If you’re following my blog you know I’ve been warming up to the idea of bottoming, trying to get past the block that prevents me from engaging in anal play. Well, early last week I made a trip to the sex shop and bought a Fleshlight—and a dildo.
A couple weeks ago I shared a conversation I had with a friend about my need to associate bottoming with my masculine side rather than my feminine side. I talked about how I don’t see either penetration or being penetrated as necessarily masculine or feminine traits, yet in real life I failed to see that while I applied that to others, I still felt the need to force bottoming into the masculine box for myself.
And then I spoke to an acquaintance online. I asked him whether he related to bottoming from a masculine or feminine perspective, and his response was, “I relate to it in that I like it. It’s not masculine or feminine. Stop thinking about it, Omni, and just roll with it.” In that moment it became crystal clear that all I needed to do was apply what I already felt about the gender neutrality of the positions to myself. No fucking shit, right?
A few days later I popped into the sex shop to make my purchase, slightly giddy with excitement as I rode my bike back home. Once I got home I noticed that a fuck buddy had texted me to see if I had time later that day, and to my surprise I texted him back to say that I was busy—I turned down his offer to have a threesome with my new Fleshlight and dildo. And what a threesome it was.
I can now say with surety that I understand why sticking things in the bum is such a turn on for so many people. Admittedly, I had to take it slow and steady, had to learn to relax and breathe. But once I got past my initial discomfort, once I finally managed to slide the dildo far enough in to really feel how hot it can be, once my overpowering inclination was to push it deeper rather than pull it out, my eyes opened wide and a grin spread across my face: in that moment I totally fucking got it.
A few times my thoughts returned to the question of masculinity and femininity, but I quickly banished such thoughts and focused on how good it felt, which wasn’t very hard because it felt so damn good. And once I felt comfortable enough to hold the dildo with one hand and the Fleshlight with the other, things got really intense in a very enjoyable way. Wow. Just wow.
For the time being this is something that will stay between me and my dildo. I want to explore this further before I go for fucking or pegging with real people, but I’m glad I took this step and finally stopped overthinking it so much. Because when it was all said and done, I didn’t feel any more or less masculine or feminine; I felt sexually satisfied.