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Rory awakes to a surprise...
My first attempt at a TG Cap - this is a photo of Jenny Chu. When I stumbled across it it just seemed to be shouting to be tagged...
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.
I: James' Crossdressing Fantasies
Chapter One: The Transformation
"So James, are you ready to get started?"
I could hardly believe my luck. Just days ago I finally told Kate my secret. I sat her down and told her straight about how I loved girl's clothes and the feel of them when I wore them. At the time she had quietly nodded and listened; there was no outburst, no anger or disgust. In fact, there wasn't anything at all. She just sat there quietly and let me pour my heart out, then hugged me and walked away. I assumed that was it; she had accepted my secret but had no desire to be a part of it.
But that all changed this morning. I was softly awoken by Kate and greeted with an unusual "Morning, sexy!". As I slowly came to my senses I heard her whisper in my ear, "how would you like to be a girl for the day!?" Without another word, she hauled me out of bed and led me to the bathroom. We had showered together before, but this time she had other things in mind! Once the shower was nice and warm she produced a razor, and she winked at me before crouching down and getting to work on my legs. Part of me was terrified about how I would explain this to anyone that noticed, but the far larger part of me was incredibly excited and wanted to see where this was leading!
After a long and unforgettable shower, Kate disappeared into the bedroom whilst I dried myself off. My underwear was nowhere to be seen, and as I made my way into the bedroom my jaw dropped. Spread all over the bed were the sorts of clothes I had only ever dreamed of! How was this happening? I had been so sure Kate's reaction was to take a back seat in all this, but now here I was; her standing opposite me with all manner of girly things spread over the bed, offering to spend the afternoon making me over. What had I done to deserve this girl!?
"Lookin' good girl! Your legs look smooooth." I felt myself blushing hard as she approached me. "How does that feel?" She asked, slowly working her hand up my newly shaven legs. I was shocked by how smooth they felt when just moments ago they had been covered in hair. Then she handed me a pair of red panties.
"Let's get that covered up," she said, looking pointedly between my legs. "Every woman needs a reliable pair of panties!"
If I was red before I felt like my face was on fire now. I meekly stepped into the garment and pulled them up, tucking myself in so everything fit snugly. Kate smiled and guided me into a chair at the front of the room. I was sat at a small desk with a mirror and a vanity case on the side. "Now, if you want this to work you're going to have to trust me. Close your eyes," she whispered, "this may take a while."
I sat with my eyes closed as I felt her prodding and dabbing at my face with various different types of cosmetics. I always admired Kate's profession as a stylist and make-up artist. She always made her customers look and feel so beautiful. Even so... what could she do with me? I'm a guy. Make-up can't cover that up, can it?
I felt Kate applying a generous amount of lipstick to my lips. Then, without warning, she started plucking my eyebrows. Ouch!
"Sit still!" She hissed, "it'll take twice as long if you flinch." Once that painful procedure was done, I felt her curling my eyelashes; and she also dabbed something onto my eyelids. The whole thing was surreal - I sat there feeling all manor of things being smothered over my face with no idea what they were or what they looked like. By the end I felt like I was wearing a mask.
"Now, I've had to wash this especially for you and its only had an hour to dry so it might feel a little wet..." Confused, I sat perfectly still as I felt something lowered onto my head. As it pressed down over my hair I felt a wet sensation; and I also felt damp hair running down my back and the sides of my face. I felt hot air from a blow dryer being blown all over the wig; she expertly guided the air to where it was needed until the wig was bone dry. I heard a small thud from the desk before she told me I could open my eyes. I excitedly awaited my reflection as I did so - only to see that she'd turned the mirror face down! "No sneak peeks," she said, "you'll get to see yourself when I'm completely finished." She spun my chair around so I was facing the bed and picked up two fairly large prosthetic breasts. She giggled as she applied some glue to the back of them and thrust them towards me. "Here," she said, "I'll let you choose where these go!"
"But... how will I get them off?" I asked apprehensively. "Oh don't worry, the glue isn't long lasting. And I have this solvent, just in case. Now what did I say about trusting me..." Still nervous, but slightly reassured, I slowly pressed the left breast into my chest. The glue felt cold against my skin, and Kate reached across and held it in place with her hand so I could put the other one on too. I sat like this for 10 minutes, with Kate straddled over me pressing the breasts onto my chest as the glue dried. The only items now left on the bed were clothes; and I was delighted to see amongst them was a silky looking dress that was a bright red colour. Kate first picked up the bra and, knowing I wouldn't be able to put it on myself, she ordered me to stand up so she could attach it from behind.
