My Evolution

I'm sure this story is very much similar to many others, but I'm going to write it anyway.

I don't exactly recall the first time I crossdressed, but it was sometime around age 11.  I would spend the next 30-40 years crossdressing on and off, always hiding it from everyone, building my wardrobe a small amount but never really seriously.

Through ********* I was diagnosed with seizures, psoriatic arthritis and at one point a fractured spine, then in 2020 when COVID struck, I was working from home full time, and it felt like the world was telling me to get on with my life.

I started dressing more and more, during the working day, then searching for social groups and content at night.  I found a lovely twitch streamer who was crossdressing on every stream, often changing during the stream, and this along with his ******* channel showed me that the current generation were much more accepting of crossdressing.

During late 2020, I was made redundant with a nice payout, then proceded to spend the next 4-5 months indulging my passion, buying new clothes and delving as deep down the rabbit hole as I could reach.  It felt like I was trying to make up for lost time, to build my wardrobe, to start doing makeup, buying wigs, learning everything I would need to do to try and 'pass'.  It was at this point I met Elize and discovered that I was not heterosexual.

In early 2021 I took my first step, contacting my best friend and telling him about my crossdressing (and my kink side too), it felt like such a relief to finally tell someone, but I still wasn't confident enough to go out dressed.

During 2021, my wardrobe kept expanding, my makeup skills improving, and my desire to 'pass' still increasing.  Finally an opportunity to visit Elize in Hamburg, and I decided that it would be Steffy who would be going.  Late July my male self boarded a plane, but it was Steffy who spent the next 9 days in Hamburg with Elize, dressing every day, visiting local restaurants and shopping malls, there were a couple of downsides but nothing related to my dressing.  This was a great experience and Steffy was unhappy to end it...

A month or two later and I was out with a group of friends, including my best friend.  I'd already decided I would tell everyone around the table about my crossdressing, and again everyone was accepting and supportive, so much so that they wanted to meet Steffy.  This wouldn't happen until a couple of months later, again we were going out in Windsor, but this time some more friends would be out, I told everyone before the night that I intended to come dressed and so Steffy arrived for the evening out.  It was a lovely evening, I received complements on my dress sense and makeup, but also I just felt like a much more open and relaxed person when dressed.

Since that event, every time I have gone out socially, I have gone out dressed as Steffy, and since the start of January this year I've looked for more and more excuses to go out socially.  I'm loving every minute of it.