Bubba136

Oooops, Not a girl. But as a guy that is deep into heels: Piece of cake, Mrandy123. Practice, practice, practice. Just put them on and walk around wearing them and get used to the elevation. Those shoes should not be difficult, at all. You're going to win your bet -- as far as the heels go. (Can't speak for what else she has in mind )

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Being mentally comfortable in your own mind is the key to wearing heels in public.

Mrandy123

so, after everyones helpful posts, i started to feel more confident and uped the anti in this bet a little more, i agreed to not just wear heels, but a dress, let my friend put make up on me, do my hair(i have pretty long hair for a guy), i even agreed to shave my legs and let her give me a french manicure. did i get way too overconfident here, or could this actually turn out to be kind of a fun night?

tightsnheels

It could be extreamly fun for both of you. That said I offer two pieces of advice:
Deep carpet is in my experiance more wobbly in the heel.
Shallow chairs and toilets offer differant chalanges to standing up as your geometry is differant. Also in a dress if it is longer watch that you don't plant your foot in the hem before standing!
Go out have fun and keep us informed.
T&H

Bubba136

Careful, she just might have created a monstor because dressing in women's clothing and wearing heels is extremely addictive.....and, who knows, you mightn't ever stop.

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Being mentally comfortable in your own mind is the key to wearing heels in public.

Mrandy123

i must say i am still nervous but also a lot more excited, we changed the heels i am wearing because these seem to go better with the dress:http://www.wetseal.com/catalog/produ...productId=8213

Here is the dress we decided on:http://www.forever21.com/product.asp...9463899&Page=1

at least i dont have to worry about my heels getting caught up in the dress it looks pretty short lol, but this should be interesting day to say the least, i start off at her house to get changed and let her do my hair makeup nails etc, then its off to the mall, followed be dinner, movie, and out to a club after words, so ill probably be out for like 8-10 hours in this outfit, my friend says it will be an interesting perspective to what girls go though every day just to look nice, perhaps more guys should try this at least once.

Bootking

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It's the heel!

Loveshiheels

Both the dress and the shoes are very nice but you may have a small problem with the dress. It,s the way the dress is cut at the front. While It may look good on a female where it shows a bit clea'vage that is not going to work for you. You might be better of finding a dress that will hide the padding for you fake breasts.
Some things you may need to bear in mind when wearing heels for the first time. The yellow courts shoe you have point out to wear. Your feet may slide in them and if you are wearing tights your feet will slide even more. This will make walking in them harder. If you can find a pair with an ankle strap or pair of Mary Janes, this will help solve the problem. If you can find a pair with a round shoe box then you will find that type of shoe more comfortable in the long run.
Payless shops are good for shoes, so I heard since I live in the U.K.

tightsnheels

I agree Payless is a great place for finding shoes. I would suggest a pair of tights/pantyhose (also helps hold umm things in place shall we say.) as a way of avoiding a blister at the back of your heel. If you are not accustomed to wearing them friction blisters are pretty much a given with bare legs. If the shoe fits well then there should be little to no problem with your feet slipping but make sure to fit them at the end of a day after being on your feet for some time so you don't get a pair that's too small.
Deepending on your build the cut of the dress may not be a problem in the chest as I have seen my share of women without much in that area do just fine and seeing as you have not mentioned breast pading I am assuming there will be none. As to its shortness try it on WITH HEELS ON and above all make sure you don't expose yourself when sitting down if it even seems close to exposure find something else. Trust me there is no worse feeling that starting out slightly unsure then having that nagging feeling grow and grow until you are scared beyond reason. Remember just becuse it fits when standing doesn't mean it will when standing up or sitting down.
Just a side note before I stop have you two discussed bathroom arrangements? Typically when dressed enfem (I think I spelled it right, oh well) it is standard practice to use the ladies room however; if you really don't pass that could be a problem. Don't want to be a downer but facts are facts and 8-10 hours out says you're going to have to go.
Good luck and remember have fun and send pictures
T&H

Mrandy123

We went out and bought both the dress and shoes today, they fit well, i tried both on and while short, the dress still fits decently while both sitting and standing. the say is thursday, i am pretty excited. as far as bathroom arrangments, i am going all out during this so i will look as much like a girl as humanly possible, but just to stay safe, we are going to stop back at her house from once or twice throughout the day for bathroom stops. like i said along with the dress and heels, i am also letting her do my hair makeup, shaving all the necessary parts(legs armpits chest), and letting her give me a french manicure and pedacure, so i will be as feminine as possible. I will try to keep you guys updated and thanks for all your help

Mrandy123

I know i said in my previous post that i would be going out all dressed up as a girl thursday, but things got moved around so we moved it up to today and are probably about to leave in ten minutes. im sitting here currently all dressed up(having some trouble typing in this french manicure, my friend tells me if i break a nail she will kill me) and just waiting to leave and i have to admit i am having an excellent time. i am still a little shaky with the heels on but i feel like i will get better as the day goes on, and am looking forward to a fun day, ill let everyone know how it went later tonight, and ill try to post some pictures.