It's For CharitybyTomsparty©
You gaze dreamily at the little black dress in the charity shop window. It's Christmas, it's party season and you'd do anything to wear the delicate feminine dress. You shrug your shoulders and gaze further into the shop. The company Christmas party is tomorrow and you've no idea what to wear or who to take. You stare once more at the dress in the window and imagine it hanging gracefully off your shoulders as you step demurely onto the dance floor. Your tiny cock carefully concealed in beautiful lacy panties, your padded breasts pert and proud swinging within your matching bra gives you an enviable figure. The parties in full swing as your pointed heels click and shear stockings rasp as you sway to the music, held tight at the waist by a handsome young man. He expertly spins you around and your new floaty little black dress (the one in the window) spirals outwards flashing a glimpse of lacy stocking top and pantie to your many onlookers. You blush and look around and see your girlfriends stare at you enviously as you dance like a pro, look like a fairytale princess and drape from the arm of the most handsome man in the company.
Your dream is shattered as you hear your name called from across the street. You recognise the sultry, sexy tones of Jill from the office. You turn as she skips up and stands beside you. Your heart melts. Jill is the most beautiful girl you know. With an hourglass figure, long slender legs, firm pouting breasts and shoulder length blonde hair she had many admirers.
'It's simply gorgeous,' she sighs squinting at the dress you where admiring. 'Isn't it amazing what people discard these days? It must be an incredibly expensive chiffon.'
You stare with glazed eyes at the lace frill hem, the many sequins and the delicate embroidery round the bodice. It looked so light you wondered if you'd ever know it was on.
'Why don't you come in?' she beckons opening the door, 'you never know what's inside.'
Like a young lamb you follow her meekly inside the shop. She knows you'd do anything she asks, you are her obedient puppy, her dopey eyed deer.
Jill could have anyone. It caused you acute pain to know that someone else was special to her and not you. That someone was a guy from the office, Liam. A guy you despised, as he was everything you weren't. He was tall and muscular with broad shoulders and a chiselled jaw. He had been Mr Right and she had chosen his bed.
You close your eyes against her naked image but her soft sensual skin is against him, not you and you couldn't let the image go away – it was so frustrating! You open your eyes and stop by the window display and stare transfixed at the black chiffon party dress yet again. Standing so close you feel a magnetic pull and can't resist touching the soft delicate fabric. You tease the sparkling material between two fingers and your tiny cock begins to tremble. How you wish you could go to a party this Christmas in such a beautiful dress.
'Dreamer, dreamer,' Jill cry's. 'Look here, darling.'
You turn somewhat sadly and follow her deeper into the shop where she's examining a shiny black pair of stilettos. With heels so high you could hardly imagine anyone walking in them. Jill giggles. 'What do you think? Sexy or what?'
You nod with approval as your cock begins to throb as you imagine her teetering around in nothing but the towering heels..
'I call these "fuck me" heels.' She giggles and runs her tiny fingers down the huge heel in a provocative manner. 'Any girl brave enough to wear these wants just one thing....' She giggles again and looks at you with her large blue saucer like eyes and you feel your face blush. 'I've simply got to buy them.'
You're slightly bemused in that she doesn't try them on.
At the cash desk Jill's mortified to find that she's left her purse at home. You lend her the money and the lady wraps them with as much care as if they where new. 'I came to buy a special present but without my money I may as well go home.' She looks at you with kitten eyes and flutters her long lashes - you can't resist.
'I'll lend you the money,' you say delighted to be out shopping with the girl of your dreams.
'Thank you darling,' she says as she picks up the wrapped heels in one hand and loops the other arm round yours and marches out of the shop.
The special present turned out to be the most gorgeous sexy chemise you'd ever seen and by your standards it cost a small fortune.
'Quality comes at a price,' she grins. 'Anyone could look amazing in this. Look...' she paused and looks you deeply in the eyes, 'if you've done shopping why don't you come back to my flat? I'll fix us a warming glass of mulled wine... and if you play your cards right I may show you what these things look like on.'
Hey your mind spirals off into overdrive as you imagine Jill yet again wearing the 'fuck me' heels but this time she's dressed in the sexy chemise and beckoning you on. You shake your head in disbelief... this can't be happening.
'Er... don't you live with Liam?' you ask cautiously.
