An absence of grimacing

Warming my boyfriend up to anal play has been a challenge thus far — to say the least. The last time I wrote about our forays, which was in January, I noted that I was disheartened by my boyfriend’s strong physical reaction to his asshole being touched. The truth is, it was so disheartening that I just didn’t even want to try for a while.

When we did try again several weeks ago, I tossed some rimming into the mix. He wasn’t adverse to it, but it tickled him too much. I ended up with the tip of my finger in his ass, but so much time had passed by then that he asked if we could stop. So I took the condom off my finger and sighed. For not the first time, I was frustrated and upset. It seemed like we weren’t making any progress, and it really sucked to keep seeing him squirm and grimace while I tried to get him to relax.

He was bothered too. If this process involved only his mind, I’d be fucking him with a strap-on up the wazoo right now. But his body is stopping us. His very strange physical reaction to anything coming near his butt is stopping us. He has never, until recently, regarded his asshole as a sexual spot. He is trying to change that because he knows how much it means to me. But even knowing how much he is trying, I am usually left with tears in my eyes, feeling like we will never succeed.

But things took a turn for the better the other night. I don’t know what it was, although it may have helped that he was slightly buzzed. We fucked first, with the Throw under us and the Bootie in my ass — that is, until it kept popping out. I was so relaxed that it just would not stay in. This was actually my first experience of double penetration with a sex toy and a real cock, and it was awesome while it lasted (I’m going to try it with the Romp next time, definitely). But that was just the build-up to the ass play…

My goal was to keep him hard for as long as possible while I played with his ass. I was somewhat successful. I propped his ass up on the Wedge and put on sky blue non-latex gloves — the first pair out of a newly-purchased box, our first box of gloves — and began slowly touching his ass with a lubed finger while also slowly playing with his cock. There was minimal twitching this time, and it wasn’t long before my finger was halfway in his ass.

“Does that feel good?”

“No, but it doesn’t feel bad.”

This is an improvement. It may not sound like it, but it is. My finger was halfway in his ass, he was not grimacing, and I was ecstatic. His erection faded, but he was not uncomfortable and didn’t immediately want me to stop. When I eventually took my finger out of his ass, I felt far more optimistic than I ever have.

As a finale, he fucked me with Mr. Man while I held the Hitachi on my clit. And yeah, I was happy.