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’
I set my camera rolling and started walking up and down in front of my car, stopping every now and then to adjust my stockings and pout at the camera when, to my sheer horror, I saw a man standing, looking straight at me. I hadn’t seen him due to the glare of the headlights, a schoolgirl error. I went to get into my car, shaking like a leaf, I stopped, opened the door and looked up one last time to see that he was near my car and smiling. I don’t know why I did it, but I asked him if he had ‘enjoyed the show.’
I think it was now that he realized all wasn’t as it seemed, but he answered, “very much thanks, hope to see it again sometime.” He then went to walk back to his lorry. I closed the door to the car, without getting in it and walked after him, he turned and saw me walking behind him but didn’t stop. He got to his cab and climbed in.
I arrived at the side of the cab and looking up at him, I realized he was older than I’d first thought, maybe about fifty, my age. He put his finger to his lips, as though to tell me not to talk, then pulled his jeans down around his ankles and started to stroke his cock, all the time looking down at me. I think he was quite happy just to carry on, but I wasn’t, I climbed up onto the step and grabbed his cock with one hand, steadying myself with my other. He gasped and let me carry on.
His cock wasn’t huge, about seven inches and not too thick either,.I even thought that it would be just right if tonight was going to be 'the night' that I popped my cherry (it wasn’t.) I then got into the cab, crawled across him, in a not very ladylike way, until I was kneeling on the other seat. I bent down and took his now, pre-cum filled member into my mouth.
His cock didn’t taste as I thought it would but I didn’t care. It was a little stale at first, but, as I licked and sucked, that taste was replaced by the sheer, overwhelming desire for him to cum down my throat. It didn’t take long before I got my wish, being a novice I didn’t realize that the ‘twitching’ that was happening was a sign of what was to come. He jerked and arched his back, all the while holding the back of my head. He came with such force I thought I was going to choke, but, being a good gurl, I managed to take most of it, with just a little running down my chin and onto my dress.
I could sense that this was time to leave, as my ‘conquest’ was now looking rather sheepish, and obviously didn’t fancy a post-coitus chat. I got down from the cab as ladylike as I had got in, being hindered by the erection in my knickers. When I got back to the car I leaned against the side, got out my cock and after about ten strokes, shot the load of a lifetime all over the door.
Whilst driving home, still in a bit of a daze, my wife rang me to say that she was having an amazing time and asked if I had enjoyed myself at ten o’clock. I then realized that at that time, I probably had another man's cock down my throat. I told her that yes, I’d had a VERY nice time.
