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I got lucky,kinda lucky anyway during my junior year.By that time I had moved off campus and had my own apartment, ah yessweet privacy! I also had a steady girlfriend who was a psychologymajor and remarkably insightful. I did not tell her about mycrossdressing and while at this point in life I can see that that waswrong on my part back then I was seriously scared about being forthrightabout it. One night she and I were hanging out in my apartment andclear out of the blue she told me that I had beautiful eyes and that shewanted to see how beautiful they could be with makeup. I had a reallyhard time trying to appear reluctant for I was anything but reluctantbut pretended to cave and let her go for it.I was amazed. I had tried makeup myself but had no idea what I was doingso the results were less than spectacular; this time with her knowledgeand skill the results were spectacular. I had really beautiful andmoreover feminine looking eyes when she was done with me. She let mesee. “And let’s make this really interesting. If the Badgers win — which they will — we come back here in a week, next Saturday that is, with you dressed in drag. I get to pick your outfit.”His eyes darted back and forth. I could tell he was trying to weigh how his friends and acquaintances here would react to that, as opposed to the ignominy of backing down from my proposal. Then an evil glint flashed in his eyes and he grinned.“Accepted,” he said. “But only if you agree to my terms. If Kentucky wins, then you blow me, here tonight, in front of all these people.”I clenched my teeth to keep my jaw from dropping or from saying something stupid like “you’re kidding.” Of course he was serious. I had offered to humiliate him, he now simply replied in kind. I took a sip of my mojito to disguise my discomfort, but I couldn’t back down, having been the one to first propose raising the stakes to this level. Besides, I had every reason to expect to win the bet. Still, my voice cracked a bit when I.
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