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."
