Her Journey

If there’s anything I’ve learned after over ten years of blogging (do they still call it that anymore??) about crossdressing/transfeminity it’s that we all have so much in common. Most of us “got started” very young when we became enamored with anything from pretty dresses to lingerie to makeup. Many of us didn’t feel quite right doing “boy things” or bristled at the idea of BOY clothes or GIRL clothes.

We have shared experiences when it comes to what makes us happy. The joy of wearing panties for the first time. The excitement of finding heels that fit. The exhilaration of our reflections after our first makeover. The feeling of conquering all fears when we step out of the house en femme for the first time… or the thousandth.

We have also felt less desirable emotions. The crushing dysphoria when we don’t look as cute as we would like. Feeling we are “too male” to be pretty. The shame we are told to feel when we do or wear anything that is considered feminine.

Buuuut something we don’t talk about much is the… well, bad things that some of us do.

And I am not innocent by any means.

When I look back at the early years of when my wife and I were both discovering the depth of my gender identity I made a lot of decisions that were selfish and not completely thought through. I may have been lost in the Pink Fog or affected by a different kind of fog but the point is that I wasn’t always making the right choices.

What do I mean? Back then I spoke endlessly about clothes and makeup. All of THIS was overwhelming as it was but I didn’t pick up, or I ignored my wife’s cues when she needed a break from her husband babbling about high heels. I kept suggesting she and I go out dressed despite her telling me that she wasn’t ready for that.

I felt a little powerless when it came to the hold that my femme side had on me. It was overwhelming for my wife but it was also overwhelming for me as well. All of these desires and longings came rushing out, like a dam breaking and I just couldn’t find the balance of how THIS would fit into my life, my marriage.

This side of is complicated and multi-faceted and touches on all aspects of our lives and it’s easy to connect the dots as to how this revelation (not only to our partners but to ourselves as well) impacts EVERYTHING.

Having any sort of non-cisgender identity is hard enough as it is for our partners but we often put them through stress and fears as we try to navigate these strange new waters. My wife wondered (to say the least) if I was going to transition. Despite me telling her otherwise it was hard for her to believe this at the rate I was going. Discovering who you are is a journey but from her perspective this part of my journey wasn’t a slow, steady wandering… it was going a million miles an hour.

Nothing I said or did eased her concerns or fears. It took time. It took conversation. It required me to stop drinking. It took counseling. It took self-reflection. I “calmed down” over time. I made friends with other t-girls and found support, even if it was just a friend to go shoe shopping with. I LISTENED to my wife. And I committed to doing the things that she needed from her partner, her husband… from Hannah.

Accepting your own gender identity isn’t necessarily easy. Marriage takes effort. Both of these things together?? Buckle up.

I am fortunate she stuck by me. After all, THIS wasn’t what she signed up for. I think some people are afraid of what would happen if their partner had an affair… but not many people speculate on what their life would be impacted by their partner coming out as anything other than cis of straight.

Earlier this year I wrote the longest article in the history of the internet (obviously I am exaggerating) and it has generated a lot of emails… mostly from partners of crossdressers.

I mentioned above how much we have in common when it comes to what we wear or how similar our journeys are… but these emails have reminded me how similar the journeys of our partners are.

My journey wasn’t completely easy but it has had so many amazing moments. Photo shoots, finding THE dress, going out en femme…

My wife’s journey? Stress. Fear. Apprehension. Annoyance. Anger. Exhaustion. Confusion. This was, this is HER journey. A journey she did not plan for or expect or want to have.

My journey brought happiness and stilettos. Her journey had few bright spots.

This side of us impacts our spouses and significant others in many of the same ways. Our partners wonder if they themselves aren’t pretty or feminine enough. The same fears of us wanting to transition. The same lack of trust that this revelation came bring.

What has surprised me the most over the years of exchanging emails with partners of crossdressers is that *most* are actually fine with their man wearing panties. They may not understand but they get that this side of us isn’t going away.

But it’s the other things that this side of us brings that causes the most stress… anger… fear… annoyance… among other things.

For example:

My husband only wants to be the girl in the bedroom

My husband keeps asking me to go out en femme with him but I am not ready

My husband lied

My husband spent money on clothes when it was needed to make the car payment

My husband is posting photos of himself online when we agreed on not doing that

And so on.

None of these things are about crossdressing ITSELF. It’s about the other things we are prone to do.

