Destination Unknown

Destination unknown – Sissy’s transformation

The house was in darkness as I arrived home that evening, just as I had hoped it would be. After all, a promise is a promise and I had waited so very long for this moment to arrive. All the same, I felt a shiver of anticipation as I fumbled with my key in the lock and let myself in, walking slowly towards the kitchen, almost closing my eyes as I entered the room.

My gaze fell upon the note, carefully left for me where I would see it. I knew what it contained already but, picking it up and scanning its contents, I could feel a wave of uncertainty whilst reading my instructions. Was this to be all I had hoped for or had I made a huge mistake? Too late to change my mind now I told myself firmly. Wheels were in motion that I could not stop now, no matter how nervous I felt.

The note was simply a list of what I should wear, where I should be and by what time and I smiled to myself. Mistress was always so precise, nothing left to chance, firm but never nasty, I loved her all the more for that. So accommodating yet ensuring her own needs were met in a way that ensured our privacy and our safety.

I knew this time was to be different, she had hinted at such during our previous conversations, but I trusted her entirely. Different would be good. It would be beneficial to us both and it would be within her clearly set boundaries. It would be exciting and I felt the beginnings of that excitement bubble up within me, butterflies in my stomach and a stirring down below that would have to wait to be explored.

I had work to do, preparations to make and very little time.

My clothing has been carefully laid out in the bedroom, a perfect outfit from top to toe. Masses of pink frills and a perfect petticoat containing the same, a vision in satin and lace. White knee socks with little pink ribbons adorning the tops and the shoes, oh those shoes, tiny ballet pumps in the same sweet satin pink as those ribbons. Pretty as a picture and the perfect look for a sissy girl, eager to please and ready to command.

I reached for the outfit and my gaze fell upon a box at the side of the bed. A present? For me? I reached down and lifted the lid. Layers of tissue paper filled the top with a small handwritten note which read 'If you so choose'.

My hands delved inside, careful not to spoil my present and I lifted out a pair of deep pink heels, the most beautiful shoes I had ever seen, in my size with a tiny pink bow on each toe.

I was in love. A gift from Mistress was not unusual but this gift was special, a change from my usual attire. I had to wear them, I couldn't take my eyes off those shoes as I carefully dressed, taking my time but knowing that my time alone was fast coming to an end and I had to be ready for her arrival. It was unthinkable, what would happen should I be late.

I stood before the mirror, admiring my new-found height in those beautiful heels, and slipped the straps of the bra over my shoulders, the silicon breasts moulding to my skin becoming one with my body, forgetting the time and smiling to myself. The rest could wait.

I should have known better. I could hear Mistress as she entered the house. Silent apart from the click clack of heels upon the floor and the bedroom door slowly creaked open. For a few brief seconds she looked me up and down then moved quickly towards me.

She didn't speak a single word but began to look me up and down. Breasts first, then the socks and heels. I felt stupid, pathetic, shivering in her presence and then it hit me. I had forgotten 'the device'!

Mistress let out a single sigh, disappointment? I was not sure. 'The other side' she commanded and I peered to the other side of the bed. To my horror I saw a second box. I had been so entranced by the shoes I hadn't even looked for anything else. My cheeks reddened. 'I'm sorry Mistress' was all I could manage to say as I reached for the box and placed it upon the bed.

She opened it and reached inside. Her hand pulled out a single item as her spare hand pulled me closer, closing her fingers upon my shoulder and squeezing gently as if to say it was all fine and that I had no need to worry. She was not disappointed in me, quite the opposite. I saw the hint of a smile as I raised my face.

Her fingers swiftly unfastened the device and she began to fit it to my tiny manhood. It was so tight as she pulled at the straps, flattening me entirely, preventing any chance of skin on skin contact or the hint of any excitement. A chastity device ensuring I was completely in her power fastened at the back with a long studded leather piece nestled in the crevice of my cheeks. It felt snug and I knew I was being prepared for something special as the colour matched the beautiful petticoats still laid upon the bed. This was no ordinary evening attire.

