Silken Embrace

by Christina Shelly

  Rupert is now a vision of the most delightful and exquisitely humiliating forced feminisation. He is dressed in a gorgeous powder-blue dress made from a shimmering satin. The dress is rather like mine, but even more excessive in its sissy design. With a very high thickly be-frilled neck, long puffed sleeves and a very short skirt resting on a cloudy sea of white frou-frou petticoating, it is a deeply traditional, but no less impressive tool of feminine control. Pulled over the dress is a white silk pinafore, at the centre of which is a hand-embroidered teddy bear design. Rupert’s long and highly feminine legs are sheathed in semi-opaque white nylon tights and his small girlish feet are imprisoned in light-blue patent leather Mary Jane shoes with diamond butterfly buckles. His hands are sealed tightly in satin fingerless mittens and a large highly ornate powder-blue bonnet is tied tightly in place at his dimpled chin with a fat sissy bow.

  I stare at him and he stares at me. His eyes are covered by a film of tears, yet there is also clear evidence of a deeply reluctant but also irresistible sexual excitement, a fact made shockingly clear by his violently erect and exposed cock. Yes: through the wall of petticoating one thing is stunningly apparent: his penis, which has been wrapped in a white nylon stocking, has been pulled through a lace-frilled hole set in the front of his tights and left on full and soul-crushing display.

  ‘Rupert – come here!’

  Poor Rupert then performs a rather pathetic version of a bob curtsey and shuffles over to his beautiful ample mother.

  ‘Into the pen and on your knees,’ she orders.

  His eyes wide with fear and something that might be anger, he hesitantly enters the pen. He looks down at me and I stare up at him, his long very hard sex hanging over my head like a particularly bizarre sword of doom. He then very slowly kneels down in front of me.

  It is only now that I can see his face has been painted with thick white foundation. His lips are a light pink, and the small beauty spot remains at the side of his very kissable lips. Up close, it is clear he is very pretty and my arousal is stoked considerably by this sudden clearly erotic closeness.

  Ms Ambrose returns to the pen armed with two lengths of white silk ribbon. To my delight, she kneels between us, allowing her skirt to ride up her broad firm black nylon-sheathed thighs. The smell and sight of her is quite overwhelming and I can’t resist a high-pitched moan of the deepest sissy pleasure. It is also apparent that Rupert is in a highly agitated state of sexual arousal and, as his sex rises up from beneath the layers of scented petticoats, he too moans helplessly.

  ‘I thought it would be nice if you could spend some time getting to know each other a bit better,’ she says, her voice now back in sensual maternal mode. ‘But we don’t want you getting too intimate, so you’ll both have to be properly secured.’

  She then tells her pretty, expertly sissified son to put his arms behind his back, with the wrists crossed. He obeys with a slight reluctance and she turns a stern yet incredibly lovely look upon him that inspires swift compliance.

  She binds his wrists tightly together with one of the ribbons, and uses the second to bind his ankles. To do this she has to lean across his back and I find myself with an eye-popping view of her large sexy backside, the check skirt stretched tightly across it, the backs of her hosed thighs now visible right up to the edge of a pair of white silk briefs.

  As Ms Ambrose secures her sissified son, Ms Gillette places a small pink silk bag on the floor of the pen. As she leans forward, our eyes meet and I behold a dark cruel contempt whose root I have long suspected: my relationship with Aunt Jane, the woman who was once Ms Gillette’s lover. I know my humiliations and punishments will be doubled in ferocity when administered by Ms Gillette, and I know why.

  Then Ms Ambrose is turning her wondrous attentions upon me. She has extracted more lengths of ribbon from her skirt pocket and within a few minutes my wrists are tied tightly behind my back and my ankles are bound firmly together. The gorgeous buxom matron then leans between us and picks up the small rubber bag. From inside, she takes a pair of white silk panties very similar to the ones that I had seen so sensually covering her considerable and very beautiful backside.

  Rupert’s eyes widen significantly when he sees the panties, and he watches utterly entranced as his lovely mother carefully arranges the sexy intimate underwear so that the gusset section is inverted and exposed. He looks at her and she smiles warmly. He shakes his head slightly and mutters a weak, girlish ‘Please, mummy’. Yet his tone is far from fearful and his cock, peeking desperately through the seas of petticoating, strains angrily against the fetishistic embrace of the sheer white nylon stocking so erotically entrapping it.

