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

He never had a chance Part 1

  He never had a chance
( made into the perfect 'little Lady')

 mrs. Zabor

Businesswoman, fashionista and respected member of the local high society, mrs. Zabor had been out of town for a few days, leaving her teenage son alone at the house as he wasn't the sort of kid that would throw wild parties in her absence. This time she had returned a day earlier than expected and when she entered the house and there was a noise coming from her bedroom, she rushed up there to find her beloved son dressed up to the nines in one of her best cocktail dresses. He was wearing make up, a pretty wig and high heels too. She was actually too stunned to react and fled the room before either of them realized what had just happened. In fact the incident wasn't even mentioned again by either of them until weeks later and apart from a few uneasy looks, life seemed to go on as if nothing had happened. And obviously young Donnie himself had no real desire to bring it up and voluntary discuss his embarrassing little secret with his rather formidable mother either. Though mrs. Zabor wasn't much of a prude at all and hadn't really been moraly offended by said discovery, at the time she just had had no idea how to deal with the situation. That is, until mrs. Zabor accidentally met up with the strange Lady Fenton and the subject  came up. And when the mischievous but absolutely delightful Lady Fenton confessed how she had turned a rather similar situation concerning her own stepson into a deliciously amusing opportunity, she had been totally fascinated and wanted to know more. The lady then revealed how she had discovered a strange twisted pleasure in forcing/enticing these susceptible young men into an ultra-feminine lifestyle not of their own choice. In short, Lady Fenton had shown her a completely new way to look at the case and new daring ideas and plans were already starting to form in mrs. Zabor's head. This could actually be fun and come to think of it, with his slender physique and gentle features 'Donnie' would actually make a rather fetching young miss. Maybe not quite a pageant princess yet but he definitely made a quite convincing and even attractive young lady already. And on top of that his over civilized timid nature(read: 'a bit boring') would probably make him rather susceptible to conditioning and motherly authority in general. Especially as he had already shown to have the initial, compulsive penchant for crossdressing present. Thinking of what Lady Fenton had told her about her delightful adventures with her own crossdressing stepson, an involuntary shiver went down her spine at the thought of what she could make her preppie son do and become..... It wasn't that she hated her son or that he had to be punished for his improper behaviour (though I may of course use that as an excuse for crushing eventual future rebellions), it had in fact been more about a bored mother with a deviant mind embracing the slumbering dominant tendencies that had been reawakened by lady Fenton's confessions.. She had always had a mild sadistic streak and certain forms of domination and sexual cruelty had always turned her on but for some reason this specific scenario was actually getting this mischievous mommy especially moist in her pretty knickers.....


 

(Where Mommy is laying down the law):

"My sweet boy, in the light of certain recent events and developments your wise and understanding mother has decided that there are going to be a few changes around here.... Main thing is that I am personally going to see to it that you will stop living a lie. This way you would forever be dressing up in secret without any goal or direction. It will only ever be a rather disgusting dirty secret. No son of mine is going to be a backroom pervert. But as I'm a reasonable person I've informed myself a bit and as you obviously need to do this, your darling mother is going to see to it that you do it right and proper. Let's be honest, I always knew you were never going to be much of a he-man anyway so this may actually be an opportunity to turn this to your advantage. Just accept that mommy has taken control of your perverted little affectation now. The summer holidays have started so nothing stands in the way of realizing the wonderfull plans your lovely mother has made for you. We are going to have so much fun. I'm going to make your obvious and desperate desire for a life in silks, satins and pretty high heels come true in an almost monumental way", she beamed...holding back a giggle.

"Now listen good, sweetheart", she continued in her most amenable insincere voice. "As I've already mentioned, there are going to be more than a few necessary changes in this household so I've already boxed up most of your ugly boy clothes and for now I moved them to the attic. We can still decide to throw them away or, even better, burn them later, once you have truly embraced the reality of your wonderful new life....  And while you were away on your recent little school trip I already had some strong burly builders in to make some delightful changes to the spare-room which will be your room from now on.. You're gonna love it.......",she said, suppressing a giggle. "  As I don't believe in half measures I've had it restyled and furnished so overtly feminine and sugarsweet it would almost be a perfect fit for one of these junior pageant princesses. It even has a walk-in wardrobe..., soon to be filled with lots of pretty dresses, skirts, blouses, shoes, stockings and of course the sexiest silky undies a fashionable young society miss could wish for. What is the point of being seriously wealthy if one can't spend it. Mommy is going to make sure her glamorous pretend-daughter has everything she needs to start her delightful new life....
 
