Like most crossdressers, for most of my adult life I have had the urge to dress-up as a woman
I have been home from work for over an hour; I lift my head from the brief that I have been reading by the light of a desk-lamp. The room is full of shadows. I look at the antique clock on the mantle and see it is approaching eight o’clock and I look over at the window; it is dark out. I close the file on my desk and then close the curtains in the study. I go from room to room closing all of the curtains, double checking to make sure there isn’t a chink or breach in any of the curtains that will allow anyone to peek inside my house.
My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite.
Like most crossdressers, for most of my adult life I have had the urge to dress-up as a woman for short periods of time, and I often used to dress in my wife's underwear when she was away on business. Since the divorce some two years ago, me, Michael, the respectable businessman, likes to transform into Michele, the sexy secretary (or naughty nurse; or whatever takes my fancy at the time) whenever it pleases me to do so. Living alone, and having the privacy to dress when it suits me, I have spent many hours developing the persona of Michele over the last two years. Of course I have to keep my secret life secret; and even though I have a strong desire to do so, I have never ventured out dressed as Michele.
I have acquired an extensive wardrobe, first at opportunity shops and then later at women’s clothing shops, insisting to the shopkeepers that I am buying the clothes as presents for my wife. Lingerie is easy to buy, as it is never considered unusual for a man to buy nice underwear for his wife or lover.
I bought my first pair of women's shoes from an opportunity shop, and once I had figured out my size in women’s shoes, I went ahead and purchased many styles of high-heeled pumps and sandals; again insisting to inquisitive shop assistants that they were presents for my wife. I sometimes even had the boxes gift-wrapped to maintain the façade.
I have experimented with wearing my wife's makeup with various degrees of success and failure during the years of my marriage. After she left me I obtained all the makeup I needed easily by purchasing a couple of complete makeup kits ("its for my niece's birthday; she's just turned thirteen" I told the shop assistant). I have added more cosmetics to this makeup collection by throwing any cosmetic item I desire in with the week's groceries when I’m out shopping. No one ever questions me at the checkout; husbands just pick up whatever their wives have written down for them on the shopping list after all.
It is easy to purchase women's jewellery of course, but my biggest problem was how to get my hands on some nice wigs. The problem was solved when I was sent by my firm interstate to Sydney on a business trip. I went to Paddy’s Market and there a sympathetic lady in a market stall that sold women’s wigs helped me pick out and try on three different wigs of varying styles and hair colourings. I purchased the wigs and then went up to Oxford Street where I went into a ‘specialty shop' and bought two pairs of breastforms in different sizes.
I love being Michele; I transform into her at every opportunity I get, and I spend most evenings and weekends dressed and fully made-up. I do not consider myself gay; in fact when I’m not dressed as Michele my sexual fantasies revolved around women; but when I’m dressed as Michele I often fantasise about being with a man or having a ‘lesbian' encounter with another transvestite.
I am terrified that my secret life will be exposed. When I am dressed I keep all of the doors locked, the shades closed and of course I never answer the door. Although I have become adept at applying makeup and dressing en-femme, and I believe that I make quite an attractive mature woman, I would never dream of going out dressed as Michele.
I read books and look at magazines and movies where transvestites have hot sexual encounters with each other and with male admirers. My favourite place to live out my fantasies is the Internet. I troll the chatrooms and cyber-space meeting places and I sometimes perform on webcam with other TVs and admires. I have been thinking a lot lately of either placing a discreet ad in a sex shop or advertising my availability in a contact magazine.
I check the time once more on the antique clock, and through the gloom I see that it is eight oh five. Now that I have finished working on my legal brief and the house has been made secure, I move towards my bedroom; my breathing quickening in anticipation. It’s time to transform into Michele and have some fun!
I strip off my clothes, shave my face closely and then take a long hot shower. I run my hands all over my chest, arms, legs and buttocks and am pleased to find them stubble-free. I fully shaved my body only two days previously and I used a hair-removal cream to remove all of the hair from the crevice of my behind and my scrotal sac. I can’t go to the beach like this, it would look suspicious being fully shaved. I also have to be careful at work, but working in a busy office where good grooming is expected, it is not unusual for a man to have the hairless ‘Metro’ look. The joke is that when my male work colleagues discuss fashion and the styles of the latest suits; I secretly wish I were dressed in the secretaries’ clothes rather than the latest business suit.
