The Journey Pt. 01

Part 1

The Journey.

I sat in the back seat of the car, my legs stretched in front of me and crossed at the ankles, the short skirt I wore barley covered my panties, and I could feel the cool leather of the seat press against my legs.

I smiled at the reflection of the drivers hungry eyes in the rear view mirror, longing, lust, and power, mixed together in a heady cocktail shining back at me. My clit warmed within its confining restraint, and I was sure he could see the need in my eyes, gazing back at him with their promise of sissy satisfaction.

To my right, dressed in expensive Black Business Suit, radiating assurance and calm, sat the tall, elegant, woman who had introduced me to, and guided me through the journey I had embarked on.

"We are nearly at the Clinic" Mistress Anna's soothing voice said, "it has been a long journey for you Josephine, but you have met ever challenge I have given you, and you are deserving of this reward."

Today I would finally earn my breasts, my transformation from geek to slut would be complete, my heart was bursting with happiness.

Reflection.

I sat on the single high backed plain wooden chair in the center of the White room, from the ceiling blazing spot lights shone, casting my reflection in Four directions, leaving me at the center of a strange saltire of shadow.

There was no color in the room, no decoration; In front of me were two doors, both as White and bare as the walls with no indication of where they might lead, the door behind me, which I had come through some Fifteen minutes ago, was similarly stark and remained shut.

The room was chilly, perhaps in the low Sixties, but I could see no thermostat on the walls to accurately measure by. No sounds penetrated here, it was the bleakest most exciting place I had ever been. There was nothing in this room, except what I had brought into it, and I sat there shivering, anxious, nervous, my thoughts engaged, but running in every direction simultaneously, and I struggled to gain control of my emotions.

Behind me the door opened, and I could hear the click of heels, slow stride striking the concrete floor, as someone approached behind me, I kept my gaze firmly to the front as I had been instructed and allowed the new sensations to register. The soft warmth of her breath on the back my neck, the smell and taste of a light perfume, the passing of the seconds amplified into hours by my apprehension.

I felt a hand softly press onto my right shoulder, long fingers ending in a perfect manicure filled my peripheral vision, and more seconds passed. I didn't fully understand what was happening yet, but anticipation woke the heat in my blood, and I felt my cock lengthen and harden.

Finally a soft melodic voice broke the silence, "Good morning Joseph, Welcome "she spoke with a mixture of amusement and reassurance "I am so glad you decided to keep this appointment", Her other hand settled on my shoulder, I knew I was not the first to sit here, that she had been through this many times before, and she allowed me time to have my thoughts drift away before returning to the present.

I don't remember when I first started fantasizing that I was a woman, now it seems something that has always been part of me. I know for years I fought against the temptation, I would turn my dreams to nightmares to avoid the sight of me dressed in a schoolgirl's uniform, a long black cocktail dress split to the hip, a flimsy negligee, because I was certain of what would come next, and I could not face it.

Over time lust fought a wining battle with sexual ambiguity, and my defense started to crumble, Women's magazines showed me new ensembles to add to my fantasy wardrobe, I allowed my forbidden dreams to expand, the nightmares replaced with thoughts of palatable lesbian sex, then group sex, add a little bondage to the mix, little by little each wall was broken, until finally I saw myself dressed in White like a bride on her wedding night, a naked lover stood before my kneeling body, gazing encouragingly down at me, as for the first time my mouth opened to please the large cock, purple veins pulsating with lust which danced temptingly before my eyes.

After that moment I don't believe I ever played the man's role in my fantasies again, until then I could still occasionally force visions of myself mounting a woman, feel my cock ride her pussy for my pleasure, turn her ass checks red with a punishment spanking before throwing her over the bed to take her roughly from behind, let my fingers gradually lubricate and widen her asshole before slipping my cock past her gasps, deep in to her humiliation.

Not after that moment.

My fantasy life took control of my real life, rather than working on cutting code in my smelly cubicle deep in the bowls of corporate hell, I spent my time writing down last night's fantasies, often I had more than one to transcribe, my hard on tented the suit trousers below the desk, and sometimes if I was very lucky, I would ejaculate into the boxers underneath as my newly unleashed eroticism crushed my last taboos in waves of illicit pleasure.

