Thursday, 10 June 2010

II: James' Crossdressing Fantasies

Chapter Two: The Journey

'...this.'

As I came round I tried to work out what had happened to me. My eyes were tightly shut as I groggily processed my situation... I must have fallen unconscious. I could feel that I was sitting upright and the cool breeze on my face suggested I was outside. Something was restricting my movement across my chest, and I was vaguely aware of something flapping about my legs. I heard the faint sound of an engine and suddenly the wind intensified, picking up my long hair and flicking it wildly.

'since when did I have... long hair?! Oh God... NO!!' Everything came flooding back to me and with a sense of urgency I squeezed my eyes open.

Shit. I opened my eyes to the sight of a vast motorway stretching out through the windscreen of my girlfriend's top-down convertible. A look down at my lap confirmed my worst fears - I was still wearing the dress I had on when I fell unconscious and it was billowing around my legs. Shit! As I snapped my hands down around my knees to hold it in place I received another shock - my fingers now had long, red nails at the ends of them. Below the skirt of the dress I could see I had two strappy red heels on my feet and similarly painted toenails.

Fully awake now, I turned to my girlfriend, panicked at what was happening. How did I get in her car? Why did she drug me? I tried to speak but my throat was bone dry. When she noticed me all she did was smile coyly, wink, and shout, "You're awake! Y'know, you never did tell me before - how do you like your new look? I made a few additions before we set out - I hope you like them!"

Kate had changed too since she drugged me. She was now wearing a dress identical to mine in a stunning bright blue; she seemed unfazed as the wind toyed with it about her legs, instead staying focused on the road. Her hair had been styled so that it was now slightly curly, and flowed down around her shoulders in a similar brown colour to mine. In fact, everything about her mirrored what I was wearing, from her bright blue nails to the make up she'd applied to her face. Kate noticed me looking her over: "Ooh, do you like it? The dress was on offer and I couldn't let you have all the fun... so I bought one for me, too! Then I had the idea of us wearing matching outfits - how cute is that!?"

How could she be so casual!? I desperately searched for an escape from the situation - some way to regain control or hide from the onseeing eyes surrounding me. Frantically looking around, I realised I didn't even know where I was; I didn't have a phone, or ID, or anything other than what I was wearing. I just wanted to hide; I could feel the wind blowing around my smooth, shaven legs; the material of the dress was brushing over my knees and thighs and made them tingle. Why did Kate have to drive the car without its roof!? I felt so exposed... but somehow I couldn't help being turned on by the situation even though my blood was racing with fear.

I caught a glimpse of myself in the side mirror and saw the familiar reflection that had so taken me by surprise before. I was a stunning, heavily made up brunette with long, flowing hair that was now being blown around behind my head and slightly across my face. I awkwardly reached up and brushed the hair out of my eyes, worried that at any moment the wig might be lifted off my head by the wind. As I did so the material of the dress whipped up wildly, revealing slightly the hot red panties I was wearing underneath. My girlfriend giggled at my embarrassment - "Don't worry, we'll be on slower roads soon. Just relax, we've got a fun weekend ahead of us!"

My heart was in my mouth as I managed to choke out a response, "fun.. weekend!?" She quietly nodded as she kept driving, and then motioned to the back of the car. Confused, I turned to look over my shoulder. There, on the back seat of the car, was a large, pink suitcase that I had never seen before.

"That's right, after you told me about your secret I packed a load of my things for us to share for our weekend away! Don't worry though, that dress is yours to keep - and there'll be plenty more where that came from!"

What was she playing at? Was this some kind of twisted revenge before she broke up with me? My mind was racing with all the worst case scenarios - what if she'd taken pictures? What if everyone was waiting for me at our destination? Whatever my fate, it was well and truly in her hands and I was really scared.

It wasn't long before we took a slip road off the motorway and I was relieved as the car slowed down and the wind started to calm. I finally plucked up the courage to confront my girlfriend.

"Please, just take us home. I really don't want to be seen like this in public!"

"Relax, look at yourself! Don't you think I did a good job? You're almost hotter than I am!" She sighed at my obvious unease and briefly took my hand, which was still scrunched into a tight fist in my lap.

"Look, we're almost there now and I've put a load of effort into planning this. You're going to enjoy it, trust me."


"Wh-where are we going?"

"It's a surprise. You'll find out soon enough."


As we started to drive through some town areas the wind became far less brutal, but with it came new problems to worry about. There seemed to be pedestrians everywhere - and they could all see me! Every time we stopped I looked pointedly at my feet and the minutes seemed like hours as I willed the car to move again. For a while there was a sports car following close behind us, and I accidentally caught the driver's eye a couple of times in the mirror. As mortifying as that was, there was worse to come. We pulled up at some traffic lights and, to my horror, the car behind pulled up alongside, waiting to turn left. The driver brazenly wolf-whistled, and my girlfriend smiled and winked at him. She nudged me to say something but I sat perfectly still, staring at the floor. He was mere inches away from me and I was sure that any moment he'd work out I was a guy. The lights finally changed, and as the car tore away from us I heard the driver shout, "Lighten up, sweetheart!" My face was burning with embarrassment as my girlfriend whispered in my ear, "looks like you're making friends already!"

The rest of the journey was as uneventful as it could be given the circumstances. I was a hostage to my own girlfriend and in a body that didn't feel my own. By now I had figured out that the wig was somehow attached to my head; and as I thought back to the wet feeling around my scalp I realised it must have been glued onto me! With this came another realisation - the breast forms were glued on too and I had no access to the solvent. I was trapped in my own fantasy and I was filled with about 10 emotions at once. I felt a potent mixture of sexual excitement and unadulterated fear to which nothing in my past 19 years on Earth could remotely compare.

Any attempts I made to relax were abruptly put to an end as Kate took an unexpected left off of the main road - we were pulling into a hotel! As we rolled into the car park the reality of my situation hit me. There was no escape - no clothes, no ID, not even a way back home. Even as we pulled into a space I was willing Kate to turn around and drive out - for this all to be a prank or a lesson to snap me out of dressing. I felt sick to my stomach as my girlfriend turned off the engine and stepped out of the car.

"Honey, could you grab the suitcase? I'm going to go inside to sort out our reservation."


She shut the car door and tottered off into the hotel.

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