I dry myself off and sit at the dresser. I take my time applying foundation; it closely matches my skin colour and covers up the few blemishes that mark my face. I liberally coat my face and neck with face powder, one shade darker than my foundation; I now have the blank canvas on which to apply the rest of my cosmetics.
I apply eyeliner next, from the inner corner of my eyes to the outer corners, gradually thickening the line as I go. When I have thick black line running along the edge of my eyelashes I reach for my eyeshadow.
I select a pale blue which I apply to my eyelids and then blend it with a shade of dark pink which I brush onto the upper part of my eye sockets and right up to my eyebrows. Then I rouge my cheeks, defining my cheekbones. I like to use more eyeliner, rouge and eyeshadow than is the fashion nowadays. I like to imitate the makeup styles of the eighties rather than the current demure ‘less is more' look.
I apply a light coating of ‘skin-glow' face powder all over my face and neck to set the makeup and to give my face a subtle radiance. I carefully brush lashings of mascara onto my lower and upper eyelashes. I like to wear lots of mascara and have acquired a Maybelline product that does not clot and is relatively easy to apply.
I take my time applying my favourite Max Factor ‘Lasting Colour’ lipstick to my lips. I apply the base coat carefully just outside of my lip-line so that my lips appear fuller. I let the base coat set for a minute and then apply the clear topcoat over the ‘Raging Ruby’ lipstick and purse my lips.
I light a cigarette and concentrate while I paint plum red nail polish on my finger and toenails. Putting on two coats takes a few minutes but the effect is worth it. I keep my nails quite long and manicured; but this is another ‘Metro-sexual’ fad that is common among the men that I associate with at work and it does not attract attention. I stub out my cigarette and consider getting a drink. No, I decide I want to finish dressing first.
I study the three wigs sitting on their stands. I have a blonde shoulder-length, a black bob with cerulean highlights through it and my favourite brunette, with cerise highlights. I select the brunette and carefully lift it from the stand and brush it with my special wig brush. I admire the sheen of the artificial hair as I position the wig on my head and adjust it so that the fringe is straight and level with my eyebrows.
I open the bottom drawer in the dresser and there are my two pairs of breastforms. I take the smallest pair as I want a certain look tonight; more sophisticated then the bawdy size forty-two’s would permit. I affix them to my shaved chest with medical adhesive tape and cosmetic gum.
I open another drawer in the dresser and select a packet of flesh-toned sheer-to-the-waist pantyhose. I like to wear pantyhose as a foundation garment to help flatten my tummy, and to cover the small nicks and varicose veins on my forty-year-old thighs and ankles. I feel the first small tingle of excitement as I smooth the pantyhose up my legs and over my tummy and buttocks. I carefully arrange the toes of the hosiery around my painted toenails so that I don’t ladder them.
I stand up and walk over to my armoire. The armoire is an extravagance that I bought the week after my wife moved out and it is now filled with all of my female attire. For some reason I can’t mix my female clothing in with my male clothes. The built-in-robe that holds my boring business suits, shirts and dress shoes holds no interest for me tonight. Tonight I am totally absorbed with my armoire and the girly treasures contained inside its oak doors.
First I select some lingerie from a deep wooden drawer; the lingerie has acquired the delicate fragrance of the camphorwood drawer and I bring it to face and feel the sensuous satin on my skin and inhale the feint perfume. I place the lingerie I have selected to wear on my bed. My bed is a king-size four-poster with scarlet satin sheets and a black chintz comforter; another extravagance that I indulged in when the bitch left me.
I sit down on the bed and my pantyhose hiss as they rub on the comforter; little electric sparks shoot through my legs and my penis begins to swell inside the nylon sheath of my pantyhose. I push it between my legs and allow it to deflate so that I can continue dressing without an unsightly lump in my crotch.
I step into a white lace suspender belt that is fitted with three garter straps on each leg and then put on a matching white lace brassiere, adjusting my breastforms so that they fill the cups. I sit back down on the bed and slip a pair of taupe nylon stockings up my legs and adjust the dark back-seams so they were straight. I fix the dark welts of the stocking-tops to my suspender straps. My legs have a lovely sheen as they glisten in the lamplight; stockings worn over pantyhose give my legs a gossamer-like appearance and my red painted toenails peek through the sandal-toe-reinforced stockings. I run my hands up and down my legs enjoying the sensuous feel of the nylon but have to stop myself when my penis begins to rouse again.
