I wanted her asshole. I positioned my hand on her ass crack, and slowly pushed my finger inwards towards her asshole. She stopped me at this point, pe...haps unsure of my purpose, or simply uncomfortable with the process. I suggested we go up to the bedroom and she agreed. I opened the door of the bedroom and allowed Natalie to enter ahead of me as usual. I watched her ass walk away from me like so many other times before, but this time I followed and stood behind her, putting my hands around. I had met Cesar at mom's company picnic in Griffith Park a few weeks ago.Cesar had wanted nothing to do with a skinny little kid like me then.He'd mumbled a few words and shambled off to join a pick up basketballgame with some of my toughest classmates. My mom had given me a look,like I should follow, but I had just rolled my eyes. When I looked up from my book I had them pointing in my direction andlaughing. I'm the smallest boy in the junior class at Fairfax High, only5'5", and just over a. ."I smiled and said, "Don't over think it. Life is too short."She was silent as we dried off and dried and brushed our hair. Her only comment was, "I can't believe you're only fourteen!"When I was ready I turned to her and waited to see if she was going to put her clothes back on. She put her brush down and we looked into each other's eyes for a long moment. Finally I smiled and took her hand. I said, "I think you're ready for this. You have nothing to lose. And if I'm wrong, if you can't. ....." I was shocked I looked at him standing there his long smooth shiny hairless legs in a big set of heels, wearing a tight lacy black dress that I’d fantasies about his sister in numerous times. His blonde hair straightened past his shoulders and his face fully made up with red lipstick and long eyelashes. I couldn't believe my eyes and finally managed to utter the words "what are you doing" he slowly shifted his body weight onto his other leg and said "you said I looked like a girl, so I.
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