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I'm seeing a guy right now that is funny, cute, and seems pretty nice. I don't think we're a good match longterm—he's not sure if he wants kids and I do (and don't have a ton of time), plus we have some potential personality incompatibilities (I'm pretty type A and think his disorganization might bug me if it got more serious; I've learned from past relationships opposites may attract but it's not always great for cohabitation)—but it's nice seeing someone and I am also trying to be open-minded. He is also pretty into ass play, mine and his. I am into people being into (and in) my ass, and I can get into getting into theirs with the right guy (with my ex, I often wanted to initiate sticking a finger/tongue in there bc I was so into him).

But with this new guy, I'm having trouble. We've hung out five times, started hooking up time #4. The first time we hooked up, he asked me to stick a finger in his ass when I was blowing him. I wasn't excited about it—maybe bc it's kinda early on, maybe bc I don't see a lot of longterm potential which would make me excited about being intimate in that way, maybe bc he had farted earlier in the hook up session (!) which was kind of a turn off. (But hey, human bodies right?) Still, I was trying to be GGG. I noticed afterwards something under my nail but sometimes I can just get stuff under there during day so I ignored it.

Next time we hooked up he asked me to again. He had been pretty good with me about listening to what I wanted so I wanted to reciprocate. This time he wanted me to go deeper with my finger (for record I have really small hands, so it still wasn't that deep), I went for it, and when he finished there was definitely some shit on my fingertip when I went to bathroom. I was really grossed out, but didn't tell him. The next morning he asked me to do it again and I said no. He was cool about it and I think it was the right thing for me to do so I didn't hate myself/him, but I also felt uncomfortable esp bc I've been having to be kind of demanding about other things (touching me the way I like, setting up plans in advance, etc) and he's been responding well.

He wants to hang out again. Part of me does, but part of me is so turned off now in a more general way. Should I just toss this one back in ocean since I don't think he's Mr Right anyway? Should I tell him what the issue is? Should I hook up w him but just not go near his ass, ever, since he doesn't seem to know when it's clean or not? Or do I need to get over this and accept it as part of the deal? Does it matter that he has some GI issues he's figuring out (trying not to eat gluten etc)?

I can't tell if I'm over or underreacting here. Thanks for your help!

Feeling I'm Never Gonna Enjoy Rectum

You noticed something under your fingernail the first time—something you must've suspected was shit—but you didn't bring your finger to your nose to confirm (or dispel) your suspicions? I'm gonna beat the commenters to the punch and call your letter fake—FAKE! FAKE! FAKE!—because smelling your finger and then, if it was shit, either cutting it off or washing it thoroughly is the obvious reaction/course of action here. I mean, come on.

But just in case you're for real not shitting us...

One shitty finger shouldn't be a deal breaker, FINGER, but it's a great excuse to pull out if you're not feeling it. As for two shitty fingers... well, if I may paraphrase the divine Lady B: To shit on one finger may be regarded as a misfortune; to shit on two looks like carelessness. If he's so into ass play that it's just not sex unless there's a finger buried deep in his ass, FINGER, then the onus is on him to make sure his ass is good to go, i.e. empty and clean, before inviting a new partner to start digging around in there. His casual disregard for your fingernails... well, it sure looks like carelessness of the deal-breaker-y sort to me.

And this belongs on the list of reasons to pull out: while he's been very clear about his needs, FINGER, and you've been very accommodating, the fact that you've had to be "very demanding" about the way you like to be touched—demanding because he wasn't as invested in your pleasure as you were in his—is a very bad sign. He may have listened to what you want, but he didn't follow through. And while there's a fix for shitty bums/fingers (fiber, douching, finger cots), there's no easy fix for "doesn't give enough of a shit about your pleasure to pay attention and follow through."

Technically you can't even dump the guy, FINGER, since you weren't dating officially. But don't ghost, FINGER. Tell him you're not a good fit and thank him for his time. And if you ever find a dude who is a good fit for you and who also likes having his ass fingered, fucked, or pegged, don't be shy about trying it again, FINGER. And if there are issues—which there usually aren't—talk it over with the new guy.


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