tagTranssexuals & CrossdressersDamsel in Distress (5 & 6)

Damsel in Distress (5 & 6)


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.


5. Lesson 2

'Lets see what we have here.' He said, peeling back Duncan's floral summer dress to reveal his lace suspenders and panties. 'Oh la la,' and with a forceful hand he tore his panties down to his knees. Tears began to roll down Duncan's face. He couldn't bare another seeing to under the masterful hand of Steve so when he was off guard Duncan quickly pulled up his knickers and skipped to the waters edge. Foolishly he glanced behind to see the none to pleased Steve pick himself off the floor and give chase.

'Come here.' He cried clearing his throat then spitting forcibly towards the river.'

Near the waters edge the grass was slightly wet and Duncan in his heels quickly lost his footing and slid down the bank feet first. His pretty dress rode up his waist and his panties cut deep into his bottom crack. Splash, his feet hit the water.

'That will teach you to try and get away. Where do you think your going dressed as a pansy boy?'

Duncan didn't care as his feet hit firm ground and he saw Steve laughing behind him. He held his dress high with one hand, balanced on each foot and removed both shoes one by one. Then he waded further into the water and although it was ice cold he didn't mind, desperate to escape. Steve laughed like a crazed hyena and seemed reluctant to follow.

'You'd better watch yourself these rivers are quite treacherous.' He shouted.

Duncan didn't hear as he let the icy water rise over his knees and to the tops of his nylons. A step further and it was lapping against his crutch. Still moving forward he felt the first lacy edging of his panties make contact and then they where completely submerged and hugging his form. About five metres along the bank was what appeared a small sand bank. As he got nearer he realised it was a piece of flooded ground that was still slightly below the level of the water. An escape route he murmured but his foot sank in the mud and the soft mass slid up past his calf. He grasped a tree root and his legs sank deeper and he experienced an utterly new sensation as the mud held him gently in it's all embracing caress. He heard Steve laugh even louder as he moved from one stockinged foot to another. With each reversal sinking lower and lower until when the mud almost reached his crutch, he came to the solid bed of the river. He slipped and sat back and felt the soft brown mud oozing up over his genitals until the whole of his lovely panties was engulfed in the mire, any movement sent an electrifying thrill through his whole body. He struggled to get free and as he moved his legs up and down he felt sensations he had never dreamed of. He was close to tears as he noticed his wallowing in the mud had completely fouled his lovely panties.

'Ahoy there.' A girls voice called and Duncan looked up to see a punt approaching. In it where six girls, all of Helens age and of student appearance. The girl at the front held out a hand to Duncan.

'Jump aboard and stop your crying.' she yelled.

Jump, Jump, he could hardly move and it took three of them to manhandle him onto the deck.

'Christ, your a mess.' Said a girl called Sue looking at the mud stuck to his legs. 'Lets get you back on dry land.'

Duncan didn't know what to say as they pushed the flat bottomed boat off the sand bank. They where as drunk as he but they expertly positioned the punt alongside the riverside beside the awaiting Steve.

'Come to Daddy.' He sneered.

'Sorry were late.' Duncan's rescuer shouted.

'You took your time joining us, we've dunk all the beer and eaten all the food.' Steve said.

'Sorry.' She said, 'You know what us girls are like. We spend an age shopping.'

'Shopaholics,' said one girl as she held out two large plastic carrier bags aloft. 'Who is this beauty we have saved from a watery grave.'

She turned to Duncan who lay exhausted on the bank his once beautiful dress soaked and heavily soiled with river mud. He sniffed back a tear as Steve explained.

'Say hello, Cindy.'

Duncan smiled and said hello, his make-up smeared over his face like a road crash.

Helen was still nowhere to be seen and without her protection he was convinced further humiliation was to follow. He was wrong . . ., initially as to his surprise the new girls where most understanding and sympathetic. Even though he assumed they didn't know his real identity

'Lets get you cleaned up.' One of the girls said, putting a comforting hand on his shoulder. They led him to the river bank. 'Slip out of your pretty dress and I'll rinse it for you in the clear water. If you're lucky it will be dry within the hour.'

'Thats very kind but what do I wear in the meantime.' He questioned.

'Don't worry.' Said an attractive blonde named Emma. 'I'm sure I bought an outfit today that if it fits your welcome to borrow.'

In his anxiety, Duncan didn't recognise the attractive Emma as his sisters best friend or see anything suspicious in her offer.

