Away with the Lads

You're invited to Dublin, Ireland with 10 other lads from your village. It's planned as a weekend of copious quantities of drink (Guinness), fast food (beef burgers and chips) and cultural interest (Girls). You fly from Southampton and costs are kept to a minimum. Aiden, The only Irish born lad in the group fails to show – selfishly this is good news, as unlike the others you now don't have to share a room. This means after checking in to the Hotel, the Harcourt, and surveying your room, a large double bed with 2 singles, a window overlooking the front with bathroom, you step out of your jeans and slip on the pretty white panties you had concealed within your case. You smile with pleasure as the silken material slides easily up your smooth shaven legs. The panties are extraordinarily delicate and lacy, adorned with tiny roses and two beautiful bows. You sigh and fall to your knees to gaze at the ladies magazine you've opened on the bed. You stare jealously at the glossy pages of the beautiful fashion models. In a dream like state you slip a quivering hand into your panties and grasp your throbbing cock. Mmm! You dream your dream, of feminine dresses, towering high heels, sexy lingerie and beautiful long flowing hair. Soon you're pulling on it like there's no tomorrow. You close your eyes and groan like a teenage girl as you imagine you're dressed in the sexiest dress ever with 'fuck me' heels, sheer stockings and a plummeting neckline that shows off your eye-popping cleavage. You toss your imaginary hair back and wrap your pink painted glossy lips round a hard throbbing cock. It's a common, popular dream, one that you've fantasised over every detail and now it's like visiting an old friend. You're hot, turned on and in heaven, so ecstatic you don't hear a card drop in the security lock. The front door slowly opens as you scream with pleasure and shoot your creamy load into your clean white panties.

Bang! The wooden fire door springs shut. Startled you look up to see Aiden in the doorway with his suitcase. 'What's going on hear?' he gasps. You turn bright red and struggle to stand your legs weak and wobbly from copulation. Aiden laughs walks into the room trundling his suitcase behind him like a dog.

'I, I, I thought you weren't coming,' you stutter.

'Hmm! I can tell,' he pants dragging his case further in. 'Fortunately I caught the next flight.' He looks at you; you're panties and the damp stain that's spreading in your gusset. 'You fucking sissy,' he screams. 'You pathetic pervert!'

'Please!' you plead. 'Don't say anything to anybody.'

Aiden sneers. 'What's it worth? I'm sure the lads would love to know your little secret.' He throws his suitcase on the double bed. 'I've always had my doubts about you - you don't drink, you don't smoke, you never mention a girlfriend and...' He breaks off to walk around you looking at your long smooth legs, fleshy arse and full lips. '…You do look so effeminate… Yes,' he confirms, 'you would make a beautiful sissy. Now how long have you felt this way? What else do you do and how far do you go?' But he doesn't give you a chance to answer as he rips open your suitcase. 'What other sissy things have you got?' he says enthusiastically. 'A sexy dress or perhaps a boned Basque, high heels, fishnet stockings and suspenders.'

'No, no,' you scream but before you can stop him he's found your pretty babydoll night-dress in bubblegum pink.

'Oh, Sissy what have we got here?' he holds the delicate fabric up to the light and the sun streaming through the window reveals the transparent nature of the dress. 'Cor! My lucks in, if I don't pull at the hotel night club I look forward to seeing you wear this later tonight.' He grins and tosses you the night-dress as he resumes his search. You hold the dress lightly in your quivering fingers and slouch depressed on the end of the bed like a naughty schoolgirl. Needless to say he finds your matching pink panties, hard jelly butt plug and a tube of lubricant. He chuckles like an old prospector finding gold. Eagerly he searches some more but seems disappointed. He shakes his head. 'Well, well, well, would you believe it? - What a surprise. Fortunately for you and unbeknown to our friends downstairs I rather like sissy boys.' He puts his pointed index finger to his lips, 'But shhh!' he whispers, 'Don't tell!' He cups his bulging cock through his jeans and gives it an affectionate squeeze.

You heave a sigh of relief. 'So you won't tell about me then?' you say with a slight smile.

'Wooh! Slow down, I didn't say that but… I'm sure we could come to some mutually beneficial arrangement.' He grins devilishly and thought for a few moments whilst staring at your slender hairless body. 'If you want me to stay silent,' he says eventually, 'I want you to dress for me tonight.'

