Prince to Princess

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He arrived as a man...
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vanpan
vanpan
6 Followers

You arrive at the station and I meet you on the platform, we walk along the road to my flat. We are just chatting about nothing, knowing that there is an undercurrent of tension following our discussions and emails over the previous few weeks. I let us in and you follow me up the stairs. I take you round the flat so that you know the layout. You put your weekend bag in the bedroom.

I take you into the living room, you note that the curtains are closed although it is still daylight. I offer you a drink; having met you a few times now I know your preferences and we sit on separate sofas, sipping the drinks slowly.

I get up and, bending over you, kiss you deeply. I tell you to stay where you are and relax. I leave you and go to the back of the flat. You stretch back on the sofa, a sense of anticipation rising. Despite your many experiences, what we have planned is new to you and you are not sure how you are going to react.

You hear the bath water running and the floral scent of oils pervades the flat. I come back to you and hand you a package, it is the enema that I want you to use in preparation for what is to come. After a few moments I take you by the wrist and lead you to the bathroom. You close the door behind you to prepare yourself for me, empty yourself in readiness for my attentions. You call me when you are ready and I come into the bathroom. You are in the bath, the heady scent in the small room is almost overwhelming. You sink back into the water, allowing the heat to relax your muscles and I light the candles around the bath.

I sit next to you on the edge of the bath and sponge water over you, lathering the soap and gently rubbing you clean of the day. I lather your hair and massage it deeply, rinsing and applying sweet-smelling conditioner. You are carefully soaped all over, all the crevices and folds are attended to. I beckon you to stand and I reach for the fresh razor. Carefully, I remove all your bodily hair, from under your arms, your chest, all around your groin and down your legs, each stroke of the razor removing the years of maleness. When I am satisfied that you are smooth I beckon you to get out of the bath and wrap you in warm fluffy towels, drying you from head to toe. I reach for the bottle of body lotion and apply it to you, rubbing it into your smooth hairless body. It has a strong sweet smell and has a shimmer, giving your skin a glow in the candlelight. When I have finished, I encase you in a pale blue kimono wrap, tying the bandeau around your waist. Your cock is hard already and I can't resist leaning down to take you into my mouth, we both know though, that it is the last time you will have a hard on for a while to come.

I hold you by the cock and lead you into the dressing room. The curtains are drawn and there is a stool in the middle of the room, on the table is an array of feminine tools of beauty, cosmetics, hair implements brushes... There is also clothing hanging up on the curtain rail and a tooled leather bag on the floor.

I ask you to kneel in front of the stool, it is padded, a typical ladies dressing room piece. I push you forward so that you are leaning across the stool, facing the full length mirrors where you can see yourself. I lift the kimono so that your smooth soft arse is exposed. You still have a hard on and it is pushing against the silken fabric of the robe I reach to cup your balls from behind and squeeze them firmly. Dropping them, I move across the room slightly behind you but you can see me in the mirror. I pick something up and swiftly moving behind you, slip a blindfold over your eyes. As you realise what I am about to do, you take one last look at yourself in the mirror before being plunged into darkness.

I take one wrist then the other and hold them behind your back, fastening them together with something sturdy but comfortable, you can move your arms a little, enough to prevent too much stiffness. You feel me spread your buttocks and then the cool, cool feel of lubricant, softly massaging you and working in, first one finger, then two. I withdraw my fingers and you feel a hard replacement, pushing against your anus, opening it to take a plug, I gently push it past the first stage, as it goes in, the muscles clamp around it. I wait for a few minutes then push the second stage in, opening you wider and wider. When it is in as far as it will go, I run my hand over your buttocks and give you a smart smack, you start with the surprise which makes you clench around the plug. You squirm a little but settle again, waiting for my next move. I fold the kimono over your arse and rub the place where you were so recently smacked.

I take your shoulders and manoeuvre you to stand up, I tell you to stand where you are and you are like a statue, not knowing what I am going to do next. After a few minutes, your hard-on subsides as your mind wanders behind the blindfold. Suddenly you feel your cock and balls being restricted and bound so that a hard on would be impossible to achieve. The blood rushes to engorge but the tightness prevents erection. This is all part of the feminisation, no woman has a cock after all now do they?

I turn you around so that you sense that your back is to the mirrors. I push your shoulders to make you sit down on the stool, ensuring that your arse is over the back of the stool, allowing the plug to jut out over the edge. You are now bound, blindfold, restricted and waiting, silently, mouth slightly open and dry from the ragged breathing of anticipation. You hear me moving around, the wardrobe doors open and close, you sense that I am undressing. I take your chin and lift it, you feel my nipple in your mouth and you suck hard on it, groaning slightly as your hard-on tries to form. I pull back from you and then kiss your lips, brushing them and pushing my tongue into you whilst cupping the back of your head.

I go behind you and unclip your hands, moving them round to lay in your lap and then fasten them together again. You flex your shoulders and I gently knead them to relieve the tension. You hear me moving around again and you hear me dressing swiftly. There is the distinctive smell of leather in the air mixed with a sharp masculine scent.