  ‘Yesterday’s panties, petal. Just how you like them.’

  He moans with helpless need and then Ms Ambrose gently presses the gusset of the panties against Rupert’s flaring nostrils. His eyes widen even further and his moans become muffled squeals of an unbearable sexual arousal. He shakes his head more fiercely and she presses harder. His cock bounces up and down desperately in its nylon prison. His eyes meet his mother’s and there is only an intense and provocative collision of desire and love. And all the time Ms Ambrose is whispering ‘you poor thing, there, there, this’ll make you feel so much better’.

  I watch astonished and intensely excited as this ritual – obviously played out on many occasions previously – is performed with a careful teasing precision.

  As Rupert helplessly breathes in Ms Ambrose’s most intimate fumes, I envy him with a terrible aching passion. I am hoping that I too will soon be able to sample the delights of the panties, but then, to my bitter disappointment, Ms Ambrose removes the panties, folds them up into a tight ball and very gently teases them into Rupert’s mouth, creating an erotic and sensually pungent gag.

  Ms Ambrose then extracts what looks like a very large white plaster from the bag. It is as wide as her hand and about ten inches long. She tears it from its base and very slowly, almost teasingly spreads the sticky side across Rupert’s stopped mouth and bulging cheeks, very effectively gagging him.

  The plaster covers the whole bottom half of Rupert’s face and creates a strange seamless space that focuses all attention on his large helplessly pleading green eyes. And, of course, he looks almost unbearably gorgeous. I find myself staring at him with a renewed and utterly perverse desire.

  Yet his ordeal is far from over for as soon as Ms Ambrose is satisfied that her son is soundly gagged, she returns to the bag. From inside, she takes what at first appears to be a length of very narrow silver chain. Attached to each end is a slender pink rubber shackle.

  She then proceeds to take a firm grip of poor Rupert’s large nylon-enveloped cock in one hand and slips the shackle over its thick length with the other. He squeals with dreadful arousal and a frustrated despair as Ms Ambrose pulls the shackle down the length of his sex and then snaps it into tight inescapable position around his stockinged balls.

  ‘Very snug,’ she whispers, turning to me and bathing my stunned eyes in the sexiest and wickedest of smiles.

  I watch helpless and overwhelmed as she proceeds to lower my panties back down around my knees and slip the second shackle over my tightly restrained and burning sex in exactly the same manner.

  I cry into the dummy gag, a cry that is transformed by the fat teat into a high-pitched sissy squeal of utter sex agony. Then the shackle is fitted over my balls and I am attached in a most intimate and perverse manner to the lovely Rupert.

  The chain is about eighteen inches long and, as Ms Ambrose has fitted me with the shackle, poor Rupert has been dragged painfully forward on his knees so that he is just over a foot from my babified form. Indeed, we are now so close together that the billowing petticoats of our sissy costumes are quickly entangled and his sex is brushing provocatively against the edge of my dress.

  ‘There. Two very pretty peas in a soft cuddly pod.’

  Ms Ambrose’s teasing words tickle my ears with a dreadful potential as she climbs to her high-heeled feet an
d slips out of the playpen, shutting and locking the door behind her.

  Then I am facing pretty, slender Rupert, his alabaster cheeks bulging with the fat panty gag, his eyes wide with shocked arousal and a deep inescapable attraction. I blush at the obviousness of his need and then stare down at his large hard straining cock. It is so beautiful in its delicate stocking prison, and I know now that I want him, that I must, at some point, be his and he mine.

  My sex, freed of the scented embrace of the panties, rears up beneath my own elaborate petticoating and then, to my surprise, Rupert edges forward slightly so that the sealed tips of our cocks are touching, thus expressing a simple truth: a terrible aching mutual desire.

  I look at him and moan weakly, trying to communicate through the fat dummy gag. Thanks to the thick broad tape gag and the large pungent panties filling his mouth, it is impossible for him to make even a whimper of reply, but his wide sex-addled eyes and rock-hard nylon-wrapped cock say all that needs to be said.

  Then this strange, kinky, so terribly arousing adventure takes a new and even more perverse turn. As we snuggle together, Ms Gillette and Ms Ambrose slip from the room, only to return separately, Ms Ambrose within minutes and Ms Gillette about a quarter of an hour later.