EBay became my friend, anonymously (or so I thought) I started to buy lingerie, panties, teddies, stockings, suspenders, my drawers filled as silk and cotton from Victoria's Secret evicted Mr. Jockey. I had not yet crossed the line to wearing it, it stayed packed and neatly stacked, occasionally laid out on the bed mocking me for my cowardice.

Then the evening came when I walked into my bed room and turned to the mirror to see the girl I had always wanted to be facing me, provocatively dressed in a matching Black panty and bra set, the Red lace trim and bows matching the inexpertly applied lipstick, and for the first time in many months, contentment settled on me. I leaned forward, my lips kissing her reflection, I felt my foreskin role back as my erection began to take hold, harder than it had ever been, longer than it had ever been, an unexpected breath released as the head pushed up and out of the panties flimsy band and my tongue continued to work the cool glass of the mirror.

I reached to the dresser at the side and poured a generous portion of scented lube on to my hand, the smell of Lavender mixed with the sweet smell of my passion already filling the room, I extended the band of the panties out in a cute little tent, and from the top of my cock I let the lube slowly drip down the engorged shaft till the slight chill touched my balls, my hand pressed urgently under the cotton, softly caressing each inch of my cock, as it gently spread the gel over every inch of skin, the chill as promised in the adverts turned to a gentle heat and my cock strained as the excitement tried to lengthen it beyond its natural limits.

I could feel a little of the lube pool at the bottom of my balls, I let a finger push it around, along the bridge until it wet around the edge of my virgin ass hole, I didn't know why, but I had no temptation to push that single finger inside, it just played around the edges, a little pressure in the middle, teasing my heightened senses, without penetration.

I looked into the mirror to see the picture of a slut in heat being man handled for pleasure.

I could stand no more, I threw myself onto the bed, raising my hips as I ripped the panties off, my legs spread as wide as they could, and my hand crushed my cock, working itself up and down to the rhythm of the imaginary lover penetrating my boypussy. It was only seconds before I screamed with the release of orgasm, I had never shot a load with such force before; the White sticky sissy spunk launched itself in an arc across my heaving body to cover me from face to belly.

I had crossed into a life I could never turn back from, I turned to the mirror to gaze lovingly at my sissy spunk covered likeness, slowly, I let my hand reach up and my fingers rolled to catch the precious glue to them, winding across the lines of each wet trace, they gathered as much as possible and keeping my eye on the mirror, I rounded 3 fingers into a rough approximation of a cock, and greedily drove my head down on them, my mouth opened wide to take them deep, they touched the back of my throat and I gagged as I truly tasted myself for the first time.

I woke in the morning with the bra pressing uncomfortably into my back and shoulders, the smell of cum filled my nostrils and initiated vibrant memories of last night's antics, I gazed down at my cock, fully erect again, and repeated my imaginary blow job and fuck.

As I left for work that day, I laid out the set of women's clothes I wanted to wear on my return, as soon as the door closed behind me, I stripped and changed. This became my life, at first it was just underclothes, but my wardrobe rapidly expanded to include light summer dresses, pencil skirts, tight blouses and skimpy tops. I tried heels once, and decided I was a pumps sort of girl.

I was rarely naked; I needed some form of women's clothes on me to breath, I wore a bikini to the shower, a negligee to bed. Panties replaced boxers under my work suit, and I had to learn self-control lest I stain the trousers too badly during the day.

I never went drinking with colleagues any longer, preferring to rush home and into the seclusion of my feminine embrace.

Initially my masturbatory life was amazing, I lost count of the times I came during the day, and it seemed that I walked around the confines of my little world with a permanently erect cock. For a time, I was happy, but time can't stand still, in front of my mirror, my fantasy sex life became more, well more everything.

After a presentation at work, our directors bent me over the boardroom table to take me one by one; sometimes I would have a female director with a strap on joining in the fun. Watching football on TV would end with the squad and I engaged in a locker room gangbang. I was a virgin schoolgirl taken by her teacher, a Bride taken by her husband, sometimes he was left on the floor, tied up, as the Priest laughingly helped himself to every hole. I was a slave, a biker chick free for the gang to use, an airhostess rented out by the pilot as part of mile high initiations, I was reaching the limits of imagination and I knew my happiness would become despair if I could not step beyond them.

