Lavinia's Revenge

 

 Lavinia,my stepmother was so very very excited!  Tonight, she had her now completely feminized son Marcella(me) going out on his first romantic date as a pretty young lady........with a much older MAN!

 

When I tell people they usually think I'm making it all up as these things sound so completely  unlikely to happen in real life, but over a number of years my unexpectedly cruel and depraved stepmother, Lavinia, had intentionally and very effectively been transforming me from a fairly normal teenage boy into an ultra-feminine pretend girlfriend for much older men. Just over two years ago, my leacherous father had ran off with another woman, leaving Lavinia to care for me on her own. She didn't take it very well and I think she had a bit of a breakdown. Lavinia was actually a very beautiful and glamorous woman who had always played the perfect society trophy wife to him so her outrage was in first instance understandable but she took it a bit far. The point being that in response to his betrayal she in turn decided that she would take her own brand of poetic revenge on her cheating husband by virtually unmanning his only son,.... me.
At least that was part of her initial motivation for doing what she did but her enthousiasm and the obvious pleasure she seemed to get from my subjugation clearly said that it was at least partly for her own depraved sexual satisfaction. Certain forms of cruelty just seemed to turn her on.
And so, after almost two years of mind-altering drugs, strict training and a very thorough brainwashing, it all came down to this.  Poor me!  I'm still terrified about being sent on a blind date with this older man, even when Lavinia had been training and preparing me for such an occasion for months.

 Still, I had been close to tears this afternoon as a totally delighted Lavinia helped me with the especially glamorous hairdo and make-up a young lady absolutely needs for such a romantic outing. Her seductive but authoritive voice telling me over and over again what  a lucky girl I was and how much I would enjoy finally having the opportunity to be in the arms of a masculine man for real... and as always,in the end I believed her too. Lavinia has that effect on people...and to be honest it often feels like inside me there now is this authorative inner voice that for some reason makes me accept and finally even desire the strange and scary experiences my formidable guardian was forcing upon me. That voice seems to find an almost sadistic pleasure in destroying all that is left of Marc and it seems to fully echo Lavinia's opinions and demands.(I was still scared though...)

Lavinia had posted Marcella's(my) profile on a dating website called Mandate.com, including some very sexy glamorous photos of me.  The description said Marcella was 19 years old, had a transgender background and was exclusively interested in dates with much older gentlemen.  Well, within days it seemed like almost a hundred more or less suitable men in the vicinity had eagerly responded.  Lavinia was absolutely delighted when she discovered that she could subject her darling Marcella to quite a few'romantic'encounters with elderly men.

the admirers

My wardrobe had over the past year been filled with a row of very elegant cocktail- and evening-dresses that were both exquisitely sexy and glamorous to wear at such occasions. A strict diet combined with small doses of hormones and strict figure training had by now given me the shape and look of a rather elegant young woman. And with relentless training and lots of practice, Marcella could now convincingly walk, talk and move like a real lady. And she didn't stop at the outward apearances, I was also been made very conscious of the sensual and erotic sides of being an ultra feminine glamour puss. There were the erotic experiences that go with being dressed in nothing but silks and satins, beautifull nylon stockings and restrictive corsets but there was also the realization of the effect the

glamorous young miss I saw in the mirror, would have on......men. And the consequences that may result from that. Lavinia was very thorough and costs didn't seem to play a role(Lavinia's lawyers had taken father pretty much to the cleaners). The prettiest of designer clothes, Manolo Blahnik footwear and the prettiest lingerie one could imagine, I had everything the young spoiled society princess, Lavinia was forcing me to become, could possibly desire. There were also the 'educational' dress-up games where I was totally immersed in extremely feminine fantasy roles and of course the extravagant costumes that befitted such characters. One day it could be Cinderella, the next it was a Southern Belle or even a beautifull Bride. All to get me to think and act like a real romantically inclined girlygurl. Whether you like it or not, in time this stuff will do something to you. Once you realize how feminine you have already become,..you may very well give up the fight and start to revel in your own effeminate status and role. The mind is a strange thing and it may make you realize there are very exciting and enticing erotic delights to be had if you embrace your new life.

