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.

 

the delights of Stepmotherhood 5 :'ROMANCE'

 

the delights of Stepmotherhood 1

the delights of Stepmotherhood 2

the delights of Stepmotherhood 3

the delights of Stepmotherhood 4

'Romance'

The rest of the way home nothing worth mentioning happened but I was nonetheless relieved to reach the front door where the ladies were already waiting for my return. Obviously they were quite anxious to question me about my little excursion.

It was quite delightful to hear how our young pupil had carried out his task and how he had noticed certain details like how feeling the breeze around his stockinged legs was strangely exciting and how he had almost instinctively reacted to 'the Rangerover ladies' with an almost perfect air of disdain and distance. Priceless actually. It all seemed to have gone perfectly to plan, including Joyce almost bumping into our local bankmanager. Only thing was that when our darling had mentioned Mr. Warren I had noticed a slight tremor in his voice that was accompanied by a thoughtful look on his beautifully made-up face. I didn't go into that immediately but there was clearly something occupying that devious mind of our little lady. Still celebrating the successful expedition there was champagne and while not actually designed as such, the idea of said alcoholic beverage loosening the tongues did enter my mind and I may have been a tad generous with it.... Unexpectedly it wasn't Joyce but Mrs. Arthuro who got loose-lipped when she revealed that she actually knew Mr. Warren quite well as Mrs. Warren nr. 3 who was a fashion model in her younger days had been a close friend of her.  Mr. Warren had not been a very loyal husband and the rumour was that he was well known in the town's stripclubs and brothels under the alias 'Mr. Vincent' because of his remarkable resemblance to sixties movieactor and horrorfilm icon 'Vincent Price'. During Mrs. Arthuro's gossipy revelations about the lecherous gentleman in question I noticed Joyce had once again shown a curious frown on his face and at some point it looked like our little lady was actually blushing.... So when he, after his third glass of bubbles, had nervously and almost guiltily mumbled that he had been strangely attracted to the gentleman, I had been rather pleasantly surprised to see that the result of our darling's hypnotherapy sessions went deeper than I could have wished for.... It was plain to see that with all this extra information, several delicious new scenario's were already forming in my depraved stepmotherly mind. An obviously more commanding gentleman like old Mr. Warren would clearly be a far more challenging and interesting 'boyfriend' for our little lady  than the relatively tame Harvey. Maybe my fantasies were coloured by the Vincent Price comparison but in my head there was an image of Joyce in the role of an ultra femininely dressed damsell being roughly groped by the creepy lovestruck elderly count. I just can't help it, I've always been turned on by the darker sides of romanticism. When I first saw Flash Gordon I actually had an orgasm when the almost disgustingly innocent Dale Arden fell under the hypnotic spell of emperor Ming the merciless and was being forced to become his bride before the plot was ruined by that boring goody Flash dude. A young me even rooted for the lovely Cruella Deville and the wicked witch of the west in Oz(remind me to order some of those flying monkeys one of these days)...
Anyway, after sending a slightly tipsy Joyce to bed, Mrs. Arthuro and I hatched a plan for the next intoxicating stage of the exciting new life I had been forcing upon him. When I later listened at his bedroom-door in passing, I noticed hearing the familiar humming sound of my darling's sextoy accompanied by soft moans, proving that the fascination with his own recently found feminine sexuality was still very much alive. And when everything goes the way Mrs Arthuro and I had envisaged, his relatively pristine boypussy may need to get used to getting stretched sooner than expected, as it were...  
We still had a lot to do though. First Mrs. Arthuro would use the tactic of 'walking her pooch' herself to accidentally meet up and re-aquaint herself with her old friend Mr. Warren, then casually bring up the subject of Joyce as he would undoubtedly have recognized little Coco with his rhinestone collar. Depending on her supposedly lecherous friend's reaction and attitudes she would try to get him to cooperate with our delightfull plans. So when Mrs. Arthuro returned from her mission with an victorious smile on her face and reported her findings it looked like the next step was inventing some vaguely believable reason to get young Joyce to meet up with the gentleman in question. A reason for getting Joyce dressed and made-up a little more extravagant than he was already used to was solved by deciding that us 'ladies' would 'dress for dinner' tonight. Needless to say that no costs or efforts were spared to make our little lady look like every sophisticated older gentleman's ultimate dreamgirl...
During said dinner my ladyfriend dished up a phoney story about her completely accidental meeting with her old friend without disclosing any details about what was said so when she afterwards asked our little lady to deliver a message from her to Mr. Warren, our princess would be none-the-wiser about things to come.

