How stupid would it be to sleep with my boss’s gorgeous 18-year-old son? My boss has become a mentor to me. He and his wife have welcomed me into their home, which includes their aforementioned son, a high-school senior. I am a 23-year-old woman. Normally, I wouldn’t sleep with anyone younger than 20. But besides being very attractive, my boss’s son is funny, kind and sweet. He’s also incredibly horny and has some serious unexplored kinks that most girls his age have no interest in. I want to spend the next few months fucking my boss’s son—bearing in mind and honoring, of course, your campsite rule. Here are the two problems as I see them: (1) Fucking around with your boss’s kid seems a surefire way to seriously wreck your relationship with your boss. (2) He is still in high school.
—Sex Or Not
1. Fucking your boss’s kid seems like a surefire way to get your ass fired, SON, and depending on what field you’re in—and how important good recommendations and work histories are in your field—fucking the boss’s son could seriously derail your career. If, you know, you manage to get caught. But if you do decide to fuck the shit out of a gorgeous, funny, sweet and kinky adult who happens to be your boss’s son, well, you wouldn’t be the first person in human history to risk everything for sex. As Mark Twain observed more than a century ago: “The human being, like the immortals, naturally places sexual intercourse far and away above all other joys—yet he has left it out of his heaven! The very thought of it excites him; opportunity sets him wild; in this state, he will risk life, reputation, everything—even his queer heaven itself—to make good that opportunity and ride it to the overwhelming climax.”
2. He is an adult—who is still in high school. You are not that far out of high school. Math is hard for me, SON, but according to my calculations, you’re not that far apart in age. You might be sabotaging your career, but you wouldn’t be robbing the cradle.
3. The campsite rule for new readers: The older and/or more experienced person in a sexual relationship with a large age and/or experience gap is obligated to leave their younger and/or less experienced partner in better shape than when they found them. That means no sexually transmitted infections, no fertilized eggs, no unnecessary drama and no unnecessary trauma.
Say you’ve always wanted to peg a guy, but your otherwise GGG hot husband isn’t into receiving anal—for good reason (he’s had health problems back there)—but he jokingly suggests he would be fine with you pegging his equally hot gay little brother. Should you ask his gay little brother if you can peg him?
—Wanting It For Evah
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