And then the letter arrived, expensive vellum, hand written calligraphy, its scent was of fine perfume, its unspoken message was of elegance and refinement. I knew no one with that sort of taste; my peers were other programmers who thought a terse email earned them communicator of the year awards.

I opened and read it; it told a tale I thought only I knew, only I could know, the first page was written as if my mind had been trawled and transcribed, it expertly and graphically relived that first time in front of the mirror, my hands were shaking with shock, the skin on my head rapidly constricted, bringing the first signs of a migraine. Regaining my breath, I read the second page, an invitation and the promise of an explanation.

And so here I sat, perversely apprehensive, on a high backed wooden chair in the center of a strange White room, gaze fixed firmly forward, with a pair of feminine hands resting on my shoulders, waiting.

Choice

"Are you a Virgin Joseph?"

I paused slightly, I didn't want to answer the question, she waited behind me, the conductor of a train making a journey I desperately wanted to take, willing to let me board only if I presented a ticket of complete honesty.

"Yes Ma'am, I am."

"Good. You must always be honest with me."

Her hands released from my shoulders, and she slowly rounded the seat to step in front of me. Six inch heels extended her already tall frame, a tailored suit perfectly fit over the slim shapely figure, her long dark hair hung lose over her shoulder, and just a trace of makeup was in place highlighting the perfect skin and Asian features.

"A 29 year old Virgin! That's unusual, I wonder why! What have you been saving yourself for Joseph?"

"I'm just not very good with girls" I said "well that's not entirely true; I have friends, I just don't seem to be able to connect with them."

She looked down at me, her eyes smiling "Call me Mistress Anna."

"Yes, Mistress Anna."

"Good" she purred, "a quick study, you'll need that."

"Would you like to know why you fail with girls Joseph? It's not because you're unattractive, although I know you often think so, and it's not because you lack confidence, or bad timing, or any of the other excuses you have constructed to insulate yourself from failure, none of that is true."

I waited as she stepped back from me "Stand up," "Walk forward," "Stop."

Instinctively I obeyed her instructions, her body, her voice, compelled me in a way I had never experienced before, her words went into my ears then sunk into the very core of my being, she had an authority over me that I could not refuse.

She walked around me, inspecting but not touching "Girls instinctively know dear" she told me "They know what you can't tell anyone, that you're not really interested in them in "That Way" because you're secretly one of them."

I stayed silent, but my chest tightened as her words exposed the truth I had avoided for so long, the truth I had kept secret from everyone, the truth, even now I wasn't fully ready to accept.

'How, how did you know Mistress?" I stammered.

She laughed, it was light, and easy, not at all insulting, she explained in great detail how a subroutine had been worked into the EBay software, Pattern Analysis, my sudden shopping spree had met certain parameters and flagged them for her interest. After that, my apartment had been broken into and wired for sound and video, she had my many days of self-satisfaction caught on tape, she knew she had her girl.

She didn't explain why.

Her hand lightly brushed my neck "You're secrets are safe with me Joseph, if you want them to be."

"I am here to offer you a choice, the door on the left leads to the outside world, if you chose that door; you will find an invitation to a place where you can safely choose to indulge your fantasies to the limits you set upon yourself. The door to the right however, that leads to a new world, a new you, the real you, a world with no limits."

I was paralyzed, I couldn't move, I couldn't speak, I could only wait, trapped in the power of her seduction and promise.

"Wouldn't you really like to be a woman Joseph? Vibrant, sexual, desired, the object of men's lust" She walked to the door behind me, "I hope to see you again my dear, I believe we will do great things together."

I was left alone, in this cold, blank room, my thoughts raced as I tried to take in everything I had been told, programmers are logical beasts, to them decisions are always binary, two choices, facts turn the switch on or off.

I was unsure how long I had to make my choice, I didn't know what would happen if I couldn't, instinctively my hand reached for the right hand door, and I walked through.

