Blossoming Shemale Ch. 01

This is the first time I've tried to write in the first person. I may have slipped up a couple of times, but I've tried to keep it consistent.

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale if you enjoyed it, I hope you'll enjoy this series.

My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to prove it now, and to be honest, I didn't really have the desire. That was all before. I have to accept the now, and when I'm truly honest with myself, I relish the now. I'll try to tell you my story, the important parts as I've come to identify them. Let me take you back...

I parked my beamer in one of the few spaces left in the office car park. It wasn't technically my space, but slowly, everyone else had learned to leave it free. If you had more power than I in the office, then you had your own named space. I wasn't quite there yet, but I wasn't far away, and I was an assassin in back room politics.

I'd graduated with an Accounting degree, just like my father. He wanted me to make it, while not on my own completely, under some of my own steam. So he'd set me up with an entry level position at the firm he'd left to start his own. Obviously he still had a bit of pull around the place. Since then, over the last few years, I'd risen until I was just short of the top echelon. I wasn't quite a salary partner, but in the next round of promotions, I expected to make it. Then in another year or so I'd make equity partner, unless Dad gave up on his silly notions of me working for a living.

As I took the lift I thought ahead to my day. My secretary had told me that I had a ten o'clock meeting with a couple of new clients. There'd been rumours around the office about them, but I'd never managed to really catch the gossip, and my subtle threats hadn't yielded results on the grapevine either.

I was looking forward to tomorrow, Friday night drinks. I was pretty sure I'd finally manipulated Christie, my secretary, to the point that I'd finally get inside her tight little panties. She'd been the hardest to manipulate so far. Usually after a few months I bedded them, used them for a good eight months or so, then slowly moved them on. So far nothing had gone wrong, I'd heard nothing from HR or anything in the rumour mill.

Christie was wearing her grey pant-suit today. Normally pant-suits did nothing for me, but hers was so tight across her tush that I immediately forgave her. She handed me my coffee and followed me into my office, letting me know that Ms Harriet Hille and Miss Dixie Starr, (what an odd pair of names, Dixie Starr sounded like a porn star), would be here in about half an hour. He'd read their file. They were a pair of entrepreneurs apparently, having started up some business a couple of years ago, and now reaching the point where they wanted to protect themselves financially, and find the most beneficial structure. For some reason they had been referred up the chain to me. The file didn't mention any particular financial or tax issue for referring the file upwards. I'd just have to wait and see in the meeting.

In the meantime I enjoyed my coffee, Christie really was great at that, and I wondered to myself if keeping her on just for the coffee might be worthwhile. The sex would really be the determining factor. I imagined that with that little tush, her arse must be fantastically tight, and I felt my cock stir at the thought. I was reaching the point where I would be expected to be married soon, to further my career. I groaned at the thought though, I'd seen it bring too much trouble to a lot of people around me, especially my father and a lot of his friends. I'd have to be smart about it when the time came.

Christie buzzed me then to tell me my potential clients had arrived.

Ms Hille was, as I expected, the older of the two. I guessed her to be about middle age, maybe late forties. She was Caucasian. Her makeup was tasteful, her lips a creamy pink colour and just a little rouge and eye shadow. She was about 5'10" I guessed, without the heels that were currently providing an extra 3" or so, slightly taller than my own 5'9", but right now, with her heels she was taller than me. I'd never been tall, but something about her made me wish I was taller right now. I had been prepared for two women, but not necessarily attractive ones. She had light blue eyes, almost ice, quite open and expressive though. Her nose was just edging towards being a little long but as it was it gave her a striking look. Her hair was a fiery red and hung straight down to the middle of her back. She was dressed in a tight, black, strapless dress, from just above her knees, with a short fur coat over the top, with fur around the neck and cuffs. Her shoes had 3" or so heels, and were zip up suede. Overall she was quite attractive, though a little intimidating. Her bust, constantly my weakness, was pretty impressive, at least a D cup, possibly more. She had a modest amount of cleavage on display. I'd have guessed she would weigh about 90lbs or so, solid, but suited to her height, and certainly not overweight. Her hips flared a little, as did her arse, but her real selling point or points were definitely her tits when it came to her body.

