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6 Lessons I Learned About Feminine Clothing As A Crossdressing Straight Man

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Editor’s Note: This post is a part of What's A Man, a series exploring masculinity in India, in collaboration with Dr. Deepa Narayan. Join the conversation here!

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By Riya Jain:

I’m a straight guy in my mid-20s who developed a love for women’s fashion around the same time when puberty struck. I’ve been extremely lucky to have some fun gal pals who share my excitement for dress-up and have indulged my feminine side. These young women have shared their entire wardrobe with me, right from exquisite anarkali suits to bellies and from accessories to make-up. Also, I’ve been quietly picking up women’s clothing in malls and trying them on in men’s trial room, admiring the look for a few seconds before taking them off and putting them back in their place. My years of experience dressing up as a woman would, and all the knowledge I’ve acquired about women’s fashion gives me a distinct advantage. I understand women’s clothing better, having walked in their shoes, literally.

It’s not that I ever lacked respect and appreciation for women, but this has given me insight which makes me appreciate them even more. Here are a few lessons I’ve learnt along the way:

1. Expert Knowledge In Women’s Clothing

I’ve become kind of an expert in women’s fashion. I have friends who insist that I go shopping with them when they want to buy an outfit or shoes. I’ve had friends and sisters who drag me to malls with them or exchange links of dresses and shoes online to select what to buy. This makes me a darling to these lovely women. I can’t even recall how many of them have told me it’s such a help and relief to have a participating shopping partner like me who knows fashion and is happy to accompany them even for window shopping. Most of my guy friends hate “wasting time” shopping whereas I just love checking out the new collection in every section on the women’s floor. I am these girls’ go-to shopping partner. We bond over this stuff big time! I know what a boatneck neckline is, what halter-neck means, the difference between block heels and cone heels are, and that one should rather wear petticoats with zipper instead of the old-fashioned drawstring (‘naada’) for sarees that will be draped tightly. Some of my friends even ask me to recommend blouse designs. And I keep egging them on to go for typically feminine looks. I had one conservative friend get a backless blouse stitched, and she loved it.

2. Being Sensitive To Time Required For Makeup

Poking fun at women for taking time to get ready is an act of ignorance. When my friend put makeup on me the first time, I was amazed to learn how much effort goes into applying makeup. You need a steady hand to make sure you get the eyeliner right, and equal on both the sides. Such a task! You just can’t rush it. Eyelash curler, then mascara in a zig-zag motion; upper lashes, lower lashes. and there is kaajal, of course. Adding colour to waterline, such a sensitive part. Then there is eye shadow, blending which requires utmost care. A little eyebrow pencil too. All this takes so much time and effort. And we’re done only with eyes by now.

3. Being Aware Of How Complex The Art Of Makeup Is

Full make-up, with foundation, compact, contouring, lip colour etc., is a work of art. And these things take time. You can’t rush it. I learned it when I was made to sit quietly as my friend explained what she was doing to my face and the right way to do it. Sure, it takes time, but the time and effort is worth it. Don’t guys go crazy over beautifully done smokey eyes or that neat-winged eyeliner or beautiful kohl-rimmed eyes? And only somebody who has applied nail polish can understand what expertise it takes to get a great, smooth finish.

4. The Difficulty Of Maintaining Makeup

Maintaining that makeup is another task in itself. Eat something and the lipstick needs touch up. Can’t dare rub or itch your eyes because you can’t afford to ruin your eye makeup. Just ‘deal with it’. This requires you to be conscious of yourself which takes effort and commands respect. I understand your trials and tribulations, ladies.

5. Not ‘Delicate’, Just Gentle

Some guys like to poke fun at girls for acting ‘so girly’ or so ‘delicate’. When my friend put me in her partywear anarkali suit, with its full net sleeves and net dupatta and heels, there was no way I could continue to be my brash masculine self. With all these flaring dresses, you cannot have a devil-may-care attitude. One needs to be careful. In my typically masculinr look, I’d rush to you instantly if you called me. En femme, I’d need to turn my head slowly. With those heavy jhumkas, you cannot afford to be brash and jerky. Being delicate and gracious is the need of the hour. And there are heels, of course. (I’m talking about stilettos, not wedges, since they are so easy I could do taekwondo in them.) With high heels on, do expect us to walk gently, not gent-like. You’d know only if you ever walked in heels yourself.

6. Appreciating The ‘Skill’

I’ve had the pleasure of being draped in a saree once, although only for 15 minutes. Trust me, it’s not a cakewalk. Particularly, when it’s draped tightly (like my friends draped on me to highlight my curves). I found myself taking baby steps when I was in that saree. I was left wondering how these women I see at parties glide around effortlessly in sarees and heels. I was filled with awe and respect for their skill. Yes, I think it’s a skill and I’ll be mighty impressed with you if you have this skill.

Until I myself started dressing up in a more feminine manner, it never occurred to me just how much effort goes into dressing up. So now when I see a gal pal whose eyeliner is on the spot, I ping her and compliment her on the job well done. If I see a friend merrily strutting around in pencil heels, I tell her I’m in awe of her shoes. They all seem mildly surprised that a guy would even notice such things. They thank me for noticing and some have even told me this appreciation feels good. The same bunch tells me I’d make an excellent boyfriend/husband, given how sharply I observe and acknowledge the things girls do and make them feel good through my sincere compliments.

While many girl friends to whom I have told about this dress-up affinity of mine have gotten scandalised by the revelation, I’ve been so lucky to have the ones who take delight in my adventures. I’m one ambitious individual. I’m keen to try on a saree again and I want to be able to walk freely in them. Chiffon, georgette, silk, I want to try it all! I’m also eager to try on a dress and soak in the feeling with bellies or with heels. It’s a challenge I’ve set for myself to walk freely in pencil heels. I hope to get the time and opportunity, and most importantly, sporting gal pals, to pull off an adventure, yet again.

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