Category: Transsexuals & Crossdressers Stories

Jemima's Tale Pt. 01

by jemimaheart©

An erotic tale from Jemima Cranshaw


Part 1 - Aftermath

I'm exhausted.

I'm still lying where he left me: half-naked, covered in sweat and face-down on my own living-room carpet. The wet patches under my thighs and stomach feel tight and sticky on my bare skin. The wool carpet is itchy against my right cheek and uncovered waist. The whole room seems to distinctly smell of sex - the sweet musk of sperm, to be more precise...

Sweat cools on my forehead as I gingerly move my left hand down, passing the damp limpness of my satiated prick, to reach under my raised left leg, with the aim of trying to gently sooth the dull ache that throbs between my buttocks.

There was no escaping the fact that I had been well and truly fucked...

Images of the previous few hours flit restlessly across my mind, strange memories of new feelings and sensations that I had never known before today. Never before have I had to face myself with the knowledge that my lips and hands and body had touched and caressed and sexually explored another man. That I had played the female for him, first performing intimate sexual acts for his pleasure, before finally letting him use me to satisfy his lust. Even now, half-undressed in frilly white lingerie, I was spread out across a carpet still damp with the evidence of our coupling - not only his semen but also my own.

My cheeks grow warm at the thought that only an hour ago people were walking past my front window - literally just feet away from the scene of my debasement. If their vision had managed to penetrate the obscuring white net curtains, they could have seen me in my full shameful glory: down on all fours in the middle of the floor, desperately thrusting my bare bottom for it was worth back into the groin of the naked blond man kneeling up behind me...

At this image, I once more feel the strong hands round my waist, holding me down firmly, brooking no escape from the stiff demands of his cock. With a remembered thrill of lust, my own prick once more complies obediently with my new-found role, stirring gently against my sticky thigh at my reawakening excitement (...I had let that man - that stranger - fuck me like I was a woman...) and I had loved it. All my unthinkable, long-buried desires had rushed to the surface and come tumbling out at last, clumsy and desperate with the strength of their need. There was no excuse left for me - no-one had forced me to accept his kisses or suck his prick, and neither had I been held down and raped - what I had done today, I had done willingly, unleashing all my hidden lustful fantasies of offering myself to a man to fulfil his every sexual need and desire. No longer could I pretend that my dressing up and my 'special sessions' were just a release of innocent fantasy; now I had exposed myself as someone who derived his greatest sexual excitement from actively playing the feminine role in bed. Gay, queer, homosexual - the words were probably true but my throbbing anus didn't care, it just knew the wonderful, panting, excitement that had come from being opened and stretched by a stiff, thrusting prick.

How long ago it seemed since all I knew was my old world, the solitary world of secret desires and unfulfilled longings...

Part 2 - Preparing for Pleasure

Inevitably, the day had dragged at work, and I was out of the office door and walking home, dead on leaving time. Even as I walked along the street, tempting pictures of the secret hoard that awaited me in the back of my bedroom wardrobe formed in my mind and I was glad that the length of my jacket obscured my burgeoning hard-on from the traffic.

Once home, I rushed upstairs, quickly stripped off my everyday clothing and went into the shower. When I emerged with smooth-shaven legs and behind, perfumed and talcum-powdered all over, it felt like I had finally rid myself of the day.

I went into the bedroom, opened the large mirrored wardrobe door and retrieved the innocent looking box labelled 'photocopy paper'. Inside, carefully folded and wrapped in tissues, numerous items of feminine apparel lay waiting to be enjoyed. Carefully I extracted my intended outfit for the evening and laid it out ritually on the bed: two white satin hair ribbons; a white satin choker; sheer white silk stockings with deep lace tops, pretty white lace strapless bra - full cup and expertly padded, a white satin baby-doll nightdress with matching frilly-backed pants; matching white satin suspender-belt, fingerless opera gloves in white lace; white leather stilettoes with 3-inch heels;

To complete the look, a pair of long clip-on silver earrings and matching ankle-bracelet.

Then I set out the necessary items to complete my fantasy session: a pink latex anal vibrator; a 7-inch long, flesh-coloured, dildo - shaped like a real phallus; jar of lubricant and box of tissues; a 12-inch metal ruler; four meter lengths of nylon cord...

