It came as a surprise. When Abigail received a message from his sister telling him to go to her room he was astonished. He never went into the family apartments until recess, so such a demand was abnormal.
Bossy bitch, Abigail thought as he made his way there, but he didn't say it. His relationship with his sister had never been one of close kinship, they'd spent too much of their lives at separate boarding schools for anything like that to develop, and while he had a slightly bullying facility himself, Jennifer always topped him when it came down to dominance.
The years Jennifer had spent at school was a mercy for plenty of boys in the world, although not for himself. Whenever they were both home on vacation they had all felt the brunt of her bullying, demanding manner. Everyone respected her physical strength, but he himself found her voice to be the most intimidating thing about her. He could never seem to resist the power in her voice.
She'd constantly ordered him around and made him do things he knew were wrong, such as dressing up as a girl. She'd taught him to use make up properly - foundation, blusher - mascara to give him nice long eyelashes, eyeliner and eye shadow, and lipstick. And then she'd dressed him in stockings, bikini pants and a garter belt before slotting him into high heeled shoes. She'd praised his looks, made him feel like a beautiful flower.
He didn't mind it at first. Doing naughty things was exciting, and if he was being made to do them he was blameless and it wasn't his fault. Being told to masturbate into his handkerchief in the back row of a cinema or ordered to do it with a hand in his pocket when on a bus journey had been demeaning, but most of all he'd hated the humiliation of being told to go up stairs with one of her girlfriends to show her how a boy did it. He could still recall the excruciating shame of being alone with a girl who was there just to see him do a cummy in front of her.
Finally there came the time Jennifer introduced him to another youth whom she'd also trained to cross-dress. She'd made them get together on a bed and told them to put on a lesbian show. That was the first time he'd ever done another male in the backside, and he'd taken to the habit.
"Why do you want to see me?" he asked when Jennifer let him into her room. He asked the question courteously. He may have been top dog in the school, but he was never superior to her.
His sister prevaricated slightly, but only for a moment, before telling him the callous facts. "Your time at Fairyfield is at an end, Abigail. Mummy needs money urgently so she's going to sell you. She as a guest coming this afternoon who wants a pantywaist as a companion, and she thinks you're the best choice."
Abigail caught his breath. He'd always known his mother didn't intend her school to cater for young men older than he was, and in the future a number of her students would be sold off during the course of each term, but it still came as quite a shock when he discovered she was selling them now. First Fifi who had gone to some mad marchioness, then Poppy who had been sent off on trial loan to some woman in the village, and now himself, her own son, bound for only goodness knew where.
He was horrified and surprised, but didn't wish to show that in front of Jennifer. He chewed his bottom lip, blinking rapidly while his hands hung clenched as impotent fists at his side.
The girl could see hurt and insecurity in his face anyway, but typically she showed no emotion. Her attitude was one of detachment and ruthless efficiency. Her face beamed inappropriately as she closed the door behind him. "Don't worry. It's all right. You've always been a very co-operative girl so I'm sure mummy will have chosen someone nice for you. She will probably have chosen a man."
Still disconcerted Abigail shook his head. "I hope she's chosen a man. I wouldn't know what to do with a woman. I don't even know what to do with girls."
"That's what I thought," Jennifer said, "Living at Fairyfield is all very well, but it makes sissies naive about the world outside," she said. "But you'll probably never have a choice in the matter, darling. Sissies rarely have a choice in anything. They're not required to think or make decisions, they're just required to be obedient when they're TOLD what to do."
She continued, "Because you've been a very good girl lately and you're so pretty I've been giving some thought as to how you should present yourself to a possible new owner. Since your not allowed to wear make-up when in uniform I thought I'd help you with some glamour."
"I can do that for myself." he murmured churlishly.
Jennifer's eyes narrowed and she regarded him as she might a Sunday roast before carving. "I want to do it." she snapped, and his head drooped.
Immediately his sister reviewed things. "Your hair is okay. The pageboy cut will be fine with just a ribbon. A bit more make-up though. Your time as head girl as made you something of an old fashioned blue-stocking, so you'll benefit from rouge and shadow to plump out your cheeks. Some masacra too, to lengthen your eyelashes, and then something to push up your little tits. It won't be a problem."
