Cara's First Time

Cara's First Time

This little true story is about the first time I was with a man and a night that I will never forget. My name is Cara. Well that's my girly name, I'm a cross-dresser. I've loved dressing up in women's clothes since I was young when I used to dress up in my showgirl sister's outfits and feel the soft touch of her dresses on my skin. It's just felt right to me all my life and I guess that's the way I'm programmed.

After many years of just dressing in the clothes I eventually began using make-up and wigs to complete the look and to compliment the wonderful feeling of wearing women's clothes. That evolved to putting pictures of my female self online to be shared with and admired by other t-girls and guys around the world, but that's a story for another day. It was through a photo-sharing website that I made many new online friends who shared the love and celebration of femininity that cross-dressing expresses.

One of these lovely people was a guy called Ben. He was 20, good looking and very polite. He stood out from other guys online who sent me typically desperate, dirty messages with the intention of wooing me without any idea about romance and friendship. Ben was sweet and friendly and we often had a laugh chatting online to each other.

Another lovely web friend of mine, Gwen, had often told me about how good it is to be with a man. All my life I'd loved women and t-girls but guys just did nothing for me. I liked girls and I wanted to be one, that's just the way it was. What was there to like about guys?

Gwen convinced me that she had thought the same until she'd been with a guy and she has never looked back. She went on at great length about how nice it was to be treated as the centre of attention by a guy; how they doted on you; how they admired you more than regular girls; how lucky they felt to be with you; how they kissed you more passionately than they would kiss a normal girl and how they made you felt so good when they held you so tightly and lovingly that you couldn't even move as you laid in bed ...