A Cross Dressing Short Story

A Cross Dressing Short Story

1It was in 1969 that I first revealed my secret to another woman…. I felt I just had to. I had invited my boss’s secretary for a drink and I felt she would understand. I slipped her a couple of photo’s of myself dressed as Christine. Yes, she understood alright, although she said she would never have suspected such a thing of me! The next week she visited me at my home. This became a regular event when we would sit and sip sherry in a ladylike fashion. Soon I was showing her my large range of lingerie.

One day she asked to feel the material of certain undies I was wearing. I stepped over to the armchair in which she was sitting, and her hand felt the nylon slip and then ran up and down my sheer black stockings until she touched the crotch of my panties. I gasped as it had a sensational effect on me. “Nice?” she asked, as her fingers began to move slowly up and down, brushing the nylon against my now stiffening penis. Of course, she went on until I exploded in a wonderful orgasm, and that was the beginning of a relationship which lasted some years. Every time she visited, or I visited her flat, it ended up with her giving me a lovely orgasm. Sometimes she would be at me almost before the downing of our first sherry or whatever we may be drinking. I hardly had time to strip down to my nice undies before her fingers would close around and work on me until I was trembling at the knees.

As I backed off and collapsed in an armchair breathing heavily, I still wanted more. On days when she  was feeling rather sexy herself, she would disappear to my bedroom and strip off, she would borrow my black sheer negligee and re-appear beside me and we both pleasured each other.

One day she asked if I wanted to meet a woman friend of hers called Bea, Bea liked to watch other please each other and she also had a friend called Mary who liked to apply make to cross dressers.

The four of us meeting together for the first time was mind blowing and this happened once a month.

My wife knew all about what went on and was happy to turn a blind eye, our children had flown the next and she was happy to go to work each day, we lead a normal life really. I now have a wild circle of female friends and still like to flaunt myself in front of them.

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