He never had a chance -Part 3

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the date

When I had told mother, who had arrived home shortly after my gentleman suitor had left, about the night's adventure it turned out that she already knew who I had left the party with. She had watched the party via a monitor with miss Lara and both ladies were quite delighted with my choice of 'uncle'. It turned out that 'uncle' Teddie had been one of the gentlemen who had beforehand expressed a special sympathy towards someone of my disposition. According to miss Lara, Sir Edward was also both seriously wealthy and generous. Not the easiest gentleman to match as he was irritatingly picky when it came to both character and style, so me clearly tickling this elderly millionaire's fancy was a bonus for our mischievous matchmaker.
 
My new 'uncle' was apparently completely serious when he had clarified his preference for a restrained attitude towards our romantic endeavour. He actually had written a sort of guide containing the do's and don'ts and the romantic goals and implications of such a situation. Of course being a vain rich person, he had his musings printed and made into a small booklet for his lady-friends and a handfull interested acquaintances.
Guidelines and etiquette for Courting, Flirting and advanced Coquetry. by Edward Bathurst-Smith
It wasn't very complicated as they were almost the same rules our great-grandparents generation lived by, only with the difference that they weren't forced on the participants from an outside force or by a puritan society. Forced nor ignorant or truly innocent. The goal was completely different too as in 'uncle' Teddies philosophy these rules were there to heighten the erotic tensions and desires instead of subduing or condemning them. Oldfashioned romancing and courting for slightly pervy reasons. A beautiful little costume-drama as it were. When mother got to read it, she immediately fell in love with the idea as it seemed to open the way to all kinds of delightful new experiences. Obviously she was especially charmed with the gentleman's idea's and choices regarding dressing rules and the necessity of perfect deportment and sublimated ladylike mannerisms. Even mother's viewpoint that said ladies should be a bit conceited and over-dramatic seemed well in line with uncle Teddies opinions. I think these things fall under the heading 'advanced coquetry'.

Two days after the party 'he' finally called.... and invited me to visit him at his apartment in town that very night. He'd actually be sending a limo to pick me up. Mother, backed by the gentleman's views on dressing, had of course already been making plans regarding my appearance on my 'date'. She clearly had been prepared for this or she had some sort of contingency plan as when I went up to my room there was a large box with the name of the town's most exclusive evening-wear boutique on my bed and when I opened it there was the most gorgeous taffeta cocktail ensemble you can imagine. It was in gold silk taffeta and it was a bit more formal but definitely just as alluring and titillating as the lovely outfit I had worn to the party. It was a very tight fitting tailored confection of dress, again with a pencil skirt that was so delightfully narrow that it would be almost impossible to move about in if you hadn't been relentlessly trained by a demanding and determined mother like mine. I had already found out that an added benefit of wearing such type of garment is the extremely sensual experience of ones silky smooth nylon-encased legs being deliciously caressed by the silk lining of the calflength skirt at even the slightest movement, resulting in keeping the wearer in an enduring state of sexual arousal. And then there are the intoxicating sounds, the quite noisy rustling of taffeta, the swishy sound of silks on my delicate nylons and of course the clicking of ones stiletto heels on a hard floor. So many breathtaking impressions.... A complete overload for the senses.

when I went downstairs almost
an hour later, mother had a big
victorious smile on her face and
was actually applauding

