Damsel In Distress

1. The Request

Duncan was fond of his older sister, Helen, but she pushed the boundaries of brotherly love to its limit when she asked him an unusual favour. 'Let me get this straight.' Duncan said, lounging on his bed whilst listening to the radio. 'You want me to escort you on a date with some guy you've just met.' Helen fluttered her long eye lashes. 'That's right.' She said sweetly. Duncan had a voice reminiscent of a little girl, all squeaky and bouncy with false innocence. '. . . But that's not all. You want me to dress as your . . .' He paused as the full magnitude of what she asked sunk in. 'You want me to dress as your girlfriend.' Helen smirked. 'Sounds silly I know, but before you dismiss the idea please let me explain.' Duncan shook his head. 'Not a chance. No way. Wipe the idea from your mind. I'm telling you right now Helen. Forget it. OK? Forget it!'

She was not put off and she put her hand on his knee in an affectionate way. He could feel the slight roughness of his trousers on the tender skin of his thighs. The feeling wasn't unpleasant.

'It's imperative you come as my girlfriend. You're my only hope.' she said assertively knowing nothing about his dark secret and childhood longing. Duncan preferred his sister not to know how much he wanted to wear her soft and feminine dresses, lacy panties and bra. What's the rush? He had plenty of time. She'd ask again he was sure of that. Perhaps then he'd agree. He smiled to himself. No loss of face giving in after a struggle. Go on he mused, persuade me. Duncan considered himself broad minded and Helen had asked some odd things of him over the years but this took the biscuit. Two years had elapsed since he wore her school pinafore to a fancy dress dance and he'd enjoyed every minute. He loved wearing her shoes, her dress, her make-up. The only disappointment was not wearing her panties and bra but he didn't want to suggest it for fear of looking too enthusiastic. His little cock began to harden as memories of the evening came flooding back.