At first, the idea of being trained by a man was the most challenging of all the requirements of my sissification within the SMC academy. My masochistic bi-sexuality had been well established by Aunt Jane and my relationship with Dominic/Pansy. But Dominic’s feminine beauty and manner and his subsequently very successful sissification put him in the highly erotic and deeply ambivalent category of she-male. There was and is nothing feminine about Bentley. His masculinity is pure and aggressively obvious. His control over me is very similar to the control of a man over a female slave. The pleasures he seeks from me are the pleasures a man would demand from a woman, pleasures I give with a helpless willingness. This was not the case at first. He is strong and stern. Like Mistress Helen, he revels in dressing me in the most dainty and outrageously sissified costumes, in exaggerating my ultra-femininity through dress, gesture, movement and perverse discipline. Attired in pretty, amazingly intricate little girl frocks of Senso satin, sheer white tights and pink Mary Janes, my hair tied in a pretty pink silk ribbon, my mouth stopped by a phallic shaped dummy gag, my head imprisoned in a gorgeous Victorian bonnet, I find myself on my hosed knees before him, my silk-gloved hands bound tightly behind my back, my nylon-sheathed ankles also tightly tethered. I face his open legs, my bottom stinging from the hard merciless spanking he has just so expertly inflicted, and I watch with wide helplessly girlish eyes as he unzips his leather trousers and slips out his huge rock-hard cock. I squeal with pleasurable anticipation into my dummy gag and wiggle my tightly plugged bottom helplessly. I know tonight I will suck this fearsome sex weapon dry and then teasingly revive it so that I can be fucked senseless.
As I torment Pansy’s sex, I remember my times with Master Bentley and feel a quiver of deep dark excitement flow through my delicately sissified body.
‘I can’t wait for Taylor to see me with pretty bouncing titties,’ she whispers, pulling herself a little further onto the bed.
I smile gently and find myself thinking of her training master. Despite Bentley’s physical strength and his absolute authority over me, I have always felt a strange gentleness in him, even when I am bound and gagged and held firmly over his powerful thighs, my panties down around my knees, my pert wobbling backside receiving a sound and merciless spanking. With Taylor, however, I have seen nothing but the cool sadistic exercise of power. In Taylor’s ice-blue eyes there is the sheer pleasure of unquestioned control. An ex-American army captain, Taylor is tall, spectacularly muscular and frighteningly hard. On the face of it, he is merely the second training master, but over the last four weeks it has become clear that he plays a much wider role in the Bigger Picture. It is well known that his original association was with no less a personage than Eleanor Groves, the ex-wife of an ex-U.S. president, and one of the most famous women in the world. Through Ms Groves’s friendship with Lady Ashcroft, Taylor, who had been her personal bodyguard, came to work for SMC. His attraction to sissies is very clear. Yet, unlike Bentley, Taylor is also a servant of women. It is obvious that he acts as Mistress Helen’s personal bodyguard and almost as her butler. It has also become clear that he services the heterosexual mistresses, particularly Lady Ashcroft and the occasionally bi-sexual Mistress Anne. It is therefore perhaps surprising that he is far harsher on the sissies, and that poor Pansy certainly suffers at his hands.
As our lips meet again, I notice a thin red line running across Pansy’s left thigh, and I know this is a fading memory of the ivory-handled riding crop Taylor uses to punish and ‘inspire’ Pansy. I also know there are a lot more of these wicked lines crossing her perfectly formed bottom. I both pity and envy her. When I am in Bentley’s powerful arms, I am always aware of his absolute control, but I also know that he is essentially a professional dominant. To him, the rituals of punishment are associated endlessly with the giving and taking of pleasure. With Taylor, this has never been the case. His commitment to domination is therefore deeply political, driven by a belief in his power and the power of the Bigger Picture. It is detached from emotion, and therefore far more dangerous. And it is this danger that arouses me, and which very clearly arouses lovely Pansy, for her feelings for Taylor are obviously deep and intensely positive. And, despite his cruel demeanour and authoritarian manner, Taylor appears to reciprocate these feelings; for it has been made very clear to all the mistresses and housemaids that Pansy is very much the sole property of Taylor. She is not be taken by anyone, except him and, perhaps strangely, me. For some reason, it seems to amuse Taylor to know that his sissy slave has a pretty, eager sissy girlfriend, a role I fulfil with a helpless enthusiasm.
