Out In The Streets (part 1)

After gradually preparing myself over a period of time I was able to take the plung and actaully dress as a woman from head to foot and go out into the streets and see what would happen.  I had first started with a bit of make-up and lipstick, then wearing womens clothes around the house. Later I bought bottom and hip padding and breast forms, wigs and some girlie style glasses. I had by then shaved my bodyhair, legs, chest, arms  and eventually under arms as well, (this was pretty exciting). I also bought a body shaper to pinch in my waist a little to give me a more womanly figure. I invested in some earings, bangles and some costume jewellery and lots of make up.

I bought some sexy high heeled boots, some other high heeled shoes, black panty hose, stockings and a suspender belt. I was too chicken to come out at home so I chose to give it  a go in Amsterdam whilst on holiday. I was extremely nervous, but thought at least it would not be he next door neighbour exposing me if I was 'clocked' on the streets. I spend ages preparing and all the clothes I had taken were piled on the hotel bed like something out of a film. Eventually, after about two hours I was ready. Make up with dark red lipstick, wet look top and leggings, patent leather high heealed boots and a mid thigh leather skirt. My heart was beating like a maniac, and cold sweat was making an imaginary appearance. I was finding it hard to swallow, and was smoking to practice my woman's style, of holding drawing and exhaling. I do love the look of lipstick on a pure white filter, and it did make me feel so much more confident. With rings, earrings, necklaces, and bangles a rattling, heels clacking across the polished marble hotel lobby, trying not to catch the eye of the desk clerk just in case I was recognised as the guy who had booked in a few hours before. I set off on my adventure, to walk the streets, dressed as me, as I had never been before.   

As I left the hotel as luck would have it, I saw someone from home walking towards me in the street. I was stunned, surely they would recognise me...?

mentholgal mentholgal
51-55, M
1 Response Feb 22, 2010

Very brave of you! Did you find it easy to walk in high heels? It takes a bit of practice and I found I had to start with 2 inch heels. I can manage with 4 inch heels now, just about! About the "little body shaper", you really should go for a tight lacing well boned under bust corset; it will give you a fabulous waist, accentuate your hips and give you a good posture as well as controlling the way you move.