I am not calling anyone out. Again, I am not innocent and I think it’s important that we acknowledge what our partners experience. It’s easy to be selfish and neglect our partner’s fears and insecurities and thoughts.

God knows I know this.

Love, Hannah

9 thoughts on “Her Journey

  1. Great post. Thank you Hannah. You have made the very important point that all relationships and identities that each of us tries to maintain require “work.” They don’t just happen

    Liked by 1 person

  2. Hannah – YOU have a unique totally honest way of writing about our trans CD lives. You write words which are so relevant and true for I believe the majority of your followers – and most males who love to wear female fashions are no different from both of us. I share all of your thoughts and have experienced exactly all you write about. Few people actually write about their true struggles with self confidence, their marriage acceptance issues, and the impact of their cross dressing on others – especially their family.
    This is the first time ever I have written about my life – and it is probably the longest post ever written on your blog – so hope you and followers will not be upset.
    I can recall at about age 12 the first time I ever wore a female dress. It was an internal personal feeling I had never experienced before.
    I living then in a small village in Ireland where I grew up. Like any normal boy I conformed to male dressing standards. But even at that so young age – all I could think about was how much I wanted to dress in female clothes. I would look at all females and admire theit female body and the clothes, make up,hair etc thay all got to wear. How I wondered how it must feel like to be a female – and look so beautiful.
    About age 18 my family moved to Dublin – where I saw for the first time large female fashion stores. I remeber sitting outside of a lingerie store – from outside looking at all the lingerie in the windows – not daring to go inside and see for myself all these sexy products. I watched the females entering the store – and how they must feel dressed in all of this lingerie. I felt I must be the only male in all the world who could feel like this.
    At age about 17 we moved to London – and I worked at a large office building with hundreds employees – and all I could think of was seeing the females and what they all were wearing every day. It was a time and place where females only wore dresses & skirts with tops – leggings and pantyhose were not even invented back then.
    At age 18 I knew I had to get a job where I could travel a bit – and get myself some personal freedom away from my family and friends – staying at small hotels where I could privately dress in female clothes. I found a store and gathered up the courage to go inside and buy for the first time my own female clothes.
    Back at hotel – I fully dressed for first time as a female – including a cheap wig and jewellry. To this day I still remember the incredible comfort and feelings I had on that first day as a female. I need to admit this was very sexual – maybe the main real reason why I loved to do this. For the first time in my young life – I felt this is who I am – and wish to become in all my future life.
    I began to wear stockings and panties most of the time under my male clothes every day – on some Sat nights I would go to the Soho area of London – wearing a thin bra stuffed with tissue – it was cold weather so I could cover up so no one would know.
    I also dated real girls – knew I was straight – only interested in females – had no interest in males.
    The laws in England were very strict at that time re female impersonation – they called it a disguise – and discovery would be reported in all newspapers by police. I had read that USA was much more tolorant – and it had been my dream to immigrate as soon as I could. I got lucky – got my USA visa – and in 1966 immigrated to US – New York – via the SS United States ship – 5 days across the Atlantic. First job in NYC – then several months later to Chicago. No dressing – all I wanted was to make a good life in America. On to Cleveland with a promotion – got married – had 2 children – bought a small home – tried to live a normal life. But always in my thoughts was dressing as a female.
    Next promotion was to Pittsburgh – and for first time in years had to stay in a hotel – as we relocated. So this was the first time I was alone each weekday night to dress in female clothes. And I did every evening – I bought many female clothes – and CD / TG adult magazines – no Internet at that time. But never went out in public. Later promoted again to Philadelphia – more free time to dress as a female. I kept all my female things in a small suitcase hidden in my car.
    One terrible day I found my suicase was gone – went home – faced my wife who I loved – she was very confused – why I did this etc. – was forced to marriage councelers – who advised my wife I had a serious mental problem and best option was to divoirce me.
    So I stopped dressing – did the best I could to live a normal male life. Promoted again to NYC – later to Cinc. Ohio. Bought some new feamle clothes – found a secret locker to hide them in – and dressed again when I could.
    Again wife discovery – but this time was served with divoirce papers. During the court hearings her lawyer presented my female clothes – it was so embarassing.
    So – I decided to move to Tampa Florida – quit job – begin a whole new life – and finally could live my life as I had always wanted – as a part time female whenever I wished. Played a lot of golf which I also loved – but missed my family more than I can ever say. I began to go out at night to gay nightclubs – with drag shows – how I admired these queens. Got to know many of them – but still looked like a guy in a dress – especially with make up. I went to many FI drag pageants – loved every moment as a girl – bought more female clothes – decorated my condo as a female would – no longer had to hide my wardrobe. During this time with the drag pageants like Miss Florida FI in Miami each year – it took them an hour to mnually enter in all the contestant scores – declare a winner etc. I was good with computers / Excel – made a program where I could enter in the score data – and have a winner announced in 5 minutes. By then I knew as friends most of the so beautiful drag queens all over Florida.
    One in particular taught me how to do make up properly – and for first time began to look like a real passible female.