'Yes,' she says dismissively, 'but we're through. Things haven't been going well lately. He's been away a lot recently in the Warwick office and since he's been home, well things have just changed between us. I suppose it was bound to happen with him working away so much and everything.'
You lean across and touch her arm tenderly. 'I'm sorry.' You lie as you try to suppress an evil grin.
'It's OK,' she says drawing a deep breath. 'It could be worse. We could have children.'
You look at her sympathetically, must have seen the question in your eyes, but couldn't bring herself to hold the gaze while she answered. 'No, its nothing like that - I haven't met anyone else. I just don't love him anymore.'
As she said the words that you could only dream of you realise two things: first Liam is a prat to let her go, and second, that she was giving you a very subtle come on.
There's an awkward silence then Jill says. 'It just run its course, that's all. I think it fizzled out but we haven't both admitted it yet.'
'What! You haven't told him yet?' you say.
Jill smirks awkwardly. 'No. I haven't found the time. Things just haven't been right. He will be so upset. I explained the situation in his Christmas card, as I can't face telling him the truth. But...,' she chuckles 'I'll wait until after Christmas so I can get a big expensive present. He's always so imaginative with gifts and incredibly generous. We constantly strive to outwit each other'
You're apprehensive you don't like Liam he's a big guy, the office bully. He throws his weight around like a teenager. The sort of guy whose girl you don't mess with but this was great news and through Liam is very different from him you oddly thought you stood a chance.
Amazed with your fortune you practically run her home and she's true to her word. After fixing you both a intoxicating mulled wine she disappears upstairs only to reappear wearing the sexy chemise, the high heels and little else. You find yourself drooling like a hound as she parades up and down like a catwalk model swinging her hips and arms. Her tiny black panties, stockings and suspenders clearly visible under the sumptuous slip. Once or twice she passes by you so close you can smell her perfume and feel the wind from her hair as she tosses her mane at you seductively. But as you reach out to touch the forbidden fruit she smiles and walks away. There's no mistaking she's a tease and you're disappointed that though she's wearing her so called "fuck me" heels she doesn't offer.
'This is what I love about Christmas.' She says twirling round the room dreamily. 'The roaring fire, the scent of pine and cinnamon and fairy lights on the tree. Wearing these sexy things while I drape myself over a sheepskin rug.' She shivers. 'Look I've gone all goosey.' She stops the show in front of you and runs her hands up and down her body knowing full well the effect it was having on you. 'You know?' she says, 'I'd love to see how good you look in this pretty slip.'
You laugh but she wasn't joking as she brazenly slips the spaghetti straps off her milky white shoulders. It falls gracefully to the floor and her pert breasts almost shoot you in the eye. You gaze open mouthed at her erect nipples as before you can object she's undone your shirt buttons and is tugging at your sleeves.
'What could you say? You look at this beautiful semi-naked girl in front of you, and a montage of thoughts pass through your mind. Her long legs wrapped around your waist, her soft lips on yours, your cock deep inside of her, the incredible delight of finding a beautiful woman who wanted to dress you in her lingerie. You fold your arms in a hug that lasted for ages. When you broke apart, wet eyed, you realised that you where endangering your job and confessing your secret longing. No one knew that you longed to cross dress and you didn't want to admit it in front of the girl of your dreams as you didn't feel it was contusive to a long-term relationship. The risk was just too great. 'No,' you say. 'It's not right.'
'But, sweetheart, baby, you'll look so sexy, you'll-'
'No, Jill. What will you ever think of me?'
'Don't be so silly darling. I find a man in my sexy lingerie incredibly sexy. There's no telling what will happen if I see you in this.' She flashes her formidable blue eyes again and flutters her eyelashes as you begin to slowly melt to her charms. 'I won't tell anyone. It will be our little secret.' She says sweetly.
She wants you to dress in her clothes. Oh, my God. You could not grasp the concept. Two minute ago Jill had been your ideal girlfriend. Now she was suggesting you do what you dream of doing. Wearing her clothes. It was too big for your head to hold. But why are you so shocked? You've dreamt of having a girlfriend who would dress you in dresses and skirts, make-up your face and buy you sexy shoes. You shiver with apprehension and Jill detects some reluctance.
'Come on, darling wear these just for me.'
'No, No I'm fine really.' You mumble.
