Gina

I had met my mistress on a local group on a kinky online platform as a 17 year old boy with a bit of a dirty mind and  soon got kinda hooked on exchanging online messages with this beautiful and obviously superior woman who seemed to like making me doing embarassing and even quite humilliating stuff like wearing mother's filthy panties I had to  secretly take from her laundry. Over time this went on to bra's , slips, tights and more. I had to deliver proof of these activities by sending her pictures of myself posing dressed in these items which I dilligently did. This went on over several months up to the point where I was regularly dressing up completely as a girl for the sheer amusement of this strange woman who subsequently re-baptised me Gina as Gene obviously didn't fit me. By then I was actually buying my own ladies things. I  even bought a rather pretty cheap blonde wig online. 
And then Mistress dropped the bomb! Mother had found out about our little game and had actually contacted her. Although my rather formidable mother had been partly responsible for my fascinations  both  through her general demeanor as well as having punished me by making me wear girls panties on a number of occasions, this initially scared the hell out of me!  It got even scarier when Mistress told me mother totally loved  my girl pictures and was totally in support of my ongoing feminization.  That is how and when it all started and got serious as later that week the ladies  met and they basicaly  laid down the law and started planning the 'wonderfull' new life they had in mind for me.The first time I  timidly appeared before the ladies in girl mode, almost shaking..., mother seemed absolutely delighted but also remarked in her haughtiest tone of voice that we still had quite a lot of work to do.  Over the next few days  quite a few bags  with the labels of the more exclusive fashion stores, shoeshops and lingerie departments started to appear in my room. Mother was obviously taking this all the way as there were items of clothing I had never seen or even knew existed and highheeled  shoes I was sure nobody would ever manage to walk in ,The main thing that changed however was having to dress as a girl permanently from the moment mother got involved . And you could learn towalk in the forementioned  shoes as I  soon found out after walking in them around  Mistress 's large townhouse, where I now had my own very feminine room, for most of the following week.... And there were girdles with real nylons and  pretty silky nighties  for bed.  And make-up and salon-nails.  It had been all  so overpowering  in it's completeness. Mother and Mistress had taken over in a truly monumental way. It wasn't just regular girl clothes, it was all high fashion, pretty satin blouses, tight pencil skirts, glamorous cocktail dresses and all the appropriate accessories and jewelry.
Obviously I wasn't going to become 'just a girl', as both the ladies made it quite clear that I absolutely had to become the ultimate 'little lady', a hyperfeminine glamorous society miss. On top of dressing me up, the ladies took turns instructing me how to walk, talk and in all aspects behave like the ultra feminine debutante they wanted me to portray. Soon I was mincing around the house daily and as elegantly as possible in the highest of heels in a very narrow knee-length  pencil-skirt untill it became second nature. I had to learn how to sit down, how to cross my legs in a certin alluring way up to small things like adjusting a strand of hair or timidly fluttering my (false)eyelashes. About a week into mother's reign I had found myself in the back garden ritually burning all my male clothes whilst the ladies were cheering me on enthusiastically. Naturally I had to show the same enthusiasm myself as neither of my lady-benefactors was above delivering me a sound spanking on my pretty silky knickers as I had experienced before. Although I wasn't ready to admit it at that point, secretly there was a part of me that actually actively supported the ladies  disquieting plans for me. 
 Mother had also roped in a ladyfriend of hers who in a previous life had been a voice coach to teach me how to convincingly speak like a young lady. It hadn't just been about raising my pitch, it was mainly the general manner of expressing myself including the type of words women and girls tend to use. The pitch of my voice, according to my teacher, was not of that much importance as plenty very attractive and elegant ladies did very well with husky alto voices. The main thing was to learn to speak in a gentler softer voice and learn to form the words in the front of ones mouth instead of in the back of the throat so not to produce that typical male resonance in ones speech.
