The Best Laid Plans

Found at Romeo Tees (yes, it’s a shirt you can buy! I want one)

I love anal sex. I really don’t say that enough on here I think. I love giving it, receiving it, just about anything about it. Well, I don’t like when it’s messy, but I don’t get upset when it is because that’s part of it. Obviously when you’re playing with the backdoor there is always the possibility of shit, and while I’m not into that I just roll with it and always keep tissues handy. Wendy Blackheart actually has a wonderful post about shit and anal sex called shit happens on her awesome anal-sex oriented site Ask the Ass Bandit, but I digress.

Onyx feels much the same way as I do about anal sex. In a way it’s one of the things that brought us together, or at least was a big part of our relationship, as much of our online relationship was played out in an anal sex channel on irc.bondage.com. He’s actually quite an anal slut when the mood strikes, as I am. We both enjoy giving and receiving, which makes it that much more fun.

Despite both of us loving anal we don’t do it as often as we might want. It takes quite a bit of preparation and forethought, which we don’t usually have when we fuck. Usually it’s just an impulse when we do it and not planned out.

The last few nights we’ve been talking about me fucking his ass. Ever since I got Brando, really, we’ve been talking about it, though not talking about me fucking his ass with Brando because that prospect was a little too intimidating. Neither of us have the courage to take Brando anally yet, though I think it’ll happen sometime, but that’s another story.

Since we’d been talking about it for a while, last night while we were settling down to bed, Onyx brought it up again, and I told him to go get the required assistants, specifically one of my harnesses and whatever dildo he had a preference toward. He came back with Boy Butter, my Hardcore Harness, Bandito, Celestial Perfection, and Tantus G-Force Wand. The last one isn’t harness compatible, but is great for fucking with because of it’s extended handle.

I did a few things to clean up and then instructed him to get on the bed (futon). He knelt and then moved to all fours, moved a pillow under his chest to facilitate his position before letting his head fall to the bed, resting on his hands. As I watched I slipped the Celestial Perfection into my harness and then slipped the harness on. I wasn’t going to fuck his ass right away, I would first use my fingers to open him up, but I wanted to be ready to fuck when we got there.

My Rubber Whip was lying on the floor in front of him, so I instructed him to hand it to me. I lightly began slapping his ass with the whip, trailing the soft falls across his back, and lightly teasing his balls with the strands. He’s not big into pain, and though the whip can sting if used hard, I was being sure to be light, using the sensation play to heighten his excitement.

I lubed up his ass and my finger with the Boy Butter and began working it in and out, slowly and surely, as he moaned and writhed before me. I added a second finger, then a third, adding little bits of lube each time a new finger was inserted. I remarked on how much of an anal slut he was being, and occasionally stroked his cock or massaged his balls. Whenever he started to tense I made him squeeze his ass around my fingers and then release completely.

When I added a fourth finger he tensed and pulled forward so my fingers pulled out, letting me know that had hurt. I worked back up from one again and added more lube before adding the fourth finger, but was able to get all four in easily that time, and he liked it. He was pushing back against the fingers as I moved them in and out. I asked him how many fingers he thought I had in.

“Three?” He asked curiously.

“Nope. Four.”

“Wow.”

I grinned and moved them a little more intently in his ass, my other hand squirting a bit of the lube onto my cock as I did, getting ready to fuck him with the silicone that was now transformed into my pearly white cock.

I had already made sure the curve of the cock was going to be at the right angle to get at his prostate, so I started slowly inserting. He pulled forward suddenly, letting me know that it hurt for some reason. This also popped my cock out of my harness, which was annoying, the base is pretty thin and went right with him when he jerked his hips. I added more lube, tried again with the cock out of the harness, and again it hurt. We tried a third time, got farther in, but it just wasn’t working right.

We paused for a few moments and decided to try Bandito instead. I loosened the harness so I could slip Bandito in, during which time one of the straps came undone completely because I had pulled too hard (it has tighteners like the ones on backpacks to make the shoulder straps longer/shorter) and I had to take it off and lace it back the right way before putting it back on again.

While I was doing that, Onyx remarked that perhaps the position was the issue, and decided to move onto his back instead. I went and grabbed my sling which helps the bottom keep their legs in the air more easily so that he would be more comfortable in that position.

I again started with my fingers while stroking the lube into my Bandito with my other hand, getting him back to the point of being open for my cock before going to insert it. It hurt again. We decided that maybe he hadn’t cleared his backdoor completely, though he had gone before we started to try and avoid this problem, so he went into the bathroom to do this.

He came out a bit later, claiming something wasn’t quite right, and we should maybe wait for another time. I’ve had the same experience before, having anal be unexpectedly painful and just not feel right, so I understood. We cleaned up, snuggled a bit, and ended the night with me getting fucked doggy style instead, though not in the ass.

Even when you’re thoughtful and ready for anal, sometimes it just doesn’t work for whatever reason. We will try again, though, soon, and next time it’ll work. Or so we hope.