Despite my strong propensity for avoiding any and all forms of anal play when I was younger, one fateful night soon after May and I got married, she took me right into the heart of anal play with a simple impulse of hers: to finger my butt hole. Here is how it happened.

But first some background about my extreme avoidance of anal play. Even when May and I were just dating and starting to have sexual relations, I made it very clear to her that I did not want her going anywhere near my bottom. No rubbing my butt cheeks, no spanking them, and definitely nothing near my actual butt hole itself. Part of the reason was simply because I had a lot of hair there right between the cracks that I did not want her seeing (especially when the relationship was just starting out and we were still getting more comfortable around each other, especially sexually).

But a larger part was simply because I did not see the appeal for such activities, especially considering how amazing blowjobs and regular vaginal sex feel on their own. So I guess in essence I also just felt that it wasn’t necessary in the first place. I mean, why would you try changing a good thing for something that (in my case) didn’t even seem appealing in the first place? Little did I realize that trying new things, even if they don’t seem appealing at first, can really lead to amazing improvements to my sexual pleasure, as was the case here.

For all the five years we were dating, I never let her anywhere near my ass, although I did allow her to start grabbing my ass on occasion, since she found my behind super sexy. But still no anal fingering. A few months after we got married though that all changed. One night we were getting intimate and May was on her knees giving me a blowjob. Her hands were grasped behind my nude buttocks and was really getting into. When she moved on to deepthroating, at one point she started gagging and had to pull back a little including lifting her hands away from my butt. And when she came back in to deepthroat some more, her right hand was misaligned from my left ass cheek and her hand slid into my butt crack!

Her deepthroating was just too good and I didn’t even have the wherewithal to stop her mid-blowjob to get her hand out of my butt crack, and once she noticed that I wasn’t going to stop her, she decided to locate and playfully stroke the outside of my butt hole – in other words, the very basic form of anal fingering. And it took some time, but I realized that it felt amazing! Once she finished giving me head, I told her that what she was doing behind the scenes felt amazing and she was shocked but ultimately glad that I felt that way. And ever since, we’ve been incorporating anal fingering into our sex life.

I think the reason it felt so good was because there are so many nerve endings on the end of my butt hole. And that is not something I really knew about (or noticed) until I actually had it done to me. It just felt tingling and gave me shivers throughout my body that are the perfect complement to penile stimulation. And note that May wasn’t only doing this to me while giving head. We often did it while we were in the missionary position, with May reaching back behind me as I was lying on top her here, and even did it while making out on occasion (after we took off all our clothes).

Note that there were times when May and I experimented with her inserted her fingers up my butt. But I really didn’t like it at all. Having something actually inside of me felt way too weird, and I couldn’t even stomach just the tip of her finger inside of me before I had to ask her to pull it out. Having said that though, just external fingering itself felt so freaking awesome, as long as all of the touching occurred externally (at least in my case).

For anyone looking to try anal fingering in general, just note that your partner needs to be pretty careful with their fingers once they finish fingering you, as your butt hole will never be 100% clean and any bacteria or other contaminants will end up on their fingers. It should definitely be safe enough to touch most of your body, but definitely keep it away from your eyes and mouth, unless you wipe it clean with a wet wipe or wet hand cloth or the like.

Despite my initial reservations about anal play in general, thanks to May I found a new and exciting way to stimulate myself sexually. And it has sparked our sex life in ways that I never imagined previously. While actual butt hole fingering may be too much for many guys, lightly fingering the outside of your butt hole is much less invasive and can be just as pleasure, if not more so. So if you are already intrigued by the prospect of anal stimulation, or even if you are like how I was years ago, you’ve got nothing to lose by trying anal fingering (and other forms of anal stimulation), but so much to gain!