tagTranssexuals & CrossdressersCaught by the Past Ch. 03

Caught by the Past Ch. 03

byTomsparty©

Chapter 3 - Friends United

Previously - When you dressed as a sexy tart for James he showed two sides to his character. Bent over his knee, stuffed with a butt plug and forced to suck his cock. What more could he possibly do?... Read on

After sucking his cock you sit on the sofa supported by a fluffy white cushion, shoes kicked off, legs curled under your lap. Dressed like a sissy whore you relax as best as you can, your arse muscle stretched wide open by the butt plug. But you've become accustomed to all the strange feelings... You even begin to enjoy being James's girl. He gives you a set of long false nails and a bottle of scarlet polish. Sticking them in place is quite a challenge but you enjoy painting your new nails. Each stroke of the brush makes you feel even more like a girl and soon you're sporting a set of gleaming red talons Cruella De Vil would be proud of. You wave your hands to dry as James looks on approvingly.

You're so engrossed in what you're doing you barely glance up when you hear voices and laughter outside. But then the front door bell rings - that got your attention. James doesn't move a muscle.

'Answer the door, Babe.' he says irritably. You want to refuse. Why should you? You're not his skivvy, it's his house but you feel compelled do to everything he asks. You're enjoying yourself and feel confident that you look beautiful and convincing. You believe you look so good whoever is at the door won't see through your disguise.

'Hurry up!' he says.

Obediently you leap to your feet, ram your towering heels back on with painful haste, straighten your skirt and totter to the front door.

As you lift the latch the door burst open and three men spill in. The men straighten themselves up, nudging one another and grinning. By the look of then and the faint scent of beer they brought with them, they'd come straight from the pub. They're a motley crew, ugly, over weight, scruffy and stand out in stark contrast to James. Your fishnet-covered legs are brushed by the cold outside air and you cross them slightly in a coy fashion. You sway slightly in your fuck-me heels, wonder if they like this sort of thing and suddenly feel underdressed. You tug the hem of your leather skirt down and almost break a new nail. You feel threatened and reach for the phone on the wall. 'What do you want? Who are you? I'll call the police.' Two of the men collapse in giggles the third blinked in a confused fashion then grins and made an attempt at straightening his jacket.

'No, it's all right. You're safe. We're friends of James. I'm Guy and this is Steve and Ian.'

Light dawned. You relax. 'The stag party.' You say.

There heads nod vigorously. 'We told Jeremy we'd call in.' Said Guy. The other two snigger again.

'You must be Sissy, James's new girlfriend. He said you'd be coming tonight.'

You nod and feel you face flush crimson.

Their eyes burn into you mentally taking off your skirt and blouse as they stride in. 'Huh! Not bad, Sissy. Not bad.'

Once in the lounge James introduces them again, you smile at them individually and hang off James arm for emotional support.

'This is Sissy.' he says, 'as you've guessed. She knows how to work a short dress and please any man.'

You blush again, fearful of what James is planning.

'Curtsey for my friends, Honey, lets not be rude.' His friends all study you hungrily as you click your heels together and bend at the knee as much as the tight skirt allows.

'Oh! and lads just look at her beautiful nails. She's spent hours doing them for us.' James laugh fills the room. Deep and grainy, it reverberates in your stomach and, just for a moment, calms you.

You waggle your fingers at your admiring audience and smile. 'All the better to scratch you with, my dears,' you joke.

Slap. James strikes you on the face. 'Cheeky bitch,' he cry's, 'Your hot little mouth is for sucking not for talking. Show my friends what you're good for.'

You look bemused.

'Show them your... G-string give us all a show.'

Your cheek stings and you want to cry. You're shocked by his assertiveness, you want to collapse and your eyes begin to water. You're now even more nervous of the lecherous lads and terrified you won't please you turn and bend forward holding the window sill for support.

'I don't normally do this,' you say looking behind, your curly hair obscuring your face.

'Shut it slut!' James shouts. 'Who said you can talk. Tart!'

You sniff back a tear and wave your arse at them sexily in a vain attempt to satisfy.

'B... B... but I don't,' you cry.

'What did I say slut,' he growls, 'you've asked for it. Don't move a muscle,' and he leaps off his chair slides your skirt over your hips and tugs the huge butt plug from your arse. A loud sloop echoes around the room shortly followed by gasps of awe from the lads as the full size of the butt plug is realised.

