I honestly can’t explain why I do it. First time I dressed was as a 12 year old. I was at my neighbours during the school holidays and we were bored, so she decided to dress me up. I fell in love with it then and have dressed ever since. All through my teens I would wear my older sisters clothes whenever I was home alone. I would intentionally not go out with friends some days just so I could dress. Got caught by my sister twice but brushed that off as “teen experimenting” lol. Moved out of home at 17 with my pregnant girlfriend and stopped dressing after that, except for the odd occasion when my partner was out. After a few years I started to buy the odd pair of shoes and dresses from eBay and hid them in the shed where I knew she didn’t go. That’s how it was for the next 8 or so years until we broke up. Met my current wife a while later and moved cross country. She was pregnant and having my issues so I was taking care of all the house work and looking after her. I jokingly said one day “I’ll have to get a cute little maids outfit”, to which said laughed and said yea go for it. So I did. I ordered one of eBay and went and bought a pair of black strappy wedges to match (first time ever buying woman’s clothing in person from a shop). She didn’t realize I actually bought it until surprised her one day and walked in to the room wearing it. We both had a great laugh. Later that day after doing some house work, something clicked and for the first time ever, I decided to open up to someone about my secret passion. I was very scared but told her, and all she could do was hug me right and tell me how much she loves me and that it was ok. Later that day she pulled out some clothes from her wardrobe and gave them to me. That was 4 1/2 years a go. I now have a whole room dedicated to my shoes (well over 100 pairs), dresses, etc. She often shows me shoes and dresses to buy, for both me and her.
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