The final edition of Holiday Heat comes out on Sunday December 15. Preorder it now!

I’m sure you remember my previous posts about strap-ons and pegging, where I talk about days my butt says yes and no (or no, but I want it to say yes). Well, last weekend my long-distance partner was in town for a visit, and she brought the equipment to engage in some pegging, should I want to. There was one night where I knew it would be safe — I had just showered thoroughly, and my stomach was in good shape — so I said we should do it. Of course, I had to give her a red bottom first, but that goes without saying.

Anyway, this time she brought an even larger toy than last time — fine by me; I’ve successfully taken some fairly substantial toys during pegging activity over the years. I wasn’t afraid of being hurt; nothing anyone has pegged me with has ever caused pain.

I’m sure you want to see the toy. I know you.

There. Happy?

(I kid, I kid. I don’t mind showing it to you. I’m not embarrassed or anything.)

In any case, once I was good and ready (and remember LDP is very tall, with long fingers, so needless to say I was ready), we found a position that worked and she fucked me with the strap-on.

For about two minutes.

See, here’s the problem: my butt was saying yes, and I was also saying yes (it felt amazing), but my brain kept saying no. Or, more precisely, it kept saying “you are going to make a mess”, even though I knew it was pretty much impossible for me to do so at the time. I fought to overcome the discomfort and focus on the pleasure, but it was just too difficult to do so. My brain has a very specific reaction to certain sensations, and as I’ve written about in the past, the outstroke of anal sex is the most uncomfortable part of it for me. And this, remember, was a bigger toy than last time — in fact, it’s the biggest I’ve had in more than ten years, so there was a lot of outstroke. I was really looking forward to it, and that initial penetration was wondrous (as was the feeling of her behind me, fucking me), and I wish I could’ve gone for a little longer, but I just couldn’t do it. We both had fun, but I was a bit disappointed in myself that I couldn’t take it as long as I wanted to.

I guess as you get used to anal sex on a regular basis you accept the fact that you’re going to feel the “you are going to make a mess” feeling every time, and your brain gets over it — or, at least, you manage to ignore it. I don’t receive on a regular basis, so I don’t have the opportunity to accustom myself. I guess I could take action to change that, but it’s not often that my butt says yes and my body is ready. Or, to put it another way, my eyes are bigger than my butt.

(By the way, I asked AI to create an image of “my eyes are bigger than my butt” and it failed miserably. It was just a drawing of a curvy woman from behind, with a lot of hair and a big backside. I was hoping for something more amusingly cartoonish. Oh well. AI isn’t perfect.)