'See this guys only a sissy slut could swallow this big bung.' They all laugh heartedly. 'Help me lads, Sissy talks too much, she needs to learn some manners.'

As if meticulously rehearsed they all huddle round you. You panic but before you can straighten James pushes a large phallic object into your mouth. It's long, wide and cold. You gag gasping for breath. But lips stretched wide, unable to utter a sound some stretchy straps are pulled over your head as if a horse with a bridle. A clasp clicks defiantly shut and your trapped wearing some modern day medieval headgear.

'Now shut the fuck up you ungrateful winging slut.' Your lips stretched wide your tongues pushed flat into your pallet and the rubber cock almost touches the back of your throat.

'I think you need to learn who's wearing the trousers round here. Who's boss, who's in charge.' From a sideboard he pulls a large wooden paddle.

Terror etches across your brow.

'Ian get the ice cubes. And Sissy drop them.'

Reluctantly and with some trepidation you hook a long nail under the spaghetti side straps and wiggle your butt, easing your g-string down to your knees. The lads notice the dried seed stains and smirk amongst themselves.

'Now slut bend over me.'

Steve holds your feet and Steve holds your hands down. Then Ian reappeared carrying a large bowel of frozen cubes.

'How many cubes will this cute arse swallow? I'm taking bets.'

Immediately they start arguing amongst themselves. You hear them shout numbers randomly, '10, 15, 20'

The first cubes the worst. James inserts it slowly until its half way in then flicks it home with a plop. The cold ice cube sends wild internal sensations throughout your body. 'Mmm!' you murmur. Then one cube at a time he slips in another counting out loud as each one disappears inside you.

'When I'm done I want you to thank me for the attention I'm giving your asshole, Honey.

After a while your arse feels like a stuffed freezer at Christmas with no room left for even a mince pie.

'Bet that's cold.' he says

You nod unable to speak.

'Well after this paddle starts tanning your arse things will soon heat up and you wont be thinking about that asshole full of ice.

Your arse is held high in the air as you lay over his lap expectantly. He wields the wooden paddle menacingly. 'This will hurt, slut.' He chirps. You wait nervously, tensing every muscle until the first blow strikes you squarely on the rump. Slap! The lads all cheer and you feel the ice crunch and compact inside your arse. Slap! It does hurt but not very much. Everyone's pain threshold, and yours isn't terribly high, but each time the paddle smacks your lardy arse, it feels as if you're being stung by a petulant bee that changed is mind mid-sting and withdrew. Initially there is no ache of after-sting. It's bearable. Surprisingly he didn't hit hard, but after 20 slaps it did begin to sting. Your corrective punishment, if you can call it that lasts about ten minutes, but as he slaps you one last time your arse had begun to glow red and swell.

'As the cubes melt you'll be a messy girl. A tiny g-string won't cope with your sanitary problem.'

Released systematically you stagger to your feet. Bruised and tender you clench you're arse muscles tightly; its no good, a dribble of water escapes, spots your skirt and runs down your leg. Then to your amazement James hands you a large baby's nappy with elasticised legs and Velcro side fastenings.

You look at him bemused.

'Don't look so fucking dim. Every girl has a child within waiting to grow up. Now unhook your stockings and put this on.'

You do as he directs and when you look up, Steve's holding a beautiful white dress with gorgeous puffy sleeves, sequins and delicate white lace all over it. Ian holds a pair of frilly white over panties and matching rubber panties. Guy is holding a pair of white satin shoes and white tights.

'My friends like Sissy girls and they've brought you all sorts of little sissy clothes. They want to dress you up and have you nurse their cocks as if they were bottles of milk.' He laughs

'Now hurry before the ice melts. I don't want my carpet ruined. Put these things on.'

The guys watch, mesmerised as you perform a reluctant striptease. James puts on a CD and to the music you step out of the skirt, slip off the blouse, shoes and fishnets. The lads all grunt with approval. Then with just the nappy and bra on you step into the rubber panties and pull the party dress over your head. You sit on the edge of a chair carefully and slide the white tights up your legs. Guy holds out the over panties and he winks frighteningly at you as he slides them up your legs under your skirt. Soon you're transformed from a tarty slut into an angelic baby girl. Though the red nail varnish looks rather out of place.

