I'm a 40-year-old white male who has been with over 100 woman. Now I am obsessed with she-males. In the past year, I've met a couple of she-males. They were both hookers, of course, but I made out with both of them and got a blowjob from one without having to pay. But I didn't get to the part I wanted: giving them the big ram right up the anus. Am I obsessed with anal sex? Or is my problem that I have some dark desire to break my self-imposed "one penis" rule?
"Good God," says Josh, "just pay the nice ladies. It doesn't matter whether you're obsessed with anal sex or multiple penises. You're obsessed with fucking she-males, and they're obsessed with paying the rent."
Both Josh and I were less than impressed by your chiseling ways. "Trying to get free goods from a hooker is not terribly chivalrous," says Josh. "We all go to our different jobs every day, and we all expect to get paid. If you 'really really' want to fuck she-males, and the ones you're meeting are prostitutes, then do the polite thing and make everyone happy."
Your advice for Just Another Silly Girl last week was great, but I think you missed an important factor. She was having sex with a boy who wasn't being particularly nice to her. They can use each other till they get good and sore, but she does need him to stop being an asshole about it. Here's what I'd recommend she say to him: "You like to fuck me, I like to fuck you, too; we have fun, I'd like to continue having fun. But if you ever insult me again, I will tell everyone you know that I'm using you for sex. I like the kicks I get with you, but I'm no longer willing to trade my self-esteem for them."