It must have been around nine that night when I got on my way, carrying a big

envelope supposedly containing the lady's message to Mr. Warren. I was as expected meticulously dressed in my most elegant coat wearing my glamorous silk Dolce&Gabbana headscarf, my highest Louboutin pumps and my Gucci clutch.
After a fairly uneventful walk I had arrived at the elderly gentleman's large Victorian townhouse and proceeded to nervously walk up the garden path to the front door. Nervously I ascended the steps, but as I was getting used to stepmothers often scary tasks I just obeyed her instructions and rang the bell. After a short while I heard movements and the door opened revealing a very aristocratic and magnificent looking Mr. Warren, wearing a very elegant vintage smoking with the appropriate real bow tie. For a moment I was dumbstruck by the effect of his magnetic presence just like that time on the street but this time, with him all dressed up, it was much much stronger. I was almost ready to worship this demi-god of a man. " Now tell me what I can do to help you', young lady...", he said in a  very amenable voice. Slightly reassured by the gentleman's amicable tone I told him I was just delivering a message from Mrs. Arthuro.

  
Obviously I wasn't in any doubt that delivering the message had in the end only been an excuse the manipulative ladies made up to get me there and I later found out the message had only read: "Here she/he is. She is totally hot for you. Be nice to her but don't damage the goods on your first romantic date. We insist that our pretty debutante must stay a virgin just a little bit longer".
After he had casually looked at the message, he slipped it back into the envelope which he slid into his pocket before turning his attention back to me, thanking me for delivering it without reveiling it's content. He then took a step towards me and held my shoulders at arms' length while he continued to look me over. "Now let me have another good look at you, sweetheart."
"If Mrs. Arthuro and your dear stepmother hadn't told me I would never have guessed or believed you were ever a boy. And she didn't exaggerate when she described you either. You really do look like a young, extremely glamorous fifties moviestar and I don't think there is a heterosexually motivated male in town that wouldn't dream of  doing very naughty things with a gorgeous little lady like you. princess, " he said, his eyes still devouring me, "Are you sure you don't you have  some young stud boyfriend to go to on a saturday night like this? Not really, Sir." I said. "Stepmother thinks I should only date older gentlemen." A mischievous smile appeared on his handsome manly face....
"So you really came here to seduce me tonight, didn't you, sweetheart? The quite formidable Mrs. Arthuro already informed me about your preferences and romantic orientation. Now tell me that this is what you really want, darling!" he said in a voice that was at the same time suggestive and commanding. "Tell me that you desperately want to become my little girlfriend!
"Yes Sir, I do!" I almost whimpered. "Your stepmother told me that you have been having naughty fantasies about meeting a forcefull masculine gentleman like myself for quite some time now. Is that true honey?" Almost devoutly looking up at the gorgeous man towering above me, I once again nervously mumbled a timid "Yes Sir." Even as I had been totally useless at resisting sweet Harvey's kisses, my romantic feelings had never been as urgent as they seemed to be now. 
Of course he had read me perfectly because in my mind, even as I was still a bit apprehensive about things to come, I have to admit that I had been compulsively fantasizing about meeting him all the time while I was elegantly sashaying toward his house, as well as last night after bedtime... I should also have been suspicious of the almost salacious way my devisive stepmother had made me dress for tonight's events. Everything was just a little bit 'more' tonight. The heels just a bit higher, my undies a tiny bit frillier, the stockings even silkier than normal. And then there was the near-perfect hairdo, the fabulous eyelashes and finally the delicious pure silk satin designer cocktail gown.  Clearly my darling stepmother had quite intentionally dressed me up as the ultimate young seductress on the prowl. Looking at the expression on the older gentleman's face it was working...."Now, young lady, don't you think it's about time you'd give your beau a kiss? Yes sir," I nervously uttered as I took a step towards him and proceeded to stand on tippytoes to give my elderly 'Don Juan' a sweet little kiss on the mouth. I even closed my eyes doing so... "No, no, no ! Not like that, princess. That's very sweet but that is the way you'd kiss your mother, not your 'boyfriend'. I'll show you a real 'boyfriend-kiss', would you like that, darling?" he said while his large hands took hold of my waist and drew me closer, my smallish hands with the salon-nails now resting on his chest.... I became very aware that I had never before stood so close to a male that was as big as my mysterious 'beau'. Even on my very high heels, I had to stand on tippytoes and look up to face him. He just stood there for a few very long seconds, making me feel very small and delicate. And then it happened! The kiss blew my mind completely and for a moment I feared I was going to faint. It felt as if it all had happened in slow motion. This handsome manly face had looked down on his 'conquest' and the as if in a dream he came in for the kiss, me yielding and offering no resistance to his thick muscular tongue as it brutally forced his way into my very responsive mouth.
I could feel his surprisingly strong and manly 76 year old body press against my smallish girlyfied physique. I felt the trousers of his very stylish oldfashioned smoking brush against my delicate nylons whilst my girl penis, as stepmother preferred to call my diminuative appendage, seemed to no avail, desperate to escape it's straining silken prison.. I really felt I was 'his' girl now. I loved the idea that he could turn me on like this, just by acting like the mature alpha male he appeared to be but it was still a bit scary too. He held me like that, still kissing me deep and passionately with me almost devotedly clinging to him, for what seemed an eternity. When we finally came up for air my Romeo wasted no time and virtually dragged me into the house where he gallantly proceed to take my coat and headscarf only to be confronted by me looking even more glamorous in my exquisite peach satin off-the-shoulder cocktail gown. That was clearly his 'cue' to continue our romantic explorations with even more urgency and ardor. When he again grabbed my waist and kissed me it was with so much lust and force that he physically overpowered me and almost violently pushed me against a doorpost. I totally loved it. The whole idea of awakening this much desire and passion in an experienced older man like him was completely intoxicating. To demonstrate my devotion my arm was around his neck to signal him to continue his urgent tongue-invasion. His hands were

