Damsel In Distress (3 & 4)

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

3. Cast Off

The morning haze soon cleared and the sun strengthened tremendously as they journeyed up the M11 motorway. Helens supposedly unreliable car performed amicably but rather than watch the road Duncan couldn't take his eyes off his long slender legs stretched out before him. He just couldn't believe how his slingbacks extended his legs but his stunning looks didn't keep him from playing nervously with the material of his dress whilst crossing and uncrossing his legs. The journey was not as pleasant as he had envisaged. The seat belt was uncomfortable. Its harness cut deep across his chest squishing his huge breasts and Helens window open played havoc with his long hair. He cursed and checked his make-up in the vanity mirror repetitively.

'Stop worrying.' Helen said realising his apprehension. 'Relax, you look lovely.' She held the steering wheel with her right hand and squeezed his thigh gently. 'We'll knock them dead.'

As arranged she parked in the grounds of the "The Granta Inn" adjacent to the boat yard. With its traditional pub décor and patio overlooking the mill pond and Sheep's Green it was heavily favoured by tourists. Duncan's dress fluttered as he jumped out of the car exposing his white thigh and lacy stocking tops. Characteristically of a woman he looked around slightly embarrassed.

'Cindy.'

'Yes, Helen?'

'Now you're a girl,' she smiled amiably, 'I want to give you a bit of advice.'

'Yes?'

'Try to remember you're a demure young lady not a boisterous lad.'

Duncan looked down at his pretty dress. 'I completely forgot. You girls, how on earth do you do it?' He cradled his temples with the flats of his hands. 'There's just so much to remember.'

Like true girlfriends Helen took Duncan's arm lightly and led him proudly into the bar. As they walked across the polished wooden floor their heels clicked noisily sounding their arrival causing the men to turn and eye the approaching talent. Duncan felt slightly queasy.

'I'm not sure if I like this.' He said quietly, but Helen tightened her hold on his arm and steered him towards the bar. Both girls giggled nervously as two boys whistled appreciably as they strutted across the floor, wiggling their hips.

'You'll be fine with some alcohol inside you.' She smiled at the barman and looked at Duncan. 'Well what'll you be having Cindy?'

He looked at the vast assortment of real ales. 'A pint of Boddingtons please.' He automatically replied.

She smiled sweetly, fluttered her eyelids and whispered her order to the young barman who poured two port and lemons. 'If this is going to work,' she smiled at Duncan, 'you have to remember your the young and feminine Cindy not some beer swilling lad out on the town.'

'OOPS! I forgot again, sorry.'

'I know you did Cindy just try and be more careful. Dressed as you are I don't know how you can be so absentminded.' She flicked his skirt and removed a small stray hair.

Duncan sipped his drink effeminately and noticed the lipstick mark his painted mouth left on the glass. 'I feel totally embarrassed watching all these guy's in jeans and T-shirts'.

'Why's that?' Asked Helen.

'I didn't mind dressing in all these lovely female clothes when I was just with you in the security of your bedroom but now I'm amongst other men I feel out of place. I should be among them instead of wearing your pretty summer frock and passing myself off as a girl.'

Helen smiled. 'You're so sweet sometimes, but please don't worry.'

Duncan took another nervous sip of his drink. He hated port and lemon.

'Helen, Helen.' Shouted a strong male voice and before they could look up from their drinks they where joined by Paul and a mystery man.

'Hi.' Helen said with obvious delight.

'Hi, babe,' said Paul. 'Glad you could make it.'

Paul was good-looking with red hair and the body of a committed rugby player. The other lad was black haired, slender but equally as muscular, his name was Steve.

'Have you met Cindy before?' Helen asked.

'No.' They both said.

'I haven't had the pleasure.' Steve added.

'Hello.' Said Duncan, as a pink blushed his new feminine face.

Steve rudely stared at Duncan's breasts. Tasty he thought I'll get myself a piece of that later.

They chatted politely up against the bar as Helen gazed into Paul's eyes and Duncan did his best to avoid Steve's lecherous stare. He flicked his hair backwards and moistened his lips as Steve looked at him the unmistakable way a man looks at a woman, only Duncan wasn't a woman.

At a suitable moment Duncan excused himself to powder his nose.

'Come on.' He said to Helen. 'Please come with me.' Helen smiled, what a feminine gesture she thought as they both picked up their handbags and tripped silently to the ladies.

