Mary's Journey Pt. 01

Prologue

My name is Mary, but I was born Michael. While what I have written here isn't my whole life's story, it is about the start of the most important part. I have skimmed over the early days and concentrated on how it was that I fell in love with the man I still love today. There is much more than this part of the story to tell and I may tell that in the future, if there's any interest.

In most stories I've heard - be it on line or in person - there was either, a specific event that unleashed a hidden or suppressed desire to dress or become a girl, or dysmorphic feelings present from an early age. For me it was different. There was no one event that led me to Mary, but rather a series of small events that resulted in a gradual awakening. As I grew and experienced these events, Michael morphed into Mary.

The story is almost all true - I've just changed names (of course) and some of the smaller details to protect anyone finding out who it is actually about. The big events all happened, so I really see no need to change them.

Sex between any character only occurs when they are over eighteen.

I hope you enjoy it.

Chapter 1 - The Beginning

As I look back, I try to be thankful for the good and the bad that has befallen me in my life. After all, it's the combination of both, the love of our family and friends and the choices we've made, that have led us to this point in our lives. Where am I, right now? I am about the happiest I think I could possibly be. But it wasn't always that way.

The worst of it all? Easy. The death of my mother when I was fourteen and a half.

From shortly after that horrible day, I began a steady but gradual transformation, from a boy, into the woman that I am today.

My personality and interests, aligned more closely to my mom's. I loved spending time with her, cooking and helping around the house. I just got so much enjoyment out of doing those sorts of things. She was always caring, patient and gentle with me and I have tried to emulate that in my adulthood. At five foot six inches, she was slim, had a little butt, narrow hips, B cup boobs and most days appeared almost plain. That changed completely, however, when she put on makeup. When she did, she was stunning. Capped of with naturally wavy brunette hair, mom never showed off her beauty, unless it was to dad. My Dad loved her beyond measure.

My father, Craig, was an only child. He was almost six foot tall and on the larger side of medium - carrying a few additional kilograms where I know he didn't want it. A civil engineer, he would sometimes spend a month or so away on large construction sites. He was a bit of a travelling trouble shooter for his company. His parents had developed a couple of quite profitable businesses. Both mom and dad had grown up in middle class families - solid, reliable, honest contributors to society.

The main thing that I loved to do, that aligned with dad's interests, was play golf. He introduced me to the game at age nine. He loved it and so did I. I still do to this day. It didn't matter that I was small for my age. Because in golf its and individual test of skill and handicaps account for the differences in skill level. While I wasn't able to drive the ball as far, my prowess with irons, chipping and putting, allowed me to quickly become one of the better juniors in our region.

Golf was my one love outside the house and it's how my best friend, Harry and I, started and maintained our friendship. He was probably about the only real friend that I had growing up. I spent almost as much time at his place as mine. We were at the same golf club and we competed against each other, all the time. One week, I'd beat him and the next, he'd beat me. While we went to the same school, we rarely had classes together, so we had different friendship groups at school and in other co-curricula activities. Being friends with Harry always seemed effortless.

I want to skip over the details of the day that mom died. Suffice to say that, dad was away, and mom was involved in a car accident on the way to pick me up at the golf course. If it wasn't for Harry's family taking me in, until dad could get home, I'm not sure what would have happened. They were so supportive and Harry's Mom, Amanda, wouldn't let me out of her sight.

From that time, Amanda provided a fantastic and consistent female influence in my life. She was as caring as my Mom and always seemed to know when to give me a hug and an encouraging word. Ken, Harry's Dad, was very supportive as well, and they both treated me like I was a member of the family.

The changes that occurred over the next four years, were at times very small, but always gradual. Dad was always supportive. He didn't push or hold me back, but let me be me and come at my own pace, finding my own way to Mary. It went from dressing around the house, to hair, makeup and... well, here's some of how that all happened.