'Thank you,' he said relieved to be back amongst friends. He glided out of his dress like it was Christmas wrapping. Playing it for all it was worth not wanting them to suspect a thing. It was, as it stands, worth plenty as he had the kind of figure that gets noticed. Its his sex that let him down. He sponged himself down with a face flannel Helen had packed in their picnic. Dry within minutes Emma handed him a minute, sleeveless, black and red micro dress.

'It's not really appropriate for a day at the river, more suitable to a wild party night but it will at least contain your modesty.'

Jean, a timid looking girl with black spiky hair and similar build gave him a brand new pair of panties, still in their packaging. He turned his back to them shyly as he stepped into the lycra dress pulling it upwards over his huge chest. It was slightly too small and the material squeezed his arms as he slipped it over his shoulder. The dress was hardly fit for the purpose finishing just below the crutch and only just containing his amble chest.

'How does it feel,' Emma asked. 'Good fit.'

'Hmm!, Sleazy, I feel like a quart in a pint pot,' Duncan said, wiggling his hips and smoothing what he could of the dress down over his slender thighs. His legs where lily white under his dirty and laddered stockings. 'Slip these on,' she said, handing him a pair of cheap black fishnets.'

In his dirty shoes even before they refreshed his make-up he looked like a common tart.

'Dry your eyes, your mascara has all run, lets see what we can do for you.'

One of the girls handed a large make-up bag to Emma.

'A girl always feels better with a freshen up and a new face.' She said fluttering her own dramatically painted eyelids.

The girls tittered cruelly for the first time as Emma brushed more pink blusher to each cheek. Layer upon layer did she apply until his cheeks positively glowed. 'Oh, Cindy you look so adorable I can't believe our Steve was so lucky to find you.' Next she trowled yet more eyeshadow and mascara on. Finally she took a tawdry bright red lipstick and smeared an overly thick coat on to Duncan's lips. Once done Trish applied an inexpensive gloss to his lips so they would really shine. Whilst receiving his gaudy makeover he was oblivious to the other girls chatting to Steve.

'I think I may have over done the make-up. You look more like a tart than a demure teenager.'

'A course one at that.'

'A tenner a trick.' Trish added.

They giggled amongst themselves and pointed rudely to bits they liked. 'Look at his lips. See his pantie line, I don't believe his cleavage.' Mean while Emma's mind worked overtime. 'Now that you look like a tart show us you can move like one to.' The girls taught him some basic moves and he was soon gyrating around the field in front of them much to their amusement. That's right they cheered swing those hips, stick out that chest, strut your stuff.'

Emma looked at him cruelly. 'Do us a twirl,' she asked

Duncan did and the girls all clapped enthusiastically.

'Now guess what a tart like you really appreciates?' she said.

'A good rodgering,' said Steve who had already unzipped his fly's.

Trish chipped in. 'I don't think that's exactly what Emma had in mind, actually.'


Steve smiled and scampered over to the picnic hamper.

Emma interjected. 'I mean all girls like champagne and. . . being taken from behind. So I thought we could give Cindy an extra special treat. A treat only a girl can savour.'

Steve nodded. 'OK, I'm in, lets play swallow the bottle.'

Emma grinned.

Duncan gasped in dismay. 'Please no, what have I done to deserve this? Why the sudden change of tune? What have I done to deserve this?'

A smile slalomed down Emma's face, 'I initially felt sorry for you. Boy wants to be girl, I can relate to all that. I was even happy to welcome you in as one of our fold until Steve told me you're Helens brother. Helen my supposedly best friend who wasn't going to come today unless you came along. Yes you Duncan, you've caused me so much trouble. Talking of which where is your sister Helen and my boyfriend Paul. She looked around her in an exaggerated gesture. 'I blame you for his unfaithfulness and you deserve everything your going to get.'

Emma's hand gently caressed Duncan's cheek. Duncan shuddered.

'Pretty girl, We won't hurt you as long as you don't struggle. The choice is yours. Struggle and suffer or relax and enjoy. So you will do as we say. . . won't you?'

Duncan looked at Emma and the non too friendly girls that surrounded him and decided he had no choice.

'Er! Yes, I guess so,' Duncan said meekly.

'Good girl, now go and see what surprises Steve has got for you over by the tree.'

Duncan nodded weakly and lifted his head in supplication as under the shade of the oak Steve shivered in anticipation.