I pull a pair of white satin full-cut panties up my legs and smooth them around my buttocks and over the suspender belt and then step into a peach coloured satin half-slip. The lace hem of the half-slip flutters against my stocking tops. The scintillating feel of the lingerie on my body arouses me further and I have to reach inside my panties and hose and adjust myself.
I walk back to the armoire and select a navy blue women’s business suit and lay it out on the bed. I step into the skirt and admire the single pleat at the front and the split side. It looks both professional and sexy, but it couldn’t really pass as a business suit because the hem only just covers my stocking-tops. I bought the suit off the rack at Carla Zampatti in Sydney and had the skirt adjusted at a tailor in Oxford Street who is probably the only man in Sydney that would dare to cut a hem that short on woman’s business suit. Of course he is used to the sort of clientele who make such requests.
I button myself into a peach coloured, long-sleeved, satin blouse and tuck it into the waistband of my skirt and close the zipper. I adjust the waistband of my skirt, and adjust the hem down over my slip. The skirt is tight around my buttocks and thighs and the hem sits high up on my legs.
I strut over to the armoire and select a pair of black high-heeled sandals and sit down at the dresser and pull them on, fastening the ankle straps. Nylon encased painted toenails peek from the black patent leather straps. I open another drawer and mooch among my jewellery collection. I slip a gold anklet on my right ankle and adjust it so that it falls below the strap and buckle of my high-heeled sandal. I clip on a pair of gold drop earrings; even ‘Metro’s’ aren’t getting around with both ears pierced so I have to make do with clip-ons. I put on an elegant gold ladies watch and two gold bangles on each of my wrists and a matching gold chain necklace around my neck.
I give my face another dusting of finishing powder and put another top-coat of lipstick on my lips. I spray my favourite perfume ‘Poison’ on my decolletage and spray a modest mist of the perfume under my skirt, a trick that I leaned watching my wife dress. I pick up the suit jacket off the bed and put it on and walk over to the full-length mirror that I also installed after my wife left, and make some small final adjustments to my wig, makeup and clothes.
I’ve got the look that I really like. The heavy eighties makeup, the subtly-streaked shoulder-length hair, the tight skirt, matching jacket and leg show make me look like one of the businesswomen or secretaries from work but only if they have the dress sense of a trollop. My skirt is way too short and tight and the side-split exposes my stocking tops. Yes I’ve got the look I really like, sophisticated but slutty!
I saunter into the lounge, my heels clicking on the tiles and my nylons swishing as my thighs rub together under my skirt. I take another look at the ornate clock on the mantle and note that it is now nine fifteen. I take some time to just stand there enjoy the pleasure of being Michele. The soft caress of my hair on my face, the feel of my satin and nylon underwear on my skin, the taste of my makeup, the scent of my perfume, the whole womanly feeling of being dressed sexy and sophisticated. I balance on my high-heels and then walk towards the kitchen to get myself that drink. The hem of my tight skirt clutches at my thighs, constricting my stride and I concentrate on stepping out, one high-heel in front of the other. My gait is sexy and I imaging how a man sitting on my lounge suite would see me.
A sexy sophisticate in a skirt that is way too short and heels that are much too high, wearing far much makeup; her buttocks swaying from side to side in her tight skirt, the back-seam of her nylon stockings leading his gaze down to her sexy black high-heels; that’s how he would see me.
"If only!" I chuckle to myself as I walk through the darkened room.
"If only what?" I hear a voice say from the corner of the room.
I spin around and look into the darkened room, half-believing that I am hearing things. The room is lit only by my desk-lamp; the drawn curtains have made the room gloomy, with thick shadows in the corners. I peer into the corner and see a dark shape sitting on one of my lounge chairs. He is dressed in a dark suit and I can see that he is a little heavy, his paunch hangs over his belt where his coat is open.
"What the fuck!" I whimper.
"Who the fuck are you, what are you doing here and how did you get in?" I hiss at the man.
"I’m Robert, I’m here to do whatever I want, and I used the spare key you hide under the second flower flowerpot from the left on your windowsill," he answered sarcastically.
"What the fuck do you mean do whatever you want? And what the fuck is a Robert?" I snapped back, putting on a false bravado.
"A Robert is the guy you chat with in the Trannyweb chat room you dumb cunt!" the man laughs.