After what felt like an eternity I finally woke up from my daydreams and I decided it was about time to get myself ready. I bathed, got rid of any possible rests of unseemly facial hair, threw on my pink satin robe, stepped into my fluffy bedroom mules and sat down at my vanity to do my make-up and hair.... I had been doing my own make-up on a daily basis the past weeks and I had seriously paid attention when miss Shana did my make-up for the party so I was fairly certain I could do a good job. I just had to, I wanted my 'uncle' to really want me.... and I was determined to make it very hard for him 'not to'.
I clearly did well as when I went downstairs almost an hour later, mother had a big victorious smile on her face and was actually applauding. "I see you are going to make it hard for your 'pretend-prude' suitor to keep to his little rules....",she said as I indeed looked completely scrumptious. The make-up being a little more dramatic than last time just as the dress was both quite severe in style and still so exquisitely sexual in nature.
I probably still had about an hour until the limo would be there and however confident I felt, it was just about long enough to work up a healthy dose of anxiety over how this little adventure would play out. In short, I felt like any girl/lady felt before a romantic rendez-vous with a potential boyfriend.... Mother had of course offered me a glass of champagne to calm me down but by the time a chauffeur in uniform was at the door to escort me to the Bentley, I was still a bit nervous though the appreciative looks of the servile grey-haired driver were quite a boost for my ego. Another thing I discovered was the fact that I kinda liked the way he called me miss or mademoiselle in that almost subservient over-polite tone and how he basically acted as a servant. I could see myself getting used to haughtily ordering 'staff' around and getting sucked up to. Could mother's kinky dominant disposition be hereditary after all or was it just rubbing off on me? As it isn't a very large town we soon arrived at this chique 1950's apartment-building where my grovelling chauffeur escorted me all the way up to the door of uncle's not so humble abode on the 5th floor, there to be welcomed by the gentleman himself. My new uncle was looking very impressive in his classy vintage smoking and bow-tie so I shouldn't have worried about being slightly over-dressed. After dismissing my chauffeur and greeting me by reverently kissing my hand he guided me into the richly decorated lounge area of the apartment. There were paintings, large mirrors in gilded frames and period furniture, it looked like a virtual palace. While I was taking all of it in uncle Teddie led me to a small bar at the opposite side of the room where he proceeded to open a bottle of very expensive champagne. Soon we both had a glass in our hands and after exchanging compliments on the way we both looked, I timidly asked him about the obvious erotic nature of the paintings. That clearly struck a chord as uncle enthusiastically elaborated on his hobby of collecting erotic art and offered to give me a guided tour. Of course I accepted and clung to his arm as he showed me around the paintings sharing his expert knowledge. At the same time my conceited little mind was of course mainly busy with how I could steer the situation towards me ending up in his manly arms. That meant me going all out giggly girly, fluttering my eyelashes and appreciatively cooing at especially risque depictions and 'accidentally' making physical contact with my elderly Don Juan. Meanwhile my beau had kept my glass filled which was a perfect reason for me pretending to be a bit tipsy and needing to sit down for a moment.... I don't know if it was the erotic images or my flirty moves but my favourite uncle seemed to be quite a bit more responsive than he was on our initial hook-up and when he gently steered me towards the large luxurious couch he supported me by possessively slipping his surprisingly strong arm around my silken waist and he kept holding me close like that when we sat down. I loved it. I was so close to him that I could feel the warmth of his leg, even through the material of my dress. Just his physical proximity and the firm but tender way he was still holding me sent shivers of anticipation down my spine and when I felt his other hand settle on my knee, expertly fondling my nyloned leg through the silky material of my dress, it caused my tightly tucked back winky to desperately fight it's silken prison.
It was almost like the sexual energy, frustrated by my inability to have an erection, had found an outlet in turning the rest of my body into one big erogenous zone.  Every little touch or caress of the elderly man sent delicious electric currents down my spine. And it wasn't just sexual as these erotic sensations were accompanied by strong feelings of genuine affection and gratitude for how sexy and feminine this darling elderly gentleman was making me feel. Instinctively my hand had moved up over his chest to rest on his shoulder so I could draw myself closer and when I timidly looked up at his friendly face, once again fluttering my eyelashes, my suitor had obviously read my mind and proceeded to passionately french kiss me. His remarkably thick muscular tongue invaded my inviting mouth so furiously that he was almost suffocating me but I loved every minute of it as my silk encased body instinctively slithered as enticingly as possible against his manly frame to signal my utter willingness and approval.
I wonder what one of these erotic artists would have made of the scene? The  heavy set and far too old gentleman in his sophisticated smoking and the beautiful too young pretend girl in his exquisitely glamorous dress who was almost wantonly making out with his unbefitting 'uncle'. Said imaginary onlooker would probably also have noticed an impressive protrusion in the senior gentleman's trousers.
Up to that moment I hadn't yet noticed that as my mind had been elsewhere occupied but as my hands seemed to have a mind of their own tonight it didn't take long for my hand to accidentally land itself in my suitors lap, there to be confronted with his obviously excited manhood. To realize that it was I who awoke these feelings in this experienced adult male made me feel even hornier than I already was and I just couldn't resist gently stroking It through the soft fabric of his pants. As fully expected and intended my darling 'uncle' intensified his romantic avances  by drawing me even closer whilst his other hand had taken up expertly fondling my silk encased bum. Again shivers of delight went through me and when we had finally interrupted our delicious mouth-contact my elderly beau muttered something like "My darling, you don't know what you are doing to me". He was wrong there for even when it's just a junior version of his quite substantial manhood, I do still know what it's like to have a penis and I had plenty experience in handling it. I knew very well what I was doing to him. I guess that's one of the points where pretend girls like me have an advantage over natal girls. We have an insight when it comes to judging male reactions to our dalliance and coquetry. I know the effect the girl in the mirror I fell in love with had on me and the effect she'll probably have on other initially heterosexually motivated males. Instead I kept to my role as a naughty and utterly wanton debutante and timidly mumbled an admiring "But sir, it's so big and manly, I couldn't resist, I just have to touch it....". "Miss Lara was right, you are absolutely perfect", he sighed before once again frenching me even more ravenous than before. I almost felt like I was being devoured... And I wanted to be devoured. Yes please.... Obviously I hadn't stopped lovingly stroking uncle's,now rigidly hard, manhood. It wasn't that it was much bigger than the big-girl's toy I had been practicing with but the fact that it was warm, alive and hard for me definitely gave it something extra.... In return my beau was still fondling my bum while his other hand was now manipulating the small pushed up mounts of baby-fat that formed my almost non existent titties through the delicious silk material of the dress . Much to my own surprise my nipples had gone extremely sensitive now and were very much enjoying his sensual ministrations. By then my body was experiencing what felt like a soaring prolonged state of orgasm. And instead of actually being able to ejaculate, I felt my tortured weeny starting to ooze small amounts of fluids into it's silken prison.... If I hadn't been so distracted I would undoubtedly have noticed that my stroking had also made my elderly suitor have a little 'accident'. His tongue was still invading me when I felt a spasm going through him, making me realise what I had done. I just caused a very experienced elderly gentleman to spontaneously ejaculate. Although I myself was still in a very sexually wanton state of mind and would have preferred him to have done that inside my boy-pussy, I felt immensely proud of doing that.... Afterwards this demi-god of a man profusely apologized for his 'accident' before retreating to his private rooms to clean himself up. After our ravenous encounter I realized that my carefully created appearance  obviously must have gotten a bit messed up too so I took advantage of his momentary absence to repair my make up, arrange my hair and readjust the dress. I just had to look perfect for HIS return. And when HE had quietly re-entered the room whilst I was still primping and preening in front of one of the mirrors in the room, I had only noticed him when he appeared behind me taking hold of my waist and nuzzling my neck. Turning round looking at his friendly smiling face there was nothing I could do but lovingly kissing him on the lips, this time more with the intention of showing affection than out of raw passion. Still with a huge smile on his face my beloved uncle guided me back to the couch where he drew me on his lap, assuring me that it was safe now as at his age a repeat of his  earlier accident would be unlikely. It was however still a wonderful feeling sitting there with my arms around his neck exchanging sweet kisses and whispering words of adoration. As my ride home was to arrive soon, my darling assured me we would get more than enough opportunity to get more intimate at the surprise party miss Lara was putting on at the very chique Apollon Hotel the coming weekend. The party was to be centered around those ladies and uncles that had successfully hooked up at the first party and the coupling of me and uncle Teddie would undoubtedly be one of the successtories of the whole thing.... Supposedly mother was very much involved in Lara's plans and according to uncle the devious ladies had clearly something special in mind......something devious.
A little later uncle's subservient chauffeur had arrived to bring me home. When we said our goodbyes uncle once again turned into the lecherous elderly casanova I got so turned on by, almost aggressively pushing me against the doorpost whilst passionately kissing me and letting his hands wander all over me. It was simply delightful seeing the timid and now very uncomfortable servant trying to look away from our little display of obviously completely inappropriate lust and intimacy, which was undoubtedly what my so deliciously depraved uncle had counted on. It could just be my imagination but I think the sad little man actually blushed. I myself just couldn't help myself from adding to his embarrassment by uttering sentences like :"Oh please sir, I just can't wait to feel your hard throbbing manhood inside me." On purpose calling him 'sir' to emphasize the wrongness of the situation at hand. Mother's  taste for conceitedness was clearly once again showing up in her pretend-daughter. Needless to say that  I kept the little man on his toes by playing the role of the haughty overtly sexual junior-diva all through our ride home. I'm convinced that he was not only totally unnerved by the awfully pretty lolita girlfriend of his employer wiggling her bum and coquettishly fluttering her eyelashes but I'm sure he'd be having inappropriate fantasies as well. I sniggered inside, I really started to enjoy the teasing and coquetry side of my new role.
 Once I had arrived home mother had of course insisted on a detailed summary of the evening's happenings and my subsequent feelings and thoughts. Even if I did so without going in too much detail mommy dearest was delighted. Especially telling her about discovering my newfound depravity brought a delighted expression to her face. I think she was actually purring....
When I asked her bout the party she did tell me there had been a slight change of plan as the other couples who connected turned out to be not quite ready to publicly commit quite yet so, with the venue already booked, mother and her fellow conspirator were thinking up an alternative theme that would still feature me and my darling uncle Teddie. I was however still kept in the dark over what the new plans would entail....