I sit down in front of you and taking your hands, massage lotion into them, paying attention to your nails. I wipe your hands of excess lotion and start to manicure your nails. filing them smooth and pushing back the cuticles. You smell the acrid smell of nail polish and feel the coolness of the varnish being applied. You wonder what the colour is. I rest your hands back into your lap carefully to prevent smudging the polish and tell you not to move them.

I move to your feet and perform the same, massaging oil into your feet, finding the reflexology points and easing them away. You feel the same sensation of the cool polish being applied to your toes, again, wondering if they match your fingernails.

I leave you for a few minutes, you know I am in the kitchen by the clatter of pots and pans and you hear me go to the living room several times. You are floating slightly with the mixture of sensation deprivation and concentration focussing you on your cock, balls and anus.

I move behind you and motion you to stand. I remove the kimono and you are standing naked, your body shimmering with the body lotion. So beautiful to see. I hope that you are feeling as good as I am.

I lift your arms to shoulder height and you feel me put something around your chest, soft but with some firmness. I pull your arms down again to hold the garment in place. I start to fasten the garment, firstly putting straps over your shoulders and clipping them in place. You feel me pulling the garment tighter behind you and realise that I am lacing you up. Tighter and tighter the laces get, pulling you in and creating a waist. When I am satisfied, I move around to face you and ensure that your nipples are concealed, tucking them below the top. You feel me put something into the top, one side then the other, they press against your pectorals and you realise that they are meant to create a more female shape.

I make you sit down again and you feel me pick up one foot. I stretch something over your foot and unravel it up your leg to above your knee. I repeat this and then make you stand again while I clip the stockings to the garters dangling from basque that you have been laced into. I sit you down and repeat this, making you stand as I pull up the silky apricot-coloured french knickers, concealing your cock and the plug. The sheernees of the fabric outlines the restrictions that you have whilst concealing them from view.

I sit you down on the stool, you are disorientated by now and not sure whether you are facing the mirror or the closed curtains. The plug is still firmly in place but you have relaxed around it, feeling more comfortable with being impaled upon it.

I remove the blindfold, you blink for a moment and then become accustomed to the light. It is soft, candlelit and then you look down on yourself. You look so sensuous; now you appreciate the figure shaping that women choose and you admire the look of your legs in the sheer black stockings. You are surprised to see that you have some cleavage, not flowing over but there, shaped by the basque and the enhancements. Your deep red nails are a strange contrast.

I am dressed in black leather, jeans and a waistcoat, full breasts spilling out of the halterneck, still female but with my hair slicked back and just a light gloss on my lips. So different from the conservatively dressed women whom you last saw before you were blindfolded.

I brush your hair back, it is almost dry and I smooth it away from your face, holding it back with a towelling band. I tell you to close your eyes and spray on a facial spritzer. Then I smooth face cream on and gently dab it with cotton pads to remove the excess. I have cosmetics and brushes laid out and start to apply your make up. First the foundation and concealer, then I outline your lips with a pencil, filling in with a lipstick. Next is the eyeshadow and then I apply dark eyeliner to your top and bottom lids. Finishing with mascara, I dust some blusher to accentuate your cheekbones and complete with face powder. You are facing the mirror and have been watching the transformation intently. Lastly, I spray you with perfume to complete the feminisation.

Unclipping your hands, I slip a blood red jersey dress on you and smooth it down until I need you to stand up. As you stand, I shrug the dress over your hips and it falls to your ankles, The transformation is almost complete. I remove the towelling hairband and shake out a long brunette wig. I carefully put it on you, adjusting it so that the long curls tumble around your face. Neither of us can believe the difference and I can see your eyes glowing.

Finally I make you sit and slip high heeled shoes onto your feet, red and studded, spiked heels and with an ankle strap. You try to stand and for the first time, understand the awkwardness of stillettos. You take a step, the 4 inch heels altering your stance which in turn makes you clench more on the plug. The basque is holding you upright, breasts jutting out under the clinging jersey and line of the plug and cock restriction clearly visible beneath.

I take you by the hand and lead you through the flat, you hesitate as we reach the bedroom door but we continue to the living room. The table is laid for supper, I invite you to sit at the table, you carefully perch on the seat, due to the chair back, you cannot let your arse overhang so you are forced forward, pushing out your chest.

We eat, a light meal with just one glass of wine each and talk of the day, the bizarreness of the sexual situation in sharp contrast with the ordinariness of the meal. I pay you compliments on how you look and take the lead at the table, pouring your wine for you and ensuring that you are comfortable.

When the meal is finished, I clear away, you are my guest after all...

I come up behind you and kiss your neck, nuzzling beneath your long dark hair and biting you where your neck meets your torso, marking you lightly but avoiding your lips. I lift your long hair and twist it into a knot on top of your head. I run the fingers of one hand around your lips, prising them open, You feel something pressing against your mouth and suddenly you are gagged, I let your hair down and tie the soft gag behind your head. I take your hand to leave the table and lead you to the bedroom.

