What's your strangest "crossdresser's envy"?

[Leslie Langford]

Many of us here have admitted to envying girls and women from a young age onwards for what we perceived as being their traditional gender-based "perks" - i.e. the ability to wear what they chose (and when) without necessarily being forced by society to adhere to certain established male/female dress code strictures, being able to be "tomboys" without fear of criticism or being subjected to strange looks, being given a "free pass" to express their innermost emotions as they saw fit, and being given free rein to use all manner of artificial enhancements (make-up, cosmetic surgery, pretty clothes, sexy lingerie etc.) to improve their attractiveness and appearance, while we are generally consigned to dressing in "drab" in more ways than one.

So - given that - what is your strangest example of the type of "crossdresser's envy" that I have described above?

When I was younger, I not only envied girls and women for the items already mentioned, but also priests and Scotsmen (yes, and Prince Charles as well ) for being able to wear, respectively, dress-like cassocks and kilts while otherwise presenting as men, and without anyone ever batting an eye over that.

Anyone else ever have similar off-the-wall thoughts?

[Jaymees22]

I would want to be pretty enough to make men melt and make women envious of me. I'm so shallow. Jaymee

[STACY B]

Back in the Day it was stocking an heels ,, I would see a woman in that an I would stare like I was in a trance ,, I always wanted to know why some woman did an some did not ? CRAZY ,,HUH,,,,

[Barbra P]

It’s quite warm here today (not as HOT as yesterday though) and I’m wearing an above the knee skort and a light cowl-neck print blouse; in male mode I would probably be wearing drab baggy shorts and a T. I love the other things I’m wearing too, makeup, light floral body spray, jewelry (bangles, earrings, and a couple rings), nail polish, strappy sandals, and a wig (short haired bob). I guess one of my envies is a woman’s ability to show off their sexuality – women get to wear clothes that highlight their assets, nice bust, shapely figure, nice legs, etc. There is nothing in a man’s wardrobe that is expressly intended to enhance a man’s sexuality.

I can remember in high school being envious of the girls wearing blouses that were just sheer enough that you could see their bra straps, or make out that they were wearing a lacey slip. They were at that age where their womanly sexuality was beginning to make itself evident, and I so wanted to also be developing breasts and a hourglass figure – fifty some years later and I’m still waiting. What I’d have given to have been able to actually fill out a bra, wear saddle shoes, a full skirt (like a poodle skirt) a semi-sheer blouse, wide belt, pony-tail, and lipstick.

As strange as it might sound, the other thing I feel I missed out on is pregnancy, I would have loved getting pregnant and carrying a baby, not to mention nursing. I was the father of two girls and I was jealous of my Wife while she nursed both of them.

[CynthiaD]

Yes, nursing would be mine. My wife nursed all of our four children, and found it quite a chore when they woke her up at 2:00 AM. I would have given anything to be able to help her out with that. It was my job to put the baby back to sleep though, so I helped where I could.

I would also have liked to help out with the mothering. That is, comforting the children when they were hurt or scared, or just sad about something. Many times I have rushed up to a crying child and said "What's wrong? What can I do?" The response was always the same: "Go get Mommy!"

[Amy Fakley]

girls can write / sing pretty songs and nobody ever questions it. It is not a sign of weakness. Nobody ever says to a girl "you must be gay because why else would you be writing such pretty songs about feelings and stuff?" By the same token, if a female artist wants to "go hard" and do some screamy hard-rockin' stuff, then they're just "a badass chick".

there is a range of expression beyond fashion choices that our society places off limits to males (at least here in the 'States, maybe it's different elsewhere in the world). By the same token, that restriction isn't an issue for most people ... I'm just one of the weird ones it doesn't work for.

God, how I have envied that freedom my whole life, though.

good thread :-)

[kimdl93]

As a child, I didn't have many illusions about what being a woman was really about. My mother was a very hard working farm wife, raising ten kids, feeding farm hands and family, baking, washing, sewing, gardening and when she wasn't busy, doing projects with the church's women's group, or "Ladies Aid" as they used to call it in olden times. She seldom wore make up or jewelry and most of the time she wore a simple sundress around the house.

I would guess it would sound strange that any little boy, observing that fairly Spartan lifestyle, would aspire to help with the cooking, canning and cleaning but I did.

