John M. from St. Paul, Minnesota asks, “Dear Poppy, I’m 48, divorced and I’d like to think that that I’m fairly experienced when it comes to sex. A few months ago I started dating a new woman who likes to stick her finger up my butt. I keep telling her I’m not into that, but she keeps saying that I need to relax. What should I do?”
Dear John, while I realize that “assplay” is all the rage with the cool kids, I think some things are better left mysterious…with your turd crib being at the top of that list.
So, I think you’ve got two options:
Option #1: Prior to any foreplay, have an honest and sincere conversation, where you clearly explain that your posterior is off-limits. Then, after she stops laughing at you, inform her that perhaps the two of you should take a break.
Option #2: Surprise her by having a “butt truffle” waiting in the chute. The moment she plucks a cherry from your ass, her prospecting days will be over.
Please write me back, I’m dying to know how this turns out!
Tito H. from Orange County, CA writes: “Yo Answerman, I’ve been dating the same bitch for three weeks. I know she got me an X-Box for Christmas, which I fucking want, but I don’t want to buy her shit, ’cause I’m gonna dump her ass. What should I do?”
Dear Tito, the mature move would be to break up and let her return the X-Box. Then she will be free to find her soul mate, a parolee, who breeds hamsters in a broken down Chrysler Mini-van.
But, if you decide to part ways once you get the X-Box, I have written a riddle just for you:
Question: What’s the difference between you and my asshole?
Answer: One is a putrid, shit soaked hole that should never be kissed and the other lies between my ass cheeks.
Ken T. from San Pedro, California writes, “Dear Answerman, I just started dating this girl, but I got the crabs from her. How do I tell her?”
Dear Ken, this is your version of Captain Kirk’s Kobayashi Maru test. No one has ever found a solution that doesn’t end with her trying to scratch your eyes out, while simultaneously telling you (and everyone on Facebook) that you have a penis the size of a mushroom cap and the sexual endurance of a slug on Xanax.
Tanya K. from Oswego Wisconsin writes, “Dear Answerman, my fiancee said he wants to pick my wedding gown. I want to do this with my mom and friends, but I don’t want to upset him, what should I do?”
Dear Tanya, let’s talk about what kind of fiancees help pick wedding gowns.
The first kind are control freaks. If your fiancee is one of these you’re in for a life of being treated like a child. Every waking decision will be made for you. It sounds nice, until he tells the waiter, “She’s gonna have the weight watcher plate. She’s trying to lose that lard-filled doughnut she calls a waist.”
The second kind are the closeted gay men. Honestly, this may not be a bad thing. He’ll know what shoes go with which bag, take you to musicals and love to chit chat about the Kardashians. Of course, the downside is that sex will be infrequent and usually end with him saying, “Excuse me while I go throw up and cry.”
Sounds like you have nothing, but joy and happiness in front of you.
Tanya sent us this picture with a note saying, “Good news, he isn’t gay!”
Jimmy J. from Bronx, NY asks, “Yo Answerman, Shyanne be getting up in my grill about marriage and shit. She threatenin’ to leave my ass if I don’t be giving her a diamond ring. I’m a player yo! Jimmy J, can’t be roped into a commitment! Do I break up with her or just string this bitch along?”
Dear Jimmy J., I have begun a Kickstarter campaign to get you a vasectomy. In the meantime, if you feel the need to spread your seed, masturbate and use a tissue…or in your case, an empty pack of Marlboro Lights. Regarding Shyanne, I’m not sure what she ever saw in you, but please break up with her so she can find her true love…an unemployed, middle school drop-out, doing a 15 to 30 for armed robbery.
Anna V. from Beaumont Texas asks, “Dear Mr. Answerman, my fiancee isn’t circumcised so his thing looks like an earthworm. I’m not sure I can spend the rest of my life thinking my husband has a worm in his pants. What should I do?”
Dear Anna, would you be writing me if instead of an earthworm his penis reminded you of an anaconda? Exactly. Let me leave you with some advice my mother gave me, “Size is just a number, but love is unquantifiable.” Of course take that with a grain of salt, my mother liked to eat poop and had six litters from random dog park sex.
Maya B, from Provo, Utah, asks, “Dear Answerman, I’ve never had an orgasm with my fiancée, but he said “it’s not important because we love each other.” What do you think?”
Dear Maya, imagine your sex life as running a 100 yard dash, with your fiancé on your back, and at about the 90 yard mark he jumps off, declares the race over and himself the winner…then he takes a victory lap followed by a long nap. If that sounds like “love”, congrats, you’ve found your Prince Charming.
Shila M. from Newberg, Pennsylvania asks, “Dear Answerman, I think men with facial hair are disgusting. If guys aren’t going to shave, maybe women should punish them by not shaving too.”
Dear Shila, below is a picture of Debbie. Debbie’s been protesting male facial hair by not shaving since 2006, which is also the last time a male, who wasn’t homeless, had sex with her. What Debbie and you have forgotten is that a “successful protest” gets the masses to demand change, while an “unsuccessful protest” gets you herpes from a guy named Captain Gin Bucket.
Casandra M. from Austin, Texas asks, “Dear Answerman, I would rather pleasure myself than have sex with my husband. Is that normal?”
Dear Casandra, professionals preach the necessity of freshining up a stale sex life, but “professionals” are oblivious to the damage 20 years of domestic beer, Cinnobuns® and back hair have on sexual magnetism. My call, keep doing what you’re doing and throw the guy a hump every once in a while. If having sex was always supposed to be fun there would be a ride for it at Disneyland.
Carissa M, from Prescott, Arizona asks, “Dear Answerman, my friends say that I should break up with my boyfriend because he isn’t hot enough for me. I think they’re right, but he’s such a nice guy. What should I do?”
Dear Carissa, “hotness” is a hard thing to quantify, but luckily, being shallow is not. Please break up with him, it’ll be nicest thing you’ve done for another person, since the night you blew that cab driver because you were out of cash.