Mar 01 2010
Are women’s clothes really more uncomfortable than mens? Do you think I can win this bet?
Some women at work were complaining that women’s clothes are too uncomfortable compared to men’s and I said they were wrong so we have made a bet. One of my co-workers has a birthday party soon and it is a costume party. They have bet me $100 that I will not dare to go to the party dressed in women’s clothes, to win the bet I would have to stay completely in costume all night and it would have to include a dress, pantyhose, high heels, a wig, fake nails, make up and shaved legs. They will get all my clothes and give me a makeover if I go through with it. They think I will find the clothes and shoes too uncomfortable but I think I can get through it’s only one night after all and the money would be good! So women can you give me some advice, what will I find uncomfortable and how is it best to walk in high heels? It is going to be a laugh but to have fun I want to prove them totally wrong and make it a really brilliant costume because they don’t think I will go through with it!
some woman’s clothing is uncomfortable, there’s no getting around that. Sometimes it is necessary and preferable to wear things that are inconvenient, uncomfortable, or impractical so that you look good. It is the trend these days for a girl to dress …well… like a man really, people don’t care much about how they look and just dress sloppy.
but that’s my rant I guess.
shaving your legs - well I don’t know how it is for a man but do not shave against the grain and do not shave the same spot over and over again. If you can’t get it smooth shave to the side, not straight up. Otherwise you will get a razor burn and it will hurt.
I should suppose the same rules for shaving your face apply.
Wear a skirt that hits your legs just above the knees, not shorter. Really a skirt isn’t uncomfortable at all, wouldn’t worry about it too much.
Don’t buy cheap pantyhose, don’t buy any that say "100% nylon". I don’t even know why companies even make those things, they’re what cause people to say pantyhose are bad.
I would suggest Leggs Sheer Energy with a control top, make sure the color is one close to your own skin color. Make sure they’re in the correct size, there is a size chart on the back of the box and you should buy the correct one for your height and weight.
…I guess those measurements are for women but - well it should be close enough.
Leggs Sheer Energy are tighter than most pantyhose and are stronger and more durable, the control top is a tighter portion in the panty that will help a lot.
Definitely get two pairs just in case, if you accidentally tear them, run off and replace them. Your friends will probably laugh if they find out.
Look at this video on how to put on pantyhose - be a little more careful than this girl and sit down while you’re putting them on.
http://www.youtube.com/watch?v=LQDszavSSmk
I don’t know what you’re wearing under those pantyhose but either wear women’s cotton panties or men’s briefs.
High heels should be a sensible height, don’t get really high pump stilettos because you won’t be able to walk in them. Get a 2 or 3 inch heel with a blocky heel, not a spike stiletto. It really shouldn’t be too hard to walk in them if they aren’t too high.
Hope you win your bet - ha I would see if you could get them to put more money down because you can do this easy.
And be careful not to get too comfortable, I have a feeling you might just like it 
on 02 Mar 2010 at 4:46 am
You will have hell, trust me all of that will be horror the first 5 minutes.
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on 02 Mar 2010 at 5:17 am
lol do it! no you will probably really like the dress, just make sure that everything is made out of cotton. good luck shopping for the stuff!
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on 02 Mar 2010 at 5:24 am
Mwahahahahaha Bout time a guy has to go through the pain!!!
MWAHAHAHAHAHAHA! ! ! ! !! ! ! ! >=)
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on 02 Mar 2010 at 6:03 am
The heels will kill you. They are usually pretty uncomfortable. Wigs are sometimes itchy, but not all. A dress will be fine, pantyhose and make-up are okay. The fake nails will get annoying. If your going to wear a bra (you didn’t mention it, and I don’t think you would but just saying.) then it will be verrrry annoying, and uncomfortable sometimes. I would get strappy heels so they don’t rub you ankles and toes as much and get shorter fake nails. Also, if your going to wear mascara, don’t get the waterproof kind because you will have a hard time getting that off. (;
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on 02 Mar 2010 at 6:21 am
The heels will be the most uncomfortable we only wear them cuz they look good but they hurt after the first five minutes and dresses are ok but still kinda scratchy and shifts out of place and if you shave your legs are never going to grow the same again trust me, you will probably have the worst night of your life. And no matter how you walk the heels are going to hurt. Good luck. ; D
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on 02 Mar 2010 at 6:53 am
Have fun have a horrible time with that….
but sense your a guy…… sucks to be you 
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though i find heels comfy .. they feel fine on me
on 02 Mar 2010 at 7:09 am
Hello!
this is coming from a male. I crossdress on occasion. I feel woman’s clothing is far more comfortable then men’s. I do shave my legs all the time and I still wear pantyhose daily under my pants to work. as for the heels I bought a pair of American Eagle from Payless shoes in a 4 " heel. they have a fat heel and it gives you some better support. to be truthfully honest I so wish it was accepting for men to wear as they choose and desire. if Woman can wear men’s clothing and nothing is done then a male should be able to wear woman’s clothing with same results. enjoy the night of dressing that way. I was out dressed as a woman on a Halloween night 15 yrs ago a mirror image of my G/F back then. I had a ball walking about she even made me use the woman’s room.
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on 02 Mar 2010 at 7:50 am
some woman’s clothing is uncomfortable, there’s no getting around that. Sometimes it is necessary and preferable to wear things that are inconvenient, uncomfortable, or impractical so that you look good. It is the trend these days for a girl to dress …well… like a man really, people don’t care much about how they look and just dress sloppy.
but that’s my rant I guess.
shaving your legs - well I don’t know how it is for a man but do not shave against the grain and do not shave the same spot over and over again. If you can’t get it smooth shave to the side, not straight up. Otherwise you will get a razor burn and it will hurt.
I should suppose the same rules for shaving your face apply.
Wear a skirt that hits your legs just above the knees, not shorter. Really a skirt isn’t uncomfortable at all, wouldn’t worry about it too much.
Don’t buy cheap pantyhose, don’t buy any that say "100% nylon". I don’t even know why companies even make those things, they’re what cause people to say pantyhose are bad.
I would suggest Leggs Sheer Energy with a control top, make sure the color is one close to your own skin color. Make sure they’re in the correct size, there is a size chart on the back of the box and you should buy the correct one for your height and weight.
…I guess those measurements are for women but - well it should be close enough.
Leggs Sheer Energy are tighter than most pantyhose and are stronger and more durable, the control top is a tighter portion in the panty that will help a lot.
Definitely get two pairs just in case, if you accidentally tear them, run off and replace them. Your friends will probably laugh if they find out.
Look at this video on how to put on pantyhose - be a little more careful than this girl and sit down while you’re putting them on.
http://www.youtube.com/watch?v=LQDszavSSmk
I don’t know what you’re wearing under those pantyhose but either wear women’s cotton panties or men’s briefs.
High heels should be a sensible height, don’t get really high pump stilettos because you won’t be able to walk in them. Get a 2 or 3 inch heel with a blocky heel, not a spike stiletto. It really shouldn’t be too hard to walk in them if they aren’t too high.
Hope you win your bet - ha I would see if you could get them to put more money down because you can do this easy.
And be careful not to get too comfortable, I have a feeling you might just like it
References :