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.