only to be confronted by me looking even more glamorous in my exquisite
peach satin off-the-shoulder cocktail gown. That was clearly his 'cue' to
continue our romantic explorations with even more urgency and ardor.

everywhere too and when his leg forced it self between mine I noticed my suitor had a fairly large protrusion in his trousers. Wanting to enhance his passions more than ever now I decided to be bold and put my hand on it and started to lovingly stroke his rigid member through the fabric of his trousers, driving this darling man almost mad with desire and lust.... " Oh my god darling... What are you doing to me?" he muttered in between kisses and whispered declarations of love and lust. "I want you so bad darling" I whispered in his ear, knowing that the conditions stepmother had probably set my lover still ruled out actual penetration on our first romantic encounter.... Meanwhile my 'boyfriend' was, his arm possessively around my waist, guiding me to a large settee in the adjoining livingroom where I elegantly sat down, crossing my knees and adjusting the skirt of my gorgeous dress over the luscious frothy petticoats while 'my boyfriend' was busy with glasses and champagne to celebrate our 'union'. After he finally joined me on the couch with our drinks it didn't take long before his hand had once again possessively encircled my nipped-in silken waist pulling me closer whilst the other hand had now settled on my smooth nylon-encased knee. A surprisingly intimate new experience, to feel his strong large hand lovingly caress me like that really turned me on. His hand that after some delicious fumbling around with the hem of the skirts moved a bit further up my thigh, emphasizing how this ultra-feminine and delicate way of dressing was making me feel so sumptuously vulnerable and accessible in that area. For some reason it's an extremely erotic feeling, especially when it's accompanied by being in the strong manly arms of the man you've got the hots for. Once again my mouth was invaded by his wonderfull thick muscular tongue so deep and hungrily that I felt giddy when he allowed me to come up for air. And all the time my excited little peeny was slowly oozing pre-cum in its silken prison, almost like I was having a prolonged very slow female orgasm....
While we were making out like mad his hand had reached my stocking tops and was slowly moving towards an even more sensitive region and in turn I was again lovingly manipulating his wonderful still hidden rockhard penis through the fabric of his loose-fitting trousers. Only moments later I had managed to timidly open my boyfriends elegant trousers to release his gorgeous big veiny member. When I touched it  my lover shuddered but immediately rewarded my gesture by lovingly rubbing the part of my gorgeous silky knickers that contained my little boyparts and kissing me again. Underneath the opulent ruffled silk knickers said boy parts were for aesthetic reasons still neatly tucked between my legs with a tiny specially made string. Having it gently manipulated through the fabric of the knickers was heaven. We must have been making out whilst gently exploring eachother's genitalia like that for quite some time but at some point, in between increasingly hungry kisses, this darling increasingly excited man had managed to gently steer his beautiful large throbbing manhood under my skirts and between my smooth nylon encased legs up into my pretty knickers. Then, as he with my loving assistance had started gently rubbing his delicious big mancock against my small girlpenis , completely driving me crazy, he proceeded to ardently and in the end almost aggressively dry-hump me untill he collapsed on top of me, awarding me by filling my pretty knickers with large globs of  his warm manly fluids. My small 'flooded' girl penis was completely falling in love with his large mancock....

 

 

I had the almost perfect illustration ready for the finale of this one but I remembered Blogger's rules on full frontal cum-shots just in time..... 

the delights of Stepmotherhood 3 : a ladies lunch.

