'Halloween Belle' by Saskia

Madge and Timmy:
'Halloween Belle'
loosely based on the 'Madge and Timmy' stories by A.W.(Anonymous Writer)

It has only been 5 months now since his estranged parents ugly divorce and since Timmy landed into Madge's care on a permanent basis and there was already not much of the boy left in our heroin. Tim's initial almost violent protests against Madge's disturbing plans and ministrations had virtually stopped or had been silenced by now. Madge commanding ways and natural dominance had seen to that.  Of course he was still pretending to fight what was happening to him but he also knew that for as long as he could remember he had actually secretly fantasized and dreamed about a strangely exciting imaginary world where these haughty older ladies for their sheer amusement, dressed him as an ultra feminine young miss in the most exquisitely feminine girls clothes, corsets, nylon stockings and impossibly high-heeled shoes and then, laughing at his ridiculous pretensions to have any say in the matter, kept him in bondage and submission as their delicate obedient sissyfied plaything. So if it had already thrilled him with strange delightful emotions to imagine himself all dressed up in the extravagant dresses, skirts and gowns of a very fashionable young lady, undergoing punishments and humiliations and dainty tortures at the hands of beautiful domineering women who were totally deaf to his pleas and protestations, how much more thrilled and excited could he necessarily be when Madge's appearance in his life made his shamefull secret dreams come as true as they seemed to be now! He had never had a chance...
And now, as some time has passed under our darling Madge's strict supervision, young Tiffany-Tim almost seemed eager to fully embrace dressing as a pretty little lady, doing his hair and make-up without even having to be told, almost as to show off his now total compliance to being the desireable delicate ultra feminine princess that Madge was forcing him to become. It often feels like inside him there now is this authorative inner voice that for some reason makes him accept and finally even desire the strange and scary experiences his formidable guardian was forcing upon him. The voice that seems to find an almost sadistic pleasure in destroying all that is left of Timmy and it seems to fully echo Madge's opinions and demands. It's of course also the delightful silky feel of the clothes, the feminine fabrics, and how they feel when he walks and moves about and how they constantly seem to caress his now so sensitive body when he's wearing a particularly figurehugging slip or dress .  To feel how his garter straps pulled on his stocking tops, and how tight the girdle is and how it molds him into an almost cartoonesque ultra-feminine shape.  And seeing the pretty nylons shine and how slippery and silky they feel on his smooth legs and how he can hear their loud swishy noises with each step as his smooth feminine legs rub against each other. It is for a large part these intoxicating sensations that gave Madge this power over him to begin with and she was exploiting this weakness to the full as everything she now allowed him to wear was exclusively made of delicate ultra-feminine materials like nylon, silk, satin or taffeta.... Needless to say that anything that had even vaguely resembled boys clothes had been banned completely. It was tight pencil skirts, girdles, nylon stockings, pretty silk blouses and exquisite high-heeled shoes all the way now. It wouldn't be long before Tim/Tiffany's calf muscles would have adjusted so far he would hardly be able to walk in anything but the highest of stiletto heels.
Madge had to be creative though to keep the momentum going so on top of his already intense daily training ever so often she would add some extra-curricular activities to keep poor Timmy on his toes and to exploit his depraved little affectation to the full.
Sometimes these take the form of ellaborate dressing-up sessions in deliciously outrageous or very restricting feminine costumes that tickle his fetishist preferences.......
And sometimes she just likes to mess with our little lady's impressionable mind. Like at night she'd have  him all dressed up in his sexiest silky babydoll nighty and his prettiest panties and Madge of course immaculately done up looking irresistably menacing and overpowering. The whole game is even more effective due to Timmy already being bit drowsy from the pill she slipped into his champagne to make his already feeble little mind even more susceptible to her delightful little suggestions. She'd sit next to our pretty princess on his impossibly femine bed in his now impossibly feminine and elegant bedroom when she tauntingly tells him about her delicious but slightly disturbing plans for his future. Meanwhile sweetly caressing him with her perfectly manicured hand under the bedspread until he's totally helpless to resist the sweet erotic agony she is forcing upon him. She keeps this up until our darling is almost in a hysterical state of arousal and is panting for release. At that moment, she knows he is ready to agree to do or say anything she wants him to. She makes him admit to the most embarassing acts and thoughts like him desperately wanting to be kissed and held by manly men and even have him beg her to make him have a boyfriend. Of course she records these statements and confessions for later use when her protégée may have the ridiculous impertinence to rebell against the wonderfull plans she has with him. At their most recent intimate little game our precious little darling actually confessed to desperately desiring to be with a much older masculine man  and wanting to be his pampered little girlfriend or even his trophy wife.  Some of his adorable  girlish little fantasies may be made to come true one of these days but any protests on his behalf will not sound very convincing after his confessions. There is nothing wrong with a little blackmail.......