 

As I don't believe in half measures I've had it restyled and furnished so overtly feminine and sugarsweet it would
almost be a perfect fit for one of these junior pageant princesses. It even has a walk-in wardrobe..., soon to
be filled with lots of pretty dresses, skirts, blouses, shoes, stockings and of course the sexiest silky undies
a fashionable young society miss could wish for

I think the men who worked on the room would have been completely outraged had they known the room was in fact intended for my son but I will see to it that you will fit into it in no time at all.... Next time I may need them, these so very masculine alpha males may very well be having spontaneous erections over getting mere glimpses of my glamorous little 'lady'......"

"And don't tell me you don't want them to because I won't believe a word of it.. I've discovered and read your secret little blog very carefully and I noticed you have openly admitted that you have been fantasizing about being lusted after by boys and men, sweetie....(and you'll probably be experiencing plenty of that before your darling mommy is ready with you.... In fact I expect nothing less..., I expect you may even get marriage proposals in the future. From men obviously.)"

"Now go upstairs and get changed immediately to show mommy what a pretty girl you really are. I've already done some essential shopping for my princess and I want my glamorous debutante to dress in the exquisite burgundy taffeta cocktail ensemble I've laid out for you, honey. I promiss you're going to love it.... There is also a matching pair of patent 5 inch Louboutin pumps and I also laid out the appropriate silk undies and nylons for the occasion. We'll be having drinks to celebrate the new You when you come down, darling.... Oh, and whenever you are dressed as a girl (which will be most of the time from now onwards), I will call you Donna Marie.... Clearly a more fitting name for the conceited ultra-feminine little lady I insist you must now become......"


 

(Donnie/Donna):
To be honest I was quite stunned by all this and.... Too stunned even to react or actually realise what mother had just decreed and what it meant. Not that that mattered as she wasn't in the habit of having her decisions questioned. She was just that much of a natural authority person. On top of that my beautiful stylish mother was my absolute idol and very much an inspiration for my dressing-up fascination right from the start..

 there was a more than fleeting
likeness with the Joan Collins
'Alexis' character in 'Dynasty'

(she wasn't the supermodel type of beauty but there was a more than fleeting likeness with Joan Collins's Alexis character in 'Dynasty') All these things were going through my head when I meekly but still quite apprehensively went up the stairs to meet my seemingly inescapable fate.... I could probably still escape and run away but did I really want that? I have to admit that secretly I was also fascinated and curious about the delights this situation could offer as I was of course still the compulsive crossdresser who brought this on himself and mother was probably right about everything else too. She usually is.... And I obviously was totally intrigued to see the cocktail dress my extremely fastidious fashion-expert of a mother had picked for me.... So when I finally reached the room in question and my curiosity had by far overtaken my apprehension I nervously opened the door to find that mother had by no means exaggerated in her description....both of the room as it's contents for there, spread out on the lavishly decorated bed was it, the most exquisite glamorous outfit I ever set eyes on. The type of confection someone like myself could start a religion over and prey to... It was a expertly tailored dress in real silk taffeta with a beautifully embellished bodice and an impossibly narrow calf-length pencil skirt. It came with an extremely glamorous evening jacket in transparent organza with silk taffeta collar and cuffs. Even without looking at the labels you could see by the materials, the craftmanship and the details that the whole combination must have cost a small fortune. An then there were the shoes, the accessories, the delicate vintage nylons and the foundations like a classy 'Kiss me deadly' waistcincher with six suspenders and a matching little padded bra. It was almost dizzying.

(I wonder if there is a word for the almost
'Stendhall syndrome'-like state that so many of
us, compulsive crossdressers, experience
at these sort of moments. I think there should be.)

Obviously the option of not dressing up had totally gone out of the window by then. I was still not very keen on going down to celebrate mother's clear victory but not getting dressed up in these heavenly garments was just not possible for someone with my particular predisposition. As soon as I  had started to dress all earlier reservations were gone as it just felt too good and half an hour or so later I descended the stairs as elegantly as possible looking like a million dollars. Mother actually applauded and smiled like the proverbial Cheshire cat at seeing the new me. She made me pose for her and took lots of pictures. Of course Champagne flowed richly.