'I look like a Snow Queen.' you say flicking your skirts from side to side.

'Fucking Snow Queen! That's rich and you've an arse full of ice.' Ian says while lighting a cigarette, 'Sissy thinks she's a snow queen, the slag, fucking fairy queen more like.' The others laugh as Ian roughly drops a sparkling tiara on your head and Steve gives you a toy fairy wand. Guy clips some lacewings on your back and they all chuckle at your humiliation. You are a fairy and to confirm the matter they make you perform a pirouette. They laugh like crazed hyenas but you can see from the huge bulge in their trousers that they're very turned on. Laughter abating they gather round you lifting the layers of your skirts examining your frilly panties.

'Isn't she pretty,' chirps James, 'what a transformation.'

'Wave your wand, Sissy.' Guy asks.

Begrudgingly you waft it in the air and to your surprise it emits an electronic tinkle and the star on its tip flash brightly.

'I feel stupid,' you mumble through the cock gag whilst shaking your hips so that your layers of skirt flutter outwards with a loud rustle.

'Nonsense you look like an angelic little girl. A party girl. A fairy.'

Flash - you see yourself being dressed by your mother into a similar party dress while the girl you've befriended watches on in awe with her own mother.

'Stop dreaming little girl,' Guy teases. 'We're hungry.'

'That's right, honey, I know you've already had a snack but conjour us something up or if you can't muster any magic order us some takeaway while we watch the game. The takeaway menu on the kitchen table'.

You want to refuse, to run, to hide yet strangely you don't.

Thankfully the restaurant delivers. If you had to walk into the high street.... The thought wasn't one you want to dwell on. Your hands shake as you read their requirements and get some comfort from the kindly lady who takes your order. But reading the order with a mouth of rubber cock is incredibly difficult and you're asked to repeat many items and are still fearful of what you might get.

'Name,' she eventually asks.

'Sissy,' You say nervously. The lady chuckles and recites your order. 'It will be 30 Minutes, Sissy.'

Back in the lounge the lads are glued to the telly watching the game. James beckons you closer.

You wait patently, sip diet coke on James's lap trying desperately to stop any water seeping from your arse by clenching the muscles in your arse. You must look like a schoolgirl waiting for a particularly fearful exam. Twenty minutes later the doorbell rings James brushes you off his lap as if dirt.

'Snap to it, Sissy. Your purse is by the door. The food won't walk in on its own.'

His friends titter childlike.

You try in vain to move your mouth to protest.

'Be a good girl, darling hurry.' James adds.

Your eyes light up, as he knew they would with any show of affection.

You smile, obediently brush your dress down and check your hair in the mirror. You look good despite the huge cock gag strapped to your face - it must be a good omen. Riding on your confidence you rummage in the handbag and open the door. The deliveryman smirks on noticing your gag and fairy dress. He then can control himself no longer and laughs as you hand him the money and he gives you the food.

'And don't forget to give the change to your Daddy,' he says sniggering. You're emotional. You're so humiliated you begin to cry.

Back in the lounge James has stopped the video and they all seat at the large dining room table. The dining room was ultramodern, with a large table made out of onyx and modern knives and forks and weird crystal glasses. It was all amazingly stylish, but you could hardly see for tears. You can't even say anything.

'Hurry up, Sissy we're starving.'

You hurriedly dish the food out onto five plates and serve it to the lads. As you lay your plate down James looks at you appalled.

'What do you think you're doing honey? Your meal is under the table and I do believe you've got four big helpings.' He chuckles to himself and distributes the contents of your plate amongst the others. 'If we leave anything you can have what's left- If you're still hungry.' More sniggers.

You nod.

'God! You can be unbelievably dumb. It's true that beauty and brains don't go. Come here you thick slut you can't eat with that on.' He points to your cock gag.

You crouch down to let him slip the gag bridle from your head.

'Airhead,' he says as he pulls the plastic cock from your lips. You open your mouth to stretch.

'And put some more lipstick on. You look a fucking state.'

Back in the dining room your make-up reapplied beautifully the lads wait patiently. As you approach the table your arse muscles relax and you feel your nappy dampen. Ugh! You squeeze your cheeks tightly in an attempt to keep what's left inside but the horse has bolted and your stretched arse seems incapable of holding on.

'Now gentleman shall we eat? ' James waves a hand beckoning you to climb under the table. 'Who's first? Guy do you want the pleasure?'

