Damsel In Distress Ch. 01

Nis 27, 2024 // By:analsex // No Comment

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Imagine your sister asking you to chaperone her on a date. Would you? Debatable – Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal.

This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and brutal male rape. I don’t wish to offend so if issues of this nature disturb or bother you please don’t read any further. If you have a open mind and a broad sense of imagination … Enjoy. Tomi

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. The feeling of openness on his legs, how the pinafore hung from his shoulders and the pinch of her shoes, it all added to a truly feminine experience. Of course he never disclosed how much he savoured wearing her uniform that night but somehow she knew. Call it female intuition. She knew. She’d seen him watch her getting dressed or applying her make-up. She guessed it wasn’t childish inquisitiveness – he was jealous. She thought he envied her beautiful clothes, the make-up she wore and the attention she received but what she didn’t know was by how much. Remarkably he hadn’t succumb to the temptation to wear any of her clothes since. Dreams are not to be confused with reality, however strong your desire he’d often mused and actively pushed the notion to the back of his head. Of course it wasn’t easy when his cock throbbed like an engine and Helen was a very feminine girl with all her wonderful girlie things just across the hall it was tough to resist.

Helen sat down on his bed beside him, ‘I’ve met this gorgeous guy, Paul and the other night he asked me out this weekend.’

Duncan ginned knowingly.

‘I said yes and gave him my phone number.’

‘Congratulations, Helen, I hope things work out.’

‘Thanks, but there is a small problem.

‘Yes . . .’ Duncan said apprehensively.

‘He’s currently seeing Emma.’

‘Hello.’ Said Duncan. ‘Emma your best friend. Emma your childhood girlfriend, Emma your inseparable erzurum escort partner.’

‘Precisely.’ She admitted. ‘That’s the problem. I’d love to date Paul but am reluctant to upset Emma. Not until I’m at least aware of his intentions. I don’t want to be just a notch on his bedpost.”

‘Hmm! How is the old girl, Emma I haven’t seen her for years,’ Duncan asked.

‘She’s fine, you know how it is climbing the social ladder.’ Helen said with a hint of annoyance having been interrupted. ‘Paul’s invited me punting in Cambridge this weekend but he wants me to bring along a girlfriend. Apparently there’s quite a crowd going but I dare not invite anyone I know in case the word gets back to Emma. As you know, her friends are mine, so you can see my dilemma.’

Duncan sighed and peered enviously at his sisters long slender legs and short flimsy skirt.

‘To be honest,’ she continued, ‘I’m slightly nervous going on my own. I don’t know much about him or his friends. You never know these days. I don’t want to get involved in anything I can’t handle.’

‘Come on, you can look after yourself.’ Duncan quipped.

‘Maybe.’ Helen said unconvincingly ‘But I’m meeting him actually in Cambridge and you know how unreliable my car is. I would hate to break down miles from anywhere on my own.’ She looked at him with her doey eyes. ‘Please, please say yes, please.’

‘Why can’t I go as I am?’ Duncan asked, fingering the fabric of his own worn jeans.

‘Don’t be stupid I can’t go with a boy it would give the totally wrong message, Paul may think we’re an item. In any case he specifically asked me to bring a girlfriend. You don’t want me upsetting him before we even start do you?’

Duncan smirked. ‘I guess not but it still doesn’t answer the question.’

‘Oh! I don’t know.’ She said impatiently. ‘Perhaps he’s concerned about numbers, doesn’t want too many boys out numbering the girls, who knows.’ Helen shrugged her shoulders and lifted her hands letting them drop loosely by her side.

‘Well, that’s rich since I would really set his sex ratio calculations adrift if I turn up dressed as a girl.’ Duncan shuddered. ‘The thought is horrible I’d be a gooseberry. A girlie gooseberry.’

Helen laughed. ‘Is that all you’re worried about? You really don’t listen do you? We’re to make a group. There’s no way you’d be a gooseberry.’

Duncan had never been one for making impromptu decisions but the proposition did tempt him. He had a petite frame for a boy, very similar to Helens and many family friends had commented how they looked so alike. Perhaps he could pass as a convincing girl.

‘You can help me with the food.’ She said, ‘I’ve promised to supply a picnic hamper. Please, please, help me, you’ll be the best brother ever. Don’t worry I won’t tell anyone and no one will ever know. Mum and Dad are out visiting Don and Betty and you’ll be amongst strangers all day. So what do you say? Yes.’

