Good or Bad Ch. 01

Story Info
Kinky cross-dressing game gets out of hand.
3k words
4.31
280.7k
35

Part 1 of the 2 part series

Updated 10/17/2022
Created 08/01/2004
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Tomsparty
Tomsparty
645 Followers

Chapter 1 – Ready to Play?

It starts innocently enough - your young wife sits beside you, wearing a stunning a-line dress, her long legs curled under her. As normal at this time of night she's painting her beautifully manicured nails a luscious colour. Tonight it's plum. Yet this time she has a huge grin on her face. You pretend to read as she strokes the varnish expertly on every nail - you love the smell, you love your wife and the sign of femininity that the varnish represents.

She notices your fascination.

'If you've been a good girl, darling I'll paint your fingernails too, hmm?'

Your steadily stiffening cock springs to attention. You laugh dismissively but find yourself muttering 'Yes... I've been a good girl.'

She smirks knowingly. 'Oh! I'm not so sure,' she says applying a final coat to her little fingernail. 'Good or bad, that's my ultimate decision?'

You grin, familiar with her sexy games. But when she asks you to stand and unbutton your shirt even you're surprised. She watches intently as you strip, waving her fingers for the polish to dry. Soon she's up and her fingers are wrestling with your belt. She seems to be gagging for it and you don't complain when your trousers are lying crumpled on the floor and you're dressed in only your briefs.

'Oh! Darling, your skin is so soft and smooth, your legs are so long and slender.' she rubs her hands over your body and you want to ravage her but she keeps you at bay.

'Your midriff is so taut and firm but not in a manly six-pack way. Your arse is so squidgy. Oh! You're getting better,' she says as you kick-off your shoes and pull off your socks, 'You've the making of a good girl.'

You smirk to yourself knowing sex will soon follow but to your dismay as you massage your rock hard cock she skips out of the room on the pretence of getting a new nail polish.

You needn't worry, or should you? She's soon back brandishing a bright pink bottle of nail varnish in one hand while the other hand is behind her concealing something. She grins like a schoolgirl and drops a small plastic carrier bag on the sofa.

'I've always thought pink more your colour.'

You don't have time to comment as to your surprise like a flash she delves into the bag pulls out a bra and guides your slim arms into it.

You open your mouth to object but she's already slipping the spaghetti straps over your shoulder, spinning you round to fasten the clasp behind you.

'But, but...' you stammer, 'hold on.'

But she's a woman with a mission and she's not listening to you.

'Oh darling, I know you like nail varnish and I've never painted your nails before but... I've always wanted to dress you in my lingerie.' She smiles warmly and a bright flash of her white teeth seems to make everything ok. You relax slightly and feel more comfortable. But hold on... this isn't her bra. For a start it fit's like a glove and you've never seen her wear such a sexy bra adorned with ribbon and lace before.

'I bought this ages ago,' she chuckles, 'waiting for this moment.'

'My goodness,' you say your heart beginning to pound furiously. Something strange is happening to me here. I don't like this. I don't like this one tiny bit...'

Just then, as you look at your feminised chest in the mirror, there came a roar of laughter so mighty the ground trembled.

'Stop it,' you cry but she can't stop and she continues to laugh as she stuffs your cups to an impressive DD.

But you don't complain. You like the attention and your body tingles with anticipation. How far will she go? What has she planned? You soon find out as she drops a soft silky slip over your head. Again it's larger than hers, fitting you perfectly and it cascades over your body like single cream poured over strawberries down your shoulders and breasts. It hangs beautifully coming to a halt, swinging like a pendulum just above your knees.

'Love the lace trim,' you say sarcastically. 'It's really fetching.'

You blush.

'Oh darling!' she says in an amazing voice. Sort of dark and dirty. She calls your name making it sound like soft porn. 'You do look so pretty. I knew you would - this is quality merchandise.'

You snort dismissively but strangely your heart starts to pound and you feel faint. You can't get any words out of your mouth.