(Get part 1 first)

Most of the time stepmother's demeanor appeared to be almost sugary sweet and even when there was always a tone of belittlement in her voice, in general she acted fairly amenable towards me. However, whenever I had the unthinkable audacity to protest or complain, she could also become rather frenzied and menacing. "You're called Joyce now, little lady!" she would exclaim in a hissing, almost hysterical voice. I would of course cringe at her vehement insistence and once more realise that I was completely at my stepmother's mercy. In the end I would timidly mumble a resignating "yes ma'am, of course I am". Almost the same thing happened when she first suggested that a young lady like me should date members of the opposite sex. And learn to like it! Obviously i should have known by then she wouldn't let that one rest....

Of course Josh/Joyce had needed some additional assistance to help convince him to play his role in my wonderful script and that's where my friend, who is a renowned professional hypnotherapist comes in. The point is that unlike most of the fantasist who pretend to hypnotise someone with silly soundfiles, I've actually made a bit of a study of this 'brainwashing' stuff. I know you can't hypnotize people to do things they don't really want to but you can however make them overcome hesitancy and shame over things one secretly likes or just wouldn't mind experiencing, so in the end it's all about reasoning and convincing the subject that these things must be. The point is that most people don't really mind being told what to do or even think as it actually takes away responsibility for their actions. Think of how liberating it can feel not having to make decisions or ever having to worry about consequences. Think how attractive the cop out 'I was just doing what i was told' really is. And having been 'hypnotized' into certain behaviours is a perfectly acceptable alibi for our subconscious mind to welcome such a manner of reasoning.... What makes it all work isn't the trance in itself for that is just the tool to narrow ones consciousness to the point where our inner conversation stops and one is more susceptible. Certain anti-psychotic drugs would do exactly the same. In the end it's making the subject freely choose to put you in command. You have to convince them of the attractiveness of such a choice.

Taking this all in, this is about what one of the last 'sessions' we had with young Joyce before I first introduced him to his 'boyfriend', sounded like....
"....O yes, how exquisitely exciting it'll be to finally see you completely deny your initial reluctance, to see you betray your gender and original sexual orientation and actually revel in your own belittlement and wanton submission to your 'boyfriend'.
And o, how I wish I could see you both squirm and swoon in the arms of your depraved 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 'insist' on becoming, just naturally needs the regular romantic attention of some lascivious older gentleman to feel complete."

Obviously I can only give you an impression as the whole session actually took almost 6 hours of our subject repeating instructions and answering questions. It concluded with this...:

"....And I know that after today you will no longer be able resist this aristocratic looking much older man's hands intimately touching you and holding you close. You will still try to deny it but it's completely obvious now.
His hands may brazenly wander all over your silk encased now so girlish body. He may and you of course hope with all your heart that he will. You know he is going to be a very very close and intimate friend to you now and it feels all so completely right and delightful. The feeling of being desirable and feminine that you get from being so very close to him is completely intoxicating.
Being held and touched so very intimately by such a distinguished much much older man is what you will desperately crave now.
His wrinkly veiny old hands possessively moving all over you and shamelessly fondling your cute little tush and kissing you. It all feels so right. He is so commanding and completely in control whilst you just comply and helplessly yield as he takes charge of his 'little lady'.
Because you know this is really what you have secretly always wanted as your body already agrees and shivers with delight at the mere thought of his ravenous touches and other intimacies.
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 who you are now.
You enjoy feeling romantic.
It's exciting and appropriate for you to feel this way.
You already have become such a very romantic 'girl' now 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 ever more feminine.
 You've already become such a precious, hopelessly romantic 'little lady', always dreaming about being desperately in love with lovely much much older men.
Always dreaming about being as pretty as possible for these much older men and thinking about how good it feels to be in the arms of such a darling elderly gentleman.
How wonderfully girly 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 this slightly authoritative elderly gentleman.
You really really like much older men now. 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 these much older men you will almost instantly become horny and aroused.
Always acutely wanting him to look at you and speak to you. Wanting him to notice you and to notice how horny you are for 'him'. You will actually love these gentlemen for belittling you and making you feel so completely helpless, delicate and fragile. You would do almost anything for a man like that because your  intense feminine feelings of romance and sexuality are all rolled into one unstoppable wave that makes you want to belong to him completely."

Evidently our little lady wouldn't really remember much of what was actually said during these sessions as the drugs had made her conscious mind take a 'backseat' but that doesn't make the proces any less effective. When the time comes his Joyce persona will know....