In the past Jennifer's lovers had always been girls, or emasculated boys serving as substitute girls in a subordinate, feminine way. Turning a young man, helping him find his way into the inexplicable excitement of sissyland and projecting him into girlhood had always been on top of her list of pleasures. She enjoyed kissing them and feeling them up when they were in girls clothes, and putting them into a bra and getting them trained in wearing stockings and high heels were desirable first steps.
"What a stunning beauty you are with that demure-eyes-cast-down look. You could become a fashion model. In the outside world men will fight each other for a chance to coo over you and hold you in their arms, and girls will want to smack you for looking so sweet." She pulled him close, sliding one hand round to feel the shape of his pert bum and then leaning down to peck a little sisterly kiss onto his flushed cheek.
"Oh!" Abigail's long black lashes fluttered down onto his rosy cheeks and he relaxed and squirmed with pleasure. For a second she pressed against him and enveloped him with her perfume, she could have sworn he detected the beat of his heart.
Abruptly she leaned down and kissed the side of his neck, this time her teeth biting and pulling gently at the tender skin.
"Oooohhh! Jennifer, what...?"
Realising that fun times with her subservient brother were coming to an end, Jennifer thought to make the most of the moment and slid her arm down to cup his waist.
"Such a tiny waist," she said in admiration, "Look at that, I can very nearly get my arm all the way around it. You swish around so lightly and so prettily, and you've got superb legs. Personally I think boys who have nice, shapely legs should take every opportunity to show them off."
At that moment the button and zip on his skirt became unfastened and the garment dropped down his legs to become a puddle of blue serge around his nylon-clad legs. Now he quivered with increased uncertainty, but Jennifer didn't even acknowledge what she'd done.
Alarmed, Abigail flinched. "Jennifer, you're undressing me."
"That's right. Lovely things like you shouldn't spend all evening buttoned up to the neck."
"Okay, but honestly, I can manage to take my own clothes off. I don't need a nursemaid."
Jennifer grinned. "Oh, but I think you do. You need a girl to look after you."
The dear, sweet thing was in complete surrender to her so she leaned forward and kissed his mouth - and Jennifer knew about kissing, of that there was no doubt. Her lips were full and hot, and she used her whole head, not just her lips. But it was a bona fide kiss, simple and sweet - tentative, chaste and almost virginal - that seemed so right at that moment. Abigail's body was soft, sweet and fragile and his lips warm, pliant and comfortable. As she drew back she nibbled lightly on his lips. Delicious! Some men would walk barefoot over broken glass to try some of that.
She placed a friendly arm about his shoulders and ushered him towards the bed, sitting him down at her side she cradled him in her arms, feeling the slight musculature of his body through the material of his blouse as she urged him to throw his arms about her neck and press his cheek against her face.
Easing him back she unbuttoned the cuffs on his blouse and then the front of it all the way down. Reaching inside she began tracing her fingers along the bare skin of his sides and across his back until acting on instinct their lips touched again - tenderly at first, then more robustly, fiery, and then the whole of Jennifer's tongue was thrusting into his mouth.
As the heat of passion began to build she smeared her hot lips across his flushed face in order to lick his ear before trailing the tip of her tongue down to run along the line of his jawbone. The moist tickle under his chin made him raise his head, which enabled her to stroke her tongue up and down the blemishless white skin of his throat.
Finally she removed his blouse, and skimming it from his shoulders left him wearing only his underwear; white panties and a little white cotton bra clamped to his boyish chest. His breasts were flushed and his perky nipples could be seen pushing at the material.
Her hands moved over his bare back, stroking him down from his neck to the thrust of his bottom, then she began to kiss the top of his breasts as she reached behind to undo the clasp on his bra. Ah, yes, bare titties! Boy titties. Maybe only little bumps and not full breasts yet, but good enough to thrill.
Her mouth went down on his right nipple which was erect and tender, and her warm, slick mouth feasted on its tip, a treat too delicate to resist - kissing it and sucking it and giving it a little love-bite, just a hint of teeth to make him whimper, before switching to the other side. It wasn't too long before the sweet scented sissy was writhing and moaning exactly like the hot-bodied girls she'd seduced so often in her past.
