It took fifteen precarious minutes for me to learn how to balance correctly on the three-inch heels, but once my aunt had instructed me in the secrets of feminine balance, I found myself mincing prettily around the room, wiggling my hips and backside, with my legs together, my arms at my side. I was a model of she-male grace that inspired amused but ultimately admiring comments from my clearly excited aunt.
Yet, despite my obvious feminine appearance, one thing remained distinctly male: my chest. The tight pink sweater only served to emphasise my maleness. Indeed, my aunt had made no attempt to purchase any form of brassiere, and now, in response to my slightly worried questioning, she reiterated her position on my she-male identity.
‘This is the way I want it to be, Shelly. You’re basically a sissy boy, a very pretty she-boy. That’s what I want, not a drag queen, not an imitation of a girl. You have your own unique identity, and that is what we’re going to develop.’
As I looked at my reflection, I saw her vision and couldn’t help but be aroused, a strange, deeply masochistic arousal that revelled in my sissification and its exposure in such an obvious and kinky form. And it was Shelly the she-boy who was developed over the coming months. Indeed, it wasn’t until I was sent to work for Mistress Helen and the wonderful Sissy Maids Company that there was ever any suggestion of a more fundamental alteration.
* * *
That first night as Shelly, I made my first somewhat tentative meal, closely supervised by Aunt Jane while wrapped tightly in a beautiful, befrilled silk pinafore. Rejoicing in each tiny, high-heeled step, overwhelmed by the beauty and sensuality of my feminine attire, I found a total peace, an almost unbearable sense of confidence in myself and my destiny. Each gesture was made to impress my aunt. To be displayed so erotically before her was a profound and deeply comforting pleasure, and I took a very naughty joy in bending down to pick up dropped cooking utensils and when setting the table, knowing that Aunt Jane’s eyes were pinned to my miniskirt as it slid up my shapely, nylon-encased thighs to reveal a hint of befrilled silk panties.
At bedtime, I was dressed in a gorgeous pink baby doll cut from an incredibly fine, expensive Italian silk, with new, matching silk panties. Aunt Jane laid me out on the bed, a heart-stopping, promising smile lighting up her gorgeous face, and ‘milked’ me with the same gentle care as the night before. And as I screamed out my pleasure and thanked my stunning goddess, I was truly in a she-male heaven on earth.
Two
The next few weeks set out the pattern of our new relationship and put me firmly on the road to my sissy destiny. Each day was swallowed up by a beautiful whirlwind of feminine attire and domestic servitude. It quickly became apparent that, as Shelly, I was to be both my aunt’s niece and her maid, and I took to both roles with a deeply erotic enthusiasm. My aunt taught me how to dress and how to care for my clothes, how to iron, to sew, to wash, to cook and to clean. She taught me how to move elegantly and how to apply make-up and perfume. Soon, I found myself working a solid eight-hour day around the house, and often working beyond this into the evenings. Yet never once did I question this new domestic servitude; for it was a willing servitude, a joyous slavery, and in it I found a freedom greater than any that I had ever experienced or read about. This was the freedom to be myself, to express the core of a being that had been long repressed by fear and social stigma.
After purchasing my new wardrobe, my aunt employed a hairdresser to visit our house and transform my short, blond hair into a mane of permanent sissy curls. A beautiful, ice blue-eyed blonde in her late twenties, with particularly large breasts and a cool, yet not unfriendly personality, the hairdresser was more than happy to produce the dainty, ultra-feminine style demanded by my aunt, asking no questions either of the reason behind this perhaps questionable feminisation or the fact that I was wearing a pretty pink satin trouser suit, a white silk blouse and high-heeled pumps! Indeed, it wasn’t until she had left and I had managed to recover from the intense humiliation that my presentation to her had created (a presentation I had begged my gorgeous, dark-eyed queen not to make), that my aunt explained the hairdresser had no idea I was a boy!
‘You can pass without trying, Shelly! Even with that delightfully boyish figure of yours.’
To be mistaken for a girl gave me a new, more powerful sense of happiness, and as my confidence grew so did my instinctive inner femininity.
