I come from a broken home. My parents
divorced when I was just five years old. My older brother and I stayed
in the family home with our mother. Father moved in with a new woman
and although we saw him once a month it was never enough.
Mother moved a new bloke into the house just a couple of months later. Eventually he became our stepfather. He was just 21 years old when he stepped in, fresh out of the army and clueless how to raise two young boys. Things changed dramatically at home. Being ex-military he was strict beyond normal and it wasn't long before he ruled the house and our lives with military precision. Not long after their marriage he began to enforce his rules with a leather belt. Progressing eventually to using his fists on us kids. I began to develop behavioral problems and rebelled.
As I grew up I was sent off to a naughty boys boarding school. It was easier to get rid of me than have me disrupting life in the home. I left school with no qualifications, no goals and no future plan. I was 16 years old and alone in the world with no direction or guidance from my parents.
Needless to say, I started hanging out with the wrong crowd, committing petty crime and experimenting with drugs. I drifted through life, drugs and crime until at the age of 21 I met my first real girlfriend. I was inexperienced at sex until I met her. I thought I knew about sex but I was very wrong. She was insatiable and would always bring something new into the bedroom. One night she asked me to put her lingerie on. I felt a bit stupid at the time but I went along with it anyway. She dressed me up in hold up stockings knickers, heels, and a tight little black dress. It was all finished off with false nails and makeup. I remember being turned on by the feel of the stockings against my skin as she ran her hands over my legs. She asked me to do some poses for her and she photographed me. I could see myself in the mirror and I'd never felt so sexy before. It was the most intense erotic thing I'd ever done and I absolutely loved the feeling it gave me. Over the next couple of years we would dress up together often and I was always keen to try on different outfits. It became our thing and we explored it to the max.
As happens in life's twists and turns, we parted ways several years later. By then, however, the dressing up had gotten under my skin and became a big part of who I am. I am just a normal guy and I'm happy being a man. I work hard and wolf whistle at the women going by below the scaffolding as we work and I enjoy my nights out with the lads. I do not wish to change myself with surgery or hormone replacement therapy as I am comfortable in my own skin. I do however get to dress up whenever I like and feel sexy in my stilettos, pretty clothes and make up. I couldn't imagine my life being any other way now. I thank God every day for the time I spent with that special woman, the things she taught me about myself, and the gift of crossdressing she gave me all those years ago.
Feel free to follow Deana at https://www.facebook.com/deana.williams.79656
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