Close Shave

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His legal sister makes him confess to being a sissy.
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Tomsparty
Tomsparty
647 Followers

My sister, Sharon caught me naked, shaving my legs in the family bathroom.

'I thought you where in Court all afternoon.' I cried dropping the razor in surprise.

My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required for the rest of the day.'

Sharon was a trainee barrister at the local county court and took her work seriously.

'Mum and dad still at work then?'

I nod nervously. Despite being in our early twenties we both still lived at home.

I tried to explain why I was shaving my legs silky smooth. All the top athletes do it. Guys at the gym do it. Even the young male A-list celebrities do it but she was unconvinced. Her bright attentive eyes dart all over my body seemingly missing nothing. She looked different, her skirt seemed particularly tight and her heels alarmingly high. Imposing... almost threatening.

'OK, OK, so you shave but why moisturise and ...' She whips the towel from around my waist. 'Do you really need to do your bikini line too?' She laughs and her eyes glisten unpleasantly. 'And hey! Isn't that my "Lady shave" and perfumed moisturiser?'

Her mobile phones tuneful ring shattered the silence that followed. I'd been saved by a distraction. She doesn't move but just stares transfixed at my long slender hairless legs.

'Aren't you going to answer that?' I ask.

She looks at the phone and her boyfriend, Sean's name and number flashes on the display. 'No, I'm through with him.' she says dismissively. I want to know more but I'm reminded of my predicament as she rocked back on her heels and let out a jail keepers hearty laugh. Caught fair and square I hoped she'd understand and show some remorse. Wishful thinking.

'I'm going to tell mum,' she says excitedly. 'I'll tell the girls at the bar, your mates at the pub and your so called colleagues at work.'

I cringe. 'Please don't,' I plead. 'Please don't.'

'Silence, silence in court,' she grins childlike and a shiver of terror runs down my spine. She was playing with me like a cat with a mouse.

'Yes...' she says slowly, 'I wonder what your city colleagues would think? Or do all the share traders shave and moisturise?' She laughs and shakes her head. 'I should feel sorry for you but with all that money and you still can't find happiness.'

I shake my head in shame. She looks at me thoughtfully and as if inspired by some great thought grabs me by the hand and leads me across the landing to her bedroom.

'If you want soft luscious legs, darling you obviously need to flaunt them too. So you'll need to protect them from the cold? Here try these.' I stare at her blankly. She hands me a pair of sheer stockings and my heart beats so hard I fear it might leap out of my chest. I finger the fabric enviously. I stroke the nylon like a cat, careful not to snag the ultra fine mesh. I linger far too long and she knows I'm caught like a fish on a hook. Quickly I hand them back and shake my head.

'Come, come, darling, those nicely moisturised legs need to feel the sheer beauty of luxurious nylon. Hurry, don't be shy you know you want to.'

I did. I really did, but not under duress so I shake my head and that's when her mood changed dramatically. 'You young man stand accused of pampering yourself to the point of confusing your gender. The court needs to know the truth. Are you a girlish sissy or a pretty boy to whom vanity has got the best of them? Now put the stockings on,' she scowls menacingly, 'and let the sensual nylon help us decide or I'll reach a sudden verdict and tell absolutely everyone about you, my big important city trader brother who is really a silky smooth sissy who wishes he was a girl.'

She emphasises the word "girl" and quite out of character I feel tears well up in the corner of my eyes. 'No you wouldn't, surely.'

'Wouldn't I,' she sneers, 'now stop delaying the inevitable, sit on my bed and roll these oh! so pretty stockings up your legs.'

Why did I? I still don't know. I should have refused. Just walk away? But know... Instead I meekly did as she directed the soft fluffy towel still around my waist.

She leans against the windowsill, legs slightly apart, and her skirt stretched taught across her thighs. She crosses her arms and looks down at me with her piercing blue eyes as I roll the first stocking in my hands. 'You may begin,' she says in a tone reminiscent of an exam moderator. I cross my legs, point a trembling toe and stretch the first stocking over my foot. My body tingles and under the towel my cock begins to throb. OK, yes I'm in heaven but I curse my urges, as unless I can temper my excitement I will expose my closet fantasy.

The stocking has an almost magical effect. I surrender to its embrace. My normal strength drained I felt like a deflated beach ball.

'That's it, darling now roll it up over those slender calves of yours. We must protect your delicate waif-like skin from the cold.'