Indeed, Abigail was experiencing the kind of high-octane sexuality he'd never known with a girl before; he adored the titty love, it suggested smouldering, hidden passion and apparent desire. Enraptured by Jennifer's magnificence he went limp in her arms, allowing the teenage girl to lay him down and roll on top of him and trap his body beneath her own, permitting her questing hands to squeeze and pull his tiny breasts while she feasted on his scrumptious flesh.
"So pretty. Such a sexy girl." she husked as she kissed his cheeks and eyelids. She could tell he liked what she was doing and what she was saying. It made him sigh and puff out his chest, and his big, brown Bambi-eyes squinted into slits of pleasure.
At last she sat him up, and quivering and docile, Abigail sat uncomplaining and immobile as the girl set about transforming him. Opening a compact she daubed powder on his nose and crooned softly. "A little dab of powder, a little dab of paint, makes a little lady what she really ain't."
She dosed him liberally with lipstick and musky smelling perfume, then brushed metallic bronze powder onto his eyelids with a large bushy brush. After the make-up came the accessories. She'd found plenty of stage-jewellery in Margaret Pardoe's costume cupboard. Clip-on earnings, bracelets, necklaces, and she delighted in adorning him like he was a girl going to the Oscars.
Long false nails varnished to a colour that matched the lipstick on his mouth were added to his fingertips, and there he was, with makeup flawless, eyes mysterious, his glossy pink lips parted slightly in apprehension to give a hint at the pleasure they could offer.
Three inch heels would complete the feminine look, she decided. He was slightly smaller than her, but even if the shoes gave him additional height he'd still remain where she wished him to be - below her.
She didn't qualify her behaviour, instead she pushed him down to settle into the corner of her bed, noticing how his meagre weight barely depressed the mattress. Ideally she knew she should have sacrificed a little time to soothe him and put him at ease before starting anything special, but her eagerness refused constraint.
Her fingers stroked his legs, delicately smoothing them up his coltish limbs in what could only be interpreted as a caressing motion before anchoring the dark welts at the top to the clips on the dangly suspender straps. Shapely legs sheathed in nylons. Excellent! thought Jennifer.
"You're different to the others. You always have been. You've a streak of testosterone in you that defies everything. I've noticed how horny you become when you stand near Emma Twist, and I dare say you'd have no conscience about screwing a length up me if I allowed it."
He drew in a sharp, shocked breath, but before he could compose himself properly she straggled his hips and took hold of his hand and thrust it up under her skirt. "Touch me between the legs. Feel my pants. Sample the warm, wet slickness you generate in the gusset."
"Jennifer!" His arousal was now obvious. Embarrassed by his own excitement he raised his knee in a weak attempt to hide the impudent rise of his penis inside the scallop trimmed bikini pants he wore. She noticed right away how they were now distorted by excitement.
Callously she withdrew his hand and thrust it away. "There is yet time for some fun. Before that, your pants must come off." she told him.
Ignoring his exclamations her fingers stroked his belly and began to fiddle with the waistband. Abigail gulped. The emotions inside him - the tumble of dread, nervousness and shame - were not discussed. He was allowing her to dominate. He was letting his sister undress him, letting her see he was wearing panties and allowing her to see that he was aroused in the lewdest way possible.
Her hands moved down behind him and he didn't move as she smoothed them over his slender buttocks and playfully patted his lean rump. "You're very obedient, and that pleases me." she told him as she moved her hand down over his straining bulge. "Does dainty girls underwear excite you? Do you enjoy feeling your boy parts rubbing inside it?"
Abigail almost panicked. Without speaking - without asking - he gasped a little as she put her fingers into the waist elastic and eased the garment down over his thighs. The tone of her voice had been uncompromising and he didn't dare argue, and against his expectations he became beguiled by the persuasive caressing as they slid over his legs.
She hauled the pants down his legs until they became a puddle of wispy nylon around his feet. Oooh, he felt so helpless and at her mercy, and when he made an effort to stop her going further she just slapped his hand away.
Despite his embarrassment, or perhaps because of it, his penis was stiff and distended. It was standing out from the depilated soft curve of his underbelly and the white unblemished flesh of his thighs, swollen and visually straining, raised above a right-angle, a shin bone wrapped in silk that bounced when he moved, with a blushing bell-end straining out from its tip.