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After finding out that I was wearing some of mom's old nighties, dad bought me some of my own - with some underwear. At the time we had a long hard talk. He said that he could see that it was the real me, but he wanted to establish some ground rules."I think, if you're going to continue to wear girls clothes, it should only be inside the house. And only when we don't have guests, like Harry or people from my work. Other people may not understand and they may not accept you doing this. You should put them all away in the spare room, so no one sees them in your draws, too. I also think that you can wear them whenever you want to. You should never feel like you have to wear your girl clothes. Ok."

"Okay Dad. I think that's fair," was my reply.

"Also, if you want to wear more girls clothes in the future, just talk to me and we can buy you some stuff. Ok?"

Puzzled, I looked at dad and asked, "Like what Dad?"

He answering straight away. "Well baby. If you want to wear dresses or other girls clothes. Things like shoes, high heels, or even jewellery, makeup, or wigs. I'm happy if you want to do that. You don't have to, but if you want to, just ask. You could even wear some of Mom's clothes and makeup and stuff, if you want to try it out. Okay baby?"

I paused in shock and said, "Wow. Thanks Dad. I'm not sure about any of that just now, okay?" He nodded in return.

Smiling he said, "Oh, one more thing. If you're dressed in girls clothes, I think you should have a girls name. Just so I don't call you Michael when you're dressed as a girl."

That very question brought a smile to my face. "I'd love that Dad."

"Do you have a particular name in mind?" He asked.

Thinking about it, an idea came to my head. "What about Mary?" I asked.

Dad smiled broadly. "Okay Mary my sweet girl. From now on I'll call you Mary when you're in girls clothes, and its just us at home. Are you happy?"

I was ecstatic. Pretty much from that moment, I took to calling dad, Daddy. After all, isn't that what girls called their dads?

It wasn't that long before I started to want to wear more girls clothes, than just nighties and underwear.

Chapter 2 - An Expanded Wardrobe

I was staying at Harry's one night, late in my sixteenth year, when I happened to see his sister's night routine with her hair. She was brushing it out when I walked past her room. Even that fleeting moment, was a trigger for me to want more feminine hair, just so I could look more like a girl.

So for about the next three or four months I grew my hair out. By the time I had turned seventeen, my hair was getting pretty long, with the back now down almost to my shoulders. I had mentioned that I wanted to get my hair styled to suit Mary and Michael. A couple of nights later, dad asked to have a talk. "Hey Mary. I have been thinking about how we can get your haircut to suit both Michael and Mary. Over the last couple of weeks, I've done some investigating and today I had a chat to mom's old hairdresser, Sally Richardson."

He had my immediate and undivided attention, and when I didn't say anything, he continued. "I didn't tell her that you dress up as Mary, but I did say that you wanted a cut that was in between manly and girly. I think that she got what I was trying to say. So she suggested that if we go down there at seven o'clock tonight, you can get the full treatment and you'll be the only one there."

I loved the idea and readily agreed. "Right... " he said, "you better get dressed into something that won't give Mary away, but is comfortable. And obviously we'll have to call you Michael."

When we got there, dad introduced me to Sally, and she immediately gave me a big hug, saying that she had loved my Mom. She was a very well dressed lady, with stunningly long and well styled hair and her makeup was perfect. The dress she was in and her nails just completed the package. I was amazed and basically couldn't speak because there was too much to look at and admire.

Dad said that he needed to go shopping for a bit and Sally told him to come back in about two hours.

Sally and I hit it off straight away. She told me that I looked like mom. We talked and talked as she washed my hair. As she had me sit in the chair, she was playing with my hair, when she asked, "So. Something neither manly or girlie?" I nodded. Her next question stunned me to my core. "Do you just dress up at home Michael?"

Seeing a look of shock on my face and before I could reply, she added, "Don't worry dear. Your Dad didn't tell me, but I can see that you like the softer things. I think it's lovely and you have a face and body that would make you a stunning young lady. We'll just do your hair tonight, though, Ok?"

I have never been more red and lost for words. Sally spoke softly. "Michael dear. It's perfectly alright!" She hugged me from behind, adding "You are perfectly alright, sweetheart. There is nothing wrong with dressing as a girl. Nothing wrong at all!"