Duncan accepted Steve's kiss as he held him tightly and coaxed the strange fire to grow once more.

'Down on your knees, nancy.' Steve commanded.

Duncan froze and so Steve dragged him to the ground like a lion about to devour its prey. His dress rose higher as his fishnets clung even tighter to his smooth legs.

'Growl.' Said Steve as he positioned the picnic hamper in front of Duncan and pushed his face down over the wicker. Emma put the heel of her shoe on his back and pushed him forcibly down.

'Help.' He cried as he lay doggy style supported by the empty picnic box.

'Perfect.' Steve cooed.

'Help me.' Cried Duncan. 'Someone please help me.'

His shiny hair fell forward over his painted face as he struggled to support himself with his hands. He couldn't see what was happening but he heard the group of girls gather behind him.

'Now stay there,' Steve shouted as he crouched down behind Duncan's proud bottom, turning towards the onlookers. 'Its show time.' he cried, imitating Fester from the Adams Family.

He continued for his audience, 'For today's performance, I am proud to reveal Cindy.' He grasped the edge of Duncan's tight fitting lycra skirt and peeled it gently back as if peeling a banana. The material was stretched tighter than a drum and he had to use both hands. 'There,' he said as he eased the skirt finally over his pert pantie glad bottom. The audience cheered as Steve slapped it venomously. 'As you can see ladies and gentlemen Cindy is not all she appears to be.' Steve pushed Duncan's legs wider apart and clamped his muscular hairy hand in-between his crutch.

'Yes.' He cried, 'Our Cindy has a hidden secret.'

Duncan winced as Steve closed his hand around his diminutive cock.

'My, my ladies I do believe he enjoys the humiliation. I can feel something s.t.i.r.r.i.n.g.' Duncan groaned he couldn't help himself as his little member stiffened.

'Let me reveal to you today, this day of days, all Cindy's hidden charm,' and with one brisk movement Steve tore down Duncan's panties.

'Hey!' Shouted Jean, 'They're mine.'

'Silence,' Emma snapped, 'Don't spoil the show.'

Everyone laughed and Steve now spurred on by the crowd slapped a generous dollop of fresh cream from the strawberries they enjoyed earlier over Duncan's naked buttocks. 'Hmm!, nice,' he said as he massaged the double thick goo well into his crease. 'Fancy some more champagne,' he joked as next he picked the remaining gold foil off the bottle neck.

Duncan crouched frozen, as immobilising swathes of terror wrapped themselves around his body.

'Perfect.' Steve said teasing the opening of his hole.

'Please, God, someone save me, I don't want to be subjected to anymore humiliation.' Duncan sobbed shamelessly.

'Sorry,' Steve apologised, 'it's not Moët Chandon.' He tutted 'Take a deep breath,' as he slowly pushed the bottle deep inside. Duncan screamed, like a mournful prairie dog as he thrust his hips forward in a vain attempt to escape the bottle that probed his bottom.

'We're Smokin,' he cried, 'You are new,' as the bottle met with some restriction. 'I'll put my money on you not having done this before. Am I the lucky one to pop your cherry?'

Steve sighed and giggled with glee as the full length of the bottle neck was imbedded in Duncan's buttocks. The fresh cream was an admirable lubricant as Steve pushed the bottle in and out faster and faster. Duncan moaned his saliva-sodden scream curdled the air as he twisted his head sharply to one side to witness his virgin arse raped brutally by a cheap brand of champagne.

'Argh!' Duncan cried out in pain and tears rolled down his painted cheeks as he realised no matter how degraded he felt, how sickened he was dressed in his sisters frock, whilst being continually used and abused as a sex toy Duncan's own member was hard and throbbing desperately wanting to release its load.

The girls clapped and cheered as Steve powered relentlessly on, in and out, in and out like a high revving engines piston.

'More, more, faster, faster,' the girls cried but his momentum was suddenly called to a halt.

'Stop, stop, stop, this instance,' Helen shouted, appearing from a copse of trees. 'What's been going on? What on earth are you doing?' She gaped open mouthed at the spectacle before her.

The pause was long and sinister.

Emma broke the silence, 'He bought it on himself, he did. If it was not for him you'd not be with my man, Paul.'

'I'm sorry,' Helen said.

'Hold on girls,' Paul interjected, 'You're all jumping to conclusions. Helen and I are not an entity we have just been walking. I want you, Emma my love. Always have done, always will, you know that?'