Now, over 2 months later I was almost completely reprogrammed and even if there ever had been any resistence to the ladies machinations, I was completely with the program and convinced it was all utterly delightfull and right. I just couldn't help it. For some reason we find it much easier to do and think what we are told than to make these decisions and choices ourselves. Especially if these decisions and choices are made by someone who we implicitly trust to be right like my rather formidable mother and my mistress. In the end the things we are made to do or feel are not our responsibillity anymore and that almost results in a feeling of freedom... As long as those things don't clash too much with more deepfounded needs or wants we may have, not being responsible for ones actions and behaviour is a hell of an attractive concept. ....................You must understand that ever since my early teens my secret dreams  and  fantasies had already featured a  strange world where these beautiful but seriously depraved older ladies, for their sheer amusement, kept me in delicious captivity dressed in the most exquisitely feminine  girl's  clothes and high-heeled shoes and then laughed at my pretentions of  actually being allowed to be a boy In said scenario I was a toy for  their perverted sense of amusement but these fantasies still thrilled me with strange delightfull emotions. To think of myself  forcibly dressed in the exquisitely pretty eveningdresses and silk undergarments of an ultra-feminine young lady, undergoing punishments and  dainty tortures at the hands of strong dominant woman deaf to any protestations, had been completely intoxicating. Of  course  in the past, when I could still see myself as an otherwise  relatively normal  young man, I  had  fought  these  clearly unhealthy thoughts and  fancies but they always returned and seemed to almost be part of my nature. So now my wonderfull mother and my equally magnificient mistress had virtually made said dreams come true in real life, it should be clear to everyone to that I wouldn't be able to resist the silken and satin delights that were on offer for very long. And the ladies made sure there were plenty of exquisite temptations to be had. Nothing but the best was good enough, half the time I looked like I stepped right out of a fifties edition of Vogue magazine. How many young ladies of any gender have ever worn a dress by Yves Saint Laurent, let alone have 2 of them hanging in her walk-in wardrobe? All my clothing and underwear was now exclusively made of slinky sensuous materials like satin, taffetta and shiny nylon and stockings and stiletto's were now compulsory 24\7. Mother ensured me my calf muscles will soon completely adapt to such footwear and in the end our 'Gina' will probably only be able to walk in shoes that have at least a 5inch heel. The slinky materials now almost permanently enveloping my body in combination with the sensuous feel of nylon stockings and almost debilitating footwear already seemed to keep me in a permanent state of delightfull sensual erotic turmoil.
Over the past few weeks 'the ladies', both Mistress and my dear mother, had been going on and on about how, if I really wanted to become the ultra-feminine little lady they had so generously allowed me to portray, I should learn to be much more aware of the effect a pretty miss like me would have on the men in her presence. Consequently I should also learn to be conscious of what my actions, poses and movements would do to them. "You need to learn all  about the joys of being helpless, beautifull and desireable for your man and eventually you must accept your new role so completely that you will even delight in at least pretending to completely submit to your lover's ardent manly desires and needs." According to Mistress, boys with my particular disposition would already know what effect they would have on men when he crosses his perfectly smooth nyloned legs with her incredible stiletto heels in a certain provocative manner(as these fascinations have in most cases already driven them to to their dressing up adventures in the first place). Off course she was right as such things had more and more been on my mind during my adventures in front of the mirror.  Naturally this meant that at some point I  absolutely had to start meeting men, and preferably getting  romantically involved with a suitable interested gentleman of their choice. And most recently the ladies disclosed that they found a possible candidate in a certain gentleman called Mr. Leo. The story was that said Mr. Leo was  one of Mistress's 0ther kinky online 'friends', who had at some point confessed to having a secret fascination for ultra-feminine crossdressers and even though Mr. Leo was a rather mature man, his gentle demeanor and handsome, rather aristocratic, appearance made him the perfect candidate in the eyes of the ladies. There seemed no way out of this even though I still didn't feel like gettng romantic with a man, especially with an obviously slightly