My Journey (Part 4) - Worklife and Marriage

by - August 29, 2020


4 years of university zoomed past and before I knew it, I was quarter of a century old and into the workforce. This meant that I was back living with my parents (fewer opportunities to dress up) but had more disposable income (SHOPPINGGGG 🛍👗).

I had started to build up a larger stash of clothes (nowhere near my current size), and squeezing in dress up sessions when I could. I had yet to discover makeup and took no effort to do so, in part because I didn't have the luxury of space and time to properly try it out at home. Although I could have booked a hotel room to try it out, blowing $200 just to dress up for the night didn't exactly feel justified.

(I could have booked Hotel 81 to save money but I wasn't that desperate 😅)

Work was stressful at times and I felt that my gender dysphoria flared up a bit more at night during these moments. In my brooding moments I would question my sexuality, the unfair cards that life has dealt me, and whether I had the strength to stay in the closet for my entire life. In the darkness I would wish fervently that I was a beautiful woman, but open my eyes to see a flat chest and manly arms/legs. It was disappointing that it would all remain a dream. 


But being a realist, I just counted the good things going on in my life and tried not to feel so sorry about my self. Plus there was also work the next day so I just brushed it all off and went to sleep. Usually, the busyness of the work day and people all around was a pretty good distraction to brooding thoughts. That being said, I don't think I had sorted out my emotions properly. Guys have this bad habit of not talking through their feelings, ignoring emotional needs and shoving them deep down, only for accumulated issues to manifest again with a vengeance.

On the relationship front, guy mode was doing pretty well. After a long period of dating, I finally popped the question and asked my girlfriend to marry me (she said "Yes"). I had considered telling her about my crossdressing on many, many occasions, but I chickened out everytime. I couldn't bring myself to jeopardise the relationship I had spent so many years building, and felt obligated to continue the illusion that I was just a normal dude. I swore to stay in the closet for life (Nope, I didn't 😅. More to come in a future post)

Nevertheless, I was happy that I was marrying the girl I loved. We went into wedding preparations rather quickly. Some guys are known to hate wedding preparations, but oh no, not this guy. It was pretty fun, and one of my favourite activities was visiting wedding dress shops. I would walk down racks of wedding dresses and occasionally feel the fabrics of a gown I fancied. If it was really pretty, I'd pick it for my wife to try. In a sense I was living vicariously through her. My taste wasn't too shabby, so my girlfriend was very open to my suggestions. Win-Win for everyone 😁

(The old Gown Warehouse in an industrial building in Woodlands. They have since moved to Dempsey. Oh how far they have come)

Of the shops visited, I especially liked Gown Warehouse. It was a massive shop decorated with plush carpets, chandeliers, with rows of neatly arranged dresses. But what I loved was the elevated platform at the front of the shop; with large full length mirrors at different angles, and spotlights aiming down for maximum effect. Even till this day I would occasionally fantasize about being the bride-to-be, trying on gowns, admiring myself on that stage and feeling like an absolute princess.

Ok, I should stop gushing about trying on wedding dresses 😬 Back to the story

(BTOs are cheaper but man do they take a long time to build)

Married life didn't really have an impact on my crossdressing, as my wife and I occasionally lived apart in our parents' home as our flat wasn't ready yet. I still had my own private space now and then. It was only when we moved into our own BTO flat did I start to feel the change. I took extra care to designate well-hidden spaces in the house to squirrel my ladies' clothes, brestforms, wigs and heels (they were in opaque boxes, within unsuspicious plastic Toyogo wheely boxes, out of sight at the back of the storeroom). But even with this precaution, I felt a growing worry that my wife would accidentally stumble in on me in women's clothes and the fallout that would ensue. For the first time, I was unable to sleep away this worry. My questions had come back to haunt me once again. Was I truly able to stay a closeted crossdresser for life? 

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13 Comments

  1. Understand your worry that wife might find out. Was in the same situation

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    1. I think a lot of us are. Which is why, it probably is better to come out at the start of a relationship

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  2. Can relate to all the point you mention. Waiting for more updates!!! Can't wait to know the going to public experience. For me thats the best experience going shopping as a girl and trying out all the clothes my eyes caught on.

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    1. Shopping in public....I'll probably write about that in the future. For something so mundane, to us CDs it is a great adventure

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  3. Can't wait for part 2 ��

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    1. I meant Part 5, haha! Thank you so much for your sharing.

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  4. Can feel it for you. It's a make or break.
    If you make it, you can even dress in girls' clothes at home
    otherwise, it will be a disaster

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    1. Coming up in Part 5. It's taking a while though because I'm really swamped with work

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  5. Just a quick intro, I am also a CD, I have been following your blog since it was shared on FB. I can totally relate to you as our journey is somewhat similar. I am also happily marriage now but I am keeping mum about my CD habit. I did a couple of purge over the years until I gotten serious about CD after learning more from the community and also CD like you, who is willing to share. I have my strategies of keeping all these in the dark. Not sure if I will share with my wife about this. Maybe in near future? Maybe I will snap out of it again and do another expensive purge? Who knows? But I am truly inspired by your sharing and looking for more of your sharing. Thank you.

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    1. Thanks Francesca! It's really not easy to come out when there's a lot at stake (well for some it's super easy cos they're YOLO). I won't dare to advise whether one should come out or not, as everyone's situation is different. Acceptance does feel incredible though.

      On the topic of purging...please don't. It's expensive AF. And we all know the urges will come back

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    2. Hey Isabelle, thanks for your reply. Really inspired to write my own blog after reading yours. It is really courageous for you to tell your wife about it. You are right, each of our situations are different. Currently, I am quite happy with my arrangement. Let's see how it goes.

      As for the purging, you are spot on. I purged 2 times and it is really "OUCH". Not only is it expensive. Some of the items are hard to find now. Oh well, lessons learned. Haha. Hope to get my blog starting soon and will always camp around to read more of your updates. Cheers. :)

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    3. Sounds great! Look forward to reading your blog if you do decide to write. It is pretty time consuming to come out with topics and write the post. Or maybe I'm just a bit slow in writing

      Fortunately I haven't purged....but that might be because I'm too much of a cheapo to do so 😅

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