So as expected my devious mother had over the past few days kept up teasing me mercilessly with my budding but deliciously inappropriate romance. She had made me express how I, clearly completely impervious to the fact that the man was severely overweight, not particularly handsome and in his seventies, was falling desperately in love with my lecherous elderly boyfriend over and over and over again until it was almost a permanent loop ringing through my already so deliciously confused brain. As if I hadn't fallen in love already of my own accord, mother clearly wanted to take it to an even more urgent and desperate level. It seemed somehow important and attractive to have my emotional state so very ladylike that I should be hovering on the edge of hysteria almost permanently. The type of lady I must become, according to both mother and my mysterious inner voice, was to be completely over-sensitive and delicate to the point of being far too delicate to independently function in the real world. In the end I should be very much like miss Denise in 'Miss High-heels' who, for instance in the chapter with the glass boxes, has a complete fit when first fleas and finally a big fat worm are let loose on her delicate beautifully gloved hands. Contrary to miss Denise I would of course at the same time be deliciously wanton and hypersexual too. I know now this course was 100% necessary and in the end inevitable. And I absolutely wanted this just because it was so delightfully twisted and therefore so completely right. It's just so terribly exciting to destroy everything that was left of what once was Donnie, thereby burning all my bridges....
Yes, I absolutely must become this deliciously helpless and vulnerable lady-thing, an adorable damsell that could find herself in distress at any moment. Especially when masculine much older men are involved....
 
