Chapter 3: The Cost of Doing Business

The woman is 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. She's attractive; heavily madeup and her black bob is obviously a wig but of good quality.

She falls to her knees and smiles. A faceless man approaches; his fly is undone and an enormous erection pokes out of his trousers. Her hand snakes out and she caresses the pulsing manhood quivering only inches from her face. As her fingers encircle the phallus I notice her fingernails are painted ruby red. She leans forward and engulfs the proffered organ with her mouth; her lipstick matches her nailpolish.

I wake up with a start; I'm sweating and sporting an erection. The dream is still vivid in my memory and I lie there thinking about it. Is it a dream or a repressed memory?

The woman in my dream is me. I know that. Even though I am a middle-aged man in my early forties named Michael Nyland. The woman in my dreams is named Michele Nylons and she is an attractive, sexy, middle-aged transvestite. And; as I just stated; she is me!

"Mike?"

My restlessness has woken Nadine, my wife.

"MMMMmmm! Is that for me?" her hand slides under the covers and gently squeezes my erect penis.

She is still dressed in sheer crotchless pantyhose and the satin baby-doll pajamas that I had coaxed her into wearing to bed so we could make love. She still wears the makeup I need her to wear to fulfil my fantasies and it has smeared and her eyes are panda-like because of her smudged mascara and eyeliner. For some inexplicable reason it makes her look even sexier. The high-heeled sandals she wore during our lovemaking lie discarded on the floor beside the bed.

Nadine was so exhausted after our session that all she could do was kick off her heels and crawl into my arms and fall asleep. We both have work in the morning after all.

I'm surprised that she is not too tired and sore to want any more sex but her hand is coaxing my erection to full tumescence. She rolls over and snuggles up beside me; placing a nylon-clad thigh over my torso, seductively rubbing it on my sensitive skin. Her hand continues to caress my manhood.

"Quickie?" she smiles at me in the dark and then kisses me.

Her breath tastes of red wine, which we drank during our lovemaking, and sleep. Her body reeks of stale sex and perfume. She is still sexy as hell, even with her smudged makeup, stale breath and her bruised and semen-clotted vagina.

I roll her on her back and my tongue slides into her mouth at the same time as my erection slides into her buttery cunt. Her legs instinctively ride up and pantyhosed thighs caress my flanks as I begin to fuck her with long deep strokes.

There is no need for foreplay; her vagina is still soggy with a coagulation of semen and vaginal juices and my hardon is rock-hard from my dream.

"MMMMmmm! Come on; do me Mike! Make me come!" she whispers in my ear and then bites the lobe as an added incentive.

I drive myself deep inside my wife and then begin to jackhammer my cock in and out of her; she responds by rising to meet my thrusts and rubbing her legs on my body, spurring me on. He cunt is wet now; not from our previous lovemaking, but from fresh vaginal juices. She is moaning, her tongue working its magic in my mouth.

We climax together; grinding. Our bodies locked groin to groin, our pubic bones clash with the dull pleasurable pain that only intense sex seems to illicit. Nadine rakes my back with her fingernails while her feet drum on my body coaxing me to empty my seed deep inside her.

I feel her vagina quiver and squeeze my ejaculating penis, as it only does when she is experiencing the most intense of orgasms.

We lie locked together like two dogs tied by the knot until both of us are sated. I feel runnels of semen and cunny juices flooding from Nadine's puffy vagina; they soak into her pantyhose.

Eventually Nadine extricates herself from underneath me. She kicks off her pantyhose and throws them on the floor. She rummages around in the bedclothes and eventually finds her panties, she pulls them up her legs and scrunches then around her ample ass without any pretence of behaving ladylike.

She rolls over and kisses me and as she does she cunny-farts.

She smiles at me in the dark.

"Oops!" she giggles.

"It's your fault anyway. God my cunt is sore!" she pecks my cheek and turns her back to me, spooning, she pushes her behind into my groin but she is sweetly snoring in seconds.

What Nadine doesn't know; or need to know; is that when I climaxed I was thinking about the woman in my dream engulfing the erect penis of a stranger. I was thinking that I was that woman.

Don't get me wrong; I love my wife and I love making love to her. Our sex life has never been so good; well not since I came out of my coma, I don't really know what it was like before that but Nadine tells me it's currently the best it's ever been so I believe her.

The fact that I only get aroused when she wears lingerie, high heels, makeup and perfume, sexy skirts, dresses and blouses does not inhibit our lovemaking. Nadine has been well aware of my fetish for years now, she tells me. She knows my peccadillos and, other than the inconvenience of having to dress and make herself up; it actually works to her advantage.

If she wants sex; voilã, all she has to do is dress accordingly. And she has admitted that since I came out of my coma our lovemaking has increased both in frequency and intensity and that she is more than satisfied. What she doesn't know is that I own nearly as much sexy lingerie, and as many skirts, blouses, high-heels and as much makeup as she does.

Or that I regularly meet another transvestite by name of Vanessa at the Southside Inn and dress up in said accoutrements and have what we call transbian sex. That's transvestite-on-transvestite sex for the uninitiated.

