Saturday, June 28, 2008

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.

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