Back when I was very young, i.e. browsing the Eaton’s, Simpson’s, or Sear’s catalogues and when done looking at all of the new toys I was never going to have, I would sooner or later come across the lingerie section.

Great looking women dressed in bras, panties, stockings, garters, girdles etc. My attraction was not limited to simply finding the pics somewhat arousing in many ways, I found myself wanting to know what it might feel like to be dressed like that.

But this was something I would not experience, unfortunately, until quite later in life as in the past 5-6 years. Because in the earlier stages of my life experimenting with things like that just seemed to be taboo—for whatever reasons.

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Fast forward to the 80’s & 90’s and I had the privilege of seeing a group called the Great Imposters, first at a little place in Toronto, called Figaro’s. At first, I thought we would be seeing a group of female singers.

I was proven wrong when the “girls” took the stage. WOW! Was I impressed. The girls were actually guys dressed as women and I can’t think of any celebrity they couldn’t turn themselves into including Bette Midler, Patti Page, Tina Turner, and Cher.

The Great Imposters were awesome to say the least and worth every penny paid, and then some in my opinion. In addition to the adoring comments from the audience, who boiled over with accolades and demands for an encore(s), were the inevitable comments such as, “where do they hide their you know whats?”

Seeing the Great Imposters legitimized, for me anyway, that girls can be boys and boys can be girls in this great old world of ours. In fact, many times throughout my younger life I was told I should have been a girl because of my love for children. Many times, I have wondered if they somehow got my sex mixed up at birth.

These thoughts would occur to me often as I felt like a “Woman Trapped in a Man’s Body” many times throughout my life.

I have always been an admirer in my interpretation of a great pair of legs and none of the Great Imposters gams disappointed. For me, there has always been something very alluring in great legs and how they are dressed. My spouse being no exception to this rule.

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When it comes to moments of intimacy nothing pleases me more than for her to wear a sexy pair of stockings. I simply love the feel of them next to my skin and find the whole experience quite stimulating.

Since admitting to myself and her that I am very much into crossdressing, I mused one evening about what it might be like if we both wore stockings while making out. We opted to give it a shot. What a very sensual and erotic first experience. So enjoyable, I never wanted it to end.

All of which is to say, “There is Something About Legs Dressed in Stockings!”

Samantha

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Samantha James

I am someone who feels like a female trapped in the body of a male or maybe I just have gone a little mad with age, I am not sure which. What I do know is this, I am as comfortable in a Dress, Stockings and Heels as I am in a pair of men's jeans and I have gone to High end Restaurant dressed in a Dress, Stockings and Heels and felt no shame or embarrassment whatsoever.

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Diane Crow
Duchess
Trusted Member
Diane Crow (@dianecrow)
15 days ago

Samantha, I just love your story. Legs Dressed in Stockings should be the name of a novel. Thank you, you’ve made my day.Hugs
Diane

Dorothy Brinson
Member
Dorothy Brinson (@hbrinson)
14 days ago

Samantha, I love your story. I have also felt like I was a woman trapped in a man’s body. I did a boudoir photo shoot several years ago. One of my outfits that I wore was a garter belt and stockings set with matching bra and panties. I have received so many compliments on my legs. Even a few of my female family members told me it was a shame that I have better looking legs then they do. I had a female friend tell me cross dresser seem to always be more beautiful than a lot of natural women… Read more »

Amy Myers
Baroness
Trusted Member
Amy Myers (@amylove2dress)
14 days ago

Thank you from a former Toronto girl for your lovely recollections! My Mum was a big fan of shopping at Eaton’s and I too remember looking through the catalogues, and the lingerie section was a favourite, as I’m sure it was for many.
The feel of stockings, or any kind of hosiery, for that matter is simply wonderful.
It is great that your wife is open enough to accept your dressing, and to have fun with it too.

Victoria StJohn
Active Member
Victoria StJohn (@victoria81)
14 days ago

Samantha, thanks for bringing back memories of those beautiful Eatons and Sears catalogues. I do remember them well. Be safe!

Victoria StJohn
Active Member
Victoria StJohn (@victoria81)
13 days ago
Reply to  Samantha James

I do remember the skywalk, but didn’t have the opportunity to use it but once or twice. Many times, walking or driving below it. The ‘good old days’ they say. Cheers!