 

And sometimes she just likes to mess with her little lady's so very impressionable mind. At night she'd regularly have me all dressed up in my sexiest silky babydoll nighty and my prettiest panties and stepmother herself of course immaculately done up looking irresistably menacing and overpowering.
The whole game is even more effective due to me already being bit drowsy from the mysterious pill she slipped into my champagne to make my already feeble little mind even more susceptible to her delightful little suggestions. She'd sit next to her pretty princess on my impossibly feminine bed in my now impossibly feminine and elegant bedroom when she tells me about her delicious but slightly disturbing plans for my future. Meanwhile sweetly caressing me with her perfectly manicured hand under the bedspread until I'm totally helpless to resist the sweet erotic agony she is forcing upon me. She keeps this up until I am almost in a hysterical state of arousal and am panting for release. At that moment, she knows I am ready to agree to do or say anything she wants me to. She makes me admit to the most embarassing acts and thoughts like me desperately wanting to be kissed and held by manly men and she even has me beg her to make me 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 me. At our most recent intimate little game I actually confessed to desperately desiring to be with a much older masculine man and wanting to become his girlfriend or even his blushing bride Of course any protests on my behalf will not sound very convincing after such confessions. There is nothing wrong with a little blackmail....according to my lovely stepmother....

And she was totally unrelenting. I can still hear her taunting voice ringing in my ears as she continued to lecture me on my desired feelings and behaviours towards future male suitors. "You still need to learn so much about the joys of being helpless, beautifull and desireable for your man and eventually you must accept your new role so completely that you will even find pride in your own willing submission to your lover's ardent manly desires and needs. I know you still don't really want to have these feelings towards masculine mature men but you just can't help it, can you princess? You know your body and heart are now screaming to have your future manly 'boyfriend' throbbing hard for you as he scrutinizes your delicious silk and satin draped fragile self.....

Lavinia

Don't worry about your reservations, princess, when the moment is there you'll now just what to do and you'll remember everything". "Remember everything?. I had no idea what she was talking about..."
Nothing more was explained but stepmother thought we should have a relaxing glass of bubbles until my suitor would arrive. We did, but only seconds later the doorbell rang to announce my date. It turned out to be a bit of a shock because as soon as the silverhaired casanova Lavinia had selected to be my date entered the room I actually 'did' remember everything.... Every word of the latest session I had had with Lavinia's favorite hypnotherapist and friend,the irresistable Lady Fenton. It all flooded back in the moment I set eyes on...'him'....and it changed everything. I remembered it word for word and somehow I instinctively knew it was all completely true and right....

The sessions with Lady Fenton had never felt like in any way like actual hypnosis. There were no swinging pendulums or amulets or strange trance inducing procedures, they were mostly fairly friendly though somewhat onesided talks. The only thing that could have warned me was the herbal tea and the fact I never had much idea what had been said afterwards. I've been told you can't hypnotize people to do things they don't really want to and in the end it's all about reasoning and convincing you these things are right for you.... I'm convinced that's what had happened to me, seeing my instant and complete change of attitude towards my prospective suitor and our coming date. I remembered every word of forementioned talk with the lady and it essentially explained everthing....



Lady Fenton (a few days ago):

"I'm sorry if you are still unwilling to go on your date young lady but your delightful stepmother and I totally agree on how exquisitely exciting it will be to finally see you completely deny your initial reluctance to embrace your wonderful new life, to see you betray your gender and stupid original sexual orientation and actually revel in your own belittlement and wanton submission to your 'boyfriend'. It just has to be.
We just can't wait to see you deliriously swoon in the arms of your ardent masculine admirer....
I know it is just what you've always secretly dreamed of, sweety. Just what you've subconsciously always wanted. An ultra-feminine young lady, like you yourself have insisted on becoming, must almost instinctively yearn for the attentions of her mature gentleman suitor.

 I know in the end you just won't be able to resist this aristocratic looking much older man you will be dating. You are still trying to deny it but it's obvious now. And you know it won't stop there. You don't want it to stop. You already know you want him.
 From the first moment you two first meet you'll be imagining how his hands may brazenly wander all over your silk encased girlish body. He may and you of course hope with all your heart that he will. I'm sure he is going to be a very very close and intimate friend to you in the near future and it feels all so completely right and delightful. The feeling of being desirable and feminine that you get from being close to him will be completely intoxicating.
-Being held and touched so very intimately by such a distinguished much much older man is what you absolutely need now.

Lady Fenton

 His wrinkly veiny old hands possessively moving all over you and shamelessly fondling your cute little tush. Caressing your pretty girlish face, lovingly touching your cheeks and giving you furtive kisses. It all feels so good. He is so commanding and in control whilst you can only comply and yield as he rightly takes charge of his 'little lady'.
Because you know this is what you  have always secretly wanted and dreamed about and it's the best thing that could possibly have happened to someone like you and your body obviously agrees and trembles with delight under his tender loving touches.
And you know that from now on you are going to be thinking and reacting like this all the time.You are never going to want to stop feeling like this because it's part of who you are now.
You crave feeling romantic.

