Sissy Cynthia

by Silk Sissigan

  PartOne: Sissy Cynthia's Permissive Mother

  'Hi Mom,' said Clyde Dreamer casually as he entered his home.
'Hi, Clyde,' replied his mother, Sharon, 'I'd like to talk to you for a minute.'
'Oh, alright...' he sat down, opposite her.
'Clyde...' she began carefully but purposefully. 'Clyde dear, I know about your hobby.'
'My- hobby?' Clyde squirmed in his seat.
'Yes, Clyde. I know you've been wearing my underwear and my clothes.'
'I... I...' stammered Clyde, out of breath.
'Darling,' his mother took his hand caringly. 'Don't worry, I want to help you.'

  Clyde, who was 19 and lived alone with his mother, suddenly saw his whole world crumble. He was sure he would be seeing a counsellor, perhaps even a shrink. Besides, his every move was now certain to be scrutinized, he thought glumly.
'I really want to help you, Clyde,' she continued, 'I'd like to help you discover your sensuality. If this is something you like, I think you should be given a chance to experience it to the full and see where it takes you. So, come with me, Clyde, let's see how we're going to plan your wardrobe.'
'Er- I beg your pardon,' Clyde snapped out of his dismal expectations. 'Sorry, Mum. You mean, you actually want me to...'
'Wear women's clothes? Yes, dear.'
'But, I thought-'
'Don't worry, darling. I want you to be happy. I'm a woman myself, you know. I know what it's like to feel excited about a dress. To wear make-up and silky underwear, and feel pretty and feminine.'
'Mom, are you serious?'
'Of course I'm serious, darling. Come with me- let's make this whole evening about you and your feminine side, honey.'
'Oh, alright, Mom,' said Clyde, still surprised.
'I've noticed you've been all over my blouses, darling. Is that your style? Skirt and blouse... with a string of pearls... or do you like dresses too? Tell me what you like, honey, and I'll fill your wardrobe with it! You'll be so happy! So pretty! As pretty as a doll!
'Mom, please-' protested Clyde.
'Oh- sorry, darling. Am I getting too carried away? Erm- tell you what... let's start from the beginning, shall we? First we'll do your face and hair, then we'll move on to underwear and apparel, and then we'll accessorize you.'
'Mom, this is all so-'
'Unexpected? A little weird? Yes, I know, Clyde. How do you think I felt when I found out? But I got over it and decided your happiness was the most important thing. I want you to be happy, Clyde, so tell me right here and now: how much do you enjoy dressing up as a woman?'

  Clyde looked at his mother without saying a word.
'Clyde, this is no time to be shy, darling. I'm offering you the pleasures of your dreams on a silver platter. How badly do you want this, Clyde? Tell me.'
'Oh, Mom, I want it more than anything in the world!' said Clyde dramatically, bursting into tears.
'There, there, honey. There, there,' his mother comforted him gently. 'Don't you worry about a thing, sweetie,' she wiped his tears. 'Cry all you need to, honey. But remember - always cry before putting on your mascara,' she joked.

  Clyde laughed between his wet sobs, and the atmosphere surrounding the mother and the son changed to one filled with relaxed confidence and pleasurable discretion. Clyde felt wonderful in his 'feminization chair', paying close attention to his mother's explanations of the different stages of make-up application. His clean-shaven young adult's beard didn't pose much of a challenge for Sharon's expensive foundation, nor did his eyebrows cause any particular trouble - once they'd been plucked to two pencil-thin arches! With every new stage of his emasculation process, Clyde felt more and more excited - even visibly so!
'Oh, gosh- I'm sorry, Mom,' Clyde apologized for his stiffness.
'It's okay, Clyde, dear, don't worry about it. It only tells me I'm doing the right thing for you, and when we figure out what sort of sexual partner you like, I'll make sure that you meet the person you need.'
'Oh, Mom!' Clyde blushed in embarrassment.
'Well, darling, we're doing this for a reason, remember? I want you to be happy. God only knows how long you've been frustrated and unhappy, right? Well, come to think of it... you have already discovered, you know- haven't you?'
'Mom-' implored Clyde.
'Good heavens! ' Sharon realized the truth. 'You're still a-'
Clyde nodded his head quietly.
'That's okay, honey. I'm glad you are.'
'You are?'
'Of course I am. This way you will get what you really want instead of having to pretend you're something you're not. Do you dream of a prince on a white horse, sweetie?'
'No way, Mom!' protested Clyde.
'Are you sure?'
'Yes, I'm sure, Mom!'
'Okay, darling. Just think about it and tell me when you're ready.'
'I will, Mom.'
'Great... And now I have a special surprise for you- I didn't wanna tell you before because I wanted it to be a special moment,' announced Sharon excitedly, producing a sequined red box and pulling an elegant blonde wig out of it. 'This stuff is the best, I'm told', she said as she carefully arranged it on Clyde's head. 'You know I wouldn't buy you anything cheap, darling, don't you?' 'Oh, Mom. It looks stunning!'
'No, honey- you look stunning! Look at yourself in the mirror- you're a gorgeous young woman, aren't you, honey?'
'Yes, I am,' said Clyde, in awe of his mother's creation.

