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One of the things about being a cross dresser, is that I look at women and their clothes much differently than other guys, at least I assume so. I mean, when I look at a woman in an outfit I find attractive, if I look her up and down it is never because I’m thinking about sex (I try not to do that because it’s offensive and poor etiquette), it’s because I like the look and am wondering if I could pull it off. I often look at beautiful women with good style for tips and ideas. I imagine that I look at women the way many straight women do.
This often puts me in a position where I want to give a woman a compliment, but am afraid to do so. This happens at church most often. I often see an outfit, dress, or shoes that I really like (and maybe envy a bit) and want to be nice by complimenting the woman, but know that it might make her uncomfortable and would otherwise seem inappropriate within the context.
On the one hand, I want to say, “Don’t worry, I am complimenting you as a sister. I’m a cross dresser, not a creep.” On the other hand, for many the cross dresser and the creep are the same thing. Guys are often taught to compliment women on their shoes or something, but it’s always in the context of impressing them on a date or another situation that is sexually charged. No one seems to think that a man complimenting a woman can come in a way that is purely aesthetic or friendly. There’s always some other baggage attached.
At work, it seems a bit easier, however. Because I dress up for work once or twice a week, it seems like the women understand that a compliment can come from me without any sexual connotation. Maybe it’s still awkward for them, but it seems different at any rate. When I say, “I like your blouse,” I know they know that it means something different than when another man might say it. They tend to laugh a bit so maybe they just think I’m silly, but at least I feel like I can give a compliment without looking creepy.
One last thought, be sure to return compliments. One day when dressed up I was coming back from the water fountain and a friend complimented me on my outfit. It wasn’t until we had parted that I remembered that I should have complimented her. It’s the kind of thing that doesn’t happen in guy mode, but is an important part of being in girl mode.
Absolutely right – always return a compliment.
If you’re en femme, it’s much, much easier to give one too.
Girls love chatting about the clothes they’re wearing, especially if it was a bargain – so a back-handed compliment is to ask how much it cost and where she bought it
If it was a bargain, she’ll chatter excitedly, and you can compliment to your heart’s content, just like a girl!
If you’re lucky, you’ll get to feel the material – but no groping under any circumstances!!!! You are representing all cross dressers, and we will be cross if you give the wrong impression of us!!!
Love Laura
I know what you are saying. All my life has been admiring what girls wear. It is a male trait in failing to compliment a lady on what she is wearing. Women are more free in complimenting each other so it would be a given that ,while En femme to kindly remark on what a girl is wearing. I have received many compliments on what had chosen to wear that day from friends or colleagues. It is another nice thing when a sales girl or complete stranger wanders up and compliments something I am wearing. It can lead to a nice conversation.
With regard to being at church I would assume that it is a fairly regular congregation it wouldn’t be odd to strike up a conversation about the meeting and then compliment the lady.
Hi Sarah,
I’ve just got an idea that most women will come to recognise your compliments for what they are as opposed to a chat up line. I’m often forgetful or get it wrong. Today a ggf said I was looking thinner, but instead of reciprocating something nice, I just got lost in the ‘opinion’ and I assured her my bathroom scales said otherwise. No, I didn’t need to go there.
Marti xxx
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Yep its tricky complimenting a woman on her outfit and can be taken wrong so easily. One of my wifes aunt is a sharp sophisticated dresser and always wears nice expensive dresses and jewelry.
I was always afraid of complimenting her and being taken wrong so one time she was wearing a beautiful stunning dress so I told my wife that I really liked her dress. My wife turned and said to the aunt “My husband really likes your outfit”. OMG… I wanted to disappear because she said it in front of the aunts husband and also my wifes brothers. The aunt looked at me like “What??” and the men sort of just snickered. Later I told the wife… “Thanks a lot”. Not sure if the wife was jealous or she was getting back at me for coming out to her.
Be careful complimenting women because you don’t know how she will take it.
Hi Sarah!
If a woman gave me a compliment first, I would then return the compliment.
Well? Anyone?… Someone?…
Hugs, Barb 😊
what a wonderful thing to say, Barb 😉
Marti x
Sarah, In guy mode I’ve often complemented women. I do it with a friendly easy smile, and sincerity. In other words I only complement if I really like the item or look I’m complementing on. That way it usually comes across as authentic. And since I love everything about women and what they wear, it’s easy for me to be sincere. For the most part they appreciate the compliment. And in general I think women are more open to giving and receiving compliments than men.
Hugs
Jules
💖🌈👩Hey Sarah. Now a days I no longer hesitate to compliment a woman – be it on her outfit, her hair, her nails…. whatever catches my eye and looks lovely to me. Julie summed it up perfectly – A compliment wrapped in a friendly smile and sincerity is usually appreciated by people. And showing some kindness towards each other is a nice change from all the anger in the world.
And I usually get a “Thanks Hon” and a smile back, which makes me smile. 🙂
Stevie
Hi Sarah
Such a coincidence you should post this yesterday. Yesterday whilst I was doing a Voulenteer shift (in drab) at our local COVID vaccination centre I actually did pay compliments to one of our customers. In my Voulenteer role I do Meet and Greet and also post jab observations, I love this role as I get to meet and chat to so many different people. Yesterday during a quieter period a lady came in for her booster jab and I actually did a double take, you see she was tall, I would guess about 5’ 10/11 , long auburn hair (very similar to Stephanie) she was very attractive but it was what she was wearing that really caught my eye, she wore a cute white fluffy jumper, long midi flowing skirt in shimmering autumn leaf pattern and black boots, it really had the WOW factor and for me it was exactly the outfit I have been recently looking for for Stephanie. Anyway to cut a long story short 🙄 whilst having a chat I couldn’t resist complimenting her on her outfit and she was so pleased 😀 I had done so, when she was on her way out I plucked up the courage to ask her where she had bought the skirt? After telling me, her parting words were “Thank you for the jab and for your sweet compliments” then she winked at me and said “ And I love your High Viz” lol.
Love Stephanie x
I’m not sure if I’d compliment a total stranger unless it was something really stunning. (There’s a shortage of stunning in rural Cornwall, mind, so I’m not being over-generous) but I would and do complement friends and aquaintances. It would feel a little odd with strangers, I must admit. Not sure why – I’ll have to mull that over.
Connie
xxx
Sometimes it’s hard to switch off!
One morning while waiting outside an ASDA store, two young ladies were showing their new dresses to each other. They were so pretty, so natural and their summer dresses were gorgeous.
I had the urge to tell them but I was in man mode and hadn’t got the nerve. I wonder what their reaction would have been?
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