 It's so deliciously exciting and appropriate for a girlyboi like you to feel this way.
You already have become such a very enchanting'little lady'and you are becoming more and more romantic every day and with every time you listen to me.
You enjoy listening to me because I help you to become more and more feminine.
And as you develop more and more romantic thoughts and feelings you will find yourself wanting to listen more and more as it feels so right for you to become as feminine and as dainty as is humanly possible.
 You're becoming such a precious, hopelessly romantic 'miss', always dreaming about falling desperately in love with lovely much much older men.
Always dreaming about being as pretty and as delightfully feminine as possible for these much older men and thinking about how right it feels for you to be in the arms of a seasoned elderly gentleman.
How wonderfully girlish it feels to be held in his strong manly arms.
And as you think of these things you feel all warm and tingly inside.
Feeling so desirable and cherished whenever you are with your elderly 'boyfriend'. Because you adore these slightly authoritive elderly gentlemen.
You really really like much older men. Elderly men are so excitingly masculine to an ultra-feminine boyprincess like you and you compulsively want to make them lust after you and to get them to passionately make out with you.
In fact whenever you meet such an elderly man or fantasise about much much older men you will instantly become horny and aroused.
Always acutely wanting him to look at you and speak to you. Wanting him to notice you so very bad.
To notice you and to notice how horny you are for 'him'.
Because you really are always thinking about it now and always wanting it and thinking about being with these very sexy much older men.
And of course all your thoughts are always in a nice feminine voice.
Always thinking in a pretty feminine voice and speaking in your most feminine tone of voice when you ruthlessly flirt with these elderly men and compulsively fantasize about making out with them.
You feel yourself tingle all over with both anxiety and a delicious feminine devotion whenever you meet such a gentleman.
Even just thinking about such a very very much older man is often enough to make you have little spontaneous orgasms.
You can feel it now. Feel your whole body tingling at the thought of a very much older man touching you.
Feel how exciting and wonderful you feel as a rush of pleasure goes through your whole body at the mere thought of being touched by this very much older man.
First he's just going to hold your hand. You've been wanting him to hold your hand for a while now.
Because it's kind of lonely and sad when there's nobody touching you and holding your hand. Having a gentleman hold your hand makes you feel so very feminine as it's such a loving yet slightly belittling gesture that is usually exclusively reserved for ladies or pretty girls. And you like being touched and having your hand held and that's why you keep hoping he will reach out.
Hoping he will reach out and take your small feminine hand in his.
Willing him to do it.
Needing his manly touch. You just need his recognition of your effeminate status, to feel desired and for the pure romantic undertone of the gesture.
There is nothing else as good as being touched and held even if just your hand.
And now finally as he reaches out lovingly and takes your hand in his, the warmth and gentleness of his wrinkled veiny hand completely overwhelms your now so deliciously out of control feminized mind as it always does when a very much older man even shows a minute romantic interest in you.
It feels so good. it's like an electric shock of pure pleasure all over your body just from his touch. This again and again seems the best thing that's ever happened to you and you are becoming just so aroused and excited.
The feeling of his skin on yours is filling your whole world and it just feels so incredibly good and right and delicious that you want him to hold you forever.
And he notices how you feel and reaches out and takes your other hand too.
Both your hands are enclosed and held so lovingly in his and he is so close now and you just can't believe how good you feel.
He lovingly smiles at you while he is holding your hands and gently fondles them between his fingers and thumb and you realize that this is once again the best thing that has ever happened to you.
Thinking how high praise it is for a romantically inclined love-hungry little lady, like you have become, to have her hands lovingly held by such an attractive elderly man. His big strong hands so gentle and welcoming as they gallantly hold your elegant perfectly manicured hands in his. Completely enclosing your small soft fingers in his feels so good and this then seems the most wonderful thing in the world.
This is the best thing that has ever happened to you.
Just like any other girl you know that the most wonderful and exciting thing in the whole world is the feeling of being taken by a very much older man you love.
And now as his hands continue to hold yours and his touch drives you further and further towards complete, almost orgasmic surrender he bends forward and kisses you deeply and you find yourself blushing uncontrollably as you realize just how badly you want him. And when his hands pull you close to his lovely manly frame, still frenching you, you clearly notice his excited maleness through his trousers.
Feeling how big you've made him and you can't help feeling proud that he likes you so much that his manthing has become huge and throbbing and you want to play with it to please him.
You feel so grateful to him for everything he is doing for you and you want him to feel just as good as you do so you move your hands around to his trousers and undo his belt as he bends down and kisses you even more passionately this time.
You feel so excited its like you have vertigo and you are tingling all over at the thought of handling his beautiful manly penis as you gently unzip his pants to lovingly fondle his excited manhood with your perfectly manicured fingers.