Of course sweet depraved Madge finds it absolutely intoxicating to see our poor young protégée slowly but inevitably turn into this demure, fragile and almost compulsively dainty wanton princess.  Timmy-Tiffany practically delights in and relishes her own helplessness these days. Like he's now a delicious luxury item, much too delicate and not really made to exist in the real world. Just transforming him into a girl just isn't enough, in the end we want Timmy to be the ultimate archetype of femininity, the perfect damsell in distress and as such both physical and emotionally a virtual invalid.

The next opportunity for one of Madge's ellaborate dressing-up games was Halloween. Madge loved to make a big thing of it and this year she chose a 'Gone with the wind' theme which obviously gave her a perfect reason to get her charge into some really over the top hyper-feminine outfits and to make her 'princess' participate in one or two of her depraved little games. Of course no expenses were spared and she had her friend Conchita, who specialized in very extravagant quinceanera dresses, measure Timmy for the most frilly southern belle dress possible. The final dress was a total dream in pale pink siks and satins and oodles of lace with layer upon layer of delicious petticoats. Of course it came with all the fitting accessories. It even had one of these bonnet type hats with lots of ruches and frills that was kept in place by satin ribbons that were tied into a pretty bow under our little lady's chin. Of course on the day Madge herself and Mildred, her closest friend and part-time maid and housekeeper, would be in period costumes as well. Naturally just dressing up on the day hadn't been enough, Timmy had to be perfect so before the day finally arrived Madge put him through his paces and had him practice relentlessly on elegantly managing the big hoop skirt and the many layers of frothy petticoats. How to move around in them and how to sit down elegantly and even how to curtsey and to behave appropriately submissive and ladylike for the occasion. Madge was as always a stickler for detail. On the day itself even the sweets for the trick or treaters were elegantly wrapped to look right with our little lady's exquisite costume. At first Timmy had been jittery and uneasy about having to be the one to open the door to welcome the neighbourhood children.....,what if one of them or one of the parents escorting the younger ones recognized him......? The contrary was true of course, Timmy/Scarlet was a  big hit. The young girls were ecstatic about the beautifull lady in the pretty dress and the adults kept complimenting the blushing Timmy on 'her' costume as well. Only the few older boys accompanying their younger sibblings were a bit unnerving as they obviously had different feelings towards such an attractive young miss. One of em even let out a genuine wolf-whistle when Timmy/Scarlet appeared at the door. All in all our pretend-girl's ego got quite a boost from the whole experience. The next thing on the program was however far more alarming.
When our dear mischievous Mildred had mentioned that our next door neighbour mr. Blenkinsop who used to be a bit of an amateur actor in his younger days and who had played Rhett Butler in the local theatre production of 'Gone with the wind', always dressed up in his old theatre costume at Halloween, Madge had had one of her 'enchanting' little epiphanies. These seldom seemed 'good news' for poor Timmy and this time wasn't very different.
 After having an obviously agreeable telephone conversation with said mature gentleman it had been decided that on the night in question Mildred would take Madge's 'niece' over to his house to 'get aquainted' as he had clearly been excited over meeting a beautifull southern belle like 'Tiffany'(the name Madge used for Tim when they were in company)..... Off course Timmy hadn't been told beforehand as not to unnecessarily scare him.
