The Ask Anna Column Is Back And A Guy Wants To Know If He Should Let Himself Be Fucked By A Guy...For His Girlfriend, What?


(Chicago Tribune)–

I love my girlfriend and I do anything she wants, including a three way with another guy. I mostly watched her at first, but she wanted me to join so I gave him a blowjob with her and by myself. Now she wants us to have anal sex, too, and I’m terrified of how much pain it will be. His penis is really, really big, way bigger than my girlfriend’s dildo. Should I man up and —Take It?

Dear TI,

Only if you want to! (Not because your girlfriend wants you to.) Go very slowly, however. Start with a single lubed finger and keep applying more lube as you play around down there. You’ll want to give your butthole plenty of time and preparation to adjust to more penetration. If you want to practice, you could also do so with your girlfriend — and a bigger dildo. And props to you for being so game and adventurous. Glad y’all are having fun threesomes. Be safe!


I fucking love the Ask Anna column. Nothing is out of bounds and she never says no to anyone about anything. Sure, bud…totally normal and healthy to suck a guy’s dick, let that dude plow your girlfriend, and then let him take his huge cock and throw it in your ass…just use a lot of lube and be safe! Like seriously what the fuck? I don’t care how “sex positive” (or whatever the terminology is) the appropriate reaction to a guy wondering if he should “man up” and take a dick in the ass is this:

More realistic and helpful advice is to just tell this dude that he’s gay. If you don’t care about seeing your girlfriend get plowed by a dude with a big dick and then you’re cool with sucking his dick and then also taking a dick…that’s quite literally gay. And that’s okay. You don’t need a girlfriend who is into super weird shit to be gay. Just be gay. And if you’re not gay and still comfortable with this then I would say that you’re probably still gay. That would be my advice. It’s pride week. Let your flag fly.

PS: Another SHOCKING column from Ask Anna. I think these have to be fake. I am blogging them under the premise that they’re real questions sent into a real person, but I mean..c’mon Anna. This is getting ridiculous.