Craig the Charity Shop Manager

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!

He said that before he shows me the goodies would l be interested in seeing him dressed as a woman.

Yes please!

Telling me it would take about half an hour, he gave me a glass of wine and a number of magazines of a pornographic nature, some of them showed cross dressers, and one of them was a gay magazine. The pictures in them were unlike any l had seen at the time. The ones here, at the time, were of flaccid cocks. This one showed erect cocks, some of them were very big boys and I was glad they weren't coming anywhere near me. But wow, what a turn on. At the time these explicit publications were not legal in Britain but would have come here via foreign travellers or smuggled in off the docks. This made me so horny l was ready for anything that Craig wanted.

When Craig appeared it was as Christine, and bloody hell it was difficult to the see the real person underneath. She didn't look tarty or over the top, make up was just right, as was the jewellery. She wore a pleated black mini skirt which she said was A line, a white bodice that covered her new boob's topped with a white lace jacket that was see through and highlighted the flesh tones of her shoulders and arms. Her stockings (as I was later to find out) we're black and her dark red shoes, though heeled, were not the stiletto type which would have made her look tarty. She also carried a small handbag that had no strap which I later found out was called a clutch bag. All in all a very impressive sight and one l couldn't emulate without a teacher.

As she had introduced herself as Christine l took the hint and addressed her as that. I also decided to treat her as a lady too, and offered her a glass of wine. I took her hand and led her to sit beside me on the settee. This she did demurely. It was also a massive contrast to the assertive Craig in the shop. Still, using a demure voice, she asked me how she looked. I told her she looked fabulous and squeezed her hand. This made her smile and she said l was naughty. She was about to find out how naughty l would become.

For once in my life l took the initiative, and placed my hand on her knee and began to gently stroke it. The low soft sounds Christine made encouraged me to go on, and my hand went gently up her leg towards her thigh to discover whether they were tights or stockings. Brilliant, they were stockings.

My hand touched bare skin and the end of a suspender belt. Shivers ran down my spine and the level of excitement in me rose. Christine was getting excited too as she immediately placed her hand right on my thigh and wrapped her hand firmly around my cock. I couldn't wait any longer. I needed to lose my clothes and climb on top of Christine. I stood up and started to take off my shirt, then my trousers. then my underwear. All the time she kept her eyes on me, not looking away once. Her mouth immediately went for my flag pole of a cock and grasped it firmly between her lips.

The scene before me nearly made me cum but I now believed there was a greater prize, the one I didn't get from Damian. Tonight I thought I would get to feel what it was like to enter Christine and leave a deposit. I slowly withdrew myself from her mouth, got down on my knees in front of her sitting on the settee and let my hands slide up to her thigh slowly lifting the pleated A line skirt up and exposing a pair of black lacy knickers with a long sleek cock trying to escape from them. I helped with its escape only to trap it again with my mouth and began to slowly build up some momentum getting her more and more excited.

I noticed how Christine's hands went for her breasts and she began fondling them as if they were real. She really was into the female role and it was time to see if she was going to let me do what I wanted.

Taking my mouth away from her long and slender cock l began to encourage Christine to turn over and face the back of the settee and kneel on the floor. There were no objections and she was over in a trice. The black pleated skirt was draped over her bottom in front of me, and waiting for me to lift it over her cheeks and expose what I had been waiting for since Damian left. Taking my time l pressed my eager cock towards her bum cheeks but allowing the mini skirt to come between us. For me it was savouring the moment and at the same time giving Christine the idea of what was about to happen.

Slowly the skirt was lifted so the black lacy knickers were exposed, and after running my hands over them a few times, l started to pull them down and with the help and cooperation of Christine, all was revealed. At this point she pointed to her little clutch bag for me to open it. Inside was lubricant. It was the days before HIV so no thought was given to condoms. I willingly doused my very eager cock and her equally eager bum hole with the slippery stuff and gently pressed myself against her.

After running my cock up and down the crack of her cheeks, I felt where the entrance was and slowly started to push against it. She also started to push back and little by little l began to feel myself enter her. The sensation was fantastic. It felt warm and tight and the waves of pleasure it gave me ensured I wouldn't last long before erupting inside her.

I desperately wanted to take my time and enjoy the feeling that Damian must have had when he entered me. But the sensation was too strong and I found myself quickening the pace until I had no control over what was happening and an overwhelming desire to let go of my seed, deep into Christine, took over.