Emma looked unconvinced and Helen looked annoyed. Together they spelt trouble.

'So what was that then,' Helen said, implying the last sixty minutes. 'One hell of a strenuous walk?'

Paul shrugged his shoulders, 'It meant nothing.'

Helen turned her attention to Emma, 'If you've got a problem sort it out with me and not my brother. Aren't you man enough?'

Emma laughed 'I'm more man than your brother will ever be.' Glancing over at his feminised form.

Paul ran over to Emma and tried to comfort her with a non to convincing embrace.

Helen looked at Duncan. 'I'm sorry,' she said, 'this is all my fault lets get out of here.' Duncan didn't need to hear that twice as he struggled to break free.

Steve backed off cautiously as Duncan slowly pulled the bottle from his arse and slipped his panties back on and adjusted his dress'.

Helen looked at the bedraggled Duncan. 'What have they been doing to you?'

'Don't even ask,' said Duncan, 'Take me home, please.' He grabbed the dress he'd laid out to dry and ran to the waters edge.

The others continued to argue as to who Paul really loved as Helen and Duncan slipped silently away in their punt. Only Steve saw them depart and he waved affectionately.

Duncan as oarsman raised plenty an eyebrow as he tried to handle the punt in his short dress and high heels. It's not every day you see a sexy girl struggling on the deck of a punt amongst the studious surroundings of Cambridge. He didn't change until he got home.

6. Safe house

Duncan entered the bathroom whilst Helen ran a hot bath and filled it with her expensive bubbly moisturiser.

'I'm sorry.' Helen said as she helped him out of Emma's mini dress.

'You are what?'


'You are what?'

'What are you sorry for?'

'For everything. For persuading you to go on the date.'

She poured some more moisturiser into his bath.

'How is your bottom?'

Helen hadn't seen his bruised backside as he'd slipped into the hot water.

'Hurts like hell. Probably weeks before I can walk normally like a man.'

She angled her head to one side sympathetically. 'Its over now.'

She mixed the water quickly with her hand generating even more soft bubbles.

'Paul turned out to be quite a disappointment.'

'Spineless.' Duncan added. 'Couldn't fight his way out of a paper bag.'

'Couldn't stand up to Emma could he?'

'At least you know now.'

Helen waved two crisp ten pound notes at Duncan. 'We've made some money out of the exercise too. I collected the deposit they left on the punt when we took it back. We deserve it all don't you think?'

Duncan smiled and sunk deeper into the bath.

'I'll leave your share in this purse.' She picked up his tiny shoulder bag he'd hung on the back of the bathroom door, clipped open the delicate clasp and deposited the note in an internal pocket.

'Silly question, but did you enjoy the day.' Helen asked as he lay stretched out in the hot bath full of bubbles nursing his sore bottom and feet.

'In parts.' He said. 'Now how do I get these off.' He said pointing at his synthetic tits.'

'The adhesive should soften in the bath,' she said 'but be careful. Who knows when we'll use them again.'

Duncan managed a weak smile which vanished, when, without warning the bathroom door burst open and in walked their mother. Duncan stared in disbelief as she strode across the tiles, her gazed transfixed on his amble bosom.

'I can explain.' Duncan began but she just smiled and laughed.

'There really is no need, love.'

Helen smiled reassuringly.

'I know all about your little adventure. Don't you think I didn't recognise my own son when you where on the punt.' She laughed. 'Who do you think lent Helen the synthetics and the wig? Our amateur dramatic group has a vast assortment of props don't you know?' She sat down on the edge of the bath and patted him on the head as one would a pet.

'Do you mean to say you and Helen where in on this.' Said Duncan with a shocked expression.

Helen giggled back at him impishly.

'That's right and what a wonderful idea of Helen's it was too. I just hope you enjoyed the experience as much as we. Now hurry along there's a queue for the bathroom.'

'But why Mum, why?' he asked.

'There is an easy explanation. As you know your father and I are putting together a new play.' She breathed out deeply and oozed flamboyancy with the air and grace of an accomplished actor. 'Its about TV prostitution in France during the eighteenth century. We require a young male actor to play the lead role but no one in our repertoire was particularly keen. Stumped we may have had to cancel the production. . . That is until Helen reminded us of how well you played the part of a pretty schoolgirl some years ago at a fancy dress dance.' She sighed dreamily. 'How lovely you looked in her pinafore and panties.'

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