Cara's First Time

I carried on with my usual routine. I slipped into my 'getting ready' gear. It's all about comfort and femininity while getting ready. I wore a pair of nude shimmer tights, ballet flat shoes, a black bra and a cute comfortable mini-dress. After plucking and shaping my eye-brows I sat down and applied my make-up.

Once the foundation goes on my face I look instantly unrecognisable from my male self. I love that feeling. It's the trigger that tells me that I can release myself completely to becoming female.

I am lucky in one respect with my 'pretty boy' facial features. It does nothing for me in normal life as people, in work and socially, view me as a feminine male but when I dress up the make-up really accentuates the natural feminine features of my face. Although I have never met my mother I am convinced that I look like her but, again, that's a story for another time. Once my make-up was done I changed into my outfit for the evening.

I decided to wear a blue bodycon mini-dress with black opaque tights and black 5" heels. I love the look and feel of opaque tights. I love how they work well with dresses on any occasion and I adore how great they are for just lounging around home; comfy & very sexy! I chose sexy pink leopard Brazilian knickers as I loved the feeling of girls underwear and I felt it important that I was relaxed whilst I had a guest.

My beautiful long blonde wig completed the look. All I had to do now was pour myself a white wine as I waited for my date to come. The buzzer rang and I felt a huge sense of relief to see that the handsome man on the screen of my intercom was the guy from the web profile and not some phoney. Finally, Ben had arrived and the night was about to get a lot hotter.

Ben came to the door of my apartment. He was big, somewhere over 6' tall, with strong shoulders and a friendly, innocent looking face. Normally as a guy, with me being only 5'6", I was naturally intimidated by tall men. Strangely now, wearing 5" heels, I was almost as tall as this guy so did not feel intimidated but I still had to lean up to him to give him a peck on his cheek. That felt so hot!