The Awakening
Chapter 1: The Woman In The Mirror

Copyright© 2015 by Michele Nylons

Shemale Sex Story: Chapter 1: The Woman In The Mirror - A man awakes from a coma only to find he has selective amnesia. He doesn't know that he has a secret life. He is a closet transvestite. At first repulsed by the idea, he can't help exploring his secret life. What is it like to dress as a woman? What is it like to feel feminine? What is it like to suck a man's cock!

Caution: This Shemale Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   Mult   Consensual   Romantic   NonConsensual   Reluctant   Coercion   Blackmail   Heterosexual   TransGender   CrossDressing   Shemale   Fiction   Cheating   Spanking   Rough   Gang Bang   Group Sex   Orgy   Oral Sex   Anal Sex   Masturbation   Petting   Analingus   Foot Fetish   Leg Fetish   Transformation  

Dark; then light; my eyelids flutter.

"Can he hear us?" a woman's voice.

Dark; then light.

"He's still comatose; but he's improving," an authoritative male voice.

Light; now dark, the dream returns.

I'm inside the mirror but I can't be seen. I try to reach through the glass but I can't. I try to speak but I am mute. I am a floating entity who exists behind the looking glass.

The woman is attractive for her age; early forties? She's seated in front of the large vanity mirror; she's finishing her makeup, applying a final coat of face powder. She wears too much makeup but it suits her.

Dark ruby-red lipstick; her lips are full and they glisten in the harsh lights of the vanity mirror. Her cheeks are rouged, accenting her well-defined cheekbones. Her eye makeup is striking. Black eyeliner carefully applied to her upper and lower eyelids. She has contoured each of her eyes, the black eyeliner begins in the inner corner of her eyelids, across the lash-line to the outer corners of her eyes, sort of like an Egyptian courtesan.

Black mascara; her lashes are coated so thickly you might think them false. Eyeshadow, blue-green blended into mauve and possibly even some purple. It extends beyond her eyelids almost to her brows, which are hidden by the bangs of her hair. A classic bob, brunette with subtle dark-red highlights.

She's preening now; a few strokes with the hairbrush, blending eyeshadow with her fingertips; a final flick of the powder brush, then she runs a finger along the edges of her lips. Her nailpolish matches her lipstick. She puckers and air-kisses her reflection; she smiles and is at once beautiful and radiant. The silver drop-earrings that dangle from her ears peek through her hair. The earrings match a necklace that adorns her throat; the rings on her fingers are also silver.

She stands. As she walks away I see the rest of her. Slim. Mauve satin blouse, navy-blue skirt, black high-heeled pumps. The hem of her skirt teases the backs of her knees. Taupe stockings with black seams. I smile. Who is she? Do I know her!

Dark again.

"It's a good sign Mrs Nyland," the doctor nods at my erection and at the smile on my face.

"He's obviously having good dreams in there," the woman replies, a little embarrassed.

The doctor nods and lifts the chart at the end of my hospital bed and scribbles some notes.

I wake from my coma four hours later almost three months to the day of the accident.

"Thank god Michael!" the woman smiles; but there are tears in her eyes.

She hugs me and I try to respond but I can't form the words I want to say to her. My arms feel like they have lead weights attached. I lift them up with great difficulty and drape them around her shoulders. It's the best I can do to comfort the woman sobbing against my chest.

"Who are you?" I manage to croak.

"Your wife," she sobs.

It's almost another month before I was allowed to return home, still suffering from transient lacunar amnesia. Some things I can remember like they only happened minutes before, and some things I can't remember at all. The doctors say that hopefully my memory will fully return, but not to expect too much too soon.

Nadine is my wife. I remember her now. I know I love her and I know we were high school sweethearts. She is an attractive woman for her age but she is not the woman I dreamt about in my coma. She wears hardly any makeup and seldom wears skirts and satin blouses; she's a pantsuit and cotton shirt girl. Sensible shoes and minimal accessories, that's her. Her hair is usually kept up; tied in a neat bun or swept back in a ponytail.

She nurses me until I am fully recovered and am ready to return to work. We work together trying to recover my memories and most of them have returned and I am keen to regain my life. I can live with the memory gaps that I can't fill; they will either return or they won't. I remember the accident too; I was clipped by a car whilst riding my bike.

We haven't had sex yet. Not for lack of trying; we have kissed, cuddled, fondled and caressed, but I remain impotent. We talk to the doctor about it and he says it might take a little time for my libido to return.

I wake each morning with a full erection and a fading memory or the woman in the mirror. My wife has tried to take advantage of my morning wood, or 'nocturnal penile tumescence' as my doctor calls it, but my erection diminishes with the memory of the woman in the mirror.

