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Once we started up the road I volunteered to not only take him directly to the store but would also drop him off on our way back to the beach (without telling him exactly where we were going). We all agreed and drove on. Once we got to the store I made a U-turn in the parking lot to let him out. Once I stopped my girlfriend got out so he could get out as well. When she got out I couldn’t help but notice her brother, who was wearing rather short shorts, seemed to have a hard-on. And it was rather large from my advantage, large enough I could swear I saw the head of his dick sticking out of one of his shorts legs. Once he got out and went into the store she got back in the car. As she did she tugged on her own shorts like she had a wedgie then plopped down in her seat. I jokingly said to her: “What’s the matter? Your brother’s big dick stick your pants between your butt cheeks?”She looked at me in surprise and replied, “Oh my God, you saw that?”I told her, “Well, it seems he’s got a. My partner knew I was bisexual, and was into me crossdressing occasionaly when we had sex, so I felt comfortable telling her about my secret fantasy. I explained that there was a fantasy that I'd like to live out, and she was totally fine with it. She knows I'm not going to leave her for anyone, so she feels like she can trust me and doesn't need to control me which I am extremely thankful for. I give her the same trust and freedom. "Go for it!" she said. "I'm away next week and you have the house all to yourself with all my sexy lingerie...". I was relieved that she was understanding and joyful that she was so encouraging. So a few days before she left, I put an ad up on Craigslist. I explained my fantasy in great detail, attached a few discreet pics, and clicked 'post', hoping for the best. I explained that I was an attached bi male, who recently got into crossdressing, and was looking for another young, inexperienced but open minded fit guy to explore our feminine side together. I.
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