"But I’m fed up with talking dirty with you on line and looking at you on your webcam. I’ve decided to come and get some of the real thing," he sniggers.
Of course, Robert is the name of one of the guys I chat with regularly on line; we have all sorts of cyber-sex and I know I have ‘performed’ for him a number of times on webcam. I realise that now that I’m a victim of my own on-line sexual proclivities.
The man stands up, grunting as he hauls his bulk out of the chair. I take my chance as he struggles to his feet; and I run towards my bedroom. I don’t stand a chance in my high-heels and tight skirt and the man sticks his foot in the doorjamb as I attempt to close the door and lock it on him. He pushes the door open and I stagger back and fall on the bed. He turns on the ceiling light, harshly illuminating the room.
"Ok Michele, we can do this the hard way or the easy way," Robert grins down at me as I sit on the bed looking away from him and staring demurely down at the floor.
Robert holds out a soft hand to me, his nails are clean and manicured. I take it in mine and stand up, shaking in anticipation with what is about to happen. Robert looks me over slowly with hungry eyes. He looks down at my black high-heeled sandals and follows my shapely; nylon encased legs to where they disappear inside the hem of my skirt. My stockings shimmer in the harsh light. His eyes continue up my suit, resting for a few seconds on my false breasts, pushing out the fabric of my satin blouse. He gazes into my face, his eyes engorging themselves on my full plum-red lips, my heavily mascaraed eyes, my rouged cheeks framed by my brunette hair.
"Fuck, you are ten times better in real life than on a webcam!" he groans and pulls me to him.
His tongue thrusts into my mouth as he crushes his lips against mine. He groans and his hand goes straight under my skirt and begins to brutally squeeze my buttocks through my satin panties. Robert pulls me closer, his breath is sweet and he has obviously just used a mouthwash. His rock hard penis is pushing against me though the fabric of his trousers and my skirt. He pushes me away from him releasing his grip and looks me up and down again with wanton lust.
"Lift yer skirt!" he demands.
"Whaaat?" I stammer, dazed and confused.
Slap! Robert's hand snakes out and he backhands me across my cheek.
"Lift yer fucking skirt Michele or I'll tear the fucking thing off you!" he shouts.
What can I do now? This guy has me trapped in my own home. Even if I scream and shout to attract attention I couldn’t live with the humiliation of my neighbours knowing I’m a crossdresser. My firm might find out! My fucking bitch wife might find out!!!
I look down at the man’s feet and I take the hem of my skirt in both hands and slowly raise it up my thighs. Robert's eyes follow the hem and open wide as my firm thighs encased in the sheer pantyhose, and then the darker welts of my stocking tops, slowly come into view. He gasps as the first glimpse of my white satin panties becomes exposed and he reaches out and strokes his hand up and down by thighs; his smooth hand slithering over my diaphanous nylons.
"Oh fuck, you're just like I dreamed you would be; I can't wait any longer!" he groans.
Robert grabs me roughly and spins me around so that I am facing the bed. He pushes down on my shoulders and I fall forward, doubled over so I that am tottering on my heels with my weight supported by my outstretched hands on the bed. I hear a ripping sound that can only be the zipper of his fly being pulled down. Inside I am feeling trepidation and apprehension.
Robert lifts my skirt up and pushes it over my back so that my silky buttocks are exposed; my rear is pushed up at him as I struggle to keep my balance. Then I feel a hot iron bar pushing against my panties; he rubs it all over my panty-clad buttocks. I realised the hot iron bar is Roberts's erect penis. His erection slides under the silken gusset of my panties and wedge’s itself in the crack of my buttocks between my panty gusset and my pantyhose. He rubs his swollen member back and forth inside the silken sheath, groaning and panting.
"Oh fuck that feels good," he moans.
I realise that Robert is receiving tremendous pleasure, dry humping my nylon encased arse and I also realise I can probably help get him off quickly. I push back against him and lift one hand off the bed and reach behind and stroke his cock through the slick panty material. Robert must be finding it even more arousing, my red-painted fingernails raking his glans through my silken panties. He continues to groan and push against my backside but then he stops suddenly.
"Oh no you don’t you fucking tranny whore! I know what you’re trying to do!" he shouts and pushes me in the back so that I fall on the bed.
