Going heeling, cross dressed or not ?

[BOOTED UP]

Hi, I love my boots and I wear them around the house all the time, I have worn my high heel boots outside on lots of occasions,but I feel its better to cross dress when going out in my high heel boots, I don't mind this, in fact I quite enjoy it, but I only pass if my face it covered with a scarf, do any of you feel the same? I feel that nobody notices if its a woman, and I can stay out in them for longer, but still I want to be noticed. Is it unusual that I am comfortable going out dressed as a woman just to wear my boots, when I feel nervous wearing them dressed as a man? When I go out as a man I only wear my low heels maybe 2 or 3 inches under my jeans, but I still want people to see them. HELP.

[Histiletto]

Booted Up, Your conundrum has been a common stage of progression many male heelers find themselves in. Consider everything that you can perceive for the goals you have for your life. How does your perspective/position fit into your program to meet your goals? Wearing heels should be as normal as eating when your hungry. Until enough men come out of their closets or feminine disguises, male heeling will continue to be seen as quirky and men will continue their activities of deceit in order to wear high heels. It's OK to crossdress if you think that is what you need to do in order to wear heels. Let's first make heeling for men as common as it is for women. How does this idea fit into your goal settings?

[Heel-Lover]

Hi booted up, I think the most important thing is simply to do what you feel comfortable with. I am not interested in cross-dressing, but I openly wear skirts,heels. So I am not interested in trying to pass as a woman, but I do put the effort in to try and achieve a balanced look (in my mind anyway). My look would be best described as a feminine lower half and a male top half - I break it mid-way. I sometimes wear stockings (only with skirts), and usually carry a handbag, yet sometimes I sport a beard. I suppose I am mixing the boundaries as most would percieve them. I have found over time that as my confidence grew, my wardrobe grew. (eg. a handbag is very important when you have no pockets because you're wearing a fitted skirt, suspended stockings are more practical than pantyhose). These items are very feminine things, I never saw that evolution coming, but I don't let that worry me. As a contrast I would not be comfortable with my look if I was wearing thigh high boots because they are 'hooker boots' in my mind. I don't like chunky looking heels you can get in the massive sizes as I think they also say 'cross-dresser'. They bring the wrong type of attention. Similarly I have been uncomfortable at times when I have felt I've dressed in too 'sexy' a way. I didn't start the day with that intented image etc, but circumstances etc have led to me to that feeling. High heels are quite a 'sexy' thing as part of an outfit and they need to be balanced - and I feel especially so for a man, since one traditional boundary has already been crossed. The trick I think is to have a classy/classical look, not a modern/trendy, sexy or a slutty look. I like 'my look', feel confident with it, and along with that confidence I find most people accepting of that. The trick is to keep the look balanced so as to not draw the wrong type of attention. I like the attention I get, thats half the fun. Thats half the reason why I get out these and wear heels more and more, and why am a bit of a flirt sometimes and I do like to push that 'sexy' boundary a little know and again - just for fun. But its not easy. Personally I think wearing skinny jeans and knee boots is a good look, pumps are better with a 3/4 length pant. That might be a starting point for you? Once you've been out and about a bit you'll be away. The most important thing is make sure you really like your look, you will have to work on it (it took me ages to piece together stuff to start off), and you'll then be confident. People will accept you when you portray a strong and confident, larger than life image. Show nervousness or signs of weakness and this could be preyed upon by small minded people. Cheers Heel-Lover

[roniheels]

Histiletto and Heel-Lover both have good advice for you. What you feel comfortable wearing in public is the bottom line. I wear 5" stiletto high heels with men's clothing in public and I am comfortable with this look. I too hope to be noticed and I welcome all views, comments, and opinions from those who see me. When I am out-and-about in high heels, I feel comfortable and sometimes forget I am wearing them depending on what I am doing. You need to decide what is most comfortable for you and then enjoy your outings.

[BOOTED UP]

Hi all, thanks for all the comments. I have a couple of outfits that I put together that have the confident look you talk about. These can be worn dressed as a man and hopefully I will wear them out heeling when I build up more confidence in myself. These have slightly shorter jeans, normally I would wear longer jeans to cover the heels while walking and 3 inch block heels. But you are all right they are my boots and I should be able to wear them when and with what I want, I hope I can put these brave words in to action. Booted up.

[Dr. Shoe]

I wouldn't dream of going out cross-dressed!

[Heelster]

Oh heellllll no!! Nothing like being a target for the militant evangelicals. Next thing I would probably hear is "Scream like a Pig" Last person who did something like this ended up at the 'weirdo's of Walmart' website (whatever they call it) and was passed around via email and cellphone for weeks. Don't think they ever got over the comments

[tightsnheels]

I wouldn't dream of going out cross-dressed!

I agree Doc, what would be the point in wearing mad clothes?

Clothes are just intended to keep our privates private so why the big deal?

More often than not my wardrobe is so blended it would take a lot of sifting to separate the mens from the womens and at that the mens wear would be a very small pile. That said though there are some places I just don't wear too feminine an outfit such as, the aforementioned Wal-Mart.

T&H