Adventures Awaiting the Novice Cross Dresser

I can remember as a child walking in my mother's and father's shoes.  Such little feet slipped all the way down into my mom's pumps and walking around was not too difficult unless you caught the heel on something and tumbled.  As an adult I find that walking in heels is more like ice skating with low top skates.  It's the side to side wobble that will get you if you don't watch out.  I have gained great admiration for anyone who can run, dance, jump or power walk in heels.

Applying makeup is surely an art and I can believe too that when you take off your bifocals and try to work in the mirror that completing the job and looking presentable could well be a miracle.

Where does that little stripe of fingernail polish hide in your cuticle and lie in wait only to slip out unannounced 3 days later??

OK, I'm sure that genetic girls have been practicing these things since they were preteens and have spent untold hours in the bathrooms and at friends places working on their look, their hip action in platforms and their fashion sense.  That just means that the novice cross dresser must be dedicated to hard work, a keen eye, great balance and grace as well as much trial and error.  No worries, I'm up to it!

I actually purchased a set of ebooks - The World's Best Cross-Dressing Guide - and have begun my home study.  I'll put a link to it in my sidebar if you'd like to have more information.  I can also practice my female voice while reading it to myself.

So much to do in LeeLee's World. :)

The First Time

Once I'd set the date for my first venture into cross dressing under the guidance of Mistress S., I had to decide what I needed to acquire so that I could actually have some clothes, etc. to cross dress with.  Funny, that hadn't really crossed my mind until we had confirmed our session.

Thank goodness for the internet and Google.  I had no idea how much information is available for searches like "cross dresser clothing" or "plus size lingerie" or just "cross dresser".  As with so many things on the internet, much sifting was needed to find a few good sites for quick and discreet purchasing.  My first venture was to a local shop specializing in adult toys and clothing.  Taboo is its name and the girls who work there were a big help.  So out I came with some fishnet thigh highs and a crocheted body stocking.  Stretchy stuff kept me from having to figure out what women's sizes really meant.

Next I headed to eBay and found a wig shop from the midwest that had a great sale going on.  Synthetic wigs in lots of styles and colors for under $20.  With such a good deal on the wig I splurged on the shipping and got it via express mail.  Shoes next!  As in my first "live-and-in-person" shopping trip for things femme at Taboo, this trip proved exciting as well.  I went to a discount shoe store and shopped boldly armed with my proper shoe size (thanks to Euro sizes and conversion charts on the internet)  I found a really cute pair of gold sandals with a 2 inch heel (I hoped that I could walk in them without injury).  A little basic makeup from a stash of samples gave me enough supplies to be ready for my first time experience with Mistress S.

The night before I was excited about the encounter and sleep come slowly.  The next morning I had some butterflies but over the past week this had seemed more and more right for me, so I packed up my things and headed off to my first time.

After navigating through gridlock from an accident on the interstate, I finally arrive nearly on time and meet my new mentor at the door of her building.  We greeted and I unpacked my things to show her what I'd gathered together.  In our email communications Mistress S. had asked me how I would like to proceed in our session and being so novice, I had told her that I would be happy to let her plan the way she would like to take me.  Her suggestion of guiding me through dressing and learning makeup techniques sounded great for a start.

She opened up the body stocking and helped me get it on (I'll write more about the adventures of dressing for the first time in my next post).  She then did my makeup while I tried to follow what she was doing so that I could practice on my own later.  The wig and shoes were next and a necklace and earrings I'd made and brought completed my outfit for the day.  I did indeed manage to walk to the mirror to check out my new self without injury but I knew that I'd need to learn more of the tricks for walking in heels.  Mistress S. suggested that she could do my nails and I agreed quickly.  She used the same polish she had on and then showed me how to dry them.  

I was pleased with how comfortable I felt in my new LeeLee persona.  We did some walking practice and I found that walking in heels requires placing your foot down much differently than you'd walk in men's shoes.  It's mostly backwards from the heel-toe step that I was used to.  This required more of a toe-heel step that puts the ball of your foot down first for stability.  A few times across the room and back and I began to get the hang of it.  My exam came when I had to carry a cup of hot tea from the kitchen to the sofa. I passed!! (the walking exam that is!)

