First Time Outside - Dressed.

I can remember like it was yesterday.

I was about 15 and in the house alone one evening, my younger sister and parents were going to be out for hours.  It was dark and snowing lightly and I lived in a peacful neighbourhood so it was quiet outside with no-one in the street.  I had dressed in my sister's clothes around the house but I never had the courage to step outside - that night I had an idea.  I put on a pair of tight speedo style swimming trunks, some of my mum's tan panty-hose and one of her black bras stuffed with socks.  I used a leather belt threaded through the leg openings of the swimming trunks - pulled tight around my waist it held the trunks high on my waist - helping to hold my 'equipment' pulled back between my legs and giving me a smooth front.  The belt also pulled in my waist giving the impression of widening hips.  Next I put on one of my sister's white school blouses, her school tie,one of her navy blue straight knee length school skirts and a pair of her long beige school socks.  After posing in the bathroom mirror, examining the black ouline of the bra through the blouse, I added mascara, eyeshadow, blusher and lipstick.

Checking outside I could see that the road street was still clear, I squeezed on a pair of my mum's high heeled brown leather boots and buttoned up my sister's navy gabardine schoolcoat and fastened the belt tightly around my waist, emphasising my hips and breasts.  Stepping out of the house I locked the door, put the keys in the deep coat pocket and pulled up the square cut hood to cover my short hair.  Tentatively, I started to walk away from the house - glancing around to check that the neighbours' curtains were drawn - my heart was thumping and my mouth was dry.  Gathering myself I continued walking, turned left out of the front gate and up the street - my aim was to walk clockwise around the block and return to the house - I estimated it would take 10 - 15 min.

Outside it was the special kind of quiet that you only get when it is snowing but the snow cover on the pavement was not deep enough to muffle the clicking of the high-heeled boots I was wearing.   I felt that eyes were peering at me through darkened windows - attracted by the noise as I walked.  Conscious of being spotted I put all my efforts into walking as naturally and femininely as possible - putting one foot in front of the other, swaying my hips and holding my elbows in to my body, wrists facing forwards.  Although I had worn heels around the house I was not used to walking any distance in them and the muscles in my calves and thighs were tiring and I was slowing down.  I was too nervous to stop and rest so I kept walking to complete the circuit that would take me directly home.

As I approached a T-junction - where I wanted to take a right-turn that would take me back in the direction of home I spotted a dog-walker coming down the hill towards me.  I panicked, not wanting to arouse suspicion by turning on my heel, I took the left turn - whilst this would still get me home it would double the length of my walk.  I dare not look back and not wanting to attract any male attention or get caught dressed as a girl I quickened my pace although my calves were burning.  At the bottom of the hill I took a right-turn and glanced over my shoulder - just my luck the dog-walker was still behind me although held back by the dog sniffing at lamp-posts.  Continuing, I made another right turn that would take me up a long straight hill towards home, glancing back again I could no longer see the dog-walker.

I was relieved not to have been discovered but my calves were begining to cramp and my toes were crushed in the tight boots - they would hav ebeen more comfortable without the socks.  I was only two-thirds of the way round and feeling pretty sorry for myself - I felt like I could cry.  I was praying that I would not meet anyone else and planned to pretend that I lived in one of the houses and hide in the garden if I did - I could not bear to turn back now.  I was lucky, I made it to the top of the hill and took the final turn that would take me home.  The last steps were agony and after unlocking the house door I fell inside desperate to get the torturing boots off my feet.  When I checked the time I had been out walking for almost an hour dressed completely as a girl.  Once I had restored the circulation to my tortured feet I was thrilled and exhilarated by what I had just done.   I washed the makeup from my face and returned all my borrowed clothes to their rightful places - leaving just the strap marks from the bra around my chest and the belt marks around my waist as evidence.  My legs were stiff and sore and I had trouble walking for days - I had to blame it on a particularly hard cross-country run at school that week.

Despite the painful experience I continued to venture out fully dressed. 

teather teather
7 Responses Feb 21, 2010

I am glad you enjoyed your first time dressed outside the house, the feeling is wonderful to be dressed.

Yes, very similar to my first experience walking around a few blocks.<br />
However, I was very lucky that my mothers clothes and shoes fitted me just great, its like they where bought just for me. I just loved her boots that she had back then. 4in heels they where. it didn't take me long to feel at ease with 4in after trying her lower heels. Its like I was meant to be a girl all along.<br />
I am so comfortable dressed and in heels, more so than in male clothes. <br />
I feel so restricted in male clothes.<br />
I have tried so hard to be a male but it seems I am not cut out to be one.<br />
I will have a good talk to god next time.

You go girl. That was a really cool, enjoyable story for me. I could feel the tension. Luv Kelly.

Wow, that was hot...I wish I could have been there to walk with you. I would have been a gentleman and treated you like a lady.

that is amazeing wow

Outstanding detail!! That is a five-star-er for sure. Thank you for giving that up to the masses! I'm going to gift you Hon. Standby.........

wow <br />
that is an amazing story!<br />
Thanks for sharing it!