My hands quiver as I feed the nylon out through my nimble fingers like a professional until its stretched over my knee and halfway up my thigh. I extend my knee outwards. From my ankle I run my hands up my leg straightening the nylon, ironing out any unwanted creases.

Sharon is impressed. 'Well done. Full marks. You've done this before. It obviously comes so natural to you.'

I shake my head.

'No you can't deny it. You're as guilty as sin. Exhibit A - previous experience. I've never seen slipping stockings on so gracefully done.'

'No,' I sop, 'it must be beginners luck.' but as I crossed the other leg ready to do the next stocking my towel rose showing my obvious pleasure.

'Oh! My goodness,' she cries, 'I rest my case. Exhibit B – Stiff excited cock.'

'No,' I sniff but even then I knew I had no defence with a cock as erect as a maypole.

'I don't understand,' I sob staring directly ahead, fighting back the tears. This isn't fair. I'm tense and you're putting me under incredible pressure.'

Sharon smirks. 'What you the city trader. Are you telling me you're not used to pressure? All those big corporate decisions, all that money changing hands. I don't believe you. Besides pressure or not you still have to put the other stocking on.'

'P, p, p, please.' I tremble but Sharon shows no remorse.

'No privileges for a first offender,' she sneers.

Accepting my fate I cautiously I repeat the process, hands quivering and soon I'm sitting knees together, head bowed on her bed.

'Come on darling show Sharon your pretty shaved legs,' she coos taking my hands, lifting me up to a standing position. Once erect she lets go and holding my towel pulls it off like a magician with a flick of her wrist.

My cock sticks outward proudly and I go to cover myself but she whips my hands away with a whip like "Laura Croft" crack of the towel. The room fell silent and Sharon gazed at my erect cock. She scratched her chin thoughtfully.

'Well, well, we have been keeping a secret hidden.' she giggles triumphantly, 'We can deal with that later, in the meantime every girl knows that you've got to hold your stockings up with suspenders.' She then majestically throws me a lacy suspender belt.

I catch it and wrap it round my waist. I clip it at the front and twist the fastening to my back. Sharon smirks with satisfaction as if receiving forensic evidence to confirm guilt but remains silent. Heart still pounding I carefully fasten each suspender strap to the lacy stocking tops.

'Can I go now,' I plead.

'No, certainly not, who said we've finished.' She flicks my throbbing cock with my towel again and drops a luxurious pair of panties on the floor in front of me.

'Pick them up,' she commands and as I do she appears to smile gleefully at my embarrassment. 'Hold on,' she barks. I crouch frozen to the spot her skimpy panties in my hand terrified to move as she rummages in her wardrobe again. 'These first,' she barks handing me a towering pair of slingback sandals. I gulp. I've never seen them before. One by one, panties still in hand, I bend demurely at the waist and slip them on each foot. They fit perfectly.

'Very good,' Sharon purrs, 'I always think a well-made pair of slingbacks enhance a pretty ankle. The shoes are so the foundation for beautiful legs.' As if on que I look down at my own legs that now looked shiny smooth, slender, incredibly long and very fetching. Secretly I was delighted. 'And now the panties.' Sharon barked.

I balance precariously in the slingbacks and step gingerly into her panties. Like the heels they fit like a glove. Even my cock seemed to wilt to allow them on. Cool as ice, soft as cashmere and as silky as satin. They drove me wild with excitement as I slid them up my legs under Sharon's watchful eye. After what seemed like minutes the cotton gusset touched my cock and I had to concentrate really hard to avoid bursting my load. And that according to her would be all the evidence the prosecution needed for a rock steady conviction.

I try another angle. 'I've not been feeling well,' I say unconvincingly. 'It's why I took the day off.'

'Nonsense,' Sharon said. 'You thought you had the house to yourself. You're dirty little mind thought you could spend hours pampering yourself like a girl then dress all sexy in my lingerie and dresses.'

'No, you're mad. I'm a realist. I'd look stupid.'

'Stupid.' She bellows, 'you know you wouldn't look stupid. You have an amazing figure. It's as I thought, your body is more suitable for women's clothes than men's. You must agree with me. The evidence is clear. Its an open and shut case.'

I look down at my feminised form and nod sorrowfully. 'I suppose you're right,' I said. I paused and looked at Sharon properly. 'You must think I'm stupid?'

'No, not stupid,' said Sharon. 'But you are a sissy and I should make you stay in my panties and stockings and tell everyone how you like to dress in lace and silks.'