Her business partner, perhaps more, but so far I only knew them as business partners, Miss Starr, was certainly a contrast, and much more racy. She did nothing to assuage my first impression from her name, thinking that she had a porn star's name. She looked to have some Latin genes as her skin was darker. She was younger, young in fact, she could pass for a late teenager, but was probably in her early twenties. Her makeup was just shy of slutty, deep red lips, rouge, green eye-shadow above thick, long lashes and brown eyes that were almond shaped and smoky. She was definitely trying to highlight her high cheekbones, and her nose was small and quite cute. She was shorter than me in her heels which were about 4", so I guessed about 5'4". Her hair was a dark brown, and just below her shoulders with a bit of a wave worked into it. She had on a green, pleated skirt, about halfway up her thighs, and knee-high black leather boots with a thick heel. She wore a black halter top, exposing her midriff and a small green gem in her navel. This was all revealed when she opened her long, dark grey coat. With it buttoned, Ms Hille almost looked like the racy one. Her tits compared pretty well to Ms Hille's also about a D cup, possible a little smaller than Ms Hille's. There was a little more cleavage on display, but still tasteful, just. Her hips were wider than Ms Hille's, and I was willing to bet her booty popped better than Ms Hille's. When I took her coat, it was confirmed. She had a tribal tramp stamp in black, and her booty hung out there mouth-wateringly. She was sexy, no doubt about it. I'd love to shove her over my desk and plough her pussy with my truncheon. But I had work to do, and these were clients, not sluts, or at least, clients first, and maybe sluts later I hoped.

We discussed their business and it became clear to me they had a partnership of synergy. Miss Starr seemed to be the creative one, while Ms Hille was all about the business and the details. They'd been operating for a couple of years and had used a friend of Ms Hille's to do the financials, structure and taxes. He'd recently told them that they were getting beyond his expertise, and he didn't want to cost them anything by missing an opportunity or weakness due to his limited knowledge, so sent them on to my firm, as he knew a couple of people that said good things about us.

They ran a business that operated as a combination health spa, nightclub, beauty parlour and a couple of other items I missed. It was an unusual combination as far as I could tell, but they dodged a few questions, and I could tell they were keeping secrets. We'd had a previous client at the firm that ran a nightclub, and we had almost gotten hauled in by the authorities until we managed to convince them that we'd been unaware, they'd kept their illegal dealings hidden from us. It had left the partners hesitant to take on those sorts of clients though. This was probably why it kept getting referred up the line and landed on my desk.

Neither one of them had much accounting or tax knowledge so I had to explain a few things to them at a basic level. This frustrated me a little, since I'd left behind these types of clients years ago. I think they picked up on that, and the meeting became a little frosty.

I gave them some general advice, suggested changing their structure to assist them expand into other locations, but I knew we wouldn't be taking them on. I needed the promotion and a client like this would not make me look good to the partners. I didn't tell them that though. I told them I'd give them a call in a few days to tee something further up.

By the time they got up to leave, I don't think they thought very much of me. In fact, as I escorted them from my office I'm sure I heard Dixie Starr mutter something about me being stuck up, while Harriet whispered something about taking me down a peg or two.

It was a terse meeting, but I'd had them before and didn't think much of it. Christie though was trying to hide a grin from me as I returned to my office. That confused me.

I sat at my desk and wondered what to do. The trouble with the last 'club' client had been pretty big. Ms Hille and Miss Starr would need to be dealt with in some way, nothing sinister; merely letting them know that we couldn't help them would suffice. Then I had a brainwave. I could really display some ethics if I was proactive. I decided to call the authorities and leave an anonymous tip about the women, state that I thought there might be some illegal activities happening. That should impress the partners.

On the Friday a week later I was again looking forward to drinks after work. Christie had dodged me last week, but she wouldn't this week. I was really hanging out to get my dick wet. Dixie Starr and Harriet Hille were far from my mind, and I was really looking forward to my promotion. I'd even received a call from my father to congratulate me on my progress, which I took to mean my promotion was on the way, and hopefully soon I'd be able to change over to Dad's firm and leave the cushy life.

