My Journey (Part 14) - Unsatisfying dress up session

by - September 11, 2022


After a really busy period, I finally carved out time to take a day's leave and have some Isabelle time to scratch the shopping itch. So on a Monday morning, I did my usual dress-up ritual; wake at 7.30am, travel from my parent's place to my own house, eat a heavy breakfast that would double up as lunch (eating in girl mode is a bitch and messes up my makeup, so I usually skip lunch on dress-up days. Also I dislike being stared at while eating), shave, bathe, dig out all my crossdressing stuff from the storeroom, spend an hour putting on makeup and transforming into Isabelle by around 11am. I'd then travel to the usual mall to visit my favourite shops. I'll pick out pretty outfits that catch my eye, try them out in the changing room, take some photos/videos, before heading back home by 3pm to round off the day with an outfit test of the new dress and wig I had purchased online a week back. There wasn't enough time to do a proper photoshoot at home, so I just used my phone camera as I was also feeling lazy (which resulted in underwhelming photos that weren't sharp enough). By 4pm I had to de-drag, take another shower, pack my stuff back into the storeroom, before travelling to my parent's house just before the evening peak our traffic.

Whew. What a day. I sated my desire to shop, but I felt....unsatisfied. Dressing up felt like a rush and obligation, which left me even more tired than a full day in the office. A chore consisting of a huge to-do list to tick off. Like why did I even bother to dress up? 


I did a quick poll with my Instagram followers and feeling unsatisfied after a dress-up session wasn't a unique experience. Although the rush that I put myself through during each session was definitely a contributing factor, I don't think it is the only reason. I've been in the normalisation phase for quite a while now and have this niggling sense that my desire to dress up has been waning. The feeling of having been there and done that has sapped away the novelty of dressing up. What is the next thing for me to look forward to when dressing up? I've even started looking around for another bridal studio to do another photoshoot, but it feels like another attempt to blow a couple thousand dollars to chase the next hedonistic high. I get to wear some pretty gowns for a couple of hours, have photos to show off for it, and then what? 

I suppose this is why people retire from crossdressing after a number of years. Because the hassle of dressing up outweighs the derived satisfaction and desire to do so. 

I do have some plans to make dressing up seem less like a chore, starting with getting rid of my facial hair. I absolutely detest having to grow out a week long beard to a decent length before spending one hour plucking the individual hairs out for a truly clean look. I've gotten used to the pain but the time it takes just annoys me to no end. I do also hope to dress for a longer period without having to rush back home for my parental duties, so that will require some logistical arrangements. Halloween and Anime Festival Asia (AFA) is coming back this year with all the covid restrictions removed, so I also do hope to at least try attending in costume, which would make things a bit more interesting.

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1 Comments

  1. Thanks for sharing Isabelle. I guess we CD go through this normalisation phase or got caught up with other aspects in our personal life that will take us off from CD. Usually at this phase, a lot of CD will do the unthinkable, purging only to regret later. What you need a really a good session and time for yourself or just really take a short break and plan a good CD session in a private hotel until the night. Or just go easy on CD until you need to spend shorter time for parental care duties. Best if your wife's friend can come over and accompany your wife and child while you take a short leave.

    As for your facial hair removal, I have been doing it for quite a while. I just watch YouTube ot Netflix and pull out the hair. Feels shiok and clean. This really reduce the time for us to CD. I have shared my make-up process and that took me almost like 1 hour to get my make-up done. So good to do the prep at time while in guy mode. Haha.

    Anyway, keep writing and keep that passion to CD alive.

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