I have been crossdressing since my mid-teens, from sneaking a pair of my sister's knickers to sneaking into the gardens of my parents' neighbors and pinching underwear from washing lines. In my late teens, when I found girls and sex, I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down and got married.
Unfortunately for me (or not?), my wife liked to wear very sexy underwear, stockings, and very revealing outfits. This meant there were a lot of these ‘things’ around the house. It started small, again; on a day off I would be doing some washing and find myself holding the knickers against myself, then wearing them. Before long, I was back to a full ensemble, masturbating furiously.
My wife soon found out what I was doing and, instead of disowning me, like I thought she would, she said she understood and would help me out. Before long, I had a drawer full of my own clothing and even a couple of pairs of five-inch stiletto heels - one black pair and a pair of bright red Mary Janes, my favorites. The only stipulation she put on the arrangement was, that I only dressed inside the house and if she was with me, not in our bedroom. I obviously agreed.
This arrangement went on for quite a few years and to be honest, it was all I ever wanted.
Whilst on a night out, she would say to me, “when we get home we’ll ‘get comfortable.” She knew this would get me going.
On arriving home, I would proceed upstairs and dress in one of my many outfits, then we would have the most amazing sex. I have been a little vague up to now, so as not to get the reader too aroused, as this isn’t my main story, just an insight as to what got me here.
My story starts when my wife went away one weekend, on a girls' hen night. Just before she left, she whispered in my ear, whilst stroking my cock through my jeans, that if I dressed up tonight, at ten o’clock sharp, she would go into the ladies wherever she was and stroke her clit, thinking of me doing the same. I nearly came there and then.
Around eight o’clock I started to get ready. I was so excited. I was ready for about eight thirty, walking around the house. I kept walking up to the tall mirror in the bedroom, looking at myself. I was quite happy with what I saw. I was wearing a red skater dress, which just covered my thighs. I had on a very silky pair of red knickers, my stockings were natural, glossy hold-ups, with a very deep lace top and the heels, had of course to be, my five-inch, bright red Mary Janes. I put on my blonde shoulder-length wig and did my makeup as best I could. This was one of the things my wife always did, but I was getting better at it.
While I waited I got a little impatient and decided to do something that I had always wanted to. As it was dark outside, I thought how naughty it would be to go for a quick drive. I had seen some youtube videos of Gurls walking in front of their cars down quiet country lanes.
I drove to a local industrial estate that, as it was weekend would be deserted. I drove around for a short while, before parking up at the end of a quiet street. This was where they park the lorry trailers when not in use. What I didn’t know, was that not all of them were, ‘not in use’