'Now, we must hurry, you will not keep my guests waiting'.

Guests? What on earth did that mean? A million thoughts flew through my head as she dressed me quickly, the dress over my head and smoothed over my hips, the breasts carefully in place, a slight bulge showing through the front of my petticoats and nothing but fading light to cover my shame.

My tiny encased cock tried to twitch, the excitement building but it could not move. I was denied that pleasure before we had even begun. The power was, as it should be, all hers to give or to deny.

Mistress turned away from me, reaching into the wardrobe and with my heels I could see slightly over her shoulder. A large suit bag was being unzipped and I gasped as I saw the contents. A deep pink hooded cloak, lined in sugar pink satin was removed and Mistress smiled as she turned back to me, placing the cloak around my shoulders and adding a small pink clutch bag to the look, my open hand grasping it tightly.

'Good, now follow me, say nothing and do as instructed. We are going out'.

Out? Dressed like this? What could that possibly mean? Out AND guests? My poor cock was straining, trying to break out of its leather clad restraint and failing miserably.

I nodded nervously and followed her through the door, down the hallway and out through the front door. Her car was parked in its usual place and darkness had fallen whilst I was getting ready.

'Door'.

That single word broke the spell and I rushed forward to open the driver’s door for her, knowing that I would not be allowed to drive and, besides, I had no idea where we would be going! She slid into the seat and I realised that she donned a cloak of her own, I had not even noticed that in the house. I had never seen it before.

Quickly I moved to the passenger side and let myself in, conscious that anyone might see me and not wanting to answer those questions I closed the door, thankful for the dark and the lack of street lighting by the house.

We sat in silence (mine uncomfortable due to the hard leather casing digging into my thigh and the buckled studded strap working it's way slowly into my arse) as she turned the key and began to drive.




With little else to do I began to gaze out of the passenger window, watching as familiar streets and neighbourhoods began to disappear whilst Mistress confidently drove. It was clear straight away that she was driving with a purpose and knew exactly where she was going, her hands caressing the wheel, coaxing the car around bends and corners in the darkness, never slowing but speeding us both towards her chosen destination.

I had time to think about all that she had said and our previous discussions before this night began. The mention of guests was no real surprise, although hearing her say it out loud had still given me a moment of nerves and hesitation and I tried desperately to recall everything we had talked about before in order to give me some advance warning of what might be about to occur.

Mistress spoke softly and I realised that she had been watching me.

'My sissy, you look confused, you are thinking too much. Do not be afraid, I will take good care of you as long as you please me and my friends. You want to please us don't you little one?'

'Yes Mistress, I give myself to you as always, I love you Mistress.'

'I know you do, and tonight you will have the opportunity to show me just how much you love me. You will do as I ask without hesitation yes?'

'I shall Mistress'

'Good. Now be silent, we are about to arrive. Be quiet, respectful and listen carefully to any instruction.'

I looked away once more and could see a large stately like house in the distance, lights blazing from the entrance, the rest in darkness. The car slowed and we pulled into the driveway. Not a soul in sight. We stopped and I heard the soft ticking of the engine as we sat in the darkness for a moment. I had no idea where we were only that I had never been here before.

I knew that I must move, I had to be the first to alight to enable me to open her door but it was harder than I thought it would be. The leather strap had dug deep between my cheeks now and my tiny little cock was squashed quite flat. I had begun to feel excited as Mistress spoke to me but all I could feel now was slight pain, my pleasure still denied. With difficulty I swung my heels from the car, softly closed the door behind me aware that Mistress detested loud noise and quickly made my way to the driver’s side where she sat patiently waiting for me to arrive.

My hands slightly shaking I fumbled for the handle in the dark and opened the door for her as expected.

She slid from the seat in one swift movement, towering over me in her own heels and smoothing the cloak around her shoulders before walking away towards the front door. I closed the car door quickly and tried to catch up but I was unaccustomed to my new shoes and stumbled, in the deep gravel underfoot, several times along the way before finally reaching the entrance, standing behind her as she produced a key from a small pocket in the lining of her cloak and unlocked the huge double wooden doors.

