Close Shave

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Tomsparty
Tomsparty
647 Followers

If only it was that simple beside I didn't believe her. I knew I was guilty. I loved wearing her dress and lingerie. I'd wear them everyday if I could. I had to think fast and cut a deal.

'If you please, Sharon,' I said, my voice little more than a whisper, 'I think I have a better idea.'

Sharon glowered at me. She didn't like her plans questioned and I wasn't in a strong position to bargain with her.

'Well not better, as such.' I said, backtracking. 'But an alternative that you might like to consider.'

'Go on,' said Sharon checking her own make-up in the rear-view mirror

'You want a bigger wardrobe, yes?'

She nods and rubs her hands together thoughtfully. 'Full of the current fashions and top designer labels. And you said so yourself we have a similar figure. Well this could work to your advantage.

'I'll play your game and plead guilty.'

Guilty she interjects.'

'Yes guilty. I like wearing ladies clothes. I'm, if you must pigeon hole me a sissy.'

A smile spreads across her face. 'I knew it,' she said gleefully. 'Can I tape a confession?' From out of nowhere she thrusts a pocket tape recorder under my nose. 'This is Sharon, the time is 2.45pm and I'm interviewing my brother over the ledged sissy incidence.' She suddenly looks serious. 'Lets cut to the chase. Do you like wearing dresses? Are you a sissy?'

I heard the words come out my mouth - words I'd always longed to say, but never dared to imagine that I ever would. 'Y, Y, Yes.'

'Excellent Exhibit G - a taped confession. '

'N, N, No,' I stammer.

'To late ... now what where you telling me?'

I clear my throat and try to regain my composure. 'Why don't we pool our resources. You help me and I'll help you. Your fashion know how, support and guidance with my money. Would you mind sharing the odd item of clothing?

I smile as sweetly as I can and flutter my eyelids provocatively.

'But -' Sharon began.

'As I see it, the choice is this,' I went on hurriedly. My humiliation and no gain or cooperation and a bigger wardrobe'

Sharon raised an eyebrow. 'So, sweet brother you're not such a dizzy blonde after all.

I lowered my head modestly

I see,' said Sharon. She thoughtfully tapped her fingers on the steering wheel.

The proposal was interesting, very interesting. For so long now she had dreamed of having an extensive wardrobe yet her meagre trainee barristers salary was barely enough to keep her clothed at work and I did earn an extortionate amount of money. Check mate I mused.

'Very well,' she said. 'But I still want some fun. I want you to purchase me a pretty pair of panties... and a matching bra and sheer stockings.' She gave me the post-it-note she'd written on earlier. 'I've made it easy for you and noted your or should I say our sizes. I need some new underwear so why not.'

'OK,' I say.

But then she has a rethink. 'Hold on. I've made it far too easy for you now.' she scratches her chin thoughtfully. 'I therefore want you to really impress me. I would like you to buy me a complete outfit. Something special. Something you could wear as a top secretary or PA in the city. You should know all about that. What does your stuck-up secretary wear? Remember I don't want some cheap chain store crap either. Find me something designer, something chic but do remember I must be able to wear it in court too so it can't be too sexy but on the other hand not too drab,' she giggles, 'I'm sure you'll cope. And if you're your choice please me I'll agree to your idea and I won't tell anyone about your kinky sexual fantasies it will be a deferred sentence.'

'Thank you, thank you,' I said emotion sounding in my voice. You won't regret your decision, Sharon, I give you my word.'

'I hope not, sissy,' came the icy response. 'Indeed, I will go along with your idea but should you let me down, then it shall be you who will live to regret my decision.'

With Sharon's doom laden words echoing round my head, I open the car door and swing my legs out demurely.

'You'll find your credit card in the clutch bag. And if I'm really pleased with your choice you could become my personal shopper.' she giggles. 'I've always fancied one of them. Be careful with the dress you're wearing too. It cost me a fortune and I don't want it ruined. Mess that up and there's no way I'm sharing anything... And...' she paused unsure as if she should proceed. 'I think you should buy us our own apartment. We are both far to old to be living at home with mum and dad. I don't know why we haven't thought of it before.'

'You couldn't afford it.' I say rather smugly.

'Precisely,' she says with an irritated tone, 'but you can. Just imagine in our flat you could wear what ever you want. I can see you now in some of my tiny skirts and sexy long dresses. So while you're in town pop into an estate agents and get a few details on properties in the area. Now hurry up. You must get back before mum and dad return from work or ... Well I needn't go into how difficult you'll find explaining why your wearing my chiffon dress and sexy lingerie.'

I shut the car door and turn towards the high street. I hear the electrical whirl of her window drawing down behind me. 'Remember no funny stuff. Don't forget I have the all the evidence.'

'Evidence,' I say.

'Yes hard evidence including photos, a taped confession and your soiled panties.'

I blush and hope no one has overheard. I turn and walk towards the shops...

How do I get on shopping? What do I buy? What is Sharon's final verdict? Do I make it home in time? Do I buy an apartment and live a double life with my twisted sister? What happens to Sharon's man, Sean? You decide?

Tomsparty
Tomsparty
647 Followers
12
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13 Comments
jennifurzoejennifurzoeabout 4 years ago
Oh the choices of exciting humility to begin..,

Shopping ends with more than one can carry,She gets appointments to look at a few places,however she's delayed on getting back and thinks should my parents get a surprisingly shocked new life for their once son or call pleading & begging evil sister for help...,

cdCindy1cdCindy1about 7 years ago
please continue

I can't wait to read the next chapters. I too am a sissy CD with a step-sister who caught me and now helps me with my cross-dressing and especially my make-up. She's my Mistress and I love it when she fucks me deep and hard. Please tell us what happens next in your story.

AnonymousAnonymousover 7 years ago
Wishing for a sister

Great story

Tootight1Tootight1almost 10 years ago
couldnt read

i got irritated by the 3rd or 4th paragraph, and couldn't go on. I've been dressing, for a long time, since very young, and even as tight as my family is, my sister would never do what his sister had done by the 3rd or fourth paragraph. had she done that (give no privacy, stood and stared, removed his towel threatened to expose) her face would have been lodged in the door frame, repeatedly, striped, photographed, hog tied, and abused. what kind of 20 year old mentality is this in a family that's been together for that long? no respect,,, id teach her respect, quickly.

GrrrreatImaginationGrrrreatImaginationalmost 10 years ago
Now wait one minute!

I've just read, and commented upon, two random stories of yours, both of which were exciting little reads with a teaser at the end (this one, and In Need of Counselling). You've done it again.

Mind you, that's both good and bad. You've written a pretty little story here with lots of sexy potential (that's the good part), and then gone off and never finished it out (right, the bad part)! And you can't beg off saying you never had any ideas to follow it up, because you tease us with good ideas in the final paragraph (of both stories). Finally, you can't say that you didn't get good feedback. Just look at the rating of this story (both of them).

Talk about a tease? And it's been years now. Come on and give us a little bit more of these tales.

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