I lie face-down on the bed and hear him rummaging around in my dresser. Then he stomps back to the bed and flips me over onto my back. Robert is very strong I realise. Then I look at what he is holding in his hand; he has a bunch of my pantyhose.
"Spread out bitch!" he demands; and suddenly I know where he is going with this.
"No! No! No! No! Pulllleeesssee!!!" I beg of him and try to sit up.
"Get down on the bed you fucking whore!" he grunts and pushes me back down on the bed.
Robert falls on top of me pinning me with his weight. As much as I try to struggle I can’t fight him and I end up tied to the four-poster bed, my wrists and ankles stretching at the pantyhose that tie me to the bedposts. I can move my arms and legs a little because Robert has tied me by the wrists and ankles to the four bedposts using four pair of pantyhose. But although I have some freedom of movement, I am well and truly fastened to the bed by the nylon ligatures.
Robert sits on the bed and takes his time getting undressed. He neatly folds the trousers of his suit and lays them over the back of my dresser chair and hangs his shirt and jacket there as well. He turns around when he is finally fully naked and I see his tumescent penis poking straight out from under his pot belly. It is long, thick and swollen; his glans is shiny and purple, a thin string of pre-seminal fluid drools from the eye.
He walks over to the bed and without any warning just drops himself on top of me. I am pinned under his weight and the bed sags appreciatively. He raises himself up over me and lowers his face to mine, breathing in my perfume.
"Oh fuck this feels so good," he whispers and pushes his lips against mine.
He is wearing after-shave and deodorant and I taste mouthwash as he slips his tongue into my mouth. At least he is a considerate molester I think to myself.
Robert kisses me passionately, his lips pressed hard against mine, his tongue explores under mine then slowly works its way around my mouth, flicking and probing. His body is hard against me and his hand slides under my back and lifts me off the bed slightly, it comes to rest on my buttocks. He rubs his hand there, the material of my dress and half-slip whispering against my panties and hose.
"Mmmm," Robert whimpers, his lips still against mine.
I lie still, neither encouraging him or denying him what he wants.
"God I just have to have you hun, my lovely transvestite webcam queen; this is just how I imagined it would be!"
Robert kisses me again as his other hand slides down and seizes both of my buttocks. He lifts the hem of my business suit skirt and caresses my half-slip. His hands work in a circular motion in time with his tongue, rubbing the silky slip against my tight panties. I now realise that he is gyrating his hips against mine; pulling the lower half of my body against his as his passion intensifies.
I lie still forcing myself not to move, to just take what is coming.
Using the utmost self-control I force myself to go limp in his arms again and allow him to grind his body against mine. His erection pushes against my stomach. I can feel the heat of it though the material of my skirt and slip.
Robert gyrates against me, his tongue working feverishly in my mouth, his lips crushing mine. The hands on my arse paw at my buttocks and pull my lower body harder against him. He is 'dry humping' me; pushing his erect member against me through my clothes. I perceive a deep humming deep down in his throat and he begins to breathe heavily as he continues to kiss me deeply.
Robert reaches a hand between our bodies and adjusts his penis, then his hand flies back to my arse and he rucks up my skirt and uses both hands to caress my buttocks through my slip as he pulls me back against him.
He grinds himself against me, his cock hard against my lower abdomen. I can feel the girth of it though the layers of slip, panties and pantyhose. I concentrate harder on not responding in any way and just allowing Robert to do what he wants to.
Roberts kisses are a hard insistent invasion of my mouth; every few seconds he has to break to take a breath; I can taste my lipstick and makeup. During these little gasps for breath he pants and moans utterances.
"Yes! oh yes baby! so good! so good!!!"
"Gotta do it soon! gotta do it soon!!!"
Robert reaches down again and struggles with his erection and he pushes it down then releases it so that it springs forward and at the same time he forces my legs open.
His cock is now wedged between my legs; encased in the silky sheer material of my half-slip, hard against my crotch.
"Oh my god!" Robert groans and begins to hump against me.
He gets into rhythm, dry fucking me in time with his feverish kisses; slowly circling his manhood against my body. Robert tugs on my slip and I feel it drag down my thighs until it is around the tops of my knees. Now I can feel his turgid penis trapped between my pantied crotch and gossamer cloaked thighs. Robert pushes against me and thrusts his cock into the silken trap made by my pantyhosed thighs and nylon panty crotch. I can feel the head of his penis rubbing itself along mine through my panties; my penis held in place tight between my legs by the gusset of my pantyhose.
