Written by James
8 Aug 2018
Best of Both Worlds as a CD pt 1
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9 minute read
This is going to be a long recollection, but now it’s in the open and my new partner now knows it all I can tell it to all.
I suppose you could say I have cross-dressing since the day I was born, as being a boy with 2 older sisters, I was their living doll. As early as I can remember I was dressed in girl’s clothes by them, even going to birthday parties as a girl in frilly dresses. All this did not excite me and I took it as normal.
So over the years I accepted the fact, until suddenly it stopped, my sisters had found boyfriends from the Church youth group. So at a young tender age, I suddenly found myself as a boy wanting to do boy things, this all went well until one rainy day.
Now I should add that although I was male I did not have much in the way of a male shape or indeed male hair. Anyway, my parents were out for the day shopping and the 2 sisters were out with their respective boyfriends, so I was home alone.
Bored on a wet Saturday afternoon I went into my sister’s bedroom, where I had happy memories of being a girl and started looking through drawers. My eyes were on stalks as I came across pretty underwear and stockings (it appears that our mother would not let the girls wear tights due to health reasons!). Within seconds I was stripped naked and dressing in matching suspenders and panties, even trying a bra on stuffing it with stockings. Looking at myself in the mirror I looked great, so over to the wardrobe to try a dress on. Now my sisters were roughly the same height and build as me so I chose a dress and shoes, I felt complete for the first time in ages. As with most girls, they got through clothes and shoes quickly, so raiding the discarded clothes bin I managed to amass a good selection of clothes, shoes and underwear, storing them in an old kit bag for me later.
This would now set my secret life to the present day, more of which later.
As was expected of me I also joined the church youth club and to cut a long story short met and married my first wife, Liz. I thought she was a good girl, but a soon as we were married she turned into a right nymphomaniac! All because I brought her a set of undies and stockings. As soon as she put them on, in the shop I hasten to add, she seemed to change. She wanted to go shopping and brought more of the same, ditching the tights (thank goodness) and the plain M&S undies. She started reading erotic novels and asked me to get some soft porn videos to watch.
Now by this time I was progressing through the bank where I worked, but money was always tight, we had enough to live on and enjoyed foreign holidays, where Liz enjoyed parading around in her tie bikini. One such holiday was to Dubrovnik, where if any of you have been there many of the beaches are nudist. Well we stumbled across one such beach and rather than turn back Liz wanted to see what it was like. We found a spot and settled down to observe discreetly, or so I thought. As I sat there looking at the beautiful people undressing I did not notice that Liz had stood up and stripped off displaying her body to the world, now this did excite me and I joined her discarding my shorts but lying on my back until the hard on disappeared. Needless to say now Liz had experienced being naked there was no going back. We made friends with a German couple, who fortunately spoke good English, and they invited us to join them at their hotels disco for their last and ours last night before flying home. Liz and I accepted, and we made plans for the night. Liz wore a lovely white cotton dress with white bra and thong. We met our new friends to be greeted by Helga in a white lace dress and nothing else, which showed off her all over tan. Liz saw my face and made excuses went to the toilet and promptly took her underwear off too, the thin cotton dress allowing everyone to see her nipples and pussy. As the evening went on we were joined by other couples and the wine and beer flowed freely. As the evening wore on the dancing was making us all quite hot in the summer evening, someone suggested a swim in the hotel pool and before you could say anything a couple of the ladies had jumped in followed by a few of the men. Liz just looked at me smiled and ran to the pool and dived in, climbing out the thin cotton dress was completely see through but she didn’t care. What we didn’t was that this group of our new friends from Germany were swingers and sure enough we were invited back to a villa which some of them had rented to continue the party. We were completely oblivious to what was to follow, as we entered the villa we saw people naked in the pool and in the rooms. Liz was so quick to strip off and enjoy the pool and the attention of the men and when I glanced over to see what she was doing she had a German cock in her mouth and another probing her pussy. I must admit this made me very horny and soon had a German lady bouncing on my cock. So that was our introduction to swinging and a new side to our life.
So back to my crossdressing life, when we got home to supplement our income Liz announced she was going to try stripping to earn some more money for us and who was I to object. Liz’s first attempt was at a pub in the city well known for letting amateurs have a go and to be fair she gave it her all, I was very proud of her for having a go. As she got better she decided to stop using everyday clothes and get some stage clothes, fortunately there was a shop in the city that catered for the exotic dancers based in the rear of a posh lingerie shop. The lady in the shop was to become pivotable in my life too. As Liz’s new part time career set off I was being left at home more as she travelled the county with her new found courage and eventually joined a travelling group who performed shows all over the country. So I was left at home alone again, but this time with even more gear to try.
I knew Liz would be away most Fridays and even Saturday nights coming home quite late but absolutely insatiable for sex, so I could have the whole evening and even in some cases the weekend to dress as a woman. Friday nights I would race home from work, strip, shower shave all over and dress as I wanted to just to enjoy the experience again as I did when I was a teenager. However, this time I was determined to go a stage further.
Now as Liz was away it was my job to go the lingerie/costume shop to pick up supplies, stockings new underwear etc. I was getting to be a regular customer of the shop and could often be seen browsing the lovely clothes and underwear so much so that the lady in charge came over to me one Saturday and took me completely by surprise by saying are you looking for yourself as well?
This took me by surprise and I hesitated and stuttered, I’ll take that as a yes she said, come with me to rear of the shop. She asked the assistant to look after the shop as we went into the exotic part of the shop. Now then she said, what are you looking for and what do you want to end up like. I hesitated, but then said I wanted to be able to go out as a woman. Right she said no problem, what do you wear at present, when I told he about my bra stuffed with stockings she laughed, what you need are these as she produced a pair of silicone stick on breasts which looked so real. These are for drag artists and ladies who have theirs removed so they have to look real. What about you tackle, well I said I am not that well-endowed so it was not to much of a problem as I wear a silk g string which I tuck my tackle into as wearing ladies clothes does not excite me in that way. She produced a pair of pants from a drawer which again drag artists use, these will pull it in and give you a smooth lady like look we even have a pair with a Brazilian look to them. And they come complete with a catheter to let you pee like a lady and an open rear end.
She encouraged me to try them on and then to choose a matching set of underwear, now what stockings do you wear, I was getting quite use to this treatment now and casually said just plain black, try these FF stockings they will look better on your legs. With all the foundation garments in place she chose a dress with built in hips to give me a more hour glass figure, a pair of shoes and a lovely blond wig. The assistant was called in and she did my make up, I was complete. Let me see you walk she said, as I had been dressing at home with Liz’s shoes I could walk easily in heels even sitting down with ankles together. Right she said go for a walk around the shop to see how you feel and to see if any of the customers can spot you. I did and they didn’t in fact one lady asked my advice on what bra was best. I came back to the rear said thank you and proceeded to get undressed, just then she produced a carrier bag with all my male gear in, off you go she said it will give you confidence. So there I was transformed and walking back across the city to my car as a lady just what I wanted.
Now to take it a stage further, in part 2 if you want, just to let you know I am writing this dressed as Vicki with my new lady correcting my spelling.