Chapter 81

• I was always a smaller than normal boy growing up. I got picked on being called pee wee, and girly boy. And I really wondered since I was young if I would have been better off born a girl. I had a few sexual moments with boys in the past. One time was a attempt at anal sex. But neither of us could get big enough and/or hard enough to have penetration. But just the feeling of a boy climbing onto my back and trying to mount me, with his penis trying to find and penetrate my anus was extremely sexually arousing. It was a single memory that burned deeply into my young and developing brain. Even though I was very attracted to women, I also couldn't stop the curiosity of being a woman. I had turned eighteen a few months earlier, living in a small town in New Hampshire. It was the week of thanksgiving and my parents where going to Massachusetts to visit family. My older sister was planing on having a party at the house, while our parents where gone. I didn't want to be around her and her friends. I talked to my best friend Ricky who was also leaving town with his girlfriend. He told me that I could stay at his house for the week. His dad (Big Mike)was a over the road truck driver and was also leaving out for work. My parents didn't like me hanging out with Ricky. A lot of people didn't like his dad big Mike. He was a old biker guy, who was always up to trouble in his younger days. So for years I always lied about hanging out with Ricky. But we got along so good. And big Mike always treated me good, when he was around.
• I was excited about just being alone for the week. I took some extra days off just to not do anything, after all I had just graduated high school too. Ricky gave me the key to his house on Monday morning and said his dad was leaving out Tuesday morning. So Wednesday morning I headed over to Ricky's with bags of food and a little weed to smoke. I walk down the long driveway looking for big Mike's truck, just in case he hadn't rolled out yet. He was gone, I unlocked the door and walked in. It was the cleanest I've seen in years. I found a note Ricky left saying he had cleaned up for me. I thought it was funny he cleaned the house. Since big Mikes divorce, and Ricky's mom and sister moving out years ago it was pretty messy since. I got comfortable and just watched tv and smoking a little pot.
• I end up passing out on the couch. I wake up early Thursday (thanksgiving) morning. I smoke some more, and I wonder around the house. I remember that big Mike had a little stash of porn in his bedroom. Flipping through I find a video of a thin guy wearing girls clothes and a buff guy with a big cock on the cover. I bring it back to the living room and pop it into the vhs playing. The buff guys fucks the shit out of the guy dressed up as a girl. I was feeling horny, that's when my curiosity ran wild. I wondered what it would take for me to really be a girl. These day's with the internet to learn from, and the fact that one's sexual preference is more accepted. But in 1990 things where very different, there was no way to really research and learn about anything considered a taboo lifestyle.