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I would like to point out the incredible journey that anal sex has made in our culture, from something taboo and almost never spoken about to now, where it frequently shows up in pop culture or conversations about sex. Maaaybe that’s because I’m a swinger, but I don’t think that is the only reason. My personal journey with it has been similar in that I didn’t know about it, to never imagined myself having it, to totally enjoying it. That only took 30-ish years, with most of it happening within the last five. Perhaps similar to its journey in pop culture. I know that even amongst my swinger friends, this is an iffier proposition, so I thought this might help some people on their own journey with it if they are on one.
I had written anal sex out of my relationship bylaws so clearly, I had some strong feelings about it.
The seed. In my 20s a girlfriend and I were talking about our sex lives. She mentioned that her sister loved anal sex, but that she didn’t like it as much herself. I was shocked. Women were having anal sex on the regular?
The bad seed. My first couple of experiences with anal were not so good. Nothing bad happened except I was really nervous about it and trying it mostly because my boyfriend at the time wanted to. It wasn’t great or even good — it was tolerable. The second time we ended up in a fight after he said something (exactly) like, “You are not even trying to enjoy it.” I ended up in the bathroom thinking I was probably going to break up with him. OK, my first experiences with anal were pretty bad.
The foggy seed. What I remember is telling my next boyfriend (my now husband) that I would never be having anal sex again so if that was important to him, then he should move on. He claims to not remember that conversation, but I’m pretty sure it didn’t just happen in my head. He remembers us trying it a couple times and that I liked it. I claim not to remember that. I might have been drinking a fair bit to have gotten that adventurous. I mean, I had written it into my relationship bylaws so clearly, I had some strong feelings about it.
We took a class called “How to Anal like a Porn Star” taught by, of course, a porn star.
The seedling. The first year that we attended Naughty in N’awlins, my nerdy husband and I were very excited about all the workshops and learning opportunities there. We both picked out all of the classes we wanted to attend and when we compared notes, we realized we would not have time for anything else. We pared back. One of them that stuck was “How to Anal like a Porn Star,” taught by, of course, a porn star. “Don’t get too excited,” I said, “I’m just intrigued.” And intriguing it was. Something happened in that class that changed everything. I took a vow. Yes, a vow. The promise she made everyone in the room take was to never just tolerate anal sex (that sounded familiar) but to enjoy it. “If it’s not feeling amazing,” she said, “don’t do it,” and she proceeded to show us how to train for anal. That was enlightening already. She had an anal training set (plugs — WITH A BASE, ALWAYS WITH A BASE — we learned), and she climbed up on a table and showed us how one would insert such a toy. While my description may not elicit this, let me tell you that this was the most professionally done training session one could imagine while teaching anal sex. We were impressed.
Slowly, ever so slowly, which is the best way to have anal sex, in my opinion.
The bloom. It didn’t happen right away. I still had a lot of anxiety and bad memory-association to clear away. We did get a training set, and I did start using it. We began experimenting with it… slowly, ever so slowly, which is the best way to have anal sex, in my opinion. Toys and fingers were used more often. More fingers were used more and more often. It was clear that anal stimulation would ramp me up very quickly, but I was still afraid of my husband’s cock. It’s not small. On the other hand, I didn’t want to use anyone else’s cock for this, which felt like an even more intimate act. We worked our way there and now, I can honestly say, I do very much enjoy anal sex. I have not broken my vow. I’ve even gone as far as DP (Double Penetration, having one cock in the ass and one in the pussy). Recently, I allowed someone else in the back, something my husband and I agreed we wanted to try with him on the bottom. It was a blissful success for all.
I have found that, like sports, it is mostly mental
The lessons. What I’ve found, and that which is consistent with many of the women I talk to about anal sex (fairly common topic, actually), is that it is like sports in that it is mostly mental. If I’m feeling open, I can be open in all kinds of ways. Part of what can help feeling open to it is also prepping for it — a cleaning of the system beforehand (it doesn’t have to be right before) to remove some of that concern. If I’m feeling even a tiny bit anxious or uncomfortable or pretty much anything other than totally open, it’s not happening. Some days if I’m not feeling that openness, I can’t even get a small toy in, let alone my husband. Of course, it’s easier to feel open now with more and more amazing experiences under my belt, but still, it is required. I wouldn’t say I anal like a porn star, but I would say I anal like I never thought I would or could before.
PSA. If you aren’t having anal with a regular or trusted partner, condoms are especially important. I didn’t feel like I could write about anal without including this. OK, anal on!