As I contemplate Pansy’s sensual welts and her blissful suffering, I can’t help thinking how unlucky (and thus how very lucky) she has been with her masters and mistresses. First there was Ms Hartley, the powerful, wicked and cruel guardian who took such a dreadfully dark pleasure in her role as the co-creator of the lovely helplessly sexy ultra-feminine Pansy. Then there is cruel sadistic Taylor. And, on top of this, we have Mistress Anne.
Mistress Anne, the co-founder of SMC, a gorgeous statuesque redhead who I have never seen in a dress or a skirt, yet, despite this, an intensely feminine and very beautiful woman. A little younger than Mistress Helen, with cool emerald-green eyes, she is a figure that inspires genuine fear in all the housemaids, male and female. Often dressed in beautiful light-coloured expensive silk trouser suits and very high-heeled leather boots, her naturally long orange-red hair tied in a tight bun, she has a well justified reputation for sadistically inventive punishments, a fiery lesbian temper and a considerable sexual appetite. Poor Pansy always returns from her regular ‘training sessions’ with Mistress Anne utterly exhausted, her poor sex inevitably battered by some dark penile torture, her arse spread wide by sinister intruders, her buttocks cherry-red from harsh prolonged spankings, her lips and tongue worn to sandpaper by her mistress’s insistence on constant oral pleasuring. Yes … poor Pansy is so lucky.
Then, of course, there are our sissy mentors. Here I am, without doubt, the luckiest sissy in the world. For my mentor is the stunning Christina, the very first sissy trained by Mistress Helen. I have been her helpless admirer ever since Aunt Jane allowed Pansy and me access to the SMC website and the Silken Slavery micro site. It is Christina who has been the gorgeous icon of SMC, who has so wondrously featured in all their teasing ultra-erotic web-based marketing, who is the star attraction of so many of their very high class video productions – elegant erotic films streamed on the web and also available to buy on video/DVD. It is she who has teased me so expertly to a full realisation of my true deeply masochistic sissy personality. Over the last four weeks, we have made gentle sissy love at least twelve times, and each time it has left me in a state of soul-washed bliss.
Gorgeous perfect Christina. The senior housemaid, the sissy wife of Mistress Donna (the third of the original founder members of SMC), a tall incredibly curvaceous brunette with dark-brown eyes and the body of an ultra sex-bomb. A spectacular fantasy figure made startling reality by the techniques of the SMC. Her long perfectly formed legs always tightly sealed in the sheerest sexiest hose, her 42-inch bust, so deliberately designed by SMC, a promise of my own future transformation – ultra-sensitive pale rose orbs of sissy perfection that I have kissed and suckled with privileged lips. Her own full ruby-red lips have slipped so softly and expertly around my own paradoxical manhood and teased me to a screaming, profoundly joyous orgasm on many occasions and I have sobbed my helpless gratitude into a multitude of inescapable and relentlessly kinky gags. To be like her is all I ask.
I think of being taken by Christina and I think of bondage. Every time she has taken me, she has ensured that I have been very tightly bound and gagged. Her visits are normally announced by the arrival of Annette, Mistress Anne’s personal maid, and Christina’s long-term sissy love. She is Pansy’s sissy mentor and, perhaps unsurprisingly given her mistress, a cruel redhead with an aloof superior manner. When Christina is about to visit, Annette arrives to remove Pansy to some dar
k and mutually arousing entertainment while I am so very willingly ravished. I am always ‘specially prepared’. I am already dressed in a suitably alluring sissy outfit, and it is only a matter of laying me out on the bed and then securing my arms and legs, inserting a pair of soiled panties deep inside my mouth and then taping them tightly in place. Then I am left wiggling and moaning, my cock always released from its cruel and deeply erotic restraint, ready for Christina’s kinky attentions. Then she arrives, in her splendid senior housemaid’s costume: a black Senso silk dress covered in an erotically elaborate design of sparkling black roses, whose subtle outlines are only clearly visible at one particular angle under the powerful light of our room. This dress appears painted to her fabulous body, its tight unforgiving journey over her incredible chest marked by a terribly erotic and real tension between discomfort and erotic embrace. Over the dress is secured a gorgeous white Senso silk lace-edged pinafore, with her name printed in elegant red letters across its chest. The pinafore is tied tightly in place with a huge sissy bow at the base of her spine. Beneath the very short dress is an ocean of layered frou-frou petticoating, through which a pair of lace be-frilled satin panties are clearly visible. Her legs are wrapped tightly in sheer black Senso nylon tights with narrow perfectly straight seams that trace an erotic pathway leading straight to her gloriously plump but also exquisitely shaped bottom. Her small girlish feet are elegantly imprisoned in sparkling black patent leather court shoes with striking five-inch heels. On the pointed toe of each elegant shoe is a small diamond rose. Her long thick jet-black hair is bound in a very tight perfectly formed bun held in place by a diamond clasp that is made up of letters that spell the word ‘Chrissie’. Fitted carefully to the top of this wondrous hair sculpture is a small lace-trimmed maid’s gap with two silk ribbon tails that run down the back of her head. Her lips are, as always, painted a deep cherry red and coated in a sparkling gloss that turns every smile into a sensual promise of forbidden pleasure. Around her perfect swan neck is tied a black velvet choker, with a blood red ruby centrepiece that exactly matches her shimmering teasing lips.
