Damsel in Distress Ch. 02

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Duncan goes on a picnic.
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Part 4 of the 4 part series

Updated 10/19/2022
Created 08/03/2003
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Tomsparty
Tomsparty
644 Followers

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

2. The new Beginning.

Duncan awoke early. His room smelt strongly of nail polish and he felt something silky on his chest. As requested he had bathed, shaved all over and covered himself in her moisturiser. He didn't go downstairs late last night for his customary milk drink but feeling naked minus all body hair he prepared straight for bed. Just before he put his light out Helen popped into his bedroom to check he'd done what she'd requested to her exact satisfaction. It was then Helen insisted she painted his nails before they retired for the night. She didn't seem to think they would have time in the morning. Duncan didn't complain he liked the smell. Perhaps that was why he slept badly or was it what he wore?

Helen was adamant. 'You have to do this.' She said, but he couldn't come to terms with the nightdress and panties she made him wear. He lifted the bed sheets inquisitively and peered at his feminised form. The rose printed crepe de chine chemise hung loosely around his body from its shoestring straps. It had risen slightly up his body during the night, exposing his hips and pantie clad bottom. She said it would help him get into the mood. "Start the day as you mean to go on," she had said. He didn't agree but it was late by the time she'd selected him a pretty floral dress, shoes, underwear, hat and handbag. Tired and past caring he wore what she selected. Lying in his bed he heard his parents rise, go downstairs and eat breakfast. Later his mum popped her head inside his room to say goodbye and wish them well on their day trip.

'Pooh!' She said wrinkling her nose. 'The pungent aroma of your sisters nail polish gets everywhere.'

Duncan blushed visibly.

'BEEP, BEEP.' The horn of dad's car sounded loudly.

'That'll be your impatient father. Must dash.'

Duncan heaved a sigh of relief grateful for the bed clothes tightly pulled around his neck that concealed the dainty straps of Helens nightdress.

'Bye.' He said as she shut the door behind her.

Helen followed her in as their car drove off down the street.

Helens nostrils flared open. 'Come on, Cindy,' she said excitedly, 'we don't want to be late and I need some breakfast before we go.' She looked heavily laden with one hand carrying their clothes and the other holding a large make-up bag. 'Wake up, Cindy, show a leg.'

Duncan dragged himself up, flung his legs out of bed causing Helen to comment on his pretty nightdress.

'My that's lovely.' She said, 'Have you seen for yourself?'

He hadn't and out of curiosity he checked his reflection in the full-length mirror affixed to his wall. The image that bounced back was that of a pretty young girl.

'I don't believe it,' he gasped. 'It's extraordinary what a few clothes can do.'

Helen handed him a fresh pair of buttermilk coloured knickers. 'Just wait until we've made you up.'

He removed the undies he wore during the night and slipped on the hi-leg panties. Pausing to admire their delicate lace front.

These are pretty.' He said easing them cautiously up his slender legs, slipping his male equipment down to give himself a credible girlish front.

'That's not the only thing that will be pretty by the time we're through. Said Helen wearing a grin the size of a bill board. 'Now sit down in front of me and I'll do something with your chest.'

With him sitting comfortably she turned Duncan to face her and using a gauze pad wiped Duncan's newly shaved chest with a cool lotion. She turned away and dropped the gauze onto the table top and picked something out of the bag she had brought in with her. She turned round sharply and pressed something cold and soft against his left pectoral, holding it firmly in place for about thirty seconds. When she removed her hand a large girl's breast was visible on his chest.

'What on earth are you doing.' He gasped, 'They look enormous and . . . permanent.'

'Don't be silly, 38D' she chuckled, 'Its either uncomfortable padding or these fabulous synthetic breasts. I couldn't get a smaller size so these will have to do.'

Duncan sat open mouthed as she performed the same procedure on his right side. Within a few minutes he was sporting a matching pair of breasts suitable for a well-endowed woman rather than a normal girl of his age. There where no straps, they moved as he breathed and accurately weighted to match the real thing they looked frighteningly real.

'What have you attached them with?' He asked. 'Glue?'

'That's right.' She said. 'Silicone adhesive to be technical but don't worry they will come off. . . eventually. She replaced the pad and lotion into her bag, stepped back and gazed admirably at her handiwork. 'Well, how do you like them?'

'I, I, I. . .' Duncan was speechless as he looked down at his amble chest. 'I'm not sure.' He said, cupping each breast gently with his hands. They felt genuine and when he swayed they moved like the real thing. 'They'll take some getting used to. They weigh me down and pull me forward.' He said walking round the room.

