My brief career in shop work ended in my early twenties in another town. Shop management was all glory and low pay. I took a job in a local factory with much better wages. I was also living Independently and for once l had money to spend. Some of which l intended to spend on cross dressing after l had seen it in imported ( and probably not legal at the time ) porn mags. Like many other people l had tried dressing in my mother's clothes and looking at the underwear section of her Littlewoods catalogue. Not very fashionable but a thrill all the same. I wanted to explore, and experience, and improve my knowledge of this aspect of sexuality.
My bright idea was to pretend to be going to a fancy dress party where everyone dressed in their opposite gender and buy my clothes at a charity shop. Easier said than done. When I ventured into one l found there were more people in than I'd hoped. Nevertheless I wanted to get an idea of what was available and I browsed the racks as secretly as I could as well as looking at everything else that was for sale.
My nerve deserted me and I went to leave, the manager approached me and a general conversation started. In it, he said that the shop was open late on Thursday, and that it would be a lot quieter. He also said he would be the only one working, so I would surely get whatever I wanted. Embarrassed l thanked him promising to return then. He obviously knew what l wante, but on the other hand he wasn't bothered. I made my mind up that l would return on Thursday.
It was with more confidence that I entered the shop late that Thursday evening. The shop manager, Craig, remembered me and asked what I was looking for. I stumbled about telling him about my fictitious gender swap party. He said lots of people shop here for that. He told me to help myself and try them on to see if they fit. Well, there was plenty of choice but a lot of it old fashioned. I selected a dark blue pleated skirt that I thought would flair out as l twirled and a white Lacy blouse. It occurred to me that getting nice underwear and stockings were going to be a problem, (there was no on line shopping then), but it was a start.
In the changing room l decided to strip down to get the effect, but in doing so, managed to get an erection, but when the ensemble was on and I gave a twirl you couldn't see it. I didn't think it looked too bad and I would happily wear it around my flat. I was lost in thought when Craig suddenly announced if everything was alright, and could he check if everything fitted? With that he pulled the curtains to one side and I stopped twirling.
My erection wasn't difficult to spot but he ignored it and ran his hands up and down my outfit adjusting it here and there. He even ran his hand over my rapidly deflating cock which made it twitch. Again it was ignored. In the end he tutted and said that it wouldn't do. He felt sure he could find something more age appropriate and instructed me to take off the outfit while he selected other items of female apparel.
He was bloody quick. I was just reaching for my underwear when the curtains flew open and l was standing there, stark bollock naked, with a cock that although subsiding from firm to soft showed definite signs of being inflated. Craig took a few seconds staring at me and told me he thought that if I was serious about cross dressing then I should try on the mini skirt he had in his hand. Obviously the party line l had spun him was not believed. He said he wanted to see if I had the legs to go with it. I'd lost control. He'd definitely taken over.
As it happens l did have the legs to go with it. Well, they were a bit hairy but that could easily be resolved. How did l know? Craig told me. He also said that if I was serious about cross dressing then he had other items he kept in the flat above the shop and that he was closing the shop in ten minutes. Would l wait? Yes of course l would.
I waited outside for Craig to go through the routine of locking up. I wouldn't say I was nervous but I was curious about what I would meet upstairs. What sort of collection of female garments did Craig have up there and would l like them. Five minutes later I was about to find out.
When he opened the flat door he indicated for me to go first by ushering me ahead of him using the palm of his hand on my bottom. I began to think that this evening was going to be more fun than I thought. I walked up the stairs steadily so as Craig could watch the cheeks of my bum, In my jeans, moving to the rhythm of the stairs as I climbed up them. I was now in a teasing mood and dying to get to know him better.
The flat, when l entered it, was very tasteful with well matched cushions and drapes as well as objects depicting art-deco figures, both male and female, in various states of undress. It was also lovely and warm and made my flat look dull and uninviting. Craig poured me a glass of wine and explained how he got the collection.
It seemed that the jobs volunteers, who help out in the shop, don't like doing is sorting through the clothes donations, so it always fell to him to do it. It wasn't always a pleasant job as some of the donations left a lot to be desired. These have to go to the rag man but it does bring in some money. So while he sorts out what can go out into the shop, and what needs to go to the rag man, items of interest to people like myself have often been found. These he hides and then washes when there are no volunteers on duty and brings up to the flat.
It transpires that Craig is good at identifying fellow cross dressers and many of them go to his flat and buy them. he money, he says, goes into the till. He does it for the sexual encounters he sometimes gets. It appears that not all crossdressers are in it for the sex but just for the love of having an alter-ego. Me, he thought, was seeking the sexual side of it. He was right!
