I'm A Man And I Like Dressing Up Like A Woman: My Sister Is Married Now But I Want To Try It Again

Anonymous Anonymous in Fashion Ki Dukaan on 2 December, 2016

How it all happened 

Three years ago, my cousin and I conspired to let her deck me up as a girl. For the sake of brevity, I'll omit the series of events that led us to this tomfoolery. So that day, I wasn't aware until noon that my cell phone's battery had died. I plugged it for charging and after an hour, I got a call from my dear sis. She was mad at me because she had been calling me since morning. Her folks had gone out of town and she had the entire house to herself. Perfect situation to make some good progress on our dress-up pact. 

She tried my number again at about 1 pm, and I was at her place within an hour. All perked up, she enthusiastically showed me her well-stocked makeup kit and the clothes she had selected just for me. While I was a good sport about this dressing-up pact on the phone and emails, I got nervous when it actually came to walking the talk.

I asked her if she was serious about this. She realised I might back off, and the corners of her mouth dropped. I thought it'd be awful to let her down after hyping this antic so much. So with some awkwardness, I said, "let's do this".


When she made me wear a sensuous Satin Nighty

And there, she excitedly pulled out a red, satin nighty she had bought for me. Yes, she had bought it for me. Noodle straps, a rose on the bust, deep back, calf-length... She held it out for me and asked me to wear it. Well, I went to the bathroom, changed into it, came out, feeling nervous. And then began her laughter riot. And the series of compliments.

"Whoa! Boy! You have a sexy back!"

"These straps look so good on your lovely shoulders, bhai!"

She was on a roll, commenting, teasing, giggling. She smoothened the nighty for me and had me twist and turn as I was still feeling shy in that sensuous little thing I wore for the first time. She rejoiced seeing me acting all coy and shy. She was staring intently and I could feel her piercing glance.  

Did I feel vulnerable? You bet I did. Delicate straps on my shoulder, a deep back, the nighty's colour itself. So feminine. My face turned a shade of red and my cousin took to teasing. "Awww! You are blushing! How sweet my 'sister' is looking in this nighty!" Then I wore a tube top for her.

Denim skirt 4

Next on the menu: A tube top-cum-skirt

Yes, that! I was like, "But how is it gonna hold up!" She responded with fake sympathy, agreeing that I don't have the 'assets' to carry off the tube top. It had an elastic band, so she got me to put it on anyway. I did, and she had such a jolly time teasing me for having a flat chest. What's funny about a boy with a flat chest? Nothing. Just that the moment our cross-dressing started, she started teasing me as a girl. And she was making fun of this girl who stood there in a tube top with such underwhelming breasts. She kept cracking jokes. I felt silly and funny!

Skinny jeans and things

By this time, my nervousness had started melting away, all thanks to her laughter and teasing. She was enjoying from the moment I had stepped out in that nighty that night. I too had started enjoying by now. She was dominating all along. Calling the shots and poking fun at her new 'girlfriend'. I thought I should take lead now. So I asked her for her jeans. I thought jeans-top would give me a respite from these overly feminine items she had been making me wear. However, I was so wrong.

That pair of skinny jeans that she handed to me, it was of course stitched to fit a woman's body, but it fit me as if it was tailor-made for me. Thanks to overeating, and the consequent fat on my bums and thighs, I filled her jeans perfectly. Curves and all. Her girly jeans sitting way below the belly button, tightly hugging my bum and legs, it felt like second skin to me. She was awestruck at how girly I looked in them. She was gaping, drooling upon my legs. I looked that sexy! To complete the look, she gave me a pink boatneck top. A long top. Thanks to its feminine cut, it made my torso too look feminine and curvy. All traces of awkwardness had vanished by then and I was comfortable with the silliness of the moment. Even confident enough to join her in the fun.


To stump her and to see her reaction, I said, "No good girl wears a top with nothing underneath it." This threw her off a bit. 

As if suddenly lost for words, she pulled out a slip for me. Turned out that she was taken aback only for a moment. She seemed happy, not shocked, at my act of escalating the fun. Like a proud elder sister, she watched over me as I held the slip up and examined it intently. I was getting introduced to the female wardrobe and soaking in the experience like a wide-eyed newbie. My cousin was only too happy to help. After poring over it, I wore the slip. And how happy my sister was! She thought I looked hot in the slip-skinny jeans combo. I have to admit that I did feel different standing in those garments in front of her. I wore the top over the slip and as I began to tuck the slip's straps, my cousin stopped me and restored the straps' normal position, saying:

"Straps should show with this top. Boatneck tops mein straps dikhaate hain.