"My, my!" murmured Jennifer approvingly, "You could do damage to the furniture with a thing like that. Better watch where you go."
"Jennifer, are you going to wank me off?"
The girl gave him a scathing look. "Wank you? Certainly not. You effeminates are all so selfish, always thinking of your own pleasure. But I know what a mess you make when you get overexcited, and I don't want your girly gook squirting all over me."
Abigail suddenly felt uneasy. When she pulled back she left him with the impression of strength and power that excited a curious quivering awareness throughout his whole body. He noticed how she focused on him, one eyebrow raised in cynical amusement at his blushes. It was easy to read that look now, and he remembered the terrible demands she'd made of him in the past.
Aghast, he gazed up at her. He couldn't blush any harder, the heat of embarrassment glowed in his face. He was quaking all over, and if he hadn't been sitting down he would have fallen down. There was no fear, only nervousness in the pit of his stomach and a strange trapped feeling in his head. Her words had instigated imaginings that were shocking, exhilarating and nerve-racking all at the same time.
The girl was prepared for a little rebellion, she was used to such things in the first phase of a plan. She arched an eyebrow and a grin tugged at the corners of her mouth, then with the flat of one hand she laid a sharp smack onto his soft, flushed cheek, not hard, but hard enough to bring his teeth together with a click.
"Oh!" Her brother flapped his hands and his 'too pretty for a boy' eyes took on a vague unfocused look. "Oooh! Jennifer, what...?"
"Don't make a fuss, or I'll start being cruel." she told him. "When you're with me you must be obedient. I thought you would have realised that by now."
Abigail's moist eyes held her gaze for a moment, then looked away. She had such a commanding voice it never occurred to him to refuse. Rubbing the sting on his face sheepishly, he capitulated.
Jennifer smiled inwardly as she stroked a finger tentatively up the side of his face. The sweet lamb knew exactly how luscious he looked, but was reluctant to admit it.
She drew him forward by his hips, taking his penis in her hand to savour the texture of its spongy tissue and tensed sinew for a moment before stroking its length a couple of times. It was primed and ready to be worked over by a knowledgeable hand. But not yet, not for a while yet. There were things to do before he deserved any pleasure of that kind.
"Up you get, and do a little shimmy for me." she told him.
Abigail paced back and forth a bit, casting worried glances in her direction each time he turned. Obediently he rolled his hips and pouting over his shoulder in the manner of a precocious tart when the oh-so-bossy Jennifer demanded it. His stiff, unrestricted penis, bouncing above his testicles and wagging about ridiculously in front of him as he minced back and forth did nothing to cool the heady erotic nature of things.
Jennifer's non-too-professional eye didn't blink as she watched it extend from the top of his trim young legs, and Abigail secretly sort of wished he'd been given a skirt if only to cover up the sign of his embarrassment.
Eventually Jennifer called a halt and beckoned him forward to stand in front of her. "It's gratifying to find you accepting sissyhood so gracefully, Abigail," she husked. "Stand up straight, heels together, arms by your side,"
He turned to go back but she caught him by the arm. Her other hand went to the back of his head and pulled his mouth against her own. Her hot tongue licked his lips and then forced a way between them, just the way a man likes to do with a woman; aggressively, filling his mouth.
She slid her tongue in and out of my mouth for a full minute before coming up for air, and his whole being focused on her kiss, which seemed to last an eternity. When he pulled back he could taste and smell her lipstick all over his mouth.
He felt lost and confused, and he groaned into her mouth as she took hold of his cock, sliding the smooth skin up and down its hard core until slick moisture began to erupt from its tip. It felt so good to have her rubbing his penis. Her fingers felt so sensual, her grip so comforting.
She whispered in his ear. "You're such a lovely prick-tease. So much bigger than any of the others in this place. There are veins in your shaft, and the head is kind of purple. Poppy is the only one who can compare with you, but he's such an effeminate bimbo he's not any real competition."
He shuddered slightly when she stroked her fingers lightly under his ball-sac. His upstanding penis slavered slick, clear juice from its tip, but there was yet to be no release for its impatient main cargo.