I’ve been thinking a lot about the Kink of the Week prompt on anal sex and had nearly talked myself out of adding to the amazing posts on the topic because I don’t feel that my ‘anal journey’ has been very eventful. Like so many, I tried it well into adulthood and only after much consideration. My bestie is a fan and was very encouraging that I should try it and after much discussion with one of my partners at the time, we agreed to embark on what would be both our maiden voyages. I won’t regale you with the gritty details but I will say that it went well enough. We tried, failed, re-tried, got it right and all of that came with lots of learning and discussion. Once victorious, we did it again and soon it made its way into the semi regular rotation of things we do because it was much better, worlds better, than I expected. All’s well that ends well, right? Sure, but that doesn’t mean that it was easy. Despite him being very patient and gentle, despite the gallon or so of lube we used, despite being adequately “warmed up” and following directions I’d received from a friend who was a self proclaimed “power bottom” (first time: spooning, on your side, not from behind!) I still cringed at the prospect that it might get … messy.  Frankly, I still do. And it has.

I’m not one for sterile sex. I like a bit of messiness, I like that filthy feeling when there’s that sploosh of cum or hot gob of saliva in the mix. I like sweat and tears and I have survived mis-swallowing a blowjob and had it come out my nose. I am down for mess. However, no amount of preparation and good timing can prevent me from quickly killing the mood as he pulls out after, by fearfully asking, “Is it messy?!?”. Let’s be real, sometimes it is. Not much, it’s not a horror show, it’s not a triple X Willy Wonka parody back there, but it’s not always all roses either. Yet, I survive, in large part because he is not squicked out. He just chuckles and shrugs and we shower. No big deal. That, for me is the key: even if I’m embarrassed or feel a flicker of shame, I am safe because his response is consistently neutral. We have talked it through, I know his stance, I have heard the reassuring words dozens of times and he is steadfast in them.

Recently I purchased my very first strap on with the intention of using it with The Boy and making all our mutual pegging dreams come true. We both anticipated its arrival and shared detailed fantasies on how the scene(s) might play out. I tried it on alone and paraded around my apartment in it to get used to it, privately and self consciously thrusting and testing the structural integrity of the dining room table since that was a repeated fantasy of his, that I bend him over it and fuck him soundly. Everything about the upcoming christening of Sven, as the equipment is known, was exciting and the anticipation was sexy and fun. Then I started to think about what I know to be true about the logistics of anal and I got nervous. When I expressed this nervousness to my bestie she retorted casually, as she should: just talk to him about it. Of course that’s the answer; a mature, candid dialogue on the pit falls of butt stuff, a way to align on expectations and best practices, the perfect answer to all the taboo and worry, the embarrassment and vulnerability. Easier said than done,  it seems. The old adage from my youth bubbled to the surface of my mind: If you’re too immature to talk about sex you might not be ready for sex. Did the same apply to butt stuff? If I couldn’t form the words and have the candid conversation, could I go through with fucking his ass? So far, the answer remains no and I can’t quite articulate why, but until that dialogue is possible and comfortable and complete, I just can’t seem to go through with it. Anal sex is not the be all, end all of our relationship but it remains high on both our lists. I am hopeful that we’ll make it happen, that we can gain enough familiarity that it happens naturally and without too much incident. If it doesn’t happen, or it does and goes poorly, we will re-calibrate or try again or just move on, because if I’ve learned anything in my life about sex and bodies it’s that sometimes shit just happens.

Still feeling Kinky? Read more at Kink of the Week …

13 thoughts on “Shit Happens”

  1. I really enjoyed reading your beautifully written and candid post. You write so naturally and honestly. I just felt so happy and relaxed reading this as if I were in the company of a friend. Also you made me yearn for something I have never had the pleasure off trying. Either giving or receiving. CP xx

  2. I’m not one hundred percent sure what you are concerned about as you’ve got the standard anal sorted well.
    I use a condom with my anal sex toys then I can just roll it off and chuck it. Other than that the standard towel, lots of lube and wipes for a quick clean up, pre shower. Taking it easy as you’ve mentioned in the first half of the story, starting with fingers and toys. Ryan loved it and so did I, but we certainly talked about it quite a bit beforehand.

    1. That’s the challenge: the conversation. It’s somehow a bit of a block in intimacy that I wasn’t expecting would be there but it is. Perhaps we shall overcome it in due time.

  3. Maybe you might find it easier to have the conversation through through writing rather than talking. You might find it easier to discuss that way, maybe write a sex scenario of what you fantasy looks like and use that as a starting point to talk about the other practical aspects


  4. Can I ask what you think would facilitate it? I admit it wasn’t something I discussed a deeply as I should’ve when I was on the receiving end, and when I was hoping to try pegging on the guy I’d been seeing, it was all Fantasy not frank talk. I’m just curious, because I know discussion is important. For safety sake. I do like Molly’s idea. And I wonder if writing it here has helped any? I do love your honesty here

    1. I think it’s a matter of plain comfort. This is a person I can’t burp or fart in front of either and by virtue of how casual it is, that next level familiarity has always seemed unlikely. I originally thought it was mess shame but the barrier for me is the overall inability (on both our parts) to invest to a level where normal bodily functions lose their taboo. The issue is more that we are emotional strangers, less that the risk of the mess or logistic issues exists, because if we weren’t lacking that closeness it wouldn’t matter.
      The “answer” is time and willingness to be vulnerable, which sadly, doesn’t always come.

      Writing here has helped clarify a lot. In fact, we broke up last night. So there’s that …

  5. Loved reading this – i have had good anal and anal I should not have had – I am with you on “it’s not the be all and end all” – but would like to get it right completely but is not the easiest thing to talk about openly

  6. I love your frankness here. My paranoia about mess is preventing my enjoyment. Maybe what I need is for mess to happen and seeing how we both react to it for me to get over my fears!

  7. “even if I’m embarrassed or feel a flicker of shame, I am safe because his response is consistently neutral.” – THIS is what’s allowed me to do all kinds of kinky things that might make me a little grossed out. As long as JB treats it like no big deal, I can handle nearly anything.

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