My First Public Outing

​ February 2003

My first attempt to dress in public I was probably around age 11-12.  My older sister attempted to get me dressed up as a cheerleader, but after she had me dressed up I chickened out because I was scared what my dad would say.  So needless to say I didn't make any public appearances.  When my sister moved out she left behind some boxes in the basement and I was extremely happy to discover the cheer leading skirt and a few other girlish outfits in the boxes.  I would sneak down stairs and put on outfits whenever I got the chance.  I can say that I spent many hours hiding in the basement dressed and dreaming all the while wondering why I had this urge to dress up.  Many times I would just barley keep from getting caught by my brother.  The issue of dressing and being attracted to girls things go back to when I was 6-7 years old at my earliest memory.  Although I didn't dress at this age my thoughts about wanting to wear girls things was vividly active.  Since I shared a room with my brother I didn't get to dress up.  As time passed and I got older I can remember wearing pantyhose to school and constantly watching girls wishing that I could wear there clothes.  Many times when I started working I would wear panties and pantyhose under my uniform.  Once I got off work I would go home and hang out in the back yard dressed up trying to gain the courage to venture out around the block.  Sometimes I would make it a house or two away from the house, but my big break came on Halloween.  I decided that since I was going to work that my opportunity to dress up and go out in public would be Halloween.  After many scary trips to different stores I was able to compile a complete maids outfit with everything I needed.  I then convinced my best friend dress as a pirate girl so that I wouldn't be dressed as a girl all by myself.  I was able to do this cause I gave him a ride to school everyday and the threat of making him ride the bus got him to see it my way.  On Halloween I Started by shaving and polishing my nails.
I then put on panties, fishnet hose, bra, black dress, French maids dress complete with accessories, heels, wig, and make-up.  You did notice that I did have two dresses on cause I was scared to death to wear a dress that short.  My wig was red long hair about halfway down my back,  I can remember walking in the store at the mall shaking like crazy but the gal was very nice and gladly took my money.  The heels I believe were around 2.5 inch heels in black.  My make up was done to the best of my ability as I hadn't had a whole lot of practice.  I was shaking as I left the house but I was very determined to get out.  I also am very punctual when it comes to work so I knew was I arrived there that I would stay for my full shift.  At work I got many comments some good  some not so good but nothing extremely bad, and my poor friend showed up dressed as a pirate girl.  He changed shortly after the start of his shift cause he brought other clothes.  I on the other hand didn't bring any other options and stayed dressed up all night.  It was kind of funny cause I had stuffed my bra with tissues and they kind of went flat but with some experimenting later on I found out that Big classic boxes made excellent boob shape so my tissues were replaced.  In all the excitement of the night I can't say that I had anything but a great time.  Once I got done with closing the store which was a great challenge cause heels aren't really ideal for wet tile floors I went home.  At home I still was on an extreme high from the nights activity and wasn't really ready to undress.  I ended up sleeping the night away all dressed up tucked tightly under the covers with make-up on and all.  In the morning, I got an extreme surprise of my mom standing in my room asking me to wake up.  Once a wake I realized I was still dressed up and mom gave me a weird look anyway she was wondering if I could put the new carpet in the kitchen today.  I told her sure and got up, and I still was not ready to change so I just went out to the kitchen dressed up.  Thank goodness Dad was out of town or I wouldn't done that.  I started scoping out what I would need to change the carpet while I had a bite to eat.  While I was still dressed up I changed the carpet much to my moms surprise.  She did suggest a couple times that I should change, but never really pushed the issue.  She did take a picture after I had fixed the make-up.  Anyway I did finally go back to male mode with a greater desire to dress again.

kimberly@kimberlytiffany.com