Madge & Timmy : Resistance is Futile

Madge & Timmy : Resistance is Futile
(A Madge and Timmy Tribute based on the writings of AW(Anonymous Writer))

When mrs. Madge Dubois told my mum she could cure me of my nasty habbits and unwanted behaviours, she didn't tell her she actually considered being an unruly adolescent boy an especially nasty habbit in itself... And now, after almost two years under her matronly supervision, she says I'm almost cured....Meanwhile mum and dad had gotten divorced and as mum moved away to live with her new boyfriend and my dad had no time to take care of a teenage son because of him working abroad most of the time(well, that was what I was told at the time but I much later found out that he had actually been commited to a psychiatric hospital after having had a strange shady affair with Madge herself), it had been agreed that I would move in with mrs. Dubois, who was seen as a pillar of the local community, on a permanent basis. By then Madge's plans for my gradual but inescapable transition from boisterous little Timmy to demure young Tiffany had already been well established. To keep up appearances, mrs. Dubois friends and relations were informed about how she had, of course for purely charitable reasons, taken in her former neighbours troubled adolescent son who's earlier rebellious behaviour had turned out to actually have been caused by a tragic deeprooted gender dissatisfaction. So in the end it looked as if she was just helping a confused effeminate teenage boy to discover and accept his true gender. The reality however was that mrs. Dubois was a seriously cruel and depraved lady who just loved force-feminizing the pervy crossdressing boy next door after catching me tryng on her pretty undies and stockings. Few people knew that before becoming the very decent and respectable mrs. Dubois, Madge had actually had a rather succesfull career as a very exclusive upscale dominatrix under the name madame M....
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And when Madge introduced me to her older brother Harold, who was a rather stern-looking retired schoolmaster in his early sixties, I had no idea she had already promissed him she would soon have me dreaming of becoming his devoted ultra-feminine trophy bride.....

As usual Madge was probably right......
I had of course been so scared I was almost shaking with fear and apprehension as this actually was the very first time I would be seen by a man in my new role. Madge actually made me do a little curtsey for this intimidating older gentleman who then showered me with compliments on my appearance, femininity and general elegance. That immediately had effect and I blushed profusely. Over time mr. Harold turned out to be quite gentle and polite in his own belittling manner. He would always adress me as young lady and in conversation usually referred to me as our little lady. For some unknown reason I found this slightly belittling attitude quite exciting as it seemed to confirm and finalize my complete acceptance of my feminine nature. I started to revell in showing of my effeminate little affectations to my stern masculine admirer whom I of course still had to adress as Sir. I loved it.... I really wanted him to belittle me, to treat me like the empty headed submissive girlthing I portraied, his pretty little lady... There was something so very sexy about surrendering myself willingly to the life that had earlier been forced upon me.
Seeing the appreciating slightly dirty smile on mr. Harold's face when I timidly tried out a particularly coquettish move or action would almost make me wet my pretty panties. The first few times I was in his presence, nothing really happened beyond some timid flirting and an incidental furtive touch, it was all very formal and polite despite there being a undeniable suppressed erotic tension in the air.