I was confused. I had expected this to be the home of one of her friends, how did Mistress have a key to this place? Where were we? I was soon to discover that this was no home in any traditional sense. This was far more. Almost a figment of some dark depraved imagination (mine or hers?) that could be both dream and nightmare. What it became was to be entirely dependent on me.

Stepping through the doorway gave me no clues. The place was in total darkness, the only illumination coming from two large windows on either side of the hallway showing a large staircase to the centre of the room and very little else.

I jumped slightly as the door swung shut behind me and I heard the key in the lock. No turning back now, I couldn't leave if I had wanted to and, if I was honest with myself, I had no intention of leaving this place without completing my Mistresses wishes whatever they may be. A tingle of excitement ran up my spine and as the leather pinched once more a small moan escaped from my mouth.

'Soon little one, quite soon. Follow me.'

Walking towards the staircase we began to climb, taking in everything around me, Mistress first, swift and sure footed as I continued to struggle in my heels. The frills of my dress the only sound, a faint rustling of satin petticoats as I silently followed and still, no sign of anyone else in the house. It was huge and I felt so small, so insignificant as I tried to keep up with the tall confident figure now reaching the first landing and continuing to stride towards the top, pausing there to allow me to finally reach her, out of breath and slightly panting. She was so patient with me and I could not wait to show my gratitude when the time came. I knew it must be close now.

She moved once more, walking across the landing and down into a darkened hallway beckoning me to follow and we finally reached another set of double doors.

Reaching forward and with a single push the doors swung wide open, no lock that I could see and I blinked as my eyes slowly adjusted to the light. What lay before me was the largest room I had ever seen, mainly in pitch black darkness with the exception of a single tall lamp positioned in the centre of the room. Under the lamp, carefully positioned was a stool. MY stool. But not as I had last seen it at all. It had been recovered in the same baby pink colour of the lining of my new cloak only in leather, the headrest underneath the same familiar black.

How it had been transported here I had no idea, but I did know what it meant and looking questioningly at Mistress the slight nod of her head and smile told me it was time. She reached to remove my cloak and I moved across the room slowly, knelt before the stool, then sat down upon the cold hard floor carefully adjusting my skirts before sliding, upon my back, underneath the stool and placing my head in the rest. I was thankful for my petticoats, protecting me from the worst of the cold, my socks warming my now exposed legs and my heels digging slightly into the floor whilst I waited for Mistress to make her next move and give me further instructions.

‘She is ready for you ladies, enjoy her, teach her but be gentle, it’s her first time but with your care and skill I doubt it will be her last’

My head snapped upwards, I had not seen anyone else in the room but my Mistress was talking to someone and slowly, out of the shadows, appeared the outline of others, all wearing cloaks like hers, walking with purpose towards the centre of the room, circling and surrounding me as they grew closer and closer with Mistress now positioning herself by my side. Dropping briefly to her knees she whispered in my ear ‘Please my friends, they will not hurt you. Please them all and you will find a new pleasure beyond your wildest imagination I promise you. Trust me, tonight you shall be reborn as the sissy girl you so long to be’.

Reaching downwards and slipping her hand underneath me she began to unbuckle the strap between my cheeks, stopping for only a second to run a finger the length of the crevice, my useless manhood now free and twitching at the feel of her touch and under the gaze of the others so very close to my body now waiting patiently for her to step away.

I counted seven figures around me, eight including my Mistress and watched in stunned silence as their cloaks dropped to the floor. There could be no doubt that these were real women, every one of them donning the most beautiful cocks of all shapes and sizes strapped around their waists, their ample breasts spilling over the leather corsets each of them wore. I wanted those breasts for myself, to be a real woman, matured and ripened as their bodies were as each stepped towards me, three of them lifting my back and arse off the floor and placing my own cloak underneath me, shielding me from the cold but giving me movement as the fabric slipped and slid around on the shiny wooden surface and they laid me carefully upon it. I realised then why the heels had been selected as a gift for me. They would be my only way of gripping the floor as the scene began to unfold before my shocked eyes.

