Many years ago I used to work on contract down in South Wales, I used to travel down on a Sunday night, so I would be there first thing in the morning on a Monday. The place I used to stay at were used to me coming in late and would leave the door unlocked, so I wasn’t on the clock or anything to be there by a certain time, as long as I was quiet when I got in.
One time I had driven over to Manchester in the afternoon and gone to the Transformation shop and had bought some new high heels. They were open Sundays. It was the pre-Internet era so don’t judge me too harshly for paying way over the odds! Under my drab clothing I had a matching set of lingerie and some very nice stockings. When I got back to my car I slipped out of my trainers and put my new heels on. I wore them to drive all the way down. At each stop I made I would slip my trainers back on, then put the heels back on to drive. As I was going down the A449 it was late, about 11:30 at night. There was a lay-by there with a toilet block just shy of Newport. having been there in daylight it was obviously a very popular dogging spot for all and sundry, but that night it was very quiet, seemingly there was nobody about, and I was absolutely busting. I pulled up shy of the block, slipped off my heels and left them on the back seat, put my trailers back on, and as I thought there was nobody about I did a bit of a mince to the toilet block. At the time I was very shy and naive, still pretending to myself that I was straight and trying to date women very unsuccessfully, but secretly in private was dressing more and more and struggling with thoughts about sex with men or other dressers.
The toilet block was very dark, very scary, And I was thinking rather than risk going in and getting my throat slit I would just go up the back wall and be done with it, nobody was about! When all of a sudden this much older gentleman appeared out of nowhere, he was tall and rather refined, he came up behind me and put his hand gently on my bum, I didn’t think anything of it, “why don’t you come with me to the ladies, the lights in their work, and it’s a lot nicer than in there”, that seemed really reasonable to me, and without thinking I said “oh good, cause I really need the toilet before anything else!“, He smiled and using gentle pressure guided me round to the ladies side of the toilet block. All the while as we were going there he was talking gently to me, asking me questions, and I was responding positively to him, with hindsight he was obviously chatting me up, he was guiding me with his hand on my bum, they were quite lightweight and I wondered if he would be able to feel the lingerie through them. He was obviously more dominant, and my natural submissiveness was flooding to the surface, and as I realised now I have a natural affinity to the well dressed, well mannered, refined silver Daddy types. He was asking questions about me having a girlfriend, and I was giving answers that could be taken as having no interest whatsoever in girls. Then he asked me if mine was the blue Cavalier, I said it was, and he smiled, he must’ve parked behind me, looked in, I’ve just told him I don’t have a girlfriend nor much interest in girls, and there are a pair of 5 inch high heels resting on the backseat for anyone to see, even in the lighting that was there they must have been obvious! The ladies side was much nicer, well lit, and clean, I rushed into a cubicle to relieve myself, as I shut the door I felt his hand pressure on the door as I closed it, I think he had expected to follow me in, but he went into the cubicle next to me and carried on chatting away, he must’ve thought he had struck lucky, finding a late 20s Submissive shy feminine, if not actually effeminate, sissy type younger guy who was responding very positively. Now I had emptied my bladder I felt much better, miracle upon miracle to taps worked and I was able to wash my hands, he was still chatting me up, but he didn’t make a move as such, he didn’t tell me to do anything, so it never occurred to me at the time that he might be interested in me, so I wished him a good night and walked out, I decided I would drive the rest of the way in my trainers, got in the car and drove off, leaving the poor guy probably very horny and frustrated, thinking that he was about to get lucky!
If only he had been more assertive, had to said something about seeing the high heels, if they were mine high heels, had asked me if I had pretty lingerie to go with them, and why didn’t I show him, then I might have overcome my nerves, certainly overcome my naivety, and something might have happened! Instead it was as I merged with the traffic I suddenly realised what had happened, there was another lay-by a few hundred yards further down the road, that I have really enjoyed his hand on my bum, guiding me about, it felt very natural, and very rising. So I pulled in there and waited, I wondered if he might realise I had had an attack of nerves. I was just an idiot, and that as he followed he would notice me but there and pulling behind me. But I expect he went back to his car hoping somebody else would turn up. I updated for about 20 minutes, and then carried on my journey off towards Swansea.
If that gentleman happens to be on here I can only apologise, I am so sorry for being so stupid and naive. I’m sorry if I left you hot and flustered, and anyone now hoping this was going to get really hot and heavy. |