The week after the exciting but also very disturbing 'date' with Harvey, the older gentleman my stepmother had chosen to act as my boyfriend, she had me accompany her to have lunch in town with her small circle of strange lady friends. Of course i was dressed to the nines in a delightful little skirt suit that had a very narrow pencil skirt and a delicious tailored jacket in powderblue satin over a creme coloured silk camisole. And clearly fully fashioned nylons and black patent pumps with a 5 inch heel.  There was also a matching Gucci handbag and Rhonda had done a fabulous job on my own now peroxide blonde hair that with the help of a few

fully fashioned nylons and black patent
pumps with a 5 inch heel

switches had been done up in a fabulous high ponytail with bangs at the front. Stepmommy was clearly determined to show of her 'wonderful creation' to her friends. Evidently i was a big succes but i was a little surprised the ladies seemed to know all about stepmothers 'delightful' schemes and plans which they seemed to find extremely amusing, especially when mommy triumphantly informed the ladies that i now had a 'boyfriend', which had been cause for giggles and felicitations. Next bombshell was stepmother telling her friends that they would be able to see for themselves as the gentleman in question would actually be joining us later.... No sooner had she divulged this when an aristocratic looking older gentleman in an expensive suit entered the establishment and started moving towards our table.

After I had nervously greeted the gentleman I had for some inexplicable reason been so disturbingly intimate with the week before, the elderly casanova had almost immediately drawn me close and he had intimately kissed me just like I was his 'girlfriend' for real, and still being a bit dazed and overcome by the whole situation I once again just couldn't resist kissing him back.  The ladies, enjoying their mainly fluid lunch whilst keenly watching the happenings and seeing the man's brazen amorous advaces and my reactions to them, whispered an approving, "Ooooolala!".  Now feeling completely overcome in his manly arms, I noticed myself almost instinctively surrendering to 'him' by slithering my slender body up against him, whilst he in return let his hands wander from my waist to gently fondle my silk encased girly bum.  I could already feel his growing erection pressing against me through the flimsy materials of my dress and I just couldn't help feeling proud that I made him want me so much that his manhood was reacting this way. Kissing me again I felt his delicious thick muscular tongue entering my mouth with determination.  The kiss became more and more passionate with me actively cooperating in the intimate mouth contact as the ladies started making comments: "Whoo-ee!"  "Look at them, they are actually making out !"  "Isn't it delightful?"  "Show us how much you are in love with him, princess!"
I did exactly that of course and hadn't my darling stepmother and her friends been such respected clients of the up-market establishment, we would probably have been asked to leave.
By now I was obviously  so deeply immerged into my role that I actually loved every minute of it and moaned softly under my "boyfriend's" kisses and was actually starting to believe I was really deeply in love with this depraved elderly gentleman. The 'ladies' seemed to have the time of their lives....

An ultra-feminine young lady, like you 'insist' on becoming,
just naturally needs the regular romantic attention of some
lascivious older gentleman to feel complete.

the delights of Stepmotherhood 2

(Get part 1 first)
I already mentioned that on Joyce's second practice date I would make him sit on his boyfriend's lap. This turned out to be such a succes that when the date was over the boy in question ended up trying to hide a clearly visible wet spot in his trousers.... At least my pretty stepson's Joyce persona seemed to respond surprisingly well to the concept of being desired and being desirable to boys and most likely men in general....

Meanwhile Joyce's girlygirl lessons went on just as before because I wasn't about to let discipline slip after a few little successes. For this week's compulsory reading I had selected a quite saucy piece of text I had found on the web. It was about a glamorous 'girlyboy' describing in detail how he was pleasuring himself with a dildo whilst fantasizing about being with his masculine boyfriend. Vocalising that piece of adult writing (and I made it a point he did it in his sweetest girly voice) made him stammer whilst blushing profusely as he spoke the words but it prepared the way for the little surprise gift I had for our little lady. When he opened the parcel there was a very realistic looking dildo vibrator which caused even more blushing and embarrassment to our shy debutante. When bedtime came and I got up there to make sure he wore his prettiest satin babydoll nighty, I instructed him in my most amenable voice how to insert and use it 'just like the girl in the story' because whether he liked it or not, in the end a genitally handicapped girl like him would have to learn to accommodate 'her man' sooner or later. Anyway, once I tucked my darling in to play with his delightful new toy in private, I left him with the friendly but urgent suggestion that he should imagine being deeply in love with some imaginary man who would take his virginity and make him his bride. "Because that's what all pretty young ladies dream of , becoming a beautiful bride", I giggled.

When bedtime came I got up there to make
sure he wore his prettiest babydoll nighty

Although these last words were just meant to tease for now but they did put some delicious new ideas for the future in the back of my mischievous mind that was already picturing young Joyce completely dressed up as a bride....