I cringe with embarrassment and totter precariously in the slingbacks.

'Now,' she said clapping her hands, 'time is not a premium, where's that nice matching bra?'

'Please don't go on. This is all highly embarrassing.' I sob.

Sharon shakes her head. 'You should of thought of that before shaving your pins and using my stuff. Now silence in court while I finish building the prosecutions evidence. 'It's time to show me some more of your beginners luck.' Again she leans on the windowsill as I wrap the bra around my chest, clip it shut and like the suspender belt twist it to round my back. Next I feed my arms through the straps as Sharon satisfied with my performance pulls some cotton wool from her make-up draw.

'Stuff your cups,' she says with a smirk. 'I'll say when.'

I continue to totter awkwardly in her heels stuffing each cup with wool stretching the delicate lace cups to capacity. But to my surprise Sharon doesn't say "when".

I catch a glimpse of my reflection in her wardrobe mirror. I look like a skinny bird with big tits. My boobs look overtly large as if I've had plastic implants and my cock keen on the idea immediately springs back to attention. They didn't look quite right.

'When,' Sharon shouts but the damage has been done. I now have an amazing figure even though I'm rather top heavy sporting a massive pair of tits. I looked curvaceous and sexy. 'Well done.' Sharon said gathering a full slip in her hands. She holds it open for me to dip my head into.

If I thought the pretty panties where pleasurable the following sensation of creamy silk cascading down my torso almost made me cum and I stifled a groan.

'Almost there my dear. Hold on, keep it in we can't have you getting too excited before we finish can we?'

'Please stop,' I cry. 'What do you want me to do! What do you want me to say?'

'I want you to do and say nothing just relax and enjoy the experience.'

I wasn't so sure. I was convinced Sharon had a hidden agenda. She was enjoying the prosecution far too much.

Next came the dress. I'd seen her wear it many times before. It was a floaty chiffon dress in aubergine, with frilly three-quarter length sleeves and a plunging neckline. To top it all she gave me a scarf that matched my slingbacks. I looked incredibly fashionable. But that should come as no surprise, Sharon was a follower of fashion and even with her low salary managed to always look up to the minute.

'Look after this outfit its new.' She jotted some things down on a post-it-note. 'You are my size and... We could be mistaken as sisters. I'd never noticed before. You're remarkable.

She made me sit at her dressing table as she selected a colourful range of make-up. First she arched my brows and coated my face with foundation. Then with a ready canvas she applied mascara to my lashes, eyeliner to my eyes and shadow to my lids. She even accentuated my cheeks with some blusher and stuck on a set of brightly painted false nails. My hair was long, shoulder length and for years I wore it in a single ponytail. Sharon had never seen it undone and she took great delight in cutting the elastic band letting my well cared for locks cascade over my shoulders. She brushes it until it shone, applied a few clips to keep it from my eyes and sprayed it with some hair spray. Needless to say she was delighted. 'Exhibit C - Armed and dangerous. All tooled up.' She cried. 'You've been growing this for years so you can look pretty and feminine.'

Finally she coated my lips with a bright pink lipstick and as she made me dab them with a tissue my tortured cock could withhold its jewels no longer and erupted in a satisfying spurt. I groaned, I stiffened and it was plainly obvious what I had done.

'Good girl. Exhibit D - Sexual fluid. Forensics would love that.' To my amazement she then took a plastic bag from her briefcase and a fresh pair of panties from her draw. 'Take them off and give them to me.' I do as she directs. They're wet and heavily soiled with my excitement. She slips them in to a clear plastic evidence bag and seals them tightly. 'Now I almost have all the evidence I need.' She chuckles.

'Good,' I say with some relief. 'Can I dress back into my own clothes now, please?'

She shakes her head solemnly 'No I'm still collecting evidence for the prosecution. I don't want you getting off on a technicality. I want this case water tight.' She took a digital picture with her mobile phones camera. Then made me pose like a catalogue model head held high pouting. 'Exhibit E - Photographic evidence.'

Fully dressed and looking remarkably convincing Sharon walks around me prodding me with an outstretched finger. 'We are now going on a journey.' She says.

'No! That's it.' I cry. 'This stupid charade has gone on far enough. You're acting like some TV police show detective.'

Sharon laughs and ignores my comment. 'It's too late to run now. Your cover is blown. I've almost all the evidence I need. I just need the verdict of a jury.'

'What, you're mad.' I scream. 'Evidence, prosecution, jury what is your game?'

