Lawrence

I didn't know ab out the hair handicap.  Sorry.  I was just thinking how nice it would be to look the part.  If you only want to dress as a woman then go for it.  I would prefer to be mistaken for a woman and look the part.

If I were you (and I know I'm not) I woukd sure be growing my hair out.  If I am going to go about dressed in a skirt or dress I want to look the part.  That's just me though.

When I wear heels My feet do not hurt.  In fact my feet feel more comfortible in heels then flats.  However I have a pair of pink strappy heels and my little toe ( right side) does not fit behind the strap like it is supposed to and that causes preasure on it and after a short while does begin to hurt.

Wish I had the courage to go any time I wanted in heels.  I'd be getting a divorce thrown at me if I did though.

You go man!  You look quite nice and moderately conservative.  I prefer shorter skirts and dresses but what ever floats your boat!!

If you like heels and have the courage to wear them then for sure rock out in them.  Just go clicking down the way all you want.  Don't hide them under pant legs.  Show them off.  Thats what heells are supposed to do.

While I agree if your waist is larger then your hips it would look awful if you wore a skirt, it is still a matter of opinion and if you want to go ahead.  Myself, being only a bit lg in the waist and def. not larger then my hips look as good as a 70 yr old man can look in a skirt or dress.  And of course heels.  I prefer tights as well.  Not that my legs are that bad but just the airey feel of them is a sensation I love.

18 hours ago, pumpcat said:

I think people should wear whatever they like. Our day would go a lot smoother if we are comfortable in the clothes we wear. 

 

I like dresses with heels and boots. If I wear a skirt,  I'll put a belt with a huge buckle with it. I find it makes my lower body a lot longer. 

 

I know how the guys feel. I have a pair of 70s mend platform shoes that I would like to wear,  but I might be shunned wearing men's shoes as a girl. I'll send a pic soon, they look really cool. 

You go girl and wear those shoes.  As a girl no one will say a thing you can bet on it.  I just wish it were the same for us men.  The looks and coments are often and not very pleasant.  I sure wish it didn't have to be that way.

I sure wish I could have been there.  I'd have stopped and chatted a bit just to see where he was comming from.  Maybe sat down and had lunch with him and got to know him a bit.  For sure discussed our mutual dress preferences.  To bad the boots were flat.  Looks so much more aluring in heels.  Patterned hose wow he was brave!!  Just guessing by your discription it must have been a mini skirt?  Do you remember any of the colors of things he was wearing?  Did the outfit all match?  Just wondering.

2 hours ago, Chorlini said:

I didn't want to open a separate topic for it but for the first time ever I saw a guy in a skirt today. Really short one too, with black patterned pantyhose and flat pair of boots. I originally thought it was a chunky girl as he had long hair then I passed by close and noticed facial hair. It's not something I would like to do myself but I admired his guts in doing so. Not the least because it was quite chilly.

2 hours ago, Chorlini said:

I didn't want to open a separate topic for it but for the first time ever I saw a guy in a skirt today. Really short one too, with black patterned pantyhose and flat pair of boots. I originally thought it was a chunky girl as he had long hair then I passed by close and noticed facial hair. It's not something I would like to do myself but I admired his guts in doing so. Not the least because it was quite chilly.

while I am not a pro in those 4, 5, and higher heels I absolutely love my 3" heels and find them so very much more comfortible then mens shoes.  I started wearing them for the sexy nature of men in heels but quickly came to love them just as shoes.  I underdress 24\7 so yes I wear hose with my heels.  I also wear the other undergarments as well.  Love the nice snug feel of them on me.  YES wearing dresses is absolutely the next step.  I love the open airey feeling of them as opposed to the constricting properties of pants.  You are so right there are so many styles, colors and paterns, and so many combinations.  Just a dress, and a blouse and skirt.  I often, when wearing a dress. wear under it a nice full petticoat.  It really brings the fem out in this heel wearing guy!!!  Hose also.  So many colers to chose from and now the patterned variety.  I love all of them.

While I am not a pro in those 4, 5, and higher heels I absolutely love my 3" heels and find them so very much more comfortible then mens shoes.  I started wearing them for the sexy nature of men in heels but quickly came to love them just as shoes.  I underdress 24\7 so yes I wear hose with my heels.  I also wear the other undergarments as well.  Love the nice snug feel of them on me.  YES wearing dresses is absolutely the next step.  I love the open airey feeling of them as opposed to the constricting properties of pants.  You are so right there are so many styles, colors and paterns, and so many combinations.  Just a dress, and a blouse and skirt.  I often, when wearing a dress. wear under it a nice full petticoat.  It really brings the fem out in this heel wearing guy!!!  Hose also.  So many colers to chose from and now the patterned variety.  I love all of them.

If she won't budge then try looking on line for someone with your likes in your area and see about hanging out with them.  Just wearing heels is not running around and being the same sex would not be running around on her at all as long as it it is just hanging out in heels.  I'd love to find someone in my area to do that with.

I am so with you there.  Womens clothes are so much more comphie, more colorful, and feel so good when I am in them.  I stay in girdle, tights and panties under my ( have to wear) mens stuff 24/7.

You are so right.  I go for heels big time though I only have a few, but I progressed to skirts, dresses and all the undertiings as well.  Panties are much more comphy then tighty whities or boxers, thigh high stockings with garter and tights are way comfortable.  Not only that there is such a big selection of colors and styles.  I love them all.

You may want to look into womens sheer or opaque claf length nylons.  They are very airy and seem to wick the sweat away leaving your feet dry.  I hope everything works out for you and you get to have the collections.  Keep me posted ok?

I'm so very sorry to hear about your wife.  I'm a late commer to this story and though I did not get to follow it I was rooting for her recovery.  I hope that time will take the edge off the sorrow you must be feeling.

I buy my heels at Payless and have been in there dressed male and have been in there dressed fem and both times tried on heels before I bought them.  What a thrilling experience.

I feel very feminine in heels and especially when in a tight panty girdle and everything tucked in and over that a nice brightly colored pair of Silkie tights and a sexy pair of panties.  Right now I'm in pale pink panty girdle, Chartruse tights and a baige with black lace trimmed bikini panties.

Well as a guy who wears heels I am happy to have found you guys and am lookng forward to getting to know yoou all and hearing your stories as well a sharing mine.  I'm sort of new to heels but even so I have found a very comfortable pair. They are black with 3" heels closed toe, rounded front, no straps and I love them.  I thought my first experience with heels would be like being a stumble bum, however I must have lucked out or the lady at the store just knew the righ thing to do cause these heels are so easy to walk in that I was instantly hooked on heels.  I now prefer heels to normal mens shoes and go in them every chance I get.  If you want to know ore about mejust drop me a line and I will do my best to answer all your questions