After bedtime I was of course still obediently keeping up the delightful task of relentlessly masturbating with my lifesize adult toy stretching my boypussy whilst softly moaning and vocalizing how much I wanted my elderly 'fiancee' to deflower me....
 

another pretty nail in poor Donnie's coffin

Finally mother's preparatory instructions and teasing culminated into the moment when my actual outfit for the party was delivered and I realized what mother's surprise for me entailed. I should have seen this coming.... I was to be fully dressed as a beautiful bride in a exquisite satin bridal gown, complete with the matching veil, white satin highheeled pumps, the appropriate bridal lingerie/foundations and all the other accessories a glamorous society bride needs.
And then later that day, whilst leading me towards the full length mirror that forced me to me take in the inescapable reality of this, my ultimate surrender, mother continued in her sweetest insincere voice: "It's what every little lady dreams of, isn't it Donna Marie darling? It is what you have secretly been dreaming about too, haven't you, young lady? To wear this beautiful glamorous wedding gown that makes you feel and look so totally and utterly feminine and sexy for your new uncle? A beautiful bride really is the ultimate feminine archetype.
 
Just think about it. Now here is you, a perfect vision of lovelyness dressed in what is like cloud of white satin and silks, nervously standing next to your rich elderly uncle before timidly reciting your solemn vows to be his perfect society girlfriend and him pledging to worship you as the princess you truly are? And all the other uncles and sugarbabes from the first party will be there to witness your big moment. It will be Lara's party of the year. You, the gorgeous but still bashful pretend-bride nervously fluttering  your eyelashes at him adoringly whilst looking absolutely ravishing in your beautiful vintage satin gown. At that point you will probably be bowled over by your own feelings of love, lust and affection for this man but at the same time you will outwardly still 'act'  appropriately shy and demure as your peers see you and your much too old 'uncle' passionately make out to show everybody present your almost desperate love and devotion for what to the other young ladies must be a rather unattractive overweight gentleman who is old enough to be your grandfather. Meanwhile, to your 'uncle', you were of course already the most beautiful young miss in the world before but now your beau is of course throbbing hard for the complete dream-vision of virginal beauty that his adorable young bride so obviously projects. All he wants to do now is to finally take his gorgeous princess-bride up to the bridal suite to appropriately ravage her", she stated with total delight. By then the intoxicating sensual sensations that come with wearing the gown combined with my own image in the mirror and mother's little motivational lecture made me spontaneously ejaculate  in my pretty bridal knickers there and then. I actually went weak at the knees, teetering in my heels and needed mother's support.... In the end the part where the bride(me) was about to be ravaged by her wonderfull 'uncle' was the final straw....  
Recollecting this week's  earlier rendezvous I'm sure I'll be deliriously happy and eager to be ravaged completely senseless by my darling elderly Romeo.

In the end it all happened almost exactly as mother had envisaged except from my elderly groom actually sliding a real wedding ring with an unreasonably large diamond on my finger. It was an impressive do with everybody dressed very elegantly as wedding guests. The ladies even had hired a professional actor to play the part of the priest. Later, when we had taken our leave to consummate our mock wedding, my darling elderly groom had actually carried me over the threshold of the bridal suite. Without going into detail about what followed I will only say that the magical feeling of having almost 8 inch of warm throbbing cock actually inside my body changed everything and when my man finally collapsed on top of me, his beautiful manhood filling my bowels with his warm semen, I actually cried. Happy tears....

 

You, the gorgeous but still bashful pretend-bride nervously
fluttering  your eyelashes at him adoringly whilst looking
absolutely ravishing in your beautiful vintage satin gown.