Tuition with the Bentleys

It wasn't that Andrew had had extremely bad grades or that he was stupid but his pushy widowed mother, being a bit of a snob, was convinced that a son of someone of her standing had to achieve well above average. So when one of her posh friends told her about Mr Bentley who, before retiring, had been the head-master of an eminent prep school and who was now available for private tutoring, she knew immediately what to do, although I doubt if her enthusiasm would have been the same had she known a bit more about the seriously eccentric Bentleys.
So it came about that, every other Friday Andrew's mother would drop him off at the Bentley's large Victorian town house where he would timidly walk up the garden-path and ring the oldfashioned big brass doorbell.
You would then, if you'd been an on-looker, have seen the formidable Mrs Bentley open the door and welcome Andrew, tell him to wipe his feet on the mat, usher him inside the house, and close the big front door after him. The Bentley residence breathed an almost Dickensian atmosphere, as did the inhabitants themselves. The Bentleys supposedly lived there with their niece Ashley whom Andrew had never met as she had to keep to bed as she was sickly and never left her room when Andrew was around.
Inside, Mr Bentley himself would then usher young Andrew into the study whilst his wife heated up a kettle to make some tea.  Andrew would quietly sit down on the large leather settee, once again taking in the atmosphere of the large room with the impressive and almost intimidating amount of books on the shelves.  Of course he didn't see how Mrs Bentley carefully mixed an undefined powder into one of the porcelain cups before bringing in the tea things on a tray.
Today, after Mrs Bentley had poured the tea, Mr Bentley had asked him about how it was returning to school  after the holidays, how he got on with his class mates and teachers and how he had fared with the homework task Mr Bentley had given him at his last visit. The boy politely sipped his tea and nibbled on his cookie whilst Mr. Bentley asked his questions and young Andrew provided his tutor with the appropriate answers which seemed to satisfy the elderly gentleman.
Meanwhile Mr Bentley had sat down next to Andrew on the settee, and Andrew never consciously noticed that Mr Bentley's voice had  gotten a strangely hypnotic, droning quality to it.  Pretty soon, although he was still hearing the words and was able to respond to them, it was with all the animation of a sleepwalker.
Mr Bentley checked his watch as Mrs Bentley was clearing the tea things and he thought about the times Andrew had been their guest in the past and how they had first hypnotized the boy, a job made easier by the introduction of the mind altering drug that they slipped into Andrew's tea. Mr Bentley once again checked his watch...just a few more minutes, and the drug would be at full power. Mr Bentley reflected on how lucky they had been to have found  a subject like Andrew.  He looked at Andrew, sitting on the couch, upright but already in a deep trance.  The boy was small for his 17 years, slim and remarkably graceful in his movements, blonde haired and blue eyed, and atypical for his physical age still without any trace of beard-growth.  All of which added up to Andrew being the almost perfect candidate for their depraved little games.
By the time the tea-things had been put away, the Bentleys decided it was time to proceed to the next stage of the day's activities.  Mrs Bentley now also sat down next to the boy and  started whispering into his ear. Mrs Bentley smiled and then told him to follow her. He stood up and meekly let her guide him up the stairs. And when they came to the door of the mysterious niece's bedroom and Mrs Bentley knocked on the door, informing her 'niece' that it was time to to wake up, he had clearly heard a gentle girlish voice conforming that she was awake, not realising that the words had come from his own mouth.
When Mrs Bentley ushered the mesmerized boy into the utterly feminine bedroom he found that he wasn't surprised to find a beautiful silk robe, a pretty matching set of girls undies consisting of a little bra and knickers, a cute suspender belt and stockings neatly laid out on the bed. On the vanity there was a beautiful wig, makeup and next to it was a very cute pair of highheeled ladies shoes. And when Mrs Bentley made him sit him down in front of the vanity,  after undressing him and helping him donning the undies and stockings he seemed to know instinctively how to apply his makeup and how to finish his transformation by carefully placing the beatiful wig on his head before expertly brushing it into an exciting, very feminine youngish style. Finally he added a pair of small diamond earrings. Meanwhile Mrs Bentley, who had left him alone to let him finish his feminine preparations, had returned carrying the dress she wanted him to wear. It was an utterly girlish peach satin party dress with a pretty little petticoat, short puffy sleeves and a big bow at the back. She then helped the still totally apathetic boy who now looked every inch a very pretty young miss to stand up in his heels and lowered the delicate confection of a dress over his head. She then zipped him up and maneuvered him in front of the full-length mirror.
At first he just stood there like a beautiful manikin, passively taking in his transformation. Mrs Bentley watched him, savoring the next moment.  After a moment or two, she whispered :"Welcome back, my darling Ashley". The effect was completely startling, like a doll coming to life. A spark flashed in his eyes and he took a deep breath, looked at him/herself in the mirror and, when he saw his image, let out a soft moan. Then as he stood coyly before the full length mirror he struck a sultry pose. Andrew had now once again become Ashley. And when 'she' saw Mrs Bentley approach her and gently caress her shoulders 'she' turned around, kissed her 'aunty' and softly mumbled "Thank you aunty, for making me be Ashley again. It was horrible having to be Andrew all this time". "Well darling, you'll be happy to hear that i just had Andrew's mother on the phone and she has agreed to pick him up on Sunday so Mr Bentley can prepare him even better for the coming schoolyear and that of course means our little lady can be with us a little longer this time. Now let's go downstairs and show uncle Arthur how pretty his 'niece' looks in her gorgeous new party dress. It's a good thing he doesn't have a heart-condition as you look so yummie it could kill someone on the spot", she sniggered. 

