A Photoshoot with Richard's Photography

In November 2021, Jessica Guest attended her first Transliving weekend, travelling down to Bournemouth from Nottingham: no mean feat given Jessica walks with a stick. She quickly endeared herself to the crowd. Shane asked her to write a short piece about her journey.

My journey is very typical; I was born in an era very different to today, with increasing acceptance of the transgender community. Raised in the late ‘50s and ‘60s, I realised at a young age that I was different. By the age of nine, I started wearing dresses; when I saw girls, I wanted to be one of them. I would sneak off to local woods, taking dresses and underwear. I would dress up secretly; it always carried an element of risk, and I was nearly caught on a couple of occasions. I’d also sneak into my parent’s bedroom and dress up in my mother’s clothes; I remember the horror of being spotted by a dog walker through the window.

At some stage, my mum found out and I was allowed to dress up in the front room, but I wasn’t allowed out. We kept things from my dad; he was ‘old school’ and believed boys should be boys and “man up”. We were uncertain how he would react.

Moving into my own place at the age of twenty-two gave me more freedom. I continued to dress at home; however, I was always careful and limited my dressing episodes out of respect for my mother.