She came up close, looked at you hard. 'You're not, though are you? You're not fine' She put a hand on yours. This felt better and the enormity of what she asked seemed to shrink. You can talk to Jill. You want to talk to her. To tell her your dreams to open up to your desires but you couldn't trust yourself.
You nod cautiously. 'Ok Jill, but promise me you won't tell a soul. Promise. Please? Jill? Please.'
'Ok, baby.' Jill rocked you gently. 'You'll be my pretty girl,' Jill said tucking a rogue curl from your face. 'Follow me.' She steps quickly upstairs and you follow closely behind admiring her perfect bottom and rounded hips.
Once inside her bedroom you nervously take the pink lace chemise from her and step a quivering foot into its neck. Woah! You immediately feel ultra pretty, ultra sexy and ultra spoilt. It must be the most decadent piece of lingerie ever. It hung from your shoulders just like on Jill and cascaded out over your hips in ripples of delicate lace - it was magical.
'Just don't put it in the wash machine.' Jill jokes as you study yourself in the mirror. It fitted perfectly.
'You can't get the full effect in those jeans, darling, take them off for me. I want to see your long slender legs and sexy butt.'
You do rather excitedly as she dons a semi-transparent pink dressing gown. Your smooth hairless legs seem to stretch forever and your ankles look shapely and cute. You slip off your socks without being asked. 'Good girl' she says as she unclips her stockings and rolls them carefully down her long model like legs.
You stare, your eyes on stalks, your cock fit to bust.
'Slip these on too,' she says calmly handing you her sheer black stockings and suspenders.
You gasp as you feel the sheer nylon between your fingers.
'Your legs are so soft and smooth do you moisturise?'
You pretend not to hear. You've never worn stockings and ask Jill for help to clasp the lace tops to the suspender belt she has clipped round your waist. Then to your amazement she turns her back to you and slips off her black minuscule panties. It's like slow motion; the turn, the bend, the sight of her naked buttocks through the semi-transparent pink dressing gown. She tosses them to you. They're still warm and as you slip them on you feel dizzy and light headed.
'How do I look?' you ask.
'Theres a question, How do you want to look?' she asks.
You think for a moment. 'Pretty,' you say.
Jill smiles. 'Is that what you really want?'
'Well darling, you look amazing absolutely stunning. You're a natural. You must have worn stockings before.' You lie and shake your head. She hastily drew a line of lipstick on your upper lip and you rolled them together in concentration. Jill watched with mild amusement and was about to comment when her mobile phone rings. She smiles at you and skips off to answer it in private. While she's gone you prance up and down her bedroom, tottering precariously in her heels. You feel amazing. So feminine, so young, so pretty.
'Got to go,' she says cheerfully reappearing but you're devastated. Disappointment must have shown on your face.
'I'm sorry my darling. All this excitement and I completely forgot the time, I've a prior appointment. Fear not, I can see how much you're enjoying yourself, don't take my things off,' she smirks. 'If you like them so much put your clothes on over my lingerie and take these pretty things home. I can pick them up later. I guess they are theoretically yours. You paid for them.' She chuckles devilishly. 'I'm so hot! The thought of you walking home in my lingerie is such a turn on and who knows if I finish early I may be able to pop in at your place.'
Wow! You smile delighted that you can keep her panties on a little longer and the thought of Jill coming back to your flat is enough to send your heart racing. You hadn't had an opportunity to invite her to the company party but you tell yourself not to be impatient – everything comes to those who wait.
She packed the shoes back in the box as you put your jeans and shirt on over her stunning lingerie.
'Take these heels with you too.' I don't want Liam finding them. He'll want sex and I'm just not interested.' You smile triumphantly as she stuffs the box into a larger carrier and seals the opening.
'Oh and be a love take his Christmas card, the one I told you about. Perhaps you can post it on your way home? I'm sending it to his precious Warwick office since he spends more time there than here. I know it's heartless but I've got to do it.'
You're delighted to aid their demise and carefully shove the envelope in your back pocket.
'Walk through the park on your way home. Past the old oak and you'll save a good twenty minutes.'
You thank her, she kisses you on the cheek and you set about walking home.
It was warm for a December and you floated along high on girlish dreams as the lace and nylon caressed your whole body like a thousand silken-gloved hands. As you reach the old oak in the park you get an unwanted surprise. Leaning against the tree is Liam with three other guys from the office, Glen, Craig and Dan. Liam looked horribly sure of himself, and when he spoke his voice was big and confident.
