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.
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