That long top, hot pink in colour and boatneck... Its cut was such that it gave an illusion of curves even on me. I was thoroughly enjoying the experience and was learning a lot about girly stuff.

Curiosity started building up. 

When girly feelings started setting in

It was a strange yet fun moment! My sister giving me girly tips, treating me like a girl throughout. She thought I should wear her bellies too, to complete the look. As she and I have similar sizes (she's slightly plump), her clothes fit me just right. She had a laughter riot, calling me her girlfriend, sister, complimenting me, envying my 'figure'. She commanded me to do a little ramp walk for her too. She also dared me to take a stroll on the terrace dressed like that. I boldly did so, even standing at the balcony without a worry, least bothered about anyone seeing me. For, from a distance I looked like a girl with boy-cut hair. No exaggeration.


What was the outfit for the day? Anarkali 

As the gala time continued, she brought me the next attire: an intricate Anarkali suit. It was decided that makeup would go with it. She asked me to be careful as I were to slip into those delicate satin salwars. It felt so delicate to hold that I myself was cautious with it. And boy, I didn't know slipping into that Anarkali kurta could be that tricky. She helped me get into it and then did up the zipper at the back. I was beginning to wonder, how do women do all this by themselves!

Ah, so there I was. In a regal Anarkali suit. Light purple in colour, clearly made for festive occasions. Satin salwar and a lovely flaring top with delicate full-length net sleeves. My sister smoothened the long top and both of us were in awe over how nicely it fit. 

Until this ensemble, whenever I'd put on an outfit, she'd tease me and give me compliments with a naughty look, how my figure looked so girly. She would look at me up and down in full admiration, asking me to turn so she could check me out and drool upon her new 'sister's' curves.

"Kyaaa figure hai yaar tera! Yeh figure mujhko de de."

She would ask me to stand facing her, continue gaping at those curves, her gaze would stop at my flat chest, and she'd say: "Bhai poora ladki jaisa figure hai, bas ek kami hai." You could sense mischief and greed in her eyes. Greed to have her brother wear, well, a bra and achieve the full feminine figure. She didn't need to say it, her body language did. 

'Bra'vo! I said. As I had started feeling a bit adventurous now, I took her bra that was kept for drying and said I'm wearing it. I was a bit unsure about how she'd respond to it. I had this apprehension that borrowing her most intimate garment might not go down well with her. I was so wrong! When I took that black bra from the hanger and announced we're adding it to our final look, she had a look of joy and disbelief. She did want me to wear it.


Well, I had to take off that delicate Anarkali kurta to wear the bra. I slipped my arms into the straps, but just couldn't do the hooks at the back. Ugh... How do girls do it? How to get both the hooks right? My cousin couldn't control her laughter seeing my struggle.

She was merrily hooting. "Wow, bhai! These black straps on your fair back look so sexy, yaar!"

"Seriously, give your figure to me."

She went on and on, her giggle-fest continued. After trying for a good couple of minutes, I gave up. I had to ask her to help me with the bra. She was happy to oblige. She asked if the bra fit nicely (teasingly, of course) and said I'd learn with practice. My face had turned red, as I felt a little shy, wearing those satin pajamis and a bra. She snapped the straps and teased me a bit more. I was just blushing and trying not to show it, but it did show at some point.

Now, we had the dilemma of filling up the cups of the bra. She had a stress ball. That went into one cup. For another, we had nothing but a leather cricket ball. So I had a light ball for one breast and a heavy ball for another. Throughout, the heavy 'breast' kept drooping and I'd naturally adjust 'my' bra. This sent her into a fit of laughter, yet again.

She commended me for being so girly, naturally, but reminded me that no 'decent girl' keeps tugging at her own bra. I just sat there coyly, following her instructions.

Overpowering feminine feelings

I have to underline here that wearing that Anarkali suit brought an overwhelming feminine feeling in me. While all of the previous female garments too were a novel experience and all of them felt different, none of them had the grace, elegance and delicate, feminine nature of the Anarkali. None of it had that regal quotient. The feminine feeling was so strong that it subdued the fun and mischief element in both of us. We were just in awe at how beautiful it looked. My cousin pointed out that I looked like a model: tall, slim, curvy. If I can be honest, this overpowering feeling or whatever it was left me awestruck. 

