Jamie's Descent Pt. 01

Chapter 1

What did we do before social media? How did we manage to get through the day without that endless stream of dirty jokes, funny photographs, gossip and links to dodgy websites that now fill our lives? Yeah, yeah, I can hear you grumble. Get on with it, I can hear you say. Well, dear reader, it was one of those links that started me down the road to... oh, you'll find out soon enough. I was 18 and I had just come down to London from my hometown in Norfolk after leaving school.

A friend of my father's had offered me an internship in an office of a finance company for which he was the Finance Director. However, Wall Street it wasn't. Like millions of other office rabbits around the world, I shuffled papers, produced figures for reports that never seemed to get sent anywhere, made endless cups of coffee and kept the global economy humming along nicely. Charles Dickens would have recognised the office instantly.

Also like millions of other office rabbits around the globe, I discovered there is one thing that can keep us from going insane- email. It was a life saver. Relief from all the hours of tedium came in the shape of the messages that poured into my social media accounts. We had the usual warnings from the company about not using email and the Internet for your own use, but whoever paid any attention to that? Then, one day I opened one of my messaging apps.

Are you ready for this?

Be careful, this could really change the way you look at life.

Take the Ladyboy Quiz!

Bah, humbug, I thought. So I clicked on the link and up popped a series of pictures of girls naked from the waist up. Yes, of course, at that moment I closed it down and deleted it right away - not!

I scrolled down and there must have been 20 photographs, all of outstandingly beautiful girls. Blondes, redheads, Asians, black girls - all absolutely gorgeous. I knew what ladyboys were.

My elder brother had gone on a rugby tour a couple of years before to Australia with a stopover in Bangkok. He had come back with stories that made my hair stand on end. One story in particular had stuck in my imagination. One of the team had got very drunk in a bar and the other lads had paid for a bargirl for him. Except this was a very special bargirl.

After many pints and much prompting my brother revealed that he had been the guy they set up. He claimed he vaguely remembered this gorgeous girl taking him into one of the back rooms. He remembered her stripping down to her knickers before she stripped him and pushed him onto the bed. He claims she gave him the best blowjob he had ever had (I don't actually think he had that many before). My brother then maintained he had passed out.

Fair enough, except that at some point one of the guys had crept in and taken a photograph. A couple more pints and he pulled out a photograph from his wallet. It was a very poor quality shot, but it clearly showed my brother, stark naked on the bed, eyes closed and with a look of ecstasy on his face. Also on the bed was a gorgeous Asian girl who was energetically giving him a blowjob.

What was also obvious from the photograph was the fully erect cock sticking out from the girl's knickers, which she was stroking in one hand whilst clearly holding my brothers cock with the other. I clearly remember the feeling I had looking at that picture. I felt myself getting dizzy and my mouth was dry as I looked at the picture. I felt myself blush and my cock twitched as I held the picture in my hand. My brother then snatched it back and threatened to beat the living shit out of me if I ever told a soul about it. As he was 6 feet 4 tall and built like a gorilla whilst I was only 5 ft 7 and slender, I took him seriously. I had taken after our petite and slender mother and he after our built like a brick shithouse father.

We were called Little and Large by almost everyone and I got stuck with it as a nickname. Of course, in that perverse way people have with nicknames, I was Large and he was Little.

Six months later I headed to London, but I guess I had forgotten about the photograph until I saw the girls in this quiz. All you had to do was tick a box by each picture if you thought the girl was a ladyboy. Easy peasy, I thought.

Not so, as it was really difficult to tell. They were all stunning and in the end I pretty much ticked the boxes at random. At the end of the quiz it calculated your score and I managed to score only 3 out of 20 right. I couldn't believe it.

I went back through the pictures and that's when I think I began to remember my brother's picture. To be honest I remembered the feeling more than the picture. I began to feel dizzy and my mouth felt dry. I actually think I was rubbing the growing bulge in my trousers when my supervisor's voice made me jump out of my skin.

'James! What are you looking at?'

Vanessa, my supervisor had appeared round the corner of my cubicle.

'Nothing, uh, just some figures.'

I managed to blurt out. I closed the quiz down instantly, but I couldn't tell if she had seen anything on the screen.