  Ms Ambrose re-enters the Nursery pushing what looks like a flat-bed metal trolley upon which has been mounted a long thin pole. As she wheels it into the centre of the room, and thus a few feet from the playpen, I manage to get a slightly better view of the odd device and begin to understand its wicked function.

  Closer inspection reveals the peculiar trolley to be a variation on a device I had seen used and been a victim of in the training academy of the Sissy Maids Company. The pole, made of a rubber-coated and very resilient metal, ends in a curved plastic vibrator, turning it into a giant metal phallus. At the foot of the pole are two white rubber shackles, positioned about a foot either side of it. They are attached to short lengths of metal chain soldered into the trolley base.

  Already I have a good idea of what is to happen next. And when Ms Gillette returns, my confident interpretation is confirmed for the striking cruel-eyed blonde is accompanied by Myriam, but not the confident beautifully uniformed maid Myriam. No, this is very much slave Myriam on the verge of a most awful and well-deserved punishment.

  She is dressed in a sheer white nylon body stocking that betrays her superb pneumatic figure to sado-erotic perfection. Her arms are lashed behind her back and tied painfully tight at the wrists, elbows and just below the shoulders with rubber-lined cording. A strip of the wide long white plaster covers her lower face and holds in place a gag so fat that it is causing her red cheeks to bulge like some beautiful trumpeter in full blow. She is wearing white leather mules with at least five-inch-high stiletto heels. Attached to her neck is a thick blood-red leather collar and fitted to the middle of the collar is a length of heavy metal chain held taught by the tugging grip of Ms Gillette.

  Tears of fear and discomfort trickle down Myriam’s effort-tensed face as she totters forward desperately, looking very much like someone who is about to fall flat on her face at any second. Her large very beautiful breasts bounce desperately before her, and her thighs work furiously to maintain each precarious step. As she is drawn up before the sinister trolley I see that a series of red welts are clearly visible through the white sheer nylon along the back of her thighs.

  Momentarily, I feel a helpless sympathy. But then I remember the earlier torments she inflicted upon me and I prepare with great eagerness to witness her terrible punishment and awful humiliation.

  As soon as Myriam has been brought before the dreadful phallus, Ms Ambrose steps forward and grabs her roughly by the arm as Ms Gillette disconnects the chain leash. The two women then lift her up into the air. She squeals desperately into the all-pervasive and very tight gag, her eyes full of panic and wild fear. She stares over at Rupert and myself and sends us a pleading look. She is begging for a non-existent mercy, and we stare back at her with a helpless and deeply sadistic arousal.

  ‘She’s soaking,’ Ms Gillette says, her voice weakened by the effort of lifting Myriam. ‘I worked on her with a dildo for ten minutes before bringing her down.’

  Ms Ambrose nods in a cool businesslike manner, and then the two women struggle to position the now frantically wriggling blonde beauty over the curved vibrator head of the pole.

  Eventually they manage to get her over the top of the pole and then pull her legs down towards the shackles. Ms Gillette, grappling with a struggling leg, manages to slip the rubber shackle over Myriam’s elegant testing high-heeled shoe and then around her ankle. This has the effect of completely undermining a co-ordinated resistance and, within a few seconds, Ms Ambrose has secured the other ankle.

  We watch, astonished and dreadfully aroused, as Myriam begins her terrible torment.

  As soon as she is shackled, the two women step back to view the results of their kinky handiwork. Initially, Myriam manages to stand on tiptoe, so that her shaven and very wet sex, which is exposed via a be-frilled slit in the gusset of the body stocking, only brushes against the tip of the vibrator. But this puts a very significant pressure on her thigh muscles, and then the vibrator begins to buzz angrily, a high-pitched electrical shrill that fills the room with a sense of impending defeat. Poor Myriam’s sex continues to brush dangerously close to the vibrator, thus ensuring that it is teased and tickled by the buzzing curved head. Sweat pours from her straining face and her eyes are wild with horror-framed panic. She squeals and wiggles. But the more she struggles, the closer her sex comes to the fiendish eager head.

  Then she is forced to relax her thigh muscles and the whole of her body weight forces her sex down onto the head of the vibrator. It slips deep inside her without the slightest resistance. And then she is held fast and helpless and her squeals of fear and anger quickly dim. Indeed, despite her obviously heartfelt attempts at resistance, it is all too apparent that she is overwhelmed by the erotic ministrations of the vibrator.