For a moment everything seemed to go in slow motion. As I looked down at myself I saw a woman's body - slim, completely shaven and wearing nothing but some panties and a bra. With the forms concealed there was no telling that they weren't real breasts - they'd even begun to warm up and feel slightly real!
"OK, time for the main part of the transformation! That dress is brand new; I picked it out especially based on what you... 'like'." I felt myself blushing again as I thought back to the part where I'd told her about my dream of a silky, frilly dress. She smiled at my obvious excitement as I hurriedly held up my arms. Kate approached me and she rolled the dress up slightly before lifting it above my head. I took a deep breath as Kate let go, and felt the garment slide its way down my body. The straps came to an abrupt stop at my shoulders and the skirt danced playfully around my knees.
It was perfect. As Kate tied it up at the back it tightened slightly around my chest, hugging to my body and the fake breasts. I took a step forward and relished the feeling as the dress stroked my legs. I couldn't resist swinging my hips a little - this was even better than I had imagined! I heard Kate lifting the mirror up behind me. The moment of truth. I don't know why, but I was dreading this part. As I turned around I imagined the look of a badly made-up guy in a dress and it made me cringe.
But Kate was right when she told me to trust her. Standing in the reflection of the mirror was a tall, attractive woman. My face looked completely feminine; I was wearing mascara and deep red lipstick as well as having curled eyelashes and slightly blushed-looking cheeks. My newly plucked eyebrows were thin and extremely feminine. My hair was a deep brown and, now dry, it flowed right down to my shoulders where it sat, partially obscuring the straps of my dress. My body looked amazing in the dress - from my large breasts it hugged my slim physique and playfully wrapped around my legs; showing off my smooth, shaven shins. Wow. This was beyond a transformation - it was like a second body!
My girlfriend produced a bottle of wine and poured us both a glass. She handed me one and said, "to your first step of living out your fantasies!" Not quite sure of what this meant, but excited nonetheless, I raised my glass to hers and slowly sipped the wine until it was empty. Kate just watched and smiled, and we sat there in silence enjoying the results of her latest project. After I finished my glass, Kate took my hand.
"You might want to sit down," she advised. As I moved over to the bed I started feeling groggy; my eyes were drooping as I struggled to stay focused on the image of my girlfriend stroking my face and gazing at me with her beautiful brown eyes.
"Wh- what's..."
"Shhhh" she whispered. As I slowly lost consciousness the reality of the situation hit me.
'Must... stay awake. Can't... let anyone see me... like........'
"So James, are you ready to get started?"
I could hardly believe my luck. Just days ago I finally told Kate my secret. I sat her down and told her straight about how I loved girl's clothes and the feel of them when I wore them. At the time she had quietly nodded and listened; there was no outburst, no anger or disgust. In fact, there wasn't anything at all. She just sat there quietly and let me pour my heart out, then hugged me and walked away. I assumed that was it; she had accepted my secret but had no desire to be a part of it.
But that all changed this morning. I was softly awoken by Kate and greeted with an unusual "Morning, sexy!". As I slowly came to my senses I heard her whisper in my ear, "how would you like to be a girl for the day!?" Without another word, she hauled me out of bed and led me to the bathroom. We had showered together before, but this time she had other things in mind! Once the shower was nice and warm she produced a razor, and she winked at me before crouching down and getting to work on my legs. Part of me was terrified about how I would explain this to anyone that noticed, but the far larger part of me was incredibly excited and wanted to see where this was leading!
After a long and unforgettable shower, Kate disappeared into the bedroom whilst I dried myself off. My underwear was nowhere to be seen, and as I made my way into the bedroom my jaw dropped. Spread all over the bed were the sorts of clothes I had only ever dreamed of! How was this happening? I had been so sure Kate's reaction was to take a back seat in all this, but now here I was; her standing opposite me with all manner of girly things spread over the bed, offering to spend the afternoon making me over. What had I done to deserve this girl!?
"Lookin' good girl! Your legs look smooooth." I felt myself blushing hard as she approached me. "How does that feel?" She asked, slowly working her hand up my newly shaven legs. I was shocked by how smooth they felt when just moments ago they had been covered in hair. Then she handed me a pair of red panties.
"Let's get that covered up," she said, looking pointedly between my legs. "Every woman needs a reliable pair of panties!"
If I was red before I felt like my face was on fire now. I meekly stepped into the garment and pulled them up, tucking myself in so everything fit snugly. Kate smiled and guided me into a chair at the front of the room. I was sat at a small desk with a mirror and a vanity case on the side. "Now, if you want this to work you're going to have to trust me. Close your eyes," she whispered, "this may take a while."
I sat with my eyes closed as I felt her prodding and dabbing at my face with various different types of cosmetics. I always admired Kate's profession as a stylist and make-up artist. She always made her customers look and feel so beautiful. Even so... what could she do with me? I'm a guy. Make-up can't cover that up, can it?
