Dear Uncle Steve: Relationship Advice from Steve Lewis & a Girl

Dear Uncle Steve: I’ve always thought of myself as a good person with strong morals … until I started having an affair with a married man whom I met while babysitting his children. I watch his kids 2-3 times a week while his wife is at work or wrapped up in social engagements. He’ll stop by and we’ll usually bang one out in their guest room while the kids are playing or watching movies. I know it’s wrong, but I’m addicted to the thrill of getting caught. Can I realistically keep this up?

Scandalously, Naughty Caretaker

Dear Naughty Caretaker: A Chinese fortune cookie fortune once wisely observed, “He who seeks advice merely seeks an accomplice.”

The guy sitting on my shoulder in the little red suit and pitchfork says, “Rah rah rah, sis boom bah!” But … that little guy with the wings on my other shoulder is sayin’ something else. He says that you’re a disgusting, immoral slut and to bang a married man while being entrusted with the care of his children (who are watching TV in the other room) insures that you’re going to hell in a hand basket. Or you’ll be plagued with bad sex for the rest of your life. Sweetness, what you’re doing is despicable and you should seek help for your addiction just like a junkie crackwhore.

xoxo, Uncle Steve

Advice from a girl: Does this chivalrous gentleman plan on leaving his wife anytime soon? The answer is … probably not. Even thought it “takes two to tango” (ask Tiger Woods), you’re undoubtedly going to be portrayed as the homewrecking slut if anyone ever finds out about this. Like a cruel high school rumor, this will become that one thing immediately associated with your name. Let’s put karma aside and worry about your reputation. “Babysitter having an affair with the father of the children she babysits” is pure character assassination. Drop Dad of the Year like a bad habit and give the family your resignation due to “schedule conflicts.”

Dear Uncle Steve: I have a problem most men would envy: I have a much larger-than-average penis. So large, in fact, that it’s difficult for me to have sex. Almost every girl I’ve ever been with has stopped midway through a sexual act because she was in pain. How can I cope with this dysfunctional curse of mine?

Tortuously, Big Boy

Dear Big Boy: Finally, someone I can relate to. Someone famous (it may have been Teddy Roosevelt, but maybe not) once said, “It’s not the size of the unit but how you use it.” This works both ways (actually more than just two ways, but that’s another conversation). Big Boy, you must learn to use your gift with patience and diligence. I feel like Yoda instructing Luke Skywalker. The force boy, the force. Take it easy, work with your partner, ease into her, and you’ll both find happiness. I guess a Boogie Nights quote is also appropriate here. Jack Horner tells Dirk Diggler (a man with a similar “problem”), “Don’t just ram it in there like that — this is not a hole in the wall pal. It’s Rollergirl.” Rollergirl later compliments Dirk’s technique, “He can fuck really hard or he can fuck really gently. He’s the best”. Watch the movie for technique, and buy lots of good lube for practice.

Advice from a girl: I highly doubt that you’re unsure how to properly operate your “much larger-than-average penis,” unless, of course, you’ve been abstaining from sex because of an uncomfortable past experience. Let bygones be bygones and show your next partner how fortunate she is to be dealing with a man of your caliber. Take it slow, and focus on her. Stop and regroup if it moves from pleasure to pain. With some time and practice, let’s hope that you’ll be rolling in pleasure.

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