The Care Girls Ch. 04

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Girlfriend dresses you in her clothes.
1.7k words
4.45
90.3k
12

Part 4 of the 6 part series

Updated 10/10/2022
Created 01/06/2004
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Tomsparty
Tomsparty
645 Followers

Chapter 4 - In Too Deep

You gaze at your feminised face in the mirror and smile to yourself. Your lips do look full, juicy and kissable. You shudder and glance down at your long silky legs poking out the bottom of your skirt. Your ankles appear slim and shapely and you wonder how dramatic your feet would look like in a pair of Becky's towering high heels. You then giggle to yourself as you consider how ridiculous they must look in your boys brogues. God, you're excited, nervous and hot. You rub your knees together, you want to see it out. You're convinced Becky is falling for you. You enjoy the masquerade. You want to wear more. You dreamily recollect Becky in her delicate panties and how beautiful she looked. Your convinced you could look as beautiful too. Hmm! You imagine her soft lacy panties encasing your cock and buttocks. You shake your head to clear your thoughts. You know you can do it. You have to do it. Despite your obvious excitement you realise there are dangers. What would your Mother say if she found out? How would the boys at school react? Would Becky go off you if Mrs Wilson learnt the truth? Does she really like boys in skirts? You resign to your fate. You must carry the bluff off so you gently unbutton your crisp blouse and begin padding the bras lace cups with toilet tissue. But how much. What constitutes the correct cup size. You conclude more rather than less. Time ticks by and in your haste you over fill them so the blouse develops so much shape the buttons strain open in a feeble attempt to conceal your prominent tits. You double check your chest in the bathroom cabinet mirror. You grasp them with both hands and massage them into a convincing position. You gasp - they feel so real, they feel part of you. You cup them and admire your cleavage and on doing so one hand drops and slides up your stockinged thigh. Mmm! this feels good.

As you gaze dewy eyed at your reflection your painted hand slides further up your thigh, under your short skirt and strokes your twitching cock. Mmm! You murmur and your mind wanders. You imagine Becky's gorgeous panties stretched over your bum. Hmm! Was she joking? Would she really slip them up your legs? You begin to sweat and you grasp your normally flaccid cock with vigour. You gasp as you pump, slowly at first then with increasing with ferocity. Pump, pump, pump. You forget all sense of time as you're awash with strange sensations that sparkle throughout your body...Then without warning your little cock spasamed, ejaculates and spurts its watery seed into your hand and briefs. You're immediately embarrassed. How could it be that dressing in Becky's clothes made you come and so quickly? This of all times - your first, but you've no time to review your performance as you hear Becky call.

'Hurry up Lucy, your tea will get cold.'

Forcibly awoken you clean yourself up and straighten your hold-ups and smooth your skirt over your hips. Your premature ejaculation wasn't all bad news as your cock has now wilted to minuscule proportions and the front of your skirt looks perfectly feminine. You smile to yourself - you're dazzling and you're ready!

Back down stairs Becky could hardly believe her eyes as she stares at the size of your voluptuous bosom. Even you wonder if you've overdone the tissues when Mrs Wilson looks twice. Now slightly self conscious you climb carefully on a bar stool just as Mr Wilson comes in from the garage.

'Evening,' he says merrily and stops mid sentence on seeing your dazzling feminised form with its huge chest, curvaceous hips, long slender legs and shapely angles. He looks at you closely his eyes roaming hungrily up your long legs, slim waist and prominent breasts.

'Alan,' Mrs Wilson barks. 'Put your tongue back in.'

'Sorry, he says with a smirk. 'I didn't know Becky had an attractive girlfriend over tonight.'

You hold your breath, half expecting him to lecture Becky about uninvited guests. A long silence follows as his eyes sear through you as if mentally undressing you. Finally after what seems ages he smiles sweetly at you, a prominent bulge growing in his trousers. 'and who are you young lady?'

'Lucy,' You say awkwardly before Becky had an opportunity to introduce you.

Mrs Wilson chips in. 'Alan dear, Lucy's been a absolute darling, apparently our baby's been restless tonight and Lucy's been an absolute angel and managed to rock him to sleep.'

Mr Wilson is full of praise and as a sign of gratitude he not only pays Becky ten pounds but he also hands you a fiver for your extra help. But his generosity is not without cost as he lingers holding your painted hand whilst you accept the payment.

'I think we've found another baby sitter Ellen dear,' Mr Wilson says giving you a long lecherous stare. You shift uneasily on your stool and attempt to pull the hem of your skirt to cover your silky thighs.

