Love telling Women I miss seeing them in Dresses ! They usually offer me one to wear

[Robbiegirl]

I adore women ! They are so fun and insightful !

Have you ever teased some Gal pals about not wearing dresses enough ? It usually causes a very fun discussion !

They are usually so funny asking if you have tried spending a day in a dress and heels and offering to let you borrow one.

It is up to you how you answer but when I relate my experiences of having to play Girl parts in plays at my all boy school they can't
get enough fun details ! LOL wanting to know exactly what i wore, how I felt in it and how good I was walking in heels.

Anyone else have fun experiences flirting with Gals but not telling about your crossdressing

[Linda E. Woodworth]

Sorry Girl but I wouldn't be caught dead bringing this up with any of the women in the office.

They filed harassment charges against an intern who showed up every day in dress/skirt, hose and heels. They dress "frumpy" and she was gorgeous!

I can't see any way for this to end except BAD.

[ronny0]

Sorry Girl but I wouldn't be caught dead bringing this up with any of the women in the office.

They filed harassment charges against an intern who showed up every day in dress/skirt, hose and heels. They dress "frumpy" and she was gorgeous!

I can't see any way for this to end except BAD.

Sad to say, that's life now days.....
When I am out (in drab) I pay more attention to those that wear a dress or 'dress up'.
Few and far between, but they are still out there.
Though seeing a woman 'all dolled up' in a grocery store most people keep a keen eye on her.

[NancySue]

In today’s world, as much as I’d like to, I’d never say anything to any woman about what she wears. I agree, so many dress frumpy...no makeup, etc. which makes going out difficult. Why? Because I wear all those things they don’t...heels, hose, makeup, skirts, dresses, etc. Sadly, I fear, the age of even sincere compliments is fading. I do, occasionally, suggest my supportive wife wear a skirt or dress. I can’t remember the last time she wore a skirt or dress. I have more than she does. She’s also ditched hose, heels, underwires, slips...full and half. Sad. I try to share with her how comfortable women’s clothes are...and she agrees, but, so far..nothing’s changed.😔

[Stephanie47]

My across the street neighbor quipped not so long ago that she does not own a single dress (I believe her) and told me I should try wearing a dress. I wonder if she saw me leaving the house en femme when my wife was visiting a cousin in the southwest?

Linda (#2), I really don't know why women would file a complaint against any woman wearing a dress and heels or skirt/blouse other than it may have created a "hostile work environment due to guy drooling all over their desks.

The women in the office where I worked before retirement dressed way too casual. Our office dealt with professional business men and women and their representatives (CPA's, attorneys, etc). Some were so casual as to wear flip flops, capri pants and almost beach attire. Sweat suits. When the annual "Walk in Her Shoes" fund raiser parade of guys in heels was occurring at lunch time they were all down on the street trying to guess if any guys were cross dressers based on how easily they walked in heels.

I wonder sometimes if many women would welcome a compliment on how they look from a guy. I'm not talking about leering. Just plain old acknowledge she looks attractively attired. I'd never compliment any women in the work place if she was showing a lot of cleavage which seems to be the thing to do these days.

My wife recently had abdominal surgery and is wearing dresses again. Nice. She does like a compliment.

[Micki_Finn]

A man telling a woman what she should wear is basically the height of misogyny. Glad you hang out with women in their 80s who think this is cute, but you’re in for a world of hurt from modern women.

[kimdl93]

I make it a point of NOT suggesting, implying or otherwise telling a woman or anyone else what to wear. Why do that?

Putting that aside, I don’t have any nostalgia for those pre-pants days. There’s no doubt in my mind that my mother’s generation felt justifiably liberated when slacks and pant suits became acceptable attire. Makes perfect sense to me.

I see lots of women wearing skirts and dresses when the occasion merits it. And I wear skirts and dresses when the occasion merits it. Otherwise, I’m just as happy with jeans, shorts, etc.

[Micki_Finn]

You need to ask yourself why you care about what women wear. Are you aware that by attempting to dictate what women wear you’re sexualizing them? No, you’re not telling them how to look better, you’re telling them that they need to do what you tell them in order to make themselves more attractive to you. How would you feel if women constantly came up to you and said “You should go to the gym more and get hair plugs. Being bald and fat is frumpy.”?

[char GG]

You need to ask yourself why you care about what women wear. Are you aware that by attempting to dictate what women wear you’re sexualizing them? No, you’re not telling them how to look better, you’re telling them that they need to do what you tell them in order to make themselves more attractive to you. How would you feel if women constantly came up to you and said “You should go to the gym more and get hair plugs. Being bald and fat is frumpy.”?

I also wonder why anyone would care what women wear.

