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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.


“I’m sorry”

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.

Photo: 123rf

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.



Can I trust him?

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.

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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.

*Name has been changed