In the end almost every single elderly gentleman you meet can do all this to you.
You will love such a man for controlling you, gently belittling you and stimulating you to be so completely helpless, delicate and dainty. You will do anything to please him because your gratitude and your intense feminine feelings of romance and sexuality are all rolled into one unstoppable wave that makes you desire desperately to surrender to him.
And so at this point you realize that this is exactly how you are going to feel whenever any elderly man speaks to you.
Whenever you now hear a very much older man's voice speak to you it is going to bring you back to this feeling of intense sexual arousal and an almost frightful need to satisfy his manly desires and needs.

 Needless to say that you will choose a commanding much much older man who can teach you to cherish and pleasure him every single day for the rest of your life. You start to realise that you have a deep need to be with this lovely man forever.
And around this time you also begin to  fantasize about wearing an exquisite white wedding dress whilst walking down the aisle with this wonderful man.
Secretly dreaming about it and wanting it. More than any other wanton women you want to marry him and become his perfect little trophy wife.
And as you think about this it feels better and better and his hands feel even more safe and gentle and you love him even more as you feel that you absolutely need to become his devoted little bride.
You only just realized that you've always wanted to get married to such a sweet and gentle elderly gentleman.
And now your desire to be a wife is added to all the pleasure and sexual thrills that you're getting from being touched and held by a very much older man.
And you realize that whenever you see a very much older man, or think about a very much older man, and whenever a very much older man speaks to you, that you will immediately begin feeling this way.
These romantic emotions and this deep sexual excitement that you love so very much will begin to rise in you.
And you will begin to notice that you become aroused and excited very very easily now whenever you are spoken to by an elderly man.
If he looks at you or speaks to you then that will trigger these feelings that are now sitting deep in your mind and becoming a big part of who you are.
Whenever an elderly man looks at you or speaks to you it will immediately bring to mind all these thoughts about marriage and romance.
It would be wonderful to get married and to have him as your husband.
You want to be his wife so very very much and you will be a good and loving little wife to him in every way.
You will be a far better wife to him than any other woman could possibly be.
and so whenever a very much older man speaks to you, you will feel as if you are already wearing a wedding dress.
You are wearing a beautiful satin wedding gown and his hands are so gentle and strong and the feeling of his hands all over you making you feel so wonderful and sexy and safe.
And now as his hands continue to hold yours and his touch drives you further and further towards complete, almost orgasmic surrender he bends forward gracefully and kisses you deeply and you find yourself blushing uncontrollably as you realize just how badly you want him.
And in spite of yourself you find that you can't help thinking about his cock. His cock that is so big and hard and wonderful.
And you are becoming very much aware of his manhood so close to you but hidden inside his trousers.
And as his hands pull you close to his lovely manly frame you clearly notice his excited maleness through his trousers.
Feeling how big you've made him and you can't help feeling proud that he likes you so much that his tool has become huge and throbbing and you want to play with it and please him.
You feel so grateful to him for everything he is doing for you and you want him to feel just as good as you do so you move your hands around to his trousers and undo his belt as he bends down and kisses you even more passionately this time.
You feel so excited its like you have vertigo and you are tingling all over at the thought of handling his beautiful manly penis as you gently unzip his pants to lovingly fondle his obviously excited manhood with your perfectly manicured fingers.



Me (now):

Well, those were the truths that had overflowed my mind the moment I came eye to eye with this gorgeous man who was my date for tonight. He was quite a bit bigger than me, rather stoutly built and was dressed in conservative dark blue pinstripe suit and a goldcoloured silk tie. The gentleman was balding, with silvergrey hair and looked like he was in his early seventies. He was perfect. When Lavinia introduced us he actually almost reverently kissed my hand, mumbling something about how beautiful I looked and I had of course blushed profusely and fluttered my eyelashes at him to show him my gratitude and eagerness. It was like I was struck by lightning and if he had ravaged me there and then I would have been the happiest pretend-miss on the planet. Soon my silverhaired casanova proceeded to guide me to his vintage automobile already posessively holding me around the silken nipped-in waist of the glamorous iceblue taffeta mermaid dress stepmother had made me wear(together with the 5 inch heels and the long salon nails it made me a virtual invalid). It was a very narrow off-the-shoulder contraption that flaired out just below the knee. This type of restrictive attire was of course the perfect excuse to feign the need for my man's support. I loved it and by the time we reached the car I was close to fainting out of pure excitement and anxiety. Acting like the perfect gentleman my date then gallantly took my hand and helped me to enter his classic Bentley. Once inside the car he said he hoped I had no objections to a little intimate dinner at his place. Of course I didn't and even if I did stepmommy's rules strictly forbade such a uncooperative attitude... So after expressing my enthousiasm for such dinner accompanied by some more fluttering of eyelashes, we were on our way...