At the pub, Christie still managed to put up a good fight. She hadn't left though, and pretty soon there were only about five or six of us left. Christie suggested we hit a club, and the consensus agreed, so off we went. I knew I could wear down her resistance at the club.

I'd had a few by this stage, so I wasn't really picking up all the details as we transferred over, but I was still in control, and still felt that I could charm Christie. I felt a niggle in my brain when they said the name of the club, but I wasn't really focused.

The last thing I remember of that night was Christie's face. She was smiling at me like she knew the punch line to a joke I was telling, and it seemed like she was rising above me...

When I woke up I was cold, and my head was pounding. It must have been a busy night. I reached over to the other side of the bed to see if I'd been successful with Christie, but instead I felt the wall. This wasn't my bed. I tried to open my eyes, but they were so dry and they felt sandy. But the realisation of not being in my own bed pushed me on.

I was in a single bed, more of a cot really. I couldn't remember ever having slept in something so small. Above me was a window, but it was only muted light coming in. The walls were an off-white colour, but clean. The wall at the foot of the bed looked like one of those two or one-way mirrors you see in cop shows, I always get the one/two way thing mixed up. The wall opposite the bed held the door, and an average sized TV mounted to the wall, high up. The carpet looked short, and was a creamier colour than the walls. That was it. Was this a cell? It didn't look like a bedroom that's for sure. The mirrored window worried me, and I could feel a creeping panic.

I pulled back the duvet, which was surprising thick. I realised that's the only reason I was warm, as I discovered I was pretty much naked. What I was wearing, was a thong. I could feel the material up my bum crack. It was sizes too small though. I'd always been pretty proud of my dick. I was a good nine inches hard on a good day, and thick enough to get the job done. I looked down at my crotch. My cock was stuffed inside the pouch, but it wasn't up to the job of fully concealing me. Part of my nut sack was squished around the sides, and even part of the shaft bulged out. It was, of all colours, pink, and spandex. I'd never have been caught dead in something like this. Usually I wore boxers, occasionally briefs, but always muted colours. Why was I dressed this way?

Where was I? I stood up, feeling extremely self-conscious, thinking of who might be watching. "Hello?" It was basic, but hopefully it let someone know I was awake. I walked over to the door, trying to cover my privates with my hands. I tried the door and the handle turned. My relief was palpable. I was worried I was locked in here. Still didn't explain why I was dressed like this though.

Then I tried to actually open the door, but it wouldn't move. I could see the latch withdrawing, but it must have been jammed. I decided to give it a hard pull to un-jam it. The handle came off the door. "What!?!" I could feel the panic again, but I tried to maintain my calm. I looked at the door. Obviously the latch had closed again. I tried to put the handle back onto the shaft, but instead I pushed the shaft through and pushed the handle off the other side. I heard the thud of it hitting the ground. I could actually look through the hole in the door now, like looking through a key hole. Outside looked like a hallway, it was dankly lit, and I couldn't see anything of use. I moved my mouth to the hole and called out louder this time, "Hello?"

Again, no response, my calm was slipping now. I stood up, feeling the thong shift along my crack, and my cock and balls shuffle around uncomfortably. I no longer bothered trying to hide myself though. I looked at the window. It was obviously an external window. There were closed shutters, which glowed like daylight was being held out. I stepped quickly to the mirror and knocked, "Hello? What's going on?" but still not a sound in response.

Finally I yelled, "IS ANYBODY THERE!?!"

Over the next few hours I tried a lot of yelling, until I was hoarse in fact. I tried opening the door, cutting my fingers on the mechanism getting the latch open, but I'd finally come to realise that there was a bolt or two that I couldn't see. I'd thrown myself bodily against the door, the mirror and even tried against the window, despite how high up it was. Everything was pretty solid though. Once I stopped jumping and trying to injure myself, I got cold, and sat on the bed, wrapped in the duvet, depressed and scared.

Eventually, I noticed the light dim, and the glow around the shutters dim. Night was falling. I didn't think I'd be able to sleep in this situation, and I had that thought right up until I fell asleep.