Duncan stared at her in disbelief. Was she really serious? It sounded to good to be true. He loved the idea if he could only carry it off. As he contemplated her request he momentarily imagined wearing one of her soft floaty summers dresses, sexy lingerie and high heel. It was a once in a lifetime opportunity that he couldn’t resist. But surely he wouldn’t get away with it. The fairy tale bubble burst in his head and disappointment etched across his face.

‘Don’t worry about how you’ll look, with your figure, my clothes and a little make-up you’ll look stunning. It wouldn’t surprise me if you’re the most gorgeous there. Just you wait and see I will transform you overnight into a convincing vision of femininity.’

Duncan looked on the verge of consenting. ‘Well . . .’

‘Come on.’ She urged, ‘Be honest with yourself, haven’t you ever considered what its like to be made up and pampered as a girl. . . all day.’ She smiled comfortingly and placed a reassuring hand round his shoulders. ‘You’ll not come to any harm, erzurum escort bayan you’ll be with me. I’ll look after you.’

A wry smile spread across his face, he pondered what lay ahead. ‘Perfect, just perfect.’ He uttered quietly under his breath. Helen was very persuasive but nothing could suppress her surprise when he reluctantly agreed.

‘You’ll owe me for this.’ Duncan said convincingly.

Helen had difficulty containing her delight. ‘Oh! Thank you, thank you.’ She said. ‘I promise I’ll never forget this.’

That’s what worried Duncan, he hoped she would. Her smile of delight soon straightened to a more businesslike grimace.

‘Don’t think I’m ungrateful but if this is to work its important you act out your role convincingly otherwise I’d hate to think what will happen if were discovered. Can you manage that?’

‘I don’t think I grasp your meaning,’ Duncan said.

‘You do want to be a convincing girl, don’t you?’ She said frowning.

Duncan looked dumbfounded. ‘I guess so.’ He said. ‘Is that what you want me to say?’

Helen looked cross. ‘No, it’s not what I want you to say, it’s what you want to be.’

Duncan wanting to please his sister thought he understood. ‘Yes, then, . . .yes, I do want to be a girl’.

‘Excellent.’ Helen said clapping her hands together. ‘We’ll have a fabulous time just you wait and see. You’re a starlet in the making.’

Duncan frowned. ‘Whatever you say, Helen.’

The weekend flew round and on the Friday night just before dinner Helen reminded him of his commitment. He didn’t want to look too excited or enthusiastic so he pretended to have forgotten. He made his face drop and asked her to explain again what she wanted him to do. The very words, dress, bra and panties sent bolts of excitement through his body, blood rushed to his little cock and his stomach tightened but he did a masterful job of concealing his real excitement.

Later over dinner in front of their parents Helen started the conversion again. ‘If you’re not going out tonight Duncan,’ she winked, ‘we’d better start getting things ready for tomorrow.’

‘What’s happening tomorrow?’ Mother asked.

Helen put down her knife and fork, her eyes sparkling. ‘Oh! Mummy, Duncan and I are taking a picnic and going punting with friends.’

‘That’s lovely dear, do have a nice time, I’ve heard the weather is going to be amazing. You’ll get a beautiful tan.’

‘Oh! I do hope so Mummy. l want to wear my new strappy sun dress.’ She turned to Duncan and smiled wickedly. ‘What are you going to wear, Dunky, something nice?’

Duncan winced uncomfortably and shifted awkwardly on his chair he hated his sister calling him Dunky and he didn’t want their parents to know how he planned going in a dress . Her unfair goading deliberately teased him in front of their parents.

‘I haven’t decided yet.’ He said, giving her a sarcastic smile.

‘Oh Dunky, I’ll help you choose something nice and suitable.’ She said, raising a well-shaped eyebrow.

Their mum smiled pleased to see them getting on so well.

‘Don’t forget we’re out for the day, darling,’ said their father.

‘That’ll be nice, anywhere special.’ Helen asked.

‘Don and Betty’s from the drama club. We hope to discuss the production of our new play. We expect to be back late so you’ll need to take a door key.’ Helen nodded.

After dinner Duncan scolded Helen for teasing him in front of their parents but soon forgot everything as he helped her fill a wicker hamper full of freshly cut sandwiches, salad, cakes and fruit. As a special treat she packed some fresh strawberries, whipped cream and a bottle of pink champagne.

