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Starting To Cross-dress

When I was younger I had a fantasy about going around a local town dressed as a woman: I thought I had good legs (still do!) and wanted to see if I could make it convincing. That never happened then - the logistics were too hard and my mum's clothes were too boring...
Now I'm older, I can begin to see the opportunity arising - I'm more mobile, have more money and I now have some opportunities. So I started with my plan. I still haven't put all the pieces together yet, but I will probably post the progress as it happens.
The first thing was shoes - I confess to a bit of a fetish about really high heels. I bid for some ballet boots on e-bay, but luckily I missed out. They would not have been suitable for the long-term project. In the end I got a fantastic pair of 5.5inch black stilettos (with a slight platform sole). I love walking around in them. They really challenge me, but I think I've mastered them now, and my legs look great in them.
Legs next - I'm in a situation where suddenly shaving or waxing my legs would raise questions that I'm not ready for. I thought maybe latex tights, but they're very expensive. I got some cheap wet-look stockings which do at least cover the hair, but they're black and too extreme for day wear. Also, they are a bit short for my legs, so the suspender belt I bought has to work too hard to keep them up - I'm forever adjusting. So I bought a five-pack of cheap 15-denier tights, and put on two pairs to see if that would cover. Not quite, but close. Today I got a pair of nude 120-denier tights. They really do cover the hair - almost totally - but the colour is a bit nasty. Maybe I''ll try some 15-deniers over the top to tone the colour better. For a really sexy look, I got some black fishnet hold-ups - they look fabulous, and over the opaque tights they conceal any last trace of leg hair...
Now the tricky bit. I wanted to look as feminine as possible, so there's an unsightly bulge to be tidied up. I've tried a load of things in the past to pull the bits out of the way: string, cling-wrap, knotted handkerchief. Some were painful, some just too bulky. A chance find on another site got the best idea for me. I took one of my 15-denier tights, which had a run up the leg, and cut off the legs. Then I made a really small hole in the front seam, just where my tackle is. Through that I pull my penis and my scrotum, leaving the testicles behind - they push up into my body with very little persuasion. Next I have a cheap pair of thong panties, which I have tied a small loop in the back (thong) string. I can use that to pull my penis back between my legs and neatly out of sight - the pros call this a gaff.
Next I got a simple stretchy cotton dress (black, long sleeves) to wear. So the gaff goes on, then the opaque tights, then another black thong (I think of the opaque tights as my skin layer) over them, and the stockings. Feels great, and then I put the dress on and I'm getting close to what I want. Problem is, my belly is a bit soft and my waist isn't waspy...
I bought a corset. A cheap one, not a real tight-lace job. It's a struggle to get it on, but once in place I can tighten it up and get a waist, and a flat belly. It also gives me somewhere to put some padding for my upper body. I need to work on that - it's not perfect yet.
For now, that's where I am. I'm wearing it all as described right now as I type. I walk around indoors like this when ever I get a reasonable amount of time to change.
jessicatv99 jessicatv99 41-45, M 4 Responses Apr 4, 2012

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Keep going I swear there's nothing more thrilling and fulfilling the taking those steps. I truly love when I feel pretty and venture out dressed up

Making the plan is so much fun and going over it to tweek it and possibly making it better or riskier, go for it and good luck

I love the way you are planning this. I did something simillar at 41-45, the planning and assembling clothes and makeup to pass as a woman in public.

Sounds like a good plan, keep us posted on how it goes.