6. I had to finally tell the person who will handle my affairs re: Emily as I felt she would have been extremely hurt to find out when I died.
    The other issue-getting caught–I had 2 very close calls with neighbors. It didn’t stop me because on a risk reward basis I was not about to ditch Emily

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  7. Very well written. You capture the thoughts, fears and feelings of many other cross dressers. I know for me, I got anxious just reading your post. It hit the nail on the head. I am now 71 and I’ve lived this roller coaster of fear, excitement, dread that you describe since my late teens. I’m married, I underdress daily, my wife knows, but she’s the only one and isn’t comfortable with my desire to wear women’s clothing and worries about someone seeing me in public. So, I continue to do what I’ve always done when I want to dress. . . I plan how to move the clothes from my closet, to the car and find myself changing in a parking lot away from prying eyes. For an hour or two each month, I’m free, I feel complete and I’m at peace with who I am. Then it’s back to the parking lot, change back to my drab self, and start to worry about how to get everything from the car back into it’s place in the closet undetected. Thanks for your eloquent words. . .

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  8. I love you Hannah. That was so thoughtful and well written. I have messaged you before and I have kept this secret as well. I have come out to no one. I have gone so far as to order online, have clothes delivered to a UPS store and drive it to an anonymous storage locker. All to have 3 or 4 opportunities a year to dress. All because I was told that this has no place in our marriage by my otherwise damn near perfect wife. I think that is the crux of our problem as crossdressers. It is brutal to be gender fluid or a crossdresser. One minute you feel fine in your male role and the next you feel like you NEED to put heels and a skirt on and well you know… You aren’t accepted or tolerated. You hurt no one, but we are threatening. We shatter images of normalcy and consistency that most need to remain comfortable and in control. And as much as I hoped my dressing would stop, it never does.

    But I stopped the storage, because what if something happened? I don’t want to go down with secrets anymore. So I am picking up what you are putting down in this post. I have decided to stop dressing until I can be courageous enough to come out to the world like you have and accept the consequences. When that happens, and it will, I don’t care what happens when I die. I have spent too much time bottled up and away from my true self to worry about what happens when I am gone. Like many, I have lost too much time. What society took away from me in life, let them deal with in death if need be.

    Your posts are sooo good. Thank You! You are special.

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  9. My fear of being found out stems from being discovered by my brother when I was 13. I was standing in front of my mother’s closet, naked, holding one of my mother’s skirts. He laughed and laughed and told our sister. For the next year, they both would address me as “little fruitcake”. Then, after a year, they just stopped. Neither of them ever mentioned it again. That was 40 years ago. I am so motivated to talk to my sister about this but it’s hard to say it after all these years.
    On a lighter note, I came out to one of my co-workers recently. I complimented her on her skirt, recognizing the specific designer as it is one of my favorites. She asked “how do you know about that?” I said “because I like skirts!” She went in to say she picked her outfit that day because she was “sick of wearing pants”, I agreed. “ Like I said, I like skirts!” I’ve known her for years and I’ve always known she wouldn’t judge me. She is gay and a chaplain, probably the least judgmental person I have ever met. She understands the pain of being closeted.
    Someday I will talk to my sister about this and thank her for her closet of pretty clothes that got me through my teen years.

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  10. Again I must say “thank you” for bringing up a major issue at a time when anyone my age may pick up virus de jure, and be gone before all the vast infrastructure of feminine gear may be dealt with. I think of it and worry every day, even though I

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  11. even though I’ve left plenty of breadcrumbs to lead where my values and props have been . I long ago wrote a statement about why I think some of it happened; it’s a short story about physiological, psychological, social , and even a World war when I happened to be born before it ended, and was raised by women on the home front. I’m good at it like yourself, and your recent blog about comfort, refuge, self compassion, not narcissism. is pretty close to home, and the rest just innocent habits that help us survive in a rough world. Some day I’ll share that final explanation with the wonderful brothers and sisters drawn to responding to your wonderful blog. I salute you for your serious, and still light openness to truth and fun, and lighting our way to free expression and self acceptance. I particularly like your emphasis on our responsibilities to others as we are being our sweet selves.

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