It was hot. Paul wiped his forehead with a handkerchief. 'See you in a minute girls.'

Once out of earshot Duncan hissed at Helen. 'What on earth have you done pairing me up on a blind date with a bloke.'

'Quite.' She said bayoneting Duncan with a look. 'Wait until we're in the loos, they may hear.'

Duncan paused before he followed her inside the ladies unsure of the legality of what he was about to do.

'Hurry up, you look suspicious just standing there, no one will know. Don't attract attention to yourself'

He gave the ladies icon a sideways glance as he pushed open the door.

It was, as he'd expected, very similar to the men's toilet but there was no urinals and the section reserved for hand washing was larger. Inside three girls gossiped as they eyed them suspiciously as if trespassing. One was spaying some strong perfume down her blouse, another retouched her lipstick, and one hitched her skirt up her thigh and adjusted her stockings. Duncan couldn't help staring.

'What's a matter love, can't you see?' She laughed, pulled her skirt down and left with her two friends.

Helen looked at Duncan and sensed his concern. 'Look.' She said, also retouching her lipstick. 'Don't give me a hard time I only repeated what he told me. I feel awkward about this too.'

Duncan winced. 'Not as awkward as me. That's for sure.'

'Look, Dunky, Steve's a nice guy, can't you just go along with the charade. He needn't know and we will be home in a few hours.'

Duncan was adamant, 'No.' He said brushing his long hair. 'I want to go home. Now'

Helen looked annoyed. 'How can you be so insensitive this means so much to me and your prepared to throw it all away.'

'Dammit Helen. He said scowling. 'I'm sorry, but you're asking too much.' Helen ignored him and started to walk towards the exit.

'Hold on where are you going.' He said.

'Back to the boys. If you want to ruin your day go ahead but I'm staying here.'

'But how can I get home?' He asked.

A tight smile flashed on to Helens face. 'Not my problem.'

'Damm you Helen. It is your frigging problem.' Duncan's voice rose half an octave and he looked set to weep. 'You've got me over a barrel, Helen, I will have to play along with your charade.' Duncan shrugged his shoulders, stranded he had no choice. 'I only wish I'd brought a spare change of clothing.'

'That's better.' She said giving him a peck on the cheek. 'You'll enjoy the day it'll be fun. Just relax, pretend you're all woman.' A older lady entered the toilet and disappeared into a cubicle. 'That's an idea, while you're here do you want to go?'

He did and for the first time in his life he went sitting down like a lady. What have I done to deserve this he thought as he sat with his head buried in his hands, looking down at his skimpy panties gathered round his ankles and the skirt bunched round his waist. This is all getting rather out of hand.

When they eventually emerged the two lads had found seats and they gestured for them to join them.

'Over here', Paul shouted. Duncan noticed how they smirked to each other as he sat down and slid his handbag under the table. Did they know? Was it obvious? Had they guessed?

They stayed in the bar for a further hour and the lads kept them well lubricated with spirits. Steve seemed a respectable lad. Duncan could have even considered him as a mate, not as a boyfriend especially while wearing a skirt. Helen proceeded to obviously drool over Paul embarrassingly while he teased her cruelly occasionally patting her thigh. Duncan shifted uncomfortably in his chair. 'When are we going punting?' he said impatiently.

Paul took a long pull at his pint of beer. It was cold and felt good going down his throat. 'Soon.' He said. 'Soon.' He lied . . . it wasn't until after their fourth strong drink that Paul eventually suggested they go and after knocking back the dregs they all ambled outside into the bright sunshine. Paul took Helens arm affectionately and Duncan avoided Steve doing similar by switching his shoulder bag from hand to hand nervously.

'You spoke of a group. Where are the others?' Duncan asked inquisitively.

'They'll join us on the river. Some of the girls wanted to do some shopping first.' Paul explained.

'Lovely historic city Cambridge.'

'Great shops,' Helen added, 'You know what us girls are like.'

Duncan smiled and perched Helens large sunglasses on the bridge of his nose and went to collect the hamper from the boot of the car. Steve rushed over and offered to carry it for him.

'Thank you,' he said smiling sweetly, 'you're a gentleman.'

Steve grinned and placed a firm hand on Duncan's shoulder. Duncan trembled and pulled away sharply.

'Let's catch up with the others,' he muttered nervously. They waited for the road to clear as hoards of students cycled frantically past. At the boat yard the two lads dolled out the twenty pound deposit and a further fifteen pounds for three hours hire.