'Anything interesting?' Was she being sarcastic? 'No, no, well, yes, it's the month end sales stats for your report.' I mumbled.

'Good, make sure I have those by this evening.' She turned on her heels and stalked down the corridor. Now Vanessa was the office Goddess. She was tall, may be 5ft 10 or so in her stiletto heels, which she wore every day. Somewhere in her background there must have been some Viking genes; long blonde hair, clear blue eyes and legs so long they went straight to heaven.

I had been put into her team from the start and for some reason she seemed to take against me. She would get on my case every time she could. Any small mistake would be blown up out of all proportion. Worst of all she somehow knew that I had got the job through the old boys' network and that seemed to wind her up even more. Frankly, I was a nervous wreck when she was around and I was planning to get a new job as soon as I could.

Over the following days I would go back to the quiz and look at the girls whenever I got the chance. One evening I was working late and was looking yet again at the girls when I spotted a link at the bottom of the quiz.

Click here to change your life.

I looked around but the rest of the cubicles were empty and I hesitated a moment but then clicked on the link. Surprise, surprise, it took me to a porn website.Ladyboy Heaven.Everything you wanted in a girl and that bit more the banner screamed out.

I checked once more, but there was still no one there. It was a pay site but there was a button to click for visitors. I clicked and the screen filled with an image of a beautiful Eurasian girl on her knees sucking the cock of what appeared to be another ravishingly pretty Asian girl. I began to feel light headed and I felt a flush creeping across my face. I could now see the first girl also had a tiny little cock which the second girl was stroking. I could feel the blood rushing through my veins.

I clicked again and again. Scene after scene of ladyboys sucking, fucking, and flashed across my monitor. My hand strayed naturally to my groin and I felt my cock harden as I hungrily took in every new picture. I lost track of time completely. My phone buzzed and I jumped clean out of my chair. I looked at the number and panicked. It was Vanessa's extension. I picked up the phone and tried to say hello, but my tongue felt like it was three times too big for my mouth.

'James, you're working late. Are my figures ready yet?' Vanessa's voice was calm and assured.

'Well, yes, I've just finished them.' I managed to say.

'Okay, well I'm still here too so email them to me and come to my office so I can see if they are alright.'

I wanted to protest but the phone had already gone dead. I quickly emailed the figures and walked around the building to Vanessa's office. It was in the executive part of the building and I had always wondered how Vanessa had managed to wangle an office here. It was pretty late now and the only office that was lit was Vanessa's. I stopped at the door and knocked.

'Come in James.'

Vanessa was sitting behind her looking at her computer monitor as I walked in. She waved a hand to the chair in front of her desk and I sat down.

'James, the figures are fine.' She still wasn't looking at me.

'Thanks.' I mumbled.'They're fine but it's not that I want to talk to you about.'

She turned to look at me for the first time, and her eyes seemed to glitter as she spoke.

'Yes, it's about something completely different. James, you are aware of the company policy on the misuse of corporate assets aren't you? Especially the unauthorised use of office technology?'

She smiled as she spoke 'Well even if you're not it doesn't really matter.'

It was about now that I began to realise what this about and my heart started to pound.

'You see James, we take the abuse of corporate IT here very seriously, and we have installed some very clever technology that allows us to monitor what our employees are doing on the Internet. I noticed that you were working late this evening and as a part of my responsibility I decided to check what you were doing.'

She was smiling sweetly as she spoke in an almost apologetic tone. I couldn't take my eyes from hers. I was as transfixed as a mouse in front of a cobra. I'm not sure I was even breathing by this time.

'James, can you explain to me what part of your role involves visiting an internet site called...' she paused and looked at the screen probably to drag out her enjoyment of the moment, 'Ladyboy Heaven?'

I swear I died at that moment. My mind blanked. All I could do was look straight into those eyes.

'James, I'm waiting.'

'I, I, I it was a mistake.' I blurted out.

'Yes, James, I think I agree it was a mistake for you to do this.' She said.

'No, No, I mean I just clicked on a link in an email from a friend and soon as I saw what it was I came back out.'

'James...' she sounded now like a teacher talking to a stupid pupil.'We both know that's not true, it's all here on the report.'