  Neither the mother nor the son could trace the slightest vestige of masculinity in the feminine visage of the new, transformed Clyde.
'Clyde, dear, you'll need a different name real soon, you know.'
'My thoughts exactly, Mom,' agreed Clyde, disguising even his voice behind a fairly convincing imitation of a girly way of talking.
'My God- you even sound like a she,' marvelled Sharon. 'Is there a name you like?'
'Well, I thought maybe... Maybe Cynthia, Mom...'
'I like it, honey! Cynthia it is, then. Now let's get you dressed, Cynthia!' she took Cynthia on her arm and led him to her fabulous walk-through closet, which Cynthia knew only too well.

'Just tell me what you like, sweetie, and don't worry about a thing, okay?'
'Okay, Mom.'
'Yes, please, Mom. Pleated is my favourite. Petticoat too. And I also like pencil skirts.'
'I knew you'd have good taste, honey,' said Cynthia's mother, picking out a number of pretty skirts on soft, plush hangers.'
'Yes, Mom! White billowing ones, with puff-sleeves and bows and frills.'
'Lovely, dear,' his mother selected a number of blouses. 'Floral?' she inquired, pulling out a powder pink one.
'Oh, yes- that one's gorgeous!'
'Yes, Mom, absolutely! Cardigans... cropped pink v-necks with beady pearl buttons.'
'Hmm, I'll have to buy you some of those, then,' said Sharon, browsing through her elegant knit section. 'How about this one?' she produced a baby blue bolero cardigan with self-clad buttons along both fronts and delicate knit bows for decorative details.
'Mom, it's to die for!' said Cynthia breathlessly.
'I agree,' nodded Sharon approvingly. 'If you like it so much, I'll have you smothered in this stuff,' she chuckled contentedly. 'I know just the store.'
'Dress?' she moved on to a different part of her fashion empire.
'Yes, Mom! I can't resist them! With pretty rounded collars and frothy petticoats!'
'Hmm, of course you'd want something like that,' said his mother, rubbing her chin in deep concentration as she riffled through her cocktail dresses. 'We'll have those ordered to measure, you know,' she decided. 'Although, for now-' she shifted dress after dress, with the delicious rustle of glorious fabric, '-perhaps this sort of thing?' she pulled out a primly designed pink gown with a pretty white collar, adorned with a perky white bow.
'Oh, Mom, it's so pretty!!' said Clyde, in a voice close to a moan.
His mother just smiled contentedly, as she held the dresses in front of him, tilting her head in judicious style-assessment. As the dress brushed against Clyde's cock, his stiffness clearly showed through its fabric.
'Clyde dear,' she said, 'I can see how much you love being a girly transvestite! From now on you will lead a life of feminized luxury, and your name will be Cynthia Travesta!
'Thank you so much, Mother - it's a dream come true!'

'Pearls?' Sharon asked next.
'I adore pearls, Mom!'
'Yes, of course you do, Cynthia sweetie- who doesn't? By the way, we'll have your ears pierced tomorrow - so you can wear a string of pearls with matching earrings.'
'Gee, thanks, Mom.'
'Well, we have quite enough for now, don't we honey? Let's get you into some underwear and get you dressed all nice and pretty.

What a great thing we're the same size, sweetie- don't you think? We even have the same shoe size - with those little feet of yours!'
'Oh, yes, Mom, it's great we share the same size. You have such wonderful stuff!'
'Yes, I do honey, don't I? And soon enough, you'll have a pretty little wardrobe of your own. Actually, I can't promise you it'll be little, but it definitely will be PRETTY!' she laughed, throwing him an excited glance. 'Just you wait till I get my hands all over your feminine side, Cynthia dear- you'll never wanna be anything else again!'
'Mom, you're the greatest!' Cynthia and Sharon embraced affectionately, their eyes moist with joy. A little while later, Cynthia was all corseted (for that waspie waist everyone likes and wants), stockinged and pantied. Her hair was curly and silky, her lips pouty and glossy, and her wrists as limp as satin. She had never felt happier!


