dare you

I mentioned this before - I have a bit of a fascination with being cross dressed in a self imposed dare kind of a way.

I don't really know how this started, but I've been doing it since I was a teenager.

It usually involves hiding a key to a padlock in a remote location, going to another location, getting dressed up in something suitably girly and then locking my male clothes with a small chain or in a lockable bag, leaving me with no choice but to walk all dressed up to retrieve the key.

I used to do this in a local woods which was pretty fun, but then they opened up the place to mountain bikers and horse riders, which meant it was pretty easy to get surprised and I didn't really want that.  I had one experience in my late teens where I got spotted whilst wearing an 80's short puffy ballgown on a wide path by 2 girls on horseback and they decided to give chase - I had to take off my stilettos and run for my life - just making it to a steep hill where they couldn't follow.  I lay in the bracken, hidden under all the greenery for an hour until I was sure they had gone.

Of course, this kinda made it more exciting, rather than putting me off, so I just did it more - sometimes even in handcuffs and in ever more ridiculous clothes.  I even got hold of a full length pink taffeta bridesmaid dress with huge skirts, layers and layers of petticoats, puffed sleeves and the works and had myself trying to walk a mile or so through the woods to a huge clearing where I had stashed the key to a padlock that now held a chain around my male clothes and secured them to a tree.  Oh, and I also did this in handcuffs.  Good times :)

More recently, I've played with Dorothy from The Wizard of Oz and Alice in Wonderland costumes, complete with voluminous petticoats and of course the requisite shoes - red mary janes for Dorothy and black patent ones for Alice.  I have some cool stories about those :)

I also got several school uniforms - original American Catholic school plaid pinafores - complete with round collar puffed short sleeved shirts, white knee socks and those gorgeous patent mary jane school shoes.  I had the dresses shortened slightly so they were just above the knee, making them slightly more 'obvious' (as if they weren't already)

I spent quite a few hours 'trapped' in such an outfit outside in broad daylight, having left a padlock key in my car, walked several miles into the countryside and then locked my male clothes in a sturdy bag and chained it to a tree.   It was a pretty scary walk to the car I can tell you - lots of walkers and I made sure I parked the car in a very busy spot.  I didn't get seen, but it took a very long time to get back to the keys and then back to where I had left the clothes.    Once, I drove out to a quiet spot in the early evening and locked my clothes away, leaving me dressed as a schoolgirl, but for extra fun I had left the padlock keys at home.  I then faced the problem of having to wait several hours before it was dark enough to go home, but even when I got back, my house was on a busy street and open to everyone to see.   There's a feeling of excitement and slight panic that rises from my tummy and up my chest when I do this - I can even feel it now just talking about it.

I used to work out more and more intricate placed to leave padlocks that unlocked keys to bags containing more keys to other locks, meaning I'd have to walk here there and everywhere to get myself free.  I lived alone for a while and worked out that I could lock the back door key to my back gate, effectively locking me out of the house - so whereever I put the key to the padlock was somewhere I had no choice but to get to whilst I was all dressed up.    Once I forced myself to walk (at night, of course) a couple of miles through my neighbourhood, with all the possibilities for discovery, across busy roads and down narrow terraced streets in my Alice in Wonderland outfit.   That was pretty intense.  I had to hide out for an hour in someones front garden when a bunch of people came back to their house in their car and sat outside chatting and smoking before going their separate ways.

Stories stories...

Interested?  Go on, I dare you...