She looks down upon me with sex-fired honey-brown eyes, her envelopment in Senso ensuring that her gorgeous she-male body is trapped in a tight film of merciless sexual need. I moan helplessly into the fat panty gag filling my own sissy mouth, the taste of what I know by sweet experience is Mistress Helen’s cunt adding to this moment of pure erotic bliss. She smiles slightly and moves towards me with the elegant grace of an expertly trained sissy maid. I know that beneath the lovely dress is a further array of spectacularly restrictive femininity: a tight red and black whale-boned corset that holds her slender sissy waist within a cruel but incredibly exciting embrace, a delightful Senso silk brassiere that torments her ultra-sensitive and very large breasts, leaving her feeling as if her boobs are being teased by a hundred pairs of sissy lips every second of every hour of the day. And over all this, a short black silk petticoat, a teasing Christmas present from her own true love, Mistress Donna, the absolute empress of her body and soul.
I meet her stunning soul-melting gaze and squeal with a terrible girlish desperation into the gag. Her beautiful smile widens and she carefully sits down beside my tethered form on the bed, her short skirts rising as she does so to reveal a detailed glimpse of her gorgeous Senso silk panties, with the outline of her large tightly restrained cock clearly visible. During previous visits, it has been obvious the restrainer has been removed by Mistress Helen (the only person other than Mistress Donna allowed to do so), and that, as a consequence, I should expect to be fucked hard and long, a pleasure Christina has showed me is both explosively immediate and, given the right lover, darkly subtle. But today – the day that replays in my dreams – she has come to milk me, to indulge a passion for oral sex that is drilled into each sissy maid from the very first day free from the inducting pleasures of the Nursery. So, I am to be given a terrible profound pleasure and also give pleasure to one of my numerous sissy lovers. I moan with a feverish anticipation into the panty gag and await my glorious fate.
And now, as I prepare to slip my own carefully painted lips over Pansy’s hard hungry tool of love, I feel my own tethered sissified sex stretch angrily in its merciless rubber restrainer, held so tightly in place by the cruel cock rings, each marked with the black rose logo of the SMC, and know that I have reached the very edge of my true self; that I have taken a long strange journey from being the spoilt feminine ‘nephew’ of a beautiful, loving and very dominant Aunt to being a very pretty, soon be utterly convincing she-male slave bound and tightly gagged to a vast conspiracy of gorgeous, dominant and very powerful women. This journey has reached its final section. In the last four weeks, I have learnt to consolidate and develop the skills I began to learn under the watchful and expert eye of my Aunt. Possessed of a natural feminine grace, I have passed every deportment test with flying colours. As I wiggle-mince around the training chambers and private rooms of the SMC academy, my hosed knees and ankles never more than a few inches apart, my pert, shapely and very tightly pantied bottom wiggling helplessly beneath the sea of frou-frou petticoating, the eyes of my mistresses and the other maids are helplessly drawn to my perfect deeply erotic grace. As I walk in the highest of heels, my white nylon-sheathed thighs rubbing together, I wish so very very much I had breasts, and I so desperately look forward to the day when I will have them. I remember when Christina first revealed her perfect ample bosom to me and whispered her joy at their beauty and teasing sensitivity, then gasped with a pleasure I so very much wanted to be my own as I pressed my lips to each long hard nipple and sucked hungrily on her feminine perfection. Yes, breasts will be the final finishing touch to my intricate physical transformation. They will also provide me with the perfect counterpoint to the helplessly erotic gyrations of my bottom. Then, I will truly be able to walk like a woman.
