Starting To Cross-dress 2 - Realisation Of A Dream

In my post earlier I talked about my fantasy of walking around town dressed as a woman (I'm not, in case it's not obvious!)
Today I did it  - the culmination of a couple of months of planning and waiting for an opportunity.
The costume has changed a little from the earlier post: the best bit is the tight pencil skirt I got on-line - tight linen so not much room to stride out, and quite subtle (well, I thought so...). I also went for plain black tights over the top of the layers of nudes, rather than fishnets, so as not too attract too much attention. I added a bra, lightly padded to make proportionate breast shapes, and a really long dark wig. I also bought some basic make-up items and some false nails.

This morning I dressed up and made up, then stole out to the car. I really wanted to avoid getting spotted in the immediate area - too many people might know me and cause problems. I drove to small town a few miles away: in the car I was pretty confident, although I had to take my shoes off - the heels are way too high to control the car properly! I drove really carefully - it would not have been a good time to have an accident or get a ticket.
My plan was to pop into a particular shop I had never been in, looking for a certain item (you'll forgive the lack of specifics - I'm not out yet...). I parked up in a public parking lot and walked back through the town to the shop. It was a longer walk than I had expected, and you cannot believe how much more difficult high heels are in the real world or rough paving and tricky slopes! The other really freaky thing was the men is passing cars and trucks checking me out, especially the ones approaching from behind and then craning around to get a look. I hope I didn't scare any of them! I got no insults, but no compliments either.

The store I was heading for was run by senior ladies. I realised I would have to speak to them, but in the last few days I''ve developed a really bad sore throat, so I explained that it was doing funny things to my voice and used a slightly gravelly whisper. I don't know what they thought - they were certainly just courteous and referred to me as madam and 'this lady' ,although one described the voice as sexy! It seems like I passed reasonably well. Anyway, it turned out that they didn't have what I wanted (at least not for a price I wanted to pay) so that avoided some possibly trickyness (like finding an ATM, or trying to use a card with a man's name on it). I walked back through the town to the car, checking my reflection in windows. I was getting very hot under the wig, and had beads of sweat forming. Into the car and aircon on - phew!

I drove a short way to another town where I knew a nice spot to try and get a photo of myself. It was a bit tricky here too: the path to the spot I wanted was pretty rough and unpaved, so I nearly busted my ankle getting there. Not so many people saw me here, but in a way that was the hope - I wasn't sure I pass close examination any more, with the heat ruining the make up.

And that's about it - I'm back at my desk posting the story. Maybe I'll do it again some day...
jessicatv99 jessicatv99
41-45, M
13 Responses May 22, 2012

You had a good day out without any bad surprises, so why not try it again? You're clearly getting getting your "look" right.

I am confident that you will do it again and when you do please be sure to post the experience. I love your confidence (and daring). The best that I have done so far has been to purchase a cup of coffee at a drive -up. Minimal interaction but there was some and the feeling was wonderful. Thanks for the post.

i wish i could do something like this, but with my girlfriend :3 i would be sooooo lucky if she would go out with me

so you had a good day you must do it again

Sounds like you enjoyed yourself
i am growing my haor so as to not get hot or worry about the wind.

way to go gurl. it gets easier every time, and i do it with out make up and a wig.

Sunds as though you are having the time of your life. I would be to if I could only find the time to go out as well.

Good for you. I remember my first time, I was really scared. Wait until you use the ladies restroom in a crowded restaurant, hotel, bar or store. Wow, to be able to walk in the ladies restroom, be accepted and the ladies just smile at you. The guys staring at you are not reading you, they are checking you out. The guys are accepting you as a women. That part took a while for me to understand and accept. Good going girl.

It is fascinating to read about your exploits. Keep up the good work.

Way to go girl! So very courageous to get out in public dressed up.

AT my first outing i was scared that someone would know know me ,but every time i went out i became more confident with myself and now i dress up and go out . I enjoy every outing i go on

Practice makes perfect, the more times you go the easier it will be and the more comfortable you will become.<br />
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If you don't mind a little advice, become a people watcher (do it without being obvious) watch the women our age, try to duplicate as many of their styles, moves and actions as you can into your own feminine identity. Being passable is one thing and that is good, but when we don't blend in and draw unnecessary attention to ourselves that is when it gets dangerous.<br />
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Anyway keep going, be strong, you have an interesting journey ahead of you.<br />
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Stay safe, Liza

That was an accomplishment, and it took courage. give yourself a hug. You are really brave!