I looked up once more as the first of the ladies sat herself above me and positioned her rounded buttocks directly above my face. This I was familiar with although not with a stranger and I knew what was expected of me as I opened my mouth, my tongue gently searching and probing for her most intimate area. Her position on the stool shifted and her tight little ass was pushed down upon my face, forcing my tongue inside. So dirty but so in need of both holes pleasuring I could hardly refuse her. I forgot the cold as warmth spread through my bones on realising that she was already damp, her juices flowing freely, onto my face as I serviced her ass, clearly turned on by the vision of me before her as she had approached. I wondered how long these beauties had been standing there, in the darkness, anticipating our arrival but all thoughts of that fled my mind as tongue and pussy connected, her movements pushing her down onto my face further, forcing my tongue to enter her entirely.

She began to rock gently upon the stool and I thought I would suffocate with the increase in pressure, all thoughts of the others blanked from my mind, the view I was giving them all, my exposed cock as my petticoats were pushed above my waist, a pathetic spectacle viewed, I was certain, with derision. Had they ever seen a sissy so small, so insignificant? Would I be good enough for them, for my Mistress? She did not allow me to enter her, only big swollen cocks were allowed that privilege, so I knew I had no hope of her friends allowing me that pleasure.

My face was becoming soaked as the woman above me lifted herself away and slid away, back into the darkness, another standing behind the stool and leaning forwards above me, her cock brushing against my nose and it was clear what she required. Once again, my mouth opened, and the huge silicon dick was forced further, inside my throat demanding to be sucked hard and deeply.

I was conflicted. I wanted to have those ladies’ voluptuous breasts, of course I did, I wanted to be a good sissy girl but this cock…If I had this my Mistress would allow me inside her, to pleasure and delight her. How could I suck so hard yet want to own such splendour? I could never be both girl and man. My role was to please so all I could do was as my Mistress wished. Service every friend, their pleasure to be my only focus, my only desire. I shut the thoughts down and concentrated hard on the cock inside me, licking, sucking, mouth fucking that huge swollen mass inside me.

Suddenly, I felt hands upon my ankles, holding me still as once more, my cheeks were lifted slightly from the floor, the cloak now used to move me, sliding me backwards, further under the stool, forcing the cock further into me and my shamefully small cock was being kissed, ever so gently but in a determined effort to make me hard. I did not know why that could be so important, I was not allowed to attempt to use it, I was banned from touching myself long ago, what ever could this mean? More mouths joined in, kissing me from my feet, feather like touches along the inside of my thighs, slowly working their way towards my balls, hanging as they were, two useless sacks of skin never allowed to empty, shrivelled against my leg sticky now with sweat. The feelings within me were forbidden, I was not allowed to cum! So much attention being paid to me, this was alien to me, my role was to please, not to be pleased and I began to panic. If I came Mistress would be furious, her friends disappointed, I would never be allowed to play again!

The cock inside my mouth exploded without warning, a jet of sticky liquid forcing me to swallow and, for a moment, my own cock was forgotten. A cock that came? Did all of the ladies have the same? How much would I be expected to swallow? I was snapped back into the mind of a sissy girl once more and in a brief second the cock was gone, replaced by another friend on the stool, another gleaming hole to lick, it was all moving so quickly!

I began to lose track of what was happening to me. How many women were around me, kissing, licking, polishing my tiny manhood whilst above my face positions kept changing, cocks thrust towards me, interchangeable and fluid, a pussy always waiting for me to service it while cocks swam in and out of my vision, all them cumming, that sticky feeling in my face, my hair, my throat then suddenly nothing.

Everyone stepped away, leaving me prone and vulnerable, my cock polished to perfection, brought so very close with every touch only to be denied at the crucial moment, on the edge of disobedience but never allowed to finish.

