Dear Gay Dude: I Want To Have Anal Sex With My GF

Dear Gay Dude,

Like many other straight men before me, I want to attempt anal sex with my girlfriend. But how do I go about this delicate subject? Do you think she’ll be into it? Also, will she, like, shit on my dick?

-Want My P In My GF’s A

Hey Want My P In My GF’s A,

You’ve come to the right place! Dicks in asses are pretty much my speciality. OK, so here’s the deal. Initiating anal sex with your girlfriend is going to be tricky. Even though most of my girlfriends have tried it (to varying degrees of success), some girls are not into it at all and you can’t fault them for that. Women don’t have a prostate so anal sex mostly just feels hideous kinky for them. When a girl tells me that it actually feels good, I get suspicious. How? For me, a dick in my ass feels super weird until they start hitting my prostate and then it’s “Hey Gurl Hey!” I can’t imagine it feeling particularly good without some kind of G-spot lingering at the end of the asshole tunnel, but different strokes for different strokes!

OMG, you know what you should do? Have her finger your asshole beforehand. Have you done that before? You may have once and then felt super bad about it because it felt really good. Don’t be ashamed though! Like I said before, a guy’s prostate is essentially our G-spot and it’s located in our ass. It’s kind of a cruel joke for straight men. The one thing that feels the most pleasurable is pretty much the gayest thing imaginable. HA HA. Gay men get the longer end of the stick for once. Anyway, if you let her penetrate you, she might be more willing to be penetrated.

As for the main event, it’s important to remember that slow and steady wins the anal sex race. Lube that shit up so it’s basically like a swimming pool. Depending on how well-endowed you are, it might hurt a lot or just be super uncomfortable for her. Actually if you have a big dick, you should probably not fuck your girlfriend in the ass because it’ll be too much P in the A. If you’re lucky enough to make it inside without her screaming bloody murder, make sure to listen and continually ask if everything’s okay. It’s going to be like the Special Olympics of sex and that’s okay. It needs to be nice and slow.

Regarding the issue of shit, it shouldn’t be a problem if your girl is “clean” but that doesn’t mean it can’t happen. Feces have been known to make a cameo appearance in anal sex and it’s gross and traumatizing and no one ever talks about it. They have shit shame, but it’s like, no shit there might be shit. You’re using an exit as an entrance. Shit can happen. Just make sure she cleans herself up and…takes care of business. If she does shit on you, don’t freak. If you’re still together when you’re 80 years old, you’ll probably be seeing some more of her crap so get used to it now.

OK. Do you have all the 411 you need? Godspeed, you ass emperor. Have a sexy time.


Gay Dude TC mark

Ryan O'Connell

I'm a brat.


More From Thought Catalog

  • phmadore

    Actually it's possible to stimulate the G-spot from the anus side. Just saying.

    • Ryan O'Connell

      OMG RLY? welll…shit.

  • opus

    “godspeed you ass emperor” made me chuckle

  • Boh

    you missed out one MAJOR point for us girls – make sure she is really uber-gagging-for-it turned on – it'll make the 'hole' affair a whole lot easier…

  • dementia inc.

    Man that was helpful tips for shitty situations!

  • Tanesha Shireman

    Yeah, and if she's not into it DON'T PRESSURE HER. Seriously, I'm willing to try a lot of things but anal ain't one of them and having my ex (then bf) pressure me for it made me resent him and not even want to do stuff for him that I normally would be willing to do.


    Sweet ass ass fucking

  • Andrew


    • Kasey

      Omg lol at your icon and name. When I saw it I was like “Oh Andrew, you kinky bastard.” but then my fangirlness wore off and I became rational.

      This reply has contributed nothing to this issue and I realize that…

  • Greg Petliski

    “If you’re still together when you’re 80 years old, you’ll probably be seeing some more of her crap so get used to it now.”

    Now thats love.

  • Beb

    Yup, I personally preffer being anally penetrated than doing it the “usual” way. People have various pleasure spots and the vagina seems to be the most overrated of them all in my oppinion;) The thruth is, on the inside it is not that sensitive (which is because of the baby bearing… thing;p).

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