When my sister painted my face with all things nice 

My sister then made me sit on the edge of the bed. It was time for makeup! I was careful to sit so as not to ruin the kurta. My sis was impressed at how naturally I was doing these things. So finally, the makeup began.

First was eyeliner. She asked me to close my eyes, and then I felt some liquidy thing on my eyelids. Applying it must be such a craft! She applied mascara, telling me it should be done in a zig-zag motion. Another trivia that I learnt. Then came a touch of eyeshadow, of the same colour as my attire. Blusher on cheeks, lip liner, lip colour... I don't even remember what all went on my face. I just remember brushes on my face. Powder, cream, lipstick. And subtle, feminine fragrances. I remember telling myself, 'that's why girls smell so sweet'. Brushes of different shapes and sizes ran on my face while my cousin enthusiastically narrated what she was doing to me, what the right way of doing it was and why it is done. 

She was like a loving elder sister who was inducting her newbie younger sister into the art of decking up. I loved all the adulation and adoration coming from her. 

Earrings, Bindi, Heels, and what not 

When my partner-in-crime was done painting my face, she got me earrings (both my ears are pierced), a bindi and her heels, which were a size too small, but they still fit. And then I was taken to the mirror. I remember looking at myself, feeling funny at first. And feeling feminine the next second, if I may be honest. My sister had a blast decking me up, and she had done a good job. I was impressed with her artistry and in awe of that new, striking experience. I sport cropped hair, and she made me look like a female model with that hairstyle.  

After the makeup and accessories, I didn't look like a guy anymore.

Feeling girly inside out

I was surprised at how I had to walk and act differently after the transformation. The usual, callous guy-swagger won't do that. Thanks to the heels and the dress, I had to take small, careful steps. Sit elegantly. Even rubbing the eye wasn't allowed in case of an itch. For, eye makeup might smudge, my sister warned me. She was proud of her artwork. Indeed, I looked like a girl. She had me wear a dupatta and do a ramp walk for her, wearing different kinds of heels. She had me strike poses and clicked snaps.  

The bra's straps kept sliding off my shoulders and I had to regularly adjust them. She had a ball seeing me tackle these girl problems. That's when it struck me, I was indeed acting just like girls do. I smoothened the kurta before sitting, took short steps when wearing heels, I moved gracefully.

Femininity was dawning on me. I was learning and following girls' ways subconsciously. My sister was only too pleased with her efforts and at upon finding someone to do her girl talks with!

By the time we were done posing, cat-walking and admiring my cousin's fashion sense, it was almost time for her maid to come. That meant we had run out of time and there was no scope to try the two sarees my sister had laid out for me. She was disappointed. 

The longingness

I had such a comical and delightful time that I too regret I missed out on the saree experience. That day was hell of a learning experience for me. Though I've never been critical of women taking time to get ready, now I know why they take time. To get into these delicate dresses, adjusting it, putting on makeup, applying safety pins, deciding on the right accessories etc. takes time. Just like all good things take time. The fabric of the clothes is different. It feels different, soft. Just wearing certain dresses brings out gracefulness in the persona. This experience, which started off with a nervous, unsure me, left me totally in awe of women and their wardrobe. 

It's needless to say I'm raring to go there again. 

Now, having learnt, experienced and appreciated how different—and sensuous—women's clothing is, I'm actually eager to find out what wearing a saree feels like. When I was facing difficulty managing the Anarkali suit, my sis teased me how'd I manage a saree. Now I'm curious. Really, how would I manage it? What does it feel like to be in one? She and a couple of other girl pals with whom I've shared the story tell me it's a different ball game altogether and it's a pity I came so close yet was deprived of the experience. They highly recommend that I get that experience!

My cousin is a mom now, which leaves us with no scope of reliving that fun again and achieving the final frontier. While I may never get that experience, I’ve got to admit that having literally been in a woman's shoes, I realise what a balancing act one requires to ensure everything stays in place. Now I know that a woman looking immaculate in a dress or a saree has put in much time and effort to look that way. I understand pulling off the look is quite a task. Since then, I've become more appreciative of women. It'd be great if some day an opportunity comes up and I get to have another dress-up session with her, or some other fun partner-in-crime, and get to try all the feminine stuff I've missed out on for so many years. 

After experiencing femininity first-hand, I understand why women are called 'God's best creation'.
Editor's Note:

The author has insited on being anonymous and hence, he has used a fake profile to express his thoughts. My question, what's so bad about a boy who wants to wear a saree? If you dream of a society that's more gender equal do one can talk more openly about his/her preferences, share this piece and spread the word.