Women usually dress for occasions, not to drive around, drive through fast food restaurants, grocery or
mall shopping, or walk in a park. Either they have a job that calls for a dress code a bit fancier than a uniform, dining at nice restaurants, go to clubs, symphonies/plays, weddings/fancy dances, or cruise ship events. I work at a concert venue and believe me, the women dress to the nines there. (However, they do not dress up for the hockey games). You will see women dressed up at events that call for dressing up. So don't expect to see women doing mundane things in a dress, heels, and (ugh.. hose!!:eek:) unless they are running an errand on the way home from work.

Just an observation, but I rarely see men on the street in suits anymore. I wouldn't complain about it, why should they dress up to go to a store? However, they do dress up at the same venues that I mentioned that women dress up for. I am assuming that men dress for the occasion also.

[Joyce Swindell]

I think that the same conversation could start with a "You look very nice today! Special occasion?"

Harmless observation, positive statement and shows intrest in the individuals life.

Not an icebreaker to someone you haven't spoken with before but a familiar co-worker I think would be fine and not lead you into political demise.

[Confucius]

A few years back I had an experience at work. One woman, who always dress well for the office was telling a younger woman that she should wear a dress to work occasionally. Well, the younger woman never wore a dress to work. She didn't even own a dress. Her response was that she'd wear a dress to work when Confucius does. This brought some laughter to the office. There was some people who encouraged me to do it, just to force the younger woman to fulfill her comment. My response was that I found the offer interesting, but I was afraid our boss (a female) would fire me for doing it. Just then our boss walks in and says she wouldn't fire me, and in fact she thought it was a good idea. For the next few days a hot topic at work was, will Confucius wear a dress to work. Yes, it sounds like a golden opportunity, however I didn't go through with it. I was afraid that it would humiliate me for the rest of my life. I regret that decision today.

[Tracii G]

Pushing for equal rights of the sexes has kind of changed the picture hasn't it?
I'm all for people being treated equally no one gender is any better than the other.
Of course some women like to be told how attractive they are but not by a total stranger.All women are not the same so you are taking a big risk by playing that game.
Might work on a few but there is a good chance you will find one that will mess you up.
I know a man in his 70s that is incarcerated at the moment because he thought he was being cute with a woman and he was arrested for stalking.
I just leave them alone because they are too much trouble.

[giuseppina]

Sorry, Robbie, I agree with most of the posters that this is asking for trouble with a Capital T. Making this comment at the workplace is asking for termination for cause. Where I live, that means no unemployment benefits.

[Jodie_Lynn]

Where I work, which is mostly a warehouse type environment, most of the women wear jeans/pants and tees/tops. Even the women who work in the office follow this pattern. But, there is one young lady who is 'out of the norm'. She wears skirts & blouses, dresses, and skirt suits. She also owns a huge selection of heels, boots, wedges and sandals. Her make up is minimal, but fantastically enhances her beauty. Occasionally, she will wear pants or trousers, never jeans. She has a great eye for style, and she always makes her outfits look great.

And if you could hear the snide comments from both women AND men, about her fashion choices, you'd be appalled. As for me, I'm dying to ask her where she shops, or compliment her on her style, but I am not 'out' at work, since it is a bastion of conservatism, and I'm a Temp worker.


As to the OP, I'm happy that they have such a rich fantasy life in which to indulge their peccadillos.

[Kendra Sue]

I love dresses

- - - Updated - - -

Would love to wear a dress and heels at work

[Charlyne]

Hey Robbiegirl, You are right on! I love women too! A light hearted way of talking about cross dressing is fun.. I love it. Yes I have made up reasons to dress. Such as I need to dress up on a dare, but need a photographer. Have made for some real fun times,

[Alice Torn]

I am always a stranger, and when i see a lady with beautiful long hair, or in a beautiful dress, I often comment to them how nice they look. usually they are not offended, and say thank you. I am deeply saddened at how our American society is becoming so scary, and we are becoming zombies, who must stay silent, It reminds me of the old British television series with Patrick Magoohan, "The Prisoner". Thought police is a reality suppression of free speech and thought. We live in a new dark age.

[Tracii G]

I'm sad that we just can't be nice to each other anymore. I would love to be able to compliment guys or girls if they are looking fantastic.
At least I can spot a radical feminist and just stay away from them and stay out of trouble.
Its the small minority that seem to scream the loudest and demand everyone conform to them.

