A Chic with a Dick !                   by: Jannine

As a small child my mother always dressed me in girls frilly clothes and as I grew it seemed the most natural thing in the world to wear knickers and a frock. Every day when I returned home from school I would go straight to my room and take off the hated trousers and boys underpants. On would go a beautiful pair of frilly knickers and a dress, together with girl’s socks and sandals. Sometimes I would have to wear ordinary navy blue school knickers, because it was wartime and mum was not always be able to buy really girlie things, which she liked me in so much. I would then go out to play. All my friends just accepted that as normal because I was always dressed that way for playing out, the only difference was that they would call me Janie instead of John. As we grew older we all played together in the park on a Saturday and Sunday. We used to play all the normal games that children played in those days of innocence. However, it was inevitable that as we grew older we became interested in what were under each other’s clothes. As a boy, I was of course very aware that I possessed a penis and that wearing girl clothes were not really quite right. That did not seem to matter at the age of eight but when my eleventh birthday passed by it was then that the exciting feelings started to happen inside my knickers. The boys in our gang treated me as a girl at home and as a boy at school. I was very lucky that I had always been dressed as a girl and everyone I knew accepted it as normal for me. When the boys started putting their hands up skirts I was not left out and they soon realised that rubbing my penis up and down was as nice for them as it was for me. I didn’t really know what to expect but the feeling was lovely. I was about eleven years old by now and when I had my willie rubbed up and down it felt that the thing would explode. All the other girls joined in the fun and we all explored each others body as a matter of course, Then one day a huge, wonderful feeling came over me and I experienced my first orgasm. The boy, Johnny, from along the road, who had rubbed me up and down me that day, was so surprised as my cum went all over his face. It runs down his nose and he found himself licking it into his mouth. He really liked that and every time we went to the park, he would run his hands up my skirt, find my willie inside the frilly knickers that I was wearing and suck me off till I came into his mouth. After that it did not take long to find out what the girls liked, so we ended up doing each other. This all lasted until I was about fifteen years old and by then I had settled down to having sex with girls and letting my boyfriends masturbate me when I was on my own with them. I still had to dress in knickers and frocks etc. at home. Mum used to like me in girlie things far better than boy’s clothes. Mum would always go to the shops on her own to buy my girlie things but I could always ask her to buy me anything that I had seen in shop windows and which had taken my eye.

I should, at this point describe myself to you, so that you can picture me in your mind’s eye (and perhaps cum a little bit). I am nearly five feet ten inches in height and my weight is perfect at just ten and a half stone. I have long slender legs and sitting on top, a neat, tight little bum. My breasts are a girlie thirty-eight "B" cup and fill my bra to perfection. I am really very affectionate by nature and respond very sexily to any affection shown to me. The things that turn me off men are beer bellies, beards and moustaches.

Although I had no breasts to speak of at that age, I used to like to wear a lacy bra stuffed out with a couple of hankies. At least it looked like I had some titties. These days I have developed beautiful little breasts all of my own and they fill a 38 "B" cup bra nicely. The group that I hanged out with started going into the local pub at lunchtimes and early evening and we soon found ourselves talking to some fellas who were about ten years older. One of them, Steve, who was a fire fighter, took to me and offered a ride on his new motorbike. I was thrilled and did not hesitate to say yes to Steve’s offer.

That Wednesday was a lovely sunny day and Steve powered his bike into the countryside at eighty miles an hour until he stopped in a country lane somewhere near Oxford. I was feeling really horny during the ride so when Steve started to rub his hand up and down my thigh I really enjoyed it. When he realised that I was beyond the point of no return, his hand unzipped my trousers and wrapped around my, by now, fully aroused cock. Steve was very experienced at this and he gave me the most wonderful wank I have ever had. >From then we used to meet every week and Steve would show me a really good time. He would buy me lovely presents and take me to expensive restaurant’s to eat. One day he asked me to go with him to his house as he had a special present for me. When we arrived at the house, Steve showed me into his bedroom. Laid out on the bed was a beautiful outfit of girlie things. The outfit consisted of: White lace trimmed panties and matching bra. Suspender belt and a pair of black stockings. A grey pleated skirt and a white blouse. A pair of black patent leather girls shoes with lovely silver buckles. Steve said he would wait downstairs for me while I changed into the lovely clothes he had bought for me. I was so excited that I was oozing cum into my pants and Steve could see how pleased I was and I just had to dress up in this outfit. I undressed straight away and began to pull on the panties. As I put each garment onto my slender frame I was able to watch the transformation in a full-length mirror in Steve’s wardrobe. I knew that Steve would be delighted with the end result and when I went downstairs into the living room. I made a real impact on the rest of Steve’s family, his Mum and another brother and his teenage sister. Of course I was not embarrassed, because for me, although the clothes I was wearing were special, I was quite comfortable wearing frilly things and girlie clothes. I looked terrific and I felt very, very sexy. I knew that every eye in that room was on me and Steve could barely keep his hands off. His family knew he was gay so there was no problem about him taking me to his home. We sat and spoke while Steve’s mum made a cup of tea and I could see Steve getting more and more impatient to go upstairs with me. I was sitting there getting hornier by the minute and Steve’s teenage brother was looking at me with pure lust in his eyes. His name is Ian and he was about the same age as me at the time, seventeen. Ian was trying to edge his way nearer and nearer to where I was sitting on the settee and I could see that he was really intrigued about what was lurking in the frilly knickers he knew I was wearing. He had never seen a transvestite before that day and the thought of a boy dressed up and looking as sexy as I did, really was turning him on. He managed to get close to me and managed to slide his hand under my skirt and reach the edge of my knickers but when he tried to go inside I moved to stop him going any further. I could see the look of disappointment on his face but I had to be true to my Steve. Although Ian was a nice looking boy he was really to young to know what to do with another boy and any way, I was devoted to Steve at that time.

My favourite outfit is "Teachers Pet". This is a really sexy outfit and my ambition is to be seduced by Colin while I am dressed as "TeachersPet". The outfit consists, from the inside out, Navy blue frilly knickers, 40 denier Lycra & Nylon tights, Lacy underwired bra and on top I wear a light blue girls school uniform shirt and navy blue pleated mini skirt, Sometimes I wear knee high white socks instead of tights but wifey does not like me in socks so I only wear them when I know she will not see me.

Being a "Chic with a Dick" is not easy, it has taken me a long time to reach my present state of near perfection. Growing my breasts has taken the longest, but these are now so lovely and responsive that all the time and effort has been worthwhile. Keeping unwanted hair at bay is also a painful process but a really essential one.

Although I am married, I dress in girlie things whenever I feel like doing so, almost every day that is. My wife does not like me when I am dressed, although I think that she secretly likes to see me and I know that she keeps a close eye on my wardrobe and knicker draw so that she knows what I wearing underneath.

I do all of my own shopping in stores like the Secrets department in Dorothy Perkins, the lingerie section in C&A etc. I find that the maturer lady assistants and the girls in the shops where I go always help and advise me. I think they get as big a thrill serving a transvestite as I go shopping for frillies.

My breasts are now a nicely plump 38B and I have no need to pad them out, the only thing that would enhance them now would be highly desirable ‘Wonderbra’

 

 

© 2001
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