'What!' you say unsure of his demands. He laughs and rubs his large handsome hands together delighted with his own suggestion. 'Yes, I want you to dress for me tonight.' he repeats. 'In something short that clings, shows plenty of leg and is incredibly sexy.' He licks his lips hungrily, 'Something feminine that is convincing yet shows the world that you're a party girl.' He smirks again and his eyes twinkle like a sex-starved beast. 'As I'm sure once in a sexy dress and on that dance floor you'll party like a fox.' You blush and squeeze your knees together feeling your own cum soak into your gusset.

'Oh!' he cries, 'And I almost forgot underneath whatever you choose I want to see your sissy frame squeezed into a curve inducing boned corset.'

'B... B... But you've seen what I've brought with me. I haven't got anything else.' You feel tears form in your eyes but Aiden is unconcerned. 'That's not my problem. You'll have to buy something pretty later today. I'm not joking; I want to see you shaking your cute arse down in the club tonight. And... I want you looking so gorgeous; I'll want to lick you all over. I'll be pissed but I hope you don't disappoint me.' He laughs cruelly and slaps your bottom hard. You're not entirely sure what he means and though he has mirrored your dream you shiver with apprehension.

'I didn't know you were... Or liked...' stopping short of finishing the sentence afraid to say the word Gay or Sissy.

'Oh my darling Sissy there's lots you don't know about me but don't look so upset. Dry those dazzling eyes of yours - from what I saw a moment ago you'll love every minute. Now keep those panties on your butt, put your jeans back on and lets join the others for a few drinks as if nothing has happened – we don't want to arise suspicion. Remember... That's why we're here.' He shakes his head and smiles with delight. 'This is such an unexpected bonus and I almost ended up missing out or sharing with Stinky Pete.'

'B... B.. but my panties they're not clean.' You mumble.

'So what's the problem. I want you to wear your cum soaked panties - it will remind you of the pervert sissy you are. Besides I want you suitably girlish and submissive for later on.' He turns his attention to the jelly plug found earlier in your case. 'Talking of which. It seems a shame not to use this.' he says pointing it at you like a conductors baton. 'Especially since YOU brought it. Do you need a hand getting it in?'

'No, no, thank you I can manage,' you babble but he's not listening. He grasps the plug and applies a big dollop of lube on it. 'Drop your knickers, Sissy, bend and hold your knees.' You hear a forceful tone to his voice and terrified he might turn nasty you do as he directs sliding your sticky panties down your svelte thighs so they are just over your smooth buttocks. Knees together you bend over and feel him press the cold jelly against your sphincter. You gasp as he teases your glory hole before sliding it slowly home. 'Good girl, work that muscle! I don't want you too tight tonight.' Satisfied he slaps you patronisingly on your rump for good measure. 'You read the agenda?'

'Hmm! Pardon,' you say squirming slightly as you shift your weight slowly from foot to foot letting the large plug settle deep within you.

Aiden checks the email he got from his pocket. 'We're to meet downstairs in the hotel bar for a welcoming pint of Guinness and then we plan to see the city in an open top tour bus.' He yawns. 'Boring… but now I know your little secret and what you've got tucked away, the trip will be far more interesting. Nothing beats a sissy boy and I know you'll be warming up for me later.'

Downstairs you all chip in with a kitty and begin drinking. Pint after pint they down as they watch the Rugby on the large TV screen, belch, fart and generally talk loudly about recent sexual conquests and sporting events. After about three pints of Guinness each and you've dragged out your orange juice you all amble out and head for the high street. Aiden says nothing as to what he saw earlier or shows any interest in you and after a while had it not been for your damp panties or stretched and stuffed arse, the events in your room would seem but a distant dream.