And I have to admit that until a few weeks ago I was the uninitiated! Apparently before my accident, about four months ago now, I was quite a regular participant in the underground transvestite scene. Then I had my accident and was in a coma for three months and when I regained consciousness I had lost certain parts of my memory; memories mainly regarding my sexual peccadillos.

I discovered the truth about my crossdressing past and then contacted Vanessa who has been leading me through the magical world of crossdressing and transvestism, which I find fascinating and extremely sexually rewarding. We have met three times now at the Southside Inn but I can tell Vanessa is getting a little impatient with me.

She wants me to experience a transvestite party where I can explore sex with other transvestites and admirers (who I now know are men that - well they admire transvestites) but I'm too scared to move beyond my intense foreplay and fellatio sessions with Vanessa.

She tells me I used to be quite the slut! More than happy to gang-bang away the night with all comers (pardon the pun). But I'm reticent now. I like what I have with Vanessa; it's sexy, sensual, discreet and mutually enjoyable. And I have to admit I'm scared of the thought of having sex with a man. Very scared!

Sure in my dreams I am more than happy to swallow the load of some faceless admirer but I just can't bring myself to reconcile to the idea in real life. Wouldn't that make me a homo? Not that dressing like a girl and sucking my new friend Vanessa's cock while he is dressed as a girl is in any way homo! Is it?

The easiest way to deal with the situations is to just not to deal with it; to let Vanessa try to cajole me into attending a tranny party whilst still enjoying the fruits of her company. It's been working for a while now so why disturb the status quo?

These are the thoughts that clatter around my brain as I fall asleep cuddling my wife.

Little do I know that my life as Michele is about to change and that I will have very little control over the circumstances of that change.

The next evening I'm in my study with the Sony notepad open and my 'Michele mobile' on charge. I'm hoping for an email or text from Vanessa to organise our next meeting. I open my hotmail account and among the junk emails that my junk mail filter has failed to auto-delete is an email from John@JohnsPCsalesandrepairs.com. I am about to delete it when I figure I better open it.

John was the guy who unlocked my Sony notebook when I discovered it a few weeks ago after coming out of my coma, but I couldn't remember the password. I remember John carried on a little weird and kept going on about being into 'the scene' which I didn't understand. I now presume he meant the crossdressing and transvestite scene; not to subtly letting me know that he is an admirer. He must have seen some of the hidden files on my notepad, which fills me with a little trepidation but I open the email anyway. It might just be a warranty issue or maybe he put me on his adverting mailing list.

The email reads:

'Michele,

You must remember me from when I cracked open your laptop for you. I must say I found the contents of the MN folder very interesting, exciting, and very much to my taste.

If you are interested in meeting an avid admirer I would love to meet you.

John'

Fuck! Now I have this guy pressuring me as well as Vanessa! Well I'm not going to be coaxed into doing something I don't want to. I draft a reply and send it:

'John,

I don't understand what the fuck you are talking about! I don't know any Michele or know of any hidden MN folder and can't understand why you would be an 'avid admirer' of a salesman who works for a mediocre publishing house!

Mike'

As soon as I've sent the reply I realise my mistake. If I don't know anything about Michele and the MN folder; how come I'm logged into Michele's msn email account?

"Fuck! Fuck! Fuck!" I rant.

"You must be really horny or very angry," Nadine calls from the other room; the satire in her voice evident.

"Shall I break out my high-heels and stockings or a bottle of scotch?" she chuckles, leaning against the doorjamb of my study.

She's not long home from work and is wearing a grey business suit, tan hosiery, black high-heels and full makeup. She crosses her ankles knowing she looks sexy as hell.

"Break out the scotch; I'll take you as you come," I slam down the lid on my notebook and leap up from behind my desk; my erection is tenting the front of my trousers.

Nadine makes a show of running away from me but she is giggling. She falls on the couch in the lounge room and her skirt rides up exposing her luscious, silken-clad thighs. She makes no attempt to pull her skirt down.

"If you fuck up this suit Mike you're paying for the dry cleaning! And this will be the third pair of my pantyhose you've ruined this month!" she whines, but I can tell she wants it as much as I do.

I'm in the office the next day when my world is turned upside down.

I receive another email from John the PC guy but this time it has been delivered to my work account. This is very disturbing! Is this guy some sort of stalker? Only one way to find out!

I look around the office to ensure no one can see my work station and open the email.

'Michele honey,

Why are you playing so hard to get? I know who you are and what you do, and even who you do it with. See attached files.

John

PS. It only takes a click of my mouse and the attachments can be sent your wife's work and home email accounts and also all of your work colleague's accounts. You do look stunning and quite unrecognisable as Michael but once I tell them who Michele really is under all that makeup and wig; I'm sure they'll join the dots. As Dave Edmunds is want to sing: "There are some things you can't cover up with lipstick and powder"... '

I become very pale and I think I'm going to faint. I begin to tremble and I can't control my breathing. With extreme trepidation I open the attached folder.

It comes to me as no surprise that the folder contains a number of pictures of Ms Michele Nylons (AKA Michael Nyland in drag) dressed in her whorish best; some of them with her sporting a rather large erection.

