He never had a chance -Part 2

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advanced training

Clearly mother's machinations towards establishing my desired romantic feelings towards these gentlemen did not mean that my other lessons regarding my feminine education were suspended. My days were thus still filled with being instructed on how to sit, to stand up and walk elegantly whilst giving the impression of effortlessly managing either impossibly narrow pencil skirts or voluminous ball gowns with a cloud of luscious frothy petticoats. And only when mother was in a particularly benign mood was I allowed to wear my now almost comfortable 4 inch heels but in general my Louboutin pumps with the 5 inch heels were the rule for my exercises. I was taught how exactly to carry my handbag, how to move and hold my arms and almost suggestively sway my hips and wiggle my behind. Apparently a large part of being a 'lady' is pure acting. The supposed natural elegance of women that seems so effortless is in reality quite hard work. The fact that it looks effortless does in no way mean that it actually has to be so.  For instance walking in heels is never a skill one is born with, it takes training. Hours of it. And there is more as one moment one may have to elegantly and effortlessly cross a room whilst the next moment the situation may ask for you to act as if you are teetering insecurely in your heels so the gentleman you are with can support his overtly feminine and delicate companion by offering her his arm or even holding her. Even fluttering ones eyelashes is a learned skill and don't even start me on just functioning like a normal human being with those inch long salon nails...Giving the impression of being born with such skills was everything. My tutoress was absolutely relentless. Additionally mother had roped in an old friend of hers who in a previous life had been a voice coach and speech therapist to Hollywood movie stars 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 tend to use. The pitch of my voice, according to my teacher, was not of that much importance as plenty very attractive and elegant moviestars 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. Easier said than done of course but eventually after weeks of practice and relentless training I had supposedly improved so much my coach thought it would soon be time to put my new skills to the test and what better way to do that was there than letting me actually talk to the gentlemen I had up to then only exchanged written messages with on the phone. Mother liked the idea but she didn't want these strangers to become more than practice material (she clearly wanted and planned a far less random choice of gentleman for my first date once the time was there) so she got me a safe phone with a secret number so not to give away too much private information. Obviously both my tutor and mother would be closely monitoring my conversations. I would get instructions on ....everything basically. I was told what to talk about and what my attitudes should be. I was to play the still slightly apprehensive innocent virgin who was still overwhelmed by these 'new' romantic feelings I was experiencing, almost forcing the gentleman into the role of the gentle understanding uncle. At the same time I was still expected to innocently keep steering the conversation towards me having these romantic/erotic feelings and desires concerning mature gentlemen like him. Romance-talk was clearly the goal as long as I steered clear of actually mentioning sexual acts and I wasn't to arrange an actual meet. Timidly suggesting such may well be possible in the future was as far as it was allowed to go... Being more than a little deceitful was clearly not only allowed, it was an intrinsic part of a lady's armour, according both of the ladies.  It was almost a complete script and I was even provided with a list of words I should try to weave into the conversation. Words like 'delightful', 'adorable','divine', 'enchanting', 'dreamy' and 'darling'. Words and expressions that no heterosexual man or boy would ever use.


Sugar babe

The idea to let our 'princess' have romantic conversations with his/her online admirers had been a great success as my young protégée performed well beyond my expectations. I'm now fairly sure sweet innocent Donna Marie is actually enjoying the game of winding these older gentlemen around her finger, getting them erotically turned on and then, feigning to be bashful and having jitters, gently let them down. My darling crossdressing pupil started to really get the nature of the game so it hadn't only worked as a speech exercise but had also established my darling son as being well on the way to become the conceited little seductress I wanted him to become right from the start. I'm certain Donna Marie is going to shine at the 'Sugarbabe Party' of 'The Diamond Hearts Matchmaking Agency', he/she would be made to attend next weekend. Apart from a selection of classy young ladies said event would be attended by a number of wealthy elderly gentlemen who had paid handsomely to get invited to Lara Luv's exclusive party. Naturally, being a friend of sorts, Lara knew about Donna's true gender but I had, as Lady Fenton advised me, told her how I was just lovingly supporting my troubled transgendered son. I'm not sure if she really believed me (Lara was at least as mischievous as I am) but it at least gave my story the outward impression of respectability. Being discerning as ever, Lara had personally checked how the gentlemen attending the party would react to Donna's little secret and found that only few of these friendly elderly uncles had any reservations towards dating 'ladies with such a minor flaw'. A few of said gentlemen had(especially after they were shown Donna's picture) admitted they would in fact be especially delighted to meet someone who had so consciously and deliberately chosen to become such a deliciously ultra-feminine young lady.