I finally return to work and am greeted with much love, hospitality, and accolades regarding my tenacity and my determination to recovery from my accident. Most of my work colleagues have visited me at home and eventually I remember them all. My boss promised me my job would be waiting for me if I recovered and he lived up to his promise.

I am a salesman for a large publishing house; one of the best salesmen in the state apparently. I soon get back on the horse and am selling my quota plus. I think some of my best sales are made because some of my clients feel sympathetic for me, but who am I to reject their generosity? After a few weeks its business as usual.

Now if I could just get my sex life in order!

And then Nadine surprises me.

I come home from work one evening after working late and find the lounge room is gloomy, lit only by a single floor lamp. Nadine stands in the pool of light. She looks awesome!

She's wearing a black pleated mini-skirt, split at the side. Her long legs are clad in sheer hosiery; flesh toned stockings with dark welts, I can see them through the split in her skirt. Her feet are shod in silver high-heeled sandals displaying the dark reinforced toes and heels of her nylons. A shimmery long-sleeved red blouse made from satin or similar fabric. It's partially unbuttoned and I can see her pert breasts cupped in a black lace bra.

She has let down her hair and combed it out; she wears it parted down the middle with bangs. Her makeup is wicked. Heavy black mascara and eyeliner, blue-green eyeshadow, rouged cheeks and red lipstick. Her nails are long and red; they must be falsies but they look great!

She looks so sexy! My cock begins to harden and tents my pants.

"Yep I knew it!" she smiles.

"What?" I stammer.

"I thought the accident may have changed you; but it obviously hasn't," she says sounding a little disappointed.

"The last few years of our marriage you were only ever able to get it up if I dressed like this. Like a slut," she explains.

"Really?" I reply but my eyes are scouring her body, entranced by her.

My penis is rock hard and throbbing.

"I keep these clothes and others like them at the back of my wardrobe and when I want servicing I dress in them and put on my slutty makeup," she gives me a wicked smile.

"It's the only way you can get it up so I live with it."

I cross the room and fall on her.

My hand goes under her skirt and caresses her thigh stroking the creamy skin above the welts of her stockings. Her hand reaches out and squeezes me through my trousers.

"That's the Michael I remember," she moans and then her lips crush mine.

She pushes me down onto the couch and straddles me pulling at my belt and zipper. Her skirt has ridden up showing off her stocking tops and my fingers rake her thighs. I now remember now how I love the feel of her stocking-clad legs. Her heavily made up face is a picture of concentration as she pulls my belt free of the loops and unzips my fly.

"Come on honey; fuck me! Fuck me like you used to!" she sighs and kisses me again.

I can feel her panty-clad mound against my erection and I hump her as she grinds her crotch against mine. She isn't the woman I see in my dreams each night but she's making me horny as hell.

My hands find her ass and I squeeze her buttocks; her hand snakes between our bodies and she grips my penis and slides it inside the gusset of her panties and she wriggles her ass and positions me inside her hot wet labia. She slowly lowers herself onto me and impales herself on my penis.

"Ohhhhh!" she moans and begins to fuck me.

I can taste her lipstick and smell her perfume; my fingers explore her sleek stockinged legs and panty-clad ass. I grunt into her mouth as I rise and fall in time with her.

We orgasm together; her vagina quivers and milks me of my seed as I empty myself deep inside her. Our tongues are entwined as we paw, kiss and molest each other. We grind and moan and wriggle and sigh; lost in the pleasure and satisfaction of our first climax since my accident all those months ago.

We slowly come down from the peak of our pleasure and my wife remains astride me, kissing me, she smiles her gratification. I kiss her and smile back.

"That was lovely," I whisper.

"You never have a problem getting it up when I dress like this," she beams down at me.

I frown.

"We've talked about it, its just a fetish you have," she goes on.

"Started with you asking me to wear stockings and heels and progressed from there. Now you can only perform while I'm dressed like a whore."

"I'm sorry," I say; but I'm still trying to get to grips to with what she's telling me.

"No need. We saw a counsellor a few years ago and went through the whole rigmarole. Then we searched the web and discovered that CFNM is a common fetish that some men have. Whatever it is, I've been over it for a long time now. You like it. It gets you aroused and you always give me a good fucking," she smiles down at me.

"CFNM?" I ask.

"Clothed female, naked male," she smiles.

I smile back.

"I really do seem to like it," I grin up at her and she giggles.

She can feel me becoming tumescent again inside of her.