Soon after the visit of the hairdresser, a firm of interior designers was employed by Aunt Jane to redesign my room, transforming it from a somewhat plain teenage boy’s den into a beautiful girl’s boudoir. Once the design was agreed, two burly, but friendly painters spent three days carefully painting the walls a delicious light pink, adding fresh white gloss paint to the woodwork and an intricate pattern of white roses around the top of each wall.
During their presence in the house, my aunt insisted I make regular trips to the room to serve tea, biscuits and sandwiches. Being dressed in a tight black nylon sweater, a knee-length black cotton skirt, black, seamed hose and heels was bad enough, but my aunt also insisted I wear a lovely French maid’s pinafore that was tied about my waist with a particularly large and dainty bow! As I minced before these two men, both of whom studied me with somewhat confused, yet also desiring eyes, I felt a truly wonderful sense of masochistic excitement. At first, I was utterly terrified, but when they returned my frightened, shy, humiliated gaze, all I could see was a fierce male need, no mocking, no contempt – just sexual attraction. Subsequently, I quickly took to the role of the coquettish teenage niece and began to enjoy the attention.
That evening, Aunt Jane took me in her arms and buried my face in her marvellous breasts.
‘The painters like you, Shelly.’
I moaned muffled agreement and felt my sex press angrily against its panty girdle prison.
As she released me, I looked up at her with sweet, decorated, baby-girl eyes. ‘They thought I was a girl. It was very…exciting.’
Aunt Jane laughed. ‘Oh no, Shelly. They know you’re a she-boy. I explained everything to them when they arrived.’
A gasp of horror exploded from my strawberry-painted lips and Aunt Jane burst into gentle, teasing laughter. ‘Never mind, I’m sure you can explain everything to them tomorrow.’
‘But…’
‘Yes, I want you to go up to them tomorrow and reveal everything. You must never be ashamed of who you are, my sweet.’
Even as I expressed significant resistance to this idea, I knew I would obey my aunt, that I would subject myself to this most abject humiliation. Why? Because my love prevented me from ever questioning gorgeous, imperial Aunt Jane. And also because, yet again, I found myself deeply excited by the thought of my own humiliation. And when Aunt Jane prepared me for bed in the spare room later that night, she quietly teased me a little further.
‘Did you like the way the men were looking at you, Shelly?’
‘Yes, Auntie. It was…strange, but also…exciting.’
‘Would you like a boyfriend?’
Her breath was hot against my face. She had just slipped the skirt off my nylon-sheathed legs and was preparing to pull my black silk panties down my thighs. She was dressed in a tight black nylon sweater that made her breasts appear even more spectacular, black silk slacks and very high-heeled ankle boots, her hair tied in a bun, her powerful musk perfume washing over me like a cloud of pure sex. Suddenly I felt a terrible giddiness and began to sway. She then helped me to the bed, concern suddenly crossing her lovely face.
‘What’s the matter?’ she asked, genuinely disturbed by my sudden faint.
‘It’s just what you said…it had an odd effect.’
She laughed and kissed my forehead. ‘I’m afraid you’re far too weak for a milking tonight, petal. So let’s just get you tucked up in bed as quickly as possible.’
The next day, she dressed me in a stunning pink frock with long puffed sleeves and a high, lace-frilled, button-up neck. The dress was one of a number of ‘little girl’ outfit
s she had bought for me over the last few days, and was very much part of her vision for her sissy she-boy. It was made from a gleaming, thick satin, and was very short. Over the dress was placed the dainty pinafore I had been made to wear the day before. My legs were encased in sheer white nylon tights and a pair of ultra-frilly panties were quite clearly visible beneath the short skirt. Finally, I was made to step into the pink patent leather, three-inch high-heeled mules. Suitably made up and perfumed, I was sent off to my bedroom armed with a tray of coffee and biscuits.
As I minced sweetly into the room, my heart pounding, a terrible mixture of terror and arousal driving me forward, I knew I couldn’t and wouldn’t let my aunt down.
The two men stared at me in amazement as I set the tray down before them. Then, in a surprisingly calm voice, I thanked them for the work they were doing and explained the reasoning behind it, making it very clear that I was a helplessly sissy she-boy who loved everything feminine and wanted only to be my aunt’s pretty, loving niece.
