Life Lesson #2: Freaky People Attract Other Freaky People :)

So for the most part, having sex while crossdressing is a bit of a fetish and once people know you are into it they are now free to share their own fetishes with you. That’s were my next life lesson comes in and I have a couple of stories about people doing some surprising shit near me or to me.

Around 26 years old, I was now going by the name Amanda and I met another crossdresser named Missy who I liked to hang out with and dress. Missy and I generally hung around either at her house or mine. Usually we dressed up casually, did our makeup, and just watched TV or played video games, no big show of it. On two occasions we hooked up and this is about one of those times.

We were at Missy’s house and it was past midnight. Missy lived in the basement of her parents house; but entry to the basement was separated from the main house so the only ways in or out were through a door to the outside and through a door connected to a garage. The garage door was always locked and Missy’s parents never came into the basement at all. After all, Missy was paying rent and this was her place. We had been drinking rum, smoking weed, and playing PlayStation for most of the evening and were winding down. I always brought an overnight bag full of my makeup and some clothes even though I normally didn’t stay the night. Missy would tease me about my bag a lot because I always had lube and some sort of toy in it - a dildo, a butt plug, whatever. Missy started going through my overnight bag and teasing me about what she would find and lo and behold, she stumbled across a glittery purple, 10 inch double headed jelly dildo! It was new in the package and I had sheepishly purchased it a day ago from a sex shop downtown and then quickly stuffed it in my bag to make my getaway. Missy was histerical about it and was not going to let me live this down. She opened it up and waved it around in the air laughing her ass off. Then she suddenly got a grin on her face, and said “Wanna try it!”

In no time Missy and I were on the floor.