[docrobbysherry]

I would never comment on a stranger's clothing. Even with GG's I know I don't comment more to say, "Nice hair do", "Cute skirt", "nice shoes", etc. :straightface:

Besides I'm WAY more interested in wearing women's things than in talking about them. Except on here!:tongueout

When I see a woman or T wearing clothes or a look I find attractive? I'll see what stands out for me & try to copy her!:daydreaming:

No conversation necessary!:battingeyelashes:

[Michelle Crossfire]

I am in agreement with most posts on here. I have learned that women are simply too much trouble to deal with sometimes and it simply is not worth it. Other than my wife, who is always fishing for compliments, I do not compliment other women out loud. I might think something to myself, but that is it, and even sometimes, I might mention to my wife that she is wearing something that I might, or even her, might like.

[Kendra Sue]

Love telling women they look good because I envy the choices they have

[Teresa]

Robbie,
I let them try the banter on me but it could be dangerous ground if you pick the wrong GG to have fun with .

Just to relate to a story , I was trying on a lovely evening dress and the SA was helping me , in fact she lined up all the available colours in the dress style . I finally picked two out of the six choices , She then said , " Well you've got the dress so how about going out for a drink ?" I replied, " only if you buy one of these !" She replied , " No I'm strictly a trouser girl , besides I've not got your legs !" Yes we did exchange phone numbers !

[susan54]

I work with women who mainly dress very smartly, including skirts, dresses and sheer tights with heels. There is even one woman who never wears any form of trousers. I also have women friends who take huge pleasure in looking good in a dress without any special occasion involved.

As I spend almost all the time I am not at work in a dress, going to work in one would be the only way to increase my dress wearing. One off the pleasures of this would be the feedback on my outfit from women colleagues. I can get this on a Facebook page that is closed to all but those who have done a certain colour/style consultation. There are 500+ women on it and I am the only man (they know I am a crossdresser and are very supportive). I have been known to post pictures of my outfits there but never on any crossdressing site.

I am careful about making comments about outfits to women at work, and on one occasion I felt I had been inappropriate in telling one women how well dressed she was. I apologised and it turned out she was far from upset but I love women in a good way and would hate to be perceived as some creepy type. I am occasionally included in banter about dresses or skirts but probably just because I am the only male in the group - they say they are avoiding being sexist by including me.

I am genuinely unsure how much of my enjoyment about seeing a women in a stunning dress is appreciation of the outfit and how much is what you might call heterosexually derived - probably a lot of both. But I also appreciate women in great outfits where the women herself is not particularly attractive to me. The woman who is always in dresses or skirts wears colours that are spectacularly wrong for her but I do not feel I can intervene even though she is quite a close friend.

[Linda E. Woodworth]

OK Girls, here goes.

Stephanie, I was given the distinct impression that the complaint was filed against the intern because she made all the other women look bad and the other women didn't like the male attention the intern was getting. It came across loud and clear that they were jealous of her looks and the attention she received.

I did see this intern and she was gorgeous!

When ever I was at the home office I was always dressed in a coat and tie. That was "my" uniform. I was dressed better than 99% of the guys and received some very nice compliments from some of the women in the office.

Lastly, if I see a woman who is especially attractive I'll compliment her on her appearance. Years ago I mentioned to my wife how nice a woman looked. My wife told me to not tell her, but compliment the woman as she had put a lot of effort into her appearance. I've since done so on numerous occasions and have never had any negative feedback.

[alwayshave]

Robbiegirl, I have told women that I like their dress, but I am careful of the circumstances. At my Office there is one women, who grew up in Europe and she wears dresses everyday and has impeccable taste. Never said a word, because I don't want it to be misconstrued. I never say anything to young women, because I don't want them to think I am hitting on them. To women my age (50s), I will comment as usually they will take an affirmative comment without misconstruing its meaning as younger women will.

[Alice Torn]

As a 65 year old loner bachelor, with unbearable loneliness at times, i may be too forward with compliments, and considered creepy, but it is tough never having a companion, when all around me are couples.

[Jenny22]

My compliments are to women who have pretty nails, or a lovely top, usually while waiting in the cashier line. They always say thank you, with a smile.

[Jodie_Lynn]

As a 65 year old loner bachelor, with unbearable loneliness at times, i may be too forward with compliments, and considered creepy, but it is tough never having a companion, when all around me are couples.

With respect, at your age, you are allowed to get away with compliments that a younger male (?) would be chastised for. It's one of the perks of being older, as long as you aren't creepy in other ways. :)

At 57, I will often use the words "hun" or 'dear' when speaking with cashiers that I am familiar with, when I am in drab.

Sometimes, when at the convenience store, if I notice that a woman is behind me and is only getting a coffee, I will tell the clerk "... and I'm buying this young lady her coffee.", even if she is, apparently, my age or older. It always earns me a smile and a 'thanks". :)

[Alice Torn]

Good for you Jodie. A while back, I noticed a woman who had not enough cash in her account, in a gas station store, and she was not my type, but was hurting, so i told her i am covering her purchase. I has happened for me, before, too. Feels great!