[Krista1985]

I went to Catholic School, and the only thing that comes to mind from back then was jealousy that female students got to wear skirts. There was no short pants option for male students, khakis and slacks only, so on the hot days (no AC in our run down building) the ladies had a huge comfort advantage. Not to mention that they looked real cute in those skirts!

Still to this day in my office, a woman can wear a short skirt and have a bit of exposed leg showing, while (again) short pants of any description are completely off limits to male employees. The lesson I've learned from that is, "A woman can show her legs from the knee-cap down and still be regarded as a professional/good student. A male cannot."

Also, I have never been a big fan of popping off my shirt, even when I was in excellent shape. Men in some social situations are expected to go topless. Shirts vs. skins at basketball practice... Swimming in a pool... Doing anything at the beach... Working on the lawn (I suppose it's optional toplessness in this case)... and possibly other scenarios as well. I always felt uncomfortable in these situations, and envied girls because they were not made to go about topless.

[Kate Simmons]

I kind of "lived" that dream every Sunday Leslie as I was an Acolyte (alter boy) in the church who helped the minister during the service. I got to wear a dress, smock and jewelery in front of the whole congregation and no one batted an eyelash. Doesn't get much better than that my friend.

[calebsmithxd]

I don't think there's anything too off the wall about what I envy about women. I just really like the patterns and wider variety of colors and styles available to women.

I went to Catholic School, and the only thing that comes to mind from back then was jealousy that female students got to wear skirts. There was no short pants option for male students, khakis and slacks only, so on the hot days (no AC in our run down building) the ladies had a huge comfort advantage. Not to mention that they looked real cute in those skirts!

Still to this day in my office, a woman can wear a short skirt and have a bit of exposed leg showing, while (again) short pants of any description are completely off limits to male employees. The lesson I've learned from that is, "A woman can show her legs from the knee-cap down and still be regarded as a professional/good student. A male cannot."

Also, I have never been a big fan of popping off my shirt, even when I was in excellent shape. Men in some social situations are expected to go topless. Shirts vs. skins at basketball practice... Swimming in a pool... Doing anything at the beach... Working on the lawn (I suppose it's optional toplessness in this case)... and possibly other scenarios as well. I always felt uncomfortable in these situations, and envied girls because they were not made to go about topless.

I've always been happy that I don't have to cover my chest when swimming.

[lingerieLiz]

I dated a model who envied men's fabrics while I envied the ability of women to wear bright colors. She talked about the richness of the fabrics men wore.

I have always envied the way women looked and exposed their body from bathing suits to formal gowns. Some of the sexiest looks are a long black pencil shirt and a white blouse just sheer enough to show a beautiful bra underneath. A pretty soft dress with a full skirt that flutters in the wind showing a few inches of pretty lace. AND, a flowing formal strapless gown that shimmers as it glides over your body.

[Marcia Blue]

I envied the girls in school, sitting in study hall, touching up their makeup. Wearing skirts and soft looking blouses.

I always wanted to trade places, just once.

[Beverley Sims]

When I was seventeen I envied the girls hockey team uniform......
A week later I was wearing one and playing in the team, as a girl.
The other team never found out.
The team I played for lost.

[busker]

There is nothing in a man’s wardrobe that is expressly intended to enhance a man’s sexuality.

I suppose we could hope for a renewed interest in the codpiece. The renaissance gals probably got a big bang out of it. I do think that a well dressed man expresses his sexuality that way, not by baring his chest, but in the way he covers it. It is his wardrobe. think about all the guys voted "sexiest man alive" by women and look at the way they dress--very classy. Cary Grant, Sean Connery, Fred Astaire, etc. The sexiest guy wasn't always the best looking guy by any means.. sadly, today, most males dress atrociously, when they do dress.