    I co bought with a straight male friend a huge gay nightclub in Tampa / Tbor City – a very famous club called El Goya – with a huge drag show. We re named it the Pleasuredome. We renovated the club into 3 main sections – added a Cuban resataurant – trtied to make it a straight club as much as possible. But built / locked into our building lease wa a clause that the drag show must remain – the building owner loved these shows. We had about 1,000 paid cover charge guests on a Fri & Sat nights – so very successful as a business.
    We soon found out 2 main business things – 1. – almost everyone went to the main showroom with stage and the 2 drag shows every night and 2. our gay guests paid a lot more cash for their drinks – vs. straight guests. So we focused more on the incredible drag shows – made a lot more profits. I as co owner was mostly involved in the finances of the club – also in charge of the drag shows – which I loved being part of.
    Ybor City was like Bourbon St in New Orlaens – lots of clubs and restaurants – with 25,000 visitors each weekend.
    That was when I decided to change my female inage – every weekend night I would dress in fabulous elegant evening gowns – big different hair each night – very ertic make up etc. – Deborah Nicole was known as ” The Queen of Tampa Bay ” – as I was wlcomed in many of the great restaurants around Ybor and Tampa – always promoting our Pleasuredome nightclub. I continued with the drag pageants all over Florida – as Head Judge of most of them. Weekday night I would dress in different outfits – from casual to gothic – no one knew how Debbie would look each night. I even got myself female breasts – love them dressed as a female – but never can go topless around freinds as a male at home or on a public beach etc.
    Just to also tell you I am 100% straight – never ever been with a male sexually – admit to wondering how it would be as a female – but did build my reputation around how I loved everything about female beauty and fashions.
    After 10 years about 2013 with the Pleasuredome – we decided to sell it – Ybor City was changing and it was getting tougher to make a profit etc.
    Around this time I met as Deborah a real beautiful girl called Sierra – and soon got married – had another child – and stopped going our as Deborah – my decision – my new wife wanted me to continue with the pageants – and go out when we could. Her background was cosmotology / make up – female fashions etc. – and she was and still is an expert with this.
    So we decided about 10 years ago to make a small business with our combined skills. Deborah had a huge female wardrobe – Sierra is an incredible make up expert especially with M2F cosmetics – and we made our Sierra Studios bsiness – our of our home. We have made a business out of male to feamle transformations.
    Never in a million years could we have expected the response we have had – males from all walks of life – young and old – guests in all shapes and sizes. We get emails and tel calls every day – people who it seems have no other place to go to help in their female lifestyle choices. Most need help in their cosmetic work – many just wish to be transformed into feamles – we get first timers who just wish to see what they might look like as females – experienced guys whop wish to take their female appearance to a higher level. We try to be much more than just a dressing service – we try to offer many tips and advise to guests to increase their self confidence – most learn mae up as Sierra does her work explaining step by step all she is doing – so guests learn how to do this tehmselves at home.
    We are finding most guests are married men – have good jobs – with god income – highly educated and straight. Most are very nervious when they arrive – settle down after they meet Sierra – and are very concerned about their personal security – fear of others learning about their lifestyle. That is why we never post any photos of guests on our web site – we take many photos – and give the PC memory card directly to the guest – and we never make any copies.
    It si incredible to see how happy these guys are when we are all done with their M2F transformations. Many leave here as females – then go out in public for first time as females – go shopping – ride around in their cars – come back and change back into how they arrived as males.
    We love all we are doing – we are good at it – and love making these guys feel so feminine. Sierra does all the cosmetic work – helps the selection of female fashions – lingerie etc. to wear – all I do is take hundreds of photos of them dressed as females.
    We do 3 sesions each weekday only during the day when our youny daughter is in school – we shield her from our real business for obvious reasons – no weekends – and we charge about half of other similar services. It is all fun work – we bring a lot of happiness to our guests – and it is amazing to see them pose for photos with new confidence in their female appearance.
    This busines is the pride of my life – and I am so lucky to have Sierra as my wife – and her acceptasnce of my lifestyle. I honestly believe there are millions of males in USA who cross dress privately – but are so afraid of their female discovery – and the negative impact on their lives.
    I love my life now – love my wife and children – looking back over all the years America is an incredible country – where even a young guy from rural Ireland can come to USA with a few hundred dollars and a small suitcase – and make the American dream come true.
    Looking back over so many years – have had all the struggles like most of us – have made more than my share of mistakes – but have few regrets. I undersdtand completely all about living a female life – and the impact on the ones you love – been there.
    Now I believe if you truly love someone – you do all you can to make them happy – and accept them for all they are or wish to be. Life is far to short to be unhappy. My best advise is to be honest with everyone – try to compromise in all things – do your best to understand the other person’s issues – and try to work it all out together. But always with kindness, compassion & honesty.
    I admire Hanna for her work and her web site – also my friend Renee Reves – who has the best TG site in all the world. ( http://www.reneereves.com ).
    I admire anyone who can escalate our CD / TG lifestyles – and hope our busines can make others become more confident and beautiful as females.
    I am not into promoting our business on Hannah’s web site blog. I urge other followers to write their story – sometimes it just feels good to share your inner thoughts – and show others like yourself – you are not alone.
    So – finaly I have written my lfe story – how Edward became Deborah.