As she spoke she swung the monitor round.

'You spent over an hour on that site.' She paused for effect, 'Several times this week. Are you telling me it took you that long for you to work out what Ladyboy Heaven was? I took a look too, and it took me, oh, all of 10 seconds to work out that it's a website for people interested in having sex with boys who look like girls. James, are you into that? Is that why you visited this site?'

My eyes dropped to the floor, and I felt my face redden. My tongue was stuck in my mouth and I couldn't answer.

'James, do you want to have sex with girls with a dick? Is that it?'

She was relentless. 'Or is it that you relate to them? Do you really want to be one, James? Or should I call you Jamie?'

I blushed even more deeply and I stared at the floor. Her voice took on a different tone.

'Jamie! Look at me now!' she almost barked this out and my eyes flew to hers. 'Answer my question.'

'No, I mean yes, I mean, I don't know.'

I felt my blood draining away from my face and I shivered but I couldn't take my eyes away from hers. She held my gaze and I felt whatever self control I had left drain away. Her eyes seemed on fire and I felt a strange sense of power passing from me to her.

'Jamie, well we are confused then aren't we? Well, Jamie, let me tell you what I think you are. I think you're really a sissy boy. I think you're a cocksucker. I think you want to be subservient. I think you want to be a pretty little sissy who only wants to stroke and suck cock. I believe you want to be one of those girls on the website.'

Her words were roaring around in my head. I felt sick but I couldn't break eye contact.

'I've thought so since the day you started here. I have had my eye on you ever since then. Oh, you might not have realised yourself. I knew it when you opened that quiz. Oh, yes, I sent you that. It had a piece of code in it that tracked when you opened it, so I know just how often you went back to look at it. So I just added the website link to it and waited. I knew you would come to me eventually. I just waited and you rushed straight into my web.'

While she was speaking she stood up and moved slowly round the front of the desk until she stood over me. She slowly drew her index finger along my lips as she spoke.

'Remember, I have all the evidence I need to get you dismissed instantly from this firm and I would make damn sure any new employer would get to hear about your surfing habits. But, my little sissyboy, I think there is another way to deal with this. Yes, I know what you want Jamie. You want to serve me don't you?'

I couldn't believe it as my head nodded slowly in agreement. She pushed her finger past my lips and into my mouth. My lips seemed to naturally form around her finger and as she moved her finger slightly in and out I began to suck gently.

'That's so good Jamie. You know that feels do good don't you, Jamie.' She began to coo.

I felt so powerless, but so excited at the same time. I closed my eyes and continued to suck her finger.

'Keep your eyes closed Jamie.'

Her voice changed again. This time it was a voice of power, power that should not be contradicted. I felt a touch on my trouser zip and I couldn't stop my eyes opening.

'I told you to keep them closed didn't I?' she barked.

Her hand caught me across the face and I recoiled from the sting of the blow.

'Do as I tell you!' she almost snarled.

I snapped my eyes closed again. I felt myself slipping deeper and deeper into darkness. Her finger returned to my mouth and I started to suck again. I felt her other hand again touch my zip.

'My, we are excited by all this aren't we Jamie? I can feel you are really enjoying this.'

Her hand kneaded my cock and I couldn't help squirming in the chair as I sucked her finger and she stroked my now painfully constrained cock. Whatever was left of my self control had now vanished. Instead, I felt strangely at ease, now that I had totally surrendered to the power of this woman.

'Jamie, look at me now!'

As I opened my eyes she slipped her finger out of my mouth. Her eyes bore into mine and she brought her face right in front of mine. Her lips brushed mine and her tongue darted out and past my lips. She continued to rub my cock as her tongue probed the inside of my mouth. Her eyes remained locked on mine all the time.

She drew back and once more slapped my face. It stung so hard I began to whimper. All this time she had continued the pressure on my cock, rubbing and caressing it and I ached for release. She stretched out her hand again and I tensed for another blow. Instead, she caressed the cheek gently with her fingertips and spoke softly again.

'Jamie, if you displease me I will punish you again, but if you serve me well I will allow you to live your wildest dreams. You will learn the pleasures of serving me and you will understand the ecstasy of fulfilling your true destiny. From now on when we are alone you will address me as Miss Vanessa, is that clear, Jamie?'