'Dresses and skirts are so you, darling, and this saucy slip is a perfect introduction; its short, feminine and easy to slip out of.' She giggles like a schoolgirl her hands griping your bum as if fearful to let go. She gives it a squeeze then drops to her knees sliding her hands down your smooth thighs. Your quiver uncontrollably but as she reaches your knee she springs back up like a yo-yo but this time her hands slid smoothly up under your slip. You gasp and smile to yourself as she does the things that you normally do to her.

'Mmm!' you groan as her inquisitive hands explore your cock that's so hard it threatens to burst through your briefs.

'Wonderful, wonderful,' she says in that blue-velvet voice. 'Mmm! You are good' She hooks a delicate, finely manicured fingernail under the elastic of your briefs and yanks them downwards. You panic momentarily and feel as if your brain has turned to champagne bubbles. She lets them fall to the ground and you step eagerly out. You're ready for sex but as you grab her to pull her close she pushes you away.

'No, no, no, darling we're not done yet.' She dwells back into the bag and holds out a tiny pair of snowy white panties staring you in the eye. The panties are incredibly sexy with lace scalloping, satin ribbons and peek-a-boo froufrou. You stare at them open mouthed but know what's expected.

'Come on darling lets get these on your sexy butt. She stretches them open invitingly. 'Don't disappoint me?'

At this point you could object, yes you could refuse but like a thirsty horse led to water you step in to them wantonly. You hold your breath as you balance yourself using her shoulders and lift each leg slowly into the panties. You're awash with a strange series of emotions. It's a first - you don't know what to expect but with the bra and slip already on, wearing the pretty panties seem the most natural thing to do. They're deliciously cool and silky and as she slides them up your legs your little cock spasms enthusiastically. You try to hide your growing pleasure but it's futile. She pulls the skimpy material over your shapely hips and allows them to encase your cock tightly. But they feel so strange. Rather than cradle your assets like your normal briefs they cling on like lichen to a boulder.

'Mmm!' you gasp and as a finale she hoikes them a little higher than required then she drops your slip back down. As the silk cascades over your legs you lose control and whoosh! You eject your hot, creamy load into your new pretty white panties. 'Oh! Hmm! sorry.' You gasp filling your gusset and giggle girlishly.

Nothing escapes your wife.

'Oh! Darling you are now a naughty girl. Dressing in these pretty girly things is obviously turning you on far more than you've led me to believe and I'm not sure what to think.' She smiles with delight but you're embarrassed. What man wouldn't? It's one thing to dress in women's clothes as harmless kinky fun but its a total different ball game to get so much obvious pleasure.

She looks at you thoughtfully as if studying a painting in an art gallery. 'You force me to make a difficult choice - Do I like a man who looks good in dresses or do I prefer an attractive hunk. Hmm! Let me see.' She cocks her head to one side and puts a finger to her lips as if in deep thought.

You're speechless. But as you stand bare footed the silky slip swirling around you like a dress a warm strangle sensation judders through you. What is this drug like feeling? Why do you feel so different? How can a few items of clothes change your whole persona? You want to be soothed, you want to be complemented, seduced, covered with kisses, handled gently, wrapped in her arms, carried up stairs to bed and then the inevitable. Cripes - What's happening to you? You feel your testosterone drawn from you as if giving a syringed blood sample yet rather than be repulsed you feel deliriously happy.

What follows next is equally thrilling as from the little bag she pulls a pair of cream silk stockings, a lacy suspender belt and cream, patent leather, high heeled shoes. You'd never seen shoes with such skyscraper heels – and more alarmingly you want to put them on. Your heart beats faster and your head begins to whirl as if intoxicated with alcohol. You stand completely bewildered. There's so much to take in.

'Come on darling!' she shouts impatiently. 'You're doing so well lets dress those pretty legs? They deserve some attention.'

Soon the sheer stockings are beautifully smooth and straight on your legs, the suspender belt tight and secure around your tiny waist and its minuscule clips pull on your lacy stocking tops. She even fed the delicate suspender straps under your panties just like a girls. You begin to panic. She seems to be taking this very seriously. It all seems so intense way beyond your normal kinky games.

'I'm not wearing them,' you say pointing to the shoes she holds in her hand.