Most of the rest of our time was spent alternately talking and improving my walk.  Soon I was pretty much comfortable with walking using a little hip action.  Mistress S. let me use her crop to add some attitude to my walk and that was a breakthrough moment.  LeeLee was real and she could strut :)  Maybe LeeLee will become a CD-Dom one day but you will have to stay tuned to find out.

Shortly,  it was time to remove the polish and gloss to return to the real world.  But the truth is that the real world changed for me that day.  LeeLee's world was created and she will change my life in untold ways.  There will only be one first time but I'm certain that there will be abundant new experiences to explore as I spend time in LeeLee's world.

Why Now??

Sometimes a plan just comes together, even if you didn't have a plan.  Strange as that sounds it is often true as we live our lives.  Whether you call it the stars "lining up just right" or that it was "just meant to be" or as in my case a simple "congruence of events" that led me to a door that I had kept closed for a long, long time.  Two months ago I had no plans to explore cross dressing and yet today I have acquired several outfits, some lingerie (plain as well as sexy), a wig, shoes, makeup and silicon breastforms and a new name - Leelee!

The actual events that merged into need and desire for this new me are truly not important.  It is sufficient to say that the demands on my time by others was enormous and compelling.  None of them could be ignored and I soon found myself riding a tsunami that required me to give so much of me to others that I was neglecting myself to my detriment.  I must say again that all of those demands and needs were real and absolutely required me to give what was needed as best I could.

One night, late, I was reading some posts on an adult board and came upon Mistress S.  She had linked to her blog and I began to browse through a few weeks of posts and some of her specialties as an idea sprouted.   I contacted her by email and inquired about whether she could assist me in learning to become a cross dresser.  Her reply and subsequent emails all assured me that she would be very willing to lead me on this new adventure.  So from sprout to blossoms, a cross dresser in spirit became a cross dresser in fact.

Mistress S. has given me so much support and encouragement in the short time I've known her that I can hardly express my sense of gratitude.  I said in a previous post that I found a girl to girl relationship was an extraordinary experience and one that I'd never imagined.  I look forward to allowing my LeeLee to grow and become stronger.

A couple more thoughts about my past as it led to my present.  I have always been attracted to certain feminine things.  Makeup, especially eye and lip colors, has held great fascination for me.  Once or twice I have "dressed up"  in the privacy of an empty house and enjoyed it.  I have never entertained the notion of dressing up around someone else until now.  Things transgender were often appealing but I did not see myself in such a role until now.  Over the course of time and work and raising a family, these fascinations and TG dabblings were pushed away and nearly forgotten until now.

Sometimes a plan just comes together, even if you didn't have a plan.  Happily!

To Pass or Not??

I have come to know that what motivates a cross dresser to dress femme varies widely.  If the desire is to pass as female while working, shopping, clubbing, etc., then the approach to cross dressing becomes far different than if you only wish to be female for a while and then resume your normal role as male.  For myself, I wish only to explore my female self and find a few friends - or even just one - who will share these times with me.  Crossing in my day-to-day life would be unacceptable to those who matter to me and so I have chosen to seek a safe place to take on my female self and allow those few who are accepting of this to be my friends and encouragers.  Surely you can dress up in the privacy of your empty home, but there is a social void that makes cross dressing alone  unsatisfying for me.

What I have discovered is that having a friend who is a girl to guide me has given me a completely new sense of self as a female.  This one person who has enabled me and empowered me has also shown me the dawning of a relationship with a girl as a girl.  That girl to girl relation has provided me with a sense of affection that doesn't exist in my male to male or male to female relations.  It is extraordinarily unique and pleasing and for that I am so grateful to her.  I will share more about her and how I came to find her just as I will share what brought me to this point after so many years of putting it out of my mind as I write future posts.

Getting To Know Me

This will be short because it's late.  I am new to the world of cross dressing but it has been in my head for many years it seems.  I'll use this blog to delve into what drives me to explore this experience and hopefully what I am learning about myself in the process.  I will share experiences and what resources I am finding to enable myself as a cross dresser.