You wouldn't know it was me. That is to say you wouldn't know it was me unless someone told you, and then you would look very hard and determine that was me!

Fuck! Fuck! Fuck!

Before I have time to panic another email arrives from the same address.

'Michele,

I know you have just opened my previous email (god its good being a computer-nerd sometimes; cloning, phisting and tracking cookies are my stock in trade) so you know what I have on you. I also have your entire email address book from this PC and I have been monitoring the Sony notepad that you use at home.

I know you have been active with Vanessa (another girl I'd like to meet but let's not digress for the moment) at the Southside Inn and that will suit me just fine.

Be there tonight at 8:00pm, make some excuse to Nadine I don't care what, but just be there! Be dressed; I don't want to meet Mike. I now your cell phone number so I'll call you at eight and you will give me the room number.

Let's just call this the cost of doing business!

It's that simple Michele! Don't fuck this up! Just remember: one click and everyone knows your secret!

Kisses,

John

PS. Can't wait!!!!!!!!'

Needless to say I spend the rest of the day fretting. I try to contact Vanessa on her mobile phone but it is turned off and I am too scared to email her because I knew John is monitoring my email.

It eventually becomes obvious to me that the only way to deal with this mess is to meet this asshole. The hold he has over me is particularly ironic, as I have only really just started crossdressing. Blackmailing bastard!

I am too worried to work so I make an excuse and go home. Being not long out of a coma has its advantages; if I say I feel sick, them I am immediately allowed as much sick leave as I need. I ruminate on the problem for a long time while watching the minutes and hours slowly tick away. Then it comes to me! Fight fire with fire!

If I set up a camera and microphone in the hotel room I can get the necessary material I need to blackmail him back. In the first instance I will have footage of him meeting a transvestite in a hotel room and secondly I can secretly get video and audio of him admitting that he is blackmailing me. This seems to be the best plan. Lure him into a false sense security and let him think he is in control then turn the tables on him!

It's only 3:00pm when I enter the internet café and log onto the net. I stay well away from my Michele Nylons msn account and Google John's PC Sales and Repairs and go to his businesses homepage. It doesn't take me long to find out that my nemesis is in fact John Steele, the owner and manager of John's PC Sales and Repairs. A few searches later and I've found his Facebook wall. Fuck I love how people are prepared to tell you all about themselves on the Internet.

The irony is not lost on me that John used cyber tools in order to get the information from my computer and my TVChix page that he needed to blackmail me.

I find out that he is forty-four and married with two grown kids. That's all I need really to blackmail him back; the fact that I will expose him to his family as a transvestite admirer and or to the police as a blackmailer. Satisfied that I have what I need for now I print the information I need and head home, stopping on the way at a computer hardware store (needless to say not John's) to get the other items I need to make my scheme work.

I fill my small suitcase with the things I will need and head off to the Southside Inn and get a room.

I've text' Nadine that I'm working late and then going for drinks with the boys so I will be home late; incongruously the same excuse I have been using to cover my meets with Vanessa. Another thing that bothers me is that John specifically used Nadine's name in his email; but now I know the name of his wife!

I've tried to fill the suitcase with the least revealing and un-sexy items out of my extensive collection but I need to keep in mind that for my counter-blackmail to be effective; it must look like he is meeting me flagrante delicto. I open the case and arrange clothes, underwear, shoes, makeup and wig, ready for me to wear.

But first I need to make sure the other essential items that I need for tonight are going to function correctly. I open my notepad and insert a small wifi receiver into one of the USB ports and install and open a program that comes with the hardware I have just purchased. I take a small remotely controlled video camera and directional microphone device that is roughly the same shape and size as a tube of lipstick and turn it on. On the screen of my little PC the hotel room comes into sharp focus. I say a few words and note that they are being recorded on the audio monitor and then play back the little sequence.

Perfect! My plan should work! Now where to hide it? I look at my watch and notice that time is running out. After a few minutes of trial and error I have the camera hidden away between a couple of magazines on a corner table. After another couple of minutes remotely adjusting the field of view to take in the whole room I hide the notebook under the bed, ensuring it is still receiving and recording data from the camera.

I shower and change and am ready to receive my unwelcome guest at 7:30pm. I take a half-bottle of Shiraz from the minibar, I hate the way hotels and airlines think they have the right to charge you double the price for inferior drinks, but I pour myself a glass anyway. My lipstick leaves a red imprint of my lips on the glass.

I have selected a charcoal-grey business suit, the most demure of Michele's ensembles, and a cerise satin blouse. Underneath I'm wearing a red satin and lace bra and matching full-cut panties. I'm wearing taupe, sheer-to-the-waist pantyhose; no need for stockings and suspenders tonight as I won't be undressing. I've chosen patent leather black high-heeled pumps, and I am wearing my usual extravagant amount of makeup. I've accessorised with a jet-black, shoulder-length wig, silver jewellery, and a few perfunctory squirts of Poison, my favourite perfume.

I look attractive rather than seductive. I'm happy with the look; sort of overdone businesswoman; you know the type, the forty-year-old professional who is trying too hard to look young.