My make-up box went on the dressing table, then I put my maids dress, basque, playsuits and other delights back in the box, restoring it to its hiding place in the wardrobe. I sat on the bed and selected the colour scheme for my lipstick and eyeshadow.

My reflection in the mirror watched as gradually normal everyday features became carefully transformed with an application of pale blue eyeshadow, a light touch of mascara and the drawing on of full, luscious, red lips. A hint of blusher to accent the cheekbones and an altogether more feminine reflection appeared in the mirror. This was Jemima - her open, inexperienced, features contrasting with the sparkle of intense longing and passion that shone in her seductively made-up eyes. She wanted to express her feelings and herself so much, but always, when she started to let go, their very nature and strength overwhelmed and frightened her. Only when she really could not stand it any longer, like today, would she allow her inner self out to satiate itself with a few precious hours of guilt and pleasure.

I took the ribbons and tied up my fair-brown, shoulder-length, hair into two cute schoolgirl bunches high up on my head. The lace choker went round my neck, tying at the back with a bow. The delicate material brushed my smoothly powdered chin and I pouted into the mirror, admiring the effect. My heart was already beating a little faster with the forbidden excitement of looking and acting like a girl. I reached for the nail-varnish, and sat naked on the bed, painting my fingers and toes crimson red, to match my lips. They dried quickly in the cool room.

At last it was time to get dressed.

Still sitting, I opened the packet of stockings and unfolded them from the cardboard. The late afternoon sun through the bedroom window gave them a luxurious pearl-like sheen. I took one, stretching it over my hand and gently rolling it up, then bent down to my freshly painted foot - always the right one first - and slid my toes into the weightless ring of silk. This moment always felt the same, seemingly significant or symbolic. I seemed to become slightly light-headed as I pulled the silk up over my heel, and beyond, watching and feeling first my calf, then knee and finally thigh gripped smoothly in a sheen of fine white silk. I repeated the process with the left stocking, pulling it high up my thigh to match its twin. A few inches above the lacy stocking-tops, my prick began to stir with familiar excitement.

I wrapped the lacy bra around my chest, reversing it so I could fasten it easily at the front. Sliding it round to the correct position gave me two beautifully curvaceous breasts.

Next I wrapped the white satin suspender belt around my waist, again securing it at the front then sliding it round. The front two suspenders attached easily; I stood up, the bedroom carpet caressing the soles of my stockinged feet, and turned putting first one foot, then the other, up on the bed, stretching each remaining suspender down under the curve of my buttocks until they gripped the back of the lace stocking-tops.

Instantly I became aroused, feeling the soft, elastic tug of the suspenders holding the silk hose firmly in place. My heart was beating faster as I reached for the panties. They felt like the softest thing I had ever touched, shiny and new, the many frills of white lace making them unexpectedly heavy in my hand. I bent and stepped into the elasticated leg holes. Pulling them up around my waist, I heard and felt the exquisite rasp of satin gliding over stockings and suspenders, then coolly clinging to my bare thighs until finally my buttocks and stiffened prick were deliciously encased in the taut, white garment.

It took seconds to bend and place my feet in the 4-inch heels of the stilettoes; a moment to secure the thin leather straps over and above my ankles. When I again stood the effect was amazing - the angle of the shoes pulling my silk-clad calves and thighs tight and sexy, my bum raised and pushed out invitingly.

Eager to complete my outfit, I pulled the matching white nightie over my head, adjusting the thin lace straps on my shoulders. The sheer satin fell down from the large bow below my bustline, reaching to mid-thigh. It was obviously designed to reveal a great deal of the wearers frilly-pantied bottom. The gloves slid up to cling to my upper arms, leaving red tipped fingers free to explore and caress...

I looked over my shoulder, to critically regard the overall effect in the mirror, and there was Jemima, all dressed to please in white satin and lace and waiting for her man to take her. Her enticing vision of feminine sexuality brought into contrast by the unmistakable male bulge nestling within the frill-backed panties, half-revealed by the shortie nightdress...

Part 3 - Satisfying Jemima

Quickly, I placed all my 'equipment' out on the left edge of the bed, removing the top from the jar of lube and laying out a big wad of tissues - in case of accidents...