Things were certainly working out for Clyde that summer. Just before his transformation into Cynthia Travesta by his feminization-permissive mother, Sharon and her son had decided that Clyde would take a year off education to think about the future direction of his life and try to find his 'true self', in order to make the best career choice the following year. Now Sharon had decided it would be best for Clyde to spend that entire year as Cynthia, and as for Clyde... well, no-one heard him complaining about such an arrangement.

It took a mere two weeks for him to completely surrender himself to his feminine side, all prettified, ear-pierced, and contour-corseted, drooling over his own beauty in the shape of gorgeous Cynthia, who could often be found posing in front of a full-length mirror. His mother had even encouraged him to masturbate himself to that image, as she didn't want him to miss out on any more sexual gratification (being a virgin at his age). He was rather shy about it at first, but when she 'took matters in her own competent hands', he soon learned to pump himself to seventh heaven while discussing the particulars of his outfit with his wonderfully permissive mother.

Each time she dressed him in a new girly outfit, Sharon seemed as excited as Cynthia herself, cherishing his sissified narcissism with motherly pride. She loved dressing him in hobble skirts that would limit his movement and maximize the experience of 'force feminization', though she didn't exactly have to 'twist his arm', as he was only too willing to play the part.

Then his third weekend as Cynthia Travesta came, and he felt he was ready to confide in his mother the final piece of information she was waiting for.
'Mother, dear, I was wondering if I could have a word with you,' he said tentatively during breakfast.
'Why, of course, Cynthia sweetie. What's on your pretty little mind, honey?'
'Well, Mother, I suppose you still remember telling me that I could speak to you about- about the kind of partner I'd like to meet.'
'Yes, of course, honey. Have you made up your mind then?'
'I have, Mother.'
'Why, I can't wait to hear it,' said his mother, continuing chattily, 'I trust you took the advice I gave you, Cynthia darling. You know: when in doubt- follow the passion!' they finished together.
'Yes, Mother, I have given it a fair amount of thought, and I have come to the conclusion that I'd like to meet a-' Cynthia paused for a moment.
'Yes, darling?' Sharon was all ears.
'I'd love to meet a lady... of a more mature kind.'
'How mature exactly, Cynthia dear?'
'40s mature, perhaps 50s...'
'Alright, darling,' said Sharon, taking in the info. 'Blonde or brunette?'
'Short or tall?'
'Body build?'
'Curvy plump, or curvy hourglass?'
'Curvy hourglass.'
'Fashion style?'
'Prim and chic, with a touch of retro...'
'I can see you've really given this some thought,' said Sharon, impressed. 'You know, I think I might like to take you shopping today, Cynthia honey,' she announced, somewhat mysteriously, chucking her 'daughter' under the chin fondly.
'Oh yes, Mother, how wonderful!' exclaimed Cynthia, eager to go on another shopping spree with her mother, who had already showered her with girly delights most lavishly on several previous occasions.
'Let's go and fix our make-up a bit, and then let's hit the stores, Cynthia sweetie!'
'By all means, Mother dear!'


In the first store, Sharon and Cynthia found some very exquisite hosiery and underwear.
'Is it for you, Madam?' the shop attendant asked Sharon, slightly confused.
'No it's for my daughter,' Sharon pointed at Cynthia.
'But she's a he, isn't she? I mean, isn't he?' said the shop attendant - a short, tight-bunned woman in her sixties, who couldn't seem to stop peering at Cynthia quite intently.
'Excuse me, but to put it quite bluntly, Madam, that's none of your business!' replied Sharon to the shop attendant. 'As you can see, my daughter is gorgeous, and that's why she'd like to try on some gorgeous lingerie - if you don't mind!'
'Certainly, Madam,' the shop attendant abandoned her attitude, 'this way Miss-'
'That'd be Travesta,' replied Sharon. 'Her name is Miss Cynthia Travesta.'
'And a positively gorgeous name it is,' said the little lady. 'This way, Miss Cynthia Travesta...'

A little while later, Cynthia and Sharon exited the shop, each toting a couple of elegant boutique bags, ready to hit the next store... and the next one... and the next one...
After a whole morning of shopping, with twenty-seven bags now safely stashed inside Sharon's vast Mercedes-Benz, they headed for some lunch at George's, a fancy downtown restaurant.

Somewhat to Cynthia's surprise, they were joined by a friend of her mother's, Ms Lorna Lovely, whom he had never met before. Cynthia was sure he'd never met her, because he would've surely remembered a face of such beauty and charm. Ms Lovely was a gorgeous brunette with mesmerizing blue eyes and exquisitely carved cheekbones. Her broad, handsome jaw lent her an air of cultivated mature beauty, which was further enhanced by the wavy locks of her lustrous hair.