I think it happened in the middle of the night to disorient me. Being locked up was disorienting enough though.

I woke up to the duvet being pulled off of me. I opened my eyes only to be blinded by a bright overhead light suddenly firing to life.

"Ooh, he's cute. He's going to be stunning." The voice was strange, sort of both feminine and masculine at the same time, like a woman trying to sound manly.

"Who's there?"

"I'm your new best friend darling." I felt someone sit on the edge of the bed, and I felt bare skin rub my arm where it lay above the duvet. The cot depressed heavily, whoever sat down was definitely big. "I do so hope we're going to be friends."

"Where am I?"

"This is a special place, where we make dreams come true." There was an undertone of humour there, and sarcasm. I was very, very afraid.

"I want to go, I want to go home." I still couldn't see.

"I know you do. You all do at first. And some eventually do get to go home. But a lot end up not wanting to. I wonder which one you'll be."

"Why am I here?"

"Well now, that's a very good question, and an interesting one. Some work out quickly why they're here. Some never even ask. Usually the answer is pretty straightforward. But for you, the answer isn't so easy. I don't know all the details honestly, but I gather you upset some people, and they found out about some very upsetting behaviour you've been up to. You've been womanising, using women, abusing your position of power with your secretaries. Then you used your power to make sure they stayed quiet. Does that sound familiar?"

She was talking like she was from the mob or something. I'd never been involved with the mob in any way. Upset some people? Who? Upsetting behaviour? What behaviour? Using women, womanising? Sure I can't deny that, but why did that get me here? Abusing power? That felt like a stretch. Sure, maybe, but surely nowhere near as bad as half the people in positions like mine. Making them stay quiet? That was mob talk; I'd never done anything like that. I'd made sure some of my secretaries left with large severance packages, I'd paid off another, is that what they meant? What was going on? What should I say? I should say something.

"I'm... sorry? I'm really, really, sorry." It had gotten me off as a kid when my dad wasn't happy a lot of times.

But it only made her laugh, again it was strange, a girly titter, but with something else there. "You have no idea. And you have no idea how truly sorry you're going to be." She paused as if waiting for something. I wondered what was going to happen to me. I still didn't really know anything.

Up until this point, I'd been scared, with no real idea what was happening to me. My first clue was about to bloom before me.

My eyes were finally adjusting. On my bed sat a form, large, if I had to guess, I'd say maybe six and a half feet tall, and built. Her face was silhouetted in the light, so I still couldn't see that. She was facing away from me looking down at me over her shoulder. She looked naked. Her waist narrowed and her skin, to my eyes, was flawless. She must have realised I could see now, "Well hello there cutie. It's time we got started. I have to tell you, I'm really going to enjoy this."

She stood up and turned to face me. Hanging between her legs was a cock. She was a shemale, a transsexual, a dickgirl.

I have a high sex drive, but not much luck with women when I'm not manipulating my secretaries. I'm not completely inept, but I certainly don't score with enough women to satisfy my desires. So I watch porn. My absolute fetish is big tits and I have bookmarks and gigabytes of porn covering my obsession with huge breasts.

It started really slowly. I often checked out illustrations and manga of big titted girls. Occasionally, unknowingly, they'd turn out to be shemales of some type. At first, that would put me off, and I'd browse away from there. Later, I started not to notice. If a girl had a nice set of tits, then her cock didn't matter. Eventually though, I found myself looking at their cocks as well.

It wasn't a desire, and it wasn't something I looked for, but in the right circumstance, I'd checked out the odd bit of tranny porn.

I had never been confronted with one before now though.

She stood there looking at me, in all her nakedness, and must have liked what she saw, because I could see it hardening. It wasn't overly big. What worried me was she was physically big. She had me beat on muscle, weight, and she looked like she could handle herself in a fight. Her muscles weren't exactly bulging, she wasn't a body builder, but it didn't take much to have me beat, I'd never really been one for the gym, I'd just had one of those lucky metabolisms. Her breasts were probably a C cup, and her cock looked about 5" long. I had a pretty good idea where this was leading to. I was scared.