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.