Robert quickens his pace and his cock begins to throb. He pushes against me harder and holds me so tight that I’m afraid he will squeeze the breath out of me. His tongue is now a wild wet animal, thrashing in my mouth, fluttering and exploring every crevice.
Both his hands clench my buttocks squeezing them roughly through my panties as he pushes me down into the mattress to the rhythm of his thrusts. He groans and grasps my arse so tight that I am worried he will tear through my panties and pantyhose. He pulls me hard against him and I feel his penis begin to pulse and throb. Then he quickly pulls himself away from me.
"No, no, no, no, you fucking don’t! I’m not falling for that; I want the real thing!" he gasps, his body shuddering as he concentrates on preventing his orgasm.
Robert rests for a minute, pulls my slip back up and then moves from between my legs and moves further up the bed kneeling with his crotch level with my face. His hard cock wobbles in front of my eyes.
"Touch it!" he orders.
I reach out with my right hand, only slightly encumbered by the pantyhose binding it to the bedpost, and I gently stroke his turgid member with my fingertips.
Robert leans back slightly so that he can see my painted nails trailing along his shaft as I wank him. A thin thread of shimmering clear pre-come runs from the purple head of his penis and drips onto my satin sheets. He reaches out and caresses my thighs and stocking tops and then works his way up to my panties. I stiffen as I feel his hand go inside my panties and begin to fumble about. I force myself to relax and he eventually finds my thin soft cock nestled in the crotch of my satin panties and he begins to free it from its little prison.
I concentrate on slowly masturbating him to the best of my ability. I grasp his member tightly and slowly squeeze and then flutter my fingers against the shaft as I work my hand up and down his penis. He is obviously enjoying it because he is just staring at my hand wanking him while his hand strokes my stocking tops. His other hand finally frees my member, he begins to squeeze it harder and harder.
I stroke his cock with firmer faster strokes. He lowers his head and kisses me, gently sliding his tongue along my gums, exploring my mouth. Then he sits back on his haunches again and removes his hand from inside my panties.
Robert reaches out and puts his hands on my shoulders and turns me sideways on the bed. He draws himself closer and takes my head in his hands and pushes his crotch forward so that the head of his cock is between my lipsticked lips. He keeps pushing until I open my mouth. The musky smell of his loins is mingled with the faint odour of body lotion or talc.
"You take this bitch, and don't bite or you're fucking dead!" he laughs.
He pushes his sleek hard manhood into my mouth until I start to gag and then he commences fucking my face. He thrusts his sleek skinned penis in and out of my mouth. Underlying the taste of his body lotion there is also a sweet salty taste that I know to be pre-seminal fluid. My gag reflex remains suppressed as long as he doesn’t drive his cock too deep into my throat, and I can tell that he is very aware of this because he is obviously holding himself back.
I breath through my nose to compensate for the thick member filling my mouth. Robert tightens his grip on my head and eases his cock purposely in and out of my mouth. He pulls it back until my lips circle his purple glans and then thrusts forward, forcing his turgid meat deeper into my mouth. I move my tongue around the shaft and can sense his enjoyment. Robert is moaning and grunting with pleasure.
"Yeah you bitch whore, take this!"
"Take it bitch, take it!" Robert howls as his pleasure nears climax.
Robert quickly pulls his penis from my mouth and sits back on his haunches again.
"Nearly lost it again. As much as I’d love to fill your pretty face with spunk I have other plans," he pants.
Robert rests for a minute or two, occasionally reaching down to kiss me passionately to keep himself aroused, but being careful not to drive himself over the brink.
Robert stands and moves back down to the bottom of the bed. He jams two pillows under the small of my back, lifting my lower body off the bed. He rucks my skirt and slip back up around my waist and pulls my legs apart and then lifts my high-heels high up off the bed. He sits on his haunches between my outstretched legs, my nylon-sheathed legs are held open by the bonds tied around my ankles, my gleaming black high-heels held high. My heavy makeup is smeared from Robert’s kisses and sweaty passion, my damp hair is strewn around the pillow framing my face. We are both panting.
Robert positions himself further up the bed so that his member rubs against my panty crotch. He reaches out and pulls the gusset of my panties to one side exposing the crevice of my arse now protected only by the gossamer thin veil of my pantyhose.