[Gretchen_To_Be]

When I was in the military there were occasions where we would change from fatigues to dress uniforms, but they were infrequent. There was one school I attended where we wore "Class B" uniforms every day, which is like the full dress uniform without the jacket. There were many female students, and their "Class B" could be trousers or a skirt, with black pumps. The heel height was individual discretion, up to a max of 3", but I think some of the gals pushed this. One in particular wore 4", I was sure of it as only a crosdresser would be. And her skirt seemed to be more tailored, so that it looked more like a pencil skirt than the normal uniform skirt. She was well endowed but further enhanced her assets with a push-up bra, so the uniform shirt looked painted on her. And I swear she wore a better brand of pantyhose than the other female Soldiers, much more sheer (again the CD eye). All in all, the uniform looked completely different--rather sexed up--on her than any other female, but it was just subtle enough for her to get away with it. She was amazingly beautiful, and my strong envy--maybe not so strange--was to be able to wear her uniform.

[Nicola2876]

Quite simple in that clothes designed for women are much nicer than those for men. More variety and more fun. Ok, not that strange I admit. I suppose for me it was always tights/pantyhose. From my earliest memories I always wanted to wear them. They fascinate me. I'm wearing them now and would everyday given the chance

[linda allen]

What's your strangest "crossdresser's envy"?

My wife's ability to have multiple orgasms.

Well, you asked!

[Connie D50]

Leslie
Crossdresser's envy I have it real bad right now not sure why, I look at every movie star or model in a mag. and wish I was her young or old in shape or not. All I think of is all the great cloths I could pick from the heads I could turn.
Connie

[yamicd]

" Some of the sexiest looks are a long black pencil shirt and a white blouse just sheer enough to show a beautiful bra underneath. A pretty soft dress with a full skirt that flutters in the wind showing a few inches of pretty lace. "

It is nice to see that others also love this look. Ever since I was 12 or so this very thing had me secretly wishing I was able to look and feel just like the woman who wore these soft, sexy items. As I grew older I continued sneaking glances of the woman I saw in everyday life, I took note of how the blouses would drape over their bras or slips and would steal glances of the lace hem of a slip whenever I could. Teachers, office ladies, woman out shopping, even the models in catalogs I always loved how woman could look so feminine. Sadly today woman just don't seem to take as much pride in dressing ladylike as they once did.

Dianne

[noeleena]

Hi,

I never envied the other girls at school or church meeting or any where for that matter, because i knew what i was, i sort of wondered why Mum did not dress me like others though in fact she did from birth till cant answer till when, no memory. it was a photo of myself in a lovely cream dress all hand knited. just lovely.

Again i was dressed 1958 -59 for a church end of year do & Mum was there, the whole works, to do a mime, 5 of us,

Clothes really had no interest for me even though i hated boys clothes . though i should have had our clan colours tartan as a Scot, i would well should have worn
Now that would have been great. would have solved my pants issue's, bloody longs hated them ...... its not a issue now of cause.

im well over that issue,

I was in the Millitary Navy so was dressed in uniform & i loved that, so the next would have been the lovely dress wear that our women wore that would have been neat . i still may get one so there you are,

For myself could i pull it off & look right, that would be my disapointment if i looked wrong.yes thats what would get to myself, maybe im a bit scared to try.

...noeleena...

[Karren H]

When I was younger, I not only envied girls and women for the items already mentioned, but also priests and Scotsmen (yes, and Prince Charles as well ) for being able to wear, respectively, dress-like cassocks and kilts while otherwise presenting as men, and without anyone ever batting an eye over that.

Anyone else ever have similar off-the-wall thoughts?

Funny but I was an alter boy in the Episcopal church for years just so I could wear a dress every weekend! lol

[linda allen]

Funny but I was an alter boy in the Episcopal church for years just so I could wear a dress every weekend! lol

"Alter boy" ? A slip of the tongue (fingers), perhaps ?

Sitting here in a wig, forms, padded panties, skirt and blouse, I guess I am an "alter boy" as well. Maybe an "altered boy"!

[kimdl93]

Lutherans didn't have alter boys...guess I missed out on the upside I can to such religious rituals!

[Briana90802]

As a teen I was a lifeguard, I had to sit and watch girls all day long and I remember wanting breasts so badly so that when I wore a bathing suit it would fit properly. *sigh*

[Stephanie47]

When I was a teenager messing with my mother's slips and shapewear there was two 'ladies' stores in the neighborhood. There was mannequins in the window adorned in undergarments. I wished I could get the nerve to buy and wear some of them, especially a white all in one body briefer. Still to this day I love seeing old advertisements from magazines of the day of women wearing slips and shapewear.