I was covered in sweat, cum dripping from my mouth, my lips sore, my tongue exhausted, my petticoats creased and wrinkled, gathered around my hips. My sissy breasts had been exposed, I didn’t know when or by whom during the mass gathering of hands upon my body and instinctively I knew that my role here was not yet over.

My Mistress stood towering over me, hands on hips gazing over my pathetic form, a slightly glazed expression in her eyes as she took in the scene of devastation before her and my pitiful appearance. There could be no denying that, although others were with her, she was still the only one truly in charge. She was the Queen, the others merely members of her royal court awaiting her instruction as I was myself.



With a slight nod of her head and a flick of her wrist a woman to her right handed her a box and removed the lid, taking a step back into the circle that surrounded me as it had in the beginning. My eyes widened as I saw what she held in her hands and finally she broke the silence, beginning to speak to me in hushed tones.

‘You have been satisfactory my little one, but it is not enough. My friends require more than you can offer in your current state. Like me, they will not accept your tiny meat as stiff as it is right now inside them, it can never fill them to capacity. We are real women, we need to be fulfilled. You cannot be allowed to use ‘that’ (she pointed at my sad stiffened cock), it simply will not do.

So, as you will never be enough, I have decided to help you. You will be big, strong, satisfying. We will make a man of you yet able to bring us penetrative pleasure. I shall make you huge, but never, ever will your useless, sorry looking tiny cock, touch me or my friends again’.

She approached me once more, her friends watching with eager eyes and knelt down at my side, the device that I could now clearly see in her hand as she lifted me once more, my back flat on the floor but my hips and legs raised, leaning over me and planting one single kiss goodbye on my manhood before reaching around to fasten the device in place. A huge black hollow silicon type cock, similar to one that I had admired so much as it entered my mouth earlier, carefully buckled at the back but this time, no strap between my cheeks. My own fit snuggly inside and I realised that I had been prepared for this. All of the attention given to me down there had hardened me to the point where I slid easily into this sheath, every tiny part of me enclosed within it’s centre. I could not be touched, kissed, licked, not an ounce of my genitalia could escape. It was a prison from which I could only give pleasure, never receive and I could not imagine how I would never cum again as a man. I was a student now of these ladies with cocks of their own, here to be taught their ways, to be schooled in the art of silicon fucking. My Mistress was my teacher as always, but these others were students too. They were to be taught how to enjoy a sissy slut to the maximum of their pleasure until they came, again and again. And I was to be their plaything in this lesson. Mistress had set me up to be the experiment none of us would ever forget. I was sure, however, that I would be the only one to be tested on my learning later, when this was over.

‘Be still and be quiet, I must check for myself before I allow my friends the pleasure’

She turned to face the circle and began to slowly squat, the curves of her beautiful bottom shielding my vision as she slid silently onto my new cock, taking its full length and sinking onto her knees. Every inch inside her as she slipped, in long measured movements up and down slowly, carefully, gripping the cloak and manoeuvring me as she rode that cock. I was inside her for the first time in such a long time but could feel nothing, the sheath denying me any human contact. All the same, the excitement was building within me and I remained rock hard, never filling the hollow space, that was quite impossible but fucking her in a way I had never dreamed possible since I began my transition into her sissy girl. My new transformation had begun, I was now her sissy lover, beyond all of my wildest dreams.

‘Place your hands upon my hips, do it now little one’.

I didn’t need to be told twice and my hands flew to her hips, pushing my bottom off the floor and bending my legs thanking myself over and over for choosing those heels as they dug down, preventing me from slipping and breaking the momentum as Mistress writhed and buckled, letting out an ear piercing scream that echoed through the room, all the time watched intently by her friends.