I know what is coming and instinctively I try to push myself down into the mattress and away from the invading member but Robert takes hold of my waist and digs his hands into me to hold me steady.
"Oh no you don't Michele; hold still while I tends to my needs, it will all be over soon" he hisses.
His hard cock rubs against the thin gauzy nylon of my pantyhose and pushes the silky material into the crevice of my arse. Then Robert adjusts his member so that his glans is nestled against the bud of my sphincter. I feel Robert pull the gusset of my panties further across my buttocks so that he has an unobstructed view of his penis poised at my rear entrance; his erect member pushes the nylon of my pantyhose tight against my sphincter. He says something.
"Don’t forget the lube!" he whispers.
"Whaat?" I stammer.
"I think you will appreciate some lube about now Michele!" he says.
I reached under the pillow; my hand hampered by the bondage of the pantyhose tying it to the bedpost. I search for the tube of lube that I have put there previously this evening in anticipation of girly fun. I grasp it and hold it out to him.
"No, you do it Michele," Robert laughs.
He takes the tube of KY jelly and squeezes a big blob of the cool slippery liquid into my hand.
"You do it! And be nice and gentle I don't want to come before I get it in you!"
I stretch my hand down to Robert’s engorged manhood. It is rock hard and I put my hand around it, it feels enormous and menacing, throbbing in my hand. Robert looks down to see me lying there with my legs wide apart, my high-heels held high in the air, my legs encased in my diaphanous nylons with my white satin panties pushed to one side of my arse, exposing my buttocks. He watches as my long delicate fingers, their red painted nails glimmering with the shine of the lubricant, slide feather-like up and down his hard cock, coating it with a generous amount of KY jelly.
"Oh Michele, you're going to get it now!" he moans.
His hands move to my hips and I can feel his now well-lubricated glans pressing against my sphincter. But there is something preventing his entry; the nylon gusset of my pantyhose! He hasn't pulled my pantyhose down or torn a hole in them!
"Pantyhose!" I gasp.
"Yes, I love them!" he exclaims and thrust his hips forward.
The head of his penis slides inside my tight hole, the lube assists his entry but the nylon gusset of my sheer-to-the-waist pantyhose is also pushed inside me. The pain of having Robert's hard cock pushing inside my sphincter is bad enough but the nylon wrapped around the head of his cock is like fine sandpaper against the walls of my rectum.
"Oh God!" I groan in agony and then I look sideways to see myself reflected in a full-length wall-mounted mirror.
I am impaled on the head of Roberts's cock as I lie there with my legs spread, skirt hitched up and Roberts's gut hanging over me as he thrusts harder. His eyes close in concentration and ecstasy as he stuffs more of his tumescent member inside me. My pantyhose grow tight around my buttocks and between my groin as Robert forces more of the sheer fabric further inside me. He groans and holds me so tight that the pain is almost more than I can bear; I feel a searing heat as my insides are invaded.
Suddenly the flimsy nylon rips and Roberts's well-lubricated shaft drives itself all the way inside me as the resisting pantyhose gusset tears away. His cock is so big, and so deep inside me, that it knocks the wind out of me. I feel Robert's thighs against mine, his skin whispering on my nyloned legs as he grinds into me. His large gut is now resting firmly against my tummy and his hands give way and his full weight presses down on me.
"Oops, don't fall down Robert," he laughs, "I'm just about to start the ride!"
He pushes himself back up and takes his weight on his arms and starts to kiss my neck. Then one of his hands fumbles around at the front of my crotch. His hand strokes my sleek thighs as he slowly rapes my back passage.
Robert starts to slowly thrust in and out of me, hardly moving his cock more than an inch in and out; he is panting and slobbering at my neck, kissing and licking me. I close my eyes and try to relax my internal muscles so that the pain in my back passage will subside.
Robert's hand strokes my thighs and groin as he slowly fucks me, he is obviously delighted in the feel of the slinky nylon and satin on his skin because he is pushing his crotch hard against my buttocks on the in stroke. He begins to fuck me harder and faster, establishing a hard and fast rhythm. I relax my sphincter and concentrate on keeping my back passage loose to accommodate him.
"Open your eyes bitch!" he gasps, "Look!"
I open my eyes and turn to face the mirror. Robert is thrusting against me, his sweaty body glistening with exertion; his hand is under the front panel of my panties ferreting around, pawing and stroking. He is alternately kissing me and slobbering at my neck. He thrusts in and out, pivoting his waist to get all of himself inside me, rubbing his balls on my nylon covered ass at the top of his in-stroke.