I order you to lie face down on the bed, the covers are pulled back now and there are pillows arranged across the middle of the bed. You lie down, the pillows forcing your arse high in the air displaying the plug. I tell you to spread your legs wide, the red shoes stark against the dark bed linen. You feel me fasten your ankles to the bed by your shoes and I give your arse a swift slap, not to damage but to sting. You cock is cushioned against the pillows, pushing up against you and still frustrated in it's binding.

I fasten your hands behind you again, you are helpless and I hear you whimper slightly through the gag. You are facing me and watch me sit in the chair in the corner of the room. I put my feet up and look at you, your hair tumbling around your face, make up a little smudged now but still heavy. The dress is clinging to you, the pillows forcing your hips up outlining the plug clearly.

Moving to the bed, I pull up the dress to expose you. I ease the plug out and stroke the inside of your thighs, massaging them and teasing you, moving nearer to your restrictions and watching your squirm. I tickle your perineum and push against it with my knuckles, sensing the shock of the additional stimulation flooding your body.

You watch as I remove my trousers and thong, I go to the bedside cabinet and take out a vibrator then move the chair nearer to the bed so that you can see me clearly. I put my legs on the edge of the bed and start to use my vibrator, slowly at first, moving it around my clitoris and then pushing it into me, I use it until I come, it is a quick release and you are fixated, watching the expressions on my face.

I lay the vibrator to one side and go to the cabinet, taking another one out, but differently shaped this time. I take your hands, releasing them only to spread them out to the sides of the bed and I fasten them to the frame. You watch as I slick lubricant on the vibe, realising that it is for you. I lift your dress and, parting your buttocks, push the slim end into you whilst pushing down on your lower back with my free hand. When it has reached the same diameter as the plug, I twist the end and it buzzes into action, sending you jerking with the feelings inside you. I tease you with it, beginning to move it in and out of you slowly, gradually increasing the speed of the vibration with the impetus in and out of you. You writhe against it, your arms and legs restricted, not totally immobilised but firmly restrained.

You try to call out but are muffled by the gag, I check that you are ok and put a soft ball into one of your hands, the way to communicate that you want to stop by dropping it.

I gradually reduce the vibrations, finally turning it off but leaving it in place. You watch dumbly as I reach under the bed to pick up my strap on. I fasten it around me, ensuring that the dildo is in place. I reach up to my breasts, still encased in their leather halterneck and feel them, you can see me pinching my nipples hard and your cock struggles against it's bindings again. I reach under the bed once more and take my clamps out, carefully fastening them to each breast, the clamps held firmly in place by the waistcoat. I tuck the control into the straps of the dildo and turn it on, a loud buzz fills the air and I gasp with the sensation. I play the remote button over my hips and around the strap on, stimulating my clitoris until I come again. You are fascinated, like an animal in the headlights.

Removing the vibrator, I unfasten your arms and legs. You stretch a little to ease your limbs and I tell you to turn onto your back, hips still on the pillows. I take your ankles, one by one and lift them above your head, shackling them to the bed head. Your arms are free but pinioned by your legs.

You watch as I lubricate the dildo and then I remove the clamps and lay them aside. I crawl onto the bed, whispering to you how fabulous you look and how I am going to fuck you until you scream with pleasure. I lift your thighs and spread more lubricant around your anus. It is still open from the plug and vibrator and I move to position myself for penetration. Slowly, gradually, I push the dildo into you, meeting no resistance now due to my earlier ministrations. I watch your face carefully, your blue eyes staring into mine, urging me on. I move faster, beginning to fuck you as a man would fuck a woman. I vary the pace, following your passion but wishing that I could feel you on me properly as a man does. You come due to the pressure on your prostate and the tears run down your face, streaking your mascara. I slow and gradually cease pumping, gently withdrawing from you and move up to caress your face. I release your gag and kiss your lipstick-smeared lips, licking the tears from your face.

I unclip your legs and arms and, removing my waistcoat, hold you against me, I take off the wig and smooth your hair in comfort.

We doze for a while, entwined while the passion subsides. When your heartrate has slowed, I lead you by the hand to the dressing room, I fetch some soft drinks for us both and then remove both your clothes and makeup. We are now man and woman except for the cock restraint. You tell me that you want to fuck me and take me by the hand, guiding it to the restraint and tell me to remove it. We go to the bathroom and shower together, soaping the sweat and lotions away.

We go back to the bedroom, you gesture for me to lie on the bed, you fasten the wrist restraints on me then clip them to each corner of the bedhead.......

vanpan
vanpan
6 Followers
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2 Comments
AnonymousAnonymousover 17 years ago
educational at the very least

this is exactly what my sissy wants done to him. thank you for providing me the information. it will be put to good use!

bullerbugbullerbugover 18 years ago
a good debut

never been into cross dressing but was able to see myself in the mans possition

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