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It was strange seeing such a nice, meaty man-sized cock on a boyish young man, yet quite sexy.I stood up and bent over as I rubbed lube up in my ass and along his shaft."How do you want to take me?", I asked."Just lean over the seat in front of you.", he said with a quivering voice.I sensed that this was a new experience for him. "Is this your first time taking a crossdresser?" It's my first time taking anything other than my hand." he said in a shy voice."Well, take your time and enjoy the plunge." I whispered to him, as I gently sucked his earlobe. It was hard to believe that he was a virgin, but then again, there's always a first time for everything for everyone.I rubbed my ass cheeks to make them shiny, then I leaned against the seats in front of our row. As I felt the tip of his prong touch my rosebud, I pushed back a little to help him enter me. After a minute or two adjusting to the sensation of his cock inside my ass, I took him further into me. For a young guy, he had a. "Cool dude. I'll catch up with you guys later. Gotta go meet my agent over some deals." He said. He gave Rachel a kiss and headed out the door. Dinner went by and Jamie and Rachel were talking about school and life. Jamie was a shy kid who had wanted to talk to girls but he could not get the nerve nor the confidence to do so. "Rachel, is there something wrong with me?" He asked her with deep concern. "No sweetie, what would make you think that?" She asked him back. "It's because I always get picked on by the jocks and girls always reject me. Truth is I want to find a girl and I do know one but I don't think that she would want me as a boyfriend. She is a great girl and I am scared that if I asked her that I would get laughed at again." Jamie had always asked girls out but he would either get turned down politely or very rudely. Rachel saw this opportunity to help her cousin out. Since she had the whole summer she had all the time she needed. "Jamie, I am your cousin and I love you.
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