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by As told to Balvinder Sandhu / 


October 17, 2017

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MCI (P) 049/10/2021. Published by SPH Media Limited, Co. Regn. No. 202120748H. Copyright © 2022 SPH Media Limited. All rights reserved.
TRUE STORY: “I caught my husband trying on my clothes!”
He betrayed my trust but will I be able to get over this bump in our relationship?
My husband Jason* was turning 30 in a few weeks and I had a plan that I knew would surprise him. Instead, he ended up giving me the biggest shock of my life.
Jason’s birthday conveniently fell on a Saturday that year and I had a work trip the week before that. I was scheduled to be back home on the Saturday afternoon but I didn’t tell Jason that; instead, I put on an Oscar-worthy performance (I think it was, anyway) and acted really disappointed that I had a few meetings planned on the Monday so I had to stay the weekend too. I stressed how much I wished I could be with him on his big day but there was just no way for me to reschedule my meetings.
Jason didn’t seem too bothered as he wasn’t big into birthdays (not his anyway, he always made sure we did something special on mine). We had a dinner party planned the weekend after with a few close friends and family so that was enough for him. He told me we could have our own celebration when I got back to Singapore and that it wouldn’t matter to him that it wasn’t the exact day of his birthday.
So I went on my trip and touched down at Changi on Saturday afternoon as planned. Jason plays football with his friends every Saturday morning and always got home around 1pm, after they’ve had lunch together. He’s a creature of habit and I knew for a fact that he would be home the whole afternoon.
I got back to our flat around 2pm and went to my neighbour’s house first, so I could leave my suitcase with her. I didn’t want to make too much noise dragging my suitcase into our flat and ruin the surprise so I had arranged this with her beforehand. I also left a bottle of chilled champagne with her as I had dreamed of spending the afternoon sipping champagne – in bed, preferably – with the man the I love most in the world.
Once all that was taken care of, I made my way to our flat. I opened the main door slowly, just in case Jason was sitting in the living room – I wanted to surprise, not startle him. But he wasn’t there. I figured he must be in our bedroom and kept my fingers crossed that he hadn’t fallen asleep after his tiring morning.
I slowly opened our bedroom door and was stunned by what I saw. About a dozen items of clothing were spread across our bed and they were all mine. And, standing nearby, admiring himself in our huge mirror was my husband – dressed in my clothes.
I felt weak all of a sudden and dropped the champagne bottle in shock. Jason turned around and his face went white as he saw me – he clearly wasn’t expecting anyone to walk in on him, let alone his wife. A few minutes passed before either of us could say anything or even move, then he uttered softly, “I’m sorry.”
My head was telling me to walk out immediately but my heart desperately wanted to know what was going on. I don’t know where I got the strength from but I managed to walk up to him and ask what on earth was going on. He broke down in tears and soon, both of us were sobbing our eyes out.
It took a while for us to calm down then I told him that I wanted to know everything. He soon revealed that he has been trying on my clothes on and off since we got married, which was just over two years ago then. He said he had been doing so occasionally since he was a pre-teen, except it was his sister’s clothes then, not mine.
My mind immediately went to the most extreme possibility – was my husband a transsexual ? Did he want a sex change? Where would that leave me? But Jason assured me that he had no interest in anything beyond wearing women’s clothes now and then. He said it’s a form of escapism for him and that he doesn’t want to do it in public or even buy his own women’s clothes. It’s not like he had drag queen ambitions and nobody in his life knew about this secret.
It was a lot for me to take in. The first thing I needed to do was not be in the same space as him. I stayed with my parents for a few days, telling them I needed some time to think after having a fight with Jason. I didn’t tell them the truth, of course.
After a week or so, I told Jason that I was ready to talk about things. We agreed that we should see a marriage counsellor who could possibly point us in the right direction of how to handle this situation.
I confessed to Jason – and later to our counsellor too – that it wasn’t the cross-dressing per se that bothered me. Yes, of course it was strange beyond words to see my husband wearing my favourite Zara top but what bothered me more was that he hid this from me. Although I had other boyfriends in the past, Jason is the only man I ever truly loved and it felt as if I didn’t know him at all . Who is this man? Are there any other big secrets he’s been hiding from me? I felt that he had betrayed my trust and this trust issue was way bigger than the fact that he likes to wear women’s clothes sometimes.