Her lips were full and sweet in the most seductive way, and her smile was uniquely warm and captivating. Every aspect of her make-up, clothing and jewellery seemed immaculate - there was no doubt: Ms Lovely was both the primmest and the prettiest lady Cynthia had ever met, and he was simply unable to take his eyes off her throughout the lunch, basking in her radiant smiles of approval, while his mother told Ms Lovely about the wonderful progress her 'new daughter' was making every day.

As lunchtime drew to an end, amid a relaxed and cordial atmosphere, the three ladies left the restaurant and went to Ms Lovely's house for a pleasant afternoon chat over a cup of latté. Cynthia was encouraged by both her mother and Ms Lovely to try on some of her new purchases, and both ladies applauded enthusiastically every time she posed in a new look, calling her to come and sit between them so they can admire her at close range.

Dressed in a delicate powder-pink blouse, with multiple strings of fine pearls, Cynthia looked more feminine than ever, her cheeks all rosy and her eyes riveted on Ms Lovely's entrancing smile.
His mother leant towards him from behind and whispered in his ear: you have surely guessed by now why we are here today, Cynthia darling... this is a very special day for you, sweetie... this is THE day, she chucked his chin from behind, guiding it gently towards Lorna Lovely's smiling face, until their lips united in a sweet, soft kiss, filled with longing and passion.

A wonderful kissing mate and a seasoned sex goddess, Ms Lorna Lovely was a delightful bed-companion for Miss Cynthia Travesta, whose life as a virgin was about to come to an end. As the two lovers moved onto Ms Lovely's stylish canapé, Cynthia's obliging mother even liberated his bursting skirt-stick from his silky panties and slipped a condom over it, just before it slid into Ms Lovely's eager 'pleasure slot' that was dripping with desire.

Although Cynthia was the one with the panty-rod, Lorna Lovely took all the initiative on her canapé d'amour, while Sharon watched her 'daughter's' deflowering with tender pride and poignant interest. She had taken every care to orchestrate a memorable sensual experience for Cynthia in coupling her to Lorna, one of her most trusted friends from the past. In fact, while there were both at law school, Sharon and Lorna shared a brief but intense lesbian romance, which both women remembered as one of their most gratifying life experiences.

Today, as she witnessed her 'daughter's' first sexual act, Sharon was delighted to see the extraordinary chemistry between Lorna and Cynthia, who were copulating passionately in a tight, loving embrace. Cynthia looked gorgeous in her frilly pink baby-doll with pink stockings and white garters, and Lorna was clearly taken with Cynthia's long, slender 'pantypole', which she rode like his Cleopatra, his Persephone, his Venus! Sharon's only son - now a daughter - was happier than ever, and that was the only thing that truly mattered.

Lorna was now on top of Cynthia, who was moaning like a horny college girl, with her slender legs high up in the air. A true expert in long lovemaking, Lorna Lovely had given Cynthia Travesta an unforgettable erotic initiation, driving her to a climax far more fabulous than any masturbation experience could have generated!

The lady and the girl were truly smitten with each other - so much so that they repeated their lovemaking five times, filling the time in between with changes of clothes and passionate kissing. Just as Sharon had expected, the encounter she had arranged had such a powerful effect on Cynthia that she simply had to leave her in the competent hands of Lorna Lovely for a whole week, visiting regularly for a first-hand experience of the most important week of her daughter's life.

In the celebratory atmosphere of her sexual awakening, Cynthia found himself showered with gifts by both Sharon and Lorna, who bought him flouncy baby dolls with pleated petticoats, blouses of indescribable feminine beauty, and the softest cardigans in every shade of pink known to fashion, adorned with girly bows and beady pearl buttons.

Cynthia was in a state of constant ecstasy, madly in love with Lorna and with his new, feminized self. His mother had been so good to him: so generous, so understanding, and above all - so PERMISSIVE! She had given him the life he had been craving and supported him in every way. In the irresistible person of Lorna Lovely, she had found him the woman of his dreams and delivered him right into her bed to experience the most intense pleasure of his life.

He thought of all the clothes, the shoes, the accessories...! Had anyone ever felt happier than him right now?! Was it even possible for one to feel happier? Cynthia had realized he never wanted to be called a 'he' any more. He was a SHE now - Miss CYNTHIA TRAVESTA!


Part two of Sissy Cynthia will be in issue #11 of Prim's Petticoat Pansies