Jimmy Becomes Jenny
 

I was 18 the summer I graduated from high school. We lived at the beach, a couple rows back, and mom worked long hours. I was hoping to get a girl friend soon - something I had never really had. I was short and had feminine features - something that pleased my mom, as she always wanted a girl. I had been bullied and called names for years, but I was starting to work out now, determined to put my past behind me.
I was walking along the beach one day, taking pictures when I came across a older man. He also had a camera, so we began to talk. We seemed to have many common interest and he was so easy to talk to. We talked about lots of things and I found myself really opening up about my personal life and insecurities. Hours flew by... he made sandwiches for lunch while I sat on the deck. When the sun was getting low in the sky, I got up to leave - it had been a very nice day and I told him so. He called me to him and told me I needed to shave... your legs I mean, and your underarms. There was no sign of a smirk, only a warm smile. He told me I was pretty... that it was ok for a boy to be pretty, and I should never deny who or what I was.
I was lost in my thoughts walking home. I would have loved to spend the night there on his deck - just porno chatting. I could tell him things that no one knew, and he really listened, and seemed to understand me - something that I struggled with myself. I thought about shaving but decided it was silly.
Mom left early the next day. I had planned to look for a summer job but the longer I thought about it, the more I wanted to see my new friend. I took a long hot bath and masturbated, hoping that would help, but it didn't. Almost before I realized what I was doing, I had grabbed my razor and started shaving my legs. I didn't really want to, but I had been told to do it, and I kinda liked that. First time for everything I thought as I shaved my underarms. My stomach had butterflies as I picked out a pair of pink shorts. Don't deny who or what you are he had said so I wasn't feeling guilty about my feminine side today. I drove the two miles to his house not wanting to get hot and smelly by walking.
When I knocked on the door, there was no response... maybe it was crazy anyhow. I was heading back to my car when he called from the upstairs window asking me to come around to the deck. When I got there, he studied my legs and smiled, running his hand up between my thighs to make sure I did a good job. I raised my arms to proudly show my freshly shaved underarms, and he was all smiles. He said that he had always had a desire to fuck a boy, and that my looks had inflamed that desire. He called me to him, slipped my shorts and undies down and pulled my shirt off. I was standing naked before a man that I had only known for 24 hours and I was so turned on.
He turned me around and had me bend over and spread my cheeks. He slipped a moist finger into my ass causing uncontrollable spasms in my rectum. He pumped me like that till I loosened up to his satisfaction. He told me where the ky was, and swatted my ass to get me moving.
When I returned, he was naked and semi hard. He sat me next to him on the yoga mat and pushed my mouth to his cock. I had never touched another cock, so I just did the best I could. It was seemingly good enough as he was soon moaning. He was pushing my head down, going deeper and deeper until I choked. I felt so guilty as he was very near to having an orgasm, but he didn't seem to mind. Now, he had me on my hands and knees and facing away from him. I felt the cold jelly as he worked his fingers in and out - first one finger, then two. After a pause, I felt the head of his fat cock against my asshole. He grabbed my hair with both hands and yanked me back all at once. I had been expecting him to fuck me but this sudden penetration had me screaming with pain and surprise. He held me tight and thrust again and again, deep inside my body. Although the pain was intense, it was also short lived, and before long, I was on my hands and knees again and he was taking long deep strokes into my ass. I grunted each time he bottomed out, which seemed to please him. Before long he held my hips and pushed hard inside me. He was cumming and I was so proud of myself.
When he released me, I collapsed - wondering how long it would be before I could use the toilet again. We lay there for a couple hours. He had called me a cunt and a pussy boy several times while he was fucking me, and wanted to assure me that it was not an insult. I thought to myself just how much I liked being his pussy boy, but I just smiled and said "Yes sir." Before long he pushed my mouth down on his soft cock and told me to practice. He lay back and started texting his friends while I slurped and licked. Feeling a little life returning to his flaccid cock, I wondered if he would fuck me again.
No more issues with my girly looks. He wants me in pigtails as soon as I can, and he's going to take me shopping for lace panties. Life is so good.