"I was sort of hoping the accident might have cured you of your fixation but it obviously hasn't. Not to worry, I don't mind that much; its kind of kinky," she says and begins to ride me.

"Well its good that I know what turns me on," I say as I rise to meet her thrusts.

"Shut up and fuck me," she lowers her mouth to mine to shut me up.

Later we lie side by side kissing like teenagers. I can't keep my hands off her stocking-clad legs and her satin-pantied ass. I feel great, extremely satisfied.

But deep inside me there is still a longing, a feeling that I am missing something. My thoughts wander back to the woman in the mirror, but my wife has other plans. Her fingers find my manhood and we are off again.

The next day I find the laptop.

I tried every combination I could think of. My name, Nadine's name, combinations of our social security numbers, birthdays, but the laptop won't let me past the password protection.

I found the laptop in the bottom drawer of my desk; it's a Sony Vaio notepad. Under the laptop is a set of keys. Nadine says she's never seen the laptop or the keys before but they are obviously mine. Try as I might, I just can't remember the password for the computer or what the keys are for. I can't even remember ever using them.

It costs me sixty dollars to get the laptop unlocked at 'John's PC Sales and Repairs' at the mall. John calls me to tell me he has hacked into the computer and it's ready to be collected. I go down to the store the next afternoon; the shop is empty except for John and I.

"Sorry it took so long," John says apologetically.

"Its ok; I don't even know what's on it," I say scratching my head.

"Yeah, right!" John's smile is loaded with sarcasm.

"Really," I reply, "I don't."

"Sure," John continues to beam at me.

"Just so you know; I'm into the scene," John says, seriously now.

"The scene?" I haven't a clue what he is talking about.

"The scene hun," he winks at me.


The guy's a fucking weirdo; I drop three twenties on the counter and leave with my notepad.

I take my laptop home and open it up and reset the password. I check the 'my documents' folder and find nothing there, nor in any of the other folders. Internet Explorer has no favourites and the browsing history has been wiped; its almost like the computer has never been used. I'm tempted to take it back to John's and have him check the file system but after the way he behaved I decide against it for now. Besides Nadine has other tasks for me.

Now that I am fit and well she wants us to have a good clearout; she will go through the house, room by room and I get to clear out the garage and the attic. The garage only takes a couple of hours but the attic is full of junk; old furniture and brick-a-brack. I work my way through it methodically removing items we no longer need until I come across an old trunk at the very back of the attic.

Unlike most of the other junk up here the trunk and the area around it are free of dust and although the trunk is old its still in good condition. I switch on a floor lamp that is conveniently located right next to the trunk. There is a padlock on the front of the trunk; quite a substantial one too. I scratch me head for a minute and then I remember the keys I found in the same drawer as the laptop. I haven't been able to find out what the keys are for but I know that one of them is a Chubb and I think it might fit this lock.

I still can't recall why I might keep something locked away up here but I have to say I'm a little excited at the prospect of opening the trunk. I get the keys and confirm that Nadine is still busy cleaning out the other rooms. I figure that if I'm hiding something valuable up here its possible I might be hiding it from her too.

I'm quite disappointed when I open the trunk; it's full of Nadine's stuff. The top layer is made up of skirts and blouses, similar to the style of clothing she wore when we made love last night. I close the lid of the trunk and lock it. I decide I will ask Nadine whether or not she wants to keep the trunk and its contents or if it's all just more junk.

As I slip the keys back in my pocket I remember what she said to me: "I keep these clothes and others like them at the back of my wardrobe and when I want servicing I dress in them and put on my slutty makeup."

If she keeps her slut clothes at the back of her wardrobe what are the ones in trunk for? And why do I have a key?

I decide that she is the only one who can answer these questions and continue cleaning out the last of the junk. Two hours later we are both tired and dusty but we have gathered a considerable amount of superfluous brick-a-brack; enough to hold a garage sale, with the remainder to go down the dump. Guess who gets the job of taking the trash down to the dump?

By the time I get back from the dump Nadine has showered and is sitting at her dressing table drying her hair.

"I'm drying my hair here so you can use the ensuite bathroom honey; so shower up and we can get dinner," she smiles at me.

When I come out the bathroom half an hour later I am pleasantly surprised to find Nadine is wearing a basque, black stockings, high-heels and a ton of makeup and perfume. We fall onto the bed and any thoughts I had about asking her about padlocked trunks are immediately forgotten.

Its a few days later and I can't sleep. I sit in the den sipping single malt scotch whisky playing with the Sony laptop. I find myself opening the 'folder options' feature in 'my documents'. I click the 'show hidden files' button and apply the settings and my life suddenly changes.