Duncan licked his lips. ‘This is terrific but there’s not that much here, how many are actually coming?’

Helen looked nervous. ‘I don’t know exact numbers but I did tell Paul I’d only provide food for us three. I assume the others will bring some too.’

Duncan smiled, escort erzurum reassured and with the hamper packed she led him upstairs. He always felt nervous in her bedroom. He wasn’t sure why. Was it the feminine decor, with its pastel walls and floral print curtains and matching bed spread or was it her clothes. To be so close to such femininity always made him dizzy and as an untidy girl by nature her room was often strewn with her lacy panties, bras and stockings. Duncan shivered at the thought as he pushed the mountain of soft toys on her bed to one side and sat down.

‘Don’t get too comfortable I want your jeans off for a start. You can be rest assured you won’t be wearing trousers tomorrow.’

Duncans eyes widened. ‘

‘I guess it will take me a good four hours to get you ready so we better do as much as we can now.’

Duncan gasped but loved the idea of starting his feminization early.

‘Now let me see,’ she said, flinging open her wardrobe door, waving her hands proudly at the rails and racks of clothes. ‘Is there anything I’ve worn recently that you’d like to try? Mmm!’ She giggled as she flicked through the rail. ‘What do you think will suit you best; a pretty dress or a blouse and skirt? I’ve always loved halternecks but what colour, hmm? and how long a skirt? we want to show off your long legs don’t we?

Duncan twitched nervously, ‘On second thoughts I’m not sure if this is a good idea,’ he said twiddling his thumbs. ‘I feel ill.’

Helen laughed. ‘You can’t chicken out now I’ve told Paul to expect us. He knows all about you, Cindy and he’s dy to meet you.’

Duncan winced convincingly. ‘That’s my name? Cindy, it’s so girly.’

Helen nodded staring him straight in the eye. ‘I know isn’t it a lovely name. I’d love to be called Cindy it conjours up such a delicate, pretty girl.’ Duncan agreed but he couldn’t tell her that. ‘C i n d y, C i n d y,’ he said slowly over and over to himself. It was perfect. He imagined signing his new girly name. He pretended to be wearing a chain with his new name on it. He heard voices – girlfriends calling him Cindy, Cindy they shouted. His little cock stiffened and began to throb. He was away with the faries.’

‘Look,’ Helen shouted disturbing Duncan from dream, ‘you promised to be a girl for the day so you can’t expect to be called Dunk, wear overalls, talk about soccer and fast cars, now can you?’

Duncan smiled for the first time in about an hour ‘I guess not,’ he said nodding slowly as if his head had grown very heavy. But he didn’t want to wear trousers and talk soccer. He wanted to glide about in a gorgeous dress, wear towering, strappy heels, talk make-up and clothes.

‘Good, Good,’ she tuts, ‘now come on Cindy, be a good girl strip to your briefs and help me sort through my clothes for something suitable for you to wear. If you where a real girl youd love to do this with me.

‘Sorry,’ Duncan says.

‘i don’t want to do this first thing tomorrow morning.’ She said leafing through her extensive collection selecting dress after dress, pushing them against his near naked torso. ‘Let me see.’ She pondered. ‘The weather forecast is fine and as were going to Cambridge we should really dress as two irresistible débutantes all fixed for a lazy day on the river.’ She giggled. ‘Summer dresses, impossably high heels and parasols I think, what’s your opinion?’

Duncan was in heaven. ‘T… T… That sounds fine,’ he said slightly awkwardly. She continued to flick through her clothes and eventually choose him an irresistibly feminine outfit and gave him a razor and some shaving foam. ‘Don’t forget to shave your legs when you have a bath tonight.’ She said.

Duncan looked horrified. ‘Your joshing, right?’

‘No I’m not, how can you expect to be a convincing girl in my pretty dress with stubbly legs, underarm hair and a manly chest, ugh! The thought is quite repulsive.’

Duncan looked down at his hairy legs and chest. ‘I guess your right.’

He eagerly took the shaving equipment from her and stood to leave. He suddenly remembered he should be less enthusiastic so he frowned for effect and closed the door behind him as she chuckled like a naughty school girl. ‘See you in the morning, Cindy. Sleep well.’

‘And you,’ he shouts but he was so excited, so hot, so hard he knew he would hardly sleep at all.

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