I started crying. For so long it was just Daddy that knew. Now Sally had guessed, after meeting me for less than twenty minutes. "It's only Daddy that knows Sally. And I only dress at home. How did you know?"

Sally smiled broadly. "Oh dear. When you've been styling hair for as long as I have, you get to know people - men and women." Fluffing my hair still, she giggled. "Now I can't call you Michael when you're here by yourself. Do you use a different name when you're dressed as a girl?"

I was pretty much over my shock by that point, and wiping the tears from my eyes, I said "When I'm dressed at home, I'm called Mary." I said somewhat proudly.

"Mary it is then!" Sally beamed with smiles and love. "Now, I think I know exactly what to do with your hair Mary. We'll have to do a few cuts over time and let it grow another few inches. But when it's done, the style I have in mind, will be perfect for your face and body." Sally showed me the style in a magazine.

She got to work and we started chatting. I had so many questions about hair and I loved the style she'd picked out for me. Soon enough though, I started asking more questions about nails and makeup and dresses. It was like, having Sally know, gave permission for Mary to emerge more fully.

Dad came back at the appointed time and sat in the waiting area. Sally was just finishing the blow dry and final styling. Happy, she said, "There you go Mary. That is a great start. You look just lovely. Remember what I said about doing your hair for Michael, though." I was so happy, that all I could do was nod. She handed me a magazine before continuing. "Now, just look at that for a minute, while I get your father to pay."

Realising that Sally had met Mary, Daddy was all smiles when I looked over at him. I smiled back, when I saw that he was happy about it.

Daddy and Sally had a chat for a few minutes while he paid. As we left, Sally said to me "Good night Mary. I hope you have a great weekend and I'll see you for our appointment in about a month. We'll be there quicker than you know dear." She hugged me and kissed me on the cheek.

On the car ride home daddy said that he just loved my cut. We talked all the way home and past eleven o'clock, about Sally realising and what that meant for both of us. I could tell that it was a relief for him, realising that he had carried the burden of Mary all by himself for so long. We even talked about, nails, makeup and dresses. Daddy, as he had always been, was just great, saying that if I wanted to do any of it, he would support me.

I said that I'd need to think about it a little more, but that I thought I'd be interested. I said that I at least wanted to try. "Well I'm not sure if any of it will still be ok to use, but you're about Mom's size now and you have her complexion, so you can use any of her things, if you'd like." daddy offered.

Over the next three or four months I had late night appointments with Sally. She got my hair to a point where it was about an inch or so past my shoulders and looked great at school, but allowed me to dress as Mary and really look the part at home.

Over the months of my seventeenth year, Sally also helped me with lots of other things too, like developing my feminine voice, female mannerisms, all the way to nails, makeup and dressing as a lady - including what was good and not good for my body type.

At about seventeen and a half I was dressing as a woman almost every night. I had grown my nails out to about the longest acceptable length for a guy, which translates to quite short for a girl. I waited for the weekends to paint them, but only when I wasn't going to leave the house.

Clothes were a different matter. I wasn't quite the right shape for Mom's dresses and stuff to fit me properly. There were a lot of her clothes that I thought I should keep though. What I didn't want, daddy said was time to let go of. There were quite a number of outfits, including dresses, skirts, blouses, shoes, stockings and on and on and on. What I didn't have, we ordered on line, returning the ones that didn't suit or fit me properly. The number and type of undergarments I ended up with was extensive.

As my feminine persona developed and came more to the fore, so to did daddy's and my friendship with Sally. She regularly visited, for meals that I would cook, and stay to spend time with me doing one thing or another. I gradually came to act and be feminine, more and more, around the house, to the point that it was pretty much all I would be inside. Gradually daddy, Sally and I talked through some of the harder things, always finding the right place for me, with a plan for how to keep moving forward and growing.

