Mailbag From A Girl: How Do I Tell Him I Want To Try Anal?

Dillon Cheverere11 years ago

What’s gotten into you perverts? This series used to be fun for the whole family. It was mostly G-rated. Now it’s all butt sex and ball gags. I can’t say I’m upset with the raunchy progression of Mailbag submissions as of late, with the inner-familial sexual attraction and dominatrix inquiries we’ve gotten over the past week, and now we have this equally raunchy one: a girl who is ready to try anal with her best friend, but doesn’t know how to ask him.

Let’s get right to the email.

Aye Dorno,

Hey, my name is [name redacted] and I need some advice from someone who’s going to give it to me raw and dirty, no bullshit. I’ve seen your work so I know you’re the man for the job. I guess this is the part where everyone insults you and makes you feel like shit but that’s stupid for two reasons, 1. you’re giving me advice so that’s counterproductive 2. you’re hot so…nuff said.

Okay, so let’s get to the butt and soul of this email. I’ve been hooking up with my best friend for a long time now, I don’t want to date anyone so I stick to what works. I think he and I have been hooking up long enough that asking for anal is okay, I just don’t know how to ask. Saying “sooo buttstuff?” doesn’t exactly fit into conversation well. He’s been my best friend for long enough that I actually care about what he thinks so I don’t want this to blow up in my face without getting what I want. I’ve asked some of my sisters for advice on the situation but not all girls are as into socks up morals down as I am.

So please help me out with this. How do I ask for anal without things getting too weird? Thanks.

Peace and buttstuff,
[name redacted]

Aye Butt Sex Lady, I’d be happy to take a stab at this one for you. Oh, I asked her for a picture with the promise to conceal her identity. Here it is:

Now, full disclosure: I’m not an anal guy. Not my thing. It just isn’t. For lack of better, more eloquent reasoning, I find it a little gross. You know, because that hole is for poop. But also because the asshole is a sexual input that guys and girls have in common, and for some reason, that kinda freaks me out. Like, in my head, I’m able to imagine what the girl is feeling while engaged in butt sex because I also have an asshole, and that makes me really sexually uncomfortable. Now I’m wondering if I share this quirk with anyone else. I digress.

I don’t pass judgement, however. At all. Different strokes, different folks. I get it. I’m only telling you this so you know that my response to your question is coming from someone not into butt sex, which I think will be helpful.

Having revealed that, I can honestly say I wouldn’t be turned off if a girl, especially one I was as close with as you and your friend are, came to me with a first-time anal proposal. It would show me that she trusts me, that she’s comfortable with me, and that she’s willing to get her absolute freakiest she’s ever been with me. It’d be a huge compliment to me, and remember, I’m freaked out by it.

I suggest waiting until both of you are drinking alone together. Then ask him what his deepest, dirtiest sexual fantasies are. After he gives you some bullshit about a naughty nurse or being tied up and blindfolded, he’s going to ask you the same question. This is when you lay it on him. Hit him straight. Tell him you want to try butt sex, and you want to try it with him.

You can’t lose. Best case scenario: he’s into it. Worst case scenario: he’s turned off by it and you’ll have to endure an awkward conversation about it the next day. In this case, you can blame it on the a-a-a-a-a-al-co-hol.

Here’s a little secret to put your mind at ease about asking him: every single guy is, at minimum, intrigued by the thought of trying it at least once, just to see what it’s all about. Good luck..