Meanwhile, much to Madge's approval, the situation had raised my interest in dressing up as seductively as possible to seek his approval. I pretended not to see Madge grinning like the proverbial Cheshire cat when I insisted on wearing my highest stiletto's, the tightest most restrictive foudationwear and my prettiest dresses when Harold was visiting. I also made an extra effort with my hair and make-up to show my total compliance to being the desireable delicate ultra feminine princess that Madge had forced me to become. It often feels like there is this authorative inner voice that for some reason makes me do and desire these experiences. 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 I walk and move about and how they constantly seem to caress my body when I'm wearing a particularly figurehugging slip or dress .  To feel how my garter straps pulled on my stocking tops, and how tight the girdle is and how it molds me into a feminine shape.  And how the nylons shine and how slippery and silky they feel on my smooth legs and how you can hear their swishy noises with each step as my smooth feminine legs rub against each other. It is amongst others these intoxicating sensations that gave Madge this power over me to begin with and she exploited my weakness to the full as everything she allowed me to wear now was exclusively made of slinky feminine materials like nylon, silk, satin or taffeta.... Needless to say that anything that even vaguely resembled boys clothes had been thrown out or even burned ages ago.
So here I was again, dressed up to the nines in an exquisite impossibly narrow and restrictive black taffetta skirt and an equally glamorous creme satin blouse. Underneath I wore a pretty little padded push-up bra that made the small fleshy mounds on my chest look like real boobies and a beautiful high girdle with six suspenders that held up a pair of shiney fully fashioned black nylons with perfectly straight seams. Of course I wore a pair of extremely higheeled stiletto's and every strand of my very feminine light-blonde hairdo was kept perfectly in place with a liberal dose of hairspray. Sparkling glossy lips,  glamorous false eyelashes and a pair of pretty diamond earrings completed the look. Madge was totally delighted. "Darling, you look absolutely perfect, my brother will totally love you like this, so deliciously helpless, delicate and ladylike, just how he likes it. And furthermore, now you seem to like him so much, I think it would, from now on, be appropriate to great him with a sweet little kiss...He'll like that.... Look honey, I know that deep down you are still fighting your true nature but I'm convinced your pretty little panties are straining to keep your little thingie down in its silken prison every time you are in his presence. My brother has that effect on the ladies" I was shure I was blushing profusely as she had of course been right...."Look sweetheart, you just stand close to him on tippytoes and give him a sweet little kiss on the mouth, nothing wildly intimate of course as you know that in general I don't much appreciate public displays of affection. Both me and my brother just prefer to keep to a certain amount of decorum and reticence, even in amorous matters like these. What you two get up to when you are alone however is of course completely up to my brother. Although mr. Harold will always behave like the perfect gentleman, a masculine man like him still has needs and desires, especially when he is in the company of a very sexy young lady like you."
When Madge led me to the lounge where mr. Harold would be awaiting us I was very nervous. Of course I had toyed with the idea but actually kissing a man was still a step further than the last remaining bit of Timmy could take but my Tiffany side was totally overjoyed at the prospect and could barely wait to finally show mr. Harold my utterly feminine devotion.
So when we entered the room and mr. Harold rose from his seat to greet us, looking particularly imposing and handsome in a expensive conservative suit and tie, I wasted no time and elegantly minced over to kiss my mature dream-man on the lips just like Madge had told me to. Mr. Harold had actually put his large muscular hands on my waist when our lips met and it had felt totally wonderful. And when he reacted by looking down on me with a superior little smile on his face and said: " Thank you for that, darling, that was very very sweet.", I blushed profusely whilst fluttering my eyelashes . It wasn't so much the whole act itself that had sent my mind into a delicious turmoil as it was the gesture of submission to this masculine older gentleman. In the company of this real man I was constantly reminded that I was obviously destined to be the fragile ultra-feminine princess that mrs. Dubois had insisted I must become.
Madge was of course ecstatic over her latest victory and decided we should have drinks. "As our little lady has been so deliciously cooperative recently I think miss Tiffany is grown up enough to have a drink with us now.... so Champagne it is."
So whilst the three of us had a glass of bublies and Madge and her brother made polite smalltalk, I was still a bit giddy from earlier happenings and acutely aware of the presence of the man I just kissed. And he kept looking me over too with an expression of what looked like a combination of desire and mild amusement on his face. Of course Madge's conditioning had me reacting as amenable as possible to his  manly attention by timidly blushing and fluttering my eyelashes at him. And as she predicted, unlike all outward appearances, I once again had a very unladylike little bulge in my pretty little panties. I just couldn't help it, even when I should probably be disgusted, this manly older man seemed to push all my girly buttons.
So after finishing her second glass of champagne an obviously very content Madge politely excused herself with the explanation that she had an important call to make and had to leave us alone for a bit. When Madge had left the room, mr. Harold sat down on the couch and padding the place next to him gestured me to join him and of course I eagerly complied and elegantly strolled over to the couch to sit down as close to him as possible. "May I say you are looking extremely glamorous and feminine today, darling. "Upon which I again blushed and timidly mumbled a "Thank you, sir". He then smilingly asked me if that meant I would give him another little kiss, with me of course nervously murmuring a meek "Yes sir"whilst looking up to him longingly. And then it happened...., the first little kiss was still quite innocent but then I felt his big hand slipping around my slender silken waist and he kissed me again, this time more ardently and I hesitantly let his thick muscular tongue slip into my mouth...The kiss seemed to last forever and then came another and another.....And by then my arms were lovingly resting on his shoulders and I was virtually rubbing my slender body against him, his one hand still posessively holding me around my waist whilst the other was gently caressing my smooth nylon-encased knee. I was in a delicious trance....and we must have been making out like this for almost twenty minutes or so when a polite knock on the door anounced the return of Madge. Of course we hastily returned to a pose of almost complete innocence although I must still have looked a bit dishevelled when she entered the room and looked us over with a sly knowing smile on her face. She then informed Harold he was needed elsewhere for an urgent business matter and after allowing me to give him a polite little goodbye-kiss she sent me off to fix my make-up. My make-up wasn't the only thing that had to be fixed though as I had obviously spontaneously orgasmed during the proceedings and had to clean up down  there too. Luckily Madge had me carrying an extra pair of pretty knickers in my purse for just these kind off circumstances.....

Madge was of course completely ecstatic about recent happenings and though nothing much was actually divulged about her future plans for me, the fact that during the following days (my beloved mr. Harold would not be visiting for at least a week) Madge had me studying every upscale bridal catalogue and magazine she had been able to lay her hands on, should have been a clue...........