 So here is our darling Timmy, of course still very apprenhensive about being taken out to show off his delicious costume to the elderly town casanova next door but was no longer daring to fight his inevitable faith. By now he knew very well that Madge always gets her way. It was unavoidable that he'd completely accepted that at least today he was to be this adorable highly erotisized extremely frilly interpretation of the 'southern belle'. An impossibly feminine and almost compulsively dainty debutante, relishing his/her own helplessness and vulnerability, dressed to the nines in what can only be described as a cloud of bows, frills, and a mass of petticoats in assorted silks and similar sensuous materials. Of course Madge had made shure that underneath this our little lady was wearing the prettiest silk undies and silkiest stockings one could possibly find. The more historically correct bloomers and pantaloons were just a bit too rough and sexless for her pretty protege. Of course his make-up was flawless too. In the end Timmy was now the perfect personification of a young Scarlet O'Hara on feminine steroids.
Of course Mildred had been briefed about how far Madge would allow this adventure to go, as Madge knew very well that Mildred's penchant for depravity easily matched her own and she did not want to see Timmy return as 'damaged goods' this evening just because her friend got impatient or too eager.

Finally Mildred, dressed in a beautifull Victorian maid's costume, rang the doorbell of our neighbour's house and a moment later this older Rhett Butler lookalike appeared at the door, grinning like the proverbial Cheshire cat...... "O my..,Madge really didn't exaggerate when she said her 'niece' made the prettiest 'Scarlet' ever, didn't she?", he said as he actually kissed our heroine's delicate gloved hand. Young Timmy actually blushed profusely at this gesture, that once again confirmed him in his role of  the delicate vulnerable damsell he was being made into. Mildred smiled. It was all going perfect so far. When 'Rhet' asked his lady-visitors in he galantly offered a slightly flustered 'Scarlet' his arm, which was of course again reason for blushes. Up to now it was all very 'Gone with the wind'. As Scarlet/Timmy timidly accepted the tall, slightly arrogant gentleman's arm to enter the house and tried to mince along as elegant as possible whilst barely managing the huge dress and the many delicious layers of peticoats A michievous Mildred had a fiendish grin on her face and was filming everything on her phone. "Madge is going to love this" she thought. As the older gentleman led the ladies into the main room he took his seat in large armchair an then turned to Timmy, saying :"Now let me look at you a bit closer, darling".
"Curtsey for Rhett, Tiffany my sweet." ,Mildred said with a giggle in her voice as Timmie stood there in the gentleman's living room in his exquisite glamorous ballgown. He timidly complied and when he was standing in front of Mildred's old friend mr.Blenkinsop he wobbled a bit on his skyscraper heels but then did the most elegant feminine curtsey he could master!
"Isn't Tiffany just darling?" Mildred giggled as her old friend looked her/him over and stifled an amused chuckle himself as he noticed Tiffany's pretty face reddening even through her makeup. "Okay sweetie, now give Rhett a sweet little kiss to introduce yourself." "I think she should come and sit on my lap first.",mr.Blenkinsop boldly exclaimed.  And with that this brazen Rhett Butler impersonator didn't waste any time and blatantly drew young Timmy closer and placed him firmly on his lap whilst holding our perplexed debutant tightly around her small corsetted waist. Even Mildred was surprised at the audacity of the mature playboys avances. Timmy was of course completely panic-stricken and aghast and when his 'beau' then announced that his make-believe Scarlet now owed him a 'real' kiss, he was just too stunned to react. Rhett however wasn't going to wait for further permission and passionately kissed our young ingenue straight on the mouth. For a brief moment Timmy tried to turn away but the older man was just too persistent in his effort and when his thick muscular tongue forced his way into our little lady's mouth he/she was too stupified to put up any sort of a fight. And when they finally came up for air young Timmy looked as if he was in shock and too petrified to even react. It was like his conscious mind had just retreated so not to have to cope with the overwhelming experience. So when his impertinent admirer took this as submission and kissed his beloved again our delightfull pretend-Scarlet just submitted to her faith and by the third kiss it started to look as if she was actually returning his passionate kisses. And when Mildred, who was still getting everything on video, saw Timmy's delicate gloved hands almost lovingly going around his beau's neck to draw him even closer and to continue forementioned intimate mouthcontact, she was  actually getting moist in her knickers. The video now showed what looked like the two passionately making out. Mildred was almost sorry she had to end this before the point of no return would be reached. Madge wouldn't want things to go too far(yet- as Madge didn't approve of sex before marriage(lol)) but up to now the whole exercise had been absolutely perfect. Madge was never going to give the poor thing a rest with this embarassing proof of his obvious 'voluntary' submission to a man who was old enough to be his grandfather.....