I have been wearing lingerie on and off for many years, in fact, since my teen years.
Possibly all started when I was around 5, my sister dressed me like a princess for her school play (a training bra, panties, and barely black tights with a midghtnight blue satin party dress).
From there, the seed had been planted. I just felt more comfortable and happy. It's weird, but all through my teen years I was crossdressing in my older sister's underwear (black bra, black thong, black stockings with suspenders). One day, she caught me dressed in her waitress uniform. She was angry but understanding. The day after she had bought me my own lingerie and underwear and handed me some of her old skirts, tops, and dresses, and also one of her spare waitress uniforms.

I was so happy when I first met the woman who became my wife, she quickly observed that I showed a keen interest in going shopping for clothes and that I had a good idea of what suited her, so much so that she’d often wait in the changing rooms whilst I’d select garments for her to try on. Very soon, she clocked my love for lingerie and surprised me when visiting with gifts of some lingerie she had purchased for me, including my first adult bra. After this point, there was no going back.