In all this time, I had never developed a desire for a boyfriend or girlfriend, I was too wrapped up in finding myself to consider anyone else. I also actively chose to not consider the idea of formal transition. It didn't really feel as though I was actually changing, it was more like the real me was developing, and Michael's development had halted. What was happening just seemed natural, and that's exactly the way that dad, Sally and I treated it.

Chapter 3 - Almost There

Just after turning eighteen - and about to finish high school - I came to realise that there were two things holding me back from fully becoming Mary, my true self.

The first was my boy bits. I had come to call them Mr Mary, as they were the easiest way that someone could tell I was male. That and they were the only male part of me left. I rarely got erections or even aroused, but as it was still very much smaller than average, it presented an issue when it came to jeans and the like. I wanted to wear jeans and fitted pants and longed to wear bathing suits, all with an authentic female appearance. However, I was prevented from successfully wearing the styles that I wanted to, because of Mr Mary.

I found a store on line that specialised in just that problem and before I knew it, I was tucking and was thus able to wear jeans and pants, without the appearance of young Mr Mary. It was something that daddy and Sally both commented on, when they noticed it, the first time I wore a set of fitted pants.

I had purchased a pair of tan coloured high waisted, bell bottom pants. They were quite close fitting across the waist, hips and crotch. But wearing a gaff, they showed no bump at all. My crotch looked just like any woman's. I wore them with a white blouse and white three inch heeled shoes.

I had cooked a wonderful beef stroganoff and as I walked into the kitchen, after dressing and doing my makeup, daddy woof whistled. I spun and he said that my butt looked great in those pants, but what had I done in the front. Sally looked and quickly added that she thought that area looked very feminine.

I told them about the gaff and how I was tucking and after allaying their concerns about possible physical effects, daddy and Sally both said that I now looked one hundred percent female there.

Once I had confidence that I could tuck, using several methods, I bought a number of bathing suits. They looked so good on my little bubbly ass, that I ended up with over a dozen pairs - some very skimpy g-string varieties with gaff bottoms and some one piece and conservative.

The second thing holding me back a little was breasts. I had purchased a few sets of a-cup breast forms and could use them to create the illusion of breasts and cleavage. They were not, however, any good when it came to skimpy lingerie, bras and swimwear that were designed to display at least portions of my breasts. Not much I could do about that for the moment. I had discussed the idea with daddy and Sally, but again rejected starting hormones. I had come to trust my inner voice on most things, letting that guide me.

One thing I never had any interest in were the more stereotypically over the top feminine outfits, like dressing up as a doll or a cartoon character, that crossdressers sometimes wore. Or things like typical drag outfits. I was quite conservative, when it came to my femininity. I wanted to be as authentic a woman as possible.

On the advice of Sally, I went and saw a personal trainer she trusted, and was given a diet and training program aimed to keep me trim, but to also shape my hips and butt to be more feminine. I didn't want a full on big butt, with the thighs and stuff to go with it. All I wanted to do was to emphasise my cute little bubble butt a bit more and maybe add some to the almost non-existent flare of my hips.

The diet and exercise worked well and my butt got, what I thought was, a perfect bubble. I really loved the way it and my legs looked in bikinis and things like short shorts and exercise gear. The only thing that remained a little male was some persistent lower belly fat. But that would eventually go. It wasn't a lot, with it making my waist about an inch, or possibly two, larger than I wanted.

At one point, I was worried about how much all this indulgence was costing daddy. I expressed my concern and the next day he sat me down and told me all about the family finances. Mom's life insurance was a huge amount of money, daddy had inherited a large sum and the two businesses from his parents a few years before. Each of those was making a steady profit and he didn't have to do a lot with them, as they had their own operating structures with CEOs etc. So he said that money was not something that I would ever really have to worry about.

We were at the kitchen table. Daddy paused and then turning to me, his eyes got serious again. "Just because we have some money, doesn't mean you can just sit on your cute butt for the rest of your life. I want you to find what it is that you want to do with your life, to conquer it with as much vigour and courage as you've shown becoming Mary. You need to go out and find your place in the world."