'Will you be travelling on "The Backs" or up river to Grantchester?' the girl at the pay desk asked.

Duncan and Helen looked at each other blankly. 'Up river,' Paul replied and the girl stamped their ticket accordingly and waved them towards the awaiting boat hand.

A squalid little man of ragged appearance came forth and eyed the ladies hungrily, 'I have your punt ready. Step this way.'

They all clambered into the punt gingerly and stashed the hamper under the front seat.

Duncan felt the little mans eyes tearing through his light summer dress and appreciated the slip he had so almost forgot.

'Have a nice day lads,' the boat hand said in a dirty voice.

4. Lesson one.

The day was idyllic, a soft breeze blew, the sun shone and a colourful array of birds chirped merrily. The water was calm and the two lads took it in turn controlling the punt. Duncan was grateful he wasn't required to exert any stamina as the lads struggled with the long poles. Funny he thought but dressed in the flowing summers frock and frillies he felt as if his muscles had wasted and his normal strength drained. He didn't mind. . . it felt applicable.

He huddled alongside Helen at the front of the craft and they both stretched themselves out displaying their pretty dresses to the two lads whilst admiring the beautiful period buildings of the university. The dainty parasol that Helen brought along was a great idea. What ever lad wasn't steering sat in the centre of the punt.

Duncan grinned as he dangled his hand over the side and broke the water's surface with a long nail. He closed his painted eyes, Hmm! He murmured as the day's events washed over him. This is the life, he mused feeling the constriction of his bra on his huge breasts and the panties riding high on his hips. He moved slightly and his body slid between the silky slip and pretty cotton dress. He took a deep breath in satisfaction and the scent of women's perfume reached his nose. Its situations like this he could quite imagine how it might feel to remain a girl permanently. Bliss he thought, what a beautiful day.

Paul, taking his turn to punt, broke the silence.

'Does anyone know those four people?'

'Where?' Helen asked, sitting up and looking ahead.

'Next to the Queens college, on the bridge. They're waving frantically as if they know us.'

'I know two of them.' Steve said. 'That's Don and Betty from my drama group.'

Helen turned around and looked at what they where both staring at. She squinted in the sun. 'Isn't that our parents,' Helen said to Duncan quietly.

Duncan froze. He'd never considered his Mum and Dad would come to Cambridge for the day with their friends. 'I don't believe it,' Doug whispered back to Helen. 'What shall we do?'

'Nothing,' Helen said cheerfully, as she waved.

'Hello.' Cried their mum. 'Hello Helen, Hello Cindy. Having fun?'

'How does she know my name,' Duncan asked, 'and who does she think I am?'

'Do stop fretting you'll start hyperventilating at this rate,' Helen whispered, 'I probably mentioned during the week that you where to join us. Smile, relax and wave back.'

They past under the bridge and they all waved.

Duncan flushed. 'Oh Gawd! Dads got his bloody video camera and he's aiming it this way.'

'Say cheese.' He shouted.

'I'm dead.' Duncan said.

Helen by this time was getting a bit short tempered. 'Quit worrying they didn't recognise you. How can they possibly, you don't look like their son but a pretty girl. Enjoy.'

Their craft drifted silently on and they soon left the busy city of Cambridge for the tranquillity of the open countryside. Paul suggested they stop when they see a suitable spot for the picnic. It wasn't long before he chose a picturesque setting shaded by a large oak tree in a field magically carpeted with millions of spring wild flowers. He moored up while Steve helped the ladies out of the punt. It rocked as they both stood. Helen squealed and Duncan unsteady in his flimsy high heels tottered precariously let out a shrill cry and gratefully accepted Steve's supporting hand as he helped him onto dry land.

'Thank you. You're most helpful.' He said politely.

Helen and Duncan busied themselves with the picnic things. First they laid a large car blanket on the tall grass, then spread the contents of the hamper neatly in the centre whilst Paul produced a football and leisurely kicked it about with Steve.

'I don't believe some men,' Helen said, watching the two lads running around the field. 'Here we are two attractive ladies, beautifully dolled up and what do these men do. . .play football.' 'No offence meant but I ask you? men they are stupid sometime.'

