I jerked off almost any time I got free. One day I got tired of the alone action and wanted more fun. I always had a fantasy of being fucked so i decided to try and find someone to break my anal cherry. I wasnt very good with meeting people and trying to meet someone to do that to me was def hard to think of how to do. I turned towards craigslist. I sent out posts for women with strapons, guys... Guys were all fat or gross n no women to reply. I then one day looked in the t4m section. I saw a post for a Beautiful drag queen with an 8x6 cock! I have never been fucked before andonly played with toys. I wasnt sure i would be able to take it and didnt want hurt.. But she looked good dressed up and the cock was so big and sexy and shaved completely smooth making it hotter!I sent an email and pic to the post in hopes she liked what she saw n picked me. I was a skinny 145lb 5'10" white boy. She replied with a phone number and we got to texting. It was the middle of the day n she was ready.. Worse still, he dumped her for the town slut, Barbara Ekins, and to add icing to the cake, when Louise tried to ask him why, he told her he’d been cheating on her with Barbara for months, and Barbara was a better fuck anyway. Louise was devastated, and for a week, she cried all the time and wouldn’t eat, just lying in her room, like a hermit, while I sat and wished I could help her get over him. My parents seemed to think it was just something she was going through, and she’d snap out of it soon enough, so they weren’t much help. As for me, well, I was just an 18-year old kid who’d never had a girlfriend. What did I know about relationship advice? She came home from work one afternoon, and went straight to her room. I heard her softly sobbing in there, so I went to the door, determined to help. She was lying on her back, with her head turned, facing away from me, and I tried to think of something to say that would help, but nothing came. I tried my best…. “Fuck Derek!” I.
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