Sharon laughs. 'And you're in no position to negotiate. If you don't do exactly what I say I'll send an MMS of these photos to absolutely everyone we know.'

'Please,' I wail. 'When will you stop?'

'When we have a verdict.'

She led me downstairs to the front door. Fortunately the street was empty.

'No not outside.' I tremble, 'Not dressed like this.' I cast a hand down over my chiffon dress causing the material to float provocatively around my body.

She stares at my crestfallen face and dabs my lipstick with a tissue. 'You look stunning. Why are you worried? I really don't know. No one will recognise you... Unless of course you're terrified of the truth.' She takes a bottle of perfume from her handbag and sprays my neck and wrists. 'Don't be shy you look and now smell fantastic and remember look at those lovely, all important, shaved legs.' She lifted my dress and squirted my fresh panties with perfume.' Don't you smell lovely?

My face reddens yet my cock throbs with anticipation.

'I want to see how you act with ordinary members of the public. Do they look through this feminine dress and see a masculine city trader or as I suspect see nothing more than a pathetic sissy who wants to be a girl.' She giggles girlishly. 'If my hunch is correct you'll pass as a pretty young lady in the street.'

I had a dilemma - behave as masculine as I could. But be humiliated and ridiculed in the street but avoid being branded as a sissy. Alternatively act how I felt. Live the dream. Move and behave just like a woman. I would escape public ridicule but according to my legal sister strengthen the case against me. I was trapped. I felt like a seventeenth century witch being tried for witchcraft. Dunk her in the village pond. If she drowns she's innocent. If she survives she's guilty. I just couldn't win. I had to think fast.

'We will go in yours.' she says picking up my car keys from the hall table.

She always loved my car but I groan aware that my bright red Porsche convertible is rather more conspicuous than her tiny Mini.

Once outside the fresh air assaults my legs and blows through my wafer thin dress. It's so light I feel naked. I shimmy across the drive my dress rustling with the breeze, my hips swaying, my heels clicking, my stockings rasping alluringly. Unaware of my thinking Sharon opens the passenger door and gestures me to sit. The dress is short and floaty so to her delight I back into the car, lower my rump onto the seat then delicately swing my legs together into the seat well. As she shuts the door I hear her mutter "hook line and sinker".

We drive into town in silence. The roof down so the wind blows in our hair and everyone could see us. I try to shrink into my seat but Sharon isn't having any of it as we pull up to a set of traffic lights. 'Sit up, back straight, eyes out front, knees together, hands in your lap.'

This was already well but I hardly had a lap. The skirt was so short I had to tug the lacy hem to retain any form of modesty. She sensed my nervousness and took her hand off the wheel and onto my knee. She squeezed my thigh and let her fingers wander up my stockings. I momentarily closed my eyes and imagined that I was Sharon and Sharon had changed places with Sean. I wondered what they had got up to together. My cock trembled with excitement and I began to worry if my pleasure would notice under the chiffon folds of my dress. 'Don't worry darling you look ...' We were interrupted by a loud honk from a lorries horn as the driver on the left carriageway looked down from his cab with a lecherous smile. I blush and tug my hem downwards and flick her hand off my knee but Sharon is delighted. 'Exhibit F – An accomplice,' she mutters. 'Do you know him?' She laughs and it was indeed fortuitous as the lights changed green and Sharon sped off.

After a while I got accustomed to the openness of the dress and the lightness of the material. It was a great feeling and as Sharon drove the powerful car I imagined how it must feel being driven on a date by a handsome man. I felt beautiful, special and pampered. But my dream is spoilt by my evil, twisted sister who seemed determined to ridicule me and stage a weird courtroom drama with me as the accused.

Sharon drove into the high street car park, found a space and applied the handbrake.

'Now,' she smirked. 'Let the jury decide.'

I bowed my head and looked at my long painted nails in my lap and squeezed my knees together. Fear and interpretation etched on my face

'I want you to find your own way home by bus.'

My jaw dropped like a tailgate of a truck yet somehow I anticipated more.

She handed me a tiny clutch bag some coins jingling inside. 'There's just enough money for a bus trip home. Let's see how you cope with being on your own. Can you carry off this charade? Guilty or innocent? Let the public decide.' She flicks her hair off her face proudly. 'And then when you're back home I'll give you, as judge, my final verdict. Sissy or simply vain.'

Tomsparty
Tomsparty
647 Followers
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