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.