'Oh! Darling, Not wear these pretty shoes?' she says. She takes your arm in disbelief. 'Notice how the towering heels have been made to accentuate your shapely ankles, lengthen your whole leg - and how the soft leather has been crafted to cradle your foot and attract admiring glances wherever you may step.' She took a shoe, chuckles and offered it towards your foot. 'Both in its workmanship and design,' she announced, 'they're a triumph!'

'They're girl's shoes,' you say flatly smelling the leather as she handles them in front of you.

'How astute you are,' she says brightly. 'Indeed the shoes are for long legged, pretty ladies - for those who want to show off all their attributes. Like yourself.'

'But...' you protest.

'Trust me, Darling,' she interrupts. 'I know you've got great shapely legs, but I could not in all conscience allow my darling to set forth transformed without a pair of shoes with such impressive heels.'

She gestures you to sit and like Cinderella in that famous fairy tale she guides your stocking covered toe into the shoe. 'If the slipper fits you shall go to the ball,' she chimes.

The shoes do fit. To be honest they pinch a little and the towering heels throw you awkwardly off balance but your in awe and secretly, despite all your misgivings - love them.

'Oh! Darling,' she gasps raising her hands to her mouth, 'the moment you walk into a room, heads will swivel and the guys will flutter around you like flies. I don't know what it is - those shoes, your long willowy legs, firm pert tits, tiny waist or wide womanly hips, you girl - you've got it in spades.'

You blush as she walks around you obviously pleased with your feminisation and positive reaction. You shrug and play along with the charade rubbing your hands over your silky body, pulling the slip upwards so she catches a glimpse of lace stocking top and heavens - a tantalising glimpse of pantie.

'I'm not sure if I want to be a good girl, I want to be a bad girl.' you say in the highest pitched voice you can muster.

'Oh! Darling yes. I'd like it too but I'm sorry to say you're a very good girl, come and sit on the sofa while I paint your pretty nails - I did promise. Perhaps we can be bad together later.'

Eagerly you sit as she directs, careful to cross your legs to avoid flashing your cum stained panties.

You love the swish of nylon as your legs rub together and the sensation of slip gliding against pantie, glazing over your baby smooth skin is heavenly and you squirm secretively revelling in the unfamiliar sensations. But more is to follow - She's not content to just paint your nails but insists on cementing a set of long, ridiculously impractical false nails before painting them. Something else is strange - she talks to you differently. She talks, no purrs to you in a slow sexy drawl. But it's not just the way she talks - it's what she says. You slide deliciously on your arse and squeeze your nylon coated legs together as your firm cock threatens to explode once more.

'I've got more balls than you darling.' she says, 'I'm seeing a new you and it's doing something to me that's driving me crazy. Give me a good reason why I shouldn't keep you in panties - at home, for work, whenever, forever. I want to see your cute arse in sauce-pot scanties: Agent Provocateur chiffon ones with a zebra motif and trailing ribbons; plush purple velvet ones by La Perla, with darling covered buttons; gaudy silk ones from Pucci, in a heady swirl of ice-cream colours.' She sniggers picturing you in her desires, 'I'll throw away your sensible male briefs and boxers and fill your underwear draw with sexy cami-knickers, lace shorts, mini briefs, figure hugging hipsters and g-back briefs. Sexy but almost entirely useless.' She closes her eyes momentarily, flutters her long lashes, licks her pouting lips and rubs her breasts in a manner you've never seen before. 'Pink, cream, aqua, red, camel, nude or even black I don't care what as long as they're frilly, fiddly and feminine and are firmly on your dear little peach of a posterior.' She slaps your bottom with her hand and laughs. 'You bet I'd follow fashion and ensure all your jeans hang low, that's right, off the hip so boys and girls can see your preference for girlish sexy undies.' She giggles and lets her hands rub down her body glancing over her own lacy panties, pausing over her groin pressing with her inquisitive fingers. 'Mmm!' she moans, 'You're really turning me on. I'm so hot. Does this mean I swing both ways? Am I a lesbo? Perhaps I need some girl-on-girl action?' She laughs but for the first time this evening you're not sure if she's joking.