I nodded. Another sharp pain jolted me as she again slapped my face.

'You will also feel the pain of serving me if you don't do as you told.'

'Yes, Miss Vanessa.' I whispered.

'Better Jamie, but remember in future, I don't want to hurt you too much.'

She moved back from me and for the first time I paid attention to what she was wearing. Normally she wore skirts and blouses together with her signature stilettos. Tonight she was wearing a trouser suit, and as the jacket was double breasted, it gave her a slightly masculine look, yet she still wore stilettos beneath the trousers.

'Kneel, Jamie. my little pet,' she ordered and I slipped from the chair to my knees.

'Now close your eyes again.'

I did so and felt her tie something over my eyes. I instinctively brought my head back and received a slap for my effort.'Jamie, you must learn to trust me. Part of serving your mistress well is to trust that she knows what is best for you.'

How quickly had I slipped to this point? It seemed only minutes ago I had been happily staring at that damned website and now I was on my knees in front of a woman who wanted me to be her...what? Servant? Slave? I shivered with fear and anticipation.

'Yes, Miss Vanessa.'

'Jamie, I want you to remember what you felt when you looked at the pictures on the web site. What you felt when you saw those ladyboys take a cock past their lips and to lick and caress it until it becomes as hard as granite. Try to imagine what it is like to kiss the tip of a prick and to wrap your lips around it and to feel that hard shaft begin to slide its way into your throat. To feel the warmth of the cock as you worship it so that it fills your mouth. You want that feeling, you need that feeling, you want to serve that cock, to savour its taste and feel it move and live between your lips. You want to feel the power of a cock as it takes possession of you and you want to feel it twitch as you make love to it. You want to feel the veins as the blood surges into the cock; you want to feel it slide in and out of your mouth slippery with your saliva.'

I was so caught up in the imagery she was describing that I moaned. At that moment she slipped her finger back into my mouth and I began to lick and suck it hungrily. She slipped the finger deeper and deeper into my mouth until my mouth was being finger fucked. She added a second and third finger until I felt my mouth stretch. I couldn't stop. I had to be possessed by her.

She suddenly withdrew her fingers and I felt lost. I wanted that feeling back in my mouth. I suddenly felt something quite different against my lips. Not her fingers. Something bigger, something far more solid than Vanessa's fingers.

I reared back but Vanessa's hands clamped around my head and forced me back.

'Do not be afraid, Jamie. This is the start of your sissy training. Thats what you want to be isn't it? A perfect little primped up sissy, serving me in whatever way I want. Isn't that right Jamie?'

At that moment Vanessa took off the blindfold and light flooded back into my eyes. As my eyes came back into focus I saw Vanessa standing there before me like a Nordic angel; long blonde hair cascading around her shoulders but with what looked like a large penis standing proudly from her now unzipped trousers. My eyes bulged as I took in the unbelievable sight. She towered over me, holding the back of my head with both hands.

'Jamie, Jamie, don't worry my little girl. This won't hurt at all. Relax my angel. Let your feelings show you the way.'

Her voice was so soothing and she ran her hands gently through my hair. She gradually drew my head towards her groin and I could see that it was some kind of strap on dildo she must have had concealed in her trousers. My lips brushed against the tip of the dildo and somewhere deep in my subconscious a small voice whispered no. My senses were reeling yet somewhere in the midst of my confusion I knew what I had to do, even wanted to do.

The pressure from Vanessa's hands increased and the dildo began to slide between my lips. All resistance vanished and I began to lick and suck my way along the length of the shaft.

'Oh Jamie, that's so good baby, Suck me, Jamie. You know you want to do this so much.'

Vanessa's voice seemed to come from so far away as I took more and more of the dildo into my mouth. She began to move her hips gently and the shaft began to move in and out of my mouth. I had surrendered myself completely by this point. All my being was centred on what I was doing with my lips and mouth.

'Baby, that's so wonderful. Suck my monster, wrap those lips around that cock.'

Vanessa softly encouraged me and her hips began to move quicker and the dildo moved faster in and out of my mouth.