‘NOW’ she roared and two of them stepped forwards quickly, one rushing to the stool and fixing themselves above my face, the other standing in front of Mistress and she stood up in one swift movement and stepped to the side to allow her friend to take over, this time facing me and reaching for my hands, placing them upon her breasts as she lowered and slipped my cock inside her. She was far gentler than my Mistress and allowed me to touch her as she ground down upon me, my eyes unable to see as the dripping pussy above me forcing my tongue inside her and grinding down hard upon my face. I was blinded with passion and excitement as hands reached for me from all angles, my body electric whilst fingers and tongues probed in every crevice, hungry for their own turn with the sissy lover. It felt as though I would break apart being pushed and pulled in all directions and still, my useless cock twitched in a futile attempt to break free and be a part of the writhing mass of hands, pussies and cocks in a frenzied coupling between all of them and me. I was being used and abused in every way in that darkened room and I giggled in my head thinking of how pleasing this must look to the one that mattered the most, my darling, wonderful love and now lover, the Mistress of my Heart. How right she had been as always, the pleasure I was giving tonight was unlike any I had given before, it was an awakening, a reinvention of my own being. I was both man and girl, the two blending seamlessly into one and I thought my pleasure in tonight was finally complete.

‘Enough! Step back my friends and let your eyes feast upon your work, your creation. She is spent is she not? She thinks she is complete. What do you feel little one, could you take more? Is your transformation ended or only just begun? Do you have more pleasure to give?’


The women had once more returned to their circle surrounding me and I allowed myself a smile. She must be returning to me to take her place by my side once more. I nodded, ready to receive all that she had to offer her sissy, but she remained still. Her feet planted firmly on the floor, the cloak back in place around her shoulders.

I became aware of another presence in the room, a single hooded and cloaked figure silently approaching from the corner. Another lady to service before I was done? Why had she not joined the circle on my mistress’s earlier command? A watcher perhaps? Or documenting the evenings events?

The circle stepped back and melted into the shadows with the exception of two ladies who stood to the left and right this newcomer, their strap on cocks glistening as this mysterious stranger reached out and lubed them from a small bottle they had placed carefully on the floor in front of them. This was clearly not for everyone’s eyes but for My Mistress and her chosen ones alone. My nerves quickly returned at the sight. Lube could only mean one thing. And I saw three cocks before me including My lady love, the cloaked figure remained covered, I knew not what they could have hidden away for me. Mistress revealed her own cock, lubing it herself. Nobody was to touch her, no matter who they were it seemed.

‘Ready her’

Two ladies stepped forward once more, kneeling and placing their hands on my ankles, forcing my legs apart as Mistress reached down and removed the sheath exposing once more my tiny cock for a brief moment before placing me back in my chastity, the leather straps fastened loosely this time exposing my cheeks as my ankles and legs were lifted from the ground. Once more I was confined, pushed flat against my skin, restricting the erection I had so enjoyed. My cock, it seemed, was useless once more.

‘You know what she wants friends, what she needs, and you know your roles. She will not resist, you will show her no mercy. My very best friend will complete her transformation but before that time comes, prepare her well. I shall, as always, take my turn first. Remember, you may share her but she remains mine, always’.

My exposed cheeks felt the briefest drop of fluid as she kneeled between my legs, being forced wide open, and dripped lube along the top of my deepest darkest crevice. It ran, cold, down and dripped upon the floor and I shivered, a man no more as she gripped the cloak again sliding my hole towards her hard cock in one swift movement, teasing the rim with that huge bell-shaped end before plunging deep inside of me. My face was burning, the shame engulfed me quickly replaced by a new sensation, intense pleasure, as I realised what it felt to be a woman, to be fucked in my only hole, to no longer have the use of my own cock but to be used by others, my cheeks spread wide as she moved quickly in and out to begin with then slowing her pace as she realised I was enjoying this a little too much. Slowly she withdrew and spoke once more.

‘Not yet little one, you must be prepared for my final gift of tonight. You will remain in this position and my friends will enjoy you, but you must not experience orgasm until I feel it is time. Tonight, you will cum like a girl and every night from this evening onwards but not yet, no not yet, there is more for you to experience.

Take her’.