Also, we had been trying to start a family then and I was thankful that we didn’t have kids in the picture to complicate things further. But, did that mean that we would never have kids? I certainly couldn’t imagine having sex with Jason again; when I close my eyes, all I see is him in my clothes.
Jason assures me that he still wants to be married to me and start a family together and that nothing will change. He says that he’ll be able to quit the habit as he did it so occasionally anyway. It’s going to take some time for us to get back to where we were and I sincerely hope that I can be strong enough to let him back into my life.
I know he’s not hurting anyone and I guess at least I didn’t walk in on him having sex with someone else. He’s still the man I love more than anything in the world and, fingers crossed, we make it out the other end with our love still as strong as it was before.
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I walked into my son’s school a few weeks ago to pick him up. He was sitting with all his friends waiting for me by the door and immediately got up when he saw me coming. Clearly, he didn’t want me coming anywhere near his friends. I got the feeling he didn’t want anyone to know he was with me. I was right.
As he got closer, he whispered, “Mom, why do you have to dress like that? Everyone stares at you.”
“No they don’t. They are probably staring at you because you are so handsome,” I told him.
“I blend in. They aren’t staring at me. They are looking at you. Why do you have to wear dresses and high heels?” For the record, I was wearing the outfit below. The nerve, right?
I decided I wanted to try something with my teenage son that day. I asked him if he wanted to dress me for a little while. I told him he could pick out my outfits and I would wear whatever he wanted me to wear as long as he had an open mind and would listen to a few things I had to say about people and the way they choose to dress, so that’s what we did.
I wanted to talk to him more about the subject and why he was feeling the way he was. And by having him choose my clothes for a while I would better understand why he wanted me to wear certain things, and maybe he would understand why I like to dress the way I do and that, really, it shouldn’t affect him as much as it does.
This was his choice for the first day. He picked out a very casual, sporty outfit, and I loved it.
While I dress like this about half the time and like this look, it doesn’t always suit me. Sometimes I feel like dressing up more, so I do. When I asked my son why he picked this out, he said because I “blended in and didn’t look out of place.” In his mind, when I dress up, I look like I don’t belong. If he only knew how many women I saw throughout the day wearing suits and heels maybe he would have a different opinion.
Regardless, I told him nobody should be judged based on how they dress — not even your very embarrassing mother . Most people wear what they are comfortable in, what makes them feel good. It doesn’t matter where it came from because this isn’t how we judge others. We focus on how they make us feel, if they are kind, how they treat people. I told him judging people for what they wear is very transparent, and he will be missing out on a lot in life if he is going to focus on making friends because of what they wear, what they have, or what they look like.
If he is comfortable dressing in a way that makes him feel like he blends in, I think that is great. However, I want him to have the inner confidence to step out of the box if he wants. If he feels like wearing something, even though none of his peers are, I want him to feel like he can.
I also let him know what someone puts on their body isn’t an invitation, for him or anyone else, ever. And he should always take heed on how he looks at people, especially women. There is a way to look at a woman without staring or gawking. No matter how you see her, she deserves respect. I don’t care what she’s wearing.
I also want my son to realize just because I am a mother it doesn’t mean I have to dress a certain way. I loved the outfits he picked for me, and dress like that on my own accord often. But I also love wearing dresses, heels, skinny jeans, and trying out new trends because that is who I am, and who I was long before I became his mother. It’s not my intention to embarrass him. It is my intention to be myself, and him making comments or telling me he doesn’t want to go anywhere with me because of the way I dress is hurtful (as normal as it is).
A few days ago, I discussed these “lessons” I was trying to teach him with a friend and she told me he would “take all these lessons and bake them into a gentleman pie.” I really hope she is right.

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