The next few minutes are a challenge as you have to convince the Wilson's of your femininity. You're a star in the making as you toss your head, flick your shinny hair, pout your glossy lips, flutter your long eye lashes and criss-cross your lycra covered legs. You almost forget who you really are as you revel in your new identity. Whoosh! another feminine wave sweeps through you and you find yourself flirting with Mr Wilson. Becky shakes her head at you and drinks her tea and suggests you leave.

The Wilson's follow you into the lounge and as you pad across the carpet, the pile tickling your toes through the hold-ups, you feel it! What's that? Is that Mr Wilson's hand on your skirt - more specifically your bottom. Did he brush against you inadvertently or was he more deliberate

Will you? Push back onto his hand, wobble your butt tantalisingly and read on or turn round and slap him hard across the face and stop reading now?

Of course you ignore him - you don't want to make a scheme. Then as Becky collects her bag. You freeze. What shall you wear on your feet? You can hardly walk out barefooted or wear your masculine black shoes. You feel your top lip sweat but you needn't worry. Becky thinks fast.

'Here are your heels,' Becky says handing you her own court shoes, 'now where are my old pumps,' she says rummaging in her bag. Triumphantly she pulls out a ragged pair of shoes and slips them on her feet. It's a brave gamble. You sigh with relief and sit on the sofa in an attempt to slip on her shoes. But you've got another problem - Mr Wilson. He can't stop staring at your eye-catching legs and as you struggle to squeeze your dainty feet into Becky's court shoes the slit in your skirt drops rewarding the amorous Mr Wilson with a daring flash of white thigh and lacy hold-ups. You blush convince he'd seen your boys briefs. But that was the least of your worries. The shoes are a size too small and you struggle to squeeze your feet into them. Both Wilson's look at you oddly as you wince and jam your toes inside. After a fearful battle with squeaky leather, silky hold-up and soft skin you stand awkwardly. Your thrown off balance and totter precariously. The Wilson's keep you talking as you step carefully from foot to foot. Mmm! After a while the leather stretches, they feel nice and you feel more complete. As Becky chats you again long for her panties as you feel like a beautiful jigsaw missing a piece.

Eventually Becky steps towards the door and you heave a sigh of relief as Mr Wilson closes the door behind you.

'Lucy, darling, you were amazing.' Becky screams giving you an enormous hug. She kisses you on the cheek and your little cock begins to wake up again.

'I can't believe we got away with it,' you say.

'I can,' Becky shrieks, 'you where incredible. 'You're more girlish than many of my actual girlfriends.'

You cringe and she senses your discomfort. She kisses you again but this time her hand slips under your skirt and lightly touches your briefs and twitching cock.

You pull away frightened you may draw attention to yourselves. You don't want a scene outside so you climb in your car hoping for some more intimate smooching.

Becky's not interested. 'Come on lets go. I can't be too late.'

'Please don't say anything to anyone,' you say as you drive Becky home.

'Oh! That's a shame,' she says coming on strong again. She puts a hand on your nylon covered knee and runs a perfectly filed nail slowly up your thigh.

'Don't,' you shriek almost mounting the kerb.

'Don't what?' she says coyly. 'Don't do this.' Her hand darts back to your leg and strokes your inner thigh.' Don't dress you in my clothes or don't see me?

'You know,' You say as you pull up to her house.

You hope to be invited in so you can change in comfort but Becky doesn't want her parents seeing you dressed as you are.

'You'll have to dress back into your own clothes in the car.' She says.

It's murder.

Have you ever rolled off a pair of silky hold-ups and slipped out of a lacy bra, blouse and skirt in the confides of a small car? It's not easy. Read on if you have, stop now and practice if you haven't.

'Don't tell me you didn't enjoy the experience,' she says as you button your trousers. 'All boys at some time in their life appreciate a little female wandering. Go on tell me that you enjoyed it. I'd like it if you did.'

'Y, Y, Y, Yes.' You stammer.

'Great, I'm so pleased,' she says comfortingly. 'I do want to be friends and now I know how to please you - you can help me out too.'

Your delighted but her friendship sounded as if it was going to come at a cost. 'How?' you say fearfully.

She stuffs her clothes back in her bag and gives you a kiss on the cheek. 'I don't want to spoil the surprise,' she says, 'you'll just have to wait and see.'

Tomsparty
Tomsparty
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jennifurzoejennifurzoeabout 1 year ago

This sissy bitch is just loving where this story is going and wishes it would happen to some people, myself included.

AnonymousAnonymousalmost 9 years ago
Inspirational story

I too am a crossdresser but alas I'm not really totally passable. I wish I was and this story was wonderful to read because it inspired me to try and become passable so that I can experience what Lucy did. I can't wait to read what happens in the next chapters.

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