  A cruel excited smile crosses Ms Gillette’s full cherry-red lips, and it is clear that Ms Ambrose is highly aroused by the sado-erotic spectacle of the lovely Myriam’s just desserts.

  Ms Gillette takes a vibrator control from a pocket in her jacket and points it at Myriam’s plump, perfectly formed and tightly nylon-wrapped backside. She turns the control dial and the French beauty releases a high-pitched squeal of shock and even deeper sexual distress. Immediately it is clear that an anal vibrator is adding to the considerable torment of the one now buzzing away furiously inside her soaking cunt. Ms Ambrose, a distracted glaze in her beautiful emerald eyes, comes over to the pen and looks down on us, a goddess beholding her deliciously perverse creation.

  ‘Myriam will remain with you for the rest of the day. A little bit of performance art to enhance your pleasure.’

  Then she looks over at her wiggling moaning son and her eyes widen with cruel passion.

  ‘As you can see,’ she says, addressing me, ‘Rupert is not restrained and is considerably excited. If he comes during this little meeting of sissy souls, then I am afraid he will be punished. This punishment will take four forms: his sex will be dyed hot-pink with a long-life body paint (an intervention I believe you have already experienced), a pin-lined restrainer will be fitted, as will a suitably powerful anal stimulator. Then, he will be permanently sissified.’

  Poor Rupert shakes his head furiously as his fate is laid out. I look at him and find myself lost in his sensual distress. The more he struggles and squeals, the more beautiful he appears. It is clear he is, in almost every way, an ideal candidate for sissification; and it is also clear that his mother intends to ensure that he quickly enters the ranks of the Bigger Picture she-male army!

  Then she kisses us both on our bonneted heads and leaves us to our desperate pleasures. She and Ms Gillette observe poor Myriam’s sufferings for a few more minutes and then, hand in hand, they leave the room. As the Nursery door is locked, I see a look of sudden and painful real
isation in Rupert’s beautiful eyes: his mother and Ms Gillette are rather more than good friends! And then there is a sudden flash of jealous anger. Yet this fades as his eyes lock once again with mine.

  For the next twenty minutes, Rupert fights the inevitable with a brave but futile determination. He wiggles and moans. His eyes flitter between poor struggling whimpering Myriam and me. Our cocks continue to brush together and the dreadful power of this intimate, strict and very mutual bondage begins to take its toll. On more than one occasion, I watch him try very desperately to shake off his furious sexual arousal. But all such efforts are pointless. The pure soul-crushing pleasure he receives from this elaborate sissification and from his previous costume are all too evident. His attraction to his mother and her wicked ways are also blatantly obvious. Despite his protests, he is enjoying every second of his ongoing and developing humiliation. And I know this is why, ultimately, he will not fight the huge orgasm that is brewing as we wiggle and moan helplessly in the soft yet unyielding confines of the Nursery.

  Myriam’s suffering – our dark entertainment – continues to provide a regular distraction. It is clear that she is being driven quite insane by the multiple vibrator attack. Her nylon-sheathed thighs quickly become soaked in sex juice, and it is obvious she is experiencing regular and very powerful orgasms. Every five or ten minutes, her already rigidly secured body stiffens violently and her eyes widen even further. A slight extremely well-stifled moan of utter ecstasy betrays her primal pleasure, and then the round of helpless stimulation and angry arousal begins again.

  The Nursery is filled with the strange sounds of this great perversion: the muffled squeals of pleasure from Myriam, the helpless moaning of Rupert and my own whimpers of intense and deeply frustrated desire. I stare down at Rupert’s large delicately covered cock and feel a dreadful sense of envy. The stocking so erotically enveloping his sex provides him with the profound freedom of orgasm. The constantly teasing and ever-present Senso restrainer imprisoning my own sex denies any possibility of sexual release. Rupert watches me watching his increasing angry tumescence and then our eyes meet. I imagine our future together in the way I had once imagined my future with the gorgeous buxom Pansy. Then I find myself thinking once again about my first true sissy love and how fate has conspired to pull us apart. I wonder what she is doing now, how she is surviving in the new cruel regime of the Radicals. I remember our delicate but intense lovemaking, the pleasures we found so easily in our transformed sissy forms. I remember her large ultra-sensitive breasts and her helpless cries of animal joy as I covered them in delicate sissy kisses. I remember her modestly sized but beautiful cock, of sucking it gently to eruption, of tasting her hot salty cum. Yes, how much I miss her!