It all started as a punishment when I was about 13. When I had done something wrong in her eyes mother dressed me up completely as her pretty daughter. And as our family was seriously wealthy she did it in style and costs did not play a role she really went all out with it. It was pretty partydresses, beatifull wigs, expensive shoes and all the trimmings. I was quite a slim puny boy with soft features so the result was impressive to say the least. Initially I found it all horrible and cried a lot and tried everything not to displease her and get punished again but in the end she always found some reason as she sort of had fallen in love with the idea of me as her glamourous little princess. After a while I kind off reconciled myself with my fate and almost started to like it as the awfully pretty girl in the mirror kinda awakened sexual feelings in the pubescent teen I was. And then there were the sensual feelings the clothes themself provided, the feel of silks and satins on my teenage body, the restrictiveness , the heels, the stockings. It was both confusing and exciting. Of course mother encouraged and stimulated these feelings. And she didn't stop at the clothes, it was deportment lessons, speech lessons, ettiquette and what she called girl lessons in which I was actually taught how to think as a girl by reading certain romantic books and magazines. By this time I was a girl most of the time when I wasn't at school.
By the time I was sixteen I was almost completely brainwashed and mother loved it. The partyfrocks had become classy designer cocktaildresses and promgowns and the heels had gone from 3 to 5 inch. The undies had gone from girly to stunningly glamourous and sexy. At that time mother also decided that I had to get used to the presence of boys and men so she encouraged her ladyfriends to bring their sons, nephews and other familymembers along when they would visit us. At first this really scared me and I cried and begged her not to do this to me but she was relentless. At first it was just them being there and seeing me but in time she started to encourage them to sit close to me and actually instructed me to flirt with them and make contact.
When one of these boys seemed sufficiently interested and found her approval, she would blatantly invite him over again and set up a sort of chaperoned date where I was glammed up completely, make-up, hairdo, wearing my sexiest eveninggown for my "boyfriend",who was a shy and unexperienced young man and totally nervous at meeting a stunning sophisticated young lady like me. These evenings were spent teaching us youngsters how to behave on a date. This went from holding hands, him putting his hand around my waist an holding me to giving eachother furtive little kisses. Later in the evening we would learn to slowdance with mothers very specific instructions how to hold and caress eachother, look into eachother's eyes and behave as a couple in love in general. If this all went well we were back on the sofa for the final act of the evening. The deep sensual kissing and making out scene. If mother was convinced we were doing it right she would leave us alone for a while so we could practice being in love as she called it. By this time my conditioning and girl lessons had me reacting to the situation as any delicate sexually awakening teenage lady would. I loved every minute of it and moaned softly under my "man's" kisses and caresses and was actually close to orgasm. Mother had won and and at that moment I never wanted to go back to being a boy ever again.........
Part 2
.....After that first experience mother was of course totally delighted with my initial reaction. I myself was both excited and terribly confused but I didn't get much time to think about it as mother wasn't finished with me yet. From that moment onward I was to be a young lady permanently and mother actually made me burn all my boys stuff myself in the back garden. I was now completely immersed in a world of femininity. My closets were filled with skirts, blouses and row upon row of the prettiest eveningdresses, ballgowns and cocktailwear. I had more highheeled shoes than any girl I had ever known and my drawers contained nothing but the finest undies all in silks satins and lace.... I was also taken out of school to be homeschooled, which mainly consisted of learning to be a complete utterly feminine young miss of good standing. Never got to see the boy again as mother had more grown up partners in mind for an eligable classy young lady like myself and didn't want me to be tied to a permanent boyfriend before I had some more experience in dating matters.
At that time mother's friend mrs.Franklin started bringing her older brother George along when visiting. George was a much older man and I was to treat him like a friendly surrogate grandad. This meant me going all girly and flirty around him whilst keeping up the appearance of it being totally innocent. I was to give him little kisses on the cheak at arriving and going, sitting (too)close to him, accepting compliments and little presents and letting him caress and innocently hold me as any loving grandaughter would. I was to be a serious tease. Contrary to my earlier boy admirer George had been briefed on my little secret but according to mother he had said that someone who was as feminine as me could in all honesty only be regarded as totally female and should be completely respected and treated as any young lady would expect to be treated.(and I should mention that George was in no way a gay man).....Even though it was initially all kept very innocent I realy enjoyed my role and to my surprise started to get disturbingly erotic feelings for this elderly gentleman. The attentions of this experienced manly man sort of gave me goosebumps and made me feel even more feminine and sexy than I already did.
I guess mother had noticed this and actually encouraged it. As George was quite wealthy and a rather handsome well dressed man (for his age...he was in his late sixties), mother thought he was a bit of a catch and again set me up to get closer to him. She innocently had him and his sister over for dinner and cocktails. We were all dressed up to the nines in glamourous eveningwear and it was all a very festive and classy do untill mother found an excuse for her and mrs. Franklin to leave me and George alone for the evening(think it was something like a friend falling ill). I had beforehand already been instructed to be very very sweet to George tonight and to get romantic. Outside my knowledge, and in not so many words George had been told about me having a little crush on him. So using my experience of my earlier date together with my flirting and teasing lessons (and a few drinks) it didn't take much time before George took me in his strong arms and gave me my first romantic kiss. I was totally blown away by the feelings this elderly man awoke in me and I couldn't help returning the kiss as passionately as I could and clinging to him fervently to continue this romantic mouthcontact. My arms were around his neck caressing him and I was softly moaning inbetween kisses whilst George whispered sweet words of love in my ears. This continued for the rest of the evenng without either of us going further than sweet caresses, deep passionate kisses and a gentle hand on my nylonclad knees. We didn't let on much when mother and mrs. Franklin returned and we said goodbye with a little loving kiss on the lips but the triumphant smile on mother's face told me she knew exactly what happened..................