A hidden folder named 'MN' suddenly appears and I open it. Inside are myriads of other folders, including some labelled: pictures, video, contacts, favourites, msn email, to name but a few. I try hard to remember why I might have a laptop that appears to be squeaky clean of any data but has a plethora of hidden files and folders.

I open the 'pictures' folder and find a group of subfolders inside; one of which is labelled 'recent pics'. I open this folder and there she is!

The jpg images inside the folder are all of the woman who keeps coming to me in my dreams; the brunette with the classic bob and subtle dark-red highlights, black eyeliner and mascara, multi-hued eyeshadow, rouged cheeks and lipsticked lips. She is wearing the same mauve satin blouse, navy-blue skirt, black high-heel pumps and taupe stockings with black seams, as the woman of my dreams.

She has struck various provocative poses, including some pictures where she is air-kissing the camera and a few where she has raised the hem of her skirt up her thighs revealing her stocking tops. Then I get a real shock. I open another subfolder labelled 'XXX' and this time the woman is in various stages of undress; everything from lifting her skirt up to show off her pretty pink panties, to a couple of pictures where she is clad only in bra, panties, suspender belt, stockings and heels. But what is most astonishing is the woman is sporting a large erection. She is a he!

I close the windows but I have to admit I'm intrigued. The woman is a transvestite. The woman of my dreams is a transvestite?

I open the 'favourites' folder prepared to be shocked but I find only a couple of Internet links. Whoever owns the data on this laptop seems to be very generous when it comes to storing images but frugal when it comes to storing data and links.

I click on a link labelled 'TVChix' and Internet explorer takes me to a web page titled: 'Michele_Nylons Adventurous Transvestite'. I check out the profile but I'm confused. It describes a person in their early forties who likes to crossdress and meet other transvestites and what are described as 'admirers' for casual sexual encounters. Accompanying the profile are numerous pictures similar to the ones I found in the 'pictures folder' of the laptop.

I notice a link to an email address: and copy the link. I'm going to get to the bottom of this! Why is this Michele Nylons person the subject of my dreams? Why did I dream of him or her in my coma and why are the dreams recurring now that I have mostly recovered from my coma?

I close down the browser and open the file labelled 'msn email'. I find a single link that takes me to a hotmail account. The password is obviously saved to this computer as I'm logged in straight away and I furiously click on the 'New Email' button. I want to find out who this Michele Nylons person is and why I have so many pictures of her (I can't help but think of the person as a her even though she is a transvestite), links to her web site, and why I keep dreaming of her. I compose an email pasting her email address link into the address bar.

'Dear Michele Nylons, my name is Mike and I have recently recovered from an accident resulting in me being comatose for a considerable time. I now find that I have pictures of you and some personal information about you that I find a little disturbing. If you are a friend of mine and I have forgotten about you because of my memory disorder which the doctors call transient lacunar amnesia, which means I don't remember some things from before my accident, please let me know how we know each other and explain why we are friends.'

It is with some trepidation that I compose this email. I might find out some things from my past that are best forgotten. Am I one of these 'admirer' type people? Am I attracted to transgendered males? What the fuck is going on? I hit the send button and a take a large gulp of scotch.

Within seconds I see an alert telling me that I have new email and the inbox opens automatically. The message reads: Dear Michele Nylons, my name is Mike and I recently recovered from an accident... '

The email has arrived at its destination; the same place from which it was sent! This inbox belongs to Michele Nylons. I take a closer look at the inbox. Michele Nylons has thirty-seven unread emails.

My consciousness fades and I think I'm going to faint, then I am stunned into coherence as I begin to realise what is happening. I open the 'pictures' folder again and closely study the stunning mature transvestite featured in the images. I am shocked! I am she and she is me! A silly impulse makes me think of the Beatles song 'I Am the Walrus' and I burst into uncontrollable laughter.

I stop laughing as the gravity of the situation occurs to me. Suddenly I join the dots. The woman in the mirror, the woman in my dreams, the secret laptop with the hidden files, the pictures, the secret hotmail account, the trunk in the attic, it begins to make sense ... The trunk in the attic!!!

I drain the last finger of scotch and race up to the attic.

I unlock the trunk rummage around; under layers of skirts, blouses and lingerie I find a number of pairs of high-heels. I hold up a pair of cherry-red, platform soled, high-heel pumps. They are size ten. I don't know too much about women's shoe sizes but I doubt that Nadine is a size ten! I kick off my slippers and my feet slide effortlessly into the high-heels. They fit perfectly and I stand up in them and am surprised I have no problem keeping my balance. I take a few tentative steps, unconsciously I adopt a womanly gait, placing one foot in front of the other as I stride like a catwalk model across the attic floor.