Cinders goes to the ball

To be honest, long before mother's intervention there had always been this strangely authoritative inner voice in the back of my mind that for some reason kept urging me on to take the whole crossdressing game as far as I possibly can. In a lot of ways mother acted very much in unison with 'my inner evil stepmother' who also seemed to find an almost sadistic pleasure in destroying all that is left of the boy in me.
And more and more often there already had been thoughts mixed in about being lusted after by and being forced to make out passionately with especially masculine much older men. I'm not sure where my imaginary stepmother picked up that idea but for some reason the thought excited me to no end.
The whole idea of being seen and lusted after as a pretty girl in itself seemed to completely amplify all the sensations this already disturbing game offered.
The difference between an imaginary wicked stepmother and my actual mother was of course that mother's plans were taking all this out of my relatively safe fantasy world and into my actual day to day existence..... Which was all still rather scary even when it was what I had been dreaming of for years....
And now I was to go to this exclusive party where I was expected to meet suitable elderly gentlemen who'd in turn be there to find a beautiful pretend-niece to court and spoil. Of course I was terribly excited at the prospect but also nervous just like any youngster would be for his/her first grown-ups party. Mother was hovering over me all the rest of the week with extra instructions on my behaviour, voicing how much fun I was going have and what a lucky lady I was. On the day of the party mother's personal beautician had come by to do my make-up and hair and I was fitted with a brand new set of gorgeous salon nails. Tonight's outfit was the same ensemble she had me wear on that memorable first day of my new life though mother did add a pair of glamorous diamond earrings to make it complete and when it was finally time to go I both looked and felt like a total Hollywood glamour puss. My delighted mother assured me that now I was almost certain to befriend a well-to-do older gentleman, I should get used to wearing diamonds.
Mother dropped me off at the party location but she had, conceited and controlling as she was, joined Lara Luv to oversee the happenings from a distance via camera. To me, the whole event had been a total revelation from the moment I had made my entrance to the place.... When I entered the luxurious venue in the style of a high-end nineteenfifties nightclub, it was already filled with party guests holding champagne glasses. The girls all wore pretty party dresses though most slightly more frivolous than my own rather formal and grown-up ensemble. The men were all dressed in suit and tie and somewhere in the age of 45 and over. As soon as an attentive waiter had handed me my own glass of champagne and I proceeded on my way to explore the room, I almost immediately became conscious of the inspecting looks of my fellow party guests. Coming from the ladies it was a mix of envy and silent admiration but the looks that came from a number of the gentlemen coulddefinitely be described as filled with lust. I loved it.... When I sorta found my bearings and saw that nobody here had met any of the others before tonight, getting into casual chats with people was much easier than expected and before long I had found myself actually amidst several obviously very interested older gentlemen of the type that mother had in mind for me. The compliments and expressions of admiration were making me blush and to be frank, in combination with the mere presence of these sweet elderly uncles, they were getting me very very excited. Even though he seemed one of the quiet types, one gentleman in particular had my attention. The gentleman in question introduced himself to me as Sir Edward Bathurst-Smith but I could call him uncle Teddie. He was a heavy-set, not particularly handsome gentleman in his early seventies but what he missed in looks was generously compensated by his charm and sympathetic demeanor. For some reason he made me feel so wanted and beautiful and the reality of feeling both completely comfortable in his presence and being so obviously desired, yes, even worshipped by this experienced older gentleman, had been more than I could resist.
I must disappoint the people who think we were about jump each other there and then because all these feelings were very much just slumbering beneath the surface. Of course I was fluttering my eyelashes and I let loose all my recently learned coquettish moves on him but in the end I was already feeling like an absolute princess when he asked if he could drive me home and I proudly clung to his arm when he escorted me to his Jaguar. My admirer stayed a gentleman all the time just because he was exactly that. Even when we arrived at our house without him even laying a hand on me and I myself asked him if he didn't want to kiss me, he was adament in assuring me that I was under no obligation to do so and that he was satisfied with just enjoying the company of a beautiful young lady like me. By then I was so horny that I wanted him to ravage me and his correctness only made it worse so when he escorted me to the door for our final goodbyes I took a step closer, stood on tippytoes, laid my hands on the shoulders of his conservative bespoke suit and then told him: "Now kiss me, you silly gorgeous man!".

"My dear sweet girl....you have made an old man very very happy tonight...."

Not giving him the time to argue I then kissed him straight on the mouth. Even though I think I actually saw him blush, he then finally got the message and I felt his thick muscular tongue enter my mouth....Timidly at first but soon enough eager and passionate... And when I felt him drawing me closer as his hands gently held my slender silken waist I was in heaven.... Our delicious mouth contact must have lasted minutes but it felt like an eternity and when we finally came up for air my beau once again blushed and almost coyly mumbled: "My dear sweet girl....you have made an old man very very happy tonight....", and then continued with: "It's not that I'm a complete prude but I kinda take the stand that less is often more in these matters. I bet that half the young ladies you have met tonight are probably on their knees now with a strange man's penis in their mouth. Personally I'm disgusted and I bet neither partner is experiencing even half the passion and joy I did tonight. Don't get me wrong, I really like the game of the wealthy uncle having a slightly unhealthy relationship with his spoiled ladylike young niece but not when the uncle factually becomes the client and the niece is just a pretty young prostitute. A bit of moderation and reticence just seems to make things more interesting and the whole 'all out sex' attitude kinda devaluates the more subtle sides of sensuality the game offers. Think of how gentlemen in the nineteenhundreds got excited at spotting a stockinged lady's ankle and how ladies fainted at even the slightest suggestion of naughty ongoings. No, I'm definitely not a prude, I just like to think I get more excitement from the more subtle forms of the erotic and being a bit reserved is an essential part of the game...". With that he kissed me one more time and actually took his leave, promising we would meet again soon. I was still kinda flustered and only managed to whisper a "Call me" in his ear. This wonderful strange man really got in my head and he was probably right as I now wanted to be near him more than ever and when the next day a hundred yellow roses were delivered with the message 'For a true Lady from her loving uncle Teddie', I knew I was in love.

TO BE CONTINUED


  

Don't get me wrong, I really like the game of the wealthy uncle having
a slightly unhealthy relationship with his spoiled ladylike young niece