I confess that I had no notion of what Christine was feeling but my overwhelming urge to cum took over and with a deep thrust and a very loud grunt l came inside her. l had one of the best orgasms l had ever had. It seemed to last forever and left me shaking and very weak.

Suddenly I became aware of Christine wanking away while I was still inside her. The rhythmic movement of her pelvis added to the sensation of my post orgasmic come down and kept the pleasurable feeling going. With a sudden jerk of her own she orgasmed herself and I could feel her bum cheeks tighten around my cock. Fantastic! We both needed to get our breath back.

After pulling out and sitting back onto a chair l watched Christine clean herself up and finish dressing herself back to her feminine self. It was really quite hard to see her as anything else other than Christine, but with the added bonus of having a cock. I was encouraged to drink more wine but remain naked. Very soon afterwards l was led by my cock into the bathroom where l was showered and my body hair was shaved off including my pubic hair. A very sensual experience. Fortunately l wasn't very hairy to start with but by the time she had finished with me l looked pre pubescent and l have to confess I liked the look. Next l was dragged into the spare bedroom where all the items that appealed to us were either hanging in a wardrobe or displayed neatly in drawers.

It was astonishing to see. I didn't know where to look first. On the rails were dresses of all sorts of designs and sizes, some of them floral, some of them of a geometrical design. There were miniskirts, maxi skirts, more A line skirts and even some ball gowns, happily in sizes suitable for the larger lady and therefore ideal for a crossdresser.

The underwear was fantastic. They came in allsorts of colours and sizes. There were lacy ones, sheer ones and some with little bows attached. I asked Christine where she got all that underwear and she told me that often donations, usually jeans and trousers often had them left inside. She said that sometimes they were left inside men's trousers. Hopefully they were removed quickly and for happy times to cum that evening and just left there. Or, perhaps they were there to tease the charity shop staff!

There were even stockings there, new and in the packet. It seemed Craig had a friend who was a hairdresser and they sold them in the salon. Craig then bought them and sold them on for a profit. Another line he had, was the ability to use a sewing machine and he made suspender belts copied from ones he occasionally gets in the donations. Craig /Christine was a smart cookie.

An outfit was selected for me by Christine, but first I was shown a few tips about makeup. A number of powders and paints were applied to my face. Thankfully not too much. I didn't want to look like a geisha girl but one who could (if I was brave enough) venture outside and not look out of place. A look in the mirror with my newly painted face showed me how feminine l was becoming.

The outfit consisted of an orangey brown pencil mini skirt and a long sleeve pale cream blouse embroidered round the edges. The end of the sleeves had what I could only call a ruff that more than half hid my hands. The jewellery was a necklace of Stone and pearls but only at the front, laced through it by a leather strap. The knickers l opted to wear were a light brown edged with cream lace ( remember this was the seventies). Obviously I bought some stockings but had to borrow a suspender belt with a promise by Craig that he would make me one.

The shoes were again a bit of a problem. Not many of the sizes to suit men came in the shop so choice wasn't all it could be, but I managed to get a pair of slip on black wedge heel sandal type shoe's. The long hair worn by men in the seventies was easily taken care of by removing my sideburns and a little bit of restyling.

The outfit on, l was surprised how l looked. I definitely had a feminine look and my cock agreed, rising again as I looked in the mirror. Christine too clearly agreed as her hands stroked and smoothed my costume and smiled a great deal.

I couldn't help but touch myself and increase the sexy feeling l was getting. The next surprise l had was Christine produced a Polaroid camera and offered to take some photos. I was so surprised and pleased by my girlie look l readily agreed and l spent the next half hour posing and pouting on the stairs deciding which ones to take. The results made me smile especially the one taken from the bottom of the stairs and me climbing them and showing the tops of my stockings. Very sexy!

The evening finished with more wine and Christine struggling to get my pencil skirt up to my waist and exposing my new prepubescent cock and ball's to her mouth. She was determined not to let go and sucked and chomped away on it for ages until I could bear it no longer and came deep into her throat with a not so feminine roar. Not a drop was spilt judging by the contented smile on her face and l felt compelled to kiss her.

I left Craig's flat a little worse for wear alcohol wise. Atlas still wearing my girlie knickers and stockings and suspender belt, praying l wouldn't get run over and have to explain to hospital staff why I was wearing them. Nevertheless, it was thrilling at the same time.