Next on my list, as Joyce's practice dates had been so successful, would have to be finding the right gentleman to be my darling's first real boyfriend. Said gentleman would obviously have to act under strict instructions and rules. After all, we don't want our debutante to lose his virginity on the first date. We want our princess to be a beautiful delicate over-romantic ingenue, not some floozy. After a long discussion with my fiendish friend Henry who had been fully briefed on my delightful plans right from the start, he suggested his 'younger' brother Harvey. At the time I didn't really know Harvey was only a year younger than Henry and not quite what I originally had in mind. Discounting his age Harvey was, like his brother, supposedly a bit of an elderly Don Juan who'd jump at the opportunity to be part of such almost fiendish mischief. Finally I came to the conclusion that Harvey was probably the ideal candidate and his slightly advanced age made the whole scenario even more exciting and so deliciously wrong that it was almost perfect.

..my mischievous mind was already
 picturing young Joyce completely
dressed up as a bride....

Obviously Joyce will still be quite scared and apprehensive at meeting and having to flirt with an older gentleman first but that's not really my problem. In fact it still turns me on to see him hopelessly struggle trying to resist my delightful plans while the look of fearful resignation in his eyes shows me that in the end his Joyce persona and 'her' now so wanton receptive disposition will make him timidly give in to and ultimately even welcome Harvey's eager intimate avances. Yes, soon my little lady will be making out very very enthusiastically with this, to most girls his age, rather repulsive elderly man. Harvey really wasn't a good looking man, he was in his late sixties with grey hair and he was seriously overweight but if everything goes to my plan it will at least appear as if an almost nauseatingly devoted Joyce has fallen deeply in love with a gentleman who looks like he could be his grandfather.
O, how I'm looking forward to see my darling helpless Joyce both squirm and swoon in the arms of her eager elderly admirer.... Oh yes, how exquisitely exciting it will be to see my confused feminised stepson completely deny his initial reluctance, to see sweet Joyce betray his gender and original sexual orientation and to see him revel in his own belittlement and wanton submission to his/her adored 'boyfriend'. I find it so much more rewarding to force ones pupil's feeble little mind to actively participate in my schemes than to just force him.
So that weekend, after I had gotten my darling all dressed up for 'Datenight' in a very glamorous see-through blouse in black organza and a silk taffeta skirt with petticoats, I informed him that this time it would be a slightly more grown-up affair. She'd be having drinks with me, Henry and her date for the evening. Of course he'd be expected to be on his best ladylike behaviour and to relentlessly flirt with his date and later in the evening he'd probably have to prove how good he'd gotten at his slowdancing.... And as a final surprise at the end of the evening I would allow his date to take him for a romantic drive in his car to our local 'lovers lane' to engage in the acts one gets engaged in at such a spot.
As expected Joyce looked completely startled when he saw who was to be his date for the evening as even when I had mentioned 'someone older', he had obviously not counted on his date turning out to be a gentleman in his sixties. For a moment I feared he'd start crying but by now he knew that rebelling was probably futile so in the end he once again surrendered and decided to cooperate with my little scenario. So much so that when he was formally introduced to Harvey he coquettishly pretended to be unsteady in his 5 inch heels and needed the gentleman's support. I was obviously delighted to see him developing such deliciously manipulative little traits. So after her date had gallantly offered him his arm and guided him to his seat the evening started with Champagne and smalltalk on the couch where Joyce was again absolutely perfect, sexily crossing her shiny stockinged legs, timidly fluttering his false eyelashes at him and discreetly slithering towards him on the sofa to sit as close to him as possibly with as a result that his date had taken this as his cue to slip his hand possessively around his slender waist. Harvey didn't seem to waste much time and Joyce seemed to meekly go along. It was absolutely delightful to watch so when Henry put on the Barry White cd and we got up for a smoochie dance, our two lovebirds already had a slightly glassy look in their eyes. Even before the song was halfway Harvey was kissing my little lady's neck and whispering sweet nothings in his ear and when Barry and his orchestra had finished he had managed to lock lips with my beautiful stepson and was hungrily invading his sweet inviting mouth with his thick muscular tongue. A few more arousing Barry songs later when the four of us were back on the couch I announced that it was time for Harvey to take his beautiful girlfriend for a drive....
After his 'date' had driven him home later that night I stealthily watched as our lovebirds continued kissing for several minutes on the porch, with Joyce seeming to more than just enjoy the attention that the older man was giving him. I clearly noticed how he actively encouraged the older man's hands to roam all over his body, while he in turn was writhing his slender silk encased body against the man's large frame and enthusiastically returned his elderly suitor's passionate kisses. How delicious it was to watch him actually shiver with delight as the conceited older gentleman's hands went under his exquisite taffeta skirt to caress his smooth stockinged thighs getting dangerously close to his pretty satin and lace panties. Of course the contents of those panties will be neatly tucked away between our little lady's legs so as not to disturb the so carefully created illusion and pretence.
Harvey later told me that at certain point after they had been making out in the car for a while Joyce had let his small beautifully manicured hand with the shiny salon nails 'accidentally' fall into 'her' date's crotch after which he had actually gingerly fondled the obvious protrusion in the gentleman's trousers....