Predictably you crawl from pub to pub stopping for more pints mainly at those with live acts playing traditional Irish music. After about an hour while in O'Donoghue's, Aiden glances at his watch and whispers in your ear. 'Don't forget our arrangement. You don't want to miss the shops.' He's right it's 3 o'clock so you excuse yourself from the pub, and walk into the city centre with a smile on your face as the jelly plug shifts deliciously with every step. You window shop for ages before plucking up enough courage to go into a ladies fashion store, 'Ave Maria'. You're terribly embarrassed and after a fleeting glance around the shop at its expensive designer labels you see an understanding looking female assistant. At first she thinks you're trying to chat her up but after a few moments you explain that you want to buy a sexy outfit for your girlfriend that night. She's happy to oblige and is none the wiser until she asks for your girlfriend's size. You're not sure but you give her your dimensions and guess a likely breast measurement. After some embarrassment you choose a sexy black mini dress made from a sumptuous silk crepe de Chine. 'If you want a pair of pretty heels,' she says studying your feet and own shoes, 'I recommend 'Cherche Midi' they're just down the road and their stock is swooningly high and shamelessly fashionable.' You giggle stupidly. 'And,' she adds, 'they specialise in larger sizes.' She smirks and you blush relieved when she wraps the dress and asks for your credit card. You glance around the sumptuous little store - you're still alone. 'And can you also recommend where I can get a corset from?' You ask. She looks at you suspiciously and gives the directions of another store, 'Susan Hunter'. 'They're the oldest lingerie store in Dublin, its hugely popular and have over 20 years experience. They have an emphasis on high-end luxury labels.' she smirks, 'but I'm sure you're worth it. If they can't help no one can.' You thank her, pay for the dress and walk to the shoe shop.

Shoes - They seem the easy option. After the embarrassment of buying a dress you wanted something less challenging before you tackled the corset. And as you expected buying the heels was an altogether easier affair. They where all arranged on a rack in sizes so once you found your size you simply selected an elegant high heeled pair that you thought would compliment the little black dress and enable you to dance with toppling over. They where gorgeous, dead sexy, with a 3" heel, pointed toe and plenty of straps. You're convinced they alone would make you the woman you want to be. The cashier again looked at you rather strangely but she took your money happily and as she wrapped them you asked for the direction for Westbury Mall off Grafton Street for the supposedly oldest lingerie shop in Dublin.

'Susan Hunter' was slightly off the high street and rather seedy looking. A wave of nervousness washed over you as you pushed open the door. You're grateful that it's empty.

'My Names Jileen, Can I help?' an attractive motherly looking lady in her 50's asked.

'I, I, I want a corset for my girlfriend,' you say lying badly. Jileen seemed pleasant and understanding but still she frowned. 'I'm sorry it's almost impossible to supply a well fitting corset without a personal fitting. What's her approximate size?'

You tell her your dimensions and she stares you straight in the eye. 'Are you sure Sir? Or is there something else you wish to tell me? We are very discreet. Can I get you a cup of tea while you think about it?'

The floodgates open as you sip her sweet tea and tell her everything – well almost everything. You fabricate the truth slightly – you say you need to dress as a woman as you've been invited to a private party at the Harcourt and are going in fancy dress with your girlfriend who is going in a suit as the man. She seems taken in with your story and as a bonus she's kind and genuinely sympathetic.

You follow her into a back-office fitting room and upon her instructions remove your T-shirt forgetting that the waistband of your panties is clearly visible. She notices but says nothing commenting only on your smooth flawless skin. After taking your measurements she fits you with a bone-crunching corset. It has an amazing effect on your already tiny figure squeezing your waist in a further 4 inches. Jileen is delighted with the results and as you parade in front of the multi-angle mirror trying to breathe normally Jileen looks at you thoughtfully. 'Excuse me for asking but is your dress in the bag?' she points at the two large plastic shopping bags by your feet.

You nod, 'and shoes,' you say proudly.

'Good, good,' she says, 'and have you any other lingerie?'

You look at her rather sheepishly but say nothing and she knows the answer. 'May I then suggest I find you something suitable?' You nod. 'But my darling you do realise your lingerie tonight should not be selected for reasons of warmth, comfort or hygiene. You need to eroticise your body.' She waggles her finger like a schoolmistress, 'Don't underestimate the power your sexy underwear will have over your boyfriend.' She laughs and gives you a knowing wink, 'I think even a girl would appreciate a boy in this quality lingerie.' You both laugh but your merriment is short lived as Jileen suddenly resumes her more business like pose. 'What about breasts,' she says. 'You've got to have a convincing cleavage? May I suggest some soft touch gel bra pads? They're new in and feel like natural breasts.' You smile, nod and stare transfixed in the mirror as she slips back into the shop returning moments later holding a collection of raunchy lingerie. 'We are not busy in the shop, why don't you slip your jeans off and pop your dress on for a dress rehearsal, I'd like to see if the corset fits under tonight's dress before you leave the shop.' She smiles reassuringly, 'Judging by the bags, you've chosen some beautiful things; it would be a shame to spoil everything for the sake of a few minutes.' You can't believe your luck. You'd rather make a fool of yourself in the intimacy of the small fitting room rather than under the bright lights of the club tonight and your mates. After all it was essential that you looked sufficiently convincing that no one knows your true identity.