'Show me.' Said Helen gesturing with both hands. She smirked. 'You boys have it so easy now perhaps you can imagine how us real girls feel.'

'This is all rather serious.' He said frowning. 'Are you sure all this effort is necessary?'

'Absolutely, we don't want Paul and his mates to discover the truth, do we?'

Duncan nodded, 'I guess not.'

Helen slipped a matching Wondabra in the same buttermilk round his new breasts. 'This is new, it cost a fortune but the effect will be priceless.'

It was, he looked stunning.

Helen giggled. 'I had to buy the bra special as you're a few sizes larger than me. Even the woman in the lingerie shop questioned the cup size as I think she thought i was buying for myself.'

Duncan winced and stood up as Helen placed a lace suspender belt around his waist hooking it in place behind. Next she told him to sit back down while she helped him slide a pair of silky cream, seamed stockings up his shaved and moisturised legs.

'How do those feel?' She asked adjusting his seams and attaching the lace tops to the suspender straps, poking them inside his panties.

Duncan bent at the knees and ran his hands down his stockinged legs. 'I feel . . . I don't know how to describe it. . pampered.' His wide eyes went from his long slender legs to Helen. His mouth softened into a smile.

'Helen.'

'Yes.'

'Why have you dressed me in such provocative undies when the last thing I want to do is attract men?

Helen blinked. 'I want to reward you for your girlishness, by treating you to some sexy underwear. Feel right. Look right.'

He had to agree he did feel increasingly feminine and he couldn't believe how convincing he looked as he watched his transformation in the mirror.

'Its remarkable.' Duncan nodded. 'I do look like a girl.'

'You do.' Helen added. 'You certainly do and seeing you wear these feminine things is making me feel sexy.'

He waved his arms to his sides feeling the material swish seductively on his hips. 'Good,' he said, 'Good.'

'Now are you ready for your first step towards being a woman.' She said as she held out her dress.

'Yes.' He said unfolding his arms underneath his amble bosom. 'I think I've past the point of no return.'

He took a deep breath and stepped into the flirty summer sun dress of yellow and pink pastels. He held his breath, his stomach fluttered, he felt dizzy and once again his cock twitched and throbbed. Helen couldn't help but notice yet she politely choose to ignore it instead she concentrated on the dress. He felt the dress tighten as she buttoned him up securely.

'I choose florals so you blend in with nature and it's got enough room so you can sit cross-legged on the grass.' She said merrily.

The cool cotton dress was slightly see-through, without being obviously revealing. 'Just enough to turn an admirer on,' Helen joked.

It had a deep scooped neckline in front that showed his fair skin down to his huge bosoms. The full skirt flared from the waist extravagantly. The bottom of the dress just about skimmed the tops of his sleek, brown thighs. Even without heels, his legs looked endless. He fingered the long split that ran almost to his crutch and thanked her for choosing something tasteful.

'You what?' Helen said.

'Classy.' He repeated performing a gentle twirl cheekily flicking the dress up pver his pert bottom. He was entirely satifsied with the result.

'Don't laugh but I originally envisaged having to wear a skirt not much wider than a belt.'

'Who do you take me for? You'd look like a tart. Or have I mistaken your real desire having preferred to dress like a floozy?'

'No, No, No.' Duncan said sharply. 'If I have to wear a pretty dress, this is the style of dress i'd choose.' He waved his arms loosely at his side feeling the material sway from his jutting out breasts. 'Yes this dress is fine.' He repeated.

Helen smiled broadly. 'Good, don't even think you can wear anything other than a dress.'

He wasn't going to complain any more. Just a token gesture he thought. Whilst adjusting his skirt she placed her hand on the back of his thigh, stroking his silky skin. Then very softly, very faintly, she moved upwards. Tendrils of excitment trickled through him. Through the thin viscose of her dress, she shaped her hand over the curving mound of his buttocks. He squirmed. He clenched his internal muscles. What was happening to him? He moaned his mind began to wander he forgot it was his sister and wanted her to undress him, feel him, openly explore him. His cock throbbed hot and strained for release. She laughed aware how aroused she made him.

'Before we go out i think you need to go to the bathroom,' Helen said.

Duncan blushed and though he remained silent as she fussed with his dress he looked forward to pulling his own panties down and reliving himself.

'Later,' she said directing him to sit back down in front of the dressing table. He swallowed and tried to clear his head. he was so hot he began to worry about soiling his beautiful panties. While he faced the mirror she again rummaged in her bag.

'Are you going to be an ugly duckling or a swan?' she asked, 'lets find out' and she produced a beautiful long auburn wig. Standing behind him she held the base of the wig and stretched it tightly over his head, pulling it down tightly over his scalp.