Mrs. Titania Rawlinson-Smythe

After his 'date' had driven him home later that night,
I stealthily watched as our lovebirds continued kissing
for several minutes on the porch, with Joyce seeming
to more than just enjoy the attention that the older
man was giving him.

the delights of Stepmotherhood

Due to a deep-seated and enduring character flaw I had for a long time secretly been fantasizing about feminizing and dominating weak, susceptible boys. So, when after the passing of my late husband, I had noticed that my up to that point almost tediously boring 15 year old stepson Josh had developed an unnatural interest in my lingerie drawer and assorted frillies, I saw my chance to have some fun and indulge in my dark hidden fantasies. Initially I didn't really encourage his dressing up but I had set the trap by deviously providing my 'victim' with ample opportunity to engage in his newfound little hobby and acces to a wide variety of women's clothes complete with plenty of exciting lingerie, make-up and a even a wig! All supposedly accidentally(lol). Like i stored some boxes of carefully selected ladies fineries in his closet that were supposedly meant for the local thrift store. Later, after I had confronted him with his urges and his guilty secret was out, I had made clear that I insisted he would stay in pretty dresses and frillies permanently from that moment onward. As expected he protested but it wasn't very convincing as I had caught him fully dressed striking sexy poses in front of a full length mirror so I told him in my sweetest voice that it was obviously what he himself had wanted. I was only making 'his dreams' come true. End of the discussion.... There were a few tears in his eyes but that made no difference to me. If anything, it was kinda sweet and only made him look even more feminine.  I was really looking forward to controlling him and as time passed I noticed I seemed to become more and more excited by seeing his submission and compliant resignation to the new life I was seducing/forcing him into. And as he was now becoming more and more obedient  nobody would ever have to know of my intoxicating immoral scenario. Aside from my hairstylist friend Rhonda and my friend Henry, who would visit occasionally, no one knew what I was up to. And by the time I would be ready with our little ingenue, nobody would for a moment question her gender and our little lady would herself declare to anyone who wanted to know that it had been all her own wish and that being a pretty young lady had always been her ultimate dream. It's all so intoxicatingly delightful and right......and deliciously immoral.
Of course getting him to dress as the glamorous ultra feminine young miss I was making him into was only part of my plans. His behaviour, mannerisms and preferences would naturally have to match the looks perfectly which means vigorous training and conditioning. My 'princess to be' spent hours mincing around the house in the highest of heels and was made to learn how to sit down elegantly and suggestively cross her legs, how to carry a handbag and how to wiggle her/his sexy girlish tush. Sometimes, when young 'Joyce' wasn't performing her/his tasks to my satisfaction she/he had to be spanked but that didn't happen often as our little lady was in general, surprisingly cooperative by then. Undoubtedly this was at least partly due to the nature of the clothes our darling was allowed to wear. Think of it.... How hard it would be to convincingly rebel or make a scene when one is delicately dressed in an impossibly narrow pencil skirt, a tight girdle and mincing around in 13 cm stiletto's? There is no running away when you can only take very small steps. And having ones delicate physique permanently sensually stimulated by the silks and satins of the clothes and the delicate nylons to the point of near orgasm, doesn't get a young crossdresser in a rebellious mood either. Of course along with the punishments there had to be rewards. Whenever I noticed him voluntary adopting a new feminine trait or affectation like coquettishly adjusting a strand of hair or timidly fluttering his eyelashes,  I just had to reward him with a present in the form of some type of ultra feminine finery. Young 'Joyce' just couldn't resist and never had a chance against the delights that were on offer. The boy has basically been too stunned by my ruthless regime from the moment i took charge to put up any kind of a fight. You should have seen the look on his face when I showed him his newly decorated ultra feminine bedroom... It was priceless. All his boy stuff had been thrown out and the room was now all done up in pastelshades and elegant draperies, it had a vanity and a very feminine bed with satin covers. Now he'd be emerged in femininity almost completely and there was nothing left to remind him of 'Josh'. And as his father has left me quite wealthy, no costs were spared when it came to my little lady's delightful future. Around the same time I introduced a few more rules on his dressing regime. All his clothing and underwear was to be exclusively made from slinky sensuous materials like satin, taffetta and shiny nylon and stockings and stiletto's were now compulsory. Soon his calf muscles will have adapted and in the end our 'Joyce' will probably only be able to walk in shoes that have at least a 5inch heel. The slinky materials now almost permanently caressing his skin in combination with the sensuous nylons and almost debilitating footwear would nearly ensure keeping our debutante in an enduring state of sensual erotic turmoil.