I felt Kate applying a generous amount of lipstick to my lips. Then, without warning, she started plucking my eyebrows. Ouch!
"Sit still!" She hissed, "it'll take twice as long if you flinch." Once that painful procedure was done, I felt her curling my eyelashes; and she also dabbed something onto my eyelids. The whole thing was surreal - I sat there feeling all manor of things being smothered over my face with no idea what they were or what they looked like. By the end I felt like I was wearing a mask.
"Now, I've had to wash this especially for you and its only had an hour to dry so it might feel a little wet..." Confused, I sat perfectly still as I felt something lowered onto my head. As it pressed down over my hair I felt a wet sensation; and I also felt damp hair running down my back and the sides of my face. I felt hot air from a blow dryer being blown all over the wig; she expertly guided the air to where it was needed until the wig was bone dry. I heard a small thud from the desk before she told me I could open my eyes. I excitedly awaited my reflection as I did so - only to see that she'd turned the mirror face down! "No sneak peeks," she said, "you'll get to see yourself when I'm completely finished." She spun my chair around so I was facing the bed and picked up two fairly large prosthetic breasts. She giggled as she applied some glue to the back of them and thrust them towards me. "Here," she said, "I'll let you choose where these go!"
"But... how will I get them off?" I asked apprehensively. "Oh don't worry, the glue isn't long lasting. And I have this solvent, just in case. Now what did I say about trusting me..." Still nervous, but slightly reassured, I slowly pressed the left breast into my chest. The glue felt cold against my skin, and Kate reached across and held it in place with her hand so I could put the other one on too. I sat like this for 10 minutes, with Kate straddled over me pressing the breasts onto my chest as the glue dried. The only items now left on the bed were clothes; and I was delighted to see amongst them was a silky looking dress that was a bright red colour. Kate first picked up the bra and, knowing I wouldn't be able to put it on myself, she ordered me to stand up so she could attach it from behind.
For a moment everything seemed to go in slow motion. As I looked down at myself I saw a woman's body - slim, completely shaven and wearing nothing but some panties and a bra. With the forms concealed there was no telling that they weren't real breasts - they'd even begun to warm up and feel slightly real!
"OK, time for the main part of the transformation! That dress is brand new; I picked it out especially based on what you... 'like'." I felt myself blushing again as I thought back to the part where I'd told her about my dream of a silky, frilly dress. She smiled at my obvious excitement as I hurriedly held up my arms. Kate approached me and she rolled the dress up slightly before lifting it above my head. I took a deep breath as Kate let go, and felt the garment slide its way down my body. The straps came to an abrupt stop at my shoulders and the skirt danced playfully around my knees.
It was perfect. As Kate tied it up at the back it tightened slightly around my chest, hugging to my body and the fake breasts. I took a step forward and relished the feeling as the dress stroked my legs. I couldn't resist swinging my hips a little - this was even better than I had imagined! I heard Kate lifting the mirror up behind me. The moment of truth. I don't know why, but I was dreading this part. As I turned around I imagined the look of a badly made-up guy in a dress and it made me cringe.
But Kate was right when she told me to trust her. Standing in the reflection of the mirror was a tall, attractive woman. My face looked completely feminine; I was wearing mascara and deep red lipstick as well as having curled eyelashes and slightly blushed-looking cheeks. My newly plucked eyebrows were thin and extremely feminine. My hair was a deep brown and, now dry, it flowed right down to my shoulders where it sat, partially obscuring the straps of my dress. My body looked amazing in the dress - from my large breasts it hugged my slim physique and playfully wrapped around my legs; showing off my smooth, shaven shins. Wow. This was beyond a transformation - it was like a second body!
My girlfriend produced a bottle of wine and poured us both a glass. She handed me one and said, "to your first step of living out your fantasies!" Not quite sure of what this meant, but excited nonetheless, I raised my glass to hers and slowly sipped the wine until it was empty. Kate just watched and smiled, and we sat there in silence enjoying the results of her latest project. After I finished my glass, Kate took my hand.
"You might want to sit down," she advised. As I moved over to the bed I started feeling groggy; my eyes were drooping as I struggled to stay focused on the image of my girlfriend stroking my face and gazing at me with her beautiful brown eyes.
"Wh- what's..."
"Shhhh" she whispered. As I slowly lost consciousness the reality of the situation hit me.
'Must... stay awake. Can't... let anyone see me... like........'
Introduction
Hey all, I'm going to be updating this with some TG captions and stories soon so be sure to check back! I'm a girl who enjoys reading captions and stories of the soft variety and so I thought I would post my own for others to enjoy =)
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