'Perfect.' She said, grabbing a soft brush from the dresser and pulled it energeticaly through his mass of auburn hair. Tendrils of hair framed the edges of his face, enhancing his pretty, fresh features She was grinning with pleasure. 'As I thought a swan.'

'Where did you get all these props from,' Duncan asked in amazement as he tossed his long mane back in a characteristically feminine way.

'That would be telling, but I have a very helpful accomplice who is understanding to my cause. Oh, but Cindy don't worry your pretty little head with incidentals you're looking prettier and prettier with everything I put on you. Now lets make you up.' From the large make-up case she choose a suitable foundation and put a smooth even coat on his cheeks, nose and chin. Next she applied pink blusher to each of his cheeks.

'Oh, Cindy you look so beautiful,' Helen said. 'I will have to watch Paul more closely than I thought or he may run off with you, my pretty girlfriend.'

She expertly brushed on more colour. After that she put powder on him to soften the colour of the blusher.

'We don't want you looking too tarty now do we.'

Duncan dare not move his head afraid Helen would make a mistake but the look on his face was one of acceptance.

Then she took an eyebrow pencil and outlined each of Duncan's eyes. Next she put eye shadow on his lids and mascara on his lashes. With one fell swoop the supremely wide wand had lengthened his lusciois lashes to a length every girl hankers after.

'I don't know why I'm bothering with this,' she said, as she spread the mascara thinly on his lashes. These are so long they're positively gorgeous.'

Finally she took some bright red lipstick that matched the colour of the polish on his fingers and applied a thick coat to Duncan's lips, outlining them perfectly.

When they had both dressed Duncan accustomed himself to wearing his sisters' heels. He nurtured a special fondness for her shoes and the cream coloured leather slingbacks with their three inch heel were amongst his favourite. As he expected they fitted perfectly and matched his ensemble beautifully. Standing up and feeling the pull of the tightly suspended nylons and caress of the flimsy cotton dress awoke a sexy feeling deep within him. A feeling he never knew he was capable of experiencing. A feeling that frightened him. A feeling that questioned his genuine gender. He shivered and shook his head to dislodge the alien sensation.

Helen rummaged in her chest of drawers and retrieved a matching purse which she dropped onto his shoulder. Then she gave him a few pointers in how to walk.

'Don't think I'm patronising you but us girls walk differently from you boys and you do want to be a convincing girl, don't you?.'

Duncan nodded.

'Place one foot directly in front of the other to give yourself a wiggle and keep your legs close together as you walk. You should feel your nylons rub against one another with every step.' He paced the floor a couple of times and then followed Helen downstairs to the kitchen. He wasn't particularly hungry, only eating a small breakfast of cereal and tea.

'I haven't felt this nervous since I took my driving test.' Commented Duncan.

He then helped Helen load the hamper of goodies into the boot. Stepping into the morning sunshine wearing the dress rekindled the unnerving feeling within him. It was a totally new sensation; the cool wind on his stocking clad legs, the gentle caress of the skirt hem and the sway of his heavy breasts against his chest.

Helen watched Duncan mince round the car carefully.

'Cindy.'

Duncan had to think twice before replying. She was talking to him and calling him a girls name. He sighed. 'Yes.'

'I forgot how transparent and floaty these dresses are but whilst you stood with the sun behind you I could see straight through your dress and can clearly see your shapely legs. Lets pop back upstairs for we both must put on a slip.'

They did and Duncan now fully accepting his female role happily slipped the silken slip up his legs and under his skirt. He felt strange before but this additional layer of polyester heightened the feeling of slipperiness and as he moved its caress sent electrifying shivers all over his body.

'There.' She said doing the same. 'We want to leave something to the imagination, don't we?'

'Hmm!' He murmured.

Back outside Duncan dug the map of Great Britain out from under the cars front seat and studied the route to Cambridge. Helen still busied herself running in and out the house.

'Slow down.' He said. 'You don't know how odd this feels. You not helping me relax.'

Helen scowled. 'Tough! Don't be such a sissy,' she muttered, 'just because you're wearing a dress doesn't mean your incapable of doing anything'. She gave his bottom a hearty slap. 'By the time we get to the pub you'll consider yourself a true girl.'

'Pub.' Said Duncan, peering up from the map. 'You never said anything about a pub.'

'Didn't I,' she replied, 'I must have forgot.' 'That's where I arranged to meet Paul.'

Duncan's stomach churned. 'Do we have to? Couldn't you have chosen some place less public?'

'Yes we do.' She barked. 'Now don't be so pathetic you're getting to be an embarrassment.'

Tomsparty
Tomsparty
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