As expected Mr Bentley was almost dumbstruck when  'aunty' presented his 'niece' to him, looking like a total pageant princess."Do a little curtsey for your uncle Arthur, Ashley darling." she said with a giggle as Ashley elegantly strolled over to her depraved 'uncle' in her glamorous party dress. She obediently complied and when timidly standing in front of  Mr Bentley, she nervously wobbled a little on her skyscraper heels but then did the most elegant feminine curtsey she could master. "Isn't Ashley just divine?" aunty giggled triumphantly. 'Uncle' Arthur looked her over admiringly and smiled as he noticed our princess's pretty face reddening at his scrutiny. "Okay sweetie, now give your uncle a sweet little kiss to thank him and to show him how much of a little lady you are becoming".
And when the feminized boy obediently stepped forward to give his 'uncle' a sweet little kiss on the lips, 'aunty' was grinning like the proverbial Cheshire cat, seeing him acting so deliciously helpless, delicate and ladylike. Of course there was a glass of champagne to celebrate Ashley's return and aunty casually mentioned that after dinner they were expecting a guest in the form of her halfbrother Philip, who Ashley should address as 'uncle' Philip. In her familiar mischievous manner Mrs Bentley also suggested that as her halfbrother was supposedly a rather handsome gentleman, she would be expected to practice her flirting techniques on him. Although her beloved aunty had carefully prepared her for such delightful event to come up, the prospect of it actually happening still scared her a bit too.

Of course Mrs Bentley had had very definite ideas about Ashley's desired behaviours and attitudes towards men right from the start of their delicious little experiment.   
The base of what she was expecting  to accomplish is this: When in company Ashley MUST ALWAYS be acutely conscious and aware of the effect she is having on the men in her presence. Consequently she must also learn to be conscious of what some of her actions, poses and movements will do to them. For most women this is an actual skill but former boys have a little advantage here. As even when they have changed quite a bit, not that long ago they had been adolescent boys who knew very well what the sort of young miss they were now portraying would do to them. They have probably had those reactions themselves seeing their new me in the mirror. Just like deep inside they knew very well what the effect would be when they crossed their perfectly smooth nyloned legs with their incredible stiletto heels in a certain provocative manner. The ones who had been susceptible to the crossdressing bug without the help of a depraved aunt had probably been motivated by very similar emotions already(the concept of being seduced by the girl in the mirror is quite common in (initially)heterosexually motivated transvestites).They just have to learn to revel in the role of the seductress , realizing that the effect the mirror girl has on themself also works on other boys and especially grown men.
The basics for Ashley's succes are thus very much there, we just had to make our precious little lady more and more conscious of them and make him realize how excing and rewarding being desirable and desired can be. She must learn to recognize(and love) the lustfull looks and stares and all other signs(yes, even bulging pants) that men and boys who lust after her will undoubtedly show.
Once we have these concepts firmly anchored in Andrew/Ashley's psyche, together with the fetish and sensual aspects of his conversion he will eventually blossom into a total and complete doll, every man and boy's wet dream. And she will revel in her newfound divalike status too, just because it feels soooo good. Behavioural enhancements like these just always work better if there is some sort of effective reward. So Mrs Bentley had been sure from the beginning that Andrew, through his already impressionable predisposition and the medication they had been giving him to make him more responsive and obedient, would respond very well to a professional hypnotherapist like Mrs Bentley herself to firmly anchor the forementioned concepts in his pliable little mind.

