My Tranny Life

I knew I was different from the boy I was born to be from a very young age. I was raised by two Aunts, who were very loving but it was a feminine environment. When I was nine I would raid their undie drawer and masturbate (although, then it was just a sensation) my stiff penis.
At twelve I was hooked on silky undies, they made me feel feminine and I became a crossdresser. I grew my hair long (it was the fashion) and I felt more feminine and also my voice hadn't broken (which created bullying from classmates). One such bullying occurrence was to change my life.
A master at our school witnessed what happened that day and called me to his room after school. I was upset and he was very affectionate and tried to console me. He gave me a cuddle, I liked it, then I felt his hand go inside my shorts, I gasped and tried to pull away but he had me firmly in his grip and I knew he could feel the nylon knickers I was wearing.
Soon my shorts were off and he had my penis in his mouth and he drew me to my first ejaculation.
I loved that experience, he knew just what to do and I felt the girl I was always meant to be.
At fifteen I confessed to my Aunts, they were loving and helpful. I became more feminine looking over time, but never wanted to transition fully, although I grew a pair of lovely breasts with the aid of medication and exercise. By my late teens I was going out in public dressed as a female and was really quite lovely. I formed friendships with like minded friends, but never had a "boyfriend", until one day I met Graham.
I was twenty, I was in a pub one summer day, I had nearly finished my G&T when he appeared and asked if he could buy me another. He was nice looking, fit and I guessed around fifty years old or so. I was intrigued as I watched him go to the bar and buy the refills.
When he came back he sat next to me, he smelled of aftershave, nice. We chatted for some time and I learned that he had lost his wife some two years previously and was looking for company. Well, he was so friendly and kind that I confessed to him that I was a transvestite and thought he might be disappointed, but he said "perfect" he missed his wife and was not really looking to start a relationship with another woman but just to have friendship and sex.
We ended up that day at his house and in his bed. He made me feel so girly and I know I was able to please him. I loved his big penis and hairy body. Graham loved the undies I was wearing and adored my breasts, was amazed at the size of my penis and was a great kisser.
I also found out that day he was fifty-six had no family and was an executive with a large multinational company. We began an intense relationship that day. I found just what he liked and made sure I provided him with the ultimate pleasure.

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  • You naughty girl, I'd love to hear more.
    Signed Lingerie Lover

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