My best bud Charles and I were hanging out at his rich parent’s mansion, joking around after consuming several beers, about all the loser chicks in our class and how they’d never get laid. It was in the middle of this conversation that he dared me to hook up with one of these losers but I told him it was childish and too much work. He then upped the ante and told me that if I had sex with one such loser chick, Amy, by my sixteenth birthday, which was only two weeks away, then he’d buy me the best seats at the next UFC event. Since I had nothing to lose, I agreed and the more I thought about it, the easier it seemed to me. I was a tall and handsome guy who was popular in school, without even being a jock. I was also considerably experienced with girls, having had several girlfriends and gaining a decent reputation for being good in bed, which all put me at an advantage. The class was finally over and it was time to carry out my plan. I followed her to her locker and watched as my pal,. ”“I like to think so,” said Regina. “Funny, the normal response is an uncomfortable look while slowly backing away.”Jackson giggled. “Being a trans, it's hard for me to get surprised by different lifestyles.”“Trans?” Regina lifted a brow, and stared at Jackson for a long moment before saying, “You're kidding. I can't tell one bit.”“I owe it to my parents, I guess,” Jackson said.“Any surgeries?”“Aside from my boobs I'm all natural.”“You are very lovely,” Regina said. Jackson smiled, fidgeting in her seat. “So, Vanessa's your ex and your would-be date was a boy. So, bisexual?”“It's easier to just call me queer, really.”“Fascinating,” Regina said. “So...you've kept your...equipment?”“I have,” Jackson replied. “I'm quite fond of it.”Jackson and Regina shared a laugh. Then Regina said, “I won't lie to you, Miss Jackson, you make me...curious.”Jackson had a feeling what Regina meant. “Really?”“Mhm. I assume you're an open-minded woman?”“Yep.”“Excellent,” Regina said, then leaned closer. “I.
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