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Throughout high school, she was pretty shy, tall, and slender, with breasts best described as nubbins. Back then, we ran into each other at our first jobs after high school and started spending time together. It was really hard to draw her out and after several months I finally found out why — Jessica was, or I guess is, a transsexual woman. I don't know how she made it through high school hiding it, but she managed. I don't think anyone, except maybe the school nurse and administrators, had any idea. I know she took gym class because the girls would be on one side of the gym or pool and we would be on the other, so I'd seen her in gym clothes and even a bathing suit and I would have never guessed.How I found out was a long story in itself, but to keep this story focused, let's just say we were dating a while when she decided it was time to lose her virginity. I wasn't surprised she was a virgin, she had been really shy in school and I never saw her dating anyone. I was certainly. She sat down and they started talking. His hand was on her knee and he slowing started moving it up higher. Soon he was fingering her pussy, he whispered in her ear that she could touch his cock. She looked down and saw his cock was out and it was 9" and thick. She started jerking his cock and he moved her thong aside and really started finger her hard.She leaned farther down in the chair and she said he then slipped a finger in her tight asshole. He started telling her what a hot slut she was and how he would luv to fuck her ass.. She said she told him that she would luv to ride that cock and started to really jerk his cock. She made him cum all over her hand and then she said she slowly licked her cum covered hand. He loved it. She cleaned up and he gave her the $40 plus another $20. She kissed him and went back to work.The manager saw her and motioned her into his office. He smiled at her as he closed the door telling her that he knew she would luv the job. She said he told her.
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