7 Things I’ve Learned (So Far) From Crossdressing

This is from Michelle…

Hi Slip

I enjoy corresponding with you via your blog, and would like to offer you some new perspectives I’ve picked up from my cross-dressing activities. As a man, these would never have or only fleetingly occurred to me. So I believe I’ve grown emotionally and intellectually.

1. There are an incredible number of ways to accessorize an outfit, an endless set of options, and I understand why women can take so long in their shopping habits. I mean, the task is never done. I buy skirts and look for the right top (which also covers my more obvious male parts), or a dress which is the right look, and then the hunt for necklace, bracelets, earrings and shoes goes on. I am truly humbled by this cornucopia of choices. I don’t ever complain about my wife’s shopping any more. I simply understand, and am awed.

2. Getting in shape underneath is also difficult and tricky. Men blithely assume that all shapely women were born that way, but I now know this is absurd. I also realise what they have to go through to look good. I have spent a lot of time in foundation departments and left bewildered by the array. Besides, these things can be uncomfortable. I never used to appreciate the old saying, “let me slip into something comfortable”, but now I do. I sure do.

3. Time it takes to dress. Of course, this is man’s favourite complaint about women, but men simply don’t understand how long putting together a look can take. From the clothing issues mentioned above to the make-up (another issue entirely) crossdressing has given me a new admiration for the magic women weave before they go out the door. (On a recent business trip with my female cousin, I called her room one morning, woke her up and said, ‘we have to leave for the airport in 10 minutes; you’re a woman, can you do it?’ She sighed and said, ‘yes, I’m a mother’, and she was ready, too, which impressed me enormously.)

4. Reciprocally, the frustration with men who don’t understand or empathize has become all too real. They want ‘us women’ to look good, but they want it now. Typical!

5. It’s annoying to be ogled! Man, what a revelation this has been! Obviously, when I’m dressed I may be ogled for different reasons, but I could feel that some were admiring looks, too (wow, can you ever tell). Now I understand why most women hate being stared at. It’s embarrassing and uncomfortable! And – get this – I hate the thought of someone looking down my (pseudo) cleavage at my bra, when, as a man, I do it to women all the time. Will someone stop me? as the Mask used to say. Everyone likes polite admiration, but when it crosses the line it becomes harassment. Boy, I know (but as a guy, will I stop? No. How’s that for double-standards).

6. As I wrote in my story, I appreciate why women like slow hands in love. And why they can’t stand men who paw them. In a CD bar one night, a male friend of a friend hit on both of us, and put his hand on my (exposed) shoulder. I had to control the urge to punch him (I was a woman, after all) or squirm. So I devised an instant strategy, just sitting politely unmoved until he got the message. Again, a light bulb went off (but has it helped me as a guy? Hmm, I wonder). When you’re al dressed, with everything tucked away neatly, the last thing you want is instant sex and turn-ones; you want a nice, slow build up.

7. Dresses are more exposed than pants. Instinctively, when I’m wearing slips in my room or a dress out, I keep my legs together, hold my skirts down in the breeze, and generally try to preserve my modesty. What’s under there is nobody’s business. I’d hate to have my skirt blow up in the breeze – I would die!

Slip, you’re probably the only person I can write this to. Call me a work-in-progress, still learning as I go, but I’ll never take women for granted again. Bless ‘em.

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