The men looked at me, utterly astonished, and for a few moments I was sure they would either beat me or flee the house. But instead, the older of the two then smiled and complimented me.
‘I’m sure you’ll make your auntie a very proud woman.’
I blushed and tried to avoid the teasing tone in his remark, the look of blatant desire in his eyes and the effect it was having on my already furious sex. As I minced prettily from the room, making every effort to wiggle by pantied backside provocatively, I suddenly found myself imagining being taken by these men, being held down and stripped, tied up and ravished on the floor of my bedroom; a violent homoerotic fantasy that stayed with me for the rest of the day, and rode the tidal wave of a truly titanic orgasm as my aunt finally milked me some fourteen hours later.
* * *
By the end of the Easter holidays, a matter of only three weeks, it would not be an exaggeration to say that the first stage of my sissification was complete. To celebrate my impending (and much-feared) return to school, and my aunt’s forty-fifth birthday, it was decided that we would throw a special party. At first I thought she wanted a party for just the two of us, but it soon became apparent that she wished to invite a number of her female friends! As the weeks had progressed, it is fair to say that not only had I become more confident and comfortable with my feminisation, but that my aunt had also become more assertive and dominant, a change that I accepted with joy and a proportional increase in my own natural submissiveness. And as she had become more confident in her clearly controlling role, she had begun to test my passive, even masochistic nature.
The first real test had been with the painters, and she had taken careful note of my excitement at this kinky humiliation. Since then she had slowly changed her approach to me. Over a few days, we moved from a gentle, loving aunt and sissy nephew relationship to something more akin to mistress and slave. Her requests became commands to be obeyed without question, and when I failed to perform to the standards she required, I found myself being very forcefully told off. This change was both deeply disturbing and very exciting, and I am sure she knew that the stricter she became with me, the more enthusiastically I served her. But the idea of the party…well, that was surely the biggest test. And when I protested, when I pleaded with tearful eyes about such a terribly obvious public exposure, she laughed and shook her head.
‘There’s no point in moaning, you silly little girl. My mind is made up. Now get back to work before I give you a good spanking.’
Her eyes burned into mine and I knew this was the beginning of a new phase in our relationship. The threat of a spanking sent a powerful, deeply arousing electric charge blistering through my body, and by the time I had minced back to my cleaning duties, I was as hard as a rock and having a little trouble breathing.
The day before the party, she insisted that I accompany her on a shopping trip into town – fully feminised! She woke me in my new, beautifully sissified bedroom and told me to be ready in thirty minutes. As I showered and shaved my already silken body, as I found what I thought was a suitably modest suit of grey silk, matching grey tights, a white silk blouse and modestly heeled shoes, as I carefully prepared my helplessly feminine face and combed my short, curled hair, a terrible fear tormented every thought to such a degree that eventually there was only one thought: my impending exposure as a pantied sissy in the middle of some dreadfully public thoroughfare. All the confidence I had built up in the last few weeks suddenly faded, a new, sickening terror gripped me. I looked in the mirror and saw not a shockingly pretty young woman, but a pathetic sissified male.
I carefully applied my make-up with shaky hands, affixed two pretty heart-shaped glass earrings to my girlish ears, and then minced downstairs. I presented myself to Aunt Jane. She expressed herself satisfied with my appearance, but also made it clear that I could have been a bit more ‘imaginative’.
After breakfast, she led me out to the car, my heart pounding, my whole body shaking with fear. Never in my life had I felt so terribly exposed. My mind raced with thoughts of impending mockery and even arrest: I would be recognised in the street, revealed as a panty-wearing gay boy and dragged off, high heels kicking in the air, to the local police station. But even as I had these terrifying thoughts, my cock was pressing angrily against the tight grip of its standard panty girdle prison and a simple thought was beginning to overwhelm all these complex, dark concerns: to be exposed in the street, to be carried off to prison by big strong policemen, to be locked in a cell with male criminals, dressed as I was – all this was so terribly erotic! And by the time my aunt parked the car behind the local shopping mall, I was more aroused than frightened.