Within weeks of mother's "takeover" I had almost completely reconciled myself with my new situation and actually started to enjoy mothers machinations as the now so awfully pretty and glamorous miss in the mirror had strongly re-awakened the very sexual-erotic feelings that had driven me to dress up to begin with. More than ever there were the sensual feelings the clothes themself provided, the feel of silks and satins on my teenage body, the mere restrictiveness, the impossibly high heels, the caress of real nylon stockings. It was still confusing but also extremely exciting. Of course mother encouraged and stimulated all of these old and new feelings to the absolute maximum. And it didn't stop at the clothes, it was seemingly endless deportment training, elocution and  ettiquette lessons, and then there were what she called romance-lessons where I was actually being conditioned to think and behave as a romantically inclined 17 year old miss by being made to read certain very feminine romantic books and magazines whilst deeply immersing myself in the role of the main female character. I was made to keep a girly girl diary, talking mainly about having crushes on certain supposedly hunky men and I was made to write soppy loveletters to said imaginary men, all under mothers supervision to make sure I did it just right. Needless to say that in the end I became a very responsive subject. By then I had been almost completely brainwashed and mother decided that it was about time that I was made to be more and more conscious of being desirable to men. Part of that was posting a series of recent photo's of me posing in my new glamorous clothes on my up to now almost private little online blog. Mother also insisted on polishing my profile a bit and it now suggested I had a preference for well-to-do older gentlemen, illustrated by one of my pictures showing me on the arm of mother's aristocratic-looking lawyer Mr.Harker-Swift(there to deliver the papers regarding my legal name-change) who had been more than happy to volunteer to pose as my 'boyfriend' for the picture. Mother had, in line with Lady Fenton's suggestions decided that the thought of her pretty feminized son being made completely helpless to resist the lascivious romantic attentions of elderly gentlemen was just too exquisitely twisted and deliciously depraved to miss out on. Him ending up actively desiring and welcoming such immoral contacts is so hopelessly romantic.... Basically the goal was to get me used to male attention and to get me to correspond with suitable male admirers whilst staying true to my role as an attractive young lady in search of romance. Mother would supervise and where needed correct me on my reactions and conversations with interested gentlemen, of whom it turned out there were quite a few.... I had to stay in character all the time and if said contacts were deemed suitable enough in mothers eyes, I was expected to exchange pictures with the gentleman and let my messages show a more romantic and intimate tone by adding kisses and similar little girly emoji's. To get me in the right mood mother would have the picture of said man printed and beautifully framed for my nightstand and at bedtime I was subsequently instructed to lovingly kiss his picture and verbally express my desperate attraction to him. Later, when left alone, I was expected to please myself with the very realistic looking dildo-vibrator mother got me whilst imagining being with him. Of course this was quite embarassing at first but to mother's delight I soon got into the ritual and meekly dedicated my nightime orgasms to my pretend lover whilst softly moaning and mumbling how I was falling desperately in love with him. Obviously both mother and I knew very well it was all nonsense but it was supposedly part of training and establishing my romantic automatisms and desired sexual preferences. It obviously worked as over a short period in time I noticed that my reactions and attitudes when in the presence of older gentlemen were increasingly of a romantic/erotic nature. I wanted them to notice me and I was almost inadvertently and shyly flirty around them. Even, and maybe especially our friendly silverhaired mr.Harker-Swift had my full attention these days... I just couln't get the image of me clinging to the arm of my supposed 'boyfriend' out of my head. Even when I know said elderly gentleman had been a close friend of my late father, I think I wouldn't mind him doing things with me, inappropriate behaviour things....

 
Meanwhile mother had been working on the next stage of her exquisite little scenario.....

Although The Diamond Hearts Matchmaking Agency  was known as a normal upmarket matchmaking and marriage service,...it was also popular with certain ladies between 18 and 30 who were looking for a 'sugardaddy' and it was quite popular with the wealthy older gentlemen in question because the discerning owner Lara Luv, who was an acquaintance of mrs. Zabor, set high standards for the girls when it came to style, good manners and foremost their ability to both please their generous 'uncle' and to adapt to the social graces of high society. It wasn't cheap but such arrangements aren't supposed to be. This way the well-to-do gentleman in question had some certainty he was connecting to the sort of young miss who was reliable and was unlikely to embarrass or even blackmail him( it happens). Equally the young ladies must be protected from predators posing as sugardaddies for less than generous reasons.

To be continued

More than ever there were the sensual
feelings the clothes themself provided,
the feel of silks and satins on my teenage
body, the mere restrictiveness, the
impossibly high heels, the caress of
real nylon stockings.