[Vickie_CDTV]

Today, bringing up a woman's appearance at work is a death sentence for a man. You just don't do it. They told us this back when I was in high school 25+ years ago. I just can't believe a man today would even think about mentioning a woman's appearance or what she is wearing at the workplace.

Even outside of work... Maybe it is a regional thing, but I wouldn't go up to a woman who was a complete stranger and mention her appearance. It just seems like an invitation to trouble. It may come off at patronizing to some, and outright harassment to others.

I miss the days when men could complement a woman's appearance and it was appreciated, and common sense was common and everyone could agree on what was and was not appropriate. Those days are long gone. This is the era of microaggressions and professional victimhood. People wonder why so many adults are lonely today.

[Alice Torn]

Vickie, Well said! I would not dare mention it in a work place now. I need to be far more careful in what i say to cashiers too. My brother got banned from a bank, for saying something to an employee there.

[Asew]

Before I was out, even telling my wife that I prefer in skirts and dresses didn't go so well. Though she did go from zero skirts and dresses to maybe 25 dresses (granted each one has probably only been worn two times on average). I realize now anyone should be able to wear what they want.

[Tracii G]

[QUOTE Those days are long gone. This is the era of microaggressions and professional victimhood. People wonder why so many adults are lonely today.[/QUOTE]

Isn't that the truth !!
Professional victimhood is a great way to describe a lot of people these days.
Common sense is a rare thing anymore it seems.

[Helena]

Are things different here, or have I been living dangerously?

I regularly compliment colleagues. I have complimented strangers. There has to be some level of proximity such as queuing. I can't remember a negative reaction, more often a smile and a thank you. Keeping it simple and neutral may help?

Even the simple act of noticing goes down well be it a new hairstyle, new nails or outfit, afterall they have invested time and money.

[Vickie_CDTV]

It may be a different culture where you are. Some people are so sensitive in the USA it is easy for a benign complement come off as creepy or offensive. Especially in the workplace, at least here in America, men mentioning a female co-worker's appearance in any capacity is a huge no-no; doing that here is definitely living dangerously. One misunderstanding and you can lose your job and have your reputation ruined.

[GeminaRenee]

Have you ever teased some Gal pals about not wearing dresses enough ?

I'm always amused at the irony of a crossdresser giving advice to others about how to dress. Missing the forest for the trees and all.

[Robbiegirl]

I am a bit older so I was refering to experiences I had back in the late 70s and 80s

These days when I joke with lady friends about up coming social events telling them i hope to see lots of Party dresses worn they Always volounter to have me over so i can Borrow one for the event . many have joked that all the men should have to come in dresses ! Love women and their sense of humor

[BTWimRobin]

Honestly NO WAY! I would never suggest to a woman that she needs to wear dresses more often. That's like playing with fire on so many levels.

[lingerieLiz]

Most of the women I know, senior citizens, seldom wear dresses. Quite a few know I wear women's clothes so they would assume I wear dresses.

[Stephanie47]

Stephanie, I was given the distinct impression that the complaint was filed against the intern because she made all the other women look bad and the other women didn't like the male attention the intern was getting. It came across loud and clear that they were jealous of her looks and the attention she received. I did see this intern and she was gorgeous!

A complaint filed "just because" a woman is gorgeous and dresses nicely is not grounds in itself for a complaint. Yes, as an observer if those women observed guys drooling and stumbling all over themselves, perhaps their argument was a "hostile work environment." A person does not have to be a participant in drooling episode, but, just an observer. IMHO, the situation as described would not hold water if the intern was not encouraging the men.

[stephenie3756]

Vickie_CDTV - agree with you 100%. I would love to compliment a woman on how she is dressed at work, but to do so would be a death sentence. I sliently admire what she is wearing and wish that I could wear it too..... Same thing out in public. There are many women I would love to say, "You have a terrific style. I like your (insert item here), etc"....but with today's environment, no way.

[Jodie_Lynn]

OK Girls, here goes.

Stephanie, I was given the distinct impression that the complaint was filed against the intern because she made all the other women look bad and the other women didn't like the male attention the intern was getting. It came across loud and clear that they were jealous of her looks and the attention she received.



I have to call shenanigans on this. Unless the intern was violating the company dress code, i.e. by wearing outfits that would make a stripper blush, there is no way in hell that any HR rep would act on this "complaint".

I can just imagine the discussion that would take place:

HR: "OK, Sally, the reason we're having this discussion is that some of the employees think that you are too attractive."

SALLY: "I'm sorry, but what...?"

HR: "Yes, some of our older employees are threatened by your youth and good looks. So, if you could just gain about 60 pounds, or maybe mutilate your face, that would be great!"

SALLY: "You'll be hearing from my lawyers..."