IV: James' Crossdressing Fantasies

Chapter 4: The Talk

"You might wanna take off those heels of yours, they really start to kill after a while. Make yourself comfortable, I'm just going to use the bathroom quickly." Kate left the suitcase by the door and expertly tossed off her heels before disappearing into a little en-suite room to the left.

I leaned against the wall to steady myself as I tried to prize off my heels. Ouch, they were on tight! The back of my foot rubbed up against the shoe as I yanked at it, and as it came off I noticed my heel looked quite grazed from its ordeal. I repeated the process with my right foot and, now that they were off, I appreciated what Kate had meant. It was good to be on level ground again, and my feet relished not being squeezed into those deathtraps anymore! I walked towards the bed to examine the hotel room further.

Opposite the en-suite was a small table, and next to it was a large, ornate wardrobe. In the center of the room was a large double bed, with a beautiful cream duvet covered in beads and ribbons. The pillows were of a similar design but were a pale pink colour - this was definitely a girl's room! There were two bedside tables on either side of the bed, and as I approached it I noticed there was also a cabinet in the corner of the room next to the wardrobe, on top of which was a large mirror. I watched my reflection dance closer as I moved towards it; my hair was bouncing around my shoulders and the dress was swishing about my knees in unison with my movements - what a delightful feeling! The material was silky soft and really made me feel feminine - I could walk around like this all day!

I came right up close to the mirror and peered into my made-up face, expecting the illusion to shatter at any moment. Even from this distance I could only just tell it was me - and even then I still looked completely convincing as a girl! I could hardly contain my delight and did a celebratory twirl, revelling in the moment. Forgetting where I was I started to rack my brains for other things I could make my reflection do. I grabbed the sides of my dress and swung my hips, watching as the material wrapped itself around my legs, first to the left, then to the right. Then I backed up towards the bed and flumped down. Hm, that wasn't right. I'd sat on part of the dress. I stood up slightly and ran my hands under myself, smoothing out the skirt as I had often seen Kate do at home. It was like an out of body experience as I watched the girl in the mirror do the same, and afterward she sat there patiently awaiting my next move. Here I was "watching" this beautiful woman and I could make her do whatever I wanted!

I started to pose a bit in front of the mirror - I pouted slightly and then threw my hair back, leaning back slightly on the bed. I lifted my chest to accentute my breasts and held the pose, watching my chest rise and fall as I breathed. Mesmerised, I sat upright again. I crossed my legs in a feminine way and then started to play with my hair like I'd seen other girls do. I twisted it around in my hands and smiled at the mirror, biting my lip as I did so. As I started to flutter my eyelashes I noticed an amused Kate standing behind me in the reflection.

"My, my! You're really starting to get into this!" Kate stood leaning on the bathroom door, obviously enjoying watching my antics. Ashamed, I quickly uncrossed my legs and put my hands in my lap. How long had she been there? I felt my face flush with shame at the thought of me pouting at the mirror like a little girl.

"Relax, it's okay. I want you to get in touch with your feminine side - that's what this trip's all about!"

She smiled and lifted up the suitcase before making her way over to the bed. She threw it down by the near bedside table and crawled across the duvet to sit beside me.

"Now, I think it's time we talked."

I quietly nodded as Kate took a deep breath and began.

"So first I guess I should come clean. When you first told me your secret my first reaction was of shock. I didn't like the idea of my guy prancing around in feminine clothes. I thought at the time if I didn't say anything that maybe it would go away. I was scared about our relationship, about you, and about what would happen if I confronted you. Does that make sense?"

Again, all I did was nod and let her continue.

"Well, after a few days I could see that you were still the same guy. You were still the James that I knew and loved, and that made me realise that you had probably always had these desires since we first met. It kinda helped put me at ease because I realised that you weren't... changing. You'd made it quite clear that you weren't gay, and that you were happy being a man. But that said, you clearly enjoy being a girl too, right? I saw the way you were prancing around in the mirror... you looked so at home being Emily."

"I-I know... I can't explain it. Being in these clothes just makes me feel so... feminine. I love the way these clothes feel on me but I love even more how it makes me feel about myself. You made me look so pretty and I... wasn't expecting that."

Kate smiled. She reached into her bag and produced a debit card. She handed it to me and watched intently as I examined it. Oh god! The card was in the name of Emily Barton... was this for me?!

"Kate... what is this?"

"It's a debit card, silly. It's set up under your new name - you're a 19 year-old called Emily now!"

"But... I'm not Emily! I mean, I like being her but..."

I felt my eyes welling up as I realised that right now I had no way out of this outfit. Was this the way it was? Was Kate going to make me start a new life as Emily?

"Oh no, don't cry! You're still James. I know this is overwhelming but... this way you can have both." She squeezed my leg reassuringly. "We'll spend this weekend taking Emily for a spin. I don't want to spoil too much but we'll go out and do a load of girly things together. We'll buy you some outfits, get our nails done... all those things that real girly girls do. After that, we'll go home, and once we're there its up to you where you want to take this. You'll have access to both sets of clothes, the breastforms, everything. You can keep on going to work and living your life as James but whenever you feel like escaping and being Emily for a while, that's fine too!"

I was gobsmacked.

"Wow... how're you being so understanding about this?"

"Oh come on, it's the least I can do! You've always kinda... been there for me, y'know? Whenever I've been worried about something you've always been there to put my mind at rest. Now I finally have the chance to help you with something in return... so I decided if this is your thing, I'm going to make the best of it. Besides, I think it's kinda neat that my boyfriend doubles as a girlfriend who I can take shopping and have girly nights in with! I don't think there are a lot of girls who can say that!"

"I.. I don't even know what to say..."

Kate smiled and stood up. "Well, how about you don't say anything for now. You've got £500 on that card to spend and we've got a whole afternoon to shop! We need to get Emily a whole new wardrobe - cute tops, skirts, dresses... not to mention underwear. The whole nine yards - up for it?"

And so this was it. Kate had plunged me into this female world and had made it quite clear she was happy for me to enjoy it to the full. Bringing out my feminine side even seemed to be making her happy! In spite of this, though, I was hesitant. It wasn't long since I was desperate to get into the privacy of our hotel room - was I really contemplating going outside again?

As I stood up, though, my mind was made up for me. I once again relished the feeling of the dress about my legs and my head was invaded with all kinds of feminine thoughts. What would it feel like to wear tights? Would I look good in a skirt? My god, if one dress made me feel so good about myself I couldn't wait to have a wardrobe full of clothes! The excitement of diving into a world of wonderful women's clothes was too much to pass up.

"Okay! I'll do it!"

Kate smiled and kissed me passionately on the lips. She made her way around the bed to the suitcase and unzipped it. After rummaging around inside I was relieved to see her produce some flat woman's sandals.

"We can't have you breaking your ankles on those things if we're going to be trekking around the shops all day!"

I slipped into the sandals and Kate put her heels back on and stood by the door.

"I'm so glad we're doing this. We're going to get you some beautiful oufits, Emily! I already have a few ideas... this is so exciting!"

She swung open the door and I felt myself physically shaking at the prospect of going back outside; but now it wasn't just nerves. I was about to go and buy all the clothes I'd ever dreamed of and I couldn't wait.