depraved old man. As expected the ladies weren't giving in that easily and they turned up their efforts in convincing me how in the end I would love the act of seducing him and the sense of being desireable coming from it. Finally being in the arms of my ardent male suitor would make it all clear according to the ladies who up to that moment had always been right about everything.... These wise lessons in feminine romantics went on and on and on and as so often my mind capitulated and decided to believe these wise ladies unconditionally.When Mistress had finally allowed me to view my mysterious date's profile picture I found that the mysterious Mr. Leo had actually been the rather imposing headmaster of the primary school I once went to. The ladies had clearly been right once again as even though he must be at least in his late sixties by now the idea of seducing him was definitely growing on me. What finally got me on board was something Mistress had once brought up during our online games, the principle of 'deliciously wrong'. Basically it's about things or situations not being exciting despite of being somehow wrong but very much because they are deliciously wrong. After my mistress had showed me how completely and utterly wrong my getting romantically involved with this man could be in this context. Really, this young ultra-feminine crossdressing 'lady' made to fall desperately and almost sickeningly sweetly in love with this silverhaired casanova, who was a rather conservative-looking gentleman and old enough to be her/his grandfather?  Such a delightfully wrong picture, wether it was completely honest or just an act of sorts...                                          
My personal kinky mind really got this idea and from that moment I decided that I was game to completely inappropriately fall deeply in love.

When the time came, the ladies took hours grooming me for my wonderful date. My own now shoulderlength  hair was in curlers, they had done my nails and make up and they'd helped me get into the extravagant organza designer gown they bought me for the occasion. Meanwhile Mother's devilish seductive voice was still  relentlessly instructing me how to behave and especially how a lucky little lady like me should feel and think on such a woderful romantic occasion. This went on and on for ages untill I seemed not to have a thought or a will of my own anymore. The ladies really knew what was good for me and by then I truly felt like a princess awaiting her wonderfull prince. It all felt so right, and I loved them for making me see their way.
The actual date was to take place at a fancy restaurant downtown where Mother, wearing a wig and tinted glasses, had secretly reserved a nearby table and silently sat watching the complete show! (Mr. Leo had up to then only had met Mistress so Mother could be 'a fly on the wall' here). Miss Gina's date, a tall rather distinguished looking gentleman in an expensive suit and tie,  had been eying the glamorous young miss sitting at his table looking very much like he won the lottery.  - Although I vaguely recognised him and for a moment feared I would be recognized, I still ferociously flirted with the older gentleman just like  the ladies had trained me to. I just couldn't help it -
Watching the whole play, they so carefully planned, unfold for real, was getting Mother very very excited.  She later admitted to Mistress that she actually had felt her panties become damp as she saw our couple playing footsie under the table and then saw miss Gina's date gently caressing miss Gina's stockinged knee.  'Miss Gina' was perfect, it looked very much like there was nothing left of his/her earlier fear and reluctance, and she was all coquettish gestures and furtive touches, just as Mother and Mistress had ordered. This was going even better than she had originally hoped ! It was a total delight to watch. When dinner was over and our lovebirds left the restaurant, the distinguished older man holding his date posessively around the waist whilst our little lady was almost devotedly looking up at her mature beau, Mother followed the seemingly very enamoured couple out to the parking lot where she found the two passionately making out, the older man pressing our little lady against his car as he aggressively kissed the beautifull pretend girl. 'miss Gina''s arms were tightly wrapped around his neck, clearly welcoming her elderly admirer's avid avances. After what seemed like almost half an hour or so, the obviously excited elderly gentleman helped his beautiful conquest into his car.  Soon the two would be back at the gentleman's home or hotelsuite, where a very willing 'miss Gina' would intimately pleasure his date with his beautifully manicured hands or even his glossy red lips.  As Mother watched them drive off, she actually almost had a spontaneous orgasm just by picturing how her darling former son could soon be devotedly sucking on his/her mature suitor's penis or even .......... It was all so Romantic and so Delightfully Wrong.