Yet it is not just movement that has been learnt and perfected. The domestic skills taught under my Aunt’s exciting guidance have been very finely honed, and I am now an expert ironer, cleaner and washer. My deep transvestite fetishism has been a major learning tool in my significant expertise in feminine fashion. Always interested in the trappings of femininity – an interest expertly manipulated and developed by my Aunt – I now find myself in sole charge of Mistress Helen’s wardrobe, a wondrous privilege rather than a job, and Pansy and I, when not tightly gagged, spend much of our free time talking obsessively about the treasures contained in our mistresses’ wardrobes. We even have highly erotic conversations about the various types of panty gags we are forced to wear. Indeed, it was one such highly charged hoarsely whispered conversation that inspired our current bout of slow-burning furious lovemaking.
As I finally wrap my lips around Pansy’s hot hard twitching cock and taste her salty sweaty flesh, I know that I am almost deliriously happy, that, in my mistresses’ hands, I have become my true inescapable self. I think of the skills I have learnt, the skills of movement and servitude, and the sexual skills. Yes, these are all so much at the heart of the new personality that is Shelly. But they are only the parts of a greater whole, the work of sissy art that is the personality and body that I am becoming. And it is as I think of this work of art, that I think of Ms Blakemore, the School’s beautifully plump and gifted Matron, and the woman who, after my glorious, much-missed Aunt, I have come to most admire and who has, undoubtedly, had the biggest influence on me. As Pansy squeals with a volcanic wordless pleasure as I feel her cock expand to breaking point, I think of Ms Blakemore with the most affection and, without doubt, the most desire. For it is she who has taught me about the amazing entirety of my she-male self, the happiness of absolute submission to the Bigger Picture and thus the ecstasy of surrender to all womankind.
2
Ms Blakemore
AS PANSY’S CUM explodes into my mouth, as I taste the salty nectar of her darkest desire and swallow it with a now very familiar enthusiasm, I remember my days with Ms Blakemore. As poor Pansy squeals with uncontr
ollable and savage pleasure, the gorgeous ample form of Ms Blakemore fills my helplessly sissy mind, emerging from this whirlpool of memories like a black angel from a sea of sex.
She is probably no more than 35. Born on the island of Grenada, but brought up in the United States, she is a stunning Afro-Caribbean beauty, with milk-chocolate skin, large fiercely intelligent and very dark brown eyes, and full perfectly formed lips (always painted the darkest and bloodiest of reds). Her naturally straight hair is a shimmering jet, thick and long, but often tied in a tight bun. She is nearly six feet tall, and this helps balance what is undoubtedly a very plump physique. But in her ample frame are very apt proportions: broad strong hips, long surprisingly shapely legs, splendidly large but firm breasts and a beautiful if helplessly chubby face. A frame that is at its most striking in the erotic uniform of SMC Matron: a tight knee-length white dress with a button-up front, very sheer white nylon tights, and matching white patent leather court shoes with cruel and terribly exciting six-inch heels. A figure of startling maternal power, we were first introduced to her during the bizarre and delightfully kinky induction undertaken in the School’s wickedly erotic Nursery. Strangely, she had played only a slight part in our induction, the majority of the supervision having been undertaken by Christina and Annette. Yet as soon as I was out of Nursery and undergoing the early stages of my sissy maid training, I was summoned to her office, which was directly next door to the Nursery.
I had been working in the laundry room when Annette entered the large warm sweet-smelling room filled with washing machines, dryers and great piles of our mistresses’ clothing (which we care for with a helpless deeply fetishistic fascination) and told me that I was to report to Ms Blakemore immediately. As trained, I curtsied deeply before the gorgeous cruel-eyed redhead, who was already forming a very strong and sado-erotic bond with Pansy. I then followed her from the room and down the long hallway off which were the main underground sissy training facilities of the SMC academy, including the movement studio (where I had been taught further refinements to my sissy deportment by the very pretty, gentle-hearted Mistress Donna), the dressing and make-up training rooms (where Mistress Anne and Annette had been far less understanding), the classrooms (where we received lectures and instruction on the philosophy of the Bigger Picture and our role in the greater scheme of things), the kitchen and domestic training suite (where we were so ably instructed by Christina), the trainee maid quarters and the Nursery, the domain of the gorgeous Ms Blakemore.
Silken Servitude Page 2