After a short relatively uneventful(the man only mistook my silkclad knees for his gearthingy a few times) drive, we arrived at a large oldfashioned townhouse in one of the more affluent parts of town. Again my suitor gallantly helped me me out of the car and accompanied me up the steps towards the door where we were met by an older maidservant who led us into the rather chique diningroom where we'd have our intimate dinner. Meanwhile my beau's large hand had, to my delight, again posessively encircled my waist followed by me leaning into him to signal my compliance. I really wanted him to be much more avid and drag me up to his bedroom right now but I guess that a minimum of ladylike behaviour was still asked for. Remembering my lessons on feminine mannerisms I did something very feminine. I stood on tippytoes very close to him and proceeded to quite unnecessary adjust his silk necktie, lovingly looking up at the gentleman's smiling face. I had almost kissed him straight on the mouth there but a supposedly shy little lady like me should of course leave the initiative in these matters to the man. Next this sweet man led me to the dinner table and held out my seat for me. Of course being completely treated as a lady was mesmerizing. I don't recall much of the actual dinner but I gave my everything to be as flirty as possible and to please my date to the max, fluttering my eyelashes and exchanging suggestive niceties. And not for nothing as after we had finished our meal and the maidservant had cleared up and left us to ourselves this darling man suggested that I come over to sit on his quite considerable lap. MMMmmm....Yes please!! Of course I didn't hesitate to mince(the dress only allowed me to take vey short steps)over to his side of the table as elegant as possible to slither onto his lap whilst wiggling my silk and satin covered girly tush. Doing so I immediately found my man's large hand once gain sliping around my waist, this time almost aggressively drawing me close to him whilst his other hand was already deliciously fumbling around my silk covered thighs. By now my hands were resting on his strong manly shoulders and I was expectingly looking up to his friendly but lustfilled face desperately wanting to finally be kissed by this god of a man.... And when it finally happened it was everything I had hoped for and what I had been fantasizing about from the minute I met HIM.... At first the kiss was gentle and tender but then,when I slightly opened my mouth his thick forcefull tongue invaded me with so much urgency that my emotions went completely in overdrive, clinging to him pasionately with my arms around his neck to make him continue his delicious oral assault. I also noticed how his (evidently substantial) manhood was actually growing throbbing hard beneath me. I think in the heat of the moment(between kisses) I had actually whispered that I was already falling hopelessly in love with him.... It was all so beautifull and so deliciously wrong, as lady Fenton would say. This sweet elderly gentleman who was easily old enough to be my grandfather was pushing all my buttons. I loved everything about it. So when we finally came up for air after what seemed like an eternity I suggested we'd take our romantic activities to the large very comfortable looking couch to further celebrate our budding love. After I had slid off his lap I gently took his large hand in mine to guide my lover towards said sofa where I sat down really really close to him with my small manicured hand lovingly resting on the bulge in his trousers. It happened almost accidentally but it obviously pleased him as in no time at all we were back passionately making out with him almost violently pushing me back into the cushions so he was halfway lying on top of me. Feeling the weight of this large masculine man on top of me was turning me on even more and my hand was now actively stroking his erect manhood through the soft fabric of his pants.
At the same time my own weeny that was carefully tucked away between my legs had  slowly been oozing liquids without having an actual erection. But it hadn't been just hornyness, I actually felt genuine affection towards this lovely man who was causing me to feel this feminine and almost dainty. I just had to be very grateful to HIM for everything he was doing for me by letting me be HIS ultra-feminine little lady. And there is the whole distinguished look of this eldery man, the silverwhite hair even his wrinkles and almost weatered face and his almost instinctive air of masculine superiority that had totally captivated me.

Anyway, it seemed Lady Fenton had been right about just everything almost to the letter as at the moment I'm about to open my wonderful boyfriend's pants to take out his throbbing hard member........


p.s. Mr.Theodore (sorry I hadn't mentioned his name before, I must call him either Sir or Darling) asked me to be his date for his ex-wife's wedding next week and I'm definitely going to catch that bouquet....

He never had a chance -Part 3

Read part 1>

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.

He never had a chance -Part 2

Read part 1>
 

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.