First time I wore girls clothes

When I was ten years old I had a operation on my penis to widen the tube because it was slowly closing and giving me an infection, The doctor cot off the foreskin and widened the tube and sent me home. My Mother thought it was best that I sleep in her bed with her so she could monitor my health and insert the thermometer to keep it widened, she had me wear one of her flimsy night gowns that she wore.

This went on for 4 weeks and I grew to like so I asked If I could dress like a girl she told me yes as long as it was only when I was at home,My mother was a prostitute as was my Grandma and Aunts. We lived in a 1800's former mansion so seeing women in various forms of undressing or completely nude was normal. I got turned on watching my Mom but nothing happened life went on until I was in Jr High.

My best friend George lived in town across the street from school and I'd wait at his house until someone picked me up. One day George asked me if I wanted to see some of his Parents private pictures, so of course I answered yes, they were pictures of his Mom dressed up as a Dominatrix and his Late Father dressed up as a Maid. I was highly eroused and started to relate to George the story of dressing up like a girl we went up to his bedroom ,stripped and started making out when our Mothers walked in and they both said isn't that cute they are both sissies. On Saturday night George and his Mom came to our place , My Mother called me down stairs and when I walked in the parlor I saw George and several other boys dressed in pink dresses along with their Mothers.

When I asked what the hell was going on I was informed it was time to train the little sissies, in the center of the room was a box with a lock on it,We were told to kiss each other so we did with comments by our Moms, then we lifted up our dresses and half of us were told to give blow jobs like good little sissies,it was so much fun I wanted to suck all the cocks,then the box was opened and dildo's were brought out, the ladies put them on and told us to bend over like the sluts we were, I was the first and they fucked me one at a time untill it was the next boys turn this went on for 7 hours. This happened during the hippy era of the late 60's.