'Hello squirt,' he said, his dark eyes flashing gleefully. 'This is an unexpected pleasure!' Liam sneered as if expecting you. 'Been shopping. What have you bought me... Something nice for Christmas?'
Your heart sinks. He's the last person you want to meet wearing his girlfriend's panties. 'N... N... Nothing.' you stutter, 'please leave me alone, I'm in a hurry'.
Liam ignores your plea and instead looks at you closely.
'You wearing lipstick?'
'N, N, No,' you shake your head but remember the lipstick Jill smeared onto your lips an hour ago.
I thought you where away in Warwick.' you say in an attempt to divert his attention.
'Stop changing the subject' he shouts, 'I ask the questions. Besides I was, I'm back for the weekend. What's it to you.'
Glens pushes forward and stares at your lips. 'You are.' Glen shouts, 'Liam's right. You are wearing lipstick!'
They all laugh like crazed hyenas and you blush with humiliation.
'What you been buying sissy?' Liam grabs your bag that contained the shoebox.
'They're a present.' you sniff.
Liam tears open the bag and to your surprise a pair of metal handcuffs, a shoulder length blonde wig and a frightening dildo and a cock gag fall onto the grass. 'Oh look here.' Liam cry's with delight. 'Santa's fairy has been busy.'
You are flabbergasted. 'I don't know where they come from,' you bawl in surprise.
Liam opens the box and tips out the "fuck me shoes". 'Yeah right. The same place as the lipstick no doubt,' He sneers. 'You have a hidden personal life. Who would have believed it?'
'No, you've got it all wrong and do be careful' you cry, 'you'll mark them.'
The lads all laugh. 'Oh do be careful! ' They repeat in pompous voices mockingly. The boys all titter as Liam picks up one of the shoes and fingers it lovingly centimetres from your face. He stares agog at the towering heel. 'These are beautiful sexy shoes' he mocks, 'who do you know who's slutty enough who will wear these?' He remembers the lipstick. 'Or are they for you pretty boy.' He smirks and claps Glen on the shoulder. My girl friend calls shoes like this "fuck me" heels. Who are you out to impress? Who do you want to fuck?' Or do you want to be fucked?' The lads all laugh and walk around you as if crazed wolves closing in for the kill.
You remain silent and Craig twists your arm behind your back until you wince with pain.
'Stop it you're hurting me,' you cry.
'Tell me?' he asks menacingly. 'Who are these for? We can make this easy or difficult.' Again Craig twists your arm but this time you can't help but scream out Jill's name.
All the lads stand stock still, shocked. 'What you mean? Liam asks. Jill who?' Again Craig twists your arm. 'Your Jill,' you scream. And as you tell him you know you're in trouble.
'What! you're doing buying my Jill expensive Christmas gifts,' he roars punching you in the stomach. Sexy Christmas gifts. Gifts that I could never afford.' He looks at the tree and turns angrily to Dan. 'Get the cuffs,' and before you know it Liam slaps a cuff round a wrist and yanks your arm upwards with such force you feel your arm pull from its socket. Your eyes water and as he held your hand high Glen grabs your other wrist and pulls that upwards too. Dan fumbles above you and you try and look upwards. Its then you hear a terrifying click and feel the other cuff snap tightly round your free wrist. The two lads release you and step backwards proudly. You're trapped suspended by your arms like a Christmas turkey in a butchers shop. You hang stupidly, your arms held upright the cuffs over the tree branch. You struggle but all you succeed is causing the cuffs to bite into your skin. 'Help! Help! Let me go,' you scream.
'Shut the fuck up. Silence!' Shouts Liam who is getting increasingly agitated.
Things go from bad to worse as you feel the slip twist and caress your skin. On tiptoes your shirt untucks and rides up causing the silky lace slip to peek from under your shirt. It doesn't go unnoticed.
'What you wearing' Liam shouts. You're terrified as Liam grips your shirttails and pulls them apart causing the buttons to pop off in a spectacular fashion.
'Hey!' you scream and kick outwards but you dangle helplessly. Liam is still holding your shirt open as he stares open mouthed at the beautiful feminine chemise.
'Look at this lads,' he roars and Dan, Glen and Craig all gather in front of you to see. With an audience Liam rips off your shirt completely.
'Oh my God!' he gasps, 'you fucking sissy. I always had my doubts about you gay boy'