Minutes later with some struggle you slid your arms into the sleeves of the dress. Now your legs are encased in sheer stockings affixed tightly to a lacy suspender belt, Your feet are squeezed into your beautiful high heels, your waist is squeezed to pronounce your curves and your chest is heavy with a bra that is brimming with a realistic pair of tits. Jileen zips you up the back and as she clips the zip hook into place you feel beautiful – like a fairytale princess. 'Show me,' Jileen says and like a catwalk fashion model you strut up and down the carpet, swinging your hips and swaying your hands from side to side. The butt plug is still in place and as the heels heighten your swagger the sway of your hips in turn magnifies the sensation in your butt. You feel gorgeous, so feminine and so girlish. The dress had an almost magical effect – as well as looking like a pretty girl dressed up for a night on the town you felt like a girl that needs to hang off the arm of a strong man and for a moment you remembered what Aiden had said. You shiver in apprehension and for a terrifying moment you feel your panties moisten.

Jileen sees your pleasure and studies you from every angle. 'Perfect, my love but you need to do something with your hair.'

You look worried. You had forgotten about your hair. 'Can you recommend someone?' you say.

'Yes, I do know a wig specialist.' She said picking up the telephone, 'I'll ring ahead to get you an appointment and avoid any embarrassment.

You smile - Everything is perfect. Perfect, apart from the price but like the dress after you'd changed back into your jeans and T-shirt you longed to put it back on. Finally satisfied with your purchases you pay her and went in search for the wig specialist.

Muriel in the wig shop is very helpful. She sat you in what looks like a barbers chair and asked what look you wanted to create. Like Jileen she made you a tea and made you feel completely at home before putting the first wig on your head. You felt awkward. 'Relax.' she said combing it into place. But you feel far from relaxed. 'Its very hard too when I look so masculine.' you say. Muriel smirks looking at your small frame and delicate features, 'don't kid yourself Honey I know more masculine looking girls than you.' This surprisingly didn't help, you look dejected and rather dispirited at such a late stage of your transformation. 'I tell you what,' Muriel says in an attempt to make you feel better, 'why don't I put some colour on your face and you'll look much more the part.' You nod and as you do so she spins your chair so you're facing her. She opens a huge make-up box. 'My, my, my you have perfect skin - a flawless, glowing complexion -this shouldn't take long,' and within a few minutes she's put on a light foundation, eye-shadow, mascara, eyeliner and lipstick. 'You have amazing bone structure. You have supermodel cheekbones. And your lips are so sultry,' she sighs. 'So soft and kissable, so smooth and pronounced. You look fabulously subtle and so natural.' You're gob-smacked you smile and for the first time she notices your teeth. 'Oh my goodness, I'm so jealous. You have beautiful white teeth and your smile is so sparkling, the boys won't be able to keep their hands off you.'

It's true – for the first time your face looks amazingly feminine and as she stretched another pretty wig over your head the reflection that now shone back was that of a pretty girl. 'Oh my goodness!' she cries clapping her hands I think we have the one. Darling you look radiant, absolutely fabulous, like a new woman.' You blush, stand and walk about the room feeling your new hair swinging with every step, kissing the sides of your face and caressing your shoulders. Muriel winks, 'You're such a pretty thing your boyfriend won't recognize you,'

'Girlfriend,' you correct her.

Muriel flicks a few stray stands of hair off your face with a brush. 'Sorry, love, Jileen has told me about the party and looking like you do you'll have a fabulous time.'

You think she's right so you thank her for her help and pay for the wig and an assortment of cosmetics. Later after you've cleaned your face she hands you the bag containing the wig. ''Oh and darling I bet you dint bring any perfume?' You hadn't. 'Thought as much. I've put in one of my favorite fragrances. We cant have you looking like a beauty and smelling like a builder. Its an enchanting blend of floral fragrances and is so pretty. It's on me. I've had a lovely time this afternoon and I thank you.'