The hands around my ankles disappeared as she stood and watched, the others taking her place, all the time the hooded figure watching the scene unfold, their hands inside their cloak, moving silently, playing with her own cock perhaps, I could not tell, could not see as another huge cock slide inside my arse, stretched and soaked from it’s previous encounter, all hint of pain and shame gone as I forced myself upon it, wanting to be filled, knowing these cocks could cum as they had before in my face, needing to feel it dripping from me as only a woman would know. How long did they fuck me? Seconds became minutes, minutes felt like hours as I concentrated hard on stopping the electricity building inside me. I must not come, it was forbidden!

Only when three different cocks had forced their way inside me did it stop, a brief pause as the ladies stepped away, cum dripping down onto my cloak, my cheeks once again on the floor and still, the stranger stood there watching, waiting, saying nothing but noticing everything.

The ladies vanished back into the darkness from which they had arrived, only Mistress and the stranger remained staring intently between my legs, a strange smile upon her face. What did that smile mean? I had never seen her look at me that way before and I felt fear, not for the first time that night. What else was there for me, I had done all that had been asked of me and more!

The stranger looked at my Mistress and she nodded in approval, taking her place at my side, gripping my ankles as those had before her, lifting me as high as I could go and the cloak fell from the stranger in front of me. I had been wrong, so, so wrong, this was no lady! I began to squirm, to try and break away from the hands holding me but a look from her told me to stop. To trust her. I was still safe.

The huge black cock filled my vision as the tall muscular bull before me stepped forwards, between my legs, his magnificent manhood the largest I had ever seen.
Her best friend? No need to ask how or why, I could see for myself the attraction, the appeal that this real man held for her, but I had no time to think any further, to dwell on such thoughts.

‘She is yours, only for this moment. Fill her, make her cum, and you, my little one, time to become a true woman. Give the bull everything you have and more. Yes, he is big, intimidating even but you can take this. You know that don’t you darling’?

A final nod of my head told her that I would try, I don’t know why I nodded, I thought he may split me in two, I couldn’t take anything so big, so swollen! But yes, I would try, for her. Always for her and maybe for me too.

I held my breath as he probed between my cheeks with the tip, placing a finger on the rim and gently pushing it inside me, two fingers, then three as a moan escaped from my mouth before I could stop it. She was watching my every move as he withdrew his fingers, pausing, only for a second, before forcing himself into my gaping hole.

I had never known anything like it, the pain and then pleasure as I closed my eyes, letting every part of me go, the electricity building, my own cock forced against my skin and his, oh that glorious shaft, penetrating my every being. Tearing me almost in half, pushing against him and moving with him in rhythmic motion, as though I was truly only built for him and him alone. Showing me how little of a man I had ever been and how much more of a woman I had become.

My passion was finally unleashed as I drove him still deeper, warmth spreading from my thighs upwards towards my waist, my heels dangling in the air but my Mistress holding my ankles tight in her grip, never letting go, never letting me down. She had been right all along, I needed this, I wanted to be a woman, just in this single moment. I began to cum in waves racking my body with emotion and a single tear escaped, rolling down my face, spent at last in ways I never thought possible as he thrust inside me one final time, shooting hot wet cum I thought would never stop before sliding gently out, standing straight, replacing his cloak and turning, walking away, back into the darkness and out of my life. Leaving me on the floor, alone with my Mistress and speechless.

Every fibre of my being was exhausted, my vision blurred, the smell of sex lingering in the air and my legs were placed back down upon the floor where I lay for what seemed an eternity but must only have been moments.

I blinked, Mistress swimming back into view, smiling down at me with a look of pure delight. She reached down, smoothed my petticoats and made me decent once more and her hand reached towards mine helping me to my knees. I was too weak to yet stand.

‘Good girl, oh my obedient little sissy, you have done well – let’s get you home little one. It is late, and I need rest. Perhaps next time we shall stay but I promise you, you will always cum as a woman from this moment onwards, no more manhood for you’.

I saw the small tube in her other hand now, and I knew.

My chastity would be permanent but there were other ways, she had taught me that tonight.