The Second Room

The second room was very different, the walls were a warm a welcoming yellow, paintings of young beautiful woman were hung on them, one had a large screen TV affixed oto it. There was a Blue Love seat, the fabric a brushed sued in the middle, the smell of freshly brewed coffee that filled the room come form the coffee pot in the corner.

There was also a strikingly beauty woman standing in front of me, her thigh length high heel boots polished Black leather as were the trousers and collared top that reached to her neck. Her arms were bear with just a single small tattoo on the right bicep, her hair was short, barley touching her neck and she wore no makeup at all.

"I am Mistress Bette" she said "would you like a coffee?"

"No, thank you, Mistress Bette."

She moved to the love seat, and sat on the right hand cushion, she patted the left "Sit."

I quickly move to the offered place, remaining quiet while she picked up the remote control from the couches arm and turned the TV on. She said nothing more as the picture came to life and I blinked as I saw the inside of my apartment.

I was sitting on my bed casually dressed in Jeans and T-shirt and I removed a package from the Adam and Eve bag in my hands. I watched as I struggled with a pair of scissors to remove the Vibrator from the hard clear plastic around it, I was obviously impatient and had I been a little slower I would have gotten the desirable object out much faster. I quickly inserted some batteries and I could see my hand shaking as I turned it on and felt its movement for the first time.

I smiled.

On the bed I could see a pair of recently purchased never worn boxers, I lifted the silk band and inserted the vibrator within, the tip pointing towards the beds headboard, as if there was a real cock inside them.

We watched the empty bedroom in silence for some minutes, until finally the door opened, and I came through dressed in a White satin chemise with matching panties, stockings and suspenders completing the ensemble.

This was late in my fantasy time line and my makeup was much better, the lip stick a shocking Pink for a reason, I knew that vibrator would be fucking my face very soon, and I wanted a visible mark to see how much of it I had managed to cram down my throat.

I lay down on the bed and closed my eyes, my hand started to caress my body, massaging the muscles of my neck, moving slowly down, spending a little time playing with each of my still clothed tits. I lifted the Chemise up to my neck, my body now exposed as the foreplay got a little rougher, the mass of my tits squeezed, first gently, then roughly, then gently again, I imagined my phantom lover licking his lips around my nipples, his teeth leaving bite marks on my tits.

I rolled the chemise over my shoulders as my breath began to pant with excitement.

His hand moved lower and I lifted my hips to allow him to caress my ass, as he turned me over his first strike landed on my right cheek, the next on my left, I knew my ass was turning Red under the White silk and still the blows landed, one after another until each cheek had taken over a dozen blows, tears slowly rolled down my face and my mouth opened to allow the taste to heighten my masochistic pleasure.

Through the boxers I could see my lovers cock was now fully hard and ready for play, I expected my panties to simply be moved to the side as he took me in the first rush of his eagrness, but his control was better, I was rolled on to my back and his hand brushed my tits again, they wandered slowly down past my belly and ended were I so desperately want them. I could feel my clit harden as he expertly played with it, and I knew I would cum before he entered me if he continued unchecked.

I made no sound as I bent over him, my hand released his Nine inch cock and it stood erect and buzzing before me, tentatively I ran my tongue around the tip, then ran down its length and back up, it was the largest cock I had ever seen and I was slightly worried that it would be too big for me, but I had to find out, my mouth opened as I bent my head to take just the first few inches in. I felt his hand lightly on the back of my head, encouraging me to go deeper, his other hand rubbed lube on to my clit and around my pussy.

My panties had been removed and my legs were spread wide as I opened myself to be used. I could see how happy I was as a man played with me, readied me for taking, and I could see less of the length of the cock as my mouth accepted more of it into its welcoming depths.

The cocks speed picked up and I was no longer giving a blow job my mouth was being fucked, I watched as my body responded with pleasure, my hips raised and I quickly spasmed as an orgasm hit and my gushing juice flew along the length of my body.

A few minutes later my eyes opened, the long plastic vibrator lay beside me with lickstip masking its pristine beauty. I smiled as I realized I had taken almost the entire length, and rolled over to sleep in the imaginary embraced of the man who had just fucked me.