With your nails done she turns her attention to your face, applying cool foundation, lashings of mascara, eyeshadow and a pink lipstick topped with a sexy wet look gloss.

'I should book you into my beauty saloon for some treatments - they like a challenge. Susie could sort you out with a new hair style, manicure, a pedicure, brow tidy and a full facial. There's nothing we girls like more than a gleaming head of hair and beautiful skin to fill us with confidence.' she chuckles to herself and for a moment your there. With sexy Susie in her swanky, Knightsbridge salon dressed in a stunning, incredibly short, white mini dress and fuck me heels. You're lounging on a leather recliner, legs outstretched, like M'lady as Susie paints your nails and her able assistants preen you to perfection paying special attention to your feet, hair and face. It's heaven.

Of course you consider objecting but you're enjoying the attention - everything seems so comfortable, having make-up applied to your face seems the most natural thing in the world.

'

'The foundation is a super sleek, non-greasy veil of colour that doesn't clog pores. The eyeshadow doesn't slip off and this gorgeous mascara leaves every lash gently curled. You'll look a beauty with this on.'

When she's finished you flutter your long nails, bat your eyelids and purse your lips to kiss her but she doesn't reciprocate. She seems to have lost interest. You begin to feel duped and rather foolish as she dabs your neck and wrists with a sweet smelling floral perfume that epitomises everything in a lady.

You swallow hard. 'I'm feeling stupid and a bit nervous,' you admit quietly.

'Darling, darling, darling,' she says as if talking to a young child. 'We aren't nervous, are we? You've no reason - you look beautiful. Of course we remember we've got our cream stockings. Ooh, pretty stockings! We've got our high heels. Towering, towering heels! We've got our lacy panties. Mmm, pretty lacy, lacy panties! All you've got to do now is show me who's a girl. Who's the girl, darling? Who's the girl?'

'I'm the girl,' you say uncertainly. 'I'm the girl.'

She smiles triumphantly and rewards you by slipping a pink multi-strand bracelet on your slender wrist, a pink flower choker round your neck and a pink rose corsage in your long hair.

''Don't you think I look ridiculous enough as it is?'

'Shut up, darling. What do you know? Leave this to me I know I'll say when to stop. These clothes are just one facet of being a girl... I mean the game,' she corrects herself. 'It's a state of mind. I need to knock off those ugly masculine edges and I'll do what it takes.'

'Can't you love me the way I am?' you say

'Hmm!' she purrs

You smile coyly and try to look as dismissive as possible. 'I'm all girl,' you say, 'I feel so sexy and feminine.'

She sniggers devilishly 'Good girl,' she says taping your arse with approval in a patronising way. 'Now you look so pretty and you're the girl I want you to do something for me.'

What does she want you to do? Can you guess? You decide.

To be continued...

Tomsparty
Tomsparty
645 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousalmost 8 years ago
Second Person Failure

It takes a great story superbly told to make 2nd person perspective work. Regretfully, this one doesn't.

BimboBambiBimboBambiover 12 years ago
a captivating tale

For a story that has barely any actual sex involved it is, by far, one of the most erotic tales I've ever read. Picturing this erotic experience in ones own mind can not help by captivate the reader. I was enveloped by the description as I my imagination let me feel what he felt and wish it was a first hand experience.

AnonymousAnonymousover 13 years ago
lucky

Ipretend it,s me and my wife doing something so wonderful. more please

Flintstone54Flintstone54over 19 years ago
WHAT ABOUT ME :)

The Heck With What Is Going Too Happen Too Him ... My Black Silk Panties Are Full Of Cold "CUM" ... Smearing It All Over My Aching Balls ...

bobojnrbobojnrover 19 years ago
love it

i agree with shawnee, i'm looking forward to the strapon coming out. love the lingerie.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Birthday Present Pt. 01 He becomes his wife's lovely lesbian lover.in Transgender & Crossdressers
Feminized by My Girlfriend The start of how she changed my life.in Transgender & Crossdressers
Dressed for Sex He experiences fantasy: feminized by female friend.in Transgender & Crossdressers
More Stories