'Yeah,' he replies hungrily.

.

There's surprisingly more room than you think as you squat in front of Guy's legs but you've underestimated your skirts as they billow around you. You bend and struggle terrified you might rip your pretty skirts. The strain on you arse is too much and it slowly seeps more water into your nappy. Ugh! You grimace but strangely as you become accustomed to the sensation you find it rather pleasant and wit

no one looking you release your bowls and you feel like a naughty little girl hiding under the table. You settle back no longer worrying about the nappy. You know what's now required.

James knocks on the table. 'Hurry up Sissy from the look of Guy your foods getting cold. We don't want it to spoil do we?'

With trembling fingers you unzip his fly. His cock strains for release like a caged tiger waiting to spring free. Your heart skids from side to side inside you. You take a breath so deep you hiccup.

For Gods sake hurry, slut, hurry, I'm busting.' Guy shouts his mouth obviously full of food.

Nervously you pull out his cock and study its enormous girth before taking him in your mouth. As you do he grows bigger and bigger. Guy must have said something as you hear everyone laughing and gossiping loudly. Cheers from the table above and groans of pleasure from Guy fill the room. Then he shoots his load but as you relax to release him he reaches under the table with both hands and grabs the back of your head keeping you pressed into his groin. You smell his strong musky smell and taste his salty cum. You hold his knees for support and then to your surprise he starts peeing. You struggle but he won't let you go and before you know what's going on, you gulp and gulp to swallow it all. What else could you do? You didn't want to be pissed on or be responsible for ruining James plush carpet and you didn't want to smell like a toilet.

Eventually having dumped his load and emptying his bladder he pushes you away having served your purpose. You swallow hard and lick your lips. There's a loud rap on the table above.

'Next,' you hear James cry. You know what he means and you shuffle to Ian. Again you unzip his trousers but this time as you take hold of his cock you notice a drop of juice on its head. Hungrily you lick it off before putting his cock in your mouth. As you press his cock to your lips you know things are different.

You moan and purr as you take him deep in your mouth. You feel wonderful. You wiggle your tongue along his shaft and move your head back and forth along his shaft. For some variety you pop his cock out of your mouth and hold it tight against his stomach with your hand while you slid your tongue down his shaft to his balls, kissing and licking you're, fingers toying with the head of his cock. You stick your tongue out and lift his balls, bouncing them softly on your tongue, you suck each one in your mouth before letting your tongue slide up his shaft, licking one side then the other. You pop his cock back in your mouth. You start to suck him faster and faster. You hold onto his cock at the base, letting your fingers lightly jerk him as you suck his cock. Your eyes are still looking up at him, you can just make out his eyes were half shut. His breathing is faster. you feel him clutch your hair in his hand and clench it tight. His first shot hit the back of your throat. You cough a little as another shot with the same force, he pulls your head tight against his stomach, his cock buried deep you stretch your mouth as he unloads his cum in your mouth. You moan and gasp as he grounds his cock in your mouth. You swallow everything he gives you. You feel his grip on your head relax, you pull his cock out of your mouth, and lick the entire length, watching it respond to your wet tongue, He opens his eyes and smiles down at you. Then like the others begins to pee. You stuff his cock back in your mouth and swallow. As if its Christmas you gorge yourself on his piss. Mouthful after mouthful you gulp. Eventually the torrent subsides and he withdraws.

Another sharp rap on the table. 'Next,' cries James.

.

He straight away pushes all eight inches down your throat and spurts without warning.

'I've not cum in about three weeks.' he tells the friends justifying his premature ejaculation and too prove a point he continues to jet the biggest load of creamy thick cum you could ever imagine and soon he too was filling your mouth with hot pee.

'Sissy, you'll -'

Spill it? Got it in one. His cock sprays pee into your mouth with such force you lose grip of him. His cock slips out. You grab it but knock it so that it sprays your face and chest instead. Two big patches stain your dress. You panic. His cock is squirming like a fireman's hose. You catch his cock with your mouth and continue to drink hoping the lads didn't notice. But despite your best effort but can't swallow quick enough and eventually your pretty dress is ruined. James must have smelt the pee and sensed your predicament.

'Oh, for fucks sake! Don't spill your dinner and don't get any on my friend's clothes or they won't be pleased.'

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