Heels Stories

When I wrote about my first toilet block experience, I mentioned one of the guys that I met was called Mark. He was a respectful lover and had offered me his phone number before he left. I messaged him a few days later and immediately regretted it, thinking that I was just someone to ‘chalk off’ from a toilet encounter and that remorse would prevent him from wanting to be the same CD again. After a while, though, I did re...

After indulging my fantasies of nylons, lingerie and heels on my own for some time, I decided to be brave and see if I could be ‘used’ whilst dressed in my girly clothes. I’m not a convincing CD, so I wasn’t going to hit the streets looking for attention, so I decided to see what happened on one of my business trips, which seems to be a standard approach for discreet crossdressers. As I travel for work, I will often bring...

This is not a raunchy story. I just wanted to share my journey to crossdressing and, once shared, it may encourage me to share some other stories relating to my obsession with nylons. I’ve always been into nylons and high heeled shoes or knee high boots since I was a child. Never having a sister meant I only got access to tights and stockings once I started dating girls in my teens. I’d always loved the look of nylons on...

I will always remember it, they say you do, you know first times, first car, first kiss, fisrt sex. Well this was first time walking down the road dressed as a woman. I was eightteen and no real idea what I was doing, my real prize possesion was a pair of size 9 heels, not easy to come by but made me feel so girly, they had thin straps that came up and buckled round the ankle, black shiney leather looked cheap and most li...