Lost in this whirlpool of delightfully conflicting emotions, I was helped from the car and led across the parking lot, my heels clicking against the tarmac like bells sounding a particularly delicious doom. I walked with my now distinctive tiny steps, helplessly wiggling my pert, girdled bottom and distinctly boyish hips, my arms at my side, my hands slightly angled. An exaggerated walk, a ridiculously over-feminine walk that very publicly proclaimed my true sissy nature. Despite my fear, I was actually making it more easy for people to spot me, to realise that I was not a girl, but a simpering, mincing she-boy wrapped in silk and nylon! Yet this is how I had been taught to walk by my gorgeous aunt, and this was, I was sure, how she expected me to walk now – to demonstrate my true sissy nature to the world.
We spent over an hour in various grocery stores, including the local superstore, buying a vast array of expensive food and drink, and left the mall with a shopping trolley loaded to overflowing. During this time, there was little doubt that I was an object of confused fascination, receiving admiring looks from men and women, yet also looks of embarrassment and shock from those who understood what this pretty creature truly was. Yet not one harsh word, and certainly no legal intervention! Even when my aunt insisted that we visit a clothes store to buy hose and I was forced to present the pretty teenage assistant with five packs of nylon tights, the only comment was one of polite surprise, this despite the fact that my aunt, a cruel smile lighting up her beautiful face, made a point of referring to me as ‘he’ and stressing her relief that I could fit into the female sizes!
By the time we arrived back at the house, I was in a state of semi-elation and Aunt Jane was clearly very happy.
‘You handled that so well, Shelly. I’m proud of you.’
I thanked her and then spent the next hour unpacking the shopping.
That night, my aunt teased me to a furious orgasm and, afterwards, she spent a long time kissing and licking my flaccid sex, while also continuing to praise my performance during the shopping expedition. Over the last weeks of the holiday, my milkings had been limited to only one day out of two or three, and the urge to masturbate had ruined my sleep for at least the last three nights. However, my aunt, in her new dominant mode, had made it abundantly clear that any evidence of ‘fiddlings’ would see the complete cessation of the milking ritual, and th
is had been more than enough to persuade me to abstain from that particular vice.
As she left the room that night, she made a point of telling me how much she was looking forward to her birthday and hinted that I would be receiving a very special treat as part of the celebrations. As I lay in bed, confused, frightened, aroused, I pondered the forthcoming ordeal of my formal exposure to her female friends with a mixture of dread and intense, kinky sexual excitement.
* * *
The ‘treat’ was revealed early the next day. Unusually, my aunt insisted on supervising my bathing, dressing and make-up that morning. She woke me from a very deep sleep dressed in a semi-transparent silk blouse, a long, jet-black velvet skirt that reached down to her black-hosed ankles, and very high, stiletto-heeled court shoes of black patent leather. Her lips painted a glossy strawberry, her dark eyes filled with a strangely stern intent, she was every inch the imperious dominatrix, and it was very clear she expected me to be every inch her slave.
‘Wake up, Shelly!’ she snapped, pulling back the bed sheets to reveal my slight, sissy form enveloped in the gorgeous pink silk baby doll, my erection already very apparent through the teasing fabric of my matching pink silk panties.
I stared up at her in utter wonderment and then delicately extracted myself from the bed before following her to the bathroom. Here, she watched intently as I bathed and shaved, my sex hard and hungry as I carried out my morning ritual of preparation with what I hoped was my usual feminine care. A hint of a smile crossed her face as I climbed from the bath, a smile that widened as she then set about vigorously drying me with a large, very fluffy pink towel, smothering me in its erotic woollen embrace and her own powerful, tantalising perfume.
Once dried, she covered me in a cloud of baby powder, a new and odd twist to my morning preparations, before leading me back into the bedroom. Here I was made to wait for five tense, very frustrating minutes while Aunt Jane left the room to retrieve my ‘treat’. She returned with a very large pink box wrapped in matching silk ribbons. She placed the box on my bed, untied the ribbons and took from inside a new and very strange item of foundation wear: a pink elastane body girdle, complete with inbuilt rubber panels at the waist and a frightening array of silk ribbon lacing running up the back.
Company of Slaves Page 3