My back passage is full and it aches as Robert’s invading member slides in and out of me, but oh god, I begin to feel the spongy hard mass of his glans as they push against my prostate. I feel the first ripple of sexual pleasure from my anal cavity.
I raise myself up so that my buttocks push up further and I sway my hips from side to side to increase Roberts's pleasure and ensure my arse cheeks rub against him, as he obviously loves the feel of that. I turn my head back so that Robert can kiss my pouting lips.
Robert now starts to pound himself heavily in and out of me. I imagine that he can do some serious damage to my insides if he isn’t careful; but I still experience the wonderful tingle of excitement every time his cock massages my prostate. He fucks me harder and harder and is grunting and panting really hard now. He grasps my hips and pulls me hard up against him, thrusting forward and back. He jackhammers himself in and out of me, groaning and cursing.
"Fucking bitch! Fucking Whore! Fucking take this you cunt!" he screams.
He pushes in hard and grates his balls against my arse as he shudders. His grip on my waist is like iron. I sense his cock start to convulse inside me as it shudders and secretes his hot spend. Robert's cock actually expands further and fills me completely and I think that the walls of my back passage will tear as Robert orgasms deep inside me. Jet after jet of hot seed stream into me as he rocks slowly back and forth. His semen further lubricates his cock and any pain I am experiencing goes away immediately. Robert is hissing obscenities as his orgasm peaks. I feel his spend drip from my sphincter and run down into the crack of my arse.
As Robert’s glans pulsate and throb against my sensitive prostrate, washing it with his hot seed, I experience a stab of exquisite sexual pleasure pulse through me and simultaneously stiffen and ejaculate into the front of my panties. I shudder with pleasure although I feel utterly debased.
Robert pushes me down into the mattress and pulls back so that his cock slides out of me, a torrent of his semen joins the trickle running down my crack and, as he lifts himself up, globs of semen drip from his member onto my stocking tops and legs. I can’t believe how much semen he expended.
Robert leans down and kisses me full on the lips.
"That was fantastic; you are one hot tranny whore," he laughs.
Robert grabs a handful of my half slip and wipes his cock on it. The silvery gleam of semen and KY jelly soak into the white satin fabric.
I am left lying on the bed my clothing dishevelled, with my legs akimbo and my slip and stockings stained with semen, my ankles and wrists still pathetically bound to the bedposts by the pantyhose restraints.
"Satisfied?" I inquire.
"Certainly. Are you?" Robert responds.
"Well; maybe just a little constructive criticism if you don’t mind." I answer easily removing the pantyhose restraints and getting up off the bed. I pull down my slip and skirt; adjust them over my thighs and reach for my cigarettes.
I walk over to where my webcam is mounted on top of my laptop, strategically positioned to take in a widescreen view of my bed. I blow a kiss into the lens of the webcam and shut it off. I close my website down on the laptop and log off from the Internet.
"Well honey you were fifteen minutes late getting here; the punters on my website expect the show to start at nine p.m. sharp!" I chasten him.
"I couldn’t find the fucking key to the front door; I’m sure you said the third flowerpot on the left of the windowsill," Robert complains.
"Ok, but next time try to get started on time; and you need to be careful when you dry hump me like that. You nearly lost control and came all over me; which I actually wouldn’t mind, but the punters want to see me get a good fucking." I said
"Also, those pantyhose are the most pathetic bondage restraints. I know that you need the freedom to manoeuvre me around the bed and have me wank you and so on, but we need some more believable restraints. Also, maybe you could threaten me with a knife or something?" I went on.
"That might work," Robert answered, "I could use it to cut the crotch out your knickers before I fuck you; for a more dramatic effect," he smiled.
"And that’s another thing hun, you know I like it rough but that trick of pushing my pantyhose inside me wrapped around your cock is only ever going to happen again if you use twice as much lube!" I snap.
"I’m sorry sweetheart; I though you might like it for something different," he smiles sheepishly.
I walk over to where he is standing, still naked, and lean in and kiss him. I take his cock in my hand and wrap a stockinged leg around his as I embrace him. I whisper in his ear.
"And finally darling, I love you and I love your cock dearly; but you could lose a few pounds," I giggle into his ear and softly squeeze his hardening prick.