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

  1. #1
    Aspiring Member Robbiegirl's Avatar
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    Love telling Women I miss seeing them in Dresses ! They usually offer me one to wear

    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

  2. #2
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    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.

  3. #3
    Member ronny0's Avatar
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    Quote Originally Posted by Linda E. Woodworth View Post
    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.

  4. #4
    Silver Member NancySue's Avatar
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    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.😔

  5. #5
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    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.

  6. #6
    Silver Member Micki_Finn's Avatar
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    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.

  7. #7
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    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.
    Last edited by kimdl93; 08-08-2019 at 04:32 PM.
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  8. #8
    Silver Member Micki_Finn's Avatar
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    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.”?

  9. #9
    Super Moderator char GG's Avatar
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    Quote Originally Posted by Micki_Finn View Post
    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!!) 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.
    Last edited by char GG; 08-08-2019 at 05:03 PM.

  10. #10
    Aspiring Member Joyce Swindell's Avatar
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    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.

  11. #11
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    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.

  12. #12
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    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.

  13. #13
    Silver Member giuseppina's Avatar
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    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.

  14. #14
    Girl about Town Jodie_Lynn's Avatar
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    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.
    Last edited by Jodie_Lynn; 08-08-2019 at 06:27 PM. Reason: "where" NOT "wear"
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  15. #15
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    I love dresses

    [SIZE=1]- - - Updated - - -[/SIZE]

    Would love to wear a dress and heels at work

  16. #16
    Junior Member Charlyne's Avatar
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    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,

  17. #17
    Gold Member Alice Torn's Avatar
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    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.

  18. #18
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    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.

  19. #19
    Female Illusionist! docrobbysherry's Avatar
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    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.

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

    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!

    No conversation necessary!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  20. #20
    Aspiring Member Michelle Crossfire's Avatar
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    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.
    [B][I]Call me Michelle: doll:

  21. #21
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    Love telling women they look good because I envy the choices they have

  22. #22
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    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 !

  23. #23
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    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.

  24. #24
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    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.

  25. #25
    Platinum Member alwayshave's Avatar
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    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.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

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