Soon Joyce will probably only be able to walk
in shoes that have at least a 5 inch heel

Obviously Joyce wasn't going to become 'just a girl', I wanted him to be the ultimate 'little lady'. Both a deliciously helpless fragile debutante and a teenage vamp who'd be the ultimate wet dream of every boy and man who'd lay his eyes on 'her'. Almost an archetype of imagined erotic girlhood that wasn't made to exist in the real world....

And then there were the girlygirl lessons in which he was expected to learn to think as a girl by reading specially selected romantic books and publications, imagining himself in the role of the main female character. He had to read certain especially romantic and girlish passages aloud. At first he found it embarrassing but I insisted because vocalizing these things actually seems to really influence ones thinking and also just because i simply enjoyed his discomfort and submission. Making him timidly declare that he was in love with a boy or making him confess he desperately wanted to be kissed by some man whilst fluttering his long eyelashes and blushing profusely was just delightful. And sometimes we

nylon stockings were now compulsory

watched a romantic movie during which he found that I had dressed him exactly like the romantic heroine as to more completely identify with the scenario in question. Naturally i teased him mercilessly about his imaginary romances. Needless to say that after a few of these lessons and with a little stepmotherly help he became a very responsive subject. I even made him write fictional love-letters in which he had to describe in loving detail what he wanted the boy/man I had selected to do to him. Around that time I also decided that it was about time young Joyce was introduced to the outside world and more specifically was to learn about real boys and what effect he/she now had on them....

That meant I would seek out a boy who was usually an overly shy son  of one of the society ladies I knew. The sort of boy who needed a bit of help meeting girls. When the boy found my approval, I would blatantly invite him over and set up a sort of chaperoned date where Joyce would be glammed up completely, make-up and glamorous hairdo, wearing her sexiest eveninggown for her 'boyfriend',who would be extremely shy and unexperienced and was totally intimidated and nervous at meeting a stunning sophisticated young lady like Joyce. These evenings were spent teaching the youngsters how to behave on a date. This went from holding hands, him putting his arm around my protege's waist and holding her to giving eachother furtive little kisses. Later in the evening they would  slowdance with my very specific instructions how to hold and caress eachother, look into eachother's eyes and behave as a teenagers in love. If this all went well they'd be back on the sofa for the final act of the evening, the kissing and making out scene. If I was convinced they were doing it with the right amount of enthusiasm I would leave them alone for a while so they could practice being in love just a little bit more. By this time my conditioning and girlygirl lessons had him reacting to the situation almost completely like any delicate sexually awakening teenage lady would. By now he was immerged so deeply into his new role that it looked like he seemed to actually love every minute of making out with the boy and at least outwardly gave the impression of a young lady who was deeply in love with her beau.

This somewhat mischievous stepmother has really enjoyed Joyce's first little practice date. It's absolutely delightful to see how his underlying reluctance to participate in my little schemes loses out again and again against the wonderfull new feelings and affectations I'm forcing upon him. Joyce did so well and showed so much enthusiasm at the kissing and making out part that her 'boyfriend' actually looked kinda dazed when his mother finally picked him up. Joyce's old self is still in there somewhere of course but that side of my little lady has absolutely no chance of surfacing as long as I keep rewarding my sweet susceptible Joyce with new sensual and erotic sensations and adventures. The practice dates are perfect excuse to do this, I think I'll make her sit on the boy's lap next time, wiggeling her sexy satincovered bum on the poor adolescent's already straining genitals..........
But the fun shouldn't stop at that of course. I was already looking to put our ingenue in more challenging situations and after reading about the fabulous Lady Fenton and her machinations regarding her own stepson Georgina, I started to think it would eventually be a complete turn-on to watch my precious feminized princess being roughly groped and helplessly undergo the lascivious avances of a masculine much older suitor. The whole idea excites me to the point of actually getting close to orgasm. My precious effeminate will undoubtedly ruin his pretty make-up by crying when I tell him of my delightful plans but that will only make his eventual compliant surrender and resignation more delightful. To first see him defiantly squirm and protest and to then eventually watch him give in to his/her receptive girlish nature and my relentless conditioning up to a point where my little lady actually ends up being in complete rapture over the rather aggressive avances of her ardent manly admirer. I totally love it.
Stepmommy dearest is already getting moist in anticipation of the coming events....

 

Mrs. Titania Rawlinson-Smythe

 

to watch him helplessly undergo the lascivious
avances of a masculine much older suitor

 

the delights of Stepmotherhood 2

the delights of Stepmotherhood 3

the delights of Stepmotherhood 4

the delights of Stepmotherhood 5

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........