  3. Her Story is difficult for me to contemplate because I made pretty much every conceivable mistake in bringing this part of myself into a marriage. Needless to say, the marriage did not survive.


  4. Deborah – most interesting story – you must be in your 70’s, I assume since you mentioned ” before pantyhose.” I wonder how difficult it was for you to not see your first 2 children like one would in a regular relationship? Anyway, great that you didn’t expose your young daughter – this is a good lesson for others who aren’t into protecting young children like you did. You have led an interesting life, indeed. I do think, like you and me, that many of us cross dress because of a sexual turn on involved, or a combination of that and other factors too. like the thrill of seeing oneself look like a different female person – fascinating!


    1. Amy – re not being able to see my 2 children was hard – they were 19 and 16 – I am still not sure if my ex wife told them reason for the divoirce. Truth is I would have given up the CD life – not to disrupt our marriage. In end with no alternative I just decided to move to a diffferent city – Tampa – where I could re start my single life again – and try to make the best of a difficult time.
      Today I know there are many guys who CD – and ” struggle ” daily with this choice – stay in a marriage or leave and make a new life away from family. Each person has to mae their own decision – and understand the consequences. There will be no looking back – for we cam’t undo the past.
      I just wish each CD person in this situation makes the best decision – and does the best they can for themselve and their family. From our many business studio guests – most remain in their marriage – and continue their CD time secretly – away from home privately. Deborah


  5. Amy – I am 80 years old – but I think with the silicone breast & facial injections many years ago and cosmetic tricks I feel and look much younger. My wife Sierra is 30 years younger – and very beautiful. Perhaps this is why I still love to dress as a female – I have a small body figure – and with padding etc. can transform myself into a curvy female size 12 dress size. ALL I know is that I feel so “alive” dressing as Deborah – I just feel like I can be a completely different prtson – the female I have wished to become since age 18. Even affter all thes years I still don’t fully understand why I love this – but I do and it makes me very happy every moment I am Deborah. So much so reality now is that I get up every morning about 4 am – dress in a different female outfit each morning for about 4 hours while our young daughter is asleep – then about 8 am change back into male clothes still with pantyhose etc underneath. My wife Sierra joins me at any time – and acepts my love of female dressing. In a few weeks when our daughter returns to school I can female dress all day – and once again re open our CD male to female transformation business – which we can’t wait to do. Looking back I have no regrets – past 25 years have the best times f my life with the freedom of being Debbie almost whenever I wish – but I also know once any male starts cross dressing it become a lifetime of adiction. I know this from most of our customers who still have to hide their lifestyle from family. To us it is very rewarding to transform these guys into the ” woman of their dreams ” – and see how happy we can make them.
    My advice to everyone come from the worst day of my entire life – my son age 39 with 5 yound children – a big strong healthy guy – died of a sudden heart attack. I swore that day never to take my or any life for granted and to live every day like it was ” our last day on earth ” – and live my future life for myself and the ones I love. And I do ! – with reasonable compromise to my family.
    Self honesty to a wife can in most cases make both lives more happy – for if someone loves another – the way to do this is to make the other as happy as posible. Debbie.


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