Of course Andrew/Ashley knew that in the end he had to but actually kissing a real man was still a step further than the last remaining bit of Andrew could take but at the same time his Ashley side was overjoyed at the prospect and could barely wait to finally show their guest her utterly feminine devotion.
So  when their guest had arrived and when 'uncle' Philip finally entered the room, looking really handsome in a expensive conservative suit and tie, she wasted no time and minced over to greet him with a kiss just like aunty had instructed her to. Uncle Philip had actually put his strong muscular hands on her waist and it had felt wonderfull. And when he reacted by looking down on her with a little smile on his face and said: " Thank you for that, darling, that was very sweet.", Ashley blushed profusely whilst fluttering her eyelashes . It wasn't so much the whole act itself that had sent her mind into a delicious turmoil as it was the gesture of submission to this masculine older gentleman. In the company of this real man she was once again reminded of how she was obviously destined to be the fragile ultra-feminine princess that Mrs Bentley had insisted he/she must become.
Mrs Bentley was of course totally delighted to see Ashley acting the perfect demure and slightly feeble young lady, fluttering her eyelashes, feigning shyness and being hopelessly attracted to him. She was actually pretending to be unsteady in her 5inch heels so he'd have to support her. Yes, she was really the perfect submissive girlthing for this incurably vain gentleman and she pulled out all the tricks....... Ashley played the role to perfection and you can only do that if you really understand the part. Aunty had almost underestimated the devious mind of the 'natural transvestite'. Our sweet little Ashley actually seemed to be completely conscious of what her actions and little affectations were doing to the gentleman. She was(as they say) playing him like a fiddle. The point being that Mrs Bentley had really created a delicious pretend niece that was already taking after her mischievous aunt like few real girls could. Her little lady was actually enjoying acting all shy, prissy and delicate but deep inside she was very much the one who was directing this little play. It's where dominant males (i mean the ones who think they are - Mrs Bentley doesn't believe in the concept of dominant males) always lose out. The perfect submissive miss does not exist as real submissives are mostly people with a very low self opinion who can never handle a scenario like this without falling apart. The perfect shy demure ingenue is in the end bound to be a sweet delicate manipulative bitch.....

Of course every good thing has to come to an end and so does a perfectly succesful evening and when it was time for uncle Philip to take his leave our devious Mrs Bentley insisted that our little lady should accompany him to the door to see him out. And when the two of them stood in the small hallway to say their goodbyes uncle Phillip took a step towards her and stood very close to her. Ashley instantly became acutely aware that never before had she stood so close to a masculine older gentleman, especially one that was as tall and handsome as uncle Phillip. Even on her high heels, Ashley had to stand on her tippy-toes to look into his eyes. It felt as if they stood there for a very longlasting moment, making her feel very shy and at the same time even more anxious about what was to come. He then slowly leaned over getting even closer to her. Ashley could almost feel the heat of his body. Something stirred in her panties. His masculinity physically excited her. Ashley had never felt like this before. It made her feel so deliciously vulnerable, delicate and feminine. Then Ashley felt his hands go down and settle on her waist. He gently pulled her towards him. Ashley had no choice. To keep her balance, Ashley had to take a half step forward, resting her arms on his chest. Ashley could feel his belly on hers and his manhood pressing against her frail body. He was rigidly hard. Ashley felt his pants material brush against her delicate nylons when he moved in even closer to intimately kiss her. He held her like that whilst passionately french kissing her for quite a long time. Ashley totally loved it but Ashley was also still a little scared by her own rather disconcerting reactions and unexpected emotions. That didn't keep her from enthusiastically kissing him back and sucking on his thick muscular tongue though, Aunty's little talks were obviously doing their work (even though Ashley can hardly even remember what they were about.....).
It felt like a whole new set of instincts was guiding her. Oh how intoxicating it was to realize that Ashley herself was causing all these frantic urges in this handsome older gentleman and even more the realization of all the little erotic affectations Ashley would let loose on him to raise his desire for her even more. So here Ashley was,  already wriggling her slender silk encased body against her beau's manly frame as erotically taunting as Ashley could and immediatly feeling the result when he virtually shoved her against the wall , his masculine body now pressing into her so much Ashley felt totally physically overpowered, whilst the gentleman was once more frantically kissing her. And when he finally came up for air young Ashley could actually hear him panting......I think our little lady is really starting to enjoy aunty's little games........