T.J. Byron
Duchess
Active Member
T.J. Byron (@t-j-2)
14 days ago

S.J… Loved your article! Nothing more erotic than a great pair of legs ‘ incased” in 100% , nylon stockings! I have many pairs and never ‘ dress ‘ without them. I love OBGs, pretty garter belts. When I go see a drag show , I always Glamour up. I have been told I have” great Legs” and I am very proud of that. Love to shave them and put on a beautiful pair of fully fashioned stockings ( Opera length). Thanks for article…hit me up to chat. At 74, I have been out in public since the 1960’s, in… Read more »

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Jane Borden
Duchess
Member
Jane Borden (@janeborden66)
8 days ago
Reply to  T.J. Byron

What lovely legs-so sexy, a complete turn on xxxjane

Deborah Sullivan
Duchess
Active Member
Deborah Sullivan (@debbiedd)
14 days ago

I was hooked the first time wearing nylons too and has kept me shaving my legs ever since. Wonderful feeling slipping them on after a close shave and then the feet slipping into a snug pair of heels

Deborah Sullivan
Duchess
Active Member
Deborah Sullivan (@debbiedd)
13 days ago
Reply to  Samantha James

oh god yes pointy toe pumps

Lucinda Hawkns
Active Member
Lucinda Hawkns (@dlgeb275)
13 days ago

this so amazing to read. boys will be girls and girls will be boys is a good one. we see real woman dressed in manly cloths every day and nothing is said about it. but when men dress in female cloths its a different story. but we see men dressed up in female cloths and do a play or sing as woman. female cloths are a great fit and look sexy. we get nothing to wear besides pants and shirt. nothing good looking about male clothing BORING. woman get all the sexy clothing to wear. this was a great post… Read more »

Lucinda Hawkns
Active Member
Lucinda Hawkns (@dlgeb275)
13 days ago
Reply to  Samantha James

yes things were different back then. to bad the internet was back then and then us cross dressers would have had a place to go and chat with others. yes back then woman wore dresses and sexy feminine things and men wore 3 p suites. i hear its a taboo to x dress? then why do real woman wear male cloths? if its taboo. true about wearing sneakers with a  gorgeous outfit. to me wearing female clothing as they call it the feel of it and the fit is so amazing. why not wear a bra, the feel of the… Read more »

Maria Girl
Member
Maria Girl (@maria1234)
6 days ago
Reply to  Lucinda Hawkns

Soo true; when dressed as ‘Maria’ it feels so right so why can’t we feel sexy as well

Lucinda Hawkns
Active Member
Lucinda Hawkns (@dlgeb275)
4 days ago
Reply to  Maria Girl

yes why can not we dress up in pretty sexy clothing like real woman should be dressing up in and not this shirt and pants deal as they call blouse and forgot what they call it. but its pants and shirt to me. real woman do not dress pretty no more so why can’t we dress up instead and look pretty instead and they can look nice in pants and shirt. when i dress up i feel more female and sexy and pretty. i feel more human and the way i should be dressed up a female

Rikki Edwards
Duchess
Active Member
Rikki Edwards (@rikkicd)
13 days ago

Hi Samantha, I was struck by how much of your article I have in common with. I too grew up poring over the Sears catalog at the pics of women in bras and body shapers and girdle..in those days it was girdles and stockings that hooked me (I was aroused and and also envious of being able to wear those things). I also saw The Great Imposters, probably in 1979 or 1980 at a place called The Pirate’s Cave, about half an hour from where I live in Newfoundland. I saw them with my first wife…I was enthralled by how… Read more »

Janet williams
Member
Janet williams (@janetcd2143)
12 days ago

love having nylons on and love seeing guys in nylons and thigh high wish I could go out and enjoy being the female I dream of

Kara Sumtymes
Member
Kara Sumtymes (@luv2bdressedup)
8 days ago

I to,,,, of course love to see a GGWoman wearing Stockings ❤️ &,,,, I to,,, can & do Enjoy wearing them myself along with perhaps a garter belt or even a open bottom girdle I to shave as well ever since I been doing this I have always had the thought??? That if,,, any man would even try putting on a pair of Stockings along with a garter belt,,, that’s-it,,, lol they would be,,,, hooked!!! Kara!!!

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