Duncan looked relived. 'If you want my opinion,' he said, 'they can kick that bit of leather until we are due back at the yard. I would rather they play with that than me.' He fiddled with the hem of his dress and flicked an imaginary crumb off the pastel coloured fabric. Helen laughed and when they had laid everything out they both relaxed, drank some wine and chatted. Duncan unsure of how to act copied his sister where possible and sat in a similar position with his legs together folded underneath his skirt.

'Isn't the day just terrific,' Helen said, stretching out and letting the sun tan her legs. Its days like this I'm so glad to be a woman and wearing a skirt. How about you Cindy?' She hitched the hem of her dress above her knees to ensure she received maximum sun.

Duncan laughed nervously. 'I wish you'd stop teasing me but dressed as I am and with you talking to me in this manner I can quite forget my true gender.'

'Good,' said Helen, 'that's precisely the object.'

Duncan did feel quite relaxed and he was beginning to enjoy being dressed as Cindy. I couldn't do this as Duncan he thought as he picked some wild flowers nearby and Helen showed him how to make a pretty garland.

'Here.' She said. 'Put this on.' and she placed her handiwork gently on his head. 'I wish I had a camera,' Helen said, 'you'd make such a pretty picture all dressed up in this beautiful field by the riverside decked in wild flowers.' She smirked. 'So pretty, so very pretty.'

The meal was delicious and after they had consumed the beer and champagne they all collapsed in a drunken stupor on the blanket.

He hadn't felt this good for ages. The champagne bubbles had gone to his head and Duncan felt very peculiar but still sufficiently sober to feel an adventurous hand creeping up his stockinged thigh. He sat bolt up right and glared at Steve who quickly withdrew.

'Sorry.' He said, 'I don't want to appear forward.'

Duncan scowled hard at Helen for some moral support but she was busy playing tonsil tennis with Paul and by the look of things they becoming quite heated. Duncan turned back towards Steve who without warning tore Helens sunglasses off his face and taking hold of the back of his head pushed his mouth towards him. The pretty garland broke and fell from his long hair. Steve's lips locked firmly to Duncan's as his tongue invaded the privacy of his mouth. He enthusiastically crushed his firm lips to those of the surprised Duncan as his hands caressed his neck and back. He kissed him long and hard and it was some time before Duncan could break free.

'What's the matter,' Steve said. 'Don't you like the kiss of a man?'

Duncan blushed. What the hell was he to do?

He'd have to play along. He just hoped Steve didn't expect to go too far on his first date. Duncan smiled politely but Steve took this gesture as a green light and lunged a hand at Duncan's right breast. He squeezed hard and looked happy with what he found. For once Duncan was glad he'd listened to his sister for having made him wear the synthetics. What would he have done if he'd felt crackly tissue as his hand massaged and caressed his breast. Without any encouragement Steve became more and more amorous and his hands began to wander enthusiastically over Duncan's skirt and stockinged legs. Duncan cursed his dress as however he sat the material gaped openly displaying a large expanse of slender thigh and lacy stocking top. All much to the delight of the excited Steve who sprang forward for a second sitting. Duncan momentarily struggled to break free but something strange happened. As Steve caressed his skin through the cool fabric of his dress and played with his soft, silky hair, he momentarily forgot who he was and relaxed. Was he the feminine pretty Cindy or the masculine Duncan. It really was confusing.

He enjoyed Steve's attention and succumb to his advances, kissing his date back strongly. It was a terrifying sensation as the groggy Duncan temporarily lost control, his penis stiffen in his silken panties and he yearned for release from the taut fabric. His body began to tingle, he felt a hand on his leg move up to his bottom, massaging it with his fingers, finding the lacy edging of his panties and slowly pulling them down. What's happening to me he thought as he grappled to retain a hold on reality. I am a man, I am a man he said to himself repeatedly as he fought to break free from Steve's strong embrace. Sensing something was wrong he relaxed momentarily allowing Duncan to scramble up, regain his composure and skip daintily away from the salivating Steve.

'So you want to be chased do you?' He rasped picking himself off the rug.

Helen hearing the commotion but oblivious to his danger also pulled herself away from Paul and ran off in the opposite direction.

'Catch me if you can.' She taunted and scampered among the long grass and wild flowers. She, of course, hoped to be caught but Duncan didn't and ran like the wind in a desperate bid to outrun the advancing Steve. It was hopeless of course in his high heels and restrictive skirt so Duncan doubled back when he could see he was losing ground in the hope for support from Helen. Exhausted he collapsed back on the rug and realised in horror she had gone.