I know the most common thought(fear) many of us have if we are not really "out" is getting caught by family, SO, or the wife, but I am curious to see how many of us as kids, actually TRIED to get caught as a means to force the "conversation" with family etc.

I know I did on several occasions starting at around 6 years old. I discovered my sister's pink nylon babydoll PJs. (1959 approx) and was hooked. Several times I would sneak them out of her room and put them on. I fell asleep ON my bed (not under the covers) and Mom woke me after a while and asked why. I said they felt nice. She said then I would wear them a while longer so my sisters and Dad could see. This repeated on and off and I tried on most everything they had. Then as a 10 year old, I discovered Mom's nylon nightgowns.

I got to the point where I knew I wanted to talk with them about why I liked them and REALLY wanted some of my own. I was getting to the point where I really wanted to wear EVERYTHING girly- underwear, dresses, petticoats, nightgowns- EVERYTHING. I wanted to talk with them about it so bad it hurt.

Into my early teen years I would sneak out a gown and wear it to bed, hoping to get up early enough to return it to Mom's drawer. Sometimes I did and sometimes not. Each time Mom would quietly get it, wash it and put it back in her drawer.

One day I discovered something of my sister's I had never seen before. Back in the day, young girls frequently wore "sanitary panties" during their starting periods. My sister had white a pair that was white nylon over a soft plastic liner. I put them on and then Mom's nightgown and the feelings were electric. I did not know but Mom had already decided to get me my own gown just to keep her daughters happy that I was not wearing their things. One day mom came home with a bag from a local dept store (Woodward and Lothrop for those in the DC area) and told me she had a surprise for me. She called me in and I decided to come out of my room as I was, so very nervously out I marched in her nightgown and the panties. She was sort of OK with my wearing her gown but was furious that I was wearing my sisters panties. She said "well now those are YOURS and put this gown on. This is also yours." I tried to get her to just talk with me about all this. She just said she didn't understand and did not want to talk about it.
She told Dad I had "done it again" and he came in to see me and ask me why. I stammered a lot and told him I did not know but I needed to talk about it. He just shook his head and walked away.

This type of activity continued through my teen years. I would even go down into the apartment basement tunnel areas between the buildings and into the laundry room HOPING to get seen and caught and HAVE to talk about it with somebody.
On several occasions, I would actually get into my newly acquired panties and peignoir that mom bought me (white, floor length, with rows of fine ruffled lace on the bodice and a very full skirt on the gown and peignoir- VERY femme) go downstairs and out the back door of the laundry room letting the door lock behind me. Now I was in a grassed park-style area between the buildings and in full view of 50 apartments.

I would go out into the center in full daylight and kneel in the grass with the gown arranged all around me and simply relish the feeling of being outside in the bright sun and in full view while wearing a beautiful very girly gown.

To this day, I am not sure what I really wanted aside from forcing a conversation SOMEHOW about my desire to dress. Granted it was taking a big chance and was embarrassing to my family as they heard about me from a LOT of folks.

My older sister was the one to finally allow me to talk openly with her many years later. She even sent me a full rainbow color palette of eye makeup and regular facial makeup.

I know this was an unusual way to start on the CD(TG?) road but I am curious if I am alone in this experience or if others tried similar tactics.