My mind fills with vague memories of sleek stockinged legs and feet shod in expensive high-heels gliding along the floor. Long legs, well-formed calves and thighs; my legs!

I look down at the ridiculous sight of my feet shod in the cherry-red pumps with my legs clad in my cotton pyjama pants. Then I hear footsteps on the attic ladder.

"Mike? Mike? What the fuck is going on up here its three in the morning?" she calls.

I come out of my reverie and quickly kick off the high heels, jam them into the trunk, throw the clothes on top and slam it shut.

"Sorry hun I couldn't sleep," I reply as Nadine's head pops up over the trap door.

"So you decided to parade around the attic like an elephant on steroids? It was so loud! What the fuck were you doing?" she frowns.

'Trying on some high-heels that I have just found out I like to wear!' I think to myself but of course I answer differently.

I look around the attic and quickly spy my ski boots sitting in the corner next to some bindings and skis.

"Er ... I tried on my ski boots; I'm thinking the ski season isn't that far away," I stammer.

Her face breaks into a huge grin.

"You silly boy! That coma really fucked you around Mike. You haven't skied for years!" she laughs.

"Now come back to bed and maybe I can help you sleep," the smiles seductively at me.

True to her word when I come back to bed she's lying on the covers dressed in the same basque, stockings and high-heels that she wore the last time we made love. She's put on a little makeup and perfume and combed her hair.

I kneel at the foot of the bed naked, my erection proud and rampant. I slip out my tongue and lick her slim stockinged ankles, taking her feet in my hands I massage her calves and she sighs. I slide my tongue along her legs and I spend a few minutes teasing the fine wrinkles in her stockings at the backs of knees. She shudders and her fingers twist my scalp.

"You know how to get me going Michael Nyland," she groans.

I continue the journey up my wife's elegant legs stopping at the tops of her stockings to explore the dark welts and the smooth creamy skin of her thighs. She guides my head to her crotch and I lick her mound through her black satin panties. They are moist and pungent with her juices.

"Stop that! You know what I want!" she pulls aside the gusset of her panties and forces my face into her sex.

My tongue explores her labia and the finds her hooded clitoris. It is erect and as soon as I lick it Nadine pushes my face into her groin and writhes against me.

"OOOOhhhhhh!!!!!" she moans.

I lick her clitoris with long slow strokes and gradually increase the speed; my wet tongue lapping her sex and I taste her sweet secretions. Her heels are drumming on the bed and I know she is close to climax. I frantically suckle her sopping vagina ensuring my tongue lashes her clitty. I grasp her hips and force my face into her sex as I lap, suck, lick and caress her.

"OOOOOOOhhhhhhh Fuuuuuuuck!!!" Nadine entwines her fingers tightly in my scalp and holds me against her as she orgasms.

I lick and suck her to climax and then ease off as she begins to come down. I know her clitoris gets really sensitive after she comes. I lick it a few times and then I feel her pulling my hair. She pulls my face up to hers; she's sweating a little and her mascara is smeared. It makes her look even sexier. She kisses me; exploring my tongue with hers. She opens her legs for me and I slide between them; her stockings feel exquisite on my bare flesh.

"Put it in me Mike! Fuck me!" she moans and reaches down and places my penis at the entrance to her hot wet vagina.

She lifts her legs and wraps them around my flanks and pulls me to her. My rampant penis slides inside her hot, buttery hole and I hump away as she kisses me and rakes my flanks with her high-heels, goading me on like a rider on a horse.

I slam my turgid member in and out of my wife for about thirty seconds before I feel my orgasm approaching. Nadine is coming again too and she pants her sweet breath in my ear whispering obscenities and drums her heels on my back to encourage me. I empty my seed deep inside her, grinding the base of my penis against her pubis so that I am stimulating her clitoris.

We remain wrapped in each other's arms kissing and stroking each other. Then Nadine reaches around my body and pulls off her high-heels.

"I'll leave the rest on; I'm too tired to change and we both have work in the morning," she whispers.

"Don't get any ideas big boy, I know you love me dressed this way but I need my sleep," she smiles and nuzzles my ear and squeezes my deflating penis.

We both get comfortable; she's lying in my arms and my penis is pressing against her stockinged thigh as we both drift off to sleep. I am confused. All through our intense love making, magnificent as it was, I imagined that I was in Nadine's circumstances. That it was me dressed in basque, stockings, heels and makeup and being made love to.

What is happening to me?

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