Satisfied, I lay back on the edge of the bed, my stiletto heels resting deep into the pile of the bedroom carpet. I ran my right hand over my breasts and felt my nipples stiffen lazily beneath the satin and lace. Slowly, I slid my hand down to my satin-encased prick. For a while, I allowed one crimson-coated nail to draw slow sensuous circles of pleasure across the surface of the tautly pushed out material. Then letting it join its companions in firmly grasping the delightfully-imprisoned column, trapping it in a tight fistful of sheer, silky, underwear. They started to sliding the material up and down the swollen hardness, stroking it back and forth, back and forth, in a long, slow, universal rhythm of pleasure.

I closed my eyes and felt my excitement growing more urgent at the many sensations running through me. I began to push down with my feet, freeing my bottom to move up and down off the bedspread, as I masturbated myself through the satin panties.

Through the growing pleasure, I imagined it was someone else's hand - another man's hand - who was working my prick for me like this; imagine if he was trying to get me so aroused that I would do anything for him, let him do anything...

My heart started to beat faster, and I knew that I could deny the familiar, unsatisfied, craving no longer. I lowered my bottom back to the bed and, with a final caress of prick through panties, raised my legs up and back until my knees were over my waist. The points of my stilettoes pointed at the wardrobe mirror, and I looked down between my breasts, through my splayed thighs to see my reflection, lying on my back, legs spread and silken bottom displayed, a woman waiting anxiously for her lover to mount and take her.

I watched my right hand reach over my crotch, down to the seat of the panties, and deftly find the secret hollow hiding beneath its tight satin covering. Frills tickled my knuckles as I pressed, gently at first, then more firmly, pushing the satin against the opening bud of my anus. My legs quivered in the air. Still watching my reflection, I reached out, my left hand found the cool latex barrel of the vibrator. Deftly, I dipped the rounded end of the slender anal 'finger' into the cold-cream. Holding it practicedly between thumb and middle finger, I positioned my forefinger over the switch on the rear end. I put it between my legs.

With my other hand, I pulled the crotch of the panties to one side, displaying my bare anus to the mirror. I teased the eager sphincter with the smooth, lubricated tip of the vibrator, enjoying the glorious sensation of being widened and probed by the slippery head. A push with my forefinger and it slid easily inside, instantly filling my bottom with a warm, satisfying ache of fulfilment. (...ohh please - fill me with it - fill me with your hard cock...) My captive prick strained even harder against its satin enclosure.

The blunt end of the cylinder bumped against the hot flesh of my perineum. I clenched my muscles round the slender but firm invader, strangely proud that I had taken its entire 7 inches were up inside me. It felt so good and so right to be penetrated like this. I let my head rest back on the bedcovers, closed my eyes and switched the vibrator on.

A building sensation of pure, deeply-felt, pleasure buzzed through my entire lower body. In my mind, the sound of the small motor whirring in the still room merged with the grinding pulse of the latex cylinder buried between my legs until they were one and the same. Of their own volition, my hips shifted on the bed, while, helplessly, I reached into the panties and began to wank uncontrollably in time to the waves of noise that thrust and churned inside me. (...yess that's it - give it to me - oh god I can feel it...) My fingers trembled to the rhythm of the grinding latex cylinder; I pulled it out and pushed it back inside of me, giving my hot slippery anus the full benefit of the vibrations, my orgasm started to build, centred exquisitely at the dual core of anus and groin. It was too soon... to soon to fill the soft satin panties with cascades of creamy spunk.

Reluctantly, I pulled the vibrator out of me, switched it off and dropped it on the wad of tissues. My anus felt hot and scratchy, bereft of its welcome invader. I felt flushed and sexy. Sitting up, I turned to kneel up on the bed, desperate to continue and increase the sensations running through me.

I looked over my shoulder at my reflection and sensuously licked my crimsoned lips . I pushed my satin-clad rear out, making a show of ruffling the generous frills that covered it, before taking the waistband of the panties and starting to pull them down over the taut suspender straps. Inch by inch, the pale cheeks of my bottom were completely uncovered. I left the panties stretched tight across my thighs and with my right hand reached down to grasp the shiny metal of the 12-inch ruler.

Jemima was being very naughty and she deserved to be reminded her that such degrading, sluttish behaviour was not to be tolerated. I pressed the flat steel into the skin of my right buttock; appreciating the feeling of the cool metal. Gently I began to tap the ruler against my bottom, making the surface of the flesh vibrate slightly and causing a slight stinging feeling. Still very much aroused by my near-orgasm, I watched helplessly as my hand slapped harder, first one buttock, then the other, feeling myself enjoying the increasing tingling heat building in my cheeks. My knees shifted on the bed with the warm pleasure flooding through my behind. A glance in the mirror showed my flushed bottom taking its punishment like a man...

From under my nightdress, my unfettered prick strained excitedly out in front of me; I smacked harder and harder now, my whole rear flaming redder with each rhythmic slap of the ruler. (...Ahh show me that burning arse - yes that's right, show me how you love it...) Delirious with the combined sensations of stinging pain and ecstatic pleasure, I just wanted relief, to be fucked, to be dressed like a girl and made to come with my prick exploding and my hole filled up with a stiff cock...

Part 4 - Final Release

It was too much. My stomach felt sick with excitement and my thoughts were feverish with sexual images of release. Suddenly I knew what I would do; a special thing that I had previously devised. I would take my dildo and fuck myself from behind until I climaxed over the floor...

I threw the ruler aside and climbed off the bed. Pausing to feel the heat from my reddened buttocks, I carefully pulled the panties down to my ankles and stepped out of them: now nothing would get in the way. Grabbing the dildo, I exited the bedroom, the feeling of cool air moving across my body making me very aware of the gorgeous lingerie I wore.

It felt extremely naughty to go downstairs and enter the living room, in full daylight, made up and dressed to thrill in stockings and heels. The lace curtains prevented anyone seeing in, but the room still added to my arousal by making me feel daringly revealed. In front of me, under the window, I saw what I needed - the brown leather sofa. I caressed my stiff erection, reminding it of what was to come, and knelt down in front of the sofa

Years of feverish experimentation had led me to discover that it was possible to firmly wedge a long, cylindrical object between the tightly packed leather cushions of this sofa, in such a manner that it stuck out, strong and proud, waiting to be used as an instrument of desperate pleasure. Doggie-style, I would get on my hands and knees and, backing my eager bottom onto the rigid dildo, fuck myself deliciously from behind...

I pushed the end of the dildo into the dark crevice between cushion and armrest. By twisting it slightly, I ensured that it couldn't be pulled out - not even if gripped with the tightest of muscles...

I looked around. "Shit..." I said to myself. In my eagerness, I had left the jar of lube upstairs. I felt around between my bare buttocks and fingered my anus - still fairly moist from earlier attentions, but in need of a little extra help. (...oh well - nothing for it but to use the natural method...) Impatiently, I got down on my hands and knees in front of the protruding dildo, leant forwards and placed my lips over the realistic purple glans. Automatically, I closed my eyes and began to run my tongue around the head of the fake penis, making it nice and wet. It was the well-endowed prick of my lover that I took into my mouth, sucking him excitingly, making him ready to take me. Soon I would impale myself deliciously on this hard, thick, shaft, so the slippier it was, the easier it would slip inside...

"Fucking hell." said a quiet voice directly behind me.

Part 5 - Caught in the Act

My eyes snapped wide open. My mouth released the dildo and I looked over my shoulder with a gasp. There, standing in the doorway, was a tall blonde man staring open mouthed at the sight in front of him. How long had he been there? I couldn't move a muscle. I was completely, utterly, exposed: on all fours, dressed in sexy white lingerie, legs splayed wide, bare bottom in the air, and fellating a dildo for all I was worth. (...found out! - I've been found out!...) My secret was out.

I could not seem to think consciously. I remember that it felt like I was living to survive every next second and no more. My mind seemed to absorb the facts that he was well-built, late-30's, blue eyes and a fair moustache, wearing a green T-Shirt, jeans and sandals. Another impression was that this man seemed to possess a distinct bulge at the crotch area of his jeans. (...was it possible? - could he be...?)

"OOh..." I murmured tremulously and something deep inside me, deep inside Jemima, made me wriggle my bottom slightly in my distress. It must have been obvious to him that I was not a girl - for a start, I thought, feeling my face flush at the image, my balls would be visible to him, hanging below my naked bum-crack, but maybe something within him was responding to my explicit signals of sexual submission. My girlish make-up and hair, sexy white stockings and high heels, and particularly the